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1. 发明授权

US06790995B2 Preparation of primary and secondary amines from nitriles 失效
标题翻译：从腈制备伯胺和仲胺
公开(公告)号：US06790995B2
公开(公告)日：2004-09-14
申请号：US10033912
申请日：2002-01-03
申请人： Joachim Pfeffinger , Michael Hüllmann , Arthur Höhn , Frank Funke , Frank Ohlbach , Till Gerlach
发明人： Joachim Pfeffinger , Michael Hüllmann , Arthur Höhn , Frank Funke , Frank Ohlbach , Till Gerlach
IPC分类号： C07C20948
CPC分类号： C07C213/02 , C07C209/48 , C07C211/11 , C07C215/08
摘要： Mixtures of primary amines of the formula (I) X—CH2—NH2 (I) and secondary amines of the formula (II) (X—CH2—)2NH (II) where X is C1-20-alkyl, C2-20-alkenyl or C3-8-cycloalkyl which may be unsubstituted or substituted by C1-20-alkyl, C3-8-cycloalkyl, C4-20-alkylcycloalkyl, C4-20-cycloalkylalkyl, C2-20-alkoxyalkyl, C6-14-aryl, C7-20-alkylaryl, C7-20-aralkyl, C1-20-alkoxy, hydroxy, C1-20-hydroxyalkyl, amino, C1-20-alkylamino, C2-20-dialkylamino, C2-12-alkenylamino. C3-8-cycloalkylamino, arylamino, diarylamino, aryl-C1-8-alkylamino, halogen, mercapto, C2-20-alkenyloxy, C3-8-cycloalkoxy, aryloxy and/or C2-8-alkoxycarbonyl are prepared by reacting nitriles of the formula (III) X—CN (III) with hydrogen at from 50 to 250° C. and pressures of from 5 to 350 bar in the presence of a Pd-containing catalyst comprising, based on the total weight of the catalyst, from 0.1 to 10% by weight of Pd on a support.
摘要翻译：式（I）的伯胺和式（II）的仲胺的混合物，其中X是可以未被取代或被C 1-20烷基取代的C 1-20 - 烷基，C 2-20 - 烯基或C 3-8 - 环烷基，C 3-8 - 环烷基，C 4-20 - 烷基环烷基，C 4-20 - 环烷基烷基，C 2-20烷氧基烷基，C 6-14 - 芳基，C 7-20 - 烷基芳基，C 7-20 - 芳烷基，C 1-20 - 烷氧基，羟基，C 1-20羟烷基，氨基，C 1-20烷基氨基，C 2-20 - 二烷基氨基，C 2-12 - 烯基氨基。 C 3-8 - 环烷基氨基，芳基氨基，二芳基氨基，芳基-C 1-8 - 烷基氨基，卤素，巯基，C 2-20 - 烯氧基，C 3-8 - 环烷氧基，芳氧基和/或C 2-8烷氧基羰基，（III）与氢气在50-250℃下反应，压力为5-350巴，在含Pd催化剂的存在下，基于催化剂的总重量计，为0.1-10重量％的Pd 在支持上。

