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1. 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。

2. 发明授权

US06191321B1 Process for preparing 1,3-propanediol from methyl 3-hydroxypropionate 失效
标题翻译：由3-羟基丙酸甲酯制备1,3-丙二醇的方法
公开(公告)号：US06191321B1
公开(公告)日：2001-02-20
申请号：US09163534
申请日：1998-09-30
申请人： Thomas Clayton Forschner , Paul Richard Weider , Lynn Henry Slaugh , Joseph Broun Powell
发明人： Thomas Clayton Forschner , Paul Richard Weider , Lynn Henry Slaugh , Joseph Broun Powell
IPC分类号： C07G2704
CPC分类号： C07C29/149 , C07C67/37 , C12C11/02 , C07C31/205 , C07C69/675
摘要： 1,3-Propanediol is prepared in good yield by hydrogenation of methyl 3-hydroxypropionate in the presence of a copper zinc oxide hydrogenation catalyst. The use of the copper zinc oxide hydrogenation catalyst enables greater productivity in an overall process for preparing 1,3-propanediol from ethylene oxide via methyl 3-hydroxypropionate intermediate.
摘要翻译：在铜锌氧化物氢化催化剂的存在下，3-羟基丙酸甲酯的氢化制备了1,3-丙二醇。使用铜氧化锌氢化催化剂可在通过3-羟基丙酸甲酯中间体从环氧乙烷制备1,3-丙二醇的整个方法中提高生产率。

3. 发明授权

US07538061B2 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 - 铁催化剂一步生产1,3-丙二醇
公开(公告)号：US07538061B2
公开(公告)日：2009-05-26
申请号：US10790598
申请日：2004-03-01
申请人： John Frederick Knifton , Talmadge Gail James , Lynn Henry Slaugh , Paul Richard Weider , Kevin Dale Allen , Joseph Broun Powell
发明人： John Frederick Knifton , Talmadge Gail James , Lynn Henry Slaugh , Paul Richard Weider , Kevin Dale Allen , Joseph Broun Powell
IPC分类号： B01J31/12 , B01J31/20 , B01J31/22 , B01J31/24 , B01J31/18
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。

4. 发明授权

US06576802B2 One-step production of 1, 3-propanediol from ethylene oxide and syngas with a catalyst with a phospholanoalkane ligand 失效
公开(公告)号：US06576802B2
公开(公告)日：2003-06-10
申请号：US10158452
申请日：2002-05-30
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： C07C2700
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.

5. 发明授权

US06469222B2 One step process for preparing A 1,3-diol 失效
标题翻译：制备1,3-二醇的一步法
公开(公告)号：US06469222B2
公开(公告)日：2002-10-22
申请号：US09808974
申请日：2001-03-15
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： C07C2700
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。

6. 发明授权

US5841003A Process for preparing alkanediols 失效
标题翻译：制备烷二醇的方法
公开(公告)号：US5841003A
公开(公告)日：1998-11-24
申请号：US685173
申请日：1996-07-23
申请人： Lynn Henry Slaugh , Paul Richard Weider , Joseph Broun Powell
发明人： Lynn Henry Slaugh , Paul Richard Weider , Joseph Broun Powell
IPC分类号： C07C29/141 , C07C45/58 , C07C27/00
CPC分类号： C07C29/141 , C07C45/58
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 lipophilic ruthenium 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：在非磷化氢连接的钴催化剂和亲脂性钌的存在下，在一种基本上不与水混合的溶剂中使烯化氧与一氧化碳和氢气反应的方法制备1,3-丙二醇。促进剂以产生含有小于15重量％的量的羟基卡那定的中间产物混合物; 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。

7. 发明授权

US07115540B2 Synthesis of aliphatic 1,3-diols utilizing reduced ligand concentration and water extraction 失效
公开(公告)号：US07115540B2
公开(公告)日：2006-10-03
申请号：US10669485
申请日：2003-09-24
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： B01J31/20 , B01J31/28 , B01J31/16
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.

