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21. 发明授权

US07276634B2 Reduction of the viscosity of reactive heavy byproducts during the production of 1,3-propanediol 失效
标题翻译：在1,3-丙二醇生产过程中降低反应性重副产物的粘度
公开(公告)号：US07276634B2
公开(公告)日：2007-10-02
申请号：US10676682
申请日：2003-10-01
申请人： John Frederick Knifton , Talmadge Gail James , Paul Richard Weider , Joseph Broun Powell , Edward Lewis Nielsen , Glenn Charles Komplin
发明人： John Frederick Knifton , Talmadge Gail James , Paul Richard Weider , Joseph Broun Powell , Edward Lewis Nielsen , Glenn Charles Komplin
IPC分类号： C07C27/10
CPC分类号： C07C45/58 , C07C29/141 , C07C31/205
摘要： The present invention is an improvement upon the process for the production of 1,3-propanediol wherein an aqueous solution of 3-hydroxy propanal is formed, catalyst, if any, used in said formation is removed from the solution, sodium hydroxide is added to the solution to neutralize any acid therein such that the pH is at least about 5, the neutralized aqueous solution is subjected to hydrogenation to produce a crude 1,3-propanediol mixture which is distilled to produce 1,3-propanediol, water, and reactive heavy components. The improvement on this process comprises replacing the sodium hydroxide with a hydroxide selected from the group consisting of ammonium hydroxide, alkali metal hydroxides other than sodium hydroxide, and alkaline earth metal hydroxides to reduce the viscosity of the reactive heavy components.
摘要翻译：本发明是对生产1,3-丙二醇的方法的改进，其中形成3-羟基丙醛的水溶液，从该溶液中除去所述地层中使用的催化剂（如果有的话），将氢氧化钠加入中和其中的任何酸使其pH至少约为5的溶液，中和的水溶液进行氢化以产生粗制的1,3-丙二醇混合物，其被蒸馏以产生1,3-丙二醇，水和反应性重组件。该方法的改进包括用选自氢氧化铵，氢氧化钠以外的碱金属氢氧化物和碱土金属氢氧化物的氢氧化物代替氢氧化钠，以降低反应性重组分的粘度。

22. 发明授权

US5770776A 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：US5770776A
公开(公告)日：1998-06-23
申请号：US615544
申请日：1996-03-11
申请人： Joseph Broun Powell , Stephen Blake Mullin , Paul Richard Weider , David Cleve Eubanks , Juan Pedro Arhancet
发明人： Joseph Broun Powell , Stephen Blake Mullin , Paul Richard Weider , David Cleve Eubanks , Juan Pedro Arhancet
IPC分类号： B01J31/20 , C07C29/141 , C07C29/16 , C07C45/58 , C07C45/80 , C07C29/36
CPC分类号： C07C29/16 , B01J31/0268 , B01J31/04 , B01J31/20 , B01J31/2234 , B01J31/26 , B01J31/4046 , C07C29/141 , C07C45/58 , C07C45/80 , B01J2231/48 , B01J2531/822 , Y02P20/52 , Y02P20/584
摘要： 1,3-propanediol is prepared in a process in which ethylene oxide is reacted 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 catalyst promoter under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal. The 3-hydroxypropanal is extracted in water from the product mixture in more concentrated form, with the majority of the cobalt catalyst remaining in the solvent phase for recycle to the hydroformylation reaction. At least a portion of any residual catalyst in the water phase following extraction is removed by re-extraction with non-water-miscible solvent and recycled to hydroformylation. The 3-hydroxypropanal is then hydrogenated in aqueous solution to the desired 1,3-propanediol.
摘要翻译：在有效量的非磷化氢连接的钴催化剂和有效量的存在下，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的方法制备1,3-丙二醇的催化剂促进剂在有效产生包含小于约15重量％3-羟基丙醛的中间产物混合物的反应条件下进行。 3-羟基丙醛在水中以更浓缩的形式从产物混合物中提取，大部分钴催化剂保留在溶剂相中循环进行加氢甲酰化反应。提取后的水相中的任何残留催化剂的至少一部分通过用非水混溶性溶剂重新萃取除去并再循环至加氢甲酰化反应。然后将3-羟基丙醛水溶液加氢至所需的1,3-丙二醇。

