公开(公告)号：US07307194B2

公开(公告)日：2007-12-11

申请号：US10580685

申请日：2005-10-27

申请人： Tilman Sirch ,  Gerd-Dieter Tebben ,  Ludwig E. Heck ,  Armin Diefenbacher ,  Alfred Krause ,  Franz Borgel

发明人： Tilman Sirch ,  Gerd-Dieter Tebben ,  Ludwig E. Heck ,  Armin Diefenbacher ,  Alfred Krause ,  Franz Borgel

IPC分类号： C07C31/20

CPC分类号： B01D61/025 ,  C07C29/149 ,  C07C31/20

摘要： The present invention provides a process for preparing 1,6-hexanediol from a carboxylic acid mixture which comprises adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols and is obtained as a by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol with oxygen or oxygen-containing gases and by water extraction of the reaction mixture, by esterification of the acids and hydrogenation, in which a) the mono- and dicarboxylic acids present in the aqueous dicarboxylic acid mixture are reacted with a low molecular weight alcohol to give the corresponding carboxylic esters, b) the resulting esterification mixture is freed of excess alcohol and low boilers in a first distillation stage, c) a separation of the bottom product is carried out in a second distillation stage into an ester fraction substantially free of 1,4-cyclohexanediols and a fraction comprising at least the majority of the 1,4-cyclohexanediols, d) the ester fraction substantially free of 1,4-cyclohexanediols is catalytically hydrogenated and e) 1,6-hexanediol is obtained in a purifying distillation stage from the hydrogenation effluent while removing an alcohol-low boiler mixture in a manner known per se, wherein alcohol is removed by a membrane system from the mixtures, obtained after the esterification in stage b) and/or after the hydrogenation in stage e), of alcohols and low boilers and recycled into the esterification.

摘要翻译： 本发明提供了由羧酸混合物制备1,6-己二醇的方法，该方法包括己二酸，6-羟基己酸和少量的1,4-环己二醇，并且作为副产物在环己烷氧化中得到， 环己酮/环己醇与氧或含氧气体反应，并通过酸的酸化和氢化水提取反应，其中a）存在于二羧酸水溶液混合物中的单羧酸和二羧酸与低分子量 重量醇以得到相应的羧酸酯，b）所得酯化混合物在第一蒸馏阶段中不含过量的醇和低沸点，c）将底部产物在第二蒸馏阶段中分离成基本上为酯馏分 不含1,4-环己烷二醇和至少包含大部分1,4-环己二醇的级分，d）酯级分基本上不含1， 4-环己烷二醇是催化氢化的，并且e）在纯化蒸馏阶段从氢化流出物中获得1,6-己二醇，同时以本身已知的方式除去醇低沸点混合物，其中醇通过膜系统从 在阶段b）和/或在步骤e）中的氢化后获得的醇和低锅炉中获得的并且再循环到酯化中的混合物。

公开(公告)号：US20080004475A1

公开(公告)日：2008-01-03

申请号：US11476161

申请日：2006-06-28

申请人： Tilman Sirch ,  Michael Steiniger ,  Steffen Mass ,  Stefan Rittinger ,  Stephan Schlitter ,  Ludwig E. Heck ,  Todd C. Spengeman ,  Jeffrey T. Andress

发明人： Tilman Sirch ,  Michael Steiniger ,  Steffen Mass ,  Stefan Rittinger ,  Stephan Schlitter ,  Ludwig E. Heck ,  Todd C. Spengeman ,  Jeffrey T. Andress

IPC分类号： C07C29/74

CPC分类号： C07C29/141 ,  C07C45/75 ,  C07C45/82 ,  C07C47/19 ,  C07C47/04 ,  C07C31/20 ,  C07C31/22 ,  C07C31/245

摘要： A process is provided for the preparation of polymethylol compounds of formula (I): (HOCH2)2—C—(R)2 ,   (I) in which the radicals R independently of one another are each a further methylol group, an alkyl group having from 1 to 22 C atoms or an aryl or aralkyl group having from 6 to 22 C atoms, by (a) condensing aldehydes having from 2 to 24 C atoms with formaldehyde in an aldol reaction using tertiary amines as a catalyst to give alkanals of formula (II): in which the radicals R independently of one another are each as defined above, (b) then separating, by distillation, the reaction mixture obtained into a bottom product comprising predominantly the compounds of formula II and a low-boiling stream consisting of unconverted or partially converted starting materials, and (c) hydrogenating the distillation bottom, wherein the aldol reaction is carried out with an aqueous formaldehyde solution having a methanol content of 0.35 to 0.5% by weight of methanol, the low-boiling stream is separated off at a pressure of 1 to 3 bar and temperatures of 100 to 135° C. and completely or partially recycled into the aldol reaction. This procedure advantageously makes it possible specifically to prevent the formation of by-products and hence to increase the yield of the desired polymethylol compound.We have found that this object is achieved by a process for the preparation of polymethylol compounds of formula (I): (HOCH2)2—C—(R)2 ,   (I) in which the radicals R independently of one another are each a further methylol group, an alkyl group having from 1 to 22 C atoms or an aryl or aralkyl group having from 6 to 22 C atoms, by (a) condensing aldehydes having from 2 to 24 C atoms with formaldehyde in an aldol reaction using tertiary amines as a catalyst to give alkanals of formula (II): in which the radicals R independently of one another are each as defined above, (b) then separating, by distillation, the reaction mixture obtained (aldolization product) into a bottom product comprising predominantly the compounds of formula II and a low-boiling stream consisting of unconverted or partially converted starting materials, and (c) hydrogenating the distillation bottom, wherein the aldol reaction is carried out with an aqueous formaldehyde solution having a methanol content of 0.35 to 0.5% by weight, the separation of the low-boiling stream is effected at a pressure of 1.1 to 3 bar, preferably 1.5 bar, and a temperature of 100 to 135° C., preferably of 102 to 125° C., and the low-boiling stream is completely or partially recycled into the aldol reaction, preferably the entire low-boiling stream being recycled. In the aldol reaction, a partially converted starting compound of formula (III): can also be formed in which the radicals R independently of one another are each hydrogen or are as defined above. According to the invention, this partially converted starting compound of formula (III), together with the desired alkanal of formula (II), is separated from the other by-products and the unreacted starting compounds and reacted again in an aldol reaction with formaldehyde having a methanol content of 0.35% by weight to 0.5% by weight, using tertiary amines as a catalyst.

