Exxal™ Alcohols for SurfactantsJuly 2018

ExxonMobil Overview

2

ExxonMobil Corporation

Upstream Downstream Chemical

ExxonMobil Chemical Structure C

he

mic

als

Polymers

Global Operations

Global Technology

Basic Chemicals, Intermediates, &

Synthetics

Basic Chemicals

Synthetics

Intermediates

Fluids

Oxo

Plasticizer

Chemical Intermediates

Global chemical intermediates organizationVP Intermediates

Matthew Crocker

Chem. IntermediatesMarket DevelopmentManagers

Leslie HintonGeert Steenbeke

Customer and Application Development

Don Mattran (Global Lead)Daniel Bien (Global Advisor)Silvio Carrettin (EMEAF)Frank Chen (AP)Nelson Akaighe (Global Developer)Sanja Natali (Global Developer)

AmericasChem. IntermediatesSales Representatives

Kevin LongKeith ReedVictor Guedes

EMEAFChem. IntermediatesSales Representatives

Oliver StierRita Van de Vyver

Asia PacificChem. IntermediatesSales Representatives

Brian ChanLi Yuan

Chem. IntermediatesSales Development Lead

Lisa Crocker

Chem. IntermediatesStewardship & Regulatory Affairs

Ming Kung

Oxo Marketing Manager

Laura Winks

Oxo Sales Manager

Sylvie Deffrenne

Chem. IntermediatesSales Manager

Craig Latiolais

Oxo Product Manager

Cesar Jimenez

Oxo Market Planner

Ting Chen

Oxo Regional Product Managers

Mark Klewpatinond (AM)Frank Braeckmans (EMEAF)Ray Lee (AP)

Partial organization chart as of June 2018

Exxal™ Alcohols

6

Global oxo platform with production sites in all three regions

ExxonMobil oxo platformIntegrated, global, flexible

Propylene C3=

Butylene C4=

Ortho-Xylene

Branched higher olefinsC6= to C12=

Neo acidsC5,C10

PAN

Jayflex™plasticizer

DINPDIDPDIUPDTDP

SC, FCC

SC, FCC

Reformer oxidation

oligomerization

carbonylation

oxo esterification

Branched oxo alcohols

Exxal™ 8 Exxal™ 9 Exxal™ 10Exxal™ 11 Exxal™ 13

Integrated feedstocks Chemical intermediates Plasticizers

Exxal™ Alcohols

Adhesives Lubricants

Stabilizer packages

Plastics / Polymers

Exxal™ 8 Exxal™ 9 Exxal™ 10 Exxal™ 11 Exxal™ 13

Acrylates/ Methacrylate

Zincdithio

phosphates

Thioglycolates

Phosphites PhosphatesEsters

Non-ionic surfactants

EO,PO

Phenolic Antioxidant

Ionic surf. sulfates,

phosphates

Industrial Surfactants

Lube Additives

Branched alcohols and derivatives are performance differentiated

• Low pour points

• High steric hindrance

Surfactant derivatives based on branched molecules offer:

