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ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO GREEN HIGH VALUE PRODUCTS K. Vanbroekhoven & W. Dejonghe, VITO European workshop: Inclusion of primary production in biobased value chains Brussels, 20/02/2020 19/02/2020 ©VITO – Not for distribution 1

ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

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Page 1: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO GREEN HIGH VALUE PRODUCTS

K. Vanbroekhoven & W. Dejonghe, VITOEuropean workshop: Inclusion of primary production in biobased value chainsBrussels, 20/02/2020

19/02/2020

©VITO – Not for distribution 1

Page 3: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM AGRICULTURAL COMPOUNDS AVAILABLE IN EUROPE

19/02/2020

©VITO – Not for distribution 3

▪ Agricultural compounds used in ester synthesis

Vegetable oilAnimal fat

Long chain fatty acids: > C12

Page 4: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

VEGETABLE OILS PRODUCED IN EUROPE

19/02/2020

©VITO – Not for distribution 4

2017: EU36 Mton seed → 12 Mton oil

Seeds Rape and turnip rape Sunflower Soya

https://ec.europa.eu/eurostat/statistical-atlas/gis/viewer/?year=&chapter=12&mids=BKGCNT,BKGNT22016,C12M04&o=1,1,1&ch=AGF,AGR&center=49.50449,27.3328,3&lcis=C12M04&Kumar et al.? 2016, dx.doi.org/10,1016/B978-0-12-802980-0,00019-5

M = million

200 Mton

Coconut oil: C12

BUT: - 80 % food + 15 % biodiesel- C18: Oleic + linoleic acid, no C16 + C12

Page 5: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ANIMAL FAT PRODUCED IN EUROPE

19/02/2020

©VITO – Not for distribution 5

Total production of different categories of animal fats in EU

Destination of edible and Cat 3 fat in 2014 in EU.

1,5 Mton animal fat/yearBeef, pig and poultryPalmitic, oleic, stearic acid

0,6 Mton animal fat/year used in oleochemical industry (40 %) to make:

- fatty acids- fatty alcohols- glycerol

Source: EFPRA

M = million

Page 6: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM AGRICULTURAL COMPOUNDS AVAILABLE IN EUROPE

19/02/2020

©VITO – Not for distribution 6

▪ Agricultural compounds used in ester synthesis

Long chain FA

Acrylic acidMethacrylic acid

Short chain FA

Page 7: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM AGRICULTURAL COMPOUNDS AVAILABLE IN EUROPE

19/02/2020

©VITO – Not for distribution 7

▪ Biomass used in ester synthesis

Short chain FALong chain FA(metha)crylic acid

Natural Petrochemical

Alcohol

(Poly)Glycerol

Sugar

Page 8: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM AGRICULTURAL COMPOUNDS AVAILABLE IN EUROPE

19/02/2020

©VITO – Not for distribution 8

▪ Agricultural compounds used in ester synthesis

AlcoholGlycerol: 2,2 Mton from biodiesel + FASugar

Natural Petrochemical

Short chain FALong chain FA(metha)crylic acid

M = million

Page 9: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SUGAR PRODUCTION IN EUROPE

19/02/2020

©VITO – Not for distribution 9

Cereals2017: 310 Mtons217 Mtons starch (70%)

Sugar beet2018: 120 Mtons18 Mtons sucrose (15%)

Potatoes2018: 52 Mtons8 Mtons starch (15%)

https://ec.europa.eu/eurostat/statistics-explained/index.php/Agricultural_production_-_crops#Potatoes_and_sugar_beet

https://ec.europa.eu/eurostat/statistical-atlas/gis/viewer/?year=&chapter=12&mids=BKGCNT,BKGNT22016,C12M03&o=1,1,1&ch=AGF,AGR&center=49.50449,27.3328,3&lcis=BKGNT22016&

M = million

Sugar mainly used in food14 kTon sucrose esters/2015

Page 10: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM AGRICULTURAL COMPOUNDS AVAILABLE IN EUROPE

19/02/2020

©VITO – Not for distribution 10

▪ Agricultural compounds used in ester synthesis

AlcoholGlycerolSugar

Natural Petrochemical

Short chain FALong chain FA(metha)crylic acid

Short chainLong chain > C6

Page 11: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM AGRICULTURAL COMPOUNDS AVAILABLE IN EUROPE

19/02/2020

©VITO – Not for distribution 11

▪ Agricultural compounds used in ester synthesis

AlcoholGlycerolSugar

Natural Petrochemical

Short chain FALong chain FA(metha)crylic acid

Short chainLong chain > C6

Page 12: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM AGRICULTURAL COMPOUNDS AVAILABLE IN EUROPE

19/02/2020

©VITO – Not for distribution 12

▪ Agricultural compounds used in ester synthesis

AlcoholGlycerolSugar

Natural Petrochemical

Short chain FALong chain FA(metha)crylic acid

Short chainLong chain > C6

Page 13: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

CAN AN ALTERNATIVE PROCESS BE DEVELOPED FOR ESTER SYNTHESIS?

