Fatty Acid-Derived Aliphatic Long Chain Polyethers by a Combination of Catalytic Ester Reduction and ADMET or Thiol-Ene Polymerization

被引:33
作者
Dannecker, Patrick-Kurt [1 ]
Biermann, Ursula [2 ]
Sink, Alexandra [1 ]
Bloesser, Fabian R. [1 ]
Metzger, Juergen O. [2 ]
Meier, Michael A. R. [1 ]
机构
[1] KIT, Str Forum 7, D-76131 Karlsruhe, Germany
[2] Carl von Ossietzky Univ Oldenburg, Carl von Ossietzky Str 9-11, D-26129 Oldenburg, Germany
关键词
ADMET; gallium bromide; polyethers; renewable resources; thiol-ene; ACYCLIC DIENE METATHESIS; RING-OPENING POLYMERIZATION; OMEGA-PENTADECALACTONE; POLYETHYLENE; POLYESTERS; COPOLYMERIZATION; POLYMERS; CLICK; OIL;
D O I
10.1002/macp.201800440
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Aliphatic long-chain polyesters are a common class of renewable polymers and can be obtained by various synthetic routes, most notably from renewable fatty acids. In contrast, for aliphatic long chain polyethers only a few examples are known. Recently, the GaBr3-catalyzed reduction of esters to ethers has been introduced as convenient post-polymerization modification to obtain polyethers directly from polyesters. Here, this reduction is applied to synthesize fatty acid-based omega,omega '-unsaturated diene diether monomers, which are polymerized afterward by thiol-ene or acyclic diene metathesis (ADMET) polymerizations in the "green" solvents methyl-THF (2-methyltetrahydrofuran) and polarclean. After polymerization, the thiol-ene or ADMET polymers are modified by either oxidation or hydrogenation, respectively.
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页数:17
相关论文
共 54 条
[1]   Toxicological Assessment of 2-Methyltetrahydrofuran and Cyclopentyl Methyl Ether in Support of Their Use in Pharmaceutical Chemical Process Development [J].
Antonucci, Vincent ;
Coleman, John ;
Ferry, James B. ;
Johnson, Neil ;
Mathe, Michelle ;
Scott, Jeremy P. ;
Xu, Jing .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (04) :939-941
[2]  
Berg O., 2013, EUR POLYM J, V49, P804
[3]   Regioselectivity of Radical Addition of Thiols to 1-Alkenes [J].
Biermann, Ursula ;
Metzger, Juergen O. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (06) :730-734
[4]   Synthesis of Ethers by GaBr3-Catalyzed Reduction of Carboxylic Acid Esters and Lactones by Siloxanes [J].
Biermann, Ursula ;
Metzger, Juergen O. .
CHEMSUSCHEM, 2014, 7 (02) :644-649
[5]   Reduction of high oleic sunflower oil to glyceryl trioleyl ether [J].
Biermann, Ursula ;
Metzger, Juergen O. .
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2014, 116 (01) :74-79
[6]   ω-Pentandecalactone Polymerization and ω-Pentadecalactone/ε-Caprolactone Copolymerization Reactions Using Organic Catalysts [J].
Bouyahyi, Miloud ;
Pepels, Mark P. F. ;
Heise, Andreas ;
Duchateau, Rob .
MACROMOLECULES, 2012, 45 (08) :3356-3366
[7]   Renewable Polyethers via GaBr3-Catalyzed Reduction of Polyesters [J].
Dannecker, Patrick-Kurt ;
Biermann, Ursula ;
von Czapiewski, Marc ;
Metzger, Juergen O. ;
Meier, Michael A. R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (28) :8775-8779
[8]   1,1,3,3-Tetramethyldisiloxane [J].
Deng, Jia .
SYNLETT, 2011, (14) :2102-2103
[9]   C-13 NMR SPECTRAL INVESTIGATION OF ORGANOSULFUR COMPOUNDS - SUBSTITUENT-INDUCED CHEMICAL-SHIFT (SCS) EFFECTS IN ACYCLIC SATURATED ORGANOSULFUR COMPOUNDS [J].
DYER, JC ;
EVANS, SA .
MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (03) :286-288
[10]   Renewable co-polymers derived from castor oil and limonene [J].
Firdaus, Maulidan ;
Meier, Michael A. R. ;
Biermann, Ursula ;
Metzger, Juergen O. .
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2014, 116 (01) :31-36