• Better dynamic properties

• Superior wetting performances

• Less gel phases

Exxal Alcohol Structures

Exxal 8

Theoretically 39 primary alcohol isomers possible

Exxal 9S

Theoretically 89 primary alcohol isomers possible

Exxal 10

Theoretically 211 primary alcohol isomers possible

Exxal 11

Theoretically OVER 500 primary alcohol isomers possible

Exxal 13

Theoretically OVER 3057 primary alcohol isomers possible

Exxal 8 Exxal 9S Exxal 10 Exxal 11 Exxal 13

Chemical Name Isooctanol Isononanol Isodecanol Isoundecanol Isotridecanol

Acid ValueMg KOH/g - ASTM D1045* <0.05 <0.05 <0.05 <0.10 <0.03

Boiling Range°C – ASTM D1078* 186 - 192 201 - 207 218 - 224 233 - 239 255 – 263

Carbonyl NumberMg KOH/g ISO 1843-1/ASTM E411* <0.20 <0.20 <0.20 <0.20 <0.20

ColorPt/Co – ASTM D5386 5 5 5 5 5

Density at 20°Cg/cm3 – ASTM D4052 0.831 0.834 0.838 0.841 0.846

Flash Pt.PMCC °C – ASTM D93 >70 >80 >90 >100 >100

Hydroxyl NumberMg KOH/g – ISO 1843-5 425 377 350 321 285

Pour Pt.°C – ASTM D5950* <-40 <-40 <-40 <-40 <-40

Viscosity at 20°CMm2/S – ASTM D445 12 17 21 27 48

Water contentWt% - ISO 12937 <0.1 <0.1 <0.1 <0.1 <0.1

Exxal Alcohol Typical Properties

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)

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

Spec LimitsMax

Exxal 8 < 0.1 2.6 92.0 5.1 0.3 1.6C6+C10+

2.0C73.5

C92.0 – 9.0

Exxal 9S 1.9 91.5 6.5 0.1 1.8

Exxal 10 3.0 89.8 7.2 2.0

Exxal 11 0.5 8.5 84.6 6.4 2.2

Exxal 13 0.1 0.2 1.8 21.4 69.7 6.8 3.1C9+10

2.0C14+

10.0

Structural Data for Exxal Alcohols

Average Carbon Number Distribution by GC (wt%)

C2-branching estimated between 10-15%

Global supply with regional responsiveness

Baton Rouge

ShanghaiTechnology

Center

BaytownTechnology

Center

MachelenTechnology

Center

Oxo alcohol

Higher olefin

Neo Acids

Sarnia

NDG, France

Fawley

Antwerp

Rotterdam

Singapore

Regional inventory of global grades

US EU AP Brazil

Exxal 8 • • •

Exxal 9 • • • •

Exxal 10 • • • •

Exxal 11 ◦ • •

Exxal 13 • • • •

Neo Acid • • •

Manufacturing site

Technology Center

Key Integrated site

Exxal 11 vs Exxal 13

13

Exxal™ 13 Performance at a Glance

Exxal alcohols :• Better dynamic properties• Superior wetting performances• Less gel phases

Property Units Method

Surface tension lowering and

pC20

mN/m CI-TM8

Gel phase : maximum

concentration without gel

phase by viscosity

wt%

surfactant

CI-TM5

(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

max. bubble pressure

mN/m CI-TM7

DST*

Note CI-TM refer to ExxonMobil methods

Exxal 13 vs Competitive Alcohols8 Mole EO

Exxal™ 11 vs Exxal 13 in Surfactant Applications

20

30

40

50

60

70

80

90

5 6 7 8 9 10 11

Clo

ud

po

int

in w

ate

r °C

Mole EO/mole

Exxal 11

Exxal 13

Exxal™ 11 (EO)x and Exxal 13 (EO)x+1 have comparable cloud points and HLB values

* Model curves based on internal ExxonMobil data

Cloud Point

Exxal 11-7EO Exxal13-8EO Exxal 11-8EO Exxal13-9EO

Cloud point in water (°C) 46.5 44.3 61.6 57.7

HLB 12.8 12.8 13.5 13.3

Dyn. Viscosity (mPa.s) @40°C 28.3 36.9 31.29 40.56

Kin. Viscosity (mm2/s) @40°C 28.7 37.4 31.45 40.80

Density (g/cc) @40°C 0.9879 0.9863 0.9950 0.9940

Pour Point (°C) +11.0 +14.0 +16.0 +18.0

Exxal™ 11 and Exxal 13 Ethoxylate Comparison

At similar HLB, cloud point and pour point of the corresponding ethoxylates are close while the viscosity of the Exxal 11 ethoxylate is lower

Exxal™ 11 and Exxal 13 ethoxylates are equivalent at loweringsurface tension, while the CMC of the Exxal 13 ethoxylate is much lower

26.5 27.2

376

76

0

50

100

150

200

250

300

350

400

10.0

15.0

20.0

25.0

30.0

Exxal 11-7 Exxal 13-8

CM

C (

mg

/L)

Su

rf T

en

sio

n a

t C

MC

(m

N/m

)

Min. ST (mN/m) CMC (mg/L)

Surface Tension and CMC

Wetting: Hydrophobe Comparison

Draves Test Wetting Time, 1g/L, room temp.

