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Process for preparing cyclic alkylene ureas

A cyclic alkylene urea, alkyl technology, applied in the field of preparing cyclic alkylene urea, can solve problems such as low yield of alkylene amines

Pending Publication Date: 2020-04-10
诺力昂化学品国际有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Low yields of alkyleneamines obtained by treating the reaction mixture with KOH

Method used

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  • Process for preparing cyclic alkylene ureas
  • Process for preparing cyclic alkylene ureas
  • Process for preparing cyclic alkylene ureas

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] 2-Imidazolidinone (1.5 g, 17.42 mmol), ethylenediamine (477 mg, 7.94 mmol) and 2-aminoethanol (243 mg, 3.98 mmol) were added to a 5 ml vial. Cap the vial and fill with N 2 Purge, then heat (within 2 minutes) to 250°C. After 90 minutes the vial was cooled to room temperature and 2-aminoethanol (243 mg, 3.98 mmol) was added. Cap the vial again and fill with N 2 Purge, heat back to 250°C for an additional 120 minutes, then cool to room temperature. 2-Aminoethanol (243 mg, 3.98 mmol) was added to the reaction mixture for the third time. Cover and use N 2 After purging, the reaction mixture was heated to 250° C. for an additional 90 minutes, then cooled to room temperature. The resulting reaction mixture was analyzed by GC-FID. The results are shown in Table 1.

Embodiment 2

[0092] According to the procedure of Example 1, except that ethylenediamine (1.38g, 22.96mmol), 2-imidazolidinone (515mg, 5.98mmol) and 2-oxazolidinone (400mg, 4.59mmol) were first added to the vial , and additional charges of 2-oxazolidinone (400 mg, 4.59 mmol) were added at 90 min and 210 min. The reaction mixture was analyzed by GC-FID before each additional addition of 2-oxazolidinone and at the end of the reaction. The results are shown in Tables 1 and 2.

Embodiment 3

[0093] Embodiment 3 (comparison)

[0094] To a 5 mL microwave vial equipped with a magnetic stir bar was added ethylenediamine (1.38 g, 22.96 mmol), 2-imidazolidinone (515 mg, 5.74 mmol) and 2-oxazolidinone (1.2 g, 13.78 mmol). Cap the vial and fill with N 2 Purge and heat to 250°C over a 2 minute period using a Biotage Initiator+ Microwave Reactor. After 330 minutes the reactor was cooled back to room temperature and the contents were analyzed by GC-FID. The results are shown in Table 1.

[0095] Table 1 - Examples 1 and 2 and Comparative Example 3

[0096]

[0097]

[0098] 1 CO=EU+CMEA. Amine = EU + EDA. Based on the total amount of material added to the reaction zone

[0099] 2 (U)DETA = sum of DETA and UDETA

[0100] 3 (U)TETA = sum of TETA, U1TETA, U2TETA and DUTETA

[0101] 4 The molar ratio of the initial dose of MEA or CMEA to the combined amount of EU and EDA

[0102] Periodic portion addition of the same amount of MEA or CMEA improves the amount o...

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Abstract

A process for producing a cyclic alkylene urea product of Formula I: in which a compound of Formula II and / or Formula III is contacted in a reaction zone with a compound of Formula IV and / or Formula Vand in the presence of one or more carbonyl delivering compounds; in which; R1 is -[A-X-]qR3; R2 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from -OH and -NH2; R3 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from -OH and -NH2; A is on each occurrence independently selected from C1 to C3 alkylene units, optionally substituted by one or more C1 to C3 alkyl groups; X is on each occurrence independently selected from -O-, -NR2-, groups of Formula VI, and groups of Formula VII and p and q are each independently selected from a whole number in the range of from 0 to 8; wherein the compound of Formula II and / or the compound of Formula III are added to a reaction zone comprising compound of Formula IV and / or compound of Formula (V) continuously or semi-continuously over a period of time, or in two or more batches, wherein Formula III is R<1>NH-A-OH and Formula V is H2N-A-NR<2>-[A-X-]pR<3> (shown in the description).

Description

technical field [0001] The present invention relates to a method for preparing cyclic alkylene urea, especially a method for controlling the production of cyclic alkylene urea and alkylene alcohol substituted urea which can be used to produce various alkylene amines. Background technique [0002] Aqueous solutions of alkyleneamines and alkanolamines are commonly used for reversible CO 2 absorption process. Upon absorption, a series of compounds are formed such as carbonates, bicarbonates, carbamates and alkylene ureas. The desired product is readily desorbed CO upon heating 2 of those. Cyclic carbamates and ureas are generally considered undesirable due to their high stability. [0003] US 4 650 906 and JP 60126248 disclose the decarboxylation of ethyleneamine carbonate by heat treatment and distillation. Disclosed examples of carbonates are diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA) and piperazine...

Claims

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Application Information

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IPC IPC(8): C07D233/34
CPCC07D233/34
Inventor A·J·B·坦恩凯特K·F·莱克M·J·T·拉吉马克斯R·K·埃德温松J·V·T·阿德里安梅雷迪斯R·维尼曼H·范达E·N·坎茨尔I·埃勒斯S·约维奇
Owner 诺力昂化学品国际有限公司
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