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公开(公告)号：US10364319B2
公开(公告)日：2019-07-30
申请号：US15565572
申请日：2016-04-11
Inventor： Eugene Y. Chen , Miao Hong , Xiaoyan Tang
Abstract: The invention provides polymers of Formulas I-III, such as polyesters and unsaturated polyesters, and crosslinked and copolymerized polymers thereof. The invention also provides methods to catalytically ring-open five-membered rings such lactones, lactams, and thiolactones, as via ring-opening polymerization. The polymerization products are recyclable and can be depolymerized back to their monomer form via thermolysis and acid or base catalysis.
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公开(公告)号：US20210206912A1
公开(公告)日：2021-07-08
申请号：US17206400
申请日：2021-03-19
Inventor： Eugene Y. Chen , Xiaoyan Tang
Abstract: Biodegradable polymers with advantageous physical and chemical properties are described, as well as methods for making such polymers. In one embodiment, a new chemical synthesis route to technologically important biodegradable poly(3-hydroxybutyrate) (P3HB) with high isotacticity and molecular weight required for a practical use is described. The new route can utilize racemic eight-membered cyclic diolide (rac-DL), meso-DL, or a rac-DL and meso-DL mixture, derived from bio-sourced dimethyl succinate, and enantiomeric (R,R)-DL and (S,S)-DL, optically resolved by metal-based catalysts. With a stereoselective racemic molecular catalyst, the ROP of rac-DL under ambient conditions produces rapidly P3HB with essentially perfect isotacticity ([mm] >99%), high crystallinity and melting temperature (Tm=171° C.), as well as high molecular weight and low dispersity (Mn=1.54×105 g/mol, Ð=1.01).
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公开(公告)号：US10954335B2
公开(公告)日：2021-03-23
申请号：US16246302
申请日：2019-01-11
Inventor： Eugene Y. Chen , Xiaoyan Tang
IPC: C08G63/08 , C08L67/04 , C08G63/664 , C08G63/82 , B01J31/22
Abstract: Biodegradable polymers with advantageous physical and chemical properties are described, as well as methods for making such polymers. In one embodiment, a new chemical synthesis route to technologically important biodegradable poly(3-hydroxybutyrate) (P3HB) with high isotacticity and molecular weight required for a practical use is described. The new route can utilize racemic eight-membered cyclic diolide (rac-DL), meso-DL, or a rac-DL and meso-DL mixture, derived from bio-sourced dimethyl succinate, and enantiomeric (R,R)-DL and (S,S)-DL, optically resolved by metal-based catalysts. With a stereoselective racemic molecular catalyst, the ROP of rac-DL under ambient conditions produces rapidly P3HB with essentially perfect isotacticity ([mm]>99%), high crystallinity and melting temperature (Tm=171° C.), as well as high molecular weight and low dispersity (Mn=1.54×105 g/mol, Ð=1.01).
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公开(公告)号：US09828354B2
公开(公告)日：2017-11-28
申请号：US15272324
申请日：2016-09-21
Inventor： Eugene Y. Chen , Dajiang Liu
IPC: C07D307/46 , C07D407/06 , C07D307/12 , C10L1/02 , C10L1/185
CPC classification number: C07D307/46 , C07D307/12 , C07D407/06 , C10L1/026 , C10L1/1855 , Y02E50/13 , Y02P30/20
Abstract: The invention provides new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5′-di(hydroxymethyl) furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, the invention now provides methods to convert such nonfood biomass directly into DHMF by a simple process as described herein. The invention also provides highly effective new methods for upgrading other biomass furaldehydes and related compound to liquid fuels. The methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C8-C12)furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.
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公开(公告)号：US09469626B2
公开(公告)日：2016-10-18
申请号：US13934074
申请日：2013-07-02
Inventor： Eugene Y. Chen , Dajiang Liu
IPC: C07D307/00 , C07D407/06 , C07D307/12 , C10L1/02 , C07D307/46
CPC classification number: C07D307/46 , C07D307/12 , C07D407/06 , C10L1/026 , C10L1/1855 , Y02E50/13 , Y02P30/20
Abstract: The invention provides new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5′-di(hydroxymethyl)furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, the invention now provides methods to convert such nonfood biomass directly into DHMF by a simple process as described herein. The invention also provides highly effective new methods for upgrading other biomass furaldehydes and related compound to liquid fuels. The methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C8-C12)furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.
