Nouryon Chemicals International B.v.

Slavisa Jovic

Antoon Jacob Berend Ten Kate

Rolf Krister Edvinsson

Eike Nicolas Kantzer

Karl Fredrik Lake

Ina Ehlers

Hendrik Van Dam

Rens Veneman

Michiel Jozef Thomas Raaijmakers

Jenny Valborg Therese Adrian Meredith

Lawien Feisal Zubeir

Stig Mikael Wernersson

Lars Torbjörn Hagberg

Björn Patrik Skansen

Michael Bertil Einar Sarning

Robert Kristoffer Berg

Michael Bertil Einar Andersson-Sarning

Sara Erika Tönnerfors

Lars Torbj Rn Hagberg

The present disclosure pertains to a process for manufacturing alkyleneamine compounds, comprising the steps of wherein A is selected from the group of C2 to C4 alkylene units, optionally substituted by one or more C1 to C3 alkyl groups, with an alkylhalide compound to form an alkyleneamine hydrohalide salt comprising at least one cyclic alkyleneurea group of formula I, the alkylhalide compound being selected from the group of haloalkanes with 2-6 halogen atoms, and haloaminoalkanes, and

Process for manufacturing alkyleneamine compounds

A process is provided for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound having a linear —NH—CH—CH—NH— group. The process includes, in an absorption step, contacting a liquid medium comprising an ethyleneamine compound having a linear —NH—CH—CH—NH— group with a CO-containing gas stream at a pressure of from about 1 to about 20 bara, resulting in the formation of a liquid medium into which COhas been absorbed. The process further includes bringing the liquid medium to cyclic urea formation conditions, and, in an urea formation step, forming cyclic urea adduct of the ethyleneamine compound, urea formation conditions including a temperature of at least about 120° C., wherein the total pressure at the end of the urea formation step is at most about 20 bara, and wherein the temperature in the absorption step is lower than the temperature in the urea formation step.

Process for manufacturing a cyclic urea adduct of an ethyleneamine compound

A process for producing a cyclic alkylene urea product of Formula I:

Process for preparing cyclic alkylene ureas

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.

Process for manufacturing ethyleneamine compounds

Process for manufacturing ethyleneamine compounds selected from the group of ethyleneamines and hydroxyethylethyleneamines wherein the process comprises two reaction sequences.

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.

Process for manufacturing a mixture of straight-hain and non-straight-chain ethyleneamines

A process is provided to prepare propylene amines of the formula NH&#x2014;(A-NH&#x2014;)R, wherein R is a hydrogen atom or an alkyl group, p is at least 1 when R is an alkyl group, and at least 2 when R is a hydrogen atom, or derivatives or precursors thereof wherein one or more units &#x2014;NH-A-NH&#x2014; may be present as a cyclic urea unit  

Process to prepare propylene amines and propylene amine derivatives

A process to convert cyclic alkylene ureas into their corresponding alkylene amines is provided. An exemplary process includes reacting the cyclic alkylene ureas with an amine compound chosen from the group of primary amines or secondary amines that have a higher boiling point than the alkylene amines formed during the process, wherein the process is a reactive separation process and the reaction mixture contains less than about 10 wt % of water on the basis of total weight of the reaction mixture.

Reactive separation process to convert cyclic alkylene ureas into their corresponding alkylene amines

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 &#x2014;NH&#x2014;CH2-CH2-NH&#x2014; 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.

A process is provided for preparing ethyleneamines of the formula NH&#x2014;(CH&#x2014;NH&#x2014;)H wherein p is at least 3, or derivatives thereof wherein one or more units &#x2014;NH&#x2014;CH&#x2014;NH&#x2014; may be present as a cyclic ethylene urea unit or piperazine unit or between two units &#x2014;NH&#x2014;CH&#x2014;NH&#x2014; a carbonyl moiety is present. The process includes reacting an ethanolamine-functional compound OH&#x2014;(CH&#x2014;NH&#x2014;)H wherein q is at least 2, an amine-functional compound NH&#x2014;(CH&#x2014;NH&#x2014;)H 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.

Process to prepare ethylene amines and ethylene amine derivatives

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&#xb0; 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.

Process for converting cyclic alkylene ureas into their corresponding alkylene amines

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.

Two-step process for converting cyclic alkylene ureas into their corresponding alkylene amines

The invention pertains to a process for converting a feedstock comprising cyclic alkyleneureas into their corresponding alkyleneamines, comprising &#x2014;a CO2 removal step in which cyclic alkyleneureas are converted into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO2, &#x2014;an amine removal step wherein cyclic alkyleneureas are converted in a reactive separation process into their corresponding alkyleneamines by reaction with an amine compound selected from the group of primary amines or secondary amines which have a higher boiling point than the alkyleneamines formed during the process. It has been found that the combination of a CO2 removal step and an amine removal step makes it possible to convert alkyleneureas into the corresponding amines in an efficient manner in a high reaction rate.

Multi-step process for converting cyclic alkyleneureas into their corresponding alkyleneamines

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 COadduct of a starting compound comprising a &#x2014;NH&#x2014;CH&#x2014;CH&#x2014;NH&#x2014; moiety or a &#x2014;NH&#x2014;CH&#x2014;CH&#x2014;OH moiety, or HO&#x2014;CH&#x2014;CH&#x2014;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 COadduct, to form COadduct of a product polyethyleneamine compound, in an elimination step converting COadduct of product polyethyleneamine compound to the corresponding product polyethylene amine compound, wherein a fraction comprising a recycle compound comprising a &#x2014;NH&#x2014;CH&#x2014;CH&#x2014;NH&#x2014; moiety or a &#x2014;NH&#x2014;CH&#x2014;CH&#x2014;OH moiety, or HO&#x2014;CH&#x2014;CH&#x2014;OH, or COadducts 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 &#x2014;NH&#x2014;CH&#x2014;CH&#x2014;NH&#x2014; moieties and &#x2014;NH&#x2014;CH&#x2014;CH&#x2014;OH moieties than the product polyethyleneamine compound.

Process for preparing ethyleneamine compounds

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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Utrecht, Netherlands

Slavisa Jovic