23. 发明申请

US20090163742A1 HETEROGENEOUS PROMOTION OF OXIRANE HYDROFORMYLATION 审中-公开
标题翻译：异构促进氧化水解
公开(公告)号：US20090163742A1
公开(公告)日：2009-06-25
申请号：US12337374
申请日：2008-12-17
申请人： Stephen Blake Mullin , Joseph Broun Powell , Paul Richard Weider
发明人： Stephen Blake Mullin , Joseph Broun Powell , Paul Richard Weider
IPC分类号： C07C45/00
CPC分类号： C07C45/58 , C07C47/19
摘要： A process for making betahydroxyaldehydes such as 3-hydroxypropanal which comprises intimately contacting (a) an oxirane, (b) carbon monoxide, (c) a reducing agent such as hydrogen, (d) from about 0.01 to about 1 weight percent, basis cobalt metal, of a cobalt hydroformylation catalyst which is optionally complexed with a tertiary phosphine ligand, and (e) a heterogeneous, preferably solid, metal promoter used at a molar ratio of 0.05, preferably 0.15, to 100 moles of heterogeneous metal relative to the moles of soluble cobalt hydroformylation catalyst.
摘要翻译：一种制备β-羟基醛例如3-羟基丙醛的方法，其包括使（a）环氧乙烷，（b）一氧化碳，（c）还原剂如氢气，（d）约0.01至约1重量％金属，钴加氢甲酰化催化剂，其任选与叔膦配体络合，和（e）非均相的，优选固体的金属促进剂，其摩尔比为0.05，优选0.15至100摩尔异相金属，相对于摩尔数的可溶性羰基羰基化催化剂。

24. 发明申请

US20070179322A1 METHOD OF TREATING AN ALDEHYDE MIXTURE, USE OF THE TREATED ALDEHYDE, AND AN ALCOHOL 失效
标题翻译：处理ALDEHYDE MIXTURE的方法，处理的ALDEHYDE的使用和醇
公开(公告)号：US20070179322A1
公开(公告)日：2007-08-02
申请号：US11669694
申请日：2007-01-31
申请人： Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
发明人： Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
IPC分类号： C07C45/85
CPC分类号： C07C45/78 , C07C29/141 , C07C45/49 , C07C45/58 , C07C45/79 , C07C45/80 , C07C45/85 , C07C47/19 , C07C31/205
摘要： A method of treating an aldehyde mixture comprising a carboxylic acid and a metal cation, which method comprises: contacting the aldehyde mixture with a basic separating medium, and subsequently or simultaneously contacting with an acidic separating medium; use of the treated aldehyde mixture to prepare an alcohol; and the alcohol.
摘要翻译：一种处理包含羧酸和金属阳离子的醛混合物的方法，该方法包括：使醛混合物与碱性分离介质接触，随后或同时与酸性分离介质接触; 使用经处理的醛混合物制备醇; 和酒精。

