公开(公告)号：US11591543B2

公开(公告)日：2023-02-28

申请号：US16753413

申请日：2018-10-05

Applicant: BASF SE

Inventor： Nicolas Marion ,  Rolf Pinkos ,  Stefan Ruedenauer ,  Florian Garlichs ,  Ralf Pelzer ,  Roman Dostalek ,  Joachim Pfeffinger ,  Anja Vinckier ,  Stephanie Renz ,  Christoph Stock ,  Regina-Margareta Berg ,  Miriam Bru Roig ,  Margarethe Klos

IPC: C11B9/00 ,  C07D309/04

Abstract: The present invention relates to aroma chemical compositions containing 3,5-diethyl-2-propyl-tetrahydropyran, a 3,5-diethyl-2-propyl-dihydropyran or a 3,5-diethyl-2-propyl-pyran, a mixture of such compounds, a stereoisomer of one of these compounds, or a mixture of stereoisomers of one or more of these compounds. The invention further relates to a method for preparing such compounds, stereoisomers or mixtures thereof, to the composition obtainable by this method, to the use of such compounds as an aroma chemical or for modifying the scent character of a fragranced composition; and to a method for preparing a fragranced composition or for modifying the scent character of a fragranced composition using said compounds. Moreover, the invention relates to 3,5-diethyl-2-propyl-tetrahydropyran, to its stereoisomers and to mixtures of these stereoisomers.

公开(公告)号：US09315479B2

公开(公告)日：2016-04-19

申请号：US13940964

申请日：2013-07-12

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Roman Dostalek ,  Jörg Pastre ,  Aik Meam Tan

IPC: C07D295/027

CPC classification number: C07D295/027

Abstract: Process for preparing pyrrolidine of the formula I by reacting 1,4-butanediol (BDO) of the formula II with ammonia in the presence of hydrogen and a supported, metal-containing catalyst, wherein the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and in the range from 0.2 to 5.0% by weight of oxygen-containing compounds of tin, calculated as SnO, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 160 to 220 bar, a temperature in the range from 160 to 230° C., using ammonia in a molar ratio to BDO used of from 5 to 50 and in the presence of 1.0 to 4.5% by weight of hydrogen, based on the amount of BDO used.

Abstract translation: 通过使式II的1,4-丁二醇（BDO）与氨在负载的含金属催化剂的存在下与氨反应制备式I的吡咯烷的方法，其中催化剂的催化活性物质在其 用氢还原，包括铝，铜，镍和钴的含氧化合物，并且在0.2至5.0重量％的锡的含氧化合物的锡的范围内，以SnO计算，并且反应在液相中进行 在160-240巴范围内的绝对压力下，温度在160-230℃的范围内，使用与BDO的摩尔比为5至50的氨和在1.0至4.5％的存在下，通过 基于所用BDO的量，氢的重量。

公开(公告)号：US20130331573A1

公开(公告)日：2013-12-12

申请号：US13910554

申请日：2013-06-05

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Ulrich Abel ,  Roman Dostalek ,  Nina Challand ,  Bernd Stein ,  Michael Jödecke

IPC: C07D241/04 ,  C07C213/04 ,  C07C209/28

CPC classification number: C07D241/04 ,  C07C209/28 ,  C07C213/04 ,  C07D295/023 ,  C07D295/027

Abstract: Process for preparing piperazine of the formula I by reacting diethanolamine (DEOA) of the formula II with ammonia in the presence of hydrogen and a supported, metal-containing catalyst has been found, wherein the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and in the range from 0.2 to 5.0% by weight of oxygen-containing compounds of tin, calculated as SnO, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 160 to 220 bar, a temperature in the range from 180 to 220° C., using ammonia in a molar ratio to DEOA used of from 5 to 25 and in the presence of 0.2 to 9.0% by weight of hydrogen, based on the total amount of DEOA used and ammonia.

