Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Enzymatic catalysis as a versatile tool for the synthesis of multifunctional, bio-based oligoester resins
KTH, School of Biotechnology (BIO), Industrial Biotechnology.ORCID iD: 0000-0003-2644-0752
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0003-3201-5138
KTH, School of Biotechnology (BIO), Industrial Biotechnology.ORCID iD: 0000-0002-2993-9375
2016 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 18, no 7, 1923-1929 p.Article in journal (Refereed) Published
Resource type
Text
Abstract [en]

The use of enzymes as selective catalysts for processing renewable monomers into added value polymers and materials has received increased attention during the last decade. In the present work Candida antarctica lipase B (CalB) was used as catalyst in one-pot routes to synthesise multifunctional oligoester resins based on an epoxy-functional omega-hydroxy-fatty acid (EFA) extracted from birch bark. The chemoselective enzymatic process resulted in three different EFA-based telechelic oligomers with targeted molecular weights; containing maleimide, methacrylate or oxetane as end-groups, respectively. The enzyme catalysed synthesis of the maleimide and the oxetane telechelic oligomers reached full conversion of monomers (>95%) after 2 h. In the case of methacrylate functional oligomer the EFA monomer reached full conversion (>98%) after 2 h but the integration of the methacrylate moiety took more than 10 h. This was due to a rate limiting reaction path using ethylene glycol dimethacrylate as substrate. The oligomer products were characterised by NMR, MALDI-TOF-MS and SEC.

Place, publisher, year, edition, pages
The Royal Society of Chemistry , 2016. Vol. 18, no 7, 1923-1929 p.
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-185665DOI: 10.1039/c5gc02597dISI: 000372981400012Scopus ID: 2-s2.0-84962377189OAI: oai:DiVA.org:kth-185665DiVA: diva2:923404
Funder
EU, FP7, Seventh Framework Programme
Note

QC 20160426

Available from: 2016-04-26 Created: 2016-04-25 Last updated: 2017-08-22Bibliographically approved
In thesis
1. Sustainable synthetic pathways towards the formation of bio-based polymeric materials
Open this publication in new window or tab >>Sustainable synthetic pathways towards the formation of bio-based polymeric materials
2016 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Increasing environmental and social awareness arising from the use of oil as main source of raw materials, has awaken the interest of many scientists to explore new synthetic pathways for polymer production. These new approaches embrace the use of alternative feedstock and sustainable synthetic routes aiming for enhancing biodegradability and recyclability. This shift towards more benign strategies is considered positive from different perspectives. Through the exploitation of bio-based feedstock it is possible to minimize the carbon foot print at the same time as new tools for material formation are provided. The use of selective catalysts reduces the formation of side-products, minimizes or avoids the use of solvents and diminish energy consumption. At the same time, new polymeric structures can be formed in terms of functionality and architectures.  

The work herein presented have focused on the development of sustainable synthetic routes for the formation of bio-based polymeric materials with targeted properties. In order to afford this, two bio-sources have been explored for the retrieval of different epoxy-fatty acids, i.e. outer birch bark and vegetable oils. In order to be able to tailor the final material properties and thus be able to target specific applications, we have relied on the selectivity of lipases to preserve the epoxy-functionalities during synthesis. Through the design of specific polymer architectures, e.g. telechelic oligomers, and branched or linear macromers, different degrees of functionality could be prepared. By covalently reacting the epoxy groups through different polymerization techniques, polymer networks were achieved. The proposed synthetic approach resulted in polymeric materials with wide variety of properties ranging from functional networks, to high Tg materials and adhesives, prepared all from renewable sources. This also proved the benefits of the use of lipases in synthesis of polymers for material applications.  

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2016. 61 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2016:38
Keyword
bio-based, polymers, materials
National Category
Polymer Technologies
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-195079 (URN)978-91-7729-173-2 (ISBN)
Public defence
2016-12-02, F3, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20161101

Available from: 2016-11-01 Created: 2016-11-01 Last updated: 2016-11-11Bibliographically approved
2. Building blocks for polymer synthesis by enzymatic catalysis
Open this publication in new window or tab >>Building blocks for polymer synthesis by enzymatic catalysis
2017 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The search for alternatives to oil-based monomers has sparked interest for scientists to focus on the use of renewable resources for energy production, for the synthesis of polymeric materials and in other areas. With the use of renewable resources, scientists face new challenges to first isolate interesting molecules and then to process them.

Enzymes are nature’s own powerful catalysts and display a variety of activities. They regulate important functions in life. They can also be used for chemical synthesis due to their efficiency, selectivity and mild reaction conditions. The selectivity of the enzyme allows specific reactions enabling the design of building blocks for polymers.

In the work presented here, a lipase (Candida antarctica lipase B (CalB)) was used to produce building blocks for polymers. An efficient route was developed to selectively process epoxy-functional fatty acids into resins with a variety of functional groups (maleimide, oxetane, thiol, methacrylate). These oligoester structures, based on epoxy fatty acids from birch bark and vegetable oils, could be selectively cured to form thermosets with tailored properties.

The specificity of an esterase with acyl transfer activity from Mycobacterium smegmatis (MsAcT) was altered by rational design. The produced variants increased the substrate scope and were then used to synthesize amides in water, where the wild type showed no conversion. A synthetic procedure was developed to form mixed dicarboxylic esters by selectively reacting only one side of divinyl adipate in order to introduce additional functional groups.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2017. 61 p.
Series
TRITA-BIO-Report, ISSN 1654-2312 ; 2017:15
Keyword
Enzyme, Enzyme Engineering, Biocatalysis, Lipase, CalB, MsAcT, Substrate specificity, Selectivity, Polymer Chemistry, Polymer Synthesis
National Category
Biocatalysis and Enzyme Technology
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-212499 (URN)978-91-7729-494-8 (ISBN)
Public defence
2017-09-22, Kollegiesalen, Brinellvägen 8, Stockholm, 10:00
Opponent
Supervisors
Note

QC 20170823

Available from: 2017-08-23 Created: 2017-08-22 Last updated: 2017-08-23Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Search in DiVA

By author/editor
Semlitsch, StefanTorron, SusanaJohansson, MatsMartinelle, Mats
By organisation
Industrial BiotechnologyCoating Technology
In the same journal
Green Chemistry
Polymer Chemistry

Search outside of DiVA

GoogleGoogle Scholar

Altmetric score

Total: 207 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf