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Preparation method of high-anomer 4,4'-diaminodicyclohexylmethane

A technology of diaminodicyclohexylmethane and diaminodicyclohexyl, which is applied in the field of organic compound preparation, can solve the problems of unsuitability for large-scale industrial production, low yield of PACM50, and generation of three wastes, so as to reduce equipment investment and safety Effects of risk reduction, reduction of recycling process, and ease of operation

Active Publication Date: 2018-09-11
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The flow of such methods is very complicated, while the yield of PACM50 is low, and a large amount of three wastes are generated, so it is not suitable for large-scale industrial production

Method used

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  • Preparation method of high-anomer 4,4'-diaminodicyclohexylmethane
  • Preparation method of high-anomer 4,4'-diaminodicyclohexylmethane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In a 2 L volume autoclave reactor with built-in filter, add 15 g Ru / LiAlO 2 (metal content 4wt%) catalyzer and 500g PACM20 (reverse body content is 18.3%), add 0.8g tetramethyl ammonium hydroxide, with the N of 10bar (absolute pressure) 2 After three replacements, fill with 1 bar (absolute pressure) of N 2 . Raise the temperature to 110°C, stir the modification reaction for 1 hour, and start the isomerization reaction when the temperature is raised to 210°C, and take samples online through the built-in filter every 2 hours for gas chromatography analysis. The analysis results are shown in Table 1. After 10 hours, the anti-anti-body content in the reaction solution reached over 50%, the temperature was lowered to stop the reaction, and the reaction was filtered to obtain 4,4'-diaminodicyclohexylmethane (PACM50) with high anti-anti-body content.

[0041] Table 1 reaction result changes table (unit / wt%) with reaction time

[0042] Reaction time / h

anti-anti ...

Embodiment 2

[0047] In a 2 L volume autoclave reactor with built-in filter, add 25 g of Ru / LiAlO 2 (metal content 4wt%) catalyzer and 500g PACM20 (reverse body content is 19.0%), add 1.5g tetramethyl ammonium hydroxide, with the N of 10bar (absolute pressure) 2 After three replacements, fill with 1 bar (absolute pressure) of N 2 . Raise the temperature to 100°C, stir the modification reaction for 1 hour, then start the isomerization reaction when the temperature is raised to 190°C, and take samples online through the built-in filter every 2 hours for gas chromatography analysis. The analysis results are shown in Table 3. After 10 hours, the anti-anti-body content in the reaction solution reached over 50%, the temperature was lowered to stop the reaction, and the reaction was filtered to obtain 4,4'-diaminodicyclohexylmethane (PACM50) with high anti-anti-body content.

[0048] Table 3 reaction result changes table (unit / wt%) with reaction time

[0049] Reaction time / h

anti-a...

Embodiment 3

[0054] In a 2 L volume autoclave reactor with built-in filