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Practical Guide to
Vegetable Oil Processing
Page left intentionally blank
Practical Guide to
Vegetable Oil Processing
Second Edition

Monoj K. Gupta
MG Edible Oil Consulting Int'l Inc.
Lynnwood, TX, United States
Academic Press and AOCS Press
Academic Press is an imprint of Elsevier
125 London Wall, London EC2Y 5AS, United Kingdom
525 B Street, Suite 1800, San Diego, CA 92101-4495, United States
50 Hampshire Street, 5th Floor, Cambridge, MA 02139, United States
The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, United Kingdom
Copyright © 2017 AOCS Press. Published by Elsevier Inc. All rights reserved.
Published in cooperation with American Oil Chemists’ Society www.aocs.org
Director, Content Development: Janet Brown
No part of this publication may be reproduced or transmitted in any form or by any means, elec-
tronic or mechanical, including photocopying, recording, or any information storage and retrieval
system, without permission in writing from the publisher. Details on how to seek permission, further
information about the Publisher’s permissions policies and our arrangements with organizations
such as the Copyright Clearance Center and the Copyright Licensing Agency, can be found at our
website: www.elsevier.com/permissions.
This book and the individual contributions contained in it are protected under copyright by the
Publisher (other than as may be noted herein).
Notices
Knowledge and best practice in this field are constantly changing. As new research and experience
broaden our understanding, changes in research methods, professional practices, or medical treat-
ment may become necessary.
Practitioners and researchers must always rely on their own experience and knowledge in evaluating
and using any information, methods, compounds, or experiments described herein. In using such
information or methods they should be mindful of their own safety and the safety of others, includ-
ing parties for whom they have a professional responsibility.
To the fullest extent of the law, neither the Publisher nor the authors, contributors, or editors, assume
any liability for any injury and/or damage to persons or property as a matter of products liability,
negligence or otherwise, or from any use or operation of any methods, products, instructions, or
ideas contained in the material herein.
Library of Congress Cataloging-in-Publication Data
A catalog record for this book is available from the Library of Congress
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A catalogue record for this book is available from the British Library
ISBN: 978-1-63067-050-4

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Publisher: Nikki Levy

Acquisition Editor: Nancy Maragioglio
Editorial Project Manager: Billie Jean Fernandez
Production Project Manager: Susan Li
Designer: Victoria Pearson

Typeset by Thomson Digital

Contents
Prefacexvii

1. Requirement for Successful Production and Delivery

of the Refined Vegetable Oils
1.1 Crude oil1
1.2 Oilseeds1
1.2.1 Maturity 2
1.2.2 Harvest Condition 2
1.2.3 Handling of Seeds 2
1.2.4 Seed Storage 3
1.2.5 Insect Infestation 3
1.3 Additional Comments on Oilseeds3
1.4 Fruit Palm4
1.5 Groundnuts (Peanuts) and Tree Nuts5
1.6 Crude Oil Handling, Storage, and Transport5
1.7 Concluding Remarks5

2. Basic Oil Chemistry

2.1 Composition of Oil7
2.2 Distinctions Between Oils and Fats9
2.3 Fatty Acids in Common Vegetable Oils9
2.3.1 Saturated and Unsaturated Fatty Acids 10
2.4 Typical Behavior of Fatty Acids11
2.4.1 Unsaturated Fatty Acids 11
2.4.2 Saturated Fatty Acids 11
2.5 Objectives of Proper Oil Processing11
2.6 Nontriglyceride Components of Oils11
2.6.1 Major Nontriglycerides 12
2.6.2 Hydratable and Nonhydratable Phospholipids 13
2.6.3 Free Fatty Acids 13
2.6.4 Monoglycerides and Diglycerides 13
2.6.5 Minor Nontriglycerides 14
2.6.6 Tocopherols 14
2.6.7 Sterols and Sterol Esters 16
2.6.8 Volatile and Nonvolatile Compounds 16
2.6.9 Color Compounds 17
2.6.10 Trace Metals 17
2.7 Oil analysis Used in Vegetable Oil Industry
and Their Significance18

v
vi Contents

2.8 Significance of the Analytical Methods and Results20

2.8.1 Iodine Value 20
2.8.2 Free Fatty Acids 20
2.8.3 Acid Value 21
2.8.4 Peroxide Value 21
2.8.5 para Anisidine Value 21
2.8.6 Soap in Oil 21
2.8.7 Conjugated Dienes 21
2.8.8 Polar Material (TPM) 21
2.8.9 Polymerized Triglycerides 22
2.8.10 Solid Fat Index 22
2.8.11 Solid Fat Content 22
2.8.12 Fatty Acid Composition 22
2.8.13 Fatty Acid Composition 22
2.8.14 trans Fatty Acid 22
2.8.15 Refined and Bleached Color Test 22
2.8.16 Lovibond Color 23
2.8.17 Chlorophyll Pigments 23
2.8.18 Trace Metals (ICP) 23
2.8.19 Trace Metals (Atomic Absorption Method) 23
2.8.20 Phosphorus (Graphite Furnace) 23
2.8.21 Phosphorus (ICP) 23
2.8.22 Smoke Point, Flash Point, and Fire Point
(Cleveland Open Cup method) 24
2.8.23 Melt Point (Capillary Tube Method) 24
2.8.24 Melt Point (Mettler Drop Point Method) 24
2.8.25 Active Oxygen Method (AOM) 24
2.8.26 Oil Stability Index (OSI) 24
2.8.27 Refining Loss 24
2.8.28 Neutral Oil Loss 25
2.8.29 Unsaponifiable Matter 25
2.8.30 Saponification Value 25
Bibliography25

3. Crude Oil Receiving, Storage, and Handling

3.1 Crude Oil Receiving27
3.1.1 Crude Oil Quality in Trade 28
3.2 FOSFA International (Headquarter—London, UK)28
3.3 Membership32
3.3.1 Trading Members 32
3.3.2 Broker Members (Full or Associate) 32
3.3.3 Nontrading Members (Full or Associate) 32
3.3.4 Superintendent Members 32
3.3.5 Analyst Members (Full or Associate) 32
3.3.6 Kindred Associations 32
3.3.7 Benefits of Membership 33
3.4 Crude Oil Unloading (Truck or Rail Car)35
3.4.1 Impact of Steam Blowing for Line Clearing 37
 Contents vii

3.5 Crude Oil Storage37

3.5.1 Special Notes on Oil Stored at Terminals 38

4. Degumming
4.1 Introduction41
4.2 Purpose of Degumming42
4.3 Hydratable Phospholipids and Nonhydratable Phospholipids43
4.4 Methods for Degumming43
4.4.1 Water Degumming 44
4.4.2 Acid Conditioning 46
4.4.3 Acid Degumming 49
4.4.4 Deep Degumming 50
4.4.5 Enzymatic Degumming 58

5. Refining
5.1 Purpose of Refining Vegetable Oil79
5.1.1 Major Nontriglycerides 79
5.1.2 Minor Nontriglycerides 79
5.2 Methods of Oil Refining80
5.3 Physical Refining Process81
5.3.1 Critical Control Points in the Physical Refining Process 82
5.3.2 Bleached Oil Quality Parameters in the Physical
Refining Process 84
5.3.3 Troubleshooting Physical Refining Process 84
5.4 Chemical Refining Process85
5.4.1 Batch Refining Process 86
5.4.2 Critical Control Points in Batch Refining 88
5.5 Continuous chemical refining process88
5.5.1 Critical Control Points in Continuous Chemical
Refining Process 94
5.6 Water Washing Refined Oil103
5.6.1 Critical Control Points in Water Washing 105
5.6.2 Importance of Oil Quality Parameters of the
Refined and Water Washed Oil 106
5.6.3 Importance of Having Low FFA, Soap, and
Phosphorus in the Refined and Water Washed Oil 107
5.6.4 Comments on Chemical Refining Process 108
5.6.5 Troubleshooting Chemical Refining Process 109
5.7 Refining Loss109
5.7.1 Manual Checks on the Oil Loss 113
5.8 Short Mix Process114
5.8.1 Critical Control Points and Troubleshooting
Short Mix Process 116
5.9 Vacuum Drying116
5.9.1 Critical Process Control Points in Vacuum Drying 117
5.10 Soap Splitting for Recovering the Fatty Acids
(Acidulation of Soap Stock)118
viii Contents

