Huntsman Technical Visit – February 2017

Chemical Intermediates
Marketing & Technical Overview
Global chemical intermediates organization
VP Intermediates
(Global)
Partial organization chart, Elissa Sterry
not all functions are represented

Oxo Sales Manager Oxo Marketing Manager

(Global) (Global)
Sylvie Deffrenne Timothy McMinn

Chem. Intermediates Chem. Intermediates Chem. Intermediates

Sales Manager Market Development Product Manager
(Global) Managers (Global)
Craig Latiolais (Global) Cesar Jimenez
Leslie Hinton
Geert Steenbeke
Chem. Intermediates
Chem. Intermediates
Sales Representatives
Sales Representatives
(EMEAF)
(Americas) Chem. Intermediates
Lisa Crocker Market Planner
Oliver Stier
Keith Reed (Global)
Rita Van de Vyver
Victor Guedes Ting Chen

Chem. Intermediates
Sales Representative
Oxo
(Asia Pacific) Chemical Intermediates
Regional Marketing
Brian Chan Marketing / Technical Support
(Americas, EMEAF, AP)
Li Yuan
Philippe Buess (Global)
Don Mattran (Americas)
Silvio Carrettin (EMEAF)
Frank Liang (Asia Pacific)

Chemical Intermediates
 Huntsman Global Volume History

US Volume History EU & AP Volume History

2000 2000

1800 1800

1600 1600

1400 1400
Metric Tons

Metric Tons
1200 1200

1000 1000

800 800

600 600

400 400

200 200

0 0
2010 2011 2012 2013 2014 2015 2016 2017P 2010 2011 2012 2013 2014 2015 2016 2017P

Exxal 13 Exxal 10 Exxal 13 Exxal 11 Exxal 10

 Surfactant Technologies at Huntsman

Versatile Building Blocks Versatile Markets

Fatty Acid / Natural Alcohols Personal Care
Alky Phenols
Synthetic Alcohols Textiles
Mono-branched Alcohols Agrochemicals
Random/ Block Copolymers
Tallow Amine Home Care
Castor oil Industrial & Institutional
Ethylene glycol esters
Sorbitan Esters Mining / EOR
Alkyl polysaccharides Paper & Water Treating
Alkylamine
Tall Oil Fatty Acid Metalworking

EMCC would like to understand how it’s Chemical Intermediates portfolio can better
support Huntsman’s current and next generation technical needs for continuous growth
Agenda

• Alcohol Market Overview

- Focus on Mid-Range Alcohols (Synthetic and Natural)

• Exxal™ Alcohol Grade Slate

• Alcohol Ethoxylates: Surfactant Comparative Performance

- Alcohols C12-14
- Alcohols C9-11

• Biodegradability Testing
- Exxal Alcohols
- Alcohol Ethoxylate Derivatives
Alcohol Market Overview
Focus on Mid-Range Alcohols
Exxal Alcohol position in global market
Large C6+ global market ~8.6MT
• Plasticizer: Mono-isomer (2EH,2PH) and
multi-branched (C8-13)
• Detergent: LAO/internal Oxo, Ziegler, and
natural fatty alcohols
Alcohol consumption ~45% NVA
• Surfactant segment dominated by
natural detergent alcohols

2016 WW C6-C14+ Alcohol Market

Production source End-use consumption

Acrylates
Natural Surfactants 27%
7%
23%

10% Other
C2=
/Ziegler 46% 2-EH
6% 8.6 MT 2% As such
Linear 1%
olefins /
Oxo
Plasticizers
20%
3% 55%
Higher
olefins / Oxo
2-PH

Source: IHS Chemical Economics Handbook Plasticizer Alcohols 2015 and Detergent Alcohols 2012
C12-16 Alcohol Market
C12+ Detergent Alcohol Capacity
kT (Not including TDA) Capacity additions in excess of demand growth
5000 100%
• Additions primary for natural alcohols
4000 CU% 80% • Higher growth rates in developing countries
3000 60% Demand driven by surfactants
2000 40% • Alcohol ethoxylates used as nonionic surfactants
account for 41% of total demand; 4% AAGR
1000 20%
• I&I / Industrial applications forecasted to grow 3%
0%
'98 '05 '12 '16 '21
Natural Syn Lin

‘16 Global Production ‘16 Global Consumption

5-year AAGR

Other, 10%
2% AAGR
Surfactants, 84%
Syn Linear* 3% AAGR
23% Solvent, 6%
Natural
3% AAGR
4% AAGR
73% 2.6 MT