3.5 3.3

0.0

1.0

2.0

3.0

4.0

5.0

Exxal 11-7 Exxal 13-8

We

ttin

g t

ime

(s)

Wetting properties of Exxal™ 11 and 13 ethoxylates are comparable

15

25

35

45

55

65

75

0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9

Te

mp

era

ture

(°C

)

Active Content

Exxal 13-8EO

Exxal 11-7EO

Exxal™ 11 ethoxylates have lower gel phase formation

Gel Phase Formation

Air-sparging method. Surfactant 0.1 g/L. Air flow 0.3 L/min. T=20C. Demin. water

0

20

40

60

80

100

120

0 100 200 300 400

Fo

am

He

igh

t (m

m)

Time (s)

Foam height versus time

Exxal 13-8EO 0.1g/l I

Exxal 11 7EO 0.1 g/l

83.476.378.20

41.20

0

20

40

60

80

100

Fo

am

he

igh

t (m

m)

Foam Height collapse after 180 and 300s

Exxal 13-8EO HLB 12.8 Exxal 11 7EO HLB 12.9

300s180s

Exxal™ 11 ethoxylates show slightly higher foam formation but faster collapse

Foaming Characteristics

Exxal™ 11 Ethoxylate Exxal™ 13 Ethoxylate

Pour Point - Alcohol = =

Reactivity = =

Effectiveness (lowering surface tension) = =

Efficiency (CMC) +

Wetting time = =

Gel phase +

Foam collapse Faster Slower

Biodegradability Readily biodegradable Readily biodegradable

Maximum solubility of oil per 1g of surfactant +

Interfacial Tension +

Summary/Conclusions

Exxal™ 11can be used as an effective alternative to Exxal 13 in high performance ethoxylate surfactants

Exxal 10™ vs C9-11 Alcohols

24

GC Distribution of C10 Alcohols Ethoxylated (6EO)

25

Reactivity of Exxal™ 10 is very similar to other C10 alcohols

Method: 26.2.1 (ExxonMobil)

Cloud Points (1% in Water)

26

At the same degree of ethoxylation, Exxal™ 10 ethoxylates have lower

cloud-point than linear and semi-linear alcohol ethoxylates

Method: CI-TM1 (ExxonMobil)

Surface Tension Lowering: Hydrophobe Comparison

27

Method: CI-TM8 (ExxonMobil)

Exxal™ 10 is better at lowering surface tension, but its CMC is higher

Draves Test

28

Branched hydrophobes impart shorter wetting times

Method: CI-TM3 (ExxonMobil)

Gel Phase Formation

29

Exxal™ 10 ethoxylates exhibit less gel phase formation

than linear and semi-linear alcohol ethoxylates

Method: CI-TM5 (ExxonMobil)

Maximum solubility of oil per 1g of surfactant

30

Exxal™ 10 ethoxylates solubilize oils better than

linear and semi-linear alcohol ethoxylates

* Theoretical calculations based on internal ExxonMobil data

Interfacial Tension

31

Exxal™ 10 ethoxylates show lower interfacial tension

when compared to linear and semi-linear alcohol ethoxylates

* Theoretical calculations based on internal ExxonMobil data

Summary and Conclusion

32

Exxal™ 10 ethoxylates offer performance benefits enabling high

performing surfactants vs competitive surfactants in many applications

Best PerformingEthoxylate

Reactivity

Effectiveness (lowering surface tension)

Efficiency (CMC)

Wetting time

Gel phase

Maximum solubility of oil per 1g of surfactant

Interfacial Tension

Exxal™ 10

L C10

SL C9-11

Regulatory Landscape

Historical scheme for chemical safety regulation

Safety of FacilitiesProtect workers and

immediate environment from chemicals

Safety of Chemical ProductsProtect general public &

environment from chemicalse.g. surfactant biodegradation

Timeline

Number and complexity of

Regulations

Emerging economy

Developed economy

Emerging trend for chemical safety regulation

Timeline

Number and complexity of

Regulations

Emerging economy

Developed economy

• Proliferation of Chemicals Management regulations

• China

• Korea

• Turkey

• Taiwan

• Increased complexity (EU REACH, TSCA)

