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31. 发明授权

US5786524A Process for preparation of 1,3-propanediol via hydrogenation of 3-hydroxypropanal 失效
标题翻译： 3-羟基丙醛氢化制备1,3-丙二醇的方法
公开(公告)号：US5786524A
公开(公告)日：1998-07-28
申请号：US655639
申请日：1996-05-30
申请人： Joseph Broun Powell , William Ridley Pledger , Andreas Nikolaos Matzakos , Paul Richard Weider , Juan Pedro Arhancet
发明人： Joseph Broun Powell , William Ridley Pledger , Andreas Nikolaos Matzakos , Paul Richard Weider , Juan Pedro Arhancet
IPC分类号： C07C29/141 , C07C45/58 , C07C31/18 , C07C27/04
CPC分类号： C07C29/141 , C07C45/58
摘要： 1,3-propanediol is prepared from 3-hydroxypropanal in a process comprising the steps of: (a) contacting, at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt or rhodium catalyst and an effective amount of a catalyst promoter under reaction conditions effective to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal; (b) adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid a major portion of the 3-hydroxypropanal at a temperature less than about 100.degree. C. so as to provide an aqueous phase comprising 3-hydroxypropanal in a concentration of at least about 20 wt %, and an organic phase comprising at least a portion of the cobalt or rhodium catalyst or a cobalt- or rhodium-containing derivative thereof; (c) separating the aqueous phase from the organic phase; (d) diluting the aqueous phase comprising 3-hydroxy-propanal with an aqueous liquid to form a 3-hydroxypropanal solution having a 3-hydroxypropanal concentration within the range of about 0.2 to about 15 weight percent; (e) passing said aqueous 3-hydroxypropanal solution to a hydrogenation zone and in contact with a fixed-bed hydrogenation catalyst under hydrogenation conditions for a time effective to form an aqueous solution comprising 1,3-propanediol; and (f) recovering said 1,3-propanediol.
摘要翻译： 1,3-丙二醇由3-羟基丙醛制备，其方法包括以下步骤：（a）在约50℃至约100℃的温度和约500至约100℃的压力范围内接触，在有效量的非磷化氢连接的钴或铑催化剂和有效量的催化剂助催化剂的存在下，在反应条件下有效量的催化剂助催化剂，在大约5000psig的环氧乙烷与一氧化碳和氢气基本上是非水混溶性溶剂中以产生包含小于15重量％的3-羟基丙醛的中间产物混合物; （b）向所述中间产物混合物中加入水性液体，并在低于约100℃的温度下将大部分3-羟基丙醛提取到所述含水液体中，以提供浓度为3-羟基丙醛的水相至少约20重量％，以及包含至少一部分钴或铑催化剂或其含钴或铑的衍生物的有机相; （c）将水相与有机相分离; （d）用水性液体稀释含有3-羟基 - 丙醛的水相，形成3-羟基丙醛浓度在约0.2-约15重量％范围内的3-羟基丙醛溶液; （e）在氢化条件下将所述3-羟基丙醛水溶液通入氢化区并与固定床氢化催化剂接触，有效形成包含1,3-丙二醇的水溶液; 和（f）回收所述1,3-丙二醇。