TDA
4%

*At least 35% linear backbone

Source: IHS Chemical Economics Handbook Plasticizer Alcohols 2015 and Detergent Alcohols 2016
 C10-11 Alcohol Market
‘16 Global Production
Synthetic Linear C10-11 alcohol demand primarily driven by plasticizers
16%
• Substitution to higher molecular weight plasticizers
• Tempered by phthalate perception
• Linear phthalates expected to decline
IDA / IUDA
45% 0.7 MT
2-PH Demand trends with general economic conditions
39%
• Largely follows patterns of the leading world economies
• The major end-use markets include:
– Construction & remodeling
– Automotive production
– Original equipment manufacture

‘16 Global Consumption

5-yr AAGR
Surfactants, 12%
3% AAGR

Acrylates, 4%
PLZ, 72% 6% AAGR

Lubes, 2%
2% AAGR
2% AAGR 3% AAGR

Other,
1% AAGR10%

Source: IHS Chemical Economics Handbook Plasticizer Alcohols 2015 and Detergent Alcohols 2016
Alcohol and Feedstock Pricing
$/T
Natural Alcohol Pricing $/bbl
7,000 150
AP C8 Nat
6,000 125
AP C10 Nat
5,000
AP C12-14 Nat 100
4,000 WTI Crude
75
3,000
50
2,000

1,000 25

Jan-04 Jan-06 Jan-08 Jan-10 Jan-12 Jan-14 Jan-16

Synthetic Alcohol Feedstocks

$/T
2,000
USGC C2= C12 naturals pricing impacted by excess capacity
USGC CGP
• Recent increases due to capacity consumption
1,500 EU Nap
C8-10 naturals pricing has diverged
1,000 • Preference for palm capacity vs coconut capacity

500 • Palm has lower mid-cut yield

• Increased competition from biodiesel use
Recent decline in feedstock prices driven by crude
• Syn feedstocks diverging despite crude increases
Source: ICIS Pricing
Exxal Alcohol Grade Slate
 Oxo Process Integration
Distillation Cracking Olefin sales Alcohol sales Plasticizers
Steam-Cat

Naphtha Oligomerization Hydroformylation Esterification

Propylene
Branched Jayflex™
Exxal™ 8
Olefins Exxal™ 9
Crude Oil Gasoil DINP
C6-C12 Exxal™ 10
DIDP
Exxal™ 11
Butenes DIUP
Exxal™ 13
DTDP

Heavy Gasoil
Neo
Acids

Phthalic
O-xylene
anhydride
Global Supply with Regional Responsiveness

Rotterdam
Fawley

Sarnia Shanghai
Antwerp
Technology
Machelen Center
NDG, France
Technology
Baytown Center
Technology Baton Rouge
Center

Singapore

Regional inventory of global grades

Manufacturing site Oxo alcohol
US EU AP Brazil
Technology Center Higher olefin •
Exxal 8 • •
Key Integrated site Neo Acids Exxal 9 • • • •
Exxal 10 • • • •
Exxal 11 ◦ • ◦
Exxal 13 • • • •
Neo Acid • • •
Exxal Alcohol Typical Properties
Exxal 8 Exxal 9 Exxal 10 Exxal 11 Exxal 13
Chemical Name Isooctanol Isononanol Isodecanol Isoundecanol Isotridecanol
Acid Value
Mg KOH/g - ASTM D1045* <0.05 <0.05 <0.05 <0.10 <0.03
Boiling Range
°C – ASTM D1078* 186 - 192 204 - 214 218 - 224 233 - 239 255 – 263
Carbonyl Number
Mg KOH/g ISO 1843-1/ASTM E411* <0.20 <0.20 <0.20 <0.20 <0.20
Color
Pt/Co – ASTM D5386 5 5 5 5 5
Density at 20°C
g/cm3 – ASTM D4052 0.831 0.835 0.838 0.841 0.846
Flash Pt.
PMCC °C – ASTM D93 >70 >80 >90 >100 >100
Hydroxyl Number
Mg KOH/g – ISO 1843-5 425 377 350 321 285
Pour Pt.
°C – ASTM D5950* <-40 <-40 <-40 <-40 <-40
Viscosity at 20°C
Mm2/S – ASTM D445 12 17 21 27 48
Water content
Wt% - ISO 12937 <0.1 <0.1 <0.1 <0.1 <0.1
These are not sales specifications. The data is listed here for comparative purposes only. Sales specifications for Exxal
alcohols are available through the product links at www.exxonmobilchemical.com (Alcohol at a Glance Brochure)
 Structural Data for Exxal Alcohols

Average Carbon Number Distribution by GC (wt%)

C6 C7 C8 C9 C10 C11 C12 C13 C14 Avg Spec Limits
+ Branching Max
(# branches/molecule)

C6+C10+ C7 C9
Exxal 8 < 0.1 1.8 92.7 5.2 0.2 1.61
2.0 3.5 2.0 – 9.0
C8 C10 C11+
Exxal 9 3.0 77.1 18.8 1.1 1.87
6.0 18 – 22 2.5
C8 C9 C11+
Exxal 10 0.1 6.4 88.2 5.2 2.06
0.75 10.0 7.0
C10 – C11 C12+
Exxal 11 6.7 87.0 6.3 2.20
6.7 87.0 6.3
C9+10 C14+
Exxal 13 0.17 0.3 1.4 21.5 70.1 6.7 3.07
2.0 10.0