13

Ref: Schumacher and Thum, Chem.Soc.Rev., 2013, 42, 6475

Green & sustainable process

Natural & organic products

Esterification catalyzed by Lipase to synthesize fatty acid esters

Page 14: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

INDUSTRIALLY DRIVEN ESTER RESEARCH AT VITO: THE PROCESS

14

• Model based assessment

• Techno –economical assessment

• Sustainability analysis

• CO2 emission• Energy usage

ProcessConceptualization

Lipase selection

Process in mLscale

Processdevelopment (1-5 L scale)

Techno-economicevaluation

Pilot testing

▪ Free / Immobilized

▪ Reaction conditions

▪ Enzyme kinetics

▪ Pure & technical grade substrates

▪ Definitions of figures of merit▪ Yield▪ Productivity▪ Specific & total

productivity

▪ Process conditions

▪ Process intensification: In situ water removal

▪ Enzyme stability & Re-use

▪ Use of model to combine technical and economic data

▪ Identification of most influential parameter(s) on process economics

▪ At own or industrial site

▪ Mobile Pilot equipment

• Lipase used as biocatalyst for solvent free synthesis of esters using fatty acid and alcohol as substrates

• Infrastructure for batch and (semi) continuous processes (upscaling from 100 mL to approximately 5 L)

• Water removal approaches e.g. pervaporation for process intensification/zeolites

• Process up-scale to pilot scale with coupled hydrophilic pervaporation

Page 15: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

INDUSTRIALLY DRIVEN ESTER RESEARCH AT VITO: IN PICTURES & KG SCALE

15

Initial experiments in mL scale

Lab scale 3L reactor Lab scale PV set-up Pilot scale PV set-up

Page 16: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

1/ EMOLLIENTS: UPSCALED PROCESS WITH MEMBRANE ASSISTED WATER REMOVAL

Confidential 16

Solvent free Kg scale ester production process

Coupled with PV

Various Kg scale batches tested

Enzyme reusability and membrane stability

Product purification and application testing

0

0,5

1

1,5

2

2,5

3

Wat

er (

%)

• High conversion of fatty acids• Solvent free: High product yields• No loss of substrates or products during

water removal• Very stable enzyme and membrane

performance

Page 17: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

INnovative Chemoenzymatic InTEgrated processes – fosters competitiveness of the European green chemistry industry

A MULTI-STAKEHOLDERS PROJECT

3 universities and research organizations 2 SMEs 2 large

industries 1 innovation cluster

PROJECT DURATION:

48 months, from September 2019 to August 2023

INCITE aims to prompt a transition to a more flexible and sustainable chemistry by taking novel integrated upstream and downstream processing paths involving flow chemistry and membrane technology in two chemo-enzymatic processes to an industrial level

FOLLOW US

BUDGET:

Total cost: € 17.4 MEuropean Union’s Horizon 2020 Research and

Innovation Programme contribution: € 13.3 MOBJECTIVES

Contact: [email protected]

Page 18: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

MONO (DI)ACYLGLYCEROLS AND POLYGLYCEROLS

Voettekst invulling 18

Image source:chemicalsinourlife.echa.europa.eu Image source: whattech.com

Mono (di)acylglycerol

Polyglycerol ester

Organic compoundResource instead of feed additive

Page 19: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

SUGAR ESTERS

19

Advantage enzymatic process:- Mild process: DSP- Regioselectivity: Degree esterification- Green solvent: sustainable + re-usable

