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Synthesis method of difurfuryl methane diisocyanate

A technology of diisocyanate and difurfurylmethane, which is applied in the field of synthesis of difurfurylmethane diisocyanate, can solve the problems of low selectivity and yield of target product, difficulty in expanding production scale, strong corrosiveness of hydrochloric acid, etc. Hydrochloric acid corrosion and product separation problems, high conversion rate and selectivity, and the effect of renewable raw material resources

Inactive Publication Date: 2014-05-21
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The disadvantages of the phosgene method mainly include: on the one hand, phosgene is highly toxic, volatile, and has huge potential accident hazards. At the same time, the associated hydrochloric acid is highly corrosive, and the requirements for protection and equipment materials are very strict; 1. Isocyanate can react with the reactant amine to generate various by-products such as urea; the selectivity and yield of the target product obtained by each step reaction are not high
On the other hand, the environmental pollution is large, and the product separation is difficult, which makes it difficult to expand the production scale.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0026] The synthetic method of difurfurylmethane diisocyanate provided by the invention, its processing step is as follows:

[0027] (1) Fully mix furfurylamine and aldehyde at room temperature, mix well and continue to stir until the temperature of the mixture rises to 30-60°C, add the catalyst to the mixture while stirring, keep the temperature at 30-45°C and continue to stir for 10- After 30 minutes, uniformly heat the mixture to 100-140°C under a pressure of 0.1-0.5MPa within 60-100 minutes, and keep at this temperature for 20-60 minutes;

[0028] Then, after the mixture is cooled, it is neutralized by adding an aqueous sodium hydroxide solution with a certain mass percent concentration of 20-50% under stirring. The lower aqueous phase was then siphoned off. Excess furfurylamine and residual water were distilled off.

[0029] The mixture of diamines and polyamines produced after distillation contains 50%-80% by mass of difurfurylmethanediamine, a total of 1%-12% of difur...

Embodiment 1

[0036] a) Preparation of polyamine mixture

[0037]In a stirred container, 130 grams of furfurylamine and 50 grams of formalin (formaldehyde aqueous solution with a concentration of 30% by mass) were fully mixed at 25°C, and the stirring was continued until the temperature of the mixture rose to 60°C. Stirring was stopped and the upper aqueous phase was separated. Then add 4 grams of PW / Hβ (wherein the mass percentage of PW is 10%), re-stirring and cooling. The temperature was maintained at 45°C. After continuing to stir at this temperature for 30 minutes, heating was used instead of cooling, and the mixture was uniformly heated to 140° C. within 100 minutes under a pressure of 0.1 MPa, and kept at this temperature for 20 minutes.

[0038] The mixture was then cooled to 100° C., released to normal pressure and neutralized by adding 34 g of a 50% by weight aqueous sodium hydroxide solution with stirring. After stirring had ceased, the phases were allowed to settle and the lo...

Embodiment 2

[0048] a) Preparation of polyamine mixture

[0049] In a stirred vessel, 130 grams of furfurylamine and 40 grams of acetaldehyde were thoroughly mixed at 25°C and stirring continued until the mixture warmed to 60°C. Stirring was stopped and the upper aqueous phase was separated. Then add 5 grams of PW / SBA-15 (wherein the mass percentage of PW is 15%), stir and cool again. The temperature was maintained at 50°C. After continuing stirring at this temperature for 25 minutes, heating was used instead of cooling, and the mixture was uniformly heated to 130° C. within 100 minutes under a pressure of 0.4 MPa, and kept at this temperature for 15 minutes.

[0050] The mixture was then cooled to 100° C., released to normal pressure, and neutralized by adding 38 g of a 45% by weight aqueous sodium hydroxide solution with stirring. After stirring had ceased, the phases were allowed to settle and the lower aqueous phase was then siphoned off. Excess aniline and residual water were remo...

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Abstract

The invention belongs to the field of chemical engineering technology, and particularly relates to a synthesis method of difurfuryl methane diisocyanate. The synthesis method comprises the concrete steps: a) furfuryl amine and aldehyde are subjected to high-selective one-step conversion into methane difurfuryl diamine (MDFA); b) MDFA and carbonic ester are subjected to carbalkoxylation to synthesize methane difurfuryl diamino ester (MDFC); and c) followed by, MDFC is decomposed to obtain the corresponding difurfuryl methane diisocyanate; and separating through distillation to obtain a mixture of diisocyanate ester and polyisocyanate ester, wherein the mixture contains 50%-80% by mass of difurfuryl methane diisocyanate. The synthesis method of difurfuryl methane diisocyanate has the advantages of simple and safe process, mild reaction conditions and high yield, and can achieve cleaning production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, in particular to a method for synthesizing difurfurylmethane diisocyanate. Background technique [0002] Difurfurylmethane diisocyanate (MDFI) has a similar structure to diphenylmethane diisocyanate (MDI). Studies have shown that it can replace MDI for the production of new polyurethane products or as an adhesive in the furniture industry. The industrialization of raw furfurylamine and the research on MDFI have also attracted great attention. However, the existing methods in the literature are limited to the phosgene route. The first is the preparation of difurfurylmethanediamine (MDFA). There are two existing preparation methods: Scheme: scheme (1) react furfurylamine with carbonyl compound formic acid to generate furfuramide derivatives; condense furfuramide and formaldehyde to generate difurfurylmethane dicarboxamide; release amine groups under alkaline conditions to obtain MDFA. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 牟新东郭星翠王喜成彭功名曹泉
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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