Abstract translation: 已经发现通过使式II的二乙醇胺（DEOA）与氢气和负载的含金属的催化剂的氨反应制备式I的哌嗪的方法，其中催化剂的催化活性物质在其还原之前 与氢气一起包含铝，铜，镍和钴的含氧化合物，其含量为0.2至5.0重量％，以SnO计算的含氧化合物锡，反应在液相中进行 使用160-220巴的绝对压力，温度在180-220℃范围内，使用摩尔比为DEA的氨为5至25，在0.2至9.0重量％存在下 的氢气，基于使用的DEOA的总量和氨。

公开(公告)号：US08981093B2

公开(公告)日：2015-03-17

申请号：US13910554

申请日：2013-06-05

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Ulrich Abel ,  Roman Dostalek ,  Nina Challand ,  Bernd Stein ,  Michael Jödecke

IPC: C07D295/023 ,  C07D241/04 ,  C07C209/28 ,  C07C213/04 ,  C07D295/027

CPC classification number: C07D241/04 ,  C07C209/28 ,  C07C213/04 ,  C07D295/023 ,  C07D295/027

Abstract: Process for preparing piperazine of the formula I by reacting diethanolamine (DEOA) of the formula II with ammonia in the presence of hydrogen and a supported, metal-containing catalyst has been found, wherein the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and in the range from 0.2 to 5.0% by weight of oxygen-containing compounds of tin, calculated as SnO, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 160 to 220 bar, a temperature in the range from 180 to 220° C., using ammonia in a molar ratio to DEOA used of from 5 to 25 and in the presence of 0.2 to 9.0% by weight of hydrogen, based on the total amount of DEOA used and ammonia.

Abstract translation: 已经发现通过使式II的二乙醇胺（DEOA）与氢气和负载的含金属的催化剂的氨反应制备式I的哌嗪的方法，其中催化剂的催化活性物质在其还原之前 与氢气一起包含铝，铜，镍和钴的含氧化合物，其含量为0.2至5.0重量％，以SnO计算的含氧化合物锡，反应在液相中进行 使用160-220巴的绝对压力，温度在180-220℃范围内，使用摩尔比为DEA的氨为5至25，在0.2至9.0重量％存在下 的氢气，基于使用的DEOA的总量和氨。

公开(公告)号：US20140018547A1

公开(公告)日：2014-01-16

申请号：US13940964

申请日：2013-07-12

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Roman Dostalek ,  Jörg Pastre ,  Aik Meam Tan

IPC: C07D295/027

CPC classification number: C07D295/027

Abstract: Process for preparing pyrrolidine of the formula I by reacting 1,4-butanediol (BDO) of the formula II with ammonia in the presence of hydrogen and a supported, metal-containing catalyst, wherein the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and in the range from 0.2 to 5.0% by weight of oxygen-containing compounds of tin, calculated as SnO, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 160 to 220 bar, a temperature in the range from 160 to 230° C., using ammonia in a molar ratio to BDO used of from 5 to 50 and in the presence of 1.0 to 4.5% by weight of hydrogen, based on the amount of BDO used.

Abstract translation: 通过使式II的1,4-丁二醇（BDO）与氨在负载的含金属催化剂的存在下与氨反应制备式I的吡咯烷的方法，其中催化剂的催化活性物质在其 用氢还原，包括铝，铜，镍和钴的含氧化合物，并且在0.2至5.0重量％的锡的含氧化合物的锡的范围内，以SnO计算，并且反应在液相中进行 在160-240巴范围内的绝对压力下，温度在160-230℃的范围内，使用与BDO的摩尔比为5至50的氨和在1.0至4.5％的存在下，通过 基于所用BDO的量，氢的重量。

公开(公告)号：US20130331574A1

公开(公告)日：2013-12-12

申请号：US13910602

申请日：2013-06-05

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Ulrich Abel ,  Roman Dostalek ,  Nina Challand ,  Bernd Stein ,  Michael Jodecke

IPC: C07D295/023

CPC classification number: C07D295/023

Abstract: Process for preparing piperazine of the formula I by reacting diethanolamine (DEOA) of the formula II with ammonia (NH3) in the presence of hydrogen and a supported, metal-containing catalyst, wherein the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises 20 to 85% 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, 14 to 70% by weight of oxygen-containing compounds of nickel, calculated as NiO, and 0 to 5% by weight of oxygen-containing compounds of molybdenum, calculated as MoO3, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 160 to 220 bar, a temperature in the range from 180 to 220° C., using ammonia in a molar ratio to DEOA used of from 5 to 20 and in the presence of 0.2 to 9.0% by weight of hydrogen, based on the total amount of DEOA used and ammonia.