• Formulator/end user requirements increasing• Walmart

• California

• Sustainability an increasing focus

• Definition varies by country and sector

Rapidly increasing global compliance requirements

0

100

200

300

400

500

600

700

800Americas minus USA & Canada

Eurasia, ME & Africa

AP Minus China

China

We can help you navigate the increasingly complex global landscape

Regulatory Growth in Emerging Economies

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, C7-9-iso-, C8-rich

Alcohols, C8-10-iso-, C9-rich

Alcohols, C9-11-iso-, C10-rich

Alcohols, C9-11-branched

Alcohols, C11-14-iso-, C13-rich

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

REACH Number 01-2119449923-30-0001

01-2119459285-32-0000

01-2119449807-26-0000

01-2119449922-32-0000

01-2119454259-32-0000

Registration and world-wide inventory statusExxal alcohols

TSCAENCSISHL

KECI TCSI PICCS AICS DSL IECSCEINECSELINCS

Focus on Sustainability

Source: ExxonMobil Corporate Citizenship Report, 2015

ExxonMobil is committed to addressing the challenge of sustainable development -balancing economic growth, social development and environmental protection so future generations are not compromised by actions taken today

Our Commitment to Sustainability

By designing our approach to corporate citizenship around six key focus areas, we contribute to society’s broader sustainability objectives and manage the impact of our operations on local economies, societies and the environment

Embedding sustainability into our chemical business

of

freshwater

consumption at our

operations

2016 vs. 10-yr avg*:

-14%

Managing

water use

Workforce

Lost Time Injury

2016 Performance:

0.03

Focusing

on safety

Developing

new solutions

GHG emissions

2016 vs. 10-yr avg*:

-9%

Mitigating

emissions

of

cogeneration capacity

Equivalent to the

annual energy

needed to power 2.5

million U.S. homes

5,500MW

Energy

efficiency

Source: www.exxonmobilchemical.com

*2007-2016 Average

increase in crop

yield with

polyethylene films

such as films made

from Exceed™ XP

+50%

• Responsibility throughout life cycle

• e.g., ISO 14001 certification

• Responsible Care®

• Hazards well-characterized

• Readily biodegradable – feedstock and derivatives1

• Lower pour point – easier handling2

• Lower greenhouse gas emissions vs. ‘average’ of palm kernel oil–based alcohols3

• No ‘food versus chemical’ debate – synthetic alcohols do not directly impact food prices or land use

What defines a sustainable surfactant feedstock?

1 Per OECD 301F2 Exxal 13 pour point <40°C per ASTM D59503 Shah et al. Comparison of Oleo- vs Petro-Sourcing of Fatty Alcohols via Cradle-to-Gate Life Cycle Assessment. J Surfactants Deterg. 2016; 19(6): 1333–1351.

• Hazard properties well understood through extensive toxicological dataset

• All Exxal™ alcohols meet ready biodegradable criteria per OECD 301F

• Health Information Profiles and Product Environmental Profiles summarize key data and basis for hazard conclusions

