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公开(公告)号:US11072686B2
公开(公告)日:2021-07-27
申请号:US16638397
申请日:2018-08-07
发明人: Rens Veneman , Antoon Jacob Berend Ten Kate , Michiel Jozef Thomas Raaijmakers , Slavisa Jovic , Rolf Krister Edvinsson , Eike Nicolas Kantzer , Karl Fredrik Lake , Ina Ehlers , Hendrik Van Dam
IPC分类号: C07C209/68 , C08G73/02 , C07C213/08
摘要: An integrated process for manufacturing polyethyleneamine compounds selected from the group of polyethyleneamines and hydroxyethylethyleneamines is provided. The process includes in an adduction step, providing a CO2 adduct of a starting compound comprising a —NH—CH2—CH2—NH— moiety or a —NH—CH2—CH2—OH moiety, or HO—CH2—CH2—OH, in a reaction step reacting a hydroxy-functional compound selected from the group of ethanolamines and dihydroxyethane with an amine-functional compound, wherein at least part of the total of hydroxy-functional compounds and amine-functional compounds is provided in the form of a CO2 adduct, to form CO2 adduct of a product polyethyleneamine compound, in an elimination step converting CO2 adduct of product polyethyleneamine compound to the corresponding product polyethylene amine compound, wherein a fraction comprising a recycle compound comprising a —NH—CH2—CH2—NH— moiety or a —NH—CH2—CH2—OH moiety, or HO—CH2—CH2—OH, or CO2 adducts thereof, is provided from the end of the reaction step or the elimination step to the adduction step or to the reaction step, wherein the recycle compound has per molecule on average fewer of the total of —NH—CH2—CH2—NH— moieties and —NH—CH2—CH2—OH moieties than the product polyethyleneamine compound.
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公开(公告)号:US10995058B2
公开(公告)日:2021-05-04
申请号:US16468496
申请日:2017-12-12
发明人: Eike Nicolas Kantzer , Karl Fredrik Lake , Antoon Jacob Berend Ten Kate , Michiel Jozef Thomas Raaijmakers , Rens Veneman , Ina Ehlers , Michael Bertil Einar Sarning , Hendrik Van Dam , Rolf Krister Edvinsson
IPC分类号: C07C213/08
摘要: A process for preparing hydroxyethyl ethylene amines and/or ethylene urea derivatives thereof includes reacting monoethylene glycol with an amine-functional compound having at least two —NH— units, of which at least one is selected from the group of primary amine groups and cyclic secondary amine groups, in the presence of a carbon oxide-delivering agent. The amine-functional compound includes at least one —NH—CH2-CH2-NH— unit, wherein one or more —NH—CH2-CH2-NH— units in the amine-functional compound may be present in the form of piperazine moieties or ethylene urea moieties. The molar ratio of amine-functional compound to monoethylene glycol is in the range of 0.2:1 to 1.5:1 and the molar ratio of carbon oxide-delivering agent to —NH—CH2-CH2-NH— units in the amine-functional compound is at least 0.5:1. The process allows the conversion of monoethylene glycol into ethanol amines in the absence of metals-containing catalysts and without using ammonia.
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公开(公告)号:US11884609B2
公开(公告)日:2024-01-30
申请号:US17310607
申请日:2020-02-13
发明人: Rolf Krister Edvinsson , Antoon Jacob Berend Ten Kate , Michiel Jozef Thomas Raaijmakers , Rens Veneman , Slavisa Jovic , Lawien Feisal Zubeir , Eike Nicolas Kantzer , Ina Ehlers , Hendrik Van Dam , Karl Fredrik Lake
IPC分类号: C07C213/08 , C07C209/08 , C07C209/68
CPC分类号: C07C213/08 , C07C209/08 , C07C209/68
摘要: The present disclosure pertains to a process for manufacturing ethyleneamine compounds selected from the group of ethyleneamines and hydroxyethylethyleneamines wherein the process comprises two reaction sequences.