5.11 Batch Acidulation Process119

5.11.1 Critical Control Points in Batch Acidulation Process 121
5.12 Continuous Acidulation Process121
5.13 Troubleshooting Acidulation Process123
5.14 Cold Chemical Refining Process for Sunflower Oil123
5.15 Modified Physical Refining Process125
5.15.1 Critical Control Points in Modified Physical
Refining Process 126
5.16 Modified Caustic Refining Process127
5.17 Semiphysical Refining Process128

6. Bleaching
6.1 Introduction129
6.2 General Operating Steps in Bleaching130
6.3 Dry Bleaching Versus Wet Bleaching131
6.4 Critical Control Points in Dry Bleaching133
6.5 Sampling Frequency in Bleaching Process142
6.6 Troubleshooting Dry Bleaching Process143
6.7 Wet Bleaching Process143
6.8 Critical Control Points in the Wet Bleaching Process146
6.9 Two-Step Bleaching Process (Use of Silica Hydrogel)147
6.9.1 Benefits of Two-Step Bleaching Process
(Use of Silica Hydrogel) 148
6.10 Critical Control Points in Two-Step Bleaching Process149
6.11 Packed Bed Filtration in Bleaching Process150
6.11.1 Oil Quality Checks 152
6.12 Critical Control Points in Packed Bed Bleaching153
6.13 Filters for Filtering Bleached Oil154
6.13.1 Plate and Frame Filters 154
6.13.2 Pressure Leaf Filters (Horizontal and Vertical Tanks) 156
6.14 Bleaching Agents159
6.15 Bleaching Very Green Canola Oil167
6.15.1 Critical Control Points 167
6.15.2 Bleaching of the Treated Oil 168
Reading References169

7. Hydrogenation
7.1 Introduction171
7.2 Historical Background of Hydrogenation171
7.3 Understanding the Process of Hydrogenation172
7.3.1 Effects of Hydrogenation 173
7.4 Hydrogenation Process175
7.4.1 Batch Hydrogenation Reactor 175
7.4.2 Operation of a Batch Hydrogenation Reactor 176
7.4.3 Adiabatic Reaction Process 177
7.4.4 Isothermal Process 177
7.4.5 Deadend-Type Hydrogenation Reactor 178
 Contents ix

7.4.6 Recirculating-Type Hydrogenation Reactor 179

7.4.7 Comparison Between the Deadend and the
Recirculating Types of Reactors 179
7.4.8 Continuous Hydrogenation Reactor 179
7.4.9 Applicability of a Continuous Hydrogenation Reactor 181
7.5 Critical Control Points in the Hydrogenation Process182
7.5.1 Catalyst Activity 182
7.5.2 Manifestations of a Poor-Activity Catalyst 182
7.5.3 Catalyst Selectivity 183
7.5.4 Hydrogen Gas Dispersion 189
7.5.5 Hydrogen Gas Venting From the Reactor 191
7.5.6 Hydrogen Gas Supply 191
7.5.7 Reaction Pressure 191
7.5.8 Reaction Temperature 192
7.5.9 Agitation 193
7.6 Catalyst Filtration193
7.7 Critical Quality Parameters in Batch Hydrogenation196
7.8 Trans Fatty Acids196
7.8.1 Manipulation of the Reactor Conditions 196
7.8.2 Higher Cost of the Reactor 201
7.8.3 Heating Hydrogenated Oil before Filtration 202
7.8.4 Larger-Filter Area or Dirt Load Capacity 202
7.8.5 Higher Cost of Depreciation 202
7.8.6 Higher Cost of Maintenance 202
7.8.7 Increased Cost of Catalyst 203
7.8.8 Higher Oil Loss in the Spent Catalyst 203
7.8.9 Cost of Spent Catalyst Disposal 203
7.9 Sources of Hydrogenation Catalysts207
7.10 Selection of Hydrogenation Catalyst207
7.10.1 Catalyst Activity 208
7.10.2 Selectivity 208
7.10.3 Filterability 208
7.10.4 Physical Integrity 208
7.10.5 Cost 208
7.11 Commercially Available Nickel Catalysts208
7.12 Troubleshooting the Hydrogenation Process209
7.13 Heat Recovery in Hydrogenation209
Reading References215

8. Deodorization
8.1 Introduction217
8.2 Purpose of Deodorization217
8.3 Description of the Deodorization Process218
8.4 Operating Principles of Deodorization219
8.4.1 Interpretation of the Previous Formula 219
8.5 Critical Control Points for the Deodorizing Process220
8.5.1 Incoming Oil Quality 220
x Contents

8.5.2 Deaeration of the Oil Before Heating

It for Deodorization 221
8.5.3 Heating the Oil for Deodorization 222
8.5.4 Operating Pressure (Vacuum) 222
8.5.5 Operating Temperature 223
8.5.6 Amount of Stripping Steam 223
8.5.7 Batch Size or Flow Rate 224
8.5.8 Citric Acid Addition 225
8.5.9 Cooling Deodorized Oil 225
8.6 Deodorized Oil Quality226
8.6.1 Physical Attributes 226
8.6.2 Chemical Attributes 226
8.6.3 Organoleptic Attribute—AOCS Method
Cg-2-83 (09) 226
8.6.4 Significance of the Deodorized Oil Quality
Standards226
8.7 Types of Deodorizers226
8.7.1 Batch Deodorizers 227
8.7.2 Typical Operating Steps in a Batch Deodorizer 230
8.7.3 Vacuum Sampler 231
8.7.4 Semicontinuous Deodorizer 232
8.7.5 Advantages of Semicontinuous Deodorizers 234
8.7.6 Continuous Deodorizers 235
8.7.7 Advantages of Continuous Deodorizers 237
8.7.8 Disadvantages 237
8.7.9 Residence Time Distribution in a Continuous
Deodorizer238
8.8 Vacuum System for Deodorizer241
8.9 Periodic Cleaning of the Deodorizer244
8.9.1 Batch Deodorizer 245
8.9.2 Semicontinuous Deodorizer 246
8.9.3 Continuous Deodorizer 246

9. Finished Product Storage and Handling

9.1 Introduction249
9.2 Transfer and Storage of Deodorized Products in Tanks249
9.3 Deodorized oil Storage Tank250
9.3.1 Components of the Deodorized Oil Storage Tank 250
9.3.2 Nitrogen Blanketing 251
9.3.3 Temperature Indicator Controller 254
9.3.4 Agitator 254
9.4 Loading Finished Oils in Trucks254
9.5 Unloading Finished Oil From Tank Trucks256
9.6 Packaged Products Stored in the Warehouse257
9.7 Maintaining Product Quality in the Warehouse259
9.7.1 Consumer Products 259
9.7.2 Industrial Products 260
9.8 Shipping of Packaged Products260
 Contents xi

10. Fundamentals of Fat Crystallization Related to

Making Plastic and Pourable Shortenings
10.1 Introduction261
10.2 Fat polymorphism262
10.2.1 Alpha Crystals 262
10.2.2 Beta Prime Crystals 262
10.2.3 Beta Crystals 263
10.2.4 Melting Points of the Three Polymorphic Phases 263
10.2.5 Crystal Packing Pattern of Alpha, Beta Prime,
and Beta Crystals 264
10.3 Triglyceride Structure264
10.3.1 Fatty Acid Distribution in Trisaturated Triglycerides
and Their Polymorphic Properties 264
10.3.2 Summary of the Rule of Thumb on the
Polymorphic Behavior of Triglyceride Molecules 267
10.4 Fat Crystallization267
10.4.1 Sequence of Events in Controlled Crystallization
Process268
10.4.2 Typical Crystallization Process for Making
Shortening269
10.4.3 Process Description 269
10.4.4 What Happens to the Product? 270
10.4.5 Primary and Secondary Crystal Bonds 270
10.4.6 Primary Bonds 271
10.4.7 Secondary Bonds 271
10.4.8 Utilizing the Properties of the Primary and the
Secondary Bonds 271
10.4.9 Factors Determining the Physical Properties of
Crystallized Fats 272
10.4.10 General Rules of Fat Crystallization 272
10.4.11 Critical Process Variables for Fat Crystallization 272
10.4.12 Discussions on the Crystallization Process 272
10.4.13 Establishment of Crystal Matrix 273
10.4.14 Purpose of Tempering 276
10.4.15 Comments on Tempering of Shortening Made
and Used at a Large Bakery 277
10.4.16 Tempering Procedure 277
10.4.17 Benefits of Tempering Shortening 278
10.5 Characterization of Fat Crystals280
10.5.1 Hardness 280
10.5.2 Consistency (Smoothness/Graininess) 281
10.5.3 Plasticity/Spreadability 281
10.5.4 Structure 282
10.5.5 Pourability 282
10.5.6 Polymorphic Phase 282
10.6 Palm Oil in Solid Shortening283
10.6.1 Improving Crystallization Rate in
Palm Oil Shortening 283
xii Contents