32. 发明授权

US5777182A Cobalt-catalyzed process for preparing 1,3-propanidiol 失效
标题翻译：用于制备1,3-丙二醇的钴催化方法
公开(公告)号：US5777182A
公开(公告)日：1998-07-07
申请号：US703295
申请日：1996-08-26
申请人： Joseph Broun Powell , Lynn Henry Slaugh , Thomas Clayton Forschner , Jiang-Jen Lin , Terry Blane Thomason , Paul Richard Weider , Thomas Carl Semple , Juan Pedro Arhancet , Howard Lam-Ho Fong , Stephen Blake Mullin , Kevin Dale Allen , David Cleve Eubanks , David William Johnson
发明人： Joseph Broun Powell , Lynn Henry Slaugh , Thomas Clayton Forschner , Jiang-Jen Lin , Terry Blane Thomason , Paul Richard Weider , Thomas Carl Semple , Juan Pedro Arhancet , Howard Lam-Ho Fong , Stephen Blake Mullin , Kevin Dale Allen , David Cleve Eubanks , David William Johnson
IPC分类号： C07C29/141 , C07C45/58 , C07C45/80 , C07C27/04
CPC分类号： C07C45/58 , C07C29/141 , C07C45/80
摘要： 1,3-propanediol is prepared in a process which involves hydroformylating ethylene oxide: (a) in an essentially non-water-miscible solvent in the presence of a non-ligated cobalt catalyst and a catalyst promoter at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal; (b) adding an aqueous liquid and extracting at a temperature less than about 100.degree. C. the 3-hydroxypropanal to provide an aqueous phase comprising 3-hydroxypropanal in greater concentration than the concentration of 3-hydroxypropanal in said intermediate product mixture, and an organic phase comprising the cobalt catalyst; (c) separating the aqueous phase from the organic phase; (d) hydrogenating the 3-hydroxypropanal to provide a hydrogenation product mixture comprising 1,3-propanediol; and (e) recovering 1,3-propanediol from said hydrogenation product mixture. The process enables the production of 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.
摘要翻译： 1,3-丙二醇的制备方法包括在环氧乙烷中加氢甲酰化：（a）在非连接的钴催化剂和催化剂助催化剂存在下，在基本上与水不混溶的溶剂中，温度范围为约 50℃至约100℃，压力范围为约500至约5000psig，以产生包含小于约15重量％的3-羟基丙醛的中间产物混合物; （b）加入水性液体并在低于约100℃的温度下提取3-羟基丙醛，以提供比所述中间产物混合物中3-羟基丙醛浓度更高浓度的3-羟基丙醛的水相，以及包含钴催化剂的有机相; （c）将水相与有机相分离; （d）氢化3-羟基丙醛以提供包含1,3-丙二醇的氢化产物混合物; 和（e）从所述氢化产物混合物中回收1,3-丙二醇。该方法能够以高产率和选择性生产1,3-丙二醇，而不需要使用膦配体改性的钴催化剂。

33. 发明授权

US5689016A Cobalt-catalyzed process for preparing alkanediols using a rhodium promoter 失效
标题翻译：使用铑促进剂制备烷二醇的钴催化方法
公开(公告)号：US5689016A
公开(公告)日：1997-11-18
申请号：US618711
申请日：1996-03-20
申请人： Paul Richard Weider , Lynn Henry Slaugh , Joseph Broun Powell
发明人： Paul Richard Weider , Lynn Henry Slaugh , Joseph Broun Powell
IPC分类号： B01J31/20 , C07C29/141 , C07C29/16 , C07C45/58 , C07C45/80 , C07C27/04
CPC分类号： B01J31/0268 , B01J31/04 , B01J31/20 , B01J31/2234 , B01J31/26 , B01J31/4046 , C07C29/141 , C07C45/58 , C07C45/80 , B01J2231/48 , B01J2531/822 , Y02P20/584
摘要： An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a rhodium promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol. The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.
摘要翻译：在包括非磷化氢连接的钴催化剂和铑助催化剂存在下，使烯化氧与一氧化碳和氢气在基本上不与水相混溶的溶剂中进行反应的方法来制备链烷二醇，如1,3-丙二醇以产生含有小于15重量％的量的羟基卡那尔的中间产物混合物; 在低于约100℃的温度下将羟基卡那酸从中间产物混合物中提取成水性液体，并将含有羟基卡那的水相与含钴催化剂的有机相分离; 将水相中的羟基卡那酸氢化成链烷二醇; 并回收链烷二醇。该方法能够以高产率和选择性生产链烷二醇如1,3-丙二醇，而不需要使用膦配体改性的钴催化剂。

34. 发明授权

US09217113B2 Co-production of biofuels and glycols 有权
标题翻译：联合生产生物燃料和二醇
公开(公告)号：US09217113B2
公开(公告)日：2015-12-22
申请号：US13495654
申请日：2012-06-13
申请人： Joseph Broun Powell
发明人： Joseph Broun Powell
IPC分类号： C07C29/132 , C10G3/00 , C07C51/377 , C10L1/04 , C07C29/00 , C07C29/60
CPC分类号： C10G3/00 , C07C29/00 , C07C29/132 , C07C29/60 , C10G3/42 , C10G2300/1011 , C10G2300/4081 , C10G2300/42 , C10L1/04 , C10L1/06 , C10L2200/0469 , C10L2270/023 , Y02P30/20 , C07C31/205 , C07C31/202
摘要： Methods and systems for co-producing higher hydrocarbons and glycols from bio-based feedstocks containing carbohydrates are disclosed.
摘要翻译：公开了从含有碳水化合物的生物基原料共同生产高级烃和二醇的方法和系统。