Abstract translation: 通过使式II的二乙醇胺（DEOA）与氢气和负载的含金属催化剂的存在下的氨（NH 3）反应制备式I的哌嗪的方法，其中催化剂的催化活性物质在其还原之前 含氢量为20〜85重量％，以ZrO 2计，含氧化合物的锆为1〜30重量％，以CuO表示的含氧化合物的铜为14〜70重量％ 以NiO计算的镍化合物和以重量计为MoO 3的0-5％重量的含氧化合物的钼，反应在液相中以160-220巴的绝对压力进行， 温度在180-220℃的范围内，使用的摩尔比为使用的DEOA为5至20的氨和在0.2至9.0重量％的氢气存在下，基于所用的DEOA的总量和 氨。

公开(公告)号：US08927712B2

公开(公告)日：2015-01-06

申请号：US13906931

申请日：2013-05-31

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Ulrich Abel ,  Roman Dostalek ,  Bernd Stein

IPC: C07D241/04 ,  C07D295/00 ,  C07D295/088 ,  B01J23/83 ,  B01J35/02 ,  B01J37/00 ,  B01J37/03 ,  C07D295/03 ,  B01J37/08 ,  B01J37/18

CPC classification number: C07D295/088 ,  B01J23/83 ,  B01J35/023 ,  B01J37/0009 ,  B01J37/031 ,  B01J37/08 ,  B01J37/18 ,  B01J2523/00 ,  C07D295/03 ,  B01J2523/17 ,  B01J2523/31 ,  B01J2523/3706

Abstract: Process for the preparation of a mono-N-alkylpiperazine of the formula I in which R1 is C1- to C5-alkyl or 2-(2-hydroxyethoxy)ethyl, by reacting diethanolamine (DEOA) of the formula II with a primary amine of the formula H2N—R1 (III) in the presence of hydrogen and a catalyst molding, where the reaction is carried out in the liquid phase at an absolute pressure in the range from 150 to 250 bar and the amination is carried out by means of a catalyst molding, the precursor of which can be prepared according to a process in which (i) an oxidic material comprising copper oxide, aluminum oxide and lanthanum oxide is provided, (ii) pulverulent metallic copper and/or copper flakes and optionally graphite is added to the oxidic material, (iii) the mixture resulting from step ii is shaped to give a molding, where the oxidic material is obtainable by simultaneous or successive precipitation of the component copper oxide, of the component aluminum oxide and of the component lanthanum oxide and subsequent drying and calcination and, after the shaping according to step iii, the catalyst molding is calcined again.

Abstract translation: 通过使式II的二乙醇胺（DEOA）与式Ⅰ的伯胺反应制备其中R 1为C 1 -C 5 - 烷基或2-（2-羟基乙氧基）乙基的式I的单-N-烷基哌嗪的方法 在氢气和催化剂模塑的存在下，式H2N-R1（III），其中反应在150-250巴的绝对压力下在液相中进行，并且胺化通过 催化剂成型，其前体可以根据其中（i）包含氧化铜，氧化铝和氧化镧的氧化物质的方法制备，（ii）加入粉末状金属铜和/或铜片以及任选的石墨 （iii）由步骤ii得到的混合物成型为得到模制品，其中氧化物质可通过组分氧化铜，组分氧化铝和组分氧化镧同时或连续沉淀获得，以及 随后的干燥和煅烧，并且根据步骤iii的成型后，再次煅烧催化剂成型。

公开(公告)号：US08884015B2

公开(公告)日：2014-11-11

申请号：US13906960

申请日：2013-05-31

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Ulrich Abel ,  Roman Dostalek ,  Bernd Stein

IPC: C07D241/04 ,  C07D295/00 ,  C07D295/088 ,  C07D295/03 ,  B01J23/835

CPC classification number: C07D295/088 ,  B01J23/835 ,  C07D295/03

Abstract: Process for the preparation of a mono-N-alkylpiperazine of the formula I in which R1 is C1- to C5-alkyl or 2-(2-hydroxyethoxy)ethyl, by reacting diethanolamine (DEOA) of the formula II with a primary amine of the formula H2N—R1 (III) in the presence of hydrogen and a supported, metal-containing catalyst, where the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and, in the range from 0.2 to 5.0% by weight, oxygen-containing compounds of tin, calculated as SnO, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 95 to 145 bar.