2. 发明授权

US06525223B2 Preparation of secondary amines from nitriles 失效
标题翻译：从腈制备仲胺
公开(公告)号：US06525223B2
公开(公告)日：2003-02-25
申请号：US10026900
申请日：2001-12-27
申请人： Joachim Pfeffinger , Michael Hüllmann , Arthur Höhn , Frank Funke , Frank Ohlbach , Till Gerlach
发明人： Joachim Pfeffinger , Michael Hüllmann , Arthur Höhn , Frank Funke , Frank Ohlbach , Till Gerlach
IPC分类号： C07C20948
CPC分类号： C07C209/48 , C07C211/11
摘要： Secondary amines of the formula (II) (X—CH2—)2NH (II) where X is a C1-20-alkyl, C2-20-alkenyl or C3-8-cycloalkyl group which may be unsubstituted or substituted by C1-20-alkyl, C3-8-cycloalkyl, C4-20-alkylcycloalkyl, C4-20-cycoalkylalkyl, C2-20-alkoxyalkyl, C6-14-aryl, C7-20-alkylaryl, C7-20-aralkyl, C1-20-alkoxy, hydroxy, C1-20-hydroxyalkyl, amino, C1-20-alkylamino, C2-20-dialkylamino, C2-12-alkenylamino, C3-8-cycloalkylamino, arylamino, diarylamino, aryl-C1-8-alkylamino, halogen, mercapto, C2-20-alkenyloxy, C3-8-cycloalkoxy, aryloxy and/or C2-8-alkoxycarbonyl, are prepared by reacting nitriles of the formula (III) X—CN (III) with hydrogen at from 20 to 250° C. and pressures of from 60 to 350 bar in the presence of an Rh-containing catalyst comprising from 0.1 to 5% by weight, based on the total weight of the catalyst, of Rh on a support to give mixtures of primary amines of the formula (I) X—CH2—NH2 (I) and secondary amines of the formula (II) (X—CH2—)2NH (II) and returning at least part of the primary amines separated from the mixtures obtained to the reaction.
摘要翻译：式（II）的仲胺，其中X是可以是未取代的或被C 1-20 - 烷基，C 3-8 - 环烷基，C 4 -C 18环烷基，C 3-8 - C 20-20烷基烷基，C 2-20 - 烷氧基烷基，C 6-14 - 芳基，C 7-20 - 烷基芳基，C 7-20 - 芳烷基，C 1-20 - 烷氧基，羟基，C 1-20 - 羟基烷基，氨基， C 1-20 - 烷基氨基，C 2-20 - 二烷基氨基，C 2-12 - 烯基氨基，C 3-8 - 环烷基氨基，芳基氨基，二芳基氨基，芳基-C 1-8 - 烷基氨基，卤素，巯基，C 2-20 - 烯氧基，环烷氧基，芳氧基和/或C 2-8 - 烷氧基羰基，通过在含Rh的催化剂存在下，使式（III）的腈与20至250℃的压力和60至350巴的压力反应来制备包含基于催化剂总重量的0.1至5重量％的Rh在载体上以得到式（I）的伯胺和式（II）的仲胺的混合物，并使至少部分从获得的混合物中分离出伯胺反应。

3. 发明授权

US06723880B2 Preparation of secondary amines from primary amines 有权
标题翻译：从伯胺制备仲胺
公开(公告)号：US06723880B2
公开(公告)日：2004-04-20
申请号：US10173774
申请日：2002-06-19
申请人： Peter Neumann , Johann-Peter Melder , Christoph Benisch , Arthur Höhn , Joachim Pfeffinger
发明人： Peter Neumann , Johann-Peter Melder , Christoph Benisch , Arthur Höhn , Joachim Pfeffinger
IPC分类号： C07D41702
CPC分类号： C07C209/64 , C07C211/13
摘要： A process for producing secondary amines of the formula R1R2N—A—NH—A—NR1R2, where R1 and R2 are linear or branched C1-20-alkyl radicals, optionally substituted with from 1 to 5 phenyl groups; or cyclohexyl radicals; or together with the nitrogen atom to which they are bound, form a 3 to 7 membered saturated ring, optionally containing further hetero atoms selected from the group consisting of N, O and S, and optionally substituted with from 1 to 5 C1-2-alkyl groups. The group A is a linear or branched C2-20-alkylene group, optionally containing from 1 to 5 phenylene groups; or a radical of the formula —CH(R3)—[CH2]k—X—[CH(R3)—[CH2]k—X]m—CH(R3)—[CH2]k—, where R3 is H or CH3, X is O, S or NR4, R4 is H or a linear or branched C1-4-alkyl group, k is 1 or 2, and m is an integer from 0 to 4; or a group of the formula where n, o, p, and q are, independently, integers from 1 to 4. In this process, primary amines of the formula R1R2N—A—NH2 are reacted in the presence of hydrogen and a catalyst comprising at least one element or compound of an element of groups VIII and IB of the Periodic Table, preferably group IB, and in particular, Cu. Through this process, a high selectivity of the desired amines can be achieved.
摘要翻译：一种制备式R 1 R 2 NA-NH-A-NR 1 R 2的仲胺的方法，其中R 1和R 2是直链或支链C 1-20 - 任选被1至5个苯基取代的烷基; 或环己基; 或与其结合的氮原子一起形成3至7元饱和环，任选地含有选自N，O和S的另外的杂原子，并且任选被1至5个C 1-2 - 烷基。基团A是任选含有1至5个亚苯基的直链或支链C 2-20 - 亚烷基; 或式-CH（R 3） - [CH 2] k X- [CH（R 3） - [CH 2] k X] m -CH（R 3） - [CH 2] k - 的基团，其中R 3是H或CH 3，X是O，S或NR 4，R 4是H或直链或支链C 1-4 - 烷基，k是1或2，m是整数从0到4; 或一组式n，o，p和q独立地为1至4的整数。在该方法中，式R 1 R 2 NA-NH 2的伯胺在存在下反应氢和包含元素周期表第VIII和IB族元素的至少一种元素或化合物的催化剂，优选IB族，特别是Cu。通过该方法，可以实现所需胺的高选择性。