35. 发明授权

US08729325B2 Biomass conversion systems having a fluid circulation loop containing a centripetal force-based separation mechanism for control of cellulosic fines and methods for use thereof 有权
标题翻译：具有包含用于控制纤维素细粒的向心力分离机构的流体循环回路的生物质转化系统及其使用方法
公开(公告)号：US08729325B2
公开(公告)日：2014-05-20
申请号：US13332318
申请日：2011-12-20
申请人： Joseph Broun Powell
发明人： Joseph Broun Powell
IPC分类号： C07C1/00
CPC分类号： B01J19/0046 , C10G1/002 , C10G1/065 , C10G3/00 , C10G3/42 , C10G2300/1014 , C10L1/02 , Y02P30/20
摘要： Digestion of cellulosic biomass to produce a hydrolysate may be accompanied by the formation of cellulosic fines which may be damaging to system components. Biomass conversion systems that may address the issue of cellulosic fines may comprise a fluid circulation loop comprising: a hydrothermal digestion unit; a solids separation unit that is in fluid communication with an outlet of the hydrothermal digestion unit; where the solids separation unit comprises a centripetal force-based separation mechanism that comprises a fluid outlet and a solids outlet; and a catalytic reduction reactor unit that is in fluid communication with the fluid outlet of the centripetal force-based separation mechanism and an inlet of the hydrothermal digestion unit.
摘要翻译：消化纤维素生物质以产生水解产物可伴随着可能损害系统组分的纤维素细粉的形成。可能解决纤维素细粒问题的生物质转化系统可以包括流体循环回路，包括：水热消解单元; 固体分离单元，其与所述水热消解单元的出口流体连通; 其中固体分离单元包括向心力分离机构，其包括流体出口和固体出口; 以及催化还原反应器单元，其与向心力分离机构的流体出口和水热消解单元的入口流体连通。

36. 发明授权

US08013192B2 Process for preparing 1,3-propanediol 失效
标题翻译： 1,3-丙二醇制备方法
公开(公告)号：US08013192B2
公开(公告)日：2011-09-06
申请号：US11950294
申请日：2007-12-04
申请人： Douglas Lee Husen , Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
发明人： Douglas Lee Husen , Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
IPC分类号： C07C27/20 , C07C27/04 , C07C29/36
CPC分类号： C07C29/141 , C07C29/80 , C07C45/58 , C07C45/64 , C07C45/80 , C07C47/19 , C07C31/205
摘要： The invention provides a process for preparing 1,3-alkanediols, such as 1,3-propanediol (PDO), from 3-hydroxyaldehydes, such as 3-hydroxypropanal (HPA), comprising providing a mixture of 3-hydroxyaldehydes in an organic solvent; extracting into an aqueous liquid a major portion of the 3-hydroxyaldehydes to provide an aqueous phase comprising 3-hydroxyaldehydes in greater concentration than the concentration of 3-hydroxyaldehydes in the 3-hydroxyaldehyde mixture, and an organic phase; separating the aqueous phase from the organic phase; contacting the aqueous phase with hydrogen in the presence of a hydrogenation catalyst to provide a hydrogenation product mixture comprising 1,3-alkanediols and water; separating water from the 1,3-alkanediols using a multi-effect evaporation scheme; recycling water containing about 50 wt % or less 1,3-propanediol based upon the total amount of 1,3-propanediol and water to the extraction stage; and recovering 1,3-alkanediols.
摘要翻译：本发明提供了从3-羟基醛如3-羟基丙醛（HPA）制备1,3-烷二醇如1,3-丙二醇（PDO）的方法，其包括在有机溶剂中提供3-羟基醛的混合物 ; 将大部分3-羟基醛萃取到含水液体中以提供包含3-羟基醛的水相，其浓度高于3-羟基醛混合物中3-羟基醛的浓度和有机相; 将水相与有机相分离; 在氢化催化剂存在下使水相与氢气接触，以提供包含1,3-烷二醇和水的氢化产物混合物; 使用多效蒸发方案从1,3-烷二醇分离水; 基于1,3-丙二醇和水的总量将含有约50重量％或更少的1,3-丙二醇的水循环到萃取阶段; 并回收1,3-链烷二醇。

