Method for synthesizing aliphatic/cycloaliphatic dicarbamate by one-pot reaction process

A dicarbamate and aliphatic technology, which is used in the synthesis of chemical product reaction intermediates, key intermediates aliphatic/cyclic dicarbamate, and non-phosgene synthesis of isocyanates, which can solve the problem of catalyst dosage. Large, low activity, no industrialization conditions, etc., to achieve the effect of less catalyst dosage, high atom utilization, and satisfying industrialization conditions

Inactive Publication Date: 2014-08-13
上海沣勃新材料科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Patent CN1231463C uses PbO, KOH, ZnCl2, Pd / C, HZSM5, HY, CH 3OK and others catalyze the reaction of aniline, urea and alcohol to synthesize aniline carbamate. Although the conditions are mild, the amount of catalyst used is large, the activity is not high, and the conversion rate is only about 20%, which is not suitable for industrialization.

Method used

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  • Method for synthesizing aliphatic/cycloaliphatic dicarbamate by one-pot reaction process
  • Method for synthesizing aliphatic/cycloaliphatic dicarbamate by one-pot reaction process

Examples

Experimental program
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Effect test

Embodiment 1

[0051] Add 0.5mol 1,4-cyclohexanediamine, 0.8mol urea, 5mol methanol and 0.008mol sodium acetate into a 500ml self-circulating reaction kettle with electromagnetic stirring and automatic temperature control system, and pass N 2 Replace the air in the kettle. Under magnetic stirring conditions, the temperature was raised to 180°C at a rate of about 5°C / min. After 10 hours of reaction, the reactor was cooled to room temperature and samples were taken for HPLC analysis. The results showed that the conversion rate was 96% and the selectivity was 88%.

Embodiment 2

[0053] Add 0.5mol of hexamethylenediamine, 1.5mol of urea, 4.5mol of ethanol and 0.005mol of calcium acetate into a 500ml self-circulating reactor with electromagnetic stirring and automatic temperature control system, and pass N 2 Replace the air in the kettle. Under magnetic stirring conditions, the temperature was raised to 270°C at a rate of about 3°C / min. After 8 hours of reaction, the reactor was cooled to room temperature and samples were taken for HPLC analysis. The results showed that the conversion rate was 98% and the selectivity was 95%.

Embodiment 3

[0055] Add 0.5mol 4,4'-diaminodicyclohexylmethane, 1.0mol urea, 3.5mol n-propanol and 0.004mol zinc acetate into a self-circulating reactor with a volume of 500ml equipped with electromagnetic stirring and automatic temperature control system. N 2 Replace the air in the kettle. Under magnetic stirring conditions, the temperature was raised to 350°C at a rate of about 8°C / min. After 5 hours of reaction, the reactor was cooled to room temperature and samples were taken for HPLC analysis. The results showed that the conversion rate was 91% and the selectivity was 89%.

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Abstract

The invention discloses a method for synthesizing aliphatic/cycloaliphatic dicarbamate by a one-pot reaction process. The method comprises the following steps: placing aliphatic/cycloaliphatic diamine, urea, fatty alcohol and a catalyst into a self-circulation reaction kettle with protective gas; and performing the one-pot reaction process at reaction temperature of 100-450 DEG C and reaction pressure of 0.1-5MPa for 0.5-20 hours so as to prepare the aliphatic/cycloaliphatic dicarbamate, wherein the mole ratio of the aliphatic/cycloaliphatic diamine to the catalyst is 1:(0.0001-0.2), the mole ratio of the aliphatic/cycloaliphatic diamine to the urea to the fatty alcohol is 1:(1-10):(1-15), the catalyst refers to one or more types of acetate of potassium, magnesium, calcium, tin, lead, bismuth, zirconium, zinc, cerium, chromium, molybdenum, manganese, ferrum, cobalt and nickel elements. According to the method, the one-pot reaction process is adopted, so that the technological conditions are simple and moderate; the catalyst is low in use amount and is cheap and easily available; solvents are not needed; the reactivity, the selectivity and the atom utilization rate are high, and the requirements on industrialization conditions can be met.

Description

[0001] technical field [0002] The invention belongs to the field of organic chemistry, and relates to a reaction intermediate product of a chemical product, in particular to a method for synthesizing an aliphatic / cyclic diurethane which is a key intermediate of non-phosgene synthesis of isocyanate. Background technique [0003] Isocyanate is an important class of organic compounds and is the main raw material for the synthesis of polyurethane. It can be widely used in plastics, paints, pesticides, dyes, adhesives, leather, rubber, fibers and other polymer fields. Among them, aliphatic (cyclic) isocyanates, such as 4,4'-dicyclohexylmethane diisocyanate (H 12 MDI), 1,6-hexamethylene diisocyanate (HDI) and isophorone diisocyanate (IPDI), etc., its polyurethane products have excellent mechanical properties, no yellowing, chemical corrosion resistance, and beautiful appearance. [0004] The traditional production method of isocyanate is the phosgene method. This method has a m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/24C07C271/20C07C269/04B01J19/24B01F5/20B01F3/04
Inventor 谭学峰赵战如于涛
Owner 上海沣勃新材料科技有限公司
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