10.7 Issues With the Interesterified Products284

10.8 Very High–Hard Stock Content284
10.9 Pourable Liquid Shortening285
10.9.1 Product Description 285
10.9.2 Special Properties 285
10.9.3 Formulation 285
10.9.4 Polymorphic Phase 286
10.9.5 Processing Steps for Making Pourable
Liquid Shortening 287
10.9.6 Critical Control Points 287
10.9.7 Fluidity of the Shortening 289
Reading References289

11. Winterization and Fractionation of Selected

Vegetable Oils
11.1 Introduction291
11.2 Winterization of Sunflower Seed Oil292
11.2.1 Cold Test Versus the Wax Content of Sunflower Oil 293
11.3 Critical Process Variables for Winterization of Sunflower Oil294
11.4 Troubleshooting300
11.5 Winterization of Soybean Oil300
11.5.1 Process Description 300
11.5.2 Filtration 305
11.6 Fractionation of Palm Oil306
11.6.1 Suitability of Palm Oil for Fractionation 308
11.6.2 Methods for Fractionation 309
11.7 Dry Fractionation309
11.7.1 Precrystallizer 310
11.7.2 Crystallizer 310
11.7.3 Filtration 311
11.7.4 Critical Control Points in Dry Fractionation 312
11.7.5 Initial Oil Temperature 312
11.7.6 Precrystallization 312
11.7.7 Cooling Rate 313
11.7.8 Holding Time in the Crystallizer 313
11.7.9 Agitation in the Crystallizer 313
11.7.10 Final Crystallizer Temperature 314
11.7.11 Filtration 314
11.8 Troubleshooting Dry Fractionation314
11.9 Multiple Dry Fractionation315
11.9.1 Benefits of Multiple Dry Fractionation of Palm Oil 317
11.10 Wet Fractionation with Detergent (Lanza Process)318
11.11 Solvent Fractionation Process319
11.11.1 Critical Control Points 321
11.11.2 Comparison Between the Three Methods
of Fractionation 321
Reading References322
 Contents xiii

12. Insight to Oil Quality Management

12.1 Introduction323
12.2 Managing Oil Quality323
12.2.1 Step #1: Have a Clear Product Objective 324
12.2.2 Step #2: Have the Right Capability in Place 324
12.2.3 Step#3: Measurements of Quality and Setting
Standards325
12.2.4 Step #4: Measurement of Performance 325
12.2.5 Step #5: Understand the Behavior of the Oil and
Learn How to Protect It From Degradation 325
12.3 Modes of Oil Decomposition326
12.4 Areas in Oil Quality Management328
12.5 Summary of Oil Quality Standards339
Reading References340

13. Trans Fat Alternatives and Challenges

13.1 Introduction341
13.1.1 Pioneering by Europe 341
13.1.2 Trans Fat Regulation in the United States 341
13.1.3 Trans Fat in the United States Diet and the Sources 341
13.1.4 Subsequent Developments in FDA Regulations
on Trans Fat 342
13.1.5 Trans Fat Regulation in Canada 344
13.2 Nutritional Labeling Regulation345
13.2.1 Trans Fat Claims 345
13.2.2 Nutrition Labeling Regulation 346
13.2.3 For 30-g Serving 346
13.2.4 For 10-mL (9.2-g) Serving 346
13.2.5 Influence of Trans Fats 347
13.3 Source of Trans Fatty Acids348
13.4 Technical alternatives available today349
13.4.1 Technical Solutions for Trans Fat Reduction 349
13.4.2 Hydrogenation Under Special Conditions 349
13.4.3 Use of Platinum Catalyst 349
13.4.4 Interesterification 350
13.4.5 Modified Composition Oils 351
13.4.6 Use of Pourable Shortening 354
13.5 Challenges354
13.5.1 Challenge #1: Getting Stable Liquid Oil in an
Adequate Supply 355
13.5.2 Challenge #2: Supplies of Modified Composition
Seed Oils 355
13.5.3 Challenge #3: Consumer Advocates in the United States 355
13.5.4 Challenge #4: Use of Regular Soybean Oil is
Reducing Shelf Life Stability of the Transesterified
Shortening in Some Applications 356
13.5.5 Challenge #5: Economic Challenge 356
xiv Contents

13.6 Interesterification Process357

13.6.1 Chemical Process 357
13.6.2 Enzymatic Process 358
13.7 Chemical Interesterification Process358
13.7.1 Description of a Chemical Interesterification Process 358
13.7.2 Reaction Mixture 358
13.7.3 Reaction Steps 359
13.7.4 Critical Control Points in the Chemical
Interesterification Process 360
13.7.5 Questions Related to Chemical Interesterification 364
13.8 Enzymatic Interesterification Process367
13.8.1 Introduction 367
13.8.2 Catalyst 367
13.8.3 Purpose of Immobilization of the Enzyme 367
13.8.4 Reaction Steps in Enzymatic Interesterification Process 367
13.8.5 Pretreatment 368
13.8.6 Lipase Interesterification 368
13.8.7 Batch Process 369
13.8.8 Continuous Multiple Fixed Bed Process 369
13.8.9 Single Fixed Bed Continuous Process 370
13.8.10 Enzyme Activity 370
13.8.11 Productivity 370
13.8.12 Deodorization 371
13.9 Comparison Between the Chemical and the Enzymatic
Interesterification Processes371
Reading References374

14. Familiarization With Process Equipment

14.1 Introduction375
14.2 Processing Equipment and Accessories376
14.2.1 Process Equipment 376
14.2.2 Process Accessories 376
14.2.3 Process Instruments 377
14.2.4 Process Equipment 377
14.2.5 Comments on the Atmospheric Vent 379
14.2.6 Designs for Common Oil Storage Tanks 379
14.2.7 Process Supervisor’s Responsibility Regarding the Tanks 381
14.2.8 Process Accessories 394
14.2.9 Troubleshooting Ejectors 398
14.2.10 Freeze-Condensing Vacuum System 398
14.2.11 Agitators 400
14.2.12 Types of Mixers Used in an Oil Processing Plant 401
14.2.13 Design Considerations for Selecting an Agitator 401
14.2.14 Pumps 402
14.2.15 Valves 406
14.2.16 Cooling Towers 406
14.2.17 Motors, Starters, Switches, Fans, and Blowers 410
14.2.18 Compressors 411
 Contents xv

14.2.19 Air Dryers 412

14.2.20 Steam Tracing 413
14.2.21 Steam Traps 414
14.2.22 Steam Purifier 419
14.2.23 Seals 419
14.2.24 Process Instruments 420

15. Loss Management

15.1 Introduction423
15.2 Definition of Losses424
15.2.1 Degrading and Variations 424
15.3 Factors Contributing to High Plant Losses in
Degrading and Variations425
15.4 Elements of Good Loss Management430
15.5 Guidelines for Managing D&V431
15.5.1 Step 1: Identify all Material Flows at the Plant 432
15.5.2 Step 2: Identify Key Loss Points 432
15.5.3 Return from Sales 436
15.5.4 Dump 436
15.5.5 Step 3: Determine the Causes for the Losses at
Each Location 437
15.5.6 Step 4: Define Solutions to Prevent Losses 437
15.5.7 Step 5: Define Goals 437
15.5.8 Step 6: Set Priorities for the Improvement Activity 437
15.5.9 Step 7: Define Action Steps, Target Dates,
Milestones, the Success Criteria, and the
Method Used for Measuring Progress 438
15.6 Managing Plant Losses438
15.6.1 Known Losses 438
15.6.2 Unknown Losses 439
15.6.3 Key for Successful Loss Management 439
15.7 Final Comments on Loss Management440
15.8 Samples of Forms Helpful for Tracking Variations440

16. Plant Safety Procedures

16.1 Introduction445
16.2 Plant Safety446
16.2.1 General 446
16.3 Safety Agencies446
16.3.1 Occupational Safety and Health Administration 446
16.3.2 American National Standards Institute 447
16.3.3 National Institute for Occupational Safety and Health 447
16.3.4 The National Fire Protection Association 447
16.3.5 Workplace Hazardous Materials Information System 448
16.4 Areas of Safety Training Required at the Plant448
16.4.1 Fire and Explosion Safety 448
16.4.2 Selection of Fire Extinguishers 449
xvi Contents