• Available upon request

Exxal™ alcohols: thoroughly studied

Enabling Sustainable Surfactants

Biodegradability testing at EMBSI: OECD 301F

• Measures “ultimate” biodegradation

• Uses manometric respirometer

• Monitors oxygen consumption

continually

• Conducted with non-acclimated

inoculum

• Requires 60% “pass” level

Branched alcohols and their ethoxylates biodegradability

0

10

20

30

40

50

60

70

80

90

100

0 2 4 6 8 10 12 14 16 18 20 22 24 26 28

% B

iod

eg

rad

ati

on

Days

Exxal™ 10

Exxal™ 10-6EO

Per OECD 301F

ExxonMobil data

Exxal™ 8 – 4EO

Exxal™ 8 – 6EO

Exxal™ 8 – 8EO

Exxal™ 8 – 10EO

Exxal™ 9 – 1EO

Exxal™ 9 – 3EO

Exxal™ 9 – 5 EO

Exxal™ 9S – 7EO

Exxal™ 9 – 8EO

Exxal™ 9 – 20EO

Exxal™ 10 – 3EO

Exxal™ 10 – 6EO

Exxal™ 10 – 7EO

Exxal™ 11 – 7EO

Exxal™ 13 – 3EO

Exxal™ 13 – 5EO

Exxal™ 13 – 7EO

Exxal™ 13 – 8EO

Exxal™ 13 – 9EO

ExxonMobil has a diverse alcohol grade slate that meets the standards…

Branched alcohol

Exxal™ 8

Exxal™ 9

Exxal™ 9S

Exxal™ 10

Exxal™ 11

Exxal™ 13

Branched alcohol ethoxylate

Exxal™ alcohols and ethoxylates are readily biodegradable

Readily biodegradable (>60%) per OECD 301F Within 10-day window

0.1

1

10

100

Exxal 12*-7EO Exxal 13-7EO Semi-linear C13-15-7EO

Semi-linear C12-15-7EO

LC/EC 50 (mg/L)

Branched alcohol ethoxylates have lower labelling requirements

Less Toxic

More Toxic

algae

Daphnia

rainbow trout

fathead minnow

Acute aquatic toxicity of 7-mole EO surfactants

Any result below 1 mg/L would lead to classification as acute category 1 under GHS

ExxonMobil data

Exxal™ Alcohols for Sustainable Surfactants

Sustainability in Raw Material Selection

Sustainability in Manufacturing

• Fast wetting times could lead to reduced water consumption and faster processing

• Less gel phases could help with energy efficiency

• Exxal alcohols and their ethoxylate derivatives are readily biodegradable per OECD 301F

• Aquatic toxicity testing to date indicates no GHS Category 1 label required for Exxal ethoxylates

• Publication of biodegradability and toxicity testing coming in late 2018

• 3rd party LCA indicates minimal differences between Oleo and Petro based alcohols

• ExxonMobil Chemical relentlessly focuses on mitigating emissions, managing water usages, and reducing energy consumption

• All Exxal alcohols have a pour point < -40⁰ F• Low pour point Exxal alcohols could increase

energy efficiency with ease of transportation and handlingSustainability in Use

Sustainability in Disposal

ExxonMobil Vision to 2030

49

30

60

90

'00 '04 '08 '12 '16

Index

Energy 2.0%

GDP 2.7%

Chemicals 4.2%

Demand growth

Leverage our unique position for advantaged

growth

Establish ourselves as a visible industry leader in

sustainability

Grow Lead

Continue to strengthen major integrated

complexes

Strengthen

Our vision for ExxonMobil Chemical

Oxo business strategy aligned with EMCC strategy

Propylene C3=

Butylene C4=

Ortho-Xylene

Branched higher olefinsC6= to C12=

Neo acidsC5,C10

PAN Jayflex™plasticizer

Exxal™ 8 Exxal™ 9 Exxal™ 10 Exxal™ 11 Exxal™ 13

Focus on New Applications and New Products

Lower CN

Higher CN

Ethylene C2=Linear alpha olefinsC4= to C24= Coatings

Adhesives

Lube/Fuel Additives

Polymer Additives

Surfactants

Others

Customer Derivatives

www.surfactantswhycompromise.com

Performance and SustainabilityExxal Alcohols for Surfactants

Optimized and expanded production

Strong surfactant

growth

Focus on specialty products

Meeting Sustainability

goals

Performance differentiation

Back-up

Surfactant Basics

56

Surfactants Surfactants = Surface Active Agents

Small quantities of surfactants change the properties of systems by acting at interfaces (e.g. air-water, air-oil,etc)

Surfactants – End Use Applications

Some examples of areas of surfactant use are in hard surface cleaning, laundry, dishwashing, personal care, agrochemicals, paints & coatings, textile processing, etc.