37. 发明授权

US06753289B2 One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a phospholanoalkane ligand 失效
标题翻译：从环氧乙烷和合成气一步生产1,3-丙二醇与催化剂与磷酰烷配体
公开(公告)号：US06753289B2
公开(公告)日：2004-06-22
申请号：US10371462
申请日：2003-02-21
申请人： John Frederick Knifton , Talmadge Gail James , Kevin Dale Allen , Paul Richard Weider , Joseph Broun Powell , Lynn Henry Slaugh
发明人： John Frederick Knifton , Talmadge Gail James , Kevin Dale Allen , Paul Richard Weider , Joseph Broun Powell , Lynn Henry Slaugh
IPC分类号： B01J3100
CPC分类号： B01J31/2433 , B01J31/20 , B01J31/2208 , B01J2231/48 , B01J2531/0211 , B01J2531/0258 , B01J2531/821 , B01J2531/845
摘要： Disclosed is a novel class of modified ruthenium catalysts useful in the one step synthesis of 1,3-PDO comprising (a) a cobalt component comprising one or more non-ligated cobalt compounds; and (b) a ruthenium component comprising in major part a ruthenium carbonyl compound ligated with a phospholanoalkane ligand, solubilized in an ether solvent, that provides potential improvements in cost and performance in one step hydroformylation/hydrogenation. For example, cobalt-ruthenium-bidentate, bis(phospholano)alkane catalyst precursors in ether solvents provide good yields of 1,3-PDO in a one step synthesis.
摘要翻译：公开了一种新型的改性钌催化剂，其用于一步合成1,3-PDO，其包含（a）包含一种或多种非连接的钴化合物的钴组分; 和（b）主要部分包含与溶于醚溶剂中的磷酸烷烃配体连接的钌羰基化合物的钌组分，其在一步加氢甲酰化/氢化中提供成本和性能的潜在改进。例如，在醚溶剂中的钴 - 钌二齿，双（磷酸）烷烃催化剂前体在一步合成中提供了1,3-PDO的良好产率。

38. 发明授权

US06750373B2 One-step production of 1, 3-propanediol from ethylene oxide and syngas with a cobalt-iron catalyst 失效
标题翻译：一氧化碳和合成气用钴 - 铁催化剂一步法制备1,3-丙二醇
公开(公告)号：US06750373B2
公开(公告)日：2004-06-15
申请号：US10146675
申请日：2002-05-15
申请人： John Frederick Knifton , Talmadge Gail James , Lynn Henry Slaugh , Kevin Dale Allen , Paul Richard Weider , Joseph Broun Powell
发明人： John Frederick Knifton , Talmadge Gail James , Lynn Henry Slaugh , Kevin Dale Allen , Paul Richard Weider , Joseph Broun Powell
IPC分类号： C07C2700
CPC分类号： B01J31/24 , B01J31/1805 , B01J31/1815 , B01J31/183 , B01J31/20 , B01J31/28 , B01J2231/321 , B01J2231/48 , B01J2531/0241 , B01J2531/842 , B01J2531/845 , C07C29/16 , Y02P20/52 , C07C31/205
摘要： Disclosed is a new catalyst composition comprising a bimetallic Co—Fe catalyst, optionally complexed with a ligand selected from a N-heterocycle, phosphine, or porphorine ligand, that provides a lower cost alternative for the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, a catalyst containing cobalt carbonyl: iron carbonyl with no ligand, or a catalyst containing a cobalt carbonyl: octaethylporphine iron acetate provide moderate yields of 1,3-PDO in a one step synthesis under mild conditions.
摘要翻译：公开了一种新的催化剂组合物，其包含任选与选自N-杂环，膦或卟吩配体的配体络合的双金属Co-Fe催化剂，其为1,3-丙二醇的一步合成提供了较低成本的替代方案（ 1,3-PDO）和环氧乙烷和合成气。例如，在温和条件下，在一步合成中含有羰基羰基羰基，不含配体的羰基催化剂或含有羰基钴：八乙基卟吩乙酸铁的乙酸铁的催化剂提供了适量的1,3-PDO产率。