α-branching estimated between 10-15%

% Quaternary Carbons estimated between 1-2%

Registration and WW Inventory Status
Exxal 8 Exxal 9 Exxal 10 Exxal 11 Exxal 13
Chemical Name Isooctanol Isononanol Isodecanol Isoundecanol Isotridecanol

CAS Number 68526-83-0 68526-84-1 68526-85-2 68551-08-6 68526-86-3

EC Number 271-231-7 271-233-5 271-234-0 271-360-6 271-235-6

CAS Definition Alcohols, C9- Alcohols, C11-

Alcohols, C7-9- Alcohols, C8- Alcohols, C9-11-
11-iso-, C10- 14-iso-, C13-
iso-, C8-rich 10-iso-, C9-rich branched
rich rich

REACH (EU) Full Substance Intermediate Full Substance Full Substance Full Substance

REACH Number 01-

01-2119449923- 01-2119459285- 01-2119449922- 01-2119454259-
2119449807-
30-0001 32-0000 32-0000 32-0000
26-0000

Exxal Alcohol
listings on WW
ENCS
Inventories TSCA
ISHL
KECI TCSI PICCS AICS DSL IECSC
Alcohol Ethoxylates:
Surfactant Comparative Performance
Alcohols C12 - 14
Alcohols C9 - 11
Ethoxylate Performance: C12-14 Alcohols
Exxal 13 vs Linear C12-14 vs Nonylphenol
Exxal 13 Key Performance Advantages
• Better dynamic properties
• Superior wetting performances
• Less gel phases

Property Units Method

Surface tension lowering and mN/m CI-TM8
pC20
Gel phase : maximum wt% CI-TM5
concentration without gel surfactant (viscosity)
phase by viscosity
Wetting time by Draves test seconds CI-TM3
(ASTM-D2281)

Foam height by Ross-Miles mm CI-TM6

(ASTM D1173)
Dynamic surface tension by mN/m CI-TM7
max. bubble pressure DST*

Note CI-TM refer to ExxonMobil methods

 GC Distributions
12.0
C10 alcohols ethoxylated (6EO)
10.0

8.0
Exxal 10
Wt (%)

6.0
Syn Linear C10

4.0 Nat Linear C10
SL 9‐11
2.0

0.0 Branched and linear

0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21
Mole EO/mole ethoxylates demonstrate
12.0 very similar molecular
C11 Alcohols Ethoxylated (7EO) weight distributions
10.0

8.0

6.0
Wt %

Exxal 11
4.0
Semi‐linear C11
2.0

0.0
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
‐2.0
Mole EO/mole
 Cloud Points (1 wt% in water)
90.0
At same degree of ethoxylation
80.0
and similar carbon number,
SL C9-11 Exxal alcohols result in lower
70.0
cloud-points than linear products
SL C11
Cloud point in water °C

C10
For same cloud point,
60.0 Exxal 10
Exxal 11
more EO must be added
on branched alcohol
50.0

40.0

30.0

Curves obtained by regression of larger data sets

20.0
5 6 7 8 9 10
Mole EO/mole
 Surface Tension Lowering
5‐6 EO/mole 7‐8 EO/mole
27.5 739 800 29.5 1600

29.0 1360 28.8

27 700 1400
27.0 26.8 28.5
Surf Tension at CMC (mN/m)

600 1200

Surf Tension at CMC (mN/m)
26.5 27.9
26.5 28.0
500 27.5 1000

CMC (mg/L)
26.1 27.5

CMC (mg/L)
26.0 27.0
26.0 400 27.0 800
311 311 26.7
25.6
300 26.5 529 558
25.5 600
198 428
178 26.0
200 329 26.0 400
25.0 25.5
61 100
114 200
25.0
24.5 0
24.5 0
Exxal 10‐6

Syn Linear C10‐6

SL C9‐11‐6
Nat Linear C10‐6

SL C11‐5
Exxal 11‐5

Exxal 10‐8

Imbentin‐8

SL C9‐11‐8

Exxal 11‐7
Greenbentin‐8

SL C11‐7
Min. ST (mN/m) CMC (mg/L) Min. ST (mN/m) CMC (mg/L)

Exxal alcohol ethoxylates are effective in reducing surface tension

Branching lowers minimum surface tension

 Wetting time (s)

0
1
2
3
4
5
6
7
8
9
10
Exxal 10‐6

3.2
Syn Linear C10‐6

3.9
Nat Linear C10‐6

3.6
5‐6 EO/mole

SL C9‐11‐6

4.2

Exxal 11‐5 3.1

SL C11‐5
4.9

Wetting time (s)
0
1
2
3
4
5
6
7
8
9
10
Wetting Time (Draves Test)

