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公开(公告)号：US5463144A
公开(公告)日：1995-10-31
申请号：US316671
申请日：1994-09-30
申请人： Joseph B. Powell , Lynn H. Slaugh , Thomas C. Forschner , Terry B. Thomason , Thomas C. Semple , Paul R. Weider , Juan P. Arhancet
发明人： Joseph B. Powell , Lynn H. Slaugh , Thomas C. Forschner , Terry B. Thomason , Thomas C. Semple , Paul R. Weider , Juan P. Arhancet
CPC分类号： C07C45/58 , C07C29/141 , C07C29/16 , C07C45/80
摘要： 1,3-propanediol is prepared in a process comprising the steps of:contacting 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 catalyst and an effective amount of a lipophilic quaternary ammonium salt 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, under reaction conditions effective to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C. a major portion of the 3-hydroxypropanal so as 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 at least a portion of the cobalt catalyst or a cobalt-containing derivative thereof and at least a portion of the lipophilic quaternary ammonium salt;contacting the aqueous phase comprising 3-hydroxypropanal with hydrogen in, the presence of a hydrogenation catalyst at a pressure of at least about 100 psig and a temperature during at least a portion of the hydrogenation step of at least 40.degree. C. to provide a hydrogenation product mixture comprising 1,3-propanediol.
摘要翻译： 以包括以下步骤的方法制备1,3-丙二醇：在有效量的非磷化氢连接的钴催化剂存在下，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接触， 在有效量的亲油性季铵盐的温度范围为约50至约100℃，和a，压力范围为约500至约5000psig，在有效产生中间产物混合物的反应条件下，包括 小于15重量％的3-羟基丙醛; 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3-羟基丙醛的主要部分萃取到所述含水液体中，以提供包含比所述中间产物混合物更高浓度的3-羟基丙醛的水相， 所述中间产物混合物中的3-羟基丙醛的浓度和包含至少一部分钴催化剂或其含钴衍生物和至少一部分亲脂性季铵盐的有机相; 在氢化催化剂存在下，在至少约100psig的压力和在至少40℃的至少一部分氢化步骤期间的温度下使包含3-羟基丙醛的水相与氢接触以提供氢化 产物混合物包含1,3-丙二醇。
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公开(公告)号：US5463145A
公开(公告)日：1995-10-31
申请号：US316673
申请日：1994-09-30
CPC分类号： C07C29/141 , C07C29/16 , C07C45/58 , C07C45/80
摘要： 1,3-Propanediol is prepared in a process comprising the steps of:contacting, in an essentially non-water-miscible organic solvent, ethylene oxide with carbon monoxide and hydrogen in the presence of a catalytic amount of a non-phosphine-ligated cobalt compound and an effective amount of a lipophilic quaternary phosphonium salt 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 15 wt % 3-hydroxypropanal;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. to provide an aqueous phase comprising 3-hydroxypropanal in greater concentration than the concentration of 3-hydroxypropanal in the intermediate product mixture, and an organic phase comprising at least a portion of the cobalt compound and at least a portion of the lipophilic quaternary phosphonium salt;contacting the aqueous phase comprising 3-hydroxypropanal with hydrogen in the presence of a hydrogenation catalyst at a pressure of at least about 100 psig and a temperature during at least a portion of the hydrogenation step of at least 40.degree. C. to provide a hydrogenation product mixture comprising 1,3-propanediol.
摘要翻译： 以包括以下步骤的方法制备1,3-丙二醇：在催化量的非磷化氢连接的钴存在下，在基本上与水可混溶的有机溶剂中，使环氧乙烷与一氧化碳和氢气接触 化合物和有效量的亲脂性季鏻盐助催化剂，其温度范围为约50至约100℃，压力范围为约500至约5000psig，以产生包含较少量的中间产物混合物 超过15重量％的3-羟基丙醛; 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3-羟基丙醛的主要部分提取到所述水性液体中，以提供比3-浓度更高的浓度的3-羟基丙醛的水相 - 羟基丙醛，以及包含至少一部分钴化合物和至少一部分亲脂性季鏻盐的有机相; 在氢化催化剂的存在下，在至少约100psig的压力和在至少40℃的至少一部分氢化步骤期间的温度下使包含3-羟基丙醛的水相与氢气接触以提供氢化产物 混合物包含1,3-丙二醇。
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3.发明授权Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic dihydroxyarene promoter 失效使用亲脂性二羟基芳烃助催化剂制备1,3-丙二醇的钴催化方法
公开(公告)号：US5576471A
公开(公告)日：1996-11-19
申请号：US316669
申请日：1994-09-30
IPC分类号： C07C29/141 , C07C29/16 , C07C45/58 , C07C45/80 , C07C27/04
CPC分类号： C07C45/58 , C07C29/141 , C07C29/16 , C07C45/80
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 lipophilic dihydroxyarene 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 yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.