39. 发明授权

US06706656B2 One step process for preparing a 1,3-diol 失效
标题翻译：一步法制备1,3-二醇
公开(公告)号：US06706656B2
公开(公告)日：2004-03-16
申请号：US10127957
申请日：2002-04-23
申请人： John Frederick Knifton , Lynn Henry Slaugh , Paul Richard Weider , Talmadge Gail James , Joseph Broun Powell , Kevin Dale Allen , Timothy Scott Williams
发明人： John Frederick Knifton , Lynn Henry Slaugh , Paul Richard Weider , Talmadge Gail James , Joseph Broun Powell , Kevin Dale Allen , Timothy Scott Williams
IPC分类号： B01J3100
CPC分类号： B01J31/2409 , B01J31/20 , B01J31/24 , B01J31/2414 , B01J31/248 , B01J2231/48 , B01J2531/821 , B01J2531/845 , C07C29/16 , Y02P20/52 , Y02P20/584 , C07C31/205
摘要： The invention provides a process for an improved oxirane hydroformylation catalyst, the improved oxirane hydroformylation catalyst, and a one step process for preparing a 1,3-diol in the presence of such a catalyst. One process for preparing the hydroformylation catalyst involves: a) forming a complex (A) by contacting a ruthenium(0) compound with a ditertiary phosphine ligand; and b) forming a complex (B) by subjecting complex (A) to a redox reaction with a cobalt(0) carbonyl compound. This catalyst is used in a one step hydroformylation process for preparing a 1,3-diol, comprising the reaction of an oxirane with syngas at hydroformylation conditions in an inert solvent in the presence of the above hydroformylation catalyst where recovery of product is preferably accomplished via phase separation of a diol rich phase from the bulk reaction liquor.
摘要翻译：本发明提供改进的环氧乙烷加氢甲酰化催化剂，改进的环氧乙烷加氢甲酰化催化剂的方法，以及在这种催化剂存在下制备1,3-二醇的一步法。制备加氢甲酰化催化剂的一个方法包括：a）通过使钌（O）化合物与二膦配体接触形成络合物（A）; 和b）通过使复合物（A）与羰基钴（O）化合物进行氧化还原反应形成络合物（B）。该催化剂用于制备1,3-二醇的一步加氢甲酰化方法，其包括在上述加氢甲酰化催化剂存在下，在惰性溶剂中，在加氢甲酰化条件下使环氧乙烷与合成气反应，其中产物的回收优选通过富二醇相与本体反应液相分离。

40. 发明授权

US06660892B2 Synthesis of aliphatic 1,3-diols utilizing reduced ligand concentration and water extraction 失效
标题翻译：利用配体浓度降低和水提取合成脂肪族1,3-二醇
公开(公告)号：US06660892B2
公开(公告)日：2003-12-09
申请号：US10360302
申请日：2003-02-07
申请人： Joseph Broun Powell , Paul Richard Weider , John Frederick Knifton , Kevin Dale Allen , Lynn Henry Slaugh , Juan Pedro Arhancet
发明人： Joseph Broun Powell , Paul Richard Weider , John Frederick Knifton , Kevin Dale Allen , Lynn Henry Slaugh , Juan Pedro Arhancet
IPC分类号： C07C2700
CPC分类号： B01J31/2471 , B01J31/1805 , B01J31/1815 , B01J31/183 , B01J31/20 , B01J31/24 , B01J31/28 , B01J2231/321 , B01J2531/025 , B01J2531/16 , B01J2531/80 , B01J2531/82 , B01J2531/821 , B01J2531/824 , B01J2531/828 , B01J2531/845 , C07C29/16 , Y02P20/584 , C07C31/205
摘要： This invention is a process for synthesizing aliphatic 1,3-diols in one step by hydroformylation and hydrogenation of oxirane, carbon monoxide, and hydrogen employing a catalyst comprising a cobalt carbonyl compound and a cocatalyst metal compound ligated with a ligand in a ligand to cocatalyst metal atom molar ratio in the range of 0.2:1.0 to 0.6:1.0, optionally in the presence of a promoter, where recovery of product is preferably accomplished via water extraction of a diol rich phase from the bulk reaction mixture. The process modifications can, particularly in combination, be beneficial with respect to product recovery, catalyst recycle, and overall economics of a one-step process for producing aliphatic 1,3-diols.
摘要翻译：本发明是通过使用包含羰基钴化合物的催化剂和与配位体中的配体连接的助催化剂金属化合物进行助催化剂的环氧乙烷，一氧化碳和氢气的加氢甲酰化和氢化来合成脂肪族1,3-二醇的方法金属原子摩尔比在0.2:1.0至0.6:1.0的范围内，任选地在助催化剂存在下，其中产物的回收优选通过从本体反应混合物中萃取富含二醇的相来完成。关于产物回收，催化剂再循环以及用于生产脂族1,3-二醇的一步法的总体经济性，方法修饰尤其可以组合地是有益的。

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