Preparation method of hexamethylenediamine piperidine

A technology of hexamethylenediamine piperidine and sevbase, which is applied in the field of compound preparation, can solve problems such as difficulty in realizing industrialized production, difficulty in synthesis and separation, and increase in production cost, and achieves simple and convenient post-processing method, cost reduction, and equipment reduction. The effect of stress

Inactive Publication Date: 2015-05-06
JIANGSU FEIXIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

US4326063 discloses the preparation method of N,N'-dialkylamine, which is realized under the pressure condition of at least 1500psi (about 10.3MPa) with methanol as the solvent. Under such high pressure, a large amount of by-products are produced
[0007] US4605743 discloses the synthesis of hexamethylenediamine piperidine: under low pressure conditions (100~200psi), carry out with alcohol and / or water mixed solvent, but use expensive Pt, Pd as catalyst, increase production cost
US4415688 discloses the synthesis of this type of compound: it is carried out under low pressure conditions (100~200psi), but the synthesis and separation are relatively difficult, and compared with CN1346825A, etc., the yield is low, there is no obvious advantage, and it is difficult to realize industrial production

Method used

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  • Preparation method of hexamethylenediamine piperidine
  • Preparation method of hexamethylenediamine piperidine
  • Preparation method of hexamethylenediamine piperidine

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 5.7kg (49mol) of 1,6-hexanediamine and 16kg (103mol) of tetramethylpiperidone into a 100L glass reactor with 24kg of toluene, stir, vacuumize -0.070~-0.095MPa, heat up, and reflux for dehydration reaction Until no water comes out, the amount of dehydration water is measured during the reaction process.

[0026] Add the above-mentioned Schiff base solution and the skeleton nickel catalyst into the hydrogenation reactor, replace with nitrogen three times, replace with hydrogen three times, and replenish hydrogen to 1.0 MPa. After the replacement is completed, stir and heat up. When the temperature rises to 70-75°C, the reaction starts, and the hydrogen pressure is maintained at 1.0-1.5 MPa. After 5 hours, the hydrogen absorption rate becomes very slow. Turn on the heating device and control the temperature in the kettle to maintain at 85-1.5 MPa. React at 90°C for 1 hour, take samples midway, and control in GC analysis, the GC of the raw material is 0.8%, and the prod...

Embodiment 2

[0028] Dissolve 9.5kg (81.9mol) of 1,6-hexanediamine and 26.7kg (172mol) of tetramethylpiperidone in 40kg of cyclohexane to make a solution, add it to a 200L reactor, stir, and vacuum -0.070 ~-0.095MPa, heat up, reflux dehydration reaction until no water comes out, measure the amount of dehydration water during the reaction process.

[0029] Add the above-mentioned Schiff base solution and the skeleton nickel catalyst into the hydrogenation reactor, replace with nitrogen three times, replace with hydrogen three times, and replenish hydrogen to 1.0 MPa. After the replacement is completed, stir and heat up. When the temperature rises to 70-75°C, the reaction starts, and the hydrogen pressure is maintained at 1.0-1.5 MPa. After 5 hours, the hydrogen absorption rate becomes very slow. Turn on the heating device and control the temperature in the kettle to maintain at 70-1.5 MPa. React at 80°C for 1 hour, take samples midway, and control in GC analysis. The GC of the raw material i...

Embodiment 3

[0031] Add 28.50kg (245mol) of 1,6-hexanediamine and 81.83kg (526.73mol) of tetramethylpiperidone into a 500L reactor with 120kg of xylene, stir, vacuumize -0.070~-0.095MPa, heat up, and reflux The dehydration reaction is performed until no water comes out, and the amount of dehydration water is measured during the reaction process.

[0032] Add the above-mentioned Schiff base solution and the skeleton nickel catalyst into the hydrogenation reactor, replace with nitrogen three times, replace with hydrogen three times, and replenish hydrogen to 2.0 MPa. After the replacement is completed, stir and heat up. When the temperature rises to 70-75°C, the reaction starts, and the hydrogen pressure is maintained at 2.0-3.0 MPa. After 7 hours, the hydrogen absorption rate becomes very slow. Turn on the heating device and control the temperature in the kettle to maintain at 85-3.0 MPa. React at 90°C for 1 hour, take samples midway, and control in GC analysis. The GC of the raw material i...

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Abstract

The invention discloses a preparation method of N,N-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,6-hexamethylenediamine (called hexamethylenediamine piperidine for short). The preparation method comprises the following steps: 1) carrying out a dehydration reaction on 2,2,6,6-tetramethyl-4-piperidone (called tetramethyl piperidone for short) and 1,6-hexanediamine to prepare a Schiff base intermediate; 2) carrying out a hydrogenation reaction on the Schiff base intermediate in the presence of a catalyst to obtain hexamethylenediamine piperidine. The preparation method disclosed by the application is low in reaction pressure, and the requirements of the bearing pressure of equipment are reduced, so that the production safety is greatly improved and the cost is reduced; a non-polar solvent is used, so that side effects are reduced, and a post-treatment method is simple and convenient, so that the production efficiency is increased, industrialized mass production can be adapted better, and the obtained target compound is high in purity and slight in colour.

Description

technical field [0001] The present invention relates to a preparation method of a compound, in particular to an intermediate for synthesizing a hindered amine light stabilizer——N,N-bis(2,2,6,6-tetramethyl-4-piperidinyl) -1,6-hexamethylenediamine (hexamethylenediamine piperidine for short) preparation method. Background technique [0002] Light stabilizer intermediate hexamethylenediamine piperidine (CAS No.: 61260-55-7) is an important intermediate in the production of hindered amine light stabilizers, hindered amine light stabilizers can improve the performance of plastics in strong light environments, the main application Used in the automotive and construction industries, as well as agricultural films. [0003] The structural formula of hexamethylenediamine piperidine is: [0004] [0005] In recent years, the market demand for this product has continued to grow, and it is currently in short supply. It is mainly sold to Europe, America, Asia-Pacific and other regions...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58
CPCC07D211/58
Inventor 李超刘冰宋君荣施波
Owner JIANGSU FEIXIANG CHEM
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