16.4.3 Hazards of Dry Chemical Extinguishers 450

16.4.4 Compressed Gas Safety 450
16.4.5 Recommended Procedure for the Preparation
for Welding or Hot Work (Using Gas Torch for
Metal Cutting) 450
16.4.6 Chemical Safety 451
16.4.7 Significance of the Color Code and the Numbers
for the Chemicals and the Degree of Hazard 452
16.4.8 Improper Storage of Solvents 454
16.4.9 Electrical Safety 454
16.4.10 Confined Space Entry Procedure 455
16.4.11 The Tank Entry Permit Must be Filled out and
Signed by Two Persons 459
16.4.12 Entering the Tank 459
16.5 Special Notes460

17. Regulatory Agencies and Their Roles in a

Vegetable Oil Plant
17.1 Introduction463
17.2 Agencies Overseeing Food Industry463
17.2.1 United States 463
17.2.2 Europe 464
17.3 Environmental Protection Agency465
17.3.1 Role of EPA in a Food Plant 465
17.4 National Fire Protection Association466
17.4.1 NFPA’s Role in an Oil Plant 466
17.5 US Department of Agriculture466
17.6 Role of USDA at an Edible Oil Plant467
17.7 US Food and Drug Administration467
17.8 Rabbinical Assembly469
17.8.1 Meat 470
17.8.2 Dairy 470
17.8.3 Pareve 470
17.9 Role of Rabbinical Assembly in an Oil Plant470
17.10 National Institute of Oilseed Products471
17.11 National Oilseed Processors Association471
17.12 Federation of Oils, Seeds and Fats Associations472
17.13 FEDIOL473
17.14 European Food Safety Authority473
17.15 Food Safety Authority474
17.16 Rapid Alert System for Food and Feed475

Index477
Preface

It was my desire to introduce the second edition of the book because of the
introduction of certain newer techniques in vegetable oil processing. These are
discussed in various chapters in this book.
The first edition of this book was received well by the readers. Many readers
asked when the second edition of the book would be published. I also received
requests from readers to include the processing practices for palm oil, coconut
oil, cottonseed oil, and sesame seed oil, as these are important vegetable oils.
Unfortunately, it was not possible to do so. The reason for their exclusion is that
the basic principles and practices described in this book do apply to most veg-
etable oil processing operations. Additionally, the volume of information would
have been too large to be included a single book.
Vegetable oil processing is an essential part of the food industry. Current
unit operations have been developed over many years by processors and equip-
ment manufacturers, with the assistance of universities and federal laboratories.
Public universities have changed over time, resulting in the current emphasis
on programs that meet the prevailing business needs. In today’s market, the
vegetable oil processing industry does not offer enough jobs to warrant a more
detailed training of future technical personnel. The size of oil processing pro-
grams, where they exist at all, depends on local initiatives in attracting and
maintaining sufficient numbers of students and external funding of research.
For this reason, Texas A&M University, Cornell University, Purdue University,
Iowa State University, University of Illinois, University of Florida, and Ohio
State University are among the few exceptions, although most of these institu-
tions have much stronger Food Technology and Food Engineering curriculum
than programs on fats and oils.
The majority of these graduating students prefer food manufactures because
of job availability, while only a few find employment in the vegetable oil refin-
ing industry.
Pioneers in the vegetable oil processing industry in the United States were
Durkee, Procter & Gamble, Anderson Clayton, Hunt Wesson, Humko, Unilever,
A.E. Staley Co., and Corn Products Co. These companies were very strong in
their research and development activity. They maintained product and process
development activities that trained fresh university graduates in chemistry
and chemical engineering in processing and applications of vegetable oils and
animal fats.

xvii
xviii Preface

The oil companies in the United States were mostly stand-alone refiners,
that is, they purchased crude oils from the crushers and processed them to make
various products. They had their own pilot plants that facilitated the training
programs in the area of oil processing. The fresh recruits could get hands-on
experience in oil processing and product formulation. This was done primarily
through project assignments to the newcomers. Some of these companies also
had well-established training programs to provide the necessary tools to their
technical recruits in oil processing and product formulation.
Numerous changes have taken place in the oil-processing industry in the
United States since the 1970s:
1. The oil crushers, such as Archer Daniels & Midland Co., Cargill Co., and
Bunge Corporation realized that it was more profitable to integrate their
crushing operation with the refinery. They started to refine their own oil,
in addition to selling the crude oil to the stand-alone refiners. They soon
entered the market with packaged fats and oils products initially through
acquisitions and later by building their own facilities. They expanded their
R&D capabilities and now have become well established in the area where
many stand-alone refiners filled the industry needs.
2. Oil prices soared in the mid-1970s during the Middle East oil embargo,
causing a serious blow to the stand-alone refiners.
3. The stand-alone refiners started to see declining profit margins on their
products because they could not match the production and reduced cost of
production of the integrated crusher refiners.
4. As the competition grew from the crusher refiners, the R&D activity in the
stand-alone refineries declined seriously due to lack of funds.
5. Some of these stand-alone refiners started to provide copacking services
to the crusher refiners as they entered the consumer product market. Soon,
some of these companies were bought out by the crusher refiners and sub-
sequently either upgraded or disbanded.
6. Eventually, many of the stand-alone refiners either closed down or were
bought out by the crusher refiners or other food companies.
7. Some of the stand-alone refiners switched their product lines to go into a
niche market where the large crusher refiners were not competing.
8. Initially the crusher refiners were not up to speed with the R&D work.
9. The oil-processing equipment manufacturers picked up the slack and start-
ed to offer the technology needed for the oil refineries.
10. During this period the USDA laboratories remained active in the oil re-
search field.
11. Universities, such as Texas A&M and Iowa State University, became active
in providing pilot plant services to the oil industry.
12. Independent facilities, such as the POS pilot plant in Canada, became avail-
able as a source of basic, as well as applied research work in fats and oils.
13. A.C. Humko of Memphis, Tennessee, United States, offered pilot plant
services to the oil companies.
 Preface xix

These changes in the vegetable oil industry essentially eliminated opportuni-

ties for on-the-job training of fresh college graduates in fats and oils technology
in the manner that was possible prior to 1970. Very few individuals from that era
are still working for major oil refiners. A few are working as consultants, but a
great majority of them have either retired or are deceased.
I am probably one of the few fortunate ones who received training in fats
and oils at Procter & Gamble Co. and am still around to talk about my expe-
rience. The company hired fresh engineering graduates from the universities.
Every new engineer hired received training through the assignment of projects.
The new recruit had to go through the following steps:
1. The engineer was assigned a project.
2. The engineer prepared a project proposal that contained the following
elements:
a. project objective,
b. experimental plan,
c. data to be collected,
d. analytical and product testing to be performed,
e. duration of the project,
f. list of all internal resources, and
g. list of all internal R&D reports on related topics.
3. The proposal had to be approved by the immediate supervisor and the
Director.
4. At the end of the project the engineer had to write a formal report that had to
be approved by the Director.
5. A copy of the report was kept in the company archive for future reference.
6. The project could then be officially closed.
7. If the product required any plant trial, a completely new proposal had to be
initiated by the engineer with all pertinent information of cost, besides the
objective.
8. The product performance had to be proven through several tests, such as
market sample data collection and analysis, customer complaint data, prod-
uct storage study, and consumer tests.
9. At the end of the study another report had to be prepared, approved, and
archived as before.
I am not aware of such a rigorous training program that might be available
anywhere today.
In this book, I will make my best effort to explain why certain processing
steps are considered necessary. I will also provide adequate theoretical explana-
tions to the readers so they can appreciate the significance of the steps taken in a
vegetable oil processing. It might not be possible to cover every detail or I might
even leave certain material out of this book to protect any proprietary informa-
tion that I have gathered during my tenure at various companies. I believe that
the readers will find the information provided in this book to be useful.
xx Preface

In recognition, I would like to express my appreciation to Late Robert L.

