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    • 3. 发明申请
    • Method for the production of 1,4- butane-diol by combined gas-phase and liquid-phase hydrogenation
    • 通过组合气相和液相氢化生产1,4-丁二醇的方法
    • US20050267318A1
    • 2005-12-01
    • US10516923
    • 2003-06-10
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RoschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RoschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • B01J23/80C07B61/00C07C29/149C07C31/20C07C31/18
    • C07C29/149C07C31/207
    • The present invention relates to a process for preparing optionally alkyl-substituted 1,4-butanediol by two-stage catalytic hydrogenation in the gas phase of C4-dicarboxylic acids and/or of derivatives thereof having the following steps: a) introducing a gas stream of a C4-dicarboxylic acid or of a derivative thereof at from 200 to 300° C. and from 2 to 60 bar into a first reactor and catalytically hydrogenating it to a product which contains mainly optionally alkyl-substituted 7-butyrolactone; b) converting the product stream into the liquid phase; c) introducing the product stream obtained in this way into a second reactor at a temperature of from 100° C. to 240° C. and a pressure of from 20 to 250 bar and catalytically hydrogenating it in the liquid phase to optionally alkyl-substituted 1,4-butanediol; d) removing the desired product from by-products and any unconverted reactants; e) optionally recycling unconverted intermediates into one or both hydrogenation stages, said hydrogenation stages both using a catalyst which comprises ≦95% by weight, preferably from 5 to 95% by weight, in particular from 10 to 80% by weight, of CuO, and ≧5% by weight, preferably from 5 to 95% by weight, in particular from 20 to 90% by weight, of a support, said second reactor having a higher pressure than said first reactor, and the product mixture removed from said first reactor being introduced without further purification into said second reactor.
    • 本发明涉及通过在具有下列物质的C 4 - 二羧酸和/或其衍生物的气相中通过两阶段催化氢化制备任选的烷基取代的1,4-丁二醇的方法 步骤:a)将200-300℃和2-60巴的C 4-14二羧酸或其衍生物的气流引入第一反应器,并将其催化氢化至 主要含有烷基取代的7-丁内酯的产物; b)将产物流转化成液相; c)将以这种方式获得的产物流在100℃至240℃的温度和20至250巴的压力下引入第二反应器,并将其在液相中催化氢化为任选的烷基取代的 1,4-丁二醇 d)从副产物和任何未转化的反应物中除去所需的产物; e)任选地将未转化的中间体再循环到一个或两个氢化阶段中,所述氢化步骤均使用包含<= 95重量%,优选5至95重量%,特别是10至80重量%的CuO ,和> = 5重量%,优选5至95重量%,特别是20至90重量%的载体,所述第二反应器具有比所述第一反应器更高的压力,并将产物混合物从 所述第一反应器不经进一步纯化地引入所述第二反应器。
    • 4. 发明申请
    • Method for the production of 1,4- butanediol
    • 1,4-丁二醇生产方法
    • US20050182281A1
    • 2005-08-18
    • US10517263
    • 2003-06-10
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RoschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RoschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • C07B61/00C07C29/149C07C31/20C07C31/18
    • C07C29/149Y02P20/582C07C31/207
    • The present invention relates to a process for preparing optionally alkyl-substituted 1,4-butanediol by two-stage catalytic hydrogenation in the gas phase of C4-dicarboxylic acids and/or of derivatives thereof having the following steps: a) introducing a gas stream of a C4-dicarboxylic acid or of a derivative thereof at from 200 to 300° C. and from 10 to 100 bar into a first reactor or into a first reaction zone of a reactor and catalytically hydrogenating it in the gas phase to a product which contains mainly optionally alkyl-substituted y-butyrolactone; b) introducing the product stream obtained in this way into a second reactor or into a second reaction zone of a reactor at a temperature of from 140° C to 260° C. and catalytically hydrogenating it in the gas phase to optionally alkyl-substituted 1,4-butanediol; steps a) and b) being carried out at the same pressure; c) removing the desired product from intermediates, by-products and any unconverted reactants; d) optionally recycling unconverted intermediates into one or both hydrogenation stages, said hydrogenation stages each using a catalyst which comprises ≦95% by weight, preferably from 5 to 95% by weight, in particular from 10 to 80% by weight, of CuO, and ≧5% by weight, preferably from 5 to 95% by weight, in particular from 20 to 90% by weight, of an oxidic support, and the product mixture removed from the first hydrogenation stage being introduced without further purification into the second hydrogenation stage.
