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Table Of Contents

The Foundations of the Dye Industry
General Discussion
The Various Operations of Intermediate Chemistry
1. Sulfonation
2. Nitration
3. Reduction
4. Introduction of the Hydroxyl Group
5. Introduction of Amino and Alkoxy Groups
6. Oxidation Methods
7. Introduction of Halogen
Practical Work in the Industrial Organic Laboratory
General
Proportions and Weighing
Laboratory Journals and Reports
Apparatus
Stirring Apparatus
Fig. 1. Porcelain stirrers for attaching to a bent glass rod
Filtration
Distillation
J. Distillation under Ordinary Pressure
2. Vacuum Distillation
3. Steam Distillation
SEPARATION OF REACTION PRODUCTS 27
Separation of Reaction Products
Basic Substances
Acidic Substances
Purification of Products
Testing the Product for Purity
Orientation Rules
1. Orientation in the Benzene Series
2. Orientation in the Napthalene Series
3. Orientation in the Anthraquinone Series
4. Orientation in the Carbazole Series
A. COMPOUNDS OF THE BENZENE SERIES
1. Chlorobenzene
Halogenation in General
2. Nitrobenzene
Nitration in General
The Lunge Nitrometer
3. Aniline from Nitrobenzene
Sulfonation in General
Alkali Fusion in General
o-Nitroanisole from o-Nitrochlorobenzene
2,4-Dinitrochlorobenzene from Chlorobenzene
Aniline-2,5-disulfonic Acid from Chlorobenzene
(c) Aniline-2,5-disulfonic Acid
4-Chloro-2-aminophenol from p-Dichlorobenzene
(a) ISitro-p-dichlorobenzene from p-Dichlorobenzene
(b) 4-Chloro-2-nitro phenol from ISitro-p-dichlorobenzene
(c) 4-Chloro-2-aminophenol from 4-Chloro-2-nitrophenol
m-Nitroaniline from m-Dinitrobenzene
Partial Reductions in General
m-Phenylenediamine from m-Dinitrobenzene
m-Chloronitrobenzene from Nitrobenzene
2-Chloro-4-dimethylaminobenzaldehyde
(a) p-Tolylhydroxylaminesulfonic Acid
(b) 2-ChlorO'4'dimethylaminobenzaldehyde
2,2'-Benzidinedisulfonic Acid from Nitrobenzene
Benzidine from Nitrobenzene
8. Derivatives of Aniline
Sulfanilic Acid from Aniline (Baking Process)
The Baking Process in General
(a) Phenylhydrazine-p-sulfonic Acid
(b) p-Sulfophenyl-3-methyl-5-pyrazolone
p-Aminoacetanilide from Aniline
(a) Acetanilide from Aniline
(c) p-Aminoacetanilide from p-JSitroacetanilide
Dimethylaniline (Diethyl- and Ethylbenzylanilines)
Tetramethyl-p,p'-diaminobenzohydrol (Michler Hydrol)
Diphenylamine from Aniline and Aniline Salt
Acetoacetanilide
DERIVATIVES OF BENZENESULFONIC ACID 143
9. Derivatives of Benzenesulfonic Acid
Benzene-m-disulfonic Acid
Resorcinol
DERIVATIVES OF PHENOL 145
10. Derivatives of Phenol
o- and p-Chlorophenol from Phenol
Chloranil46
(a) Preparation of the Azo Dye
(b) Reduction
11. Derivatives of Toluene
Benzal Chloride and Benzaldehyde from Toluene
(a) Benzal Chloride
2,6-Dichlorobenzaldehyde from o-Nitrotoluene
(d) 2,6-Dichlorobenzal Chloride
2-Nitro-4-aminotoluene from p-Toluidine
(a) Dinitrostilbenedisulfonic Acid
(b) Reduction to Diaminostilbenedisulfonic Acid
2-Chloro-5-aminobenzoic Acid
12. Gallamide and Gallic Acid from Tannin
BENZENE DERIVATIVES FROM NAPHTHALENE 171
13. Benzene Derivatives from Naphthalene
Preparation of the Catalyst
Performing the Reaction, Apparatus
Phthalimide from Phthalic Anhydride
Anthranilic Acid from Phthalimide
B. COMPOUNDS OF THE NAPHTHALENE SERIES
14. a-Nitronaphthalene and a-Naphthylamine55
Phenyl-a-naphthylamine
a-Naphthol from a-Naphthylamine
Naphthionic Acid from a-Naphthylamine
(a) Preparation of the Acid Sulfate
(b) Baking Process
SULFONIC ACIDS OF NAPHTHALENE 183
15. The Sulfonic Acids of Naphthalene
1,6- and 1,7-Naphthylaminesulfonic Acids (Cleve Acids)
Naphthalene-/?-sulfonic Acid and /?-Naphthol
Sulfonation of /8-Naphthol
(b) 2-Amino-8-naphthoic sulfonic Acid (Gamma Acid)
2. From 2*Naphthol-6,8-di*ulfonic Acid
l-NAPHTHYLAMINE-3,6-DISULFONIC ACID (FREUND ACID) 209
Phenyl-gamma Acid
l-AMINO-8-NAPHTHOL-3,6-DISULFONIC ACID (H ACID) 211
17. l-Amino-8-naphthol-3,6-disulfonic Acid (H Acid)
(b) l-Amino-8'naphthol-3,6-disulfonic Acid (H Acid)
18. l-Naphthylamine-5- and -8-sulf onic Acids
NAPHTHALENE-1,4,5,8-TETRACARBOXYLIC ACID FROM PYRENE 221
20. Naphthalene-l,4,5,8-tetracarboxylic Acid from Pyrene
(a) Tetrachloropyrene
(b) Naphthalenetetracarboxylic Acid
C. COMPOUNDS OF THE ANTHRAQUINONE SERIES
21. Anthraquinone
Method 1: Oxidation of Anthracene1
Method 2: From Phthalic Anhydride and Benzene
(a) o-Benzoylbenzoic acid
(b) Anthraquinone
(a) 2-Methylanthraquinone
(b) l-Nitro-2~methylanthraquinone
(c) l-Amino-2-methylanthraquinone
23. 2-Aminoanthraquinone
(a) Sodium Anthraquinone-2-sulfonate ("Silver Salt")
2-AMINOANTHRAQUINONE 229
(b) 2-Aminoanthraquinone
(a) Anthraquinone-1-sulfonic Acid
(c) 1-Anthraquinonyloxamic Acid79
(b) 1,5- and 1,8-Dihydroxy anthraquinone
26. 1,5-Dinitroanthraquinone and 1,5-Diamino- anthraquinone
(a) 1,5-Dinitroanthraquinone
(b) Reduction to 1,5-Diaminoanthraquinone
27. Quinizarin from p-Chlorophenol
D. AZO DYES
Laboratory Preparation of Azo Dyes
(a) Fundamental Considerations
(b) Diazotization
Examples
1, Theoretical
2. Practical
ISOLATION OF DYES 257
(d) Isolation of Dyes
1. Dyes without Sulfo or Carboxyl Groups
2, Dyes with Sulfo or Carboxyl Groups
TECHNICAL DIAZOTIZATION PROCEDURES 259
Technical Diazotization Procedures
Aniline
^-Nitroaniline
a-Naphthylamine
Sulf anilic Acid
Benzidine
Coupling Reactions
Single Coupling Reactions with Hydroxy Compounds
Acid Orange A or Orange II
Acetyl-H Acid and Amidonaphthol Red G
Fast Light Yellow G (Bayer)
Hansa Yellow G
Permanent Red 2G88
Helio Bordeaux BL89
(a) Preparation of the Sodium Salt
(b) Preparation of the Calcium Lake
Single Coupling Reactions with Amines
/^-Aminoazobenzene from Aniline
(a) Tropaeoline or Orange IV
(b) Azo Yellow (Indian Yellow, Helianthine, etc.)
SECONDARY DISAZO AND POLYAZO DYES 277
Secondary Disazo and Polyazo Dyes
Naphthylamine Black D
Naphthylamine black D
Benzo Light Blue 2 GL or Sirius Light Blue G *
(c) Preparation of the Trisazo Dye
Disazo and Polyazo Dyes from Diamines
Bismarck Brown G and R
Bismarck Brown R (Vesuvine R9 Etc.)
Chrysophenine G
Benzidine Dyes
Dianil Brown 3 GN
Diamine Green B
Direct Deep Black EW
Congo Red
Acid Anthracene Red G and Chromocitronine R
Acid anthracene red G Chromocitronine R
Sun Yellow G from p-Nitrotoluene
E. DI- AND TRIPHENYLMETHANE DYES
Malachite Green94
(a) Leuco Malachite Green
(b) Oxidation of the Leuco Base to the Dye
Xylene Blue VS
(b) Benzaldehydedisulfonic Acid
(c) Condensation to the Leuco Dye
(d) Oxidation to the Dye
Wool Blue 5B
Victoria Blue B
Wool Green S
F. OXAZINE AND THIAZINE DYES
Gallamine Blue from Gallamide
(a) Nitrosodimethylaniline
(b) Gallamine Blue
Methylene Blue from Dimethylaniline
(a) p-Aminodimethylaniline
(b) Thiosulfonic Acid of Bindschedler Green
G. ANTHRAQUINONE DYES
Alizarin
(b) Acid Dyes
Quinizarin Green or Alizarin Cyanine Green G
Alizarin Saphirol B and SE
Indanthrene Blue RS from /?«Aminoanthraquinone
Indanthrene Yellow GK9T
H. INDIGOID DYES
Indigo
(a) Phenylglycine-o-carboxylic Acid"
(b) Indoxylcarboxylic Acid
2. Traugott Sandmeyer Synthesis100
(a) Thiocarbanilide
(b) Hydrocyanocarbodiphenylimide
(d) a-Isatinanilide
(e) a-Thioisatin and Indigo
Thioindigo
(a) o-Carboxyphenylthiogly colic Acid (O Acid)
(b) 3-Hydroxythionaphthene
I. SULFUR FUSIONS
Primuline
Separation of the Melt
Naphthamine Yellow NN
Thiazole Yellow or Clayton Yellow
Dehydrothiotoluidinesulfonic acid—N ^
Dehydrothiotoluidinesulfonic acid—NH
Sulfur Black T from Dinitrochlorobenzene
J. PHTHALOCYANINES
Monastral Fast Blue BS, Heliogen Blue B
K. VACUUM DISTILLATION IN THE LABORATORY AND PLANT
L. THE FILTER PRESS
M. THE CONSTRUCTION AND USE OF AUTOCLAVES
General Rules on the Use of Pressure Vessels
N. CONSTRUCTION MATERIALS FOR DYE CHEMISTRY
1. Metals
2. Nonmetals
3, Materials of Organic Origin
TECHNICAL DETAILS OF FACTORY MANAGEMENT 369
O. TECHNICAL DETAILS OF FACTORY MANAGEMENT
P. CALCULATION OF COSTS FOR A SIMPLE DYE
Orange II or Acid Orange A
/3-Naphthol
(b) Fusion of the Sodium Salt
Sulfanilic Acid
(b) Reduction of Nitrobenzene
(c) Sulfonation of Aniline
Preparation of the Dye from Sulfanilic Acid and fi-Naphthol
Preparation of Standard Titrimetric Substances
Preparation of Pure Sulfanilic Acid
Preparation orlN Sodium Nitrite Solution
Preparation of 0.1 N Phenyldiazonium Solution
Determination of Amines
(a) Direct Determination
(b) indirect Determination
Determination of Naphthols
P-Naphthol
a-Naphthol
Dihydroxynaphthalenes (Molecular Weight 160)
Determination of Aminosulf onic Acids
Determination of Aminonaphtholsulf onic Acids
H acid—l-Amino-8-naphthol-3,6-disulfonic Acid
Principle of the Knecht Method
Preparation of the Titanium Trichloride Solution
Titration of Methylene Blue
Azo Dyes
Triphenylmethane Dyes
The Common Test Papers
Solutions for Spot Tests on Filter Paper
Evaluation of Zinc Dust
Evaluation of Lead Peroxide Paste
Polar Brilliant Red 3B and B
Polar Brilliant Red 3B
Benzo Light Grey BL112
Brilliant Sulfo Flavine (I.G.)
Literature on Analysis of Dyes
TABLE XIV. Derivatives of 2-Naphthylamine-5,7-disulfonic Acid 451
SUBJECT INDEX
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Fundamental Processes of Dye Chemistry

Fundamental Processes of Dye Chemistry

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Published by: Disha Jain on Sep 17, 2011
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