公开(公告)号：US07544832B2

公开(公告)日：2009-06-09

申请号：US10503005

申请日：2002-02-15

申请人： Jan Peter Bredehöft ,  Hans-Jürgen Pallasch ,  Ludwig E. Heck ,  Eckhard Ströfer

发明人： Jan Peter Bredehöft ,  Hans-Jürgen Pallasch ,  Ludwig E. Heck ,  Eckhard Ströfer

IPC分类号： C07C249/00

CPC分类号： C07C263/10 ,  B01D3/322 ,  C07C265/14

摘要： An arrangement for carrying out chemical reactions comprises at least one distillation column and/or at least one container and at least one circulation evaporator, which are connected to one another via connecting elements, liquid being taken off completely or partly from a tray or from a stacked packing bed or from a dumped packing bed or from a liquid collector of the distillation column or being fed as an external feed stream below the lower tube sheet of the circulation evaporator to said evaporator.

摘要翻译： 用于进行化学反应的装置包括至少一个蒸馏塔和/或至少一个容器和至少一个循环蒸发器，所述至少一个循环蒸发器通过连接元件彼此连接，液体完全或部分地从托盘或从托盘 堆叠的填料床或来自倾倒的填料床或来自蒸馏塔的液体收集器，或者作为外部进料流供给到循环蒸发器的下管板下方到所述蒸发器。

公开(公告)号：US20120205308A1

公开(公告)日：2012-08-16

申请号：US13207266

申请日：2011-08-10

申请人： Julia Leschinski ,  Leo Denissen ,  Ludwig E. Heck ,  Peter Gammer ,  Bart Van De Voorde ,  Andreas Heußler ,  Samuel Neto

发明人： Julia Leschinski ,  Leo Denissen ,  Ludwig E. Heck ,  Peter Gammer ,  Bart Van De Voorde ,  Andreas Heußler ,  Samuel Neto

IPC分类号： C02F9/10

CPC分类号： C02F9/00 ,  C02F1/04 ,  C02F1/20 ,  C02F1/26 ,  C02F1/66 ,  C02F2103/36

摘要： The invention relates to a process for working up wastewaters which are obtained in the purification of crude aromatic nitro compounds after the nitration of aromatic compounds, comprising the following steps: (a) single-stage or multistage washing of the crude aromatic nitro compound to obtain at least one organic phase and at least one aqueous phase, and removal of the aqueous phase or of the aqueous phases, step (a) comprising the addition of a base other than ammonia, and then (b) optional removal of organic constituents from at least a portion of the aqueous phase or aqueous phases obtained in step (a) by stripping, preferably with steam, then (c) removal of organic compounds from at least a portion of the aqueous phase or aqueous phases resulting from step (a) or step (b) by thermal and/or oxidative degradation, then (d) distillative depletion of ammonia from at least a portion of the aqueous phase or aqueous phases resulting from step (c), and then (e) optional supply of at least a portion of the aqueous phase resulting from step (d) to a biological wastewater treatment.

摘要翻译： 本发明涉及一种处理在芳香族化合物硝化后的粗芳香族硝基化合物的净化中获得的废水的方法，其包括以下步骤：（a）粗芳族硝基化合物的单级或多级洗涤以获得 至少一个有机相和至少一个水相，以及水相或水相的除去，步骤（a）包括加入除氨以外的碱，然后（b）任选从其中除去有机成分 步骤（a）中获得的水相或水相的至少一部分通过汽提，优选用蒸汽，然后（c）从步骤（a）或（a）或（c）产生的水相或水相的至少一部分去除有机化合物， 步骤（b）通过热和/或氧化降解，然后（d）从步骤（c）产生的水相或水相的至少一部分蒸馏出氨，然后（e）可选地提供 将由步骤（d）得到的水相的一部分转化为生物废水处理。