Valorisation of wheat bran into surfactant molecules by Caroline - - PowerPoint PPT Presentation

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Valorisation of wheat bran into surfactant molecules by Caroline - - PowerPoint PPT Presentation

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Valorisation of wheat bran into surfactant molecules by Caroline Rmond (INRA/URCA FARE), Magali Deleu (ULige), Yamini Satyawali (VITO) Representing the ValBran consortium www.valbran.eu Facebook page: @Valbiom @interregFranceWallonieVlaanderen

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Valorisation of wheat bran into surfactant molecules

by Caroline Rémond (INRA/URCA FARE), Magali Deleu (ULiège), Yamini Satyawali (VITO) Representing the ValBran consortium

www.valbran.eu

Facebook page: @Valbiom @interregFranceWallonieVlaanderen #ValBran LinkedIn & Twitter: ValBiom asbl #ValBran

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 1

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Interreg France‐Wallonie‐Vlaanderen

ONDERZOEK EN INNOVATIE RECHERCHE ET INNOVATION

  • 1. Versterken van het onderzoek en de innovatie van de

grensoverschrijdende zone in de strategische sectoren en de sectoren met een sterke complementariteit | Accroissement de la recherche et de l’innovation de la zone transfrontalière dans les secteurs stratégiques et les secteurs à forte complémentarité

  • 2. Grotere overdracht en verspreiding van goede praktijken in de strategische

sectoren en de sectoren met een sterke complementariteit in de grensoverschrijdende zone | Accroissement du transfert et de la diffusion des bonnes pratiques innovante dans les secteurs stratégiques et à forte complémentarité de la zone transfrontalière Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 2

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Alkyl glycosides and sugar esters, non‐ionic surfactants of interest

Al Alkyl kyl poly polygly glycoside ides (A (APG PG)

World market: 100,000 T/year Emulsifiers, foaming agents, wetting agents for cosmetics, detergents, phytosanitary

Sug Sugar ester ers

World market: 10,000 T/year Emulsifiers for cosmetics and food Chemically produced: limited degree of polymerization (DP) for the glycon part which impacts hydrophilic‐lipophilic balance, generation of undesirable molecules

AppycleanTM (Wheatoleo), OramixTM, MontanovTM (Seppic), … CrodestaTM (Croda), products from Sisterna, …

Non‐ionic surfactants ≈ 50 % of the total surfactant market in Europe Growing interest for surfactants from renewable ressources: biodegradability, non toxic for humans and environment

3

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SLIDE 4
  • Wheat bran, agricultural co‐product from

milling industries and 1G bioethanol industries

  • Main use: food (fibers) and feed

Surfactants for high added‐value applications

Cosmetics, food…

Enzymatic processes environmentally friendly

  • Cellulose and xylans fractionation
  • Functionalization of sugars from fractionation

Enzymatic processes environmentally friendly

  • Cellulose and xylans fractionation
  • Functionalization of sugars from fractionation

Wheat bran residues (+ cellulases‐hemicellulases): feed

Wheat bran valorisation into surfactants

Cellulose Xylans Enzymatic hydrolysis

glucose xylose

Enzymatic functionalization

Fatty acid, alcohol

Alkyl glycosides or sugar esters

Alkyl glycosides and sugar esters, non‐ionic surfactants of interest

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 4

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SLIDE 5

Partners

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 5

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SLIDE 6

Overview of the project

Cosmetics, phytosanitaries, food‐feed additives, detergents

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Enzymatic synthesis of alkyl xylosides

xylanase xylanase

pentan‐1‐ol / H2O 48h, 50°C

Wheat bran Ex Example: ample: sy synthesis of pen pentyl yl ‐D‐xyl xylosi sides des

Enzymatic transglycosylation

No pretreatment

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 7

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Enzymatic synthesis of alkyl xylosides

  • Synthesis efficient with wheat bran from Bi

Biow

  • wanz

anze (Wanze, Belgium) and from ADM ADM (Pomacle Bazancourt, France)

  • Op

Optim timization tion of

  • f the

the tr transgly ansglycosyla lation tion reaction action conditions: nditions:

  • Pentyl ‐D‐xylosides : 4.9

4.9 g/ g/L 450 450 mg mg pentyl ‐D‐xylosides / g xylans present in wheat bran  equivalent to transglycosylation performed from commercial xylans

