Novel modified oils enabled by metathesis

Frederyk Ngantung

May 2017

Copyright 2017, Elevance Renewable Sciences, Inc. All rights reserved in this presentation as a whole and the individual slides and content thereon.

AgendaOlefin metathesis of plant oils

Novel modified oils

Summary

2

• Achieved with hydrocarbon feedstocks ONLY• High pressure and temperatures

• Achieved with renewable oils (lipids, fats)• Low pressure and temperatures

Propylene

Ethylene 2-butene

Propylene

A

B

C

D

B DA C

Traditional Metathesis Catalyst Proprietary Metathesis Catalyst

1-decene

9-dodecenoic acid methyl ester

Methyl oleate

1-butene

A B

C D

BD

C A

Olefin metathesis of plant oils

3

Robert Grubbs and Richard Schrock’s advances in new metathesis catalysts enabled the use of plant oil feedstock

Nobel Prize-Winning Catalysis

Novel renewable building blocks

4

Plant oil metathesis enables new building blocks never before accessible at scale

Unsaturated C10 Methyl Ester

Unsaturated C12 Methyl Ester

C18 Diester and Diacid

Elevance Proprietary Olefin Metathesis Process

Plant Oil Feedstock

BiorefineryGresik, Indonesia

Capacity: 180,000 MT

Elevance is the first company to commercialize plant oil metathesis at scale.

Modified oil

Oil

AgendaOlefin metathesis of plant oils

Novel modified oils

Summary

5

Many variables are available to manipulate oil structures via metathesis

6

Plant Oil

Metathesis

Modified oils

Various types of oils:SoyCanolaPalmJatropha……

Various process conditions1 2 Tailored materials with tunable: Architectures Viscosities Functionality

Rheology of plant oils is manipulated via metathesis

7

•Viscosity vs temperature was measured on a stress controlled rheometer (DHR-2) using a 40-mm, parallel plates geometry• Constant shear rate (100s−1) was chosen in the common Newtonian region

Temperature, ⁰C

Vis

cosity (

Pa

.s)

Oligomerized Oils

MTAGs

Plant Oils

Plant oil structures can be manipulated via metathesis

8

Plant Oil

General Triglyceride (TAG)

Cross-Metathesis

- olefins

MTAGs1

Self-Metathesis

- olefins

Oligomerized oils2

MTAG is a new type of oil which can be further derivatized through its terminal double bond

9

Plant oils MTAG

Structure

Dynamic viscosity (25o C)

Average molecular

weight

Terminal double bond

(%)

45-60 cPs 120-150 cPs

800-1,000 1,400-2,700

10-30%

Unique site for derivatization

Fatty acid composition

0%

Well defined by nature Unique unsaturated mid-chain, dibasic

+ oligomers

Palm MTAG is solid at room temperature

10

Dynamic viscosity at 25oC (cPs)

NA - solid

NA – solid

60

120

Dynamic viscosity at 50oC (cPs)

25

30

25

50

Palm MTAG

Canola MTAG

Thermal stability of MTAG is similar to that of its corresponding unmodified plant oil

TGA was carried out on TGAQ500 (TA Instruments, DE, USA)

11

0

50

100

150

200

250

300

350

400

450

Canola Canola MTAG Soy Soy MTAG Palm Palm MTAG

Oxidative Decomposition

Temperature at 10% weight lost (oC) Temperature at 50% weight lost (oC)

Plant oil structures can be manipulated via metathesis

12

Plant Oil

General Triglyceride (TAG)

Cross-Metathesis

- olefins

MTAG1

Self-Metathesis

- olefins

Oligomerized oils2

Oligomerized oil is a new type of high molecular weight oil

13

Source: Croda and Oleon

Stand oil

Blown oil

Oligomerized oils

• Produced at high temperatures without air• Carbon-carbon crosslinking• Pale and low acidity• Made from linseed and soybean

• Produced at high temperatures with air• Oxygen is incorporated into the crosslinking bond• Dark and high acidity• Made from linseed, soy, canola, castor

• Elevance’s metathesis technology on plant oils• Tunable molecular weight and viscosity• Light color with no odor • No polar group; ease of emulsification

Oligomerized oil is a tunable pre-polymer that has low viscosity and sufficient reactivity

14

Plant oils Blown oil

Average molecular

weight (Mw)

Iodine value

Terminal double bond

(%)

Gardner color

45-50 cPs(@ 25⁰C)

15,000

110-180Semi-drying to drying

84Non-drying

0% 0%

1-10 6

Oligomerized oils

Dynamic viscosity

100 - 3200 cPs(@ 40⁰C)Tunable

5400(@ 25⁰C)

800-1,000 2,500 - 30,000+Tunable

Tunable

0-10%Unique site for derivatization

4Lighter than

linseed/blown oil

Oligomerized oil has uncompromised low temperature property

15

Wax appearance temperature (oC)

-13 -2.5 -4 -9

Soy OligomerizedOil 1

OligomerizedOil 2

Blown soybean oil

Gardner color 1 4 4 6

Thermal stability of oligomerized oil is similar to that of plant oil and blown oil

TGA was carried out on TGAQ500 (TA Instruments, DE, USA)16

0

50

100

150

200

250

300

350

400

450

Soy Oligomerized oil 1 Oligomerized oil 2 Blown soybean oil

Oxidative Decomposition

Temperature at 10% weight lost (oC) Temperature at 50% weight lost (oC)

Potential application for MTAG and oligomerized oils

17

Personal care Polyurethane

Paints and coatings

Alkyd resins

Lubricating oilsMetal treating

AgendaOlefin metathesis of plant oils

New modified oils

Summary

18

Leverage complementary

capabilities

Creating differentiated

growth opportunities

Reduce development investment

and risk

Progressing mutual

sustainabilitygoals

Collaborative business model

19

Summary: Elevance offers novel modified oils enabled by metathesis

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• Novel modified oils via metathesis offer a valuable option to plant oils

• MTAG is a novel oil that can be further derivatized through its unique terminal double bond

• Oligomerized oil is a tunable pre-polymer that has low viscosity and uncompromised low temperature property

• Elevance is actively seeking partners to evaluate and commercialize our novel modified oil for new applications

Acknowledgments

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• Georgeta Hategan

• Jeremiah Favero

• Dr. Paul Bertin

• Dr. Steve Cohen

• Jeff Duncan

• Michelle Morie-Bebel

• Rusty Pittman

Thank you

Dr. Frederyk NgantungDirector, Business Development+1-630-633-6722+1-415-272-9452Frederyk.Ngantung@elevance.com

Back up slides

C10 and C12 unsaturated methyl esters

24

Unique mid-chain unsaturated esters unlock new performance possibilities

Difunctional (ester & olefin) High purity BiobasedUnique internal & alpha olefins

Derivatize with known ester chemistry

Derivatize with known olefin chemistry

Unsaturation of mid-chain esters offer new properties & reactivity: better solvency, low-temp operability (pour point), higher CMC, better stability, etc.