4. 发明授权

US06403845B1 Preparation of pentanediols from alkoxydihydropyrans 失效
标题翻译：从烷氧基二氢吡喃制备戊二醇
公开(公告)号：US06403845B1
公开(公告)日：2002-06-11
申请号：US09625487
申请日：2000-07-25
申请人： Joachim Pfeffinger , Peter Wahl , Jan Nouwen , Karsten Eller , Arthur Höhn , Jürgen Hunger
发明人： Joachim Pfeffinger , Peter Wahl , Jan Nouwen , Karsten Eller , Arthur Höhn , Jürgen Hunger
IPC分类号： C07C2700
CPC分类号： C07C29/132 , C07C29/141 , C07C31/20
摘要： are prepared by single-stage reaction of alkoxydihydropyrans of the formula (II) with water and hydrogen in the presence of a catalyst comprising oxides of nickel, zirconium and copper. In the formulae (I) and (II), R, R′, R″, R′″ can be identical or different and are each hydrogen or a linear or branched saturated hydrocarbon radical having from 1 to 20 carbon atoms in which the hydrocarbon chain may contain O, S and N as heteroatoms and which may be monosubstituted or polysubstituted by hydroxy, thiol or amino groups or halogens.
摘要翻译：在式（I）和（II）的催化剂存在下，通过式（II）的烷氧基二氢吡喃与水和氢的单步反应制备。在式（I）和（II）中，R，R' R“，R”可以相同或不同，并且各自为氢或具有1至20个碳原子的直链或支链饱和烃基，其中烃链可以含有O，S和N作为杂原子，并且其可以是被羟基，硫醇或氨基或卤素单取代或多取代。

5. 发明授权

US06689914B2 Preparation of amines 失效
标题翻译：胺的制备
公开(公告)号：US06689914B2
公开(公告)日：2004-02-10
申请号：US10234170
申请日：2002-09-05
申请人： Martin Schäfer , Arnd Böttcher , Andreas Kramer , Arthur Höhn , Shelue Liang , Frank Funke
发明人： Martin Schäfer , Arnd Böttcher , Andreas Kramer , Arthur Höhn , Shelue Liang , Frank Funke
IPC分类号： C07C2926
CPC分类号： C07C209/26
摘要： The preparation of amines of the formula (I): R1R2CH—N R3R4 (I) in which R1, R2, R3 and R4, independently of one another, are hydrogen, straight-chain or branched C1-C12-alkyl, C3-C12-cycloalkyl, C6-C10-aryl or C7-C11-aralkyl, takes place by catalytic, reductive amination of mixtures comprising carbonyl compounds of the formula (II) and/or alcohols of the formula (III) R1—C(═O)—R2 (II) R1—CH(OH)—R2 (III) which also comprise at least 50 ppm, based on the mixtures, of halogen, with nitrogen compounds of the formula (IV): H N R3 R4 (IV) with the abovementioned meanings for R1 to R4, in the presence of Co- and/or Ni-containing catalysts, which comprises carrying out the reductive amination additionally in the presence of solid acidic cocatalysts.
摘要翻译：式（I）的胺的制备：其中R 1，R 2，R 3和R 4彼此独立地是氢，直链或支链的C 1 -C 12 - 烷基，C 3 -C 12 - 环烷基，C 6 -C 10 - 芳基或C 7 -C 11 - 芳烷基，其通过催化还原胺化包括式（II）的羰基化合物和/或式（III）的醇，包含基于混合物的卤素至少50ppm与式（IV）的氮化合物：在上述对R 1至R 4的含义中，在Co-和/或Ni- 其包括另外在固体酸性助催化剂存在下进行还原胺化。