Wille and Cornelius Japikse, my original mentors at Procter & Gamble Co., for
training me during the early days of my career. I also am indebted to Late Walter
E. Farr and the Late Dr. Thomas H. Smouse for their support in advancing my
career in oil processing and applications at Anderson Clayton Co. My sincere
appreciation also goes to my wife, Mina Gupta, for her untiring encouragement
to write this book. I also wish to express my sincere gratitude to the reviewers
of the various chapters of this book in spite of their busy schedules.
Finally, a trend is developing in the area of technical communication, which
serves as a reminder that we must all be critical thinkers. There are some trade
journals, as well as some technical journals, that now publish editorial reviews
of scientific and technical issues written by the editors or the assistant editors,
who gather information and compile a presentation. While the information has
been gathered through speaking with experts in the field, and references are
clearly made to the persons providing the information, there are times when
this information is not absolutely accurate. Although I am sure no publication
intentionally publishes erroneous information, it runs the risk of misleading or
confusing less-experienced readers. In my opinion, we should look carefully at
once again relying on experts in the field to provide not only original research
but also these critical reviews to ensure we are providing a solid scientific foun-
dation for readers.
Chapter 1

Requirement for Successful

Production and Delivery
of the Refined Vegetable Oils

Vegetable oils are refined with care so the resulting oils as well as the products
formulated with the oils are of high quality.
In the rest of the book the various processing steps, their operating condi-
tions, corrective actions through troubleshooting, etc. have been discussed for
the reader. All of the processing conditions described are to assist the oil proces-
sors to understand the principles of oil processing and produce the best quality
refined oil at the plant.
It must be stressed that even after using the guidelines provided in this book,
one may not be able to produce the best quality refined oil if the incoming crude
oil is not of high quality. It may sound strange, but the success of obtaining
the highest quality finished oil depends greatly on the quality of the crude oil
received at the refinery.

1.1 CRUDE OIL

Crude oil quality can vary and it depends on various factors that are not directly
under the control of the oil refiner. Poor quality crude oil creates certain dif-
ficulties in the refining process along with the oil quality issues. Several tips to
procure the highest quality crude oil are discussed in this chapter so the refiner
is aware of these factors and can take certain actions in the refinery to minimize
the negative impact of some of these factors.

1.2 OILSEEDS
As mentioned earlier, good quality of the refined oil starts with the high quality
oilseeds or oil-bearing fruits and nuts. The quality of the crude oil depends on
various factors, such as:
l maturity of the oilseeds,
l harvest conditions (excessive rain or drought condition before harvest),
l handling of seeds,
Practical Guide to Vegetable Oil Processing. http://dx.doi.org/10.1016/B978-1-63067-050-4.00001-5
Copyright © 2017 AOCS Press. Published by Elsevier Inc. All rights reserved. 1
2 Practical Guide to Vegetable Oil Processing

l seed storage conditions, and

l insect infestation of the seeds.
(In the subsequent discussions only oilseeds will be mentioned. Fruit palm
and oil-bearing nuts will be discussed separately.)

1.2.1 Maturity
Immature soybean seeds can exhibit various deficiencies. The crude oil may
exhibit some different fatty acid profile and also some variations in the other
components in the seeds. This may slightly impact the processing conditions
and performance of the refined oil in certain applications. There are numerous
literature references that indicate the following:
l The immature seeds tend to have lower lipoxygenase activity, trypsin inhibi-
tor, and urease activity compared to the mature seeds.
l The immature seeds tend to have higher contents of FFA (free fatty acids)
and chlorophylls compared to the mature seeds.
l Oil content and total protein contents are not very different between the
immature and mature seeds.
l There are minor differences in some individual protein contents between the
immature and mature seeds.
Therefore, the oil refiner may receive crude soybean oil that contains high
chlorophyll because of immature soybeans. This will require some addition-
al degumming and bleaching steps. This will be discussed in the chapter on
bleaching.

1.2.2 Harvest Condition

1.2.2.1 Wet Harvest Condition
Soybean, sunflower, cottonseed, and canola crude oils can exhibit higher than
normal green color when the seeds are harvested before they reach maturity or
the harvesting season is too wet. The crude oils will require extra steps to remove
the excess chlorophylls from them in the degumming and bleaching steps. The
refined oil may have lower stability if these steps are not followed properly.

1.2.2.2 Dry Harvest Condition

Dry harvest condition due to droughts can cause physical damage to the seeds
resulting in higher than normal FFA and oxidation in the crude oil. The oil will
exhibit lower than normal stability.

1.2.3 Handling of Seeds

The seeds, if damaged, during harvest and transport and storage, the crude
oil can develop higher FFA and exhibit higher oxidation. This oil will require
 Requirement for Successful Production and Delivery Chapter | 1 3

extra steps in the refining process and will typically exhibit lower stability than
normal.
The seeds are dried to <10% moisture before storage. The drying condition
requires controlled air temperature and flow around the seeds during the dry-
ing step. The seeds may develop case hardening if the air temperature is higher
and or the airflow rate is higher than normal. This can develop surface cracks
in subsequent handling of the seeds and the crude oil will exhibit higher than
normal FFA and initial oxidation.

1.2.4 Seed Storage

It is important that the seeds are properly dried to <10% moisture and stored
under 40°C (104°F) with proper air ventilation. At temperature of 45°C (114°F)
or moisture content of 14% or higher, the oilseeds develop higher concentration
of nonhydratable phospholipids. This makes degumming, refining, and bleach-
ing processes more difficult and it also results in higher refining loss and also
the refined oil quality is compromised. In addition, there is color fixation of the
oil. The crude oil develops darker than normal color that cannot be reduced
through the normal bleaching process. The crude oil in most cases has to be
treated with stronger alkali solution to reduce the color.

1.2.5 Insect Infestation

Typically, dry growing season and drought condition tend to promote insect
damage of the seeds. This results in higher than normal FFA and initial oxida-
tion in the crude oil. As described in some of the previous conditions, the crude
oil exhibits higher than normal refining loss and lower stability of the oil.

1.3 ADDITIONAL COMMENTS ON OILSEEDS

Oilseeds mature at a slight different rate between the top and lower parts of the
plant. This tends to be more pronounced in case of cottonseed. Similarly the
soybean pods can have different degree of maturity on the same plant and not
all the seeds on the same sunflower would be identical in maturity. Therefore, a
lot of oilseeds shipment may contain some seeds that are somewhat less mature.
The oilseeds in a lot will always have some damaged (broken) seeds, some
with lesser degree of maturity. However, the various grades of seeds that are
sold under USDA specification seem to perform in a uniform manner in produc-
ing the crude oil of desired quality.
Higher than normal level of diglycerides are formed whenever the crude
oil is treated with stronger than the normal strength of alkali solution used in
the process. Sometimes the crude oil is alkali treated more than once to meet
the refined oil specification on FFA and/or color. The excess alkali or stronger
alkali can attack the neutral triglyceride molecules in the oil (in addition to the
4 Practical Guide to Vegetable Oil Processing

FFA), forming diglycerides. Diglycerides are emulsifiers. High concentration

of diglycerides in the alkali treated oil makes it difficult to separate the aqueous
phase from the oil phase in the soap separation stage. This tends to increase
the loss of neutral oil in the soap causing higher oil loss in the refining process.

1.4 FRUIT PALM

The fruit palm is harvested from the tree when they reach maturity. Like in case
of oilseeds, the fruit palm on the same bunch may have somewhat different de-
gree of maturity. Usually, the very ripe ones get damaged or ruptured under the
normal harvesting procedure.
Lipase and lipoxygenase activity begin in the oil inside the fruit palm when
the skin of the fruit is damaged. The fruit is treated for enzyme deactivation and
the oil is extracted as soon as possible after the harvest. However, most com-
mercial crude palm oil (CPO) contains as much as 5% FFA and the diglycerides
content is typically 5%.
Whenever a molecule of FFA is formed from hydrolysis of a neutral triglyc-
eride molecule, a diglyceride molecule is formed. When the palm fruit is dam-
aged during harvest, the enzyme lipase hydrolyzes the triglyceride molecule
forming FFA and diglyceride.
The author studied the damaged fruit palm and the impact on the FFA of the
oil in a palm plantation in Costa Rica. Following tests were performed:
1. The damaged fruits from a fruit bunch were collected and weighed.
2. The total weight of the fruit palm in the bunch was taken.
3. It was found that the ruptured and damaged fruit constituted 6% of the total
weight of the fruit in the bunch.
4. FFA content in the oil extracted from the damaged fruit was found to be 50%.
5. Therefore, it was estimated that whatever the FFA of the oil from the fruit
palm extracted from the whole bunch would be increased by 3% (0.06 ×
50 = 3.0).
6. Thus, the majority of the FFA in CPO would have come from the over ripe
and damaged fruit.
Typical commercial production of CPO does not separate the damaged fruit
from the rest for oil extraction.
There are companies, such as Sime Darby Jomalina that do separate the
damaged fruit before extraction in order to produce low FFA and low diglyc-
eride CPO and refined PO and palmolein. Sime Darby Jomalina can deliver
palm oil and palm oil fractions with guaranteed quality (JGQ). There are other
companies in Malaysia that are also capable of delivering low FFA and low
diglyceride palm oil if a customer needs it.
High diglyceride content in the palm oil increases the FFA in a fryer faster
and also slows down the rate of crystal formation in the shortening and marga-
rine process.
 Requirement for Successful Production and Delivery Chapter | 1 5

1.5 GROUNDNUTS (PEANUTS) AND TREE NUTS

The same comments made in connection with the oilseeds also apply for these
oil-bearing nuts. An important additional issue that can be experienced with
nuts is mold that can produce aflatoxins. Aflatoxin is a type of mycotoxin pro-
duced by Aspergillus molds. Aflatoxins are very toxic and highly carcinogenic.
There are three different types of aflatoxins that can be found in food. Short-
term heavy ingestion of the toxins can cause even death. Long-term exposure
can cause growth impairment and liver cancer. Aspergillus molds grow mostly
on crops, such as grains and nuts. Under the right conditions, Aspergillus often
grows on grain before it is harvested. But it can also grow on harvested grain if
the grain is stored damp.
This is why nuts should be analyzed for aflatoxins in addition to the other
tests that are normally done for accepting the raw material for crushing.