Ochs et al. Green Chem., 2011, 13, 2380

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Enzymatic synthesis of alkyl xylosides

  • Reaction efficient for the synthesis of alkyl ‐D‐xylosides with C chain

chain lengh lenghts from C3 to to C10 C10 (propan‐1‐ol to decan‐1‐ol)

  • Up

Up‐sc scalin aling of the the re reaction in a 2 lit liter ers react eactor

  • r

 same yields of transglycosylation

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 9

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Properties of the pentyl xylosides

Surf Surface ace‐activ active pr properti

  • perties

es

  • Capacity to decrease the surface tension (CAC)
  • Aggregation behaviour: Critical aggregation concentration (CAC)

(CAC, CAC)

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Pentyl -D- xylosides mixture CAC (mg.L-1) CAC (mN/m) From WB 1 3089 59 From WB 2 2150 39

Properties of the pentyl xylosides

Surface‐active properties ‐ Results

  • Poor surface‐active properties – longer alkyl chain (C8 or C10)
  • But potential hydrotrope properties (under investigation)

Literature (Bouxin et al., 2010) Octyl /‐D‐xylosides DP1 : CMC = 950 mg.L‐1

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Enzymatic synthesis of sugar esters

1st step : production of glucose and xylose hydrolysates from wheat bran Enzymatic hydrolysis

D‐glucose D‐xylose + H2O, 50°C

Hydrolysate rich in glucose and xylose Starch and wheat bran residues

According to enzyme loading and reaction duration: 50 to 100% of glucose and xylose released

Wheat bran from BIO BIOWANZE (Wanze, BE) and from ADM ADM (Pomacle‐Bazancourt, FR)

No additives

Wheat bran

No pretreatment

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Enzymatic synthesis of sugar esters

1st step : production of glucose and xylose hydrolysates from wheat bran Optimization of conditions pretreatment by PLS‐Surface Response Design

Prescribed solution: Room Temperature Ionic liquid (RTIL) pretreatment prior enzymatic hydrolysis Scientific and technological lock: recalcitrance properties of wheat bran

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 13

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Enzymatic synthesis of sugar esters

1st step : production of glucose and xylose hydrolysates from wheat bran

Competitive yields achieved: Yglucose = 83 % and Yxylose = 95 %

Response surface plots of sugar (A: glucose, B: xylose) release after enzymatic hydrolysis

Optimal conditions of pretreatment: diluted‐[C2mim][OAc] in water (10 % v/v) at 150 °C for 40 min Araya‐Farias et al. (2019). Frontiers in Chemistry. 7:585

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  • Sugars conversion: 80

80‐100% 100%

D‐glucose D‐xylose

Methyl laurate or lauric acid 2M2B, molecular sieves

+

Lipase

  • Modulation of glc

glc ester ers an and xyl xyl ester ers ra ratios and and of

  • f mo

mono no‐ and and di dies esters ra ratios according to D‐glc/D‐xyl ratio (hydrolysate) and reaction conditions

Méline et al. Enz. Microbial. Technol. 2018

Enzymatic synthesis of sugar esters

2nd step : production of sugar esters from glucose and xylose hydrolysates

Example: synthesis of laurate glucose and xylose esters

  • (Trans)esterification efficient with fatty acids and fatty acids esters with

C chain chain leng enght from C8 to to C18 C18

O HO HO OH OH O O

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Properties of the sugar esters

Surface‐active properties

  • Structure‐activity relationships of purified molecules

from (trans)esterification reactions

1 or 2 chains 8 →18 C Xylose 1 → 4

XC8

Xylose octanoate monoester

X(C8)2

Xylose octanoate diester

XC12

Xylose laurate monoester

XC14

Xylose myristate monoester

XC18

Xylose stearate monoester

X2C12

Di-Xylose laurate monoester

X3C12

Tri-Xylose laurate monoester

X4C12

Tetra-Xylose laurate monoester

XyC12

Xylo-oligosaccharides laurate monoesters

Number of alkyl chains Length of alkyl chains Number of xylose residues Ester link

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Properties of the sugar esters

Surface‐active properties

  • Structure‐activity relationships of purified molecules‐ Results

Middle chain length

Number of alkyl chains Length of alkyl chains Number of xylose residues

100 200 300 400 500 XC8 XC12 XC14 XC18

CAC (mg.L‐1)

