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Preparation of secondary amines

A kind of secondary amine, primary amine technology, applied in the catalysis field of amine alkylation, can solve problems such as low amine conversion rate

Inactive Publication Date: 2010-06-30
HUNTSMAN PETROCHEMICAL LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When utilizing base metal catalysts (Ni, Co, etc.), higher acetone / amine ratios are required, but only low conversions to amines are observed even under the above conditions

Method used

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  • Preparation of secondary amines
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 - Preparation of N-isopropyl-N', N'-dimethyl-1,3-propanediamine

[0040] 580 g / h of dimethylaminopropylamine (“DMAPA”) and 420 g / h of acetone were simultaneously fed to a jacketed stainless steel tubular upflow reactor (volume 600 cc) with an internal diameter of 1.338″ and equipped with a thermowell (upstream), wherein said thermowell extends upwards into the reactor, made of a pipe of 0.25 O.D. The packed bed of nickel catalyst disclosed in US3151112 and US3654370 is housed in the reactor tube. The add-on ratio of hydrogen is chemical The metered excess was about 100%. The reaction was carried out at a pressure of 1500 psig and a temperature of 135°C. After a single pass through a tubular reactor about 30" long, analysis of the reactor effluent showed about 85% N-iso Propyl-N',N'-dimethyl-1,3-propanediamine, 6% unreacted DMAPA, 1% diisopropylDMAPA and 2% coupled product. Furthermore, diisopropylDMAPA cannot be separated from DMAPA during the subsequent di...

Embodiment 2

[0041] Example 2 - Preparation of N-isopropyl-N', N'-dimethyl-1,3-propanediamine

[0042] The procedure of Example 1 was repeated, except that the previously used nickel catalyst was replaced by a 1% palladium catalyst supported on carbon (Engelhard), and the reaction temperature was lowered to 120°C. Analysis of the effluent showed an approximately 97% yield of N-isopropyl-N',N'-dimethyl-1,3-propanediamine, with no significant diisopropylDMAPA or coupling products detected. Distillation of the effluent yielded 99.5% pure N-isopropyl-N',N'-dimethyl-1,3-propanediamine.

Embodiment 3

[0043] Example 3 - Preparation of N, N'-diisopropylisophoronediamine

[0044] About 300 g / h of isophoronediamine and 450 g / h of acetone were fed upflow into a 600 cc packed bed reactor charged with nickel catalyst as described in Example 1 above. About 100% excess hydrogen was added. Reactions were run at 2000 psig and 140°C. The reactor effluent was stripped of light components under reduced pressure. The resulting product was analyzed to contain 8.78 meq / g total amines and 3.557 meq / g primary amines. The above results indicated that a significant amount (40.5%) of the primary amine groups remained unalkylated. In addition, GC analysis indicated the presence of about 2.00% "heavy components". That is to say, coupling of amines takes place.

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PUM

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Abstract

Disclosed herein is a process for the reductive alkylation of primary amines to form secondary amines, by high pressure reaction of the primary amine with an alkylating agent and hydrogen in the presence of a catalyst which comprises metallic palladium. A process of the present invention is characterized in having high conversion rates and high selectivities, both greater than 95% on a first passthrough the reactor. According to a preferred embodiment, the secondary amine produced comprises at least one 2-alkyl group bonded to the nitrogen atom of the primary amine product.

Description

[0001] This application is a divisional application, the application number of its parent application is 03817376.X, the filing date is July 21, 2003, and the invention title is "Preparation of Secondary Amine". technical field [0002] This invention relates generally to a catalytic process for the alkylation of amines, and more particularly to the selective formation of secondary amines from primary amines. The process according to one embodiment of the invention is particularly suitable for preparing 2-alkyl-substituted amines from primary amines. Background technique [0003] Methods for preparing organic amines are already known in the prior art. For example US3994975 relates to the reductive amination of unsaturated cyclic ketones, the cyclic amines thus prepared and their use. For example, when isophorone is reductively aminated, trimethylcyclohexylamine and cyclohexenamine are obtained. The invention includes the use of the amine products as fuel additives for stab...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/36C07C209/26B01J23/44C07B61/00C07C211/09C07C211/11C07C211/18C07C213/02C07C217/50
CPCC07C209/26C07C2101/14C07C2601/14C07C211/11C07C211/36C07C209/90
Inventor 苏维扬C·H·内利
Owner HUNTSMAN PETROCHEMICAL LLC