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公开(公告)号:US11247963B2
公开(公告)日:2022-02-15
申请号:US16638351
申请日:2018-08-07
发明人: Antoon Jacob Berend Ten Kate , Rens Veneman , Hendrik Van Dam , Rolf Krister Edvinsson , Michiel Jozef Thomas Raaijmakers , Eike Nicolas Kantzer , Ina Ehlers , Slavisa Jovic , Karl Fredrik Lake , Stig Mikael Wernersson
IPC分类号: C07C209/78
摘要: A process is provided for converting one or more cyclic ethylene ureas into corresponding ethylene amines and carbon dioxide. The process may include contacting water with one or more cyclic alkylene urea compounds comprising one or more cyclic alkylene urea moieties in a reaction vessel at a temperature of 150 to 400° C., optionally in the presence of an amine compound selected from the group of primary amines, cyclic secondary amines and bicyclic tertiary amines. The mole ratio of water to cyclic alkylene urea moieties is in the range of from about 0.1 to about 20. In the reaction, at least a portion of the cyclic alkylene urea moieties are converted to corresponding alkylenediamine moieties and carbon dioxide. The process may further include removing the carbon dioxide from the liquid reaction mixture in a stripping vessel by feeding a stripping fluid to the stripping vessel. Further, the process may include removing a carbon dioxide-containing stripping fluid.
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5.
公开(公告)号:US11584721B2
公开(公告)日:2023-02-21
申请号:US16630287
申请日:2018-07-03
发明人: Hendrik Van Dam , Karl Fredrik Lake , Eike Nicolas Kantzer , Antoon Jacob Berend Ten Kate , Rolf Krister Edvinsson , Michiel Jozef Thomas Raaijmakers , Rens Veneman , Ina Ehlers , Jenny Valborg Therese Adrian Meredith , Slavisa Jovic
IPC分类号: C07D233/02 , C07C209/70 , C07C209/16
摘要: A process for manufacturing a mixture of straight-chain higher ethyleneamines and non-straight-chain higher ethyleneamines selected from branched higher ethyleneamines and cyclic higher ethyleneamines, or the urea derivatives thereof, includes reacting an amine-functional compound with an ethanolamine-functional compound in the presence of a carbon oxide delivering agent, wherein a) an amine-functional compound comprises a combination of straight-chain amine-functional compound and non-straight-chain amine-functional compound and is reacted with straight-chain ethanolamine-functional compound, or b) a straight-chain amine-functional compound is reacted with ethanolamine-functional compound comprising a combination of straight-chain ethanolamine-functional compound and non-straight-chain ethanolamine-functional compound, or c) an amine-functional compound comprising a combination of straight-chain amine-functional compound and non-straight-chain amine-functional compound is reacted with ethanolamine-functional compound comprising a combination of straight-chain ethanolamine-functional compound and non-straight-chain ethanolamine-functional compound.
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公开(公告)号:US11292769B2
公开(公告)日:2022-04-05
申请号:US16615758
申请日:2018-05-18
发明人: Karl Fredrik Lake , Eike Nicolas Kantzer , Rolf Krister Edvinsson , Ina Ehlers , Hendrik Van Dam , Jenny Valborg Therese Adrian Meredith , Lars Torbjörn Hagberg , Antoon Jacob Berend Ten Kate , Rens Veneman , Michiel Jozef Thomas Raaijmakers , Slavisa Jovic
IPC分类号: C07D233/34
摘要: Methods are provided for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound being selected from the group of ethyleneamines and hydroxyethylethyleneamines and comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethyleneamine compound is reacted with CO2 in the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1. It has been found that the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof leads to a substantial increase of the reaction rate as compared to a process wherein the auxiliary compound is not present.
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7.
公开(公告)号:US11242310B2
公开(公告)日:2022-02-08
申请号:US16638395
申请日:2018-08-07
发明人: Eike Nicolas Kantzer , Karl Fredrik Lake , Ina Ehlers , Stig Mikael Wernersson , Rolf Krister Edvinsson , Hendrik Van Dam , Antoon Jacob Berend Ten Kate , Rens Veneman , Michiel Jozef Thomas Raaijmakers , Slavisa Jovic
IPC分类号: C07C209/62
摘要: A process is provided for converting cyclic alkyleneureas into their corresponding alkyleneamines. The process includes, in a first step, converting cyclic alkyleneureas into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO2, so as to convert from about 5 mole % to about 95 mole % of alkyleneurea moieties in the feedstock to the corresponding amines. The process further includes, in a second step, adding an inorganic base and reacting cyclic alkylene ureas remaining from the first step with the inorganic base to convert them partially or completely into their corresponding alkyleneamines. Certain embodiments of the two-step process obtain a high conversion of cyclic alkyleneureas, while using substantially less strong inorganic base. Certain embodiments of the process process also show a higher selectivity to amines than prior art processes.
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公开(公告)号:US10968164B2
公开(公告)日:2021-04-06
申请号:US16638345
申请日:2018-08-07
发明人: Michiel Jozef Thomas Raaijmakers , Antoon Jacob Berend Ten Kate , Eike Nicolas Kantzer , Rens Veneman , Slavisa Jovic , Rolf Krister Edvinsson , Karl Fredrik Lake , Hendrik Van Dam , Ina Ehlers , Sara Erika Tönnerfors
IPC分类号: C07C209/62 , C07C209/86
摘要: A process to convert the cyclic monourea of ethylene amine compounds (U-EA) into ethylene amine compound (EA) is provided. The process may include performing a reactive separation step using a reaction mixture containing the cyclic monourea, wherein one cyclic monourea (U-EA) reacts with another cyclic monourea (U-EA) to transfer its urea unit thereto. The process may further include separating the obtained ethylene amine compound (EA) without urea unit from the reaction mixture.
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公开(公告)号:US11267792B2
公开(公告)日:2022-03-08
申请号:US16630291
申请日:2018-07-03
发明人: Michiel Jozef Thomas Raaijmakers , Antoon Jacob Berend Ten Kate , Rens Veneman , Karl Fredrik Lake , Slavisa Jovic , Eike Nicolas Kantzer , Ina Ehlers , Rolf Krister Edvinsson , Björn Patrik Skansen , Michael Bertil Einar Sarning , Jenny Valborg Therese Adrian Meredith , Hendrik Van Dam
IPC分类号: C07D241/04 , C07C213/08 , C07D233/34 , C07D263/22 , C07D413/06 , C07D233/36
摘要: A process is provided for preparing ethyleneamines of the formula NH2—(C2H4—NH—)pH wherein p is at least 3, or derivatives thereof wherein one or more units —NH—C2H4—NH— may be present as a cyclic ethylene urea unit or piperazine unit or between two units —NH—C2H4—NH— a carbonyl moiety is present. The process includes reacting an ethanolamine-functional compound OH—(C2H4—NH—)qH wherein q is at least 2, an amine-functional compound NH2—(C2H4—NH—)rH wherein r is at least 1, in the presence of a carbon oxide delivering agent, wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is from about 0.05:1 to about 0.7:1 and the molar ratio of carbon oxide delivering agent to amine-functional compound is higher than the molar ratio of ethanolamine-functional compound to amine-functional compound, provided that the process does not comprise reacting 3 moles of ethylenediamine (EDA) and 1 mole of AEEA (aminoethylethanolamine) in the presence of 1.65 moles of urea at 280 deg C. for 2 hours.
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公开(公告)号:US10800731B2
公开(公告)日:2020-10-13
申请号:US16630293
申请日:2018-07-03
发明人: Rens Veneman , Antoon Jacob Berend Ten Kate , Michiel Jozef Thomas Raaijmakers , Eike Nicolas Kantzer , Rolf Krister Edvinsson , Karl Fredrik Lake , Ina Ehlers , Slavisa Jovic , Hendrik Van Dam , Lars Torbjörn Hagberg
IPC分类号: C07C209/00 , C07C211/00 , C07C209/16 , C07D263/20 , C07D233/36 , C07C211/14
摘要: A process is provided for preparing ethylene amines of the formula NH2—(C2H4—NH—)pH wherein p is at least 2, or derivatives thereof wherein one or more units —NH—C2H4—NH— are present as a cyclic ethylene urea unit The process includes reacting an ethanolamine-functional compound OH—(C2H4—NH—)qH or HO—(C2H4—NH)q—C2H4—OH wherein q is at least 1, and an amine-functional compound NH2—(C2H4—NH—)rH wherein r is at least 1, in the presence of a carbon oxide delivering agent and water, with a molar ratio of water:carbon oxide delivering agent of from about 0.01:1 to about 2:1.
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