10 20 30 40 50 XC8 XC12 XC14 XC18

CAC (mN/m)

100 200 300 400 500 XC8 X(C8)2

CAC (mg.L‐1)

10 20 30 40 50 XC8 X(C8)2

CAC (mN/m)

100 200 300 400 500 XC12 X2C12 X3C12 X4C12 XyC12

CAC (mg.L‐1)

10 20 30 40 50 XC12 X2C12 X3C12 X4C12 XyC12

CAC (mN/m)

Two alkyl chains Limited number of xylose residues

The best candidate: X(C8)2 Xylose octanoate diester

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 17

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SLIDE 18

Properties of the sugar esters

Surf Surface ace‐acti active pr properties

  • perties
  • Structure‐activity relationships of mixtures from (trans)esterification

reactions obtained from wheat bran

D-glc and D-xyl lauryl esters mixture CAC (mg.L-1) CAC (mN/m)

Mixture with mono-esters mainly

44.4 24.4

Mixture with di-esters mainly

48.3 27.5

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Properties of the sugar esters

Potential as antibacterial agent

  • Permeabilization of bacterial plasma membrane

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Properties of the sugar esters

Potential as antibacterial agent

  • Permeabilization of bacterial plasma membrane ‐ Results
  • 20

20 40 60 80 100 5 10 15 20 Permeability (%) Concentration (µM) XC8 XC12 XC14 XC18

  • 20

20 40 60 80 100 5 10 15 20 40 60 80 Permeability (%) Concentration (µM) XC8 X(C8)2

  • 20

20 40 60 80 100 5 10 15 20 Permeability (%) Concentration (µM) XC12 X2C12 X3C12 X4C12 XyC12

Number of alkyl chains Length of alkyl chains Number of xylose residues

  • Moderate permeability of bacterial membranes
  • The best candidates : XC14 and X(C8)2

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019 20

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TEA ‐ TECHNO‐ECONOMIC ASSESSMENT

by Yamini Satyawali VITO, Flemish Institute for Technological Research 21

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Techno‐economic assessment

22 Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019

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Techno‐economic assessment – Market study

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  • Market study collects information on e.g.
  • Market demand and growth
  • Product characteristics
  • Prices
  • Competitors
  • Legal aspects
  • …

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019

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Techno‐economic assessment – Technical assessment

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  • Technical Assessment
  • Process Flow Diagram
  • Mass and Energy balances are calculated

dynamically for each step.

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019

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Techno‐economic assessment – Economic assessment

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  • Economic Assessment

Calculation of:

  • CAPEX
  • OPEX
  • Revenues

Integrated with Mass and Energy balance

Result:

  • Production cost
  • Investment criteria such as Net Present Value,

Internal Rate of Return and (Discounted) Payback Period

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019

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Techno‐economic assessment – Uncertainty

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  • Uncertainty analysis
  • Many uncertainties in technical and economic

parameters

  • Monte Carlo assessment to see which parameters

have the highest impact on e.g. the production cost

  • r NPV

 For the most important parameters: Can we improve them?

  • If yes, how would it impact the viability?
  • If no, do we have alternatives available?

Ghent, Bio Base Europe Pilot Plant ‐ 7.11.2019

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Surfactants from ValBran can be provided to companies for evaluation

Bio‐based surfactants from ValBran: Opportunities for testing applications

Under Under pr progr

  • gress:

ss: technologic chnological trans nsfer ‐ WP WP6

  • Economical feasability (TEA)
  • Environmental impact (LCA)

Contact: caroline.remond@univ‐reims.fr

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Avec le soutien du Fonds européen de développement régional, de la Région Grand Est, de la Wallonie et de la Province West‐Vlaanderen. Met steun van het Europees Fonds voor Regionale Ontwikkeling (EFRO), Grand Est, Wallonië en Vlaanderen.

Janvier 2017 – Décembre 2020 Januari 2017 – December 2020 Coût total : 1.745.826,28 € | Financement FEDER : 872.913,12 € Totale kost : 1.745.826,28 € | EFRO‐financiering : 872.913,12 €

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Merci pour votre attention Dank u wel voor uw aandacht

www.valbran.eu info@valbran.eu

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