Abstract translation: 本发明通过有机催化提供了5-羟甲基糠醛（HMF）的直接umpolung自缩合的新方法，从而将容易获得的底物升级成5,5'-二（羟甲基）呋喃蛋白（DHMF）。 虽然已经开发了许多有效的催化剂体系用于将植物生物质资源转化为HMF，但是本发明现在提供了通过本文所述的简单方法将这种非食用生物质直接转化成DHMF的方法。 本发明还提供了用于将其它生物物质的醛和相关化合物升级为液体燃料的高效的新方法。 方法包括将生物质糠醛的有机催化自缩合（umpolung）转化为（C8-C12）糠醛中间体，然后氢化，醚化或酯化成氧化生物柴油，或通过金属酸串联催化加氢脱氧成优质烃燃料。
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Patent Agency Ranking
公开(公告)号：US10174161B2
公开(公告)日：2019-01-08
申请号：US15756670
申请日：2016-09-02
Inventor： Eugene Y. Chen , Jian-Bo Zhu
IPC: C08G63/82 , C08G63/08 , C07D405/04 , C07D515/08 , C08L67/04
Abstract: B/N Lewis pairs have been discovered to catalyze rapid epimerization of meso-lactide (LA) or LA diastereomers quantitatively into rac-LA. The obtained rac-LA can be kinetically polymerized into poly(L-lactide) and optically resolved D-LA, with a high stereoselectivity factor kL/kD of 53 and an ee value of 91% at 50.6% monomer conversion, by a bifunctional chiral catalyst. The epimerization and enantioselective polymerization can be coupled into a one-pot process for transforming meso-LA directly into poly(L-lactide) and D-LA.
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公开(公告)号：US09309332B2
公开(公告)日：2016-04-12
申请号：US14010235
申请日：2013-08-26
Inventor： Eugene Y. Chen , Yangjian Hu , Yuetao Zhang
IPC: C08F4/44 , C08F4/78 , C08F4/76 , C08F24/00 , C08F124/00 , C08F4/6592
CPC classification number: C08F4/44 , C08F4/65927 , C08F4/76 , C08F24/00 , C08F124/00
Abstract: The invention provides novel polymer compositions and methods for preparing such compositions. The invention also provides methods for polymerizing various unsaturated monomers, including naturally occurring or plant biomass-derived renewable acrylic monomers. The monomers can be rapidly polymerized using various organic catalysts or organometallic catalysts, as described herein. In one embodiment, nearly perfectly isotactic polymers (mmmm>99%) can be prepared using a C2-symmetric zirconocenium catalyst.
Abstract translation: 本发明提供新的聚合物组合物和制备这种组合物的方法。 本发明还提供了聚合各种不饱和单体的方法，包括天然存在的或植物生物质衍生的可再生丙烯酸单体。 如本文所述，可以使用各种有机催化剂或有机金属催化剂快速聚合单体。 在一个实施方案中，可以使用C2对称锆锡催化剂制备几乎完全的全同立构聚合物（mmmm> 99％）。
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公开(公告)号：US11629223B2
公开(公告)日：2023-04-18
申请号：US17206400
申请日：2021-03-19
Inventor： Eugene Y. Chen , Xiaoyan Tang
IPC: C08G63/08 , C08L67/04 , C08G63/82 , B01J31/22 , C08G63/664
Abstract: Biodegradable polymers with advantageous physical and chemical properties are described, as well as methods for making such polymers. In one embodiment, a new chemical synthesis route to technologically important biodegradable poly(3-hydroxybutyrate) (P3HB) with high isotacticity and molecular weight required for a practical use is described. The new route can utilize racemic eight-membered cyclic diolide (rac-DL), meso-DL, or a rac-DL and meso-DL mixture, derived from bio-sourced dimethyl succinate, and enantiomeric (R,R)-DL and (S,S)-DL, optically resolved by metal-based catalysts. With a stereoselective racemic molecular catalyst, the ROP of rac-DL under ambient conditions produces rapidly P3HB with essentially perfect isotacticity ([mm]>99%), high crystallinity and melting temperature (Tm=171° C.), as well as high molecular weight and low dispersity (Mn=1.54×105 g/mol, Ð=1.01).
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公开(公告)号：US20230037920A1
公开(公告)日：2023-02-09
申请号：US17781501
申请日：2020-12-02
Inventor： Eugene Y. Chen , Changxia Shi
IPC: C08G75/26 , C07D333/78
Abstract: A monomer design strategy based on a bridged bicyclic thiolactone that produces stereo-disordered to perfectly stereo-ordered polythioesters is disclosed. The described polythioesters exhibit high crystallinity and full chemical recyclability. Such polymers possess intrinsic tacticity-independent crystallinity and chemical recyclability, tunable tacticities from stereo-disorder to perfect stereoregularity, as well as combined high-performance properties such as high thermal stability and crystallinity, and high mechanical strength, ductility and toughness.
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公开(公告)号：US10759899B2
公开(公告)日：2020-09-01
申请号：US16053225
申请日：2018-08-02
Inventor： Eugene Y. Chen , Jian-Bo Zhu
Abstract: The invention discloses a class of new polymers, trans-ring-fused poly(4-hydroxybutyrate)s (RF-P4HB) that exhibit a unique set of properties, including robust thermal stability and mechanical strength, quantitative recyclability to the building block monomers via thermolysis and/or chemical catalysis, and convenient production from the chemical ring-opening polymerization under ambient temperature and pressure. Another unique property is the formation of crystalline stereocomplexed polymers with high melting temperature upon mixing the two enantiomeric RF-P4HB chains via stereocomplexing co-crystallization. This invention also provides the corresponding ring-fused lactone monomer structures that enable the synthesis of the RF-P4HB polymers, through trans-fusing of rings to the parent γ-butyrolactone ring. Furthermore, a polymerization or copolymerization process for the synthesis of RF-P4HB polymers and copolymers is disclosed.
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