25. 发明授权

US06969779B2 Method for removal of MW176 cyclic acetal formed during the production of 1,3-propanediol 失效
标题翻译：在1,3-丙二醇生产过程中形成的MW176环状缩醛的去除方法
公开(公告)号：US06969779B2
公开(公告)日：2005-11-29
申请号：US10676690
申请日：2003-10-01
申请人： Stephen Edward Brewer , Zaida Diaz , Joseph Broun Powell , Paul Richard Weider , Glenn Charles Komplin , Robert Lawrence Blackbourn
发明人： Stephen Edward Brewer , Zaida Diaz , Joseph Broun Powell , Paul Richard Weider , Glenn Charles Komplin , Robert Lawrence Blackbourn
IPC分类号： C07C29/141 , C07C29/80 , C07C29/88 , C07C27/04 , C07C27/26 , C07C29/14 , C07C29/74 , C07C31/18
CPC分类号： C07C29/141 , C07C29/80 , C07C29/88 , C07C31/205
摘要： The present invention is an improvement upon the process for the production of 1,3-propanediol (PDO) wherein an aqueous solution of 3-hydroxypropanal (HPA) is formed, and the HPA is subjected to hydrogenation to produce a crude PDO mixture comprising PDO, water, MW176 acetal, and high and low volatility materials, wherein the crude PDO mixture is dried to produce a first overhead stream comprising water and some high volatility materials and a dried crude PDO mixture as a first distillate bottoms stream comprising PDO, MW176 acetal, and low volatility materials, and wherein the dried crude PDO mixture is distilled to produce a second overhead stream comprising some high volatility materials, a middle stream comprising PDO and MW176 acetal, and a second distillate bottoms stream comprising PDO and low volatility materials. The improvement on this process comprises treating the crude PDO mixture and/or the dried crude PDO mixture and/or the PDO product with an acidic zeolite, an acid form cation exchange resin, or a soluble acid to convert the MW176 cyclic acetal to more volatile materials which can be easily separated from PDO by distillation.
摘要翻译：本发明是制备其中形成3-羟基丙醛（HPA）的水溶液的1,3-丙二醇（PDO）的方法的改进，并且将HPA进行氢化以制备包含PDO的粗制PDO混合物，水，MW176缩醛和高低挥发性材料，其中将粗PDO混合物干燥以产生包含水和一些高挥发性材料的第一塔顶料流，以及干燥的粗PDO混合物作为包含PDO，MW176缩醛的第一馏出物塔底料流和低挥发性材料，并且其中将干燥的粗PDO混合物蒸馏以产生包含一些高挥发性材料的第二塔顶料流，包含PDO和MW176缩醛的中间料流和包含PDO和低挥发性材料的第二馏出物塔底料流。该方法的改进包括用酸性沸石，酸形阳离子交换树脂或可溶性酸处理粗PDO混合物和/或干燥的粗PDO混合物和/或PDO产物，以将MW176环状缩醛转化为更易挥发的可以通过蒸馏容易地与PDO分离的材料。

26. 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。

27. 发明授权

US07385090B2 Method of treating an aldehyde mixture, use of the treated aldehyde, and an alcohol 失效
标题翻译：处理醛混合物的方法，使用经处理的醛和醇
公开(公告)号：US07385090B2
公开(公告)日：2008-06-10
申请号：US11669694
申请日：2007-01-31
申请人： Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
发明人： Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
IPC分类号： C07C45/78 , C07C31/18
CPC分类号： C07C45/78 , C07C29/141 , C07C45/49 , C07C45/58 , C07C45/79 , C07C45/80 , C07C45/85 , C07C47/19 , C07C31/205
摘要： A method of treating an aldehyde mixture comprising a carboxylic acid and a metal cation, which method comprises: contacting the aldehyde mixture with a basic separating medium, and subsequently or simultaneously contacting with an acidic separating medium; use of the treated aldehyde mixture to prepare an alcohol; and the alcohol.
摘要翻译：一种处理包含羧酸和金属阳离子的醛混合物的方法，该方法包括：使醛混合物与碱性分离介质接触，随后或同时与酸性分离介质接触; 使用经处理的醛混合物制备醇; 和酒精。

