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Method for preparing hexamethylene diamine

A technology of hexamethylenediamine and hexamethylenediol, applied in the field of preparation of hexamethylenediamine, which can solve the problems of high toxicity of raw material adiponitrile, unfavorable large-scale continuous industrial production, and harsh reaction conditions, so as to reduce the one-time investment and production cost , easy to operate for a long time, and the effect of simple reaction process

Inactive Publication Date: 2017-06-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

[0008] Judging from the current existing literature and technologies, most of the production technologies of hexamethylenediamine have disadvantages such as poor selectivity, difficult product separation, harsh reaction conditions, and low yield. The preparation methods are not conducive to large-scale continuous industrial production.
There are still two fatal problems in the industrialized hydrogenation of adiponitrile to hexamethylenediamine: one is the Raney Ni catalyst commonly used in the route, which is prone to spontaneous combustion in the air, and there are major safety hazards in the preparation process; the other is The raw material adiponitrile is highly toxic and depends on imports, which is expensive and subject to human

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Embodiment 1

[0024] Weigh the above 15%Ni-1.6%Re-1.2%B / Al 2 o 3 Catalyst 3.2 grams (about 4ml), is packed in the fixed-bed reactor. The catalyst is activated by hydrogenation treatment before use. The activation conditions are: T=375°C; P=atmospheric pressure, GHSV=2000h -1 , The reduction time is 4 hours. When the temperature in the reactor is naturally lowered to 160°C, the pressure is increased to 8MPa. After the system is stable, the NH 3 / 1,6-Hexanediol The liquid with hydroxyl group=10 (molar ratio) flows into the reactor through the pump, and adjusts the liquid space velocity of 1,6-Hexanediol to 0.5h -1 , H in the reaction system 2 The content is 2.5mol%, and the reaction is carried out, and the reaction time is 50 hours, and the sample is analyzed. SE-30 capillary column, FID detector, isobutanol as internal standard for quantitative analysis, the reaction results are shown in Table 1.

Embodiment 2

[0026] Weigh the above 15%Ni-1.6%Re-1.2%B / Al 2 o 3 Catalyst 3.2 grams (about 4ml), is packed in the fixed-bed reactor. The catalyst is activated by hydrogenation treatment before use. The activation conditions are: T=375°C; P=atmospheric pressure, GHSV=2000h -1, The reduction time is 4 hours. When the temperature in the reactor is naturally lowered to 120°C, the pressure is increased to 8MPa. After the system is stable, the NH 3 / 1,6-Hexanediol The liquid with hydroxyl group=10 (molar ratio) flows into the reactor through the pump, and adjusts the liquid space velocity of 1,6-Hexanediol to 0.5h -1 , H in the reaction system 2 The content is 2.5mol%, and the reaction is carried out, and the reaction time is 50 hours, and the sample is analyzed. SE-30 capillary column, FID detector, isobutanol as internal standard for quantitative analysis, the reaction results are shown in Table 1.

Embodiment 3

[0028] Weigh the above 15%Ni-1.6%Re-1.2%B / Al 2 o 3 Catalyst 3.2 grams (about 4ml), is packed in the fixed-bed reactor. The catalyst is activated by hydrogenation treatment before use. The activation conditions are: T=375°C; P=atmospheric pressure, GHSV=2000h -1 , The reduction time is 4 hours. When the temperature in the reactor is naturally lowered to 230°C, the pressure is increased to 8MPa. After the system is stable, the NH 3 / 1,6-Hexanediol The liquid with hydroxyl group=10 (molar ratio) flows into the reactor through the pump, and adjusts the liquid space velocity of 1,6-Hexanediol to 0.5h -1 , H in the reaction system 2 The content is 2.5mol%, and the reaction is carried out, and the reaction time is 50 hours, and the sample is analyzed. SE-30 capillary column, FID detector, isobutanol as internal standard for quantitative analysis, the reaction results are shown in Table 1.

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Abstract

The invention relates to a method for preparing hexamethylene diamine by using hexanediol, or amino hexanol or a hexanediol / amino hexanol mixture as a raw material. The method comprises the following steps: mixing the hexanediol, or the amino hexanol or the hexanediol / amino hexanol mixture with liquid ammonia according to a certain proportion, pumping the mixture into a reactor, and reacting under the existence of a catalyst and hydrogen. According to the method disclosed by the invention, a novel catalyst is adopted, the catalytic performance is excellent, and long-time operation is easy; production of a hexamethylene diamine product by carrying out hydro-amination on the hexanediol, or the amino hexanol or the hexanediol / amino hexanol mixture can be realized under lower reaction pressure, compositions of the product can be flexibly changed by changing reaction conditions, the selectivity of a target product is increased, a reaction process is simple, the one-time investment and the production cost of a production device are reduced, separation of a reaction product and the catalyst is simple, and large-scale continuous industrial production can be easily realized.

Description

technical field [0001] The present invention relates to a method for preparing hexamethylenediamine, in more detail, relates to a method for preparing hexamethylenediamine by using hexanediol or aminohexanol or a mixture of hexanediol\aminohexanol and ammonia as raw materials under the condition of hydrogen Methods. Background technique [0002] Hexamethylenediamine is an important bifunctional compound. Due to the presence of two reactive functional groups in the molecule, a variety of important chemicals can be generated. Hexamethylenediamine is mainly used in the manufacture of AK salt, which is a nylon 66 monomer. Nylon 66 is the earliest polyamide to be industrialized, and it is still listed as the two most important polyamide varieties with nylon 6. Therefore, the development of diamine production technology has always been valued. Hexamethylenediamine is also used in the manufacture of other types of polyamides, such as nylon 610, nylon 612 and nylon 69, for the pr...

Claims

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Application Information

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IPC IPC(8): C07C211/12C07C209/16
CPCC07C209/16
Inventor 严丽丁云杰马雷吕元程显波马立新
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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