    • 本发明涉及通过在具有下列物质的C 4 - 二羧酸和/或其衍生物的气相中通过两阶段催化氢化制备任选的烷基取代的1,4-丁二醇的方法 步骤:a)将200-300℃和10-100巴的C 4-14二羧酸或其衍生物的气流引入第一反应器或第一反应 并将其在气相中催化氢化成主要包含烷基取代的γ-丁内酯的产物; b)将以这种方式获得的产物流引入第二反应器或反应器的第二反应区,温度为140℃至260℃,并将其在气相中催化氢化为任选烷基取代的1 ,4-丁二醇; 步骤a)和b)在相同的压力下进行; c)从中间体,副产物和任何未转化的反应物中除去所需的产物; d)任选地将未转化的中间体再循环到一个或两个氢化阶段中,所述氢化阶段各自使用包含<= 95重量%,优选5至95重量%,特别是10至80重量%的CuO ,和> = 5重量%,优选5至95重量%,特别是20至90重量%的氧化载体,并将从第一氢化步骤除去的产物混合物不经进一步纯化引入到 第二加氢阶段。
    • 6. 发明授权
    • Method for the production of 1,4- butane-diol by combined gas-phase and liquid-phase hydrogenation
    • 通过组合气相和液相氢化生产1,4-丁二醇的方法
    • US07169958B2
    • 2007-01-30
    • US10516923
    • 2003-06-10
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RöschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RöschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • C07C29/132C07C29/149C07C29/136C07C29/147
    • C07C29/149C07C31/207
    • The present invention relates to a process for preparing optionally alkyl-substituted 1,4-butanediol by two-stage catalytic hydrogenation in the gas phase of C4-dicarboxylic acids and/or of derivatives thereof having the following steps: a) introducing a gas stream of a C4-dicarboxylic acid or of a derivative thereof at from 200 to 300° C. and from 2 to 60 bar into a first reactor and catalytically hydrogenating it to a product which contains mainly optionally alkyl-substituted γ-butyrolactone; b) converting the product stream into the liquid phase; c) introducing the product stream obtained in this way into a second reactor at a temperature of from 100° C. to 240° C. and a pressure of from 20 to 250 bar and catalytically hydrogenating it in the liquid phase to optionally alkyl-substituted 1,4-butanediol; d) removing the desired product from by-products and any unconverted reactants; e) optionally recycling unconverted intermediates into one or both hydrogenation stages, said hydrogenation stages both using a catalyst which comprises ≦95% by weight, preferably from 5 to 95% by weight, in particular from 10 to 80% by weight, of CuO, and ≧5% by weight, preferably from 5 to 95% by weight, in particular from 20 to 90% by weight, of a support, said second reactor having a higher pressure than said first reactor, and the product mixture removed from said first reactor being introduced without further purification into said second reactor.
    • 本发明涉及通过在具有下列物质的C 4 - 二羧酸和/或其衍生物的气相中通过两阶段催化氢化制备任选的烷基取代的1,4-丁二醇的方法 步骤:a)将200-300℃和2-60巴的C 4-14二羧酸或其衍生物的气流引入第一反应器,并将其催化氢化至 主要含烷基取代的γ-丁内酯的产品; b)将产物流转化成液相; c)将以这种方式获得的产物流在100℃至240℃的温度和20至250巴的压力下引入第二反应器,并将其在液相中催化氢化为任选的烷基取代的 1,4-丁二醇 d)从副产物和任何未转化的反应物中除去所需的产物; e)任选地将未转化的中间体再循环到一个或两个氢化阶段中,所述氢化步骤均使用包含<= 95重量%,优选5至95重量%,特别是10至80重量%的CuO ,和> = 5重量%,优选5至95重量%,特别是20至90重量%的载体,所述第二反应器具有比所述第一反应器更高的压力,并将产物混合物从 所述第一反应器不经进一步纯化地引入所述第二反应器。
    • 7. 发明授权
    • Method for the production of 1,4- butanediol
    • 1,4-丁二醇生产方法
    • US07154011B2
    • 2006-12-26
    • US10517263
    • 2003-06-10
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RöschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • Michael HesseStephan SchlitterHolger BorchertMarkus SchubertMarkus RöschNils BottkeRolf-Hartmuth FischerAlexander WeckGunther WindeckerGunnar Heydrich
    • C07C29/149
    • C07C29/149Y02P20/582C07C31/207
    • The present invention relates to a process for preparing optionally alkyl-substituted 1,4-butanediol by two-stage catalytic hydrogenation in the gas phase of C4-dicarboxylic acids and/or of derivatives thereof having the following steps: a) introducing a gas stream of a C4-dicarboxylic acid or of a derivative thereof at from 200 to 300° C. and from 10 to 100 bar into a first reactor or into a first reaction zone of a reactor and catalytically hydrogenating it in the gas phase to a product which contains mainly optionally alkyl-substituted γ-butyrolactone; b) introducing the product stream obtained in this way into a second reactor or into a second reaction zone of a reactor at a temperature of from 140° C. to 260° C. and catalytically hydrogenating it in the gas phase to optionally alkyl-substituted 1,4-butanediol; steps a) and b) being carried out at the same pressure; c) removing the desired product from intermediates, by-products and any unconverted reactants; d) optionally recycling unconverted intermediates into one or both hydrogenation stages, said hydrogenation stages each using a catalyst which comprises ≦95% by weight, preferably from 5 to 95% by weight, in particular from 10 to 80% by weight, of CuO, and ≧5% by weight, preferably from 5 to 95% by weight, in particular from 20 to 90% by weight, of an oxidic support, and the product mixture removed from the first hydrogenation stage being introduced without further purification into the second hydrogenation stage.