What do surfactants do?

They help un-like things go together (usually water and oil)

• Create stable emulsions in creams, lotions, etc

• Lifting oily dirt from clothes, skin or hair

• Helping formulations fluids stay together

(such as metalworking fluids, paints & coatings…)

• Keeps pesticides dispersed in agricultural sprays and wets

hydrophobic surfacesDispersions

Emulsions

• Two different groups in one molecule

Tail or hydrophobe: Branched (e.g. Exxal alcohols) or linear alkyl, Alkylaryl

(nonylphenyl, alkylphenyl)

• Anionic : SO3-, COO-, (CH2CH2O)nSO3

- (sulfates, sulfonates, etc)

• Nonionic : (CH2CH2O)n-H (or EO/PO)

• Cationics : NH2, CONH2, NH4+ (Amines, etc)

• Zwitterionic or Amphoteric : RN+H2CH2COO-

(sultaines, betaines, etc)

(Water-liking)

Surfactants are Amphiphilic molecules

Hydrophobicmoiety (oil-liking)

Commercial Alcohol Ethoxylation with KOH Catalyst

Sources of Water in Ethoxylation Process

• Water from the alcohol

• Water from 45% KOH catalyst

• Water from alkoxide formation

Polyethylene Glycol (PEG) Formation in Commercial Alcohol Ethoxylation

0.0

1.0

2.0

3.0

4.0

5.0

6.0

7.0

8.0

9.0

10.0

0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

Wt

%

Mole EO/mole

Exxal 11 Alcohol Ethoxylate (7EO)

Exxal 11

EO distributions

By gas chromatography

Alcohol Ethoxylates Characterization and Analysis

AE Characteristics AE Specifications

Weight % EO Level Hydroxyl Number

Average Moles EO Color, APHA (or Hazen)

Ave. MW AE pH

HLB Moisture, ppm

EO Adduct Distribution Residual EO, ppm

Weight % Free Alcohol Cloud Point *

Residual Metal Ions Weight % PEG Level *

Effect of Degree of Ethoxylation on Key Properties of Alcohol Ethoxylates

• Detergency• Increases as the number of moles of EO increases for most alcohols (with slight variation that is

dependent on alcohol chain length)

• Foam Height• Increases as the number of moles of EO increases

• Water Solubility• Increases as the number of moles of EO increases

• Viscosity• Increases as the number of moles of EO increases

Hydrogen bonding of AE to water

Typical Surfactant Specifications & Properties

• Density• Cloud point• Pour point• Flash point• HLB number• Surface tension• Interfacial tension• Viscosity• Foaming• Wetting

Industry ApplicationST / IFT* decrease

Fast Wetting

EmulsificationCaustic Stability

Phase Behavior

Low Foaming

Textiles

Pretreat X X X X

Bleaching X X

Dyeing X

Ag ChemAdjuvants X X X X

Suspension Concentrates X X X X

Emulsion Polymerization X

I&I CleaningWetting agents X X X X

Detergents X X X X X

Leather Wetting, degreasing X X X

Oil & Gas

EOR X X X

Emulsion breakers X

Dispersants X X

Mining Frothers, flotation X X

Household

Laundry X X X X

Hard Surface X X X X

Dishwashing X

Personal Care Shampoo X

Matching Performance to Application

67

Property Units Method

Cloud point in water °C CI-TM1

Surface tension mN/m CI-TM8

Gel phase (by rheometry)Temp / wt %

surfactant curvesCI-TM5

CMC critical micelle concentration (20°C)

mg/L mmole/L

Derived from surface tension curves (CI-TM8)

Wetting time in water seconds CI-TM3 (Draves test)

Wetting time in 1% NaOH seconds CI-TM3 A (Draves test)

Foam height mm CI-TM6

Dynamic surface tension msCI-TM7 (Maximum bubble

pressure)

Pour point °C ASTM D5950

Ethoxylate distributions GC 26.2.1 (ExxonMobil)

CI-TM refer to ExxonMobil methods

Methods used