Reductive Amination/Cyclization of Methyl Levulinate with Aspartic Acid: Towards Renewable Polyesters with a Pendant Lactam Unit

被引：14
作者：
Bernhard, Yann [1 ]
Pellegrini, Sylvain [1 ]
Bousquet, Till [1 ]
Favrelle, Audrey [1 ]
Pelinski, Lydie [1 ]
Cazaux, Frederic [2 ]
Gaucher, Valerie [2 ]
Gerbaux, Pascal [3 ]
Zinck, Philippe [1 ]
机构：
[1] Univ Artois, Univ Lille, CNRS,UMR 8181, Cent Lille,ENSCL,UCCS Unite Catalyse & Chim Solid, F-59000 Lille, France
[2] Univ Lille, CNRS, INRA, ENSCL,UMET Unite Mat & Transformat,UMR 8207, F-59000 Lille, France
[3] Univ Mons UMONS, Organ Synth & Mass Spectrometry Lab, 23 Pl Parc, B-7000 Mons, Belgium
来源：
CHEMSUSCHEM | 2019年 / 12卷 / 14期
关键词：
aspartic acid; biobased polyesters; levulinic acid; polymers; reductive amination; CATALYTIC CONVERSION; 5-HYDROXYLEVULINIC ACID; PYRROLIDONE DERIVATIVES; BIODEGRADABLE POLYMERS; GAMMA-VALEROLACTONE; BUILDING-BLOCKS; KETO ACIDS; BIOMASS; CHEMICALS; TRANSFORMATION;
D O I：
10.1002/cssc.201900745
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Environmental regulation and depletion of fossil resources are boosting the search for new polymeric materials produced from biomass. Here, the synthesis of a new diester bearing a pendant lactam unit from methyl levulinate and aspartic acid is reported. The palladium-catalyzed reductive amination/cyclization sequence was carefully optimized to afford the diacid with high yield (>95 %). In a second step, the compound was esterified to give the corresponding diester. The latter monomer was copolymerized with alpha-omega linear diols, yielding polyesters with molecular weights up to 20.5 kg mol(-1).
引用
收藏
页码：3370 / 3376
页数：7
相关论文
共 80 条
[71]   Development of New Carbon Resources: Production of Important Chemicals from Algal Residue [J].
Yamaguchi, Sho ;
Kawada, Yuuki ;
Yuge, Hidetaka ;
Tanaka, Kan ;
Imamura, Sousuke .
SCIENTIFIC REPORTS, 2017, 7
[72]   Production and catalytic transformation of levulinic acid: A platform for speciality chemicals and fuels [J].
Yan, Kai ;
Jarvis, Cody ;
Gu, Jing ;
Yan, Yong .
RENEWABLE & SUSTAINABLE ENERGY REVIEWS, 2015, 51 :986-997
[73]   Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals [J].
Yan, Long ;
Yao, Qian ;
Fu, Yao .
GREEN CHEMISTRY, 2017, 19 (23) :5527-5547
[74]   Controlled Polymerization of Next-Generation Renewable Monomers and Beyond [J].
Yao, Kejian ;
Tang, Chuanbing .
MACROMOLECULES, 2013, 46 (05) :1689-1712
[75]   Zirconium Oxide Supported Palladium Nanoparticles as a Highly Efficient Catalyst in the Hydrogenation-Amination of Levulinic Acid to Pyrrolidones [J].
Zhang, Jian ;
Xie, Bin ;
Wang, Liang ;
Yi, Xianfeng ;
Wang, Chengtao ;
Wang, Guoxiong ;
Dai, Zhifeng ;
Zheng, Anmin ;
Xiao, Feng-Shou .
CHEMCATCHEM, 2017, 9 (14) :2661-2667
[76]   Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives [J].
Zhang, Jun ;
Wu, ShuBin ;
Li, Bo ;
Zhang, HongDan .
CHEMCATCHEM, 2012, 4 (09) :1230-1237
[77]   Thermal Properties and Crystallization Behavior of Novel Biodegradable Poly(hexamethylene succinate-co-6 mol% butylene succinate) and Poly(hexamethylene succinate) [J].
Zhang, Kangjing ;
Yang, Huiying ;
Qiu, Zhaobin .
JOURNAL OF POLYMERS AND THE ENVIRONMENT, 2018, 26 (04) :1320-1327
[78]   Polymeric Ruthenium Porphyrin-Functionalized Carbon Nanotubes and Graphene for Levulinic Ester Transformations into γ-Valerolactone and Pyrrolidone Derivatives [J].
Zhang, Ting ;
Ge, Yao ;
Wang, Xuefeng ;
Chen, Jinzhu ;
Huang, Xueli ;
Liao, Yinnian .
ACS OMEGA, 2017, 2 (07) :3228-3240
[79]   Synthesis and Characterization of Biodegradable Crosslinked Polymers from 5-Hydroxylevulinic Acid and α,ω-Diols [J].
Zhang, Yan ;
Wu, Linbo ;
Li, Bo-Geng .
JOURNAL OF APPLIED POLYMER SCIENCE, 2010, 117 (06) :3315-3321
[80]   Recent developments and future prospects on bio-based polyesters derived from renewable resources: A review [J].
Zia, Khalid Mahmood ;
Noreen, Aqdas ;
Zuber, Mohammad ;
Tabasum, Shazia ;
Mujahid, Mohammad .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2016, 82 :1028-1040
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