1.6 CRUDE OIL HANDLING, STORAGE, AND TRANSPORT

Most solvent extraction plants that produce crude oil do not cool and filter the
crude oil after desolventization. This causes oxidation in the oil. In addition,
if the crude oil is stored for extended period, it undergoes oxidation and a few
other reactions that are discussed later in the book. These reactions degrade
the quality of the crude oil, which, in turn, increases difficulty in refining and
produces less than desirable quality in the refined oil. Excessive aeration of
the crude oil during loading and transportation can increase oxidation of the
crude oil.
Crude oil should be refined soon after it is made. Crude oil, if stored before
refining, should be done at <40°C (104°F) for seed oils. Palm oil should be
stored <50°C and preferably <45°C. Higher storage temperature causes oxida-
tion to the crude oil. In addition, the FFA can rise, the color darkens and it can
even have color fixation. The PV value goes up with higher storage temperature
and longer time of storage. The PV breaks down during the refining process
but the anisidine value (AV) goes up. PV measures the primary oxidative state
for the oil. AV indicates the degree of the secondary oxidation state of the oil.
Crude oil with higher AV indicates prior exposure of the crude oil to oxygen.
This results in refined oil that would oxidize rapidly when heated (principally in
frying and baking applications).

1.7 CONCLUDING REMARKS

It should be clear from the previous discussions that the quality of the crude oil
is of utmost importance in obtaining good quality refined oil because all of the
reactions discussed here negatively impact the refined oil quality as well as the
products formulated with the refined oil.
Page left intentionally blank
Chapter 2

Basic Oil Chemistry

Man has used vegetable oils for centuries. Oil bearing nuts and animal fats were
consumed as sources of energy long before nutrition concepts were envisioned.
Oils also were used early for lighting, as medicines, as cosmetics in religious
ceremonies, and applied to weapons and utensils. The ancient oils of the Middle
East, sesame and olive, were valued because of their long stability. Sunflower
was cultivated in the Arizona–New Mexico area before the time of Christ, and
seeds from the Missouri–Mississippi river basins were among the early plants
transposed to Europe by explorers. Invention of the cotton gin in the late 1700s
led to a major cotton export trade in the United States in the early 1800s, and
to development of cottonseed oil as the first new oil of the Industrial Age in the
mid-1800s. The continuous screw press, and early methods of caustic refining,
bleaching, deodorization, winterization, and hydrogenation, including develop-
ment of the first all vegetable shortening “Crisco” (shortened name for crystal-
lized cottonseed oil) are among innovations developed. Processing of soybean,
a crop first developed in China, led to further oil industry innovations including
development of continuous solvent extractors and steam distillation technolo-
gies to reduce or remove the original raw flavor in the crude oil were developed
in the mid-1900s. As flavor and stability improved, man expanded use of oils
to: (1) cooking, (2) frying, (3) baking shortenings, (4) salad dressings, (5) food
lubricants (like release agents in baking and candy making processes), (6) flavor
carriers, and (7) dust-control agents. Each of the application requires oils with
specific physical and chemical properties.
Other oils, such as palm oil, regular canola oil, high oleic and low linolenic
canola oil, high oleic sunflower oil, high oleic safflower oil, and so on were all
commercialized much later than the animal fat and cottonseed oil.

2.1 COMPOSITION OF OIL

All of the world’s matter is composed from approximately 108 elements. The
smallest divisible stable particle of an element is called an “atom.” Compounds
consist of atoms of two or more elements, with the smallest divisible stable
particle called a “molecule.” Carbon (C), hydrogen (H), and oxygen (O) atoms
are the principal building blocks of fats and oils.

Practical Guide to Vegetable Oil Processing. http://dx.doi.org/10.1016/B978-1-63067-050-4.00002-7

Copyright © 2017 AOCS Press. Published by Elsevier Inc. All rights reserved. 7
8 Practical Guide to Vegetable Oil Processing

FIGURE 2.1 Formation of triglycerides.

Often, it is desirable to pictorially indicate relative positions of the ele-

ments in molecular structures. But, these must be carefully drawn by estab-
lished convention, since the world exists in three dimensions, but only two
dimensions are available for presentation on paper. In making such draw-
ings, the knowledgeable chemist recognizes that some atoms only associate
with others by extending links, while others only accept links. For example,
each oxygen atom extends two links, while, each hydrogen atom accepts only
one link. The chemistry of fats and oils is carbon chemistry, also known as
“organic chemistry.” The carbon atom is unique in that it can either extend or
accept a total of four links, with link givers, link receivers, or even with other
carbon atoms.
Oil is a mixture of 96–98% fatty acid triacylglycerols (commonly referred
to as “triglycerides”), with the balance consisting of other fat-dispersible or fat-
soluble compounds. Triglycerides consist of three fatty acids, which are sub-
stituted in the hydroxyl (alcoholic) sites of a glycerin (glycerol) backbone. The
construction of a simple triglyceride is shown in Fig. 2.1, where each fatty acid
is represented as a different “R.”
Depending on the extent to which the three former hydroxyl groups of glyc-
erol are replaced with fatty acids, the resulting compounds are known as follows.
Monoglycerides are formed when one of the three hydroxyl groups of glycerol is replaced
by a fatty acid.
Diglycerides are formed when two of the three hydroxyl groups of glycerol are replaced by
the same or different fatty acids.
Triglycerides are formed when all three of the hydroxyl groups of glycerol are replaced by
fatty acids (also referred as neutral oil).
A molecule of water is formed each time a fatty acid molecule replaces a
hydroxyl group. Fig. 2.2 further shows the structures of monoglyceride, diglyc-
eride, and triglyceride molecules.
The major objective in refining and processing is to convert a shipment of
purchased crude oil into the maximum possible amount of saleable “neutral oil”
(triglycerides). Monoglycerides and diglycerides are formed when the neutral
oil reacts with water molecules under undesirable storage and handling condi-
tions. This reduces the yield of neutral oil in the refining process. It also creates
poor quality refined oil. This will be discussed further in Chapter 11.
Another random document with
no related content on Scribd:
otra alguna,
ueys vna perfeçion jamas
oyda,
ueys una discreçion, qual fue
ninguna,
de hermosura y graçia
guarnescida?
¿ueys la que está domando a
la fortuna
y a su pesar la tiene alli
rendida?
la gran doña Leonor Manuel
se llama,
de Lusitania luz que al orbe
inflama.
Doña Luisa Carrillo, que en
España
la sangre de Mendoça ha
esclareçido:
de cuya hermosura y graçia
extraña,
el mismo amor, de amor está
uençido,
es la que a nuestra Dea ansi
acompaña
que de la uista nunca la ha
perdido:
de honestas y hermosas claro
exemplo,
espejo y clara luz de nuestro
templo.
¿Ueys una perfeçion tan
acabada
de quien la misma fama está
embidiosa?
¿ueys una hermosura más
fundada
en graçia y discreçion que en
otra cosa,
que con razon obliga a ser
amada
porque es lo menos de ella el
ser hermosa?
es doña Eufrasia de Guzman
su nombre,
digna de inmortal fama y gran
renombre.
Aquella hermosura
peregrina
no uista en otra alguna sino en
ella,
que a qualquier seso apremia
y desatina,
y no hay poder de amor que
apremie el della,
de carmesí uestida y muy más
fina
de su rostro el color que no el
de aquella,
doña Maria de Aragon se
llama,
en quien se ocupará de oy
más la fama.
¿Sabeys quién es aquella
que señala
Diana, y nos la muestra con la
mano,
que en graçia y discreçion a
ella yguala,
y sobrepuja a todo ingenio
humano,
y aun ygualarla en arte, en ser
y en gala,
sería (segun es) trabajo en
uano?
doña Ysabel Manrique y de
Padilla,
que al fiero Marte uenze y
marauilla.
Doña Maria Manuel y doña
Ioana
Osorio, son las dos que estays
mirando
cuya hermosura y graçia sobre
humana,
al mismo Amor de amor está
matando:
y esta nuestra gran Dea muy
vfana,
de ueer a tales dos de nuestro
uando,
loallas, segun son es
escusado:
la fama y la razon ternan
cuydado.
Aquellas dos hermanas tan
nombradas
cada una es una sola y sin
segundo,
su hermosura y graçias
extremadas,
son oy en dia un sol que
alumbra el mundo,
al biuo me paresçen
trasladadas,
de la que a buscar fuy hasta el
profundo:
doña Beatriz Sarmiento y
Castro es una
con la hermosa hermana qual
ninguna.
 El claro sol que ueys
resplandeçiendo
y acá, y allá sus rayos ya
mostrando,
la que del mal de amor se está
riendo,
del arco, aljaua y flechas no
curando,
cuyo diurno rostro está
diziendo,
muy más que yo sabré dezir
loando,
doña Ioana es de Çarate, en
quien vemos
de hermosura y graçia los
extremos.
Doña Anna Osorio y Castro
está cabe ella
de gran valor y graçia
acompañada,
ni dexa entre las bellas de ser
bella,
ni en toda perfeçion muy
señalada,
mas su infelize hado vsó con
ella
de una crueldad no vista ni
pensada,
porque al ualor, linaje y
hermosura
no fuesse ygual la suerte, y la
uentura.
Aquella hermosura
guarnecida
de honestidad, y graçia sobre
humana,
que con razon y causa fue
escogida
por honra y prez del templo de
Diana,
contino uençedora, y no
uençida
su nombre (o Nimphas) es
doña Iuliana,
de aquel gran Duque nieta y
Condestable,
de quien yo callaré, la fama
hable[1256].
Mirad de la otra parte la
hermosura
de las illustres damas de
Valençia,
a quien mi pluma ya de oy
mas procura
perpetuar su fama y su
excelençia:
aqui, fuente Helicona, el agua
pura
otorga, y tú, Minerua, enpresta
sçiençia,
para saber dezir quién son
aquellas
que no hay cosa que ver
despues de vellas.
Las cuatro estrellas ved
resplandesçientes
de quien la fama tal ualor
pregona
de tres insignes reynos
desçendientes,
y de la antigua casa de
Cardona,
de la vna parte Duques
exçelentes,
de otra el trono, el sçeptro, y la
corona,
del de Segorbe hijas, cuya
fama
del Borea al Austro, al Euro se
derrama.
La luz del orbe con la flor de
España,
el fin de la beldad y
hermosura,
el coraçon real que le
acompaña,
el ser, valor, bondad sobre
natura,
aquel mirar que en verlo
desengaña,
de no poder llegar alli criatura:
doña Anna de Aragon se
nombra y llama,
a do por el amor, cansó la
fama.
Doña Beatrix su hermana
junto della
vereys, si tanta luz podeys
miralla:
quien no podré alabar, es sola
ella,
pues no ay podello hazer, sin
agrauialla:
a aquel pintor que tanto hizo
en ella,
le queda el cargo de poder
loalla,
que a do no llega
entendimiento humano
llegar mi flaco ingenio, es muy
en vano.
 Doña Françisca d'Aragon
quisiera
mostraros, pero siempre está
escondida:
su vista soberana es de
manera,
que a nadie que la vee dexa
con vida:
por esso no paresçe. ¡Oh
quién pudiera
mostraros esta luz, que al
mundo oluida,
porque el pintor que tanto hizo
en ella,
los passos le atajó de
meresçella.
A doña Madalena estays
mirando
hermana de las tres que os he
mostrado,
miralda bien, uereys que está
robando
a quien la mira, y biue
descuydado:
su grande hermosura
amenazando
está, y el fiero amor el arco
armado,
porque no pueda nadie, ni aun
miralla,
que no le rinda o mate sin
batalla.
Aquellos dos luzeros que a
porfia
acá, y allá sus rayos uan
mostrando,
y a la exçelente casa de
Gandia,
por tan insigne y alta
señalando,
su hermosura y suerte sube oy
dia
muy más que nadie sube
imaginando:
¿quién uee tal Margareta y
Madalena,
que tema del amor la horrible
pena?
Quereys, hermosas
Nimphas, uer la cosa,
que el seso más admira y
desatina?
mirá una Nimplia más que el
sol hermosa,
pues quién es ella, o él jamas
se atina:
el nombre desta fenix tán
famosa,
es en Valençia doña Cathalina
Milan, y en todo el mundo es
oy llamada
la más discreta, hermosa y
señalada.
Alçad los ojos, y vereis de
frente
del caudaloso rio y su ribera,
peynando sus cabellos, la
exçelente
doña Maria Pexon y
Çanoguera
cuya hermosura y gracia es
euidente,
y en discreçion la prima y la
primera:
mirad los ojos, rostro
cristallino,
y aquí puede hazer fin uuestro
camino.
Las dos mirad que están
sobrepujando,
a toda discreçion y
entendimiento,
y entre las más hermosas
señalando
se uan, por solo vn par, sin par
ni cuento,
los ojos que las miran
sojuzgando:
pues nadie las miró que biua
essento:
¡ued qué dira quien alabar
promete
las dos Beatrizes, Vique y
Fenollete!
Al tiempo que se puso alli
Diana,
con su diuino rostro y
excelente
salió un luzero, luego una
mañana
de Mayo muy serena y
refulgente:
sus ojos matan y su uista
sana,
despunta alli el amor su flecha
ardiente,
su hermosura hable, y
testifique
ser sola y sin ygual doña Anna
Vique.
Bolued, Nimphas, uereys
doña Teodora
Carroz, que del valor y
hermosura
la haze el tiempo reyna y gran
señora
de toda discreçion y graçia
pura:
qualquiera cosa suya os
enamora,
ninguna cosa nuestra os
assegura,
para tomar tan grande
atreuimiento,
como es poner en ella el
pensamiento.
Doña Angela de Borja
contemplando
uereys que está (pastores) en
Diana,
y en ella la gran dea está
mirando
la graçia y hermosura
soberana:
Cupido alli a sus pies está
llorando,
y la hermosa Nimpha muy
ufana,
en uer delante della estar
rendido
aquel tyrano fuerte y tan
temido.
De aquella illustre cepa
Çanoguera,
salio una flor tan extremada y
pura,
que siendo de su edad la
primauera,
ninguna se le yguala en
hermosura:
de su excelente madre es
heredera,
en todo quanto pudo dar
natura,
y assi doña Hieronyma ha
llegado
en graçia y disceçion al sumo
grado.
¿Quereys quedar (o
Nimphas) admiradas,
y uer lo que a ninguna dió
uentura:
quereys al puro extremo uer
llegados
ualor, saber, bondad y
hermosura?
mirad doña Veronica
Marradas,
pues solo uerla os dize y
assegura
que todo sobra, y nada falta
en ella,
sino es quien pueda (o piense)
meresçella.
Doña Luysa Penarroja
uemos
en hermosura y graçia más
que humana,
en toda cosa llega los
estremos,
y a toda hermosura uençe y
gana:
no quiere el crudo amor que la
miremos
y quien la uió, si no la uee, no
sana:
aunque despues de uista el
crudo fuego
en su vigor y fuerça buelue
luego.
Ya ueo, Nimphas, que
mirays aquella
en quien estoy continuo
contemplando,
los ojos se os yran por fuerça
a ella,
que aun los del mismo amor
está robando:
mirad la hermosura que ay en
ella,
mas ued que no çegueys
quiçá mirando
a doña Ioana de Cardona,
estrella
que el mismo amor está
rendido a ella.
Aquella hermosura no
pensada
que ueys, si uerla cabe en
nuestro uaso:
aquella cuya suerte fue
estremada
pues no teme fortuna, tiempo
o caso,
aquella discreçion tan
leuantada,
aquella que es mi musa y mi
parnaso:
Ioanna Anna, es Catalana, fin
y cabo
de lo que en todas por
estremo alabo.
 Cabe ella está un estremo
no uicioso,
mas en uirtud muy alto y
estremado,
disposiçion gentil, rostro
hermoso,
cabellos de oro, y cuello
delicado,
mirar que alegra, mouimiento
ayroso,
juyzio claro y nombre
señalado,
doña Angela Fernando, aquien
natura
conforme al nombre dio la
hermosura.
Vereys cabe ella doña
Mariana,
que de ygualalle nadie está
segura;
miralda junto a la exçelente
hermana,
uereys en poca edad gran
hermosura,
uereys con ella nuestra edad
ufana,
uereys en pocos años gran
cordura,
uereys que son las dos el
cabo y summa
de quanto dezir puede lengua
y pluma.
Las dos hermanas Borjas
escogidas,
Hippolita, Ysabel, que estays
mirando,
de graçia y perfeçion tan
guarnesçidas,
que al sol su resplandor está
çegando,
miraldas y uereys de quantas
uidas
su hermosura siempre ua
triumphando:
mirá los ojos, rostro, y los
cabellos,
que el oro queda atras y
passan ellos.
Mirad doña Maria
Çanoguera,
la qual de Catarroja es oy
señora,
cuya hermosura y graçia es de
manera,
que a toda cosa uençe y la
enamora:
su fama resplandeçe por do
quiera
y su uirtud la ensalça cada
hora,
pues no ay qué dessear
despues de uella,
¿quién la podrá loar sin
offendella?
Doña Ysabel de Borja está
defrente
y al fin y perfeçion de toda
cosa,
mira la graçia, el ser, y la
exçelente
color más biua que purpurea
rosa,
mirad que es de uirtud y graçia
fuente,
y nuestro siglo illustre en toda
cosa:
al cabo está de todas su
figura,
por cabo y fin de graçia y
hermosura.
La que esparzidos tiene sus
cabellos
con hilo de oro fino atras
tomados,
y aquel diuino rostro, que él y
ellos
a tantos coraçones trae
domados,
el cuello de marfil, los ojos
bellos,
honestos, baxos, uerdes, y
rasgados,
doña Ioana Milan por nombre
tiene,
en quien la uista pára y se
mantiene,
Aquella que alli ueys, en
quien natura
mostró su sçiençia ser
marauillosa,
pues no ay pasar de alli en
hermosura,
no ay más que dessear a una
hermosa:
cuyo ualor, saber, y gran
cordura
leuantarán su fama en toda
cosa,
doña Mençia se nombra
Fenollete,
 a quien se rinde amor y se
somete.