28. 发明授权

US07329785B2 Process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal in the presence of a hydration co-catalyst 失效
标题翻译：在水合助催化剂存在下通过3-羟基丙醛的催化氢化生产1,3-丙二醇的方法
公开(公告)号：US07329785B2
公开(公告)日：2008-02-12
申请号：US10958938
申请日：2004-10-05
申请人： Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
发明人： Glenn Charles Komplin , Joseph Broun Powell , Paul Richard Weider
IPC分类号： C07C27/04 , C07C29/14 , C07C31/18
CPC分类号： C07C29/141 , C07C31/205
摘要： A process for preparing 1,3-propanediol comprising the steps of: (a) preparing an aqueous mixture of 3-hydroxypropanal, (b) passing said aqueous 3-hydroxypropanal mixture to a hydrogenation zone wherein the hydrogenation zone is comprised of at least two stages wherein the hydrogenation in the first stage is carried out under hydrogenation conditions at a temperature in the range of about 50 to about 130° C. in the presence of a fixed bed or slurry hydrogenation catalyst and wherein an acidic co-catalyst is added or present in at least one of the later stages and the hydrogenation in said later stages is carried out under hydrogenation conditions at a higher temperature than that of the first hydrogenation stage and in the range of about 70 to about 155° C. to form an aqueous solution of 1,3-propanediol; and (c) recovering said 1,3-propanediol.
摘要翻译：一种制备1,3-丙二醇的方法，包括以下步骤：（a）制备3-羟基丙醛的水性混合物，（b）将所述3-羟基丙醛水溶液通入氢化区，其中氢化区由至少两个阶段，其中第一阶段的氢化在氢化条件下在约50至约130℃的温度下在固定床或浆料氢化催化剂的存在下进行，并且其中加入酸性助催化剂或存在于后期的至少一个阶段和所述后期的氢化在氢化条件下在比第一氢化阶段高的温度下进行，并且在约70至约155℃的范围内进行，以形成水 1,3-丙二醇溶液; 和（c）回收所述1,3-丙二醇。

29. 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。

30. 发明授权

US5986145A Purification of 3-hydroxy-propanal 失效
标题翻译：纯化3-羟基 - 丙醛
公开(公告)号：US5986145A
公开(公告)日：1999-11-16
申请号：US138314
申请日：1998-08-21
申请人： Joseph Broun Powell , Paul Richard Weider , Robert Lawrence Blackbourn , Stephen Blake Mullin
发明人： Joseph Broun Powell , Paul Richard Weider , Robert Lawrence Blackbourn , Stephen Blake Mullin
IPC分类号： B01J31/40 , C07C45/58 , C07C45/79 , C07C45/85 , C07C45/00
CPC分类号： B01J31/20 , B01J31/403 , B01J31/4046 , B01J31/4092 , C07C45/58 , C07C45/79 , C07C45/85 , B01J2231/48 , B01J2531/822 , B01J2531/845 , B01J31/08 , Y02P20/584
摘要： Cobalt or rhodium carbonyl compounds are removed from an aqueous solution of 3-hydroxypropanal by a process comprising the steps of:(a) contacting the 3-hydroxypropanal solution with oxygen under acidic conditions at a temperature within the range of about 5 to about 45.degree. C. to produce an oxidation product mixture comprising an aqueous solution of 3-hydroxypropanal, one or more water-soluble cobalt or rhodium species, and byproduct carbon monoxide;(b) removing byproduct carbon monoxide from the oxidation product mixture as it is generated; and(c) passing the oxidation product mixture in contact with an acidic ion exchange resin maintained at a temperature less than about 45.degree. C. and removing at least a portion of the soluble metal compounds from the oxidation product mixture.Such a process is useful in, for example, the manufacture of 1,3-propanediol from ethylene oxide via an intermediate 3-hydroxypropanal solution containing residual carbon dioxide and insoluble cobalt or rhodium catalyst compounds.
摘要翻译：通过包括以下步骤的方法从3-羟基丙醛水溶液中除去羰基钴或铑羰基化合物：（a）在酸性条件下在约5至约45℃的温度范围内使3-羟基丙醛溶液与氧接触以产生包含3-羟基丙醛水溶液，一种或多种水溶性钴或铑物质和副产物一氧化碳的氧化产物混合物; （b）在生成氧化产物混合物时从副产物一氧化碳中除去; 和（c）使氧化产物混合物与保持在低于约45℃温度的酸性离子交换树脂接触，并从氧化产物混合物中除去至少一部分可溶性金属化合物。这种方法可用于例如通过含有残余二氧化碳和不溶性钴或铑催化剂化合物的中间体3-羟基丙醛溶液从环氧乙烷制备1,3-丙二醇。

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