8. 发明授权

US06903044B2 One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a N-heterocyclic 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N-杂环配体
公开(公告)号：US06903044B2
公开(公告)日：2005-06-07
申请号：US10298866
申请日：2002-11-18
申请人： John Frederick Knifton , Talmadge Gail James , Kevin Dale Allen , Paul Richard Weider , Joseph Broun Powell , Lynn Henry Slaugh , Timothy Williams
发明人： John Frederick Knifton , Talmadge Gail James , Kevin Dale Allen , Paul Richard Weider , Joseph Broun Powell , Lynn Henry Slaugh , Timothy Williams
IPC分类号： B01J31/28 , B01J31/18 , B01J31/20 , C07B61/00 , C07C29/16 , C07C29/44 , C07C31/20 , B01J31/00
CPC分类号： C07C29/16 , B01J31/181 , B01J31/1815 , B01J31/183 , B01J31/20 , B01J31/28 , B01J2231/48 , B01J2531/0208 , B01J2531/025 , B01J2531/821 , B01J2531/845 , Y02P20/52 , C07C31/205
摘要： Disclosed is a new catalyst composition comprising a bimetallic Co—Ru catalyst complexed with a N-heterocylcic ligand that is effective, economical, and provides improvements in oxidative stability in the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, cobalt-ruthenium-2,2′-bipyrimidine, 2,2′-dipyridyl, or 2,4,6-tripridyl-s-triazine catalyst precursors in cyclic ether solvents, such as 1,3-dioxolane, 1,4-dioxolane, 1,4-dioxane, and 2-ethyl-2-methyl-1,3-dioxolane, provide good yields of 1,3-PDO in a one step synthesis.
摘要翻译：公开了一种新的催化剂组合物，其包含与N-杂环配体络合的双金属Co-Ru催化剂，该双金属Co-Ru催化剂有效，经济，并且在一步合成1,3-丙二醇（1,3-PDO）中提供氧化稳定性的改善，来自环氧乙烷和合成气。例如，在环醚溶剂中的钴 - 钌-2,2'-联嘧啶，2,2'-二吡啶基或2,4,6-三苯基-s-三嗪催化剂前体，如1,3-二氧戊环， 4-二氧戊环，1,4-二恶烷和2-乙基-2-甲基-1,3-二氧戊环，在一步合成中可提供1,3-PDO的良好产率。

9. 发明授权

US06180838B2 Process for preparing alkanediols 失效
标题翻译：制备烷二醇的方法
公开(公告)号：US06180838B2
公开(公告)日：2001-01-30
申请号：US08618734
申请日：1996-03-20
申请人： Lynn Henry Slaugh , Paul Richard Weider , Joseph Broun Powell
发明人： Lynn Henry Slaugh , Paul Richard Weider , Joseph Broun Powell
IPC分类号： C07C2704
CPC分类号： B01J31/04 , B01J31/0268 , B01J31/20 , B01J31/2234 , B01J31/26 , B01J31/4046 , B01J2231/48 , B01J2531/822 , C07C29/141 , C07C29/16 , C07C45/58 , C07C45/80 , Y02P20/584 , C07C47/19 , C07C31/205 , C07C31/207
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 rhodium catalyst and a catalyst 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° C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing rhodium 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 rhodium catalyst.
摘要翻译：在包含非磷化氢连接的铑催化剂和催化剂促进剂的存在下，使烯化氧与一氧化碳和氢气在基本上不与水混合的溶剂中进行反应的方法制备了1,3-二醇，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含水液体，并将含有羟基卡那酸的水相与含铑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铑催化剂。

10. 发明授权

US5981808A Cobalt-catalyzed process for preparing 1, 3-propanediol from etylene oxide 失效
标题翻译：用于由乙烯氧化物制备1,3-丙二醇的钴催化方法
公开(公告)号：US5981808A
公开(公告)日：1999-11-09
申请号：US892831
申请日：1997-07-15
申请人： Joseph Broun Powell , Lynn Henry Slaugh , David Cleve Eubanks , Stephan Blake Mullin , Terry Blain Thomason , Paul Richard Weider , Thomas Carl Semple
发明人： Joseph Broun Powell , Lynn Henry Slaugh , David Cleve Eubanks , Stephan Blake Mullin , Terry Blain Thomason , Paul Richard Weider , Thomas Carl Semple
IPC分类号： C07C29/141 , C07C45/58 , C07C27/00
CPC分类号： C07C29/141 , C07C45/58
摘要： 1,3-Propanediol is prepared in a process which involves reacting ethylene 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 catalyst promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt %; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxypropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol.The process enables the production of 1,3-propanediol in high yield and selectivity without the use of a phosphine ligand-modified cobalt catalyst.
摘要翻译：在一种方法中制备1,3-丙二醇，该方法包括在非磷化氢连接的钴催化剂和催化剂促进剂的存在下，将环氧乙烷与一氧化碳和氢气在基本上不与水相混溶的溶剂中反应以产生中间产物含有小于15重量％的3-羟基丙醛的混合物; 在低于约100℃的温度下将中间产物混合物中的3-羟基丙醛萃取到含水液体中，并从含钴催化剂的有机相中分离出含有3-羟基丙醛的水相; 将水相中的3-羟基丙醛氢化为1,3-丙二醇; 并回收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，而不需要使用膦配位体改性的钴催化剂。

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