Abstract translation: 通过使式II的二乙醇胺（DEOA）与式Ⅰ的伯胺反应制备其中R 1为C 1 -C 5 - 烷基或2-（2-羟基乙氧基）乙基的式I的单-N-烷基哌嗪的方法 在氢气和负载的含金属催化剂存在下，式H2N-R1（III），其中催化剂的催化活性物质在用氢还原之前包含含铝的铝，铜，镍和 钴，并且在0.2至5.0重量％的范围内，以SnO计算的含锡化合物的锡和反应在液相中以95至145巴的绝对压力进行。

公开(公告)号：US20130324732A1

公开(公告)日：2013-12-05

申请号：US13906960

申请日：2013-05-31

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Ulrich Abel ,  Roman Dostalek ,  Bernd Stein

IPC: C07D295/088 ,  B01J23/835 ,  C07D295/03

CPC classification number: C07D295/088 ,  B01J23/835 ,  C07D295/03

Abstract: Process for the preparation of a mono-N-alkylpiperazine of the formula I in which R1 is C1- to C5-alkyl or 2-(2-hydroxyethoxy)ethyl, by reacting diethanolamine (DEOA) of the formula II with a primary amine of the formula H2N—R1 (III) in the presence of hydrogen and a supported, metal-containing catalyst, where the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and, in the range from 0.2 to 5.0% by weight, oxygen-containing compounds of tin, calculated as SnO, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 95 to 145 bar.

Abstract translation: 通过使式II的二乙醇胺（DEOA）与式Ⅰ的伯胺反应制备其中R 1为C 1 -C 5 - 烷基或2-（2-羟基乙氧基）乙基的式I的单-N-烷基哌嗪的方法 在氢气和负载的含金属催化剂存在下，式H2N-R1（III），其中催化剂的催化活性物质在用氢还原之前包含含铝的铝，铜，镍和 钴，并且在0.2至5.0重量％的范围内，以SnO计算的含锡化合物的锡和反应在液相中以95至145巴的绝对压力进行。

公开(公告)号：US20130324731A1

公开(公告)日：2013-12-05

申请号：US13906931

申请日：2013-05-31

Applicant: BASF SE

Inventor： Roland Bou Chedid ,  Johann-Peter Melder ,  Ulrich Abel ,  Roman Dostalek ,  Bernd Stein

IPC: C07D295/088 ,  C07D295/03 ,  B01J23/83

CPC classification number: C07D295/088 ,  B01J23/83 ,  B01J35/023 ,  B01J37/0009 ,  B01J37/031 ,  B01J37/08 ,  B01J37/18 ,  B01J2523/00 ,  C07D295/03 ,  B01J2523/17 ,  B01J2523/31 ,  B01J2523/3706

Abstract: Process for the preparation of a mono-N-alkylpiperazine of the formula I in which R1 is C1- to C5-alkyl or 2-(2-hydroxyethoxy)ethyl, by reacting diethanolamine (DEOA) of the formula II with a primary amine of the formula H2N—R1 (III) in the presence of hydrogen and a catalyst molding, where the reaction is carried out in the liquid phase at an absolute pressure in the range from 150 to 250 bar and the amination is carried out by means of a catalyst molding, the precursor of which can be prepared according to a process in which (i) an oxidic material comprising copper oxide, aluminum oxide and lanthanum oxide is provided, (ii) pulverulent metallic copper and/or copper flakes and optionally graphite is added to the oxidic material, (iii) the mixture resulting from step ii is shaped to give a molding, where the oxidic material is obtainable by simultaneous or successive precipitation of the component copper oxide, of the component aluminum oxide and of the component lanthanum oxide and subsequent drying and calcination and, after the shaping according to step iii, the catalyst molding is calcined again.

Abstract translation: 通过使式II的二乙醇胺（DEOA）与式Ⅰ的伯胺反应制备其中R 1为C 1 -C 5 - 烷基或2-（2-羟基乙氧基）乙基的式I的单-N-烷基哌嗪的方法 在氢气和催化剂模塑的存在下，式H2N-R1（III），其中反应在150-250巴的绝对压力下在液相中进行，并且胺化通过 催化剂成型，其前体可以根据其中（i）包含氧化铜，氧化铝和氧化镧的氧化物质的方法制备，（ii）加入粉末状金属铜和/或铜片以及任选的石墨 （iii）由步骤ii得到的混合物成型为得到模制品，其中氧化材料可通过组分氧化铜，组分氧化铝和组分氧化镧同时或连续沉淀获得，以及 苏 随后干燥和煅烧，并且在根据步骤iii成形之后，再次煅烧催化剂成型。