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    Process for preparing 1,3-propanediol
    1.
    发明授权
    Process for preparing 1,3-propanediol 失效
    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。

    Process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal in the presence of a hydration co-catalyst
    3.
    发明授权
    Process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal in the presence of a hydration co-catalyst 失效
    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。

    Method for removal of MW176 cyclic acetal formed during the production of 1,3-propanediol
    5.
    发明授权
    Method for removal of MW176 cyclic acetal formed during the production of 1,3-propanediol 失效
    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。

    Reduction of the viscosity of reactive heavy byproducts during the production of 1,3-propanediol
    6.
    发明授权
    Reduction of the viscosity of reactive heavy byproducts during the production of 1,3-propanediol 失效
    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。

    PROCESS FOR PREPARING 1,3-PROPANEDIOL
    7.
    发明申请
    PROCESS FOR PREPARING 1,3-PROPANEDIOL 失效
    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。

    Solid acid catalyzed reactive stripping of impurities formed during the production of 1, 3-propanediol
    8.
    发明授权
    Solid acid catalyzed reactive stripping of impurities formed during the production of 1, 3-propanediol 失效
    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。

    Process for hydrogenating an aldehyde
    9.
    发明授权
    Process for hydrogenating an aldehyde 失效
    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。