Use of mono-, oligosaccharides and agricultural side stream

Page 20: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS

SYNTHESIS ORGANIC ESTERS FROM CHEMICALS PRODUCED IN EUROPE

19/02/2020

©VITO – Not for distribution 20

▪ Primary substrates used in ester synthesis

Fatty acidVegetable oilAnimal fat

AlcoholGlycerolSugar

Natural Petrochemical

Page 21: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

Powered by: TNO & VITO

2/19/2020 21

Horizons Feedstock Conversion Technology Bio-Aromatics Applications

Sugar to Bio-Aromatics

C5 Sugars/Furfural

Biomass residues &Recycle streams

Specialty€€€

Lignin to Bio-Aromatics

Thermochemical Conversion of

Biomass to Bio-Aromatics

Diels-Alder

Catalytic Depolymerization

Pyrolysis

Gasification Bulk€

Lignin

Page 22: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERIFICATION OF PHENOL ALIKES FROM LIGNIN DEPOLYMERIZATION

19/02/2020

©VITO – Not for distribution 22

OH

OH

O

O

OH

O

OH

OH

O

O

OH

O

O

OH

O

S lignin, R1 = OMe, R2 = -OMe

H lignin, R1 = H, R2 = -H

G lignin, R1 = H, R2 = -OMe

OH

OH

R1

R2

a)

biosynthesis

OH

O

OH

OH

O

OH

O O

dimeric

monolignol

derivatives

oligomeric

monolignol

derivatives

OH

O O

OH

PG DCA

PS DSA

hydroboration/

oxidationreduction

catalytic

hydrogenation

LIGNIN OIL

OH

R1

R2

O

OH

OR

1

R2

OH

OR2

OH

O R1

OOH

OHO

R1

R2

OH

lignin

OR

1R

2

OHOH

OH

R2

O

O

O

R1

R2

OH

O

R1

R2

OH

OH

O

R1

R2

OH

O

R1

R2

OH

OH

OH

O

R1

R2

OHlignin

O

R1

OH

lignin

b)LIGNIN

catalytic

hydrogenationDCA

CHEMICAL SYNTHESIS

OH

O

CH3

OH

OH

O

CH3

O

O

CH2

R

FRP (AIBN)

OH O

CH3

O

O

R1

R2

Rn

Novozyme 435

5A MS, Methyl Methacrylate

polymerization

Enzymatic conversion

Page 23: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

23

ESTERS OF ALCOHOL DERIVATIVES FROM C5 SUGARS

4-methoxybenzyl alcohol

Furfuryl alcohol

Tetrahydrofurfuryl alcohol

Page 24: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

ESTERS OF MONOTERPENE ALCOHOLS

a-pinene

b-pinene

Pine forest

Geraniol

Citronellol

Linalool

Flavor & Fragrance

Acetate esters

Figure 1: Acetate esters used as flavours and/or fragrances and investigated in VITO

Figure 1: Acetate esters used as flavours and/or fragrances and investigated in VITO

(meth)acrylate esters

Page 25: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

OLIGOSACCHARIDES

BIOMASS DERIVED POLYSACCHARIDES INTO HIGH-PERFORMANCE FUNCTIONALINGREDIENTS

19/02/2020

©VITO – Not for distribution 25

Properties:▪ Prebiotic (FOS, GOS, POS, MOS)

▪ Antioxidant (XOS)

▪ Antimicrobial (COS)

▪ Anti-coagulant (COS)

▪ Plant elicitors (POS, COS,

carrageenan)

▪ Plant biostimulant (COS,

carrageenan)

Oligo’s from algae

POS

COS

ChitinChitosan

StarchUlvan, carrageenan, laminarin, fucoidan

Lactose

Mannan

MOS

Confidential

Investigatedby VITO

XOS

GOS

OLIGOCAR

Page 26: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

MOOV - MOBILISATION AND OPTIMISATION OF VALUE CHAINS

19/02/2020

©VITO – Not for distribution 26

OPTIMISED VALUE CHAINS

INTERACTIVE DASHBOARDS

Page 27: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

TAKE HOME MESSAGE

19/02/2020

©VITO – Not for distribution 27

▪ European agricultural feedstocks in the synthesis of biobased esters

▪ Biobased short chain alcohols and fatty acids result in 100 % biobased esters

▪ The interest in the market of enzymatically produced biobased esters ↑

▪ VITO developed a sustainable enzymatically based technology to produce a

portfolio of esters & can optimize the value chain

▪ Call for participation in our developments:

▪ Your feedstocks for our enzymatic ester synthesis

▪ Screening functionality of esters in your application

Page 29: ENZYMATIC CONVERSION OF RENEWABLE BIOMASS INTO … · 2. SMEs . 2. large industries . 1. innovation cluster. PROJECT DURATION: 48. months, from September 2019 to August 2023 INCITE

COLLEAGUES

19/02/2020

©VITO – Not for distribution 29

MOOV teamEnzyme team

Y. Satyawali W. Van Hecke L. Cauwenberghs H. Elslander A. De Meyer R. Guisson

Thanks for your attention!

M. Martinez Garcia