Exxal 10‐8
9.1

Syn Linear C10‐8
9.9

Nat Linear C10‐8
7.4

Branched hydrophobes impart shorter wetting times

7‐8 EO/mole

SL C9‐11‐8
8.3

Exxal 11‐7
3.5

SL C11‐7
5.5
 Ethoxylate Phase Behaviour
C10 – 6 EO Surfactants C10 – 8 EO Surfactants
45 45
Syn Linear C10 ‐ 8 EO
40 SL C9‐11 ‐ 6 EO 40
Nat Linear C10 ‐ 8EO
Exxal 10 ‐ 6 EO
Temperature (°C)

35 SL C9‐11 ‐ 8 EO

Temperature (°C)
35
Exxal 10 ‐ 8 EO
30 Gel
30
Liquid Liquid
25 Gel 25
Liquid Liquid Gel
20 20
Gel
15 15
0 0.2 0.4 0.6 0.8 1 0 0.2 0.4 0.6 0.8 1
Active content Active content

C11 – 7 EO Surfactants
45
SL C11 ‐ 7 EO No gel phase formation
40 Exxal 11 ‐ 7 EO for Exxal 10-8 EO
Temperature (°C)

35
Less gel phase formation for
Liquid
30 Exxal 10-6 EO and Exxal 11-7 EO
Liquid
25
Gel
20
Gel
15
0 0.2 0.4 0.6 0.8 1
Active content
 Foaming Characteristics
Foam height versus Time – 5EO Foam height versus Time – 7EO
120 120

100 100

Foam height (mm)
Foam height (mm)

80 80

60 60

40 40
Semi‐linear C11 5EO Semi‐linear C11 7EO
Exxal 11 5EO Exxal 11 7EO
20 20

0 0
0 100 200 300 400 0 100 200 300 400
Time (s) Time (s)

Exxal™ 11’s branched structure generate less stable foam

when compared to semi-linear alcohols at the same degree
of ethoxylation
Biodegradability Testing
Biodegradability Testing (OECD 301F)

• The biological decay of a chemical is followed over time

• Ultimate: complete disappearance to CO2, H2O, mineral compounds
• A solution, or suspension, of the test substance in a mineral medium is
inoculated and incubated under aerobic conditions
• Inoculum sources are broadly defined to avoid industrial sources
• Degradation is followed by the determination of oxygen consumption
• The test lasts for 28 days (can be extended)
• Criterion for pass: 60% degradation in 28 days (for respirometric tests)
• For single component substances, the time from 10% to 60% degradation
must occur within a 10-day window
• Variability recognized by regulators – one favorable result indicates
favorable potential for biodegradation
Exxal™ Alcohols and their ethoxylates meet the
requirements to be readily biodegradable

26
Exxal Alcohols in Surfactant Applications

• Low pour point alcohols  ease of processing

• Effective building blocks for performance surfactants

- High surface tension lowering
- Fast wetting of surfaces
- Less gel phases for better handling

• Ethoxylate derivatives meet biodegradability requirements

Exxal Alcohols provide enhanced performance

in a wide range of surfactant applications
©2017 ExxonMobil. ExxonMobil, the ExxonMobil logo, the interlocking “X” device and other product or service names used herein are trademarks of ExxonMobil, unless
indicated otherwise. This document may not be distributed, displayed, copied or altered without ExxonMobil's prior written authorization. To the extent ExxonMobil
authorizes distributing, displaying and/or copying of this document, the user may do so only if the document is unaltered and complete, including all of its headers, footers,
disclaimers and other information. You may not copy this document to or reproduce it in whole or in part on a website. ExxonMobil does not guarantee the typical (or
other) values. Any data included herein is based upon analysis of representative samples and not the actual product shipped. The information in this document relates
only to the named product or materials when not in combination with any other product or materials. We based the information on data believed to be reliable on the date
compiled, but we do not represent, warrant, or otherwise guarantee, expressly or impliedly, the merchantability, fitness for a particular purpose, freedom from patent
infringement, suitability, accuracy, reliability, or completeness of this information or the products, materials or processes described. The user is solely responsible for all
determinations regarding any use of material or product and any process in its territories of interest. We expressly disclaim liability for any loss, damage or injury directly or
indirectly suffered or incurred as a result of or related to anyone using or relying on any of the information in this document. This document is not an endorsement of any
non-ExxonMobil product or process, and we expressly disclaim any contrary implication. The terms “we,” “our,” "ExxonMobil Chemical" and "ExxonMobil" are each used
for convenience, and may include any one or more of ExxonMobil Chemical Company, Exxon Mobil Corporation, or any affiliate either directly or indirectly stewarded.