6. 发明授权

US06462236B2 Preparation of amines 有权
标题翻译：胺的制备
公开(公告)号：US06462236B2
公开(公告)日：2002-10-08
申请号：US09983307
申请日：2001-10-24
申请人： Shelue Liang , Frank Funke , Arthur Höhn
发明人： Shelue Liang , Frank Funke , Arthur Höhn
IPC分类号： C07C20926
CPC分类号： C07C209/26 , C07C211/29
摘要： Amines of the formula (I) R1R2CH—NR3R4 (I) where R1, R2, R3 and R4 are each, independently of one another, hydrogen, straight-chain or branched C1-C12-alkyl, C3-C12-cycloalkyl, C6-C10-aryl or C7-C11-aralkyl, where at least one of the radicals R1 and R2 is aryl or aralkyl whose aromatic unit is substituted by at least one halogen, are prepared by catalytic, hydrogenative amination of carbonyl compounds of the formula (II) or alcohols of the formula (III) R1—C(═O)—R2 (II) R1—CH(OH)—R2 (III) by means of nitrogen compounds of the formula (IV) HNR3R4 (IV) where R1 to R4 are as defined above, in the presence of Co- and/or Ni-containing catalysts, in the additional presence of solid acid cocatalysts and in the absence of organic sulfur compounds.
摘要翻译：式（I）的胺其中R 1，R 2，R 3和R 4各自独立地为氢，直链或支链C 1 -C 12 - 烷基，C 3 -C 12 - 环烷基，C 6 -C 10 - 芳基或C 7 -C 12 - C 11 - 芳烷基，其中基团R 1和R 2中的至少一个是其芳族单元被至少一个卤素取代的芳基或芳烷基，其通过式（II）的羰基化合物的催化，氢化胺化或式（III）通过其中R 1至R 4如上所定义的式（Ⅳ）的氮化合物在存在Co和/或Ni的催化剂的情况下，在固体酸助催化剂的另外存在下，在不存在有机硫化合物。

7. 发明授权

US06548704B2 Racemization of optically active amines 失效
公开(公告)号：US06548704B2
公开(公告)日：2003-04-15
申请号：US10012344
申请日：2001-12-12
申请人： Frank Funke , Shelue Liang , Andreas Kramer , Rainer Stürmer , Arthur Höhn
发明人： Frank Funke , Shelue Liang , Andreas Kramer , Rainer Stürmer , Arthur Höhn
IPC分类号： C07C2968
CPC分类号： C07C213/02 , B01J23/80 , B01J35/023 , B01J37/0009 , B01J37/0201 , B01J37/031 , B01J37/035 , C07B2200/07 , C07C209/68 , C07C209/88 , C07C217/08 , C07C211/07
摘要： Optically active amines of the formula I where R1 and R2 are different and R1, R2, R3 are alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl and heterocyclic radicals and R3 may also be hydrogen (H), with the radicals being able to bear substituents selected from the group consisting of alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylamino and dialkylamino, are racemized by reacting the optically active amine I in the presence of hydrogen and a hydrogenation or dehydrogenation catalyst at elevated temperature, wherein the catalyst comprises the active components copper and zinc oxide and a support material.

8. 发明授权

US06525222B2 Process for preparing amines 有权
标题翻译：制备胺的方法
公开(公告)号：US06525222B2
公开(公告)日：2003-02-25
申请号：US09729458
申请日：2000-12-05
申请人： Jan Nouwen , Arthur Höhn , Horst Neuhauser , Frank Funke , Stephan Andreas Schunk , Johann-Peter Melder , Knut Eger , Michael Hesse , Joachim Wulff-Döring
发明人： Jan Nouwen , Arthur Höhn , Horst Neuhauser , Frank Funke , Stephan Andreas Schunk , Johann-Peter Melder , Knut Eger , Michael Hesse , Joachim Wulff-Döring
IPC分类号： C07C20900
CPC分类号： C07C213/02 , C07C209/26 , C07C2601/08 , C07C2602/08 , C07C2602/10 , C07C211/35 , C07C211/42 , C07C217/58
摘要： Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30% by weight of oxygen-containing compounds of copper, calculated as CuO, 5 to 50% by weight of oxygen-containing compounds of nickel, calculated as NiO, where the molar ratio of nickel to copper is greater than 1, 5 to 50% by weight of oxygen-containing compounds of cobalt, calculated as CoO, 0 to 5% by weight of oxygen-containing compounds of molybdenum, calculated as MoO3, and 0 to 10% by weight of oxygen-containing compounds of aluminum and/or manganese, calculated as Al2O3 or MnO2.
摘要翻译：通过使升高的温度下的醛或酮与选自氨，伯和仲胺的氮化合物和在催化剂存在下与氢气反应的醛或酮进行反应来制备胺，其中催化剂的催化活性物质含有其制备方法和用氢处理之前，按重量计22％至45％的锆的氧含量化合物，按ZrO2计算，按重量计为CuO的含氧化合物为铜，按CuO计为5〜50％按NiO计的含镍化合物的重量，其中镍与铜的摩尔比大于1.5至50重量％的以CoO计的含氧化合物的钴，0至5重量％按MoO3计算的含氧化合物的钼和0至10重量％的按Al2O3或MnO2计算的含铝和/或锰的含氧化合物。