    • 本发明涉及通过在具有下列物质的C 4 - 二羧酸和/或其衍生物的气相中通过两阶段催化氢化制备任选的烷基取代的1,4-丁二醇的方法 步骤:a)将200-300℃和10-100巴的C 4-14二羧酸或其衍生物的气流引入第一反应器或第一反应 并将其在气相中催化氢化成主要包含烷基取代的γ-丁内酯的产物; b)将以这种方式获得的产物流在140℃至260℃的温度下引入第二反应器或反应器的第二反应区,并将其在气相中催化氢化为任选的烷基取代的 1,4-丁二醇 步骤a)和b)在相同的压力下进行; c)从中间体,副产物和任何未转化的反应物中除去所需的产物; d)任选地将未转化的中间体再循环到一个或两个氢化阶段中,所述氢化阶段各自使用包含<= 95重量%,优选5至95重量%,特别是10至80重量%的CuO ,和> = 5重量%,优选5至95重量%,特别是20至90重量%的氧化载体,并将从第一氢化步骤除去的产物混合物不经进一步纯化引入到 第二加氢阶段。
    • 9. 发明申请
    • Method for the simultaneous production of tetrahydrofurans ad pyrrolidones
    • 同时生产四氢呋喃和吡咯烷酮的方法
    • US20050119494A1
    • 2005-06-02
    • US10505706
    • 2003-02-28
    • Rolf-Hartmuth FischerMarkus RoschNils BottkeAlexander WeckGunther WindeckerMichael HesseHolger BorchertStephan Schlitter
    • Rolf-Hartmuth FischerMarkus RoschNils BottkeAlexander WeckGunther WindeckerMichael HesseHolger BorchertStephan Schlitter
    • B01J23/72B01J23/80C07B61/00C07D207/26C07D207/267C07D307/08C07D307/02
    • C07D207/267C07D307/08
    • A process for coproducing alkyl-substituted or unsubstituted THF and pyrrolidones by catalytically hydrogenating C4-dicarboxylic acids and/or derivatives thereof in the gas phase in the presence of copper catalysts and reacting GBL with ammonia or primary amines to give pyrrolidones comprises a) hydrogenating C4-dicarboxylic acids and/or derivatives thereof in the gas phase at from 200 to 300° C., from 0.1 to 100 bar, catalyst hourly space velocities of from 0.01 to 1 kg of reactant/l of catalyst*hour and reactant/hydrogen molar ratios of from 20 to 800 in the presence of catalysts comprising copper, aluminum and/or zinc to give mixtures of THF and GBL, b) separating the hydrogenation effluent obtained by distillation into a THF/water mixture as the top product and a GBL-containing bottom product, c) separating the THF/water mixture from step b) in a distillation facility consisting of three columns by withdrawing water from the bottom of the first column, recycling water-containing THF from the second into the first column, passing a side stream of the first into the second column, recycling the bottom product of the third column into the first column and withdrawing a distillate at the top of the first column, wherein a side stream of the second column is passed into the third column and the pure THF is obtained as the top product of the third column, d) recovering GBL from the GBL-containing bottom product from step b) by distillation and e) reacting the GBL obtained with ammonia or amines to give corresponding pyrrolidones.
    • 在铜催化剂存在下,在气相中催化氢化C 4 - 二羧酸和/或其衍生物,共同生产烷基取代或未取代的THF和吡咯烷酮的方法,并使GBL与氨或伯胺 得到吡咯烷酮包括:a)在200-300℃,0.1-100巴的气相中氢化C 4-14 - 二羧酸和/或其衍生物,催化剂小时空速为0.01 在包含铜,铝和/或锌的催化剂存在下,至1kg反应物/ l催化剂*小时和反应物/氢摩尔比为20至800,得到THF和GBL的混合物,b)分离所得氢化流出物 通过蒸馏作为顶部产物的THF /水混合物和含有GBL的底部产物,c)通过从第一塔底部排出水分离由三塔组成的蒸馏设备中的步骤b)中的THF /水混合物 ,回收 将含水THF从第二塔进入第一塔,将第一塔的侧流通入第二塔,将第三塔的底部产物再循环到第一塔中并抽出第一塔顶部的馏出物,其中 将第二塔的侧流进入第三塔,得到纯THF作为第三塔的顶部产物,d)通过蒸馏从步骤b)的含GBL的底部产物中回收GBL,和e)使 用氨或胺得到GBL,得到相应的吡咯烷酮。