摘要翻译： 1,3-丁二醇的制备方法是在非磷化氢连接的钴催化剂和亲脂性二羟基芳烃助催化剂存在下，使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进行反应，生成中间体 含有小于15重量％的3-羟基丙醛的产物混合物; 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，而不需要使用膦配体改性的钴催化剂。
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公开(公告)号：US5463146A
公开(公告)日：1995-10-31
申请号：US316677
申请日：1994-09-30
CPC分类号： C07C45/58 , C07C29/141 , C07C29/16 , C07C45/80
摘要： 1,3-propanediol is prepared in a process comprising the steps of:(a) contacting 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 catalyst and an effective amount of a lipophilic arsine at a temperature within the range of about 50 to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;(b) adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C. a major portion of the 3-hydroxypropanal so as 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 at least a portion of the cobalt catalyst or a cobalt-containing derivative thereof and at least a portion of the lipophilic arsine;(c) separating the aqueous phase from the organic phase;(d) contacting the aqueous phase comprising 3-hydroxypropanal with hydrogen in the presence of a hydrogenation catalyst at a pressure of at least about 100 psig and a temperature during at least a portion of the hydrogenation step of at least 40.degree. C. to provide a hydrogenation product mixture comprising 1,3-propanediol;(e) recovering 1,3-propanediol from said hydrogenation product mixture; and(f) returning at least a portion of the organic phase comprising cobalt compound and lipophilic arsine to the process of step (a).The process enables the production of 1,3-propanediol in high yields and selectivity without the use of a phosphine-ligated cobalt catalyst.
摘要翻译： 以包括以下步骤的方法制备1,3-丙二醇：（a）在有效量的非磷化氢连接的钴的存在下，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接触 催化剂和有效量的亲油胂在约50至约100℃的温度和约500至约5000psig范围内的压力下，在有效产生包含较少的中间产物混合物的反应条件下 比约15重量％的3-羟基丙醛; （b）向所述中间产物混合物中加入含水液体并在低于约100℃的温度下将3-羟基丙醛的主要部分萃取到所述水性液体中，以提供含有更高浓度的3-羟基丙醛的水相 所述中间产物混合物中的3-羟基丙醛的浓度和包含至少一部分钴催化剂或其含钴衍生物和至少一部分亲脂性胂的有机相; （c）将水相与有机相分离; （d）在氢化催化剂的存在下，在至少约100psig的压力和至少一部分氢化步骤的至少40℃的温度下使包含3-羟基丙醛的水相与氢气接触，以提供 包含1,3-丙二醇的氢化产物混合物; （e）从所述氢化产物混合物回收1,3-丙二醇; 和（f）将包含钴化合物和亲脂性胂的至少一部分有机相返回到步骤（a）的方法。 该方法能够以高产率和选择性生产1,3-丙二醇，而不需要使用磷化氢连接的钴催化剂。
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5.发明授权Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic bidentate phosphine promotor 失效使用亲脂性二齿膦促进剂制备1,3-丙二醇的钴催化方法
公开(公告)号：US5545766A
公开(公告)日：1996-08-13
申请号：US316668
申请日：1994-09-30
IPC分类号： C07C29/141 , C07C29/16 , C07C45/58 , C07C29/36
CPC分类号： C07C29/16 , 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 lipophilic bidentate phosphine 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亲脂性二齿膦催化剂的存在下，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 含有小于15重量％的3-羟基丙醛的中间产物混合物; 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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6.发明授权Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic phosphine oxide promoter 失效使用亲脂性氧化膦促进剂制备1,3-丙二醇的钴催化方法
公开(公告)号：US5563302A
公开(公告)日：1996-10-08
申请号：US316680
申请日：1994-09-30
IPC分类号： C07C29/141 , C07C29/16 , C07C45/58 , C07C45/80 , C07C45/50
CPC分类号： C07C45/58 , C07C29/141 , C07C29/16 , C07C45/80
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 lipophilic phosphine oxide 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-hydroxpropanal 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 yields and selectively 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亲脂性氧化膦促进剂的存在下，将环氧乙烷与一氧化碳和氢气在基本上不与水混溶的溶剂中反应，以产生 含有小于15重量％的3-羟基丙醛的中间产物混合物; 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，并将含有3-羟基丙醛的水相与含钴催化剂的有机相分离; 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地制备1,3-丙二醇而不使用膦配体改性的钴催化剂。
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公开(公告)号：US5545767A
公开(公告)日：1996-08-13
申请号：US316679
申请日：1994-09-30
CPC分类号： C07C29/16 , C07C29/141 , C07C45/58
摘要： 1,3-propanediol is prepared in a process comprising the steps of:contacting 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 catalyst and an effective amount of a lipophilic phenol 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, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C. a major portion of the 3-hydroxypropanal so as 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 at least a portion of the cobalt catalyst or a cobalt-containing derivative thereof and at least a portion of the lipophilic phenol;contacting the aqueous phase comprising 3-hydroxypropanal with hydrogen in the presence of a hydrogenation catalyst at a pressure of at least about 100 psig and a temperature during at least a portion of the hydrogenation step of at least 40.degree. C. to provide a hydrogenation product mixture comprising 1,3-propanediol.
摘要翻译： 以包括以下步骤的方法制备1,3-丙二醇：在有效量的非磷化氢连接的钴催化剂存在下，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接触， 在约50℃至约100℃的温度范围内的有效量的亲油性苯酚和在约500至约5000psig范围内的压力，在有效产生包含小于约 15重量％3-羟基丙醛; 向所述中间产物混合物中加入水性液体并在小于约100℃的温度下将3-羟基丙醛的主要部分萃取到所述水性液体中，以提供包含比浓度更高的浓度的3-羟基丙醛的水相 所述中间产物混合物中的3-羟基丙醛和包含至少一部分钴催化剂或其含钴衍生物和至少一部分亲脂性酚的有机相; 在氢化催化剂的存在下，在至少约100psig的压力和在至少40℃的至少一部分氢化步骤期间的温度下使包含3-羟基丙醛的水相与氢气接触以提供氢化产物 混合物包含1,3-丙二醇。
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8.发明授权Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic quaternary arsonium salt promoter 失效使用亲脂性季铵盐助催化剂制备1,3-丙二醇的钴催化方法
公开(公告)号：US5545765A
公开(公告)日：1996-08-13
申请号：US316661
申请日：1994-09-30
IPC分类号： C07C29/141 , C07C29/16 , C07C45/58 , C07C27/04 , C07C45/00
CPC分类号： C07C29/16 , 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 lipophilic quaternary arsonium salt 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 yields 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亲脂性季铵盐助催化剂的存在下，使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，生成 含有小于15重量％的3-羟基丙醛的中间产物混合物; 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，而不需要使用膦配体改性的钴催化剂。
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9.发明授权Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic tertiary amine promoter 失效使用亲脂性叔胺助催化剂制备1,3-丙二醇的钴催化方法
公开(公告)号：US5585528A
公开(公告)日：1996-12-17
申请号：US316660
申请日：1994-09-30
CPC分类号： C07C45/58 , C07C29/141 , C07C29/16 , C07C45/80
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 lipophilic tertiary amine 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亲脂性叔胺促进剂的存在下，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 含有小于15重量％的3-羟基丙醛的中间产物混合物; 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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公开(公告)号：US5256827A
公开(公告)日：1993-10-26
申请号：US13834
申请日：1993-02-05
申请人： Lynn H. Slaugh , Paul R. Weider
发明人： Lynn H. Slaugh , Paul R. Weider
CPC分类号： C07C29/16 , C07C29/141 , C07C45/58
摘要： This invention relates to a process for making 3-hydroxypropanal and 1,3-propanediol which by intimately contacting(a) ethylene oxide,(b) tertiary phosphine-complexed cobalt carbonyl catalyst, wherein said phosphine, prior to being complexed with said cobalt carbonyl catalyst, is partially oxidized to provide an oxygen to phosphorus ratio no greater than about 0.5,(c) carbon monoxide, and(d) hydrogen, the molar ratio of carbon monoxide to hydrogen being from about 4:1 to about 1:6,in liquid-phase solution in an inert reaction solvent, at a temperature of from about 30.degree. C. to about 150.degree. C. and a pressure of from about 50 psi to about 10,000 psi. The use of the partially oxidized tertiary phosphine ligand enhances the activity of the catalyst.
摘要翻译： 本发明涉及一种制备3-羟基丙醛和1,3-丙二醇的方法，其通过使（a）环氧乙烷，（b）叔膦络合的羰基钴催化剂紧密接触，其中所述膦在与所述羰基钴络合之前 催化剂被部分氧化以提供不大于约0.5的氧磷比例，（c）一氧化碳和（d）氢，一氧化碳与氢的摩尔比为约4:1至约1:6， 在惰性反应溶剂中的液相溶液中，在约30℃至约150℃的温度和约50psi至约10,000psi的压力下进行。 使用部分氧化的叔膦配体增强催化剂的活性。
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