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Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation

BACKGROUND: Development of circular economy requires significant advances in the technologies for valorisation of waste, as waste becomes new feedstock. Food waste is a particularly important feedstock, containing large variation of complex chemical functionality. Although most food waste sources ar...

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Autores principales: Plaza, Dorota D, Strobel, Vinzent, Heer, Parminder Kaur KS, Sellars, Andrew B, Hoong, Seng‐Soi, Clark, Andrew J, Lapkin, Alexei A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley & Sons, Ltd 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5575473/
https://www.ncbi.nlm.nih.gov/pubmed/28919656
http://dx.doi.org/10.1002/jctb.5292
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author Plaza, Dorota D
Strobel, Vinzent
Heer, Parminder Kaur KS
Sellars, Andrew B
Hoong, Seng‐Soi
Clark, Andrew J
Lapkin, Alexei A
author_facet Plaza, Dorota D
Strobel, Vinzent
Heer, Parminder Kaur KS
Sellars, Andrew B
Hoong, Seng‐Soi
Clark, Andrew J
Lapkin, Alexei A
author_sort Plaza, Dorota D
collection PubMed
description BACKGROUND: Development of circular economy requires significant advances in the technologies for valorisation of waste, as waste becomes new feedstock. Food waste is a particularly important feedstock, containing large variation of complex chemical functionality. Although most food waste sources are complex mixtures, waste from food processing, no longer suitable for the human food chain, may also represent relatively clean materials. One such material requiring valorisation is cocoa butter. RESULTS: Epoxidation of a triglyceride from a food waste source, processing waste cocoa butter, into the corresponding triglyceride epoxide was carried out using a modified Ishii‐Venturello catalyst in batch and continuous flow reactors. The batch reactor achieved higher yields due to the significant decomposition of hydrogen peroxide in the laminar flow tubular reactor. Integral and differential models describing the reaction and the phase transfer kinetics were developed for the epoxidation of cocoa butter and the model parameters were estimated. Ring‐opening of the epoxidised cocoa butter was undertaken to provide polyols of varying molecular weight (M(w) = 2000–84 000 Da), hydroxyl value (27–60 mg KOH g(−1)) and acid value (1–173 mg KOH g(−1)), using either aqueous ortho‐phosphoric acid (H(3)PO(4) ) or boron trifluoride diethyl etherate (BF(3) ·OEt(2))‐mediated oligomerisation in bulk, using hexane or tetrahydrofuran (THF) as solvents. The thermal and tensile properties of the polyurethanes obtained from the reaction of these polyols with 4,4′‐methylene diphenyl diisocyanate (MDI) are described. CONCLUSION: The paper presents a complete valorisation scheme for a food manufacturing industry waste stream, starting from the initial chemical transformation, developing a process model for the design of a scaled‐up process, and leading to synthesis of the final product, in this case a polymer. This work describes aspects of optimisation of the conversion route, focusing on clean synthesis and also demonstrates the interdisciplinary nature of the development projects, requiring input from different areas of chemistry, process modelling and process design. © 2017 The Authors. Journal of Chemical Technology & Biotechnology published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
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spelling pubmed-55754732017-09-15 Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation Plaza, Dorota D Strobel, Vinzent Heer, Parminder Kaur KS Sellars, Andrew B Hoong, Seng‐Soi Clark, Andrew J Lapkin, Alexei A J Chem Technol Biotechnol In Focus: Research Articles BACKGROUND: Development of circular economy requires significant advances in the technologies for valorisation of waste, as waste becomes new feedstock. Food waste is a particularly important feedstock, containing large variation of complex chemical functionality. Although most food waste sources are complex mixtures, waste from food processing, no longer suitable for the human food chain, may also represent relatively clean materials. One such material requiring valorisation is cocoa butter. RESULTS: Epoxidation of a triglyceride from a food waste source, processing waste cocoa butter, into the corresponding triglyceride epoxide was carried out using a modified Ishii‐Venturello catalyst in batch and continuous flow reactors. The batch reactor achieved higher yields due to the significant decomposition of hydrogen peroxide in the laminar flow tubular reactor. Integral and differential models describing the reaction and the phase transfer kinetics were developed for the epoxidation of cocoa butter and the model parameters were estimated. Ring‐opening of the epoxidised cocoa butter was undertaken to provide polyols of varying molecular weight (M(w) = 2000–84 000 Da), hydroxyl value (27–60 mg KOH g(−1)) and acid value (1–173 mg KOH g(−1)), using either aqueous ortho‐phosphoric acid (H(3)PO(4) ) or boron trifluoride diethyl etherate (BF(3) ·OEt(2))‐mediated oligomerisation in bulk, using hexane or tetrahydrofuran (THF) as solvents. The thermal and tensile properties of the polyurethanes obtained from the reaction of these polyols with 4,4′‐methylene diphenyl diisocyanate (MDI) are described. CONCLUSION: The paper presents a complete valorisation scheme for a food manufacturing industry waste stream, starting from the initial chemical transformation, developing a process model for the design of a scaled‐up process, and leading to synthesis of the final product, in this case a polymer. This work describes aspects of optimisation of the conversion route, focusing on clean synthesis and also demonstrates the interdisciplinary nature of the development projects, requiring input from different areas of chemistry, process modelling and process design. © 2017 The Authors. Journal of Chemical Technology & Biotechnology published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. John Wiley & Sons, Ltd 2017-05-24 2017-09 /pmc/articles/PMC5575473/ /pubmed/28919656 http://dx.doi.org/10.1002/jctb.5292 Text en © 2017 The Authors. Journal of Chemical Technology & Biotechnology published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle In Focus: Research Articles
Plaza, Dorota D
Strobel, Vinzent
Heer, Parminder Kaur KS
Sellars, Andrew B
Hoong, Seng‐Soi
Clark, Andrew J
Lapkin, Alexei A
Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation
title Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation
title_full Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation
title_fullStr Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation
title_full_unstemmed Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation
title_short Direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation
title_sort direct valorisation of waste cocoa butter triglycerides via catalytic epoxidation, ring‐opening and polymerisation
topic In Focus: Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5575473/
https://www.ncbi.nlm.nih.gov/pubmed/28919656
http://dx.doi.org/10.1002/jctb.5292
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