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1. 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。

2. 发明授权

US07381852B2 Process for hydrogenating an aldehyde 失效
标题翻译：氢化醛的方法
公开(公告)号：US07381852B2
公开(公告)日：2008-06-03
申请号：US11734194
申请日：2007-04-11
申请人： Glenn Charles Komplin , John Anthony Smegal
发明人： Glenn Charles Komplin , John Anthony Smegal
IPC分类号： C07C29/14
CPC分类号： B01J23/883 , B01J21/04 , B01J35/10 , B01J35/1014 , B01J37/0201 , C07C29/141 , C07C31/205
摘要： The present invention relates to a process for hydrogenating an aldehyde. An aldehyde is contacted with a catalyst comprising a support containing at least 95% α-alumina and non-support metals dispersed on the surface of the support. The non-support metals comprise nickel and/or one or more compounds thereof and molybdenum and/or one or more compounds thereof. The nickel and/or one or more compounds thereof comprise from 3 wt. % to 9 wt. % of the catalyst, by metallic weight, and the molybdenum and/or one or more compounds thereof comprise from 1 wt. % to 4 wt. % of the catalyst, by metallic weight.
摘要翻译：本发明涉及一种氢化醛的方法。醛与包含分散在载体表面上的至少95％α-氧化铝和非支撑金属的载体的催化剂接触。非支撑金属包含镍和/或其一种或多种化合物，钼和/或其一种或多种化合物。镍和/或其一种或多种化合物包含3wt。％至9重量％％的催化剂，通过金属重量，并且钼和/或其一种或多种化合物包含1wt。％至4wt。％的催化剂，以金属重量计。

3. 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。

4. 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。

5. 发明申请

US20120053381A1 INTEGRATED PROCESS TO PRODUCE C4+ HYDROCARBONS WITH REMOVAL OF BROMINATED ORGANIC IMPURITIES 有权
标题翻译：一体化生产C4 +碳氢化合物的方法，去除有机有机污染物
公开(公告)号：US20120053381A1
公开(公告)日：2012-03-01
申请号：US13319748
申请日：2010-05-11
申请人： Wayne Errol Evans , Glenn Charles Komplin , Duraisamy Muthusamy
发明人： Wayne Errol Evans , Glenn Charles Komplin , Duraisamy Muthusamy
IPC分类号： C07C1/26
CPC分类号： C07C2/76 , C07C15/04 , C07C15/08 , Y02P20/125 , C07C15/02
摘要： The present invention provides an integrated process for producing aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons from low molecular weight alkanes, which includes contacting the low molecular weight alkanes with a halogen and coupling the monohaloalkanes to form aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons.
摘要翻译：本发明提供了用于从低分子量烷烃生产芳族烃和/或C 4+非芳族烃的综合方法，其包括使低分子量烷烃与卤素接触并偶联单卤代烷烃形成芳族烃和/或C4 + 芳烃。

6. 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。

7. 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。

8. 发明申请

US20080154071A1 PROCESS FOR PREPARING 1,3-PROPANEDIOL 失效
标题翻译：制备1,3-丙二醇的方法
公开(公告)号：US20080154071A1
公开(公告)日：2008-06-26
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： C07C29/141
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。

9. 发明授权

US07335800B2 Hydrogenation catalyst and hydrogenation method 失效
标题翻译：氢化催化剂和氢化方法
公开(公告)号：US07335800B2
公开(公告)日：2008-02-26
申请号：US11409433
申请日：2006-04-21
申请人： Glenn Charles Komplin , John Anthony Smegal
发明人： Glenn Charles Komplin , John Anthony Smegal
IPC分类号： C07C29/14 , B01J21/08 , B01J23/28
CPC分类号： C12C11/02 , B01J23/8933 , B01J23/8986 , B01J23/8993 , C07C29/141 , C07C31/205
摘要： The present invention provides a hydrogenation catalyst effective for hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol. The hydrogenation catalyst comprises an α-alumina support, nickel, ruthenium, and a promoter. The nickel is deposited on the α-alumina support, and the ruthenium and the promoter are deposited on the nickel and the α-alumina support. The α-alumina support comprises at least 92 wt. % of the catalyst, and the nickel comprises from 1 wt. % to 6 wt. % of the catalyst. The present invention also provides a process of hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol with the catalyst.
摘要翻译：本发明提供了一种对3-羟基丙醛氢化成1,3-丙二醇有效的氢化催化剂。氢化催化剂包括α-氧化铝载体，镍，钌和助催化剂。镍沉积在α-氧化铝载体上，钌和助催化剂沉积在镍和α-氧化铝载体上。 α-氧化铝载体包含至少92wt。％的催化剂，并且镍包含1wt。％至6wt。％的催化剂。本发明还提供了使用该催化剂将3-羟基丙醛氢化成1,3-丙二醇的方法。

10. 发明授权

US06972346B2 Solid acid catalyzed reactive stripping of impurities formed during the production of 1, 3-propanediol 失效
标题翻译：在制备1,3-丙二醇期间形成的固体酸催化反应性汽提
公开(公告)号：US06972346B2
公开(公告)日：2005-12-06
申请号：US10676796
申请日：2003-10-01
申请人： Joseph Broun Powell , Paul Richard Weider , Glenn Charles Komplin
发明人： Joseph Broun Powell , Paul Richard Weider , Glenn Charles Komplin
IPC分类号： C07C29/141 , C07C29/80 , C07C29/88 , C07C31/18 , C07C27/26 , C07C27/28 , C07C29/74 , C07C31/20
CPC分类号： C07C29/141 , C07C29/80 , C07C29/88 , C07C31/205
摘要： A process for producing 1,3-propanediol comprising the steps of: a) forming an aqueous solution of 3-hydroxypropanal, b) hydrogenating the 3-hydroxypropanal to form a first crude 1,3-propanediol mixture comprising 1,3-propanediol, water, and MW 132 cyclic acetal, c) distilling the first crude 1,3-propanediol mixture to remove water and low boiling impurities and form a second crude 1,3-propanediol mixture, d) contacting the second crude 1,3-propanediol mixture with a solid acid purifier at a temperature of from about 50 to about 250° C. to convert the MW 132 cyclic acetal to more volatile cyclic acetals, and e) separating the more volatile cyclic acetals from the 1,3-propanediol by distillation or gas stripping.
摘要翻译：一种生产1,3-丙二醇的方法，包括以下步骤：a）形成3-羟基丙醛水溶液，b）氢化3-羟基丙醛以形成第一种1,3-丙二醇混合物，其包括1,3-丙二醇，水和MW 132环缩醛，c）蒸馏第一粗1,3-丙二醇混合物以除去水和低沸点杂质，并形成第二粗1,3-丙二醇混合物，d）使第二粗1,3-丙二醇与固体酸性净化器的混合物在约50至约250℃的温度下将MW 132环状缩醛转化为更易挥发的环状缩醛，以及e）通过蒸馏从1,3-丙二醇中分离更易挥发的环状缩醛或气体剥离。

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