La cançion del çelebrado Orpheo,

fue tan agradable a los oydos de
Felismena, y de todos los que la
oyan, que assi los tenia
suspensos, como si por ninguno
de ellos uuiera passado más de lo
que presente tenian. Pues
auiendo muy particularmente
mirado el rico aposento, con
todas las cosas que en él auia
que uer, salieron las Nymphas por
una puerta de la gran sala, y por
otra de la sala a un hermoso
jardin, cuya uista no menos
admiraçion les causó que lo que
hasta alli auian uisto, entre cuyos
arboles y hermosas flores auia
muchos sepulchros de nimphas y
damas, las quales auian con gran
limpieça conseruado la castidad
deuida a la castissima diosa.
Estauan todos los sepulchros
coronados de enredosa yedra,
otros de olorosos arrayhanes,
otros de uerde laurel. De más
desto auia en el hermoso jardin
muchas fuentes de alabastro,
otras de marmol jaspeado, y de
metal, debaxo de parrales, que
por ençima de artifiçiosos arcos
estendian todas sus ramas, los
myrthos hazian cuatro paredes
almenadas, y por ençima de las
almenas, paresçian muchas flores
de jazmin, madreselua, y otras
muy apazibles a la uista. En
medio del jardin estaua una
piedra negra, sobre quatro pilares
de metal, y en medio de ella un
sepulchro de jaspe, que quatro
Nimphas de alabastro en las
manos sostenian, entorno dél
estauan muchos blandones, y
candeleros de fina plata, muy bien
labrados, y en ellos hachas
blancas ardiendo. En torno de la
capilla auia algunos bultos de
caualleros, otros de marmol
jaspeado, y de otras diferentes
materias. Mostrauan estas figuras
tan gran tristeza en el rostro, que
la pusieron en el coraçon de la
hermosa Felismena, y de todos
los que el sepulchro veyan. Pues
mirandolo muy particularmente,
vieron que a los pies dél, en una
tabla de metal que una muerte
tenía en las manos, estaua este
letrero:

Aqui reposa doña Catalina

de Aragon y Sarmiento cuya
fama,
al alto çielo llega, y se
auezina,
y desde el Borea al Austro se
derrama:
matéla, siendo muerte, tan
ayna,
por muchos que ella ha
muerto, siendo dama,
 acá está el cuerpo, el alma
allá en el çielo,
que no la meresçio gozar el
suelo.

Despues de leydo el Epigramma,

vieron cómo en lo alto del
sepulchro estaua vna aguda de
marmol negro, con vna tabla de
oro en las vñas, y en ella estos
uersos.

Qual quedaria (o muerte) el

alto çielo
sin el dorado Apollo y su
Diana
sin hombre, ni animal el baxo
suelo,
sin norte el marinero en mar
insana,
sin flor, ni yerua el campo y sin
consuelo,
sin el roçio d'aljofar la
mañana,
assi quedó el ualor, la
hermosura,
sin la que yaze en esta
sepultura.

Quando estos dos letreros

vuieron leydo, y Belisa entendido
por ellos quién era la hermosa
Nimpha que alli estaua sepultada,
y lo mucho que nuestra España
auia perdido en perdella,
acordandosele de la temprana
muerte del su Arsileo, no pudo
dexar de dezir con muchas
lagrimas: Ay muerte, quán fuera
estoy de pensar, que me as de
consolar con males agenos!
Dueleme en estremo lo poco que
se gozó tan gran ualor y
hermosura como esta Nimpha me
dizien que tenía, porque ni estaua
presa de amor, ni nadie meresçio
que ella lo estuuiesse. Que si otra
cossa entendiera, por tan dichosa
la tuuiera yo en morirse, como a
mí por desdichada en uer, o cruda
muerte, quan poco caso hazes de
mi: pues lleuandome todo mi bien,
me dexas, no para más, que para
sentir esta falta. O mi Arsileo, o
disçreçion jamás oyda, o el más
claro ingenio que naturaleza pudo
dar. ¿Qué ojos pudieron uerte,
qué animo pudo suffrir tu
desastrado fin? O Arsenio,
Arsenio, Arsenio quan poco
pudiste suffrir la muerte del
desastrado hijo, teniendo más
ocasion de suffrirla que yo? ¿Por
qué (cruel Arsenio) no quesiste
que yo partiçipasse de dos
muertes, que por estoruar la que
menos me dolia, diera yo çien mil
vidas, si tantas tuuiera? A Dios,
bienauenturada Nimpha, lustre y
honrra de la real casa de Aragon,
Dios dé gloria a tu anima, y saque
la mia de entre tantas
desuenturas. Despues Belisa vuo
dicho estas palabras, y despues
de auer uisto otras muchas
sepulturas, muy riquissimamente
labradas, salieron por una puerta
falsa que en el jardin estaua, al
verde prado: adonde hallaron a la
sabia Feliçia, que sola se andaua
recreando: la qual los reçibio con
muy buen semblante. Y en quanto
se hazia hora de çenar, se fueron
a vna gran alameda, que çerca de
alli estaua, lugar donde las
Nimphas del sumptuoso templo,
algunos dias salian a recrearse. Y
sentados en un pradezillo,
çercado de uerdes salzes,
començaron a hablar vnos con
otros: cada vno en la cosa que
más contento le daua. La sábia
Feliçia llamó junto a si al pastor
Sireno, y a Felismena. La Nimpha
Dorida, se puso con Syluano
hazia vna parte del verde prado, y
las dos pastoras, Seluagia, y
Belisa, con las más[1257]
hermosas Nimphas, Cinthia y
Polydora, se apartaron haçia otra
parte: de manera que aunque no
estauan vnos muy lexos de los
otros, podian muy bien hablar, sin
que estoruasse vno lo que el otro
dezia. Pues queriendo Sireno,
que la platica, y conuersaçion se
conformasse con el tiempo y
lugar, y tambien con la persona a
quien hablaua, començo a hablar
desta manera: No me paresçe