9. 发明授权

US06576795B1 Racemization of optically active amines 失效
标题翻译：光学活性胺的外消旋化
公开(公告)号：US06576795B1
公开(公告)日：2003-06-10
申请号：US10261123
申请日：2002-10-01
申请人： Frank Funke , Shelue Liang , Andreas Kramer , Rainer Stürmer , Arthur Höhn
发明人： Frank Funke , Shelue Liang , Andreas Kramer , Rainer Stürmer , Arthur Höhn
IPC分类号： C07C2968
CPC分类号： C07C213/02 , B01J23/80 , B01J35/023 , B01J37/0009 , B01J37/0201 , B01J37/031 , B01J37/035 , C07B2200/07 , C07C209/68 , C07C209/88 , C07C217/08 , C07C211/07
摘要： Optically active amines of the formula I where R1 and R2 are different and R1, R2, R3 are alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl and heterocyclic radicals and R3 may also be hydrogen (H), with the radicals being able to bear substituents selected from the group consisting of alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylamino and dialkylamino, are racemized by reacting the optically active amine I in the presence of hydrogen and a hydrogenation or dehydrogenation catalyst at elevated temperature, wherein the catalyst comprises the active components copper and zinc oxide and a support material.
摘要翻译：式I的光学活性胺，其中R 1和R 2不同，R 1，R 2，R 3是烷基，环烷基，芳基烷基，芳基，杂芳基和杂环基，R 3也可以是氢（H），其中基团能够承载取代基由烷基，环烷基，烷氧基，芳氧基，氨基，烷基氨基和二烷基氨基组成的组通过使光学活性胺I在氢气和氢化或脱氢催化剂的存在下在升高的温度下反应进行外消旋化，其中催化剂包含活性组分铜和氧化锌和支撑材料。

10. 发明授权

US06563004B2 Process for preparing monoisopropylamine 失效
标题翻译：单异丙胺的制备方法
公开(公告)号：US06563004B2
公开(公告)日：2003-05-13
申请号：US09729461
申请日：2000-12-05
申请人： Jan Nouwen , Stefan Käshammer , Arthur Höhn , Frank Funke , Johann-Peter Melder , Frank Gutschoven , Philip Buskens
发明人： Jan Nouwen , Stefan Käshammer , Arthur Höhn , Frank Funke , Johann-Peter Melder , Frank Gutschoven , Philip Buskens
IPC分类号： C07C20926
CPC分类号： C07C209/26 , C07C211/06
摘要： Monoisopropylamine is prepared by reacting acetone with ammonia and with hydrogen at elevated temperature and elevated pressure in the presence of a catalyst, wherein the catalytically active mass of the catalyst comprises, after its preparation and before the treatment with hydrogen, from 20 to 90% by weight of aluminum oxide (Al2O3), zirconium dioxide (ZrO2), titanium dioxide (TiO2) and/or silicon dioxide (SiO2), from 1 to 70% by weight of oxygen-containing compounds of copper, calculated as CuO, from 1 to 70% by weight of oxygen-containing compounds of nickel, calculated as NiO, and from 1 to 70% by weight of oxygen-containing compounds of cobalt, calculated as CoO.
摘要翻译：通过使丙酮与氨和氢气在升高的温度和升高的压力下在催化剂存在下反应制备单异丙胺，其中催化活性物质在其制备之后和在用氢处理之前包含20-90％氧化铝（Al 2 O 3），二氧化锆（ZrO 2），二氧化钛（TiO 2）和/或二氧化硅（SiO 2）的重量，1至70重量％的以CuO计的氧含氧化合物，1至 70重量％的以NiO计的含氧化合物的镍和1-70重量％的以CoO计的钴的含氧化合物。

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