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Preparation method of alicyclic binary secondary amine

A technology of alicyclic diamine and cyclohexanediamine, which is applied in the fields of special chemicals and fine chemicals, can solve the problem of high reaction temperature, and achieve the effect of prolonging the operation time and being convenient to use.

Pending Publication Date: 2020-11-27
江苏湘园化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN105860053A (Nanjing Forestry University) discloses a fixed-bed method using polyether polyol, hydrogen and liquid ammonia as raw materials, using a self-made Ni / Cu / Ti catalyst at 180-260°C and a pressure of 0.5-8MPa A production method for continuously preparing low-molecular-weight secondary amino-terminated polyether, the reaction temperature is relatively high when the method is adopted

Method used

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  • Preparation method of alicyclic binary secondary amine
  • Preparation method of alicyclic binary secondary amine
  • Preparation method of alicyclic binary secondary amine

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Effect test

Embodiment 1

[0024] Embodiment 1: A kind of preparation method of alicyclic divalent secondary amine

[0025] The invention discloses a method for preparing an alicyclic secondary secondary amine with high product yield, high purity, convenient operation, environmental friendliness, non-toxicity and pollution, and low reactivity.

[0026] This secondary amino group has a substituted alkyl group on the α-position carbon of the amino group, that is, the substituent on the N atom belongs to a secondary carbon-substituted alkyl group, and the steric hindrance effect is enhanced, effectively reducing the reactivity of the secondary amino group.

[0027] The reaction formula is as follows:

[0028]

[0029] The present invention adopts the ketone compound with the total carbon number above 4 as the raw material instead of the aldehyde compound, and its advantage is that the substituted alkyl group connected to the secondary amino group in the hydrogenation target product has a greater steric ...

Embodiment 2

[0044] Embodiment 2: A kind of preparation method of alicyclic divalent secondary amine

[0045] Put 147.5g (0.7mol) of 4,4'-diaminodicyclohexylmethane, 161.5g of methyl ethyl ketone (2.24mol) and 4.5g of palladium carbon catalyst into a stainless steel high-pressure reaction vessel, close the feeding port, and replace the reaction vessel with nitrogen The air in the medium is 3 times and the nitrogen is replaced with hydrogen for 3 times. The temperature is raised to control the temperature at 60°C, and the hydrogen is continuously introduced to control the hydrogen pressure at 4.0-4.5MPa. As the reaction progresses, the temperature can be increased appropriately, and the maximum reaction temperature is controlled at 95°C. Within the range, the hydrogen pressure is not greater than 6MPa. After 25 hours of reaction, cool down to room temperature and replace the residual hydrogen with nitrogen, release the pressure and return to normal pressure, and the reaction is over. The re...

Embodiment 3

[0046] Embodiment 3: A kind of preparation method of alicyclic divalent secondary amine

[0047] Put 147.5g (0.7mol) of 4,4'-diaminodicyclohexylmethane, 260.5g of methyl isobutyl ketone (2.6mol) and 4.5g of palladium carbon catalyst into a stainless steel high-pressure reaction vessel, close the feeding port, Replace the air in the reaction vessel with nitrogen for 3 times and replace the nitrogen with hydrogen for 3 times. Increase the temperature and control the temperature to 60°C. Continue to feed hydrogen and control the pressure of hydrogen to 4.0-4.3 MPa. As the reaction progresses, the temperature can be increased appropriately. The highest reaction The temperature is controlled within 95°C, and the hydrogen pressure is not greater than 6MPa. After 25 hours of reaction, cool down to room temperature and replace the residual hydrogen with nitrogen, release the pressure and return to normal pressure, and the reaction ends. The reaction product is filtered, and the filter...

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Abstract

The invention relates to a preparation method of alicyclic binary secondary amine, which is characterized by comprising the following steps: by using alicyclic binary primary amine and ketone as raw materials, carrying out catalytic hydrogenation in the presence of a catalyst, and carrying out monoalkylation substitution on the primary amino group to obtain the alicyclic binary secondary amine, wherein R is an aliphatic alkylene group containing a cycloalkyl structure, and R'and R''each independently represent an alkyl group having 1-6 carbon atoms. According to the present invention, the low-viscosity target product containing the large substituted alkyl secondary amino group is prepared, and the alicyclic diamine can be used for polyurethane / polyurea, an epoxy resin chain extender or a curing agent.

Description

technical field [0001] The invention belongs to the technical field of special chemicals and fine chemicals, and relates to a method for preparing secondary alicyclic diamines, in particular to a method for preparing low-viscosity alicyclic dibasic secondary amines. Background technique [0002] Dibasic primary amine compounds are chain extenders or curing agents for polyurethane elastomers and epoxy resin materials, and can also be used to synthesize polyamides. Polyurethane based on elastic polyurethane materials (including castable elastomers, plastic polyurethane paving materials, polyurethane waterproof coatings, adhesives, sealants, potting adhesives, sprayed polyurethane urea and sprayed polyurea, reaction injection molding polyurethane materials) field, it is an important class of additives, among which the most commonly used aromatic dibasic amines, such as 3,3'-dichloro-4,4'-diaminodiphenylmethane (MOCA), 3,5-diethyl DETDA, trade name Ethacure 100 or E-100), 3,5-d...

Claims

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Application Information

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IPC IPC(8): C07C211/36C07C211/18C07C209/26C08G18/32
CPCC07C209/26C08G18/3234C07C2601/14C07C211/36C07C211/18
Inventor 周建刘益军王静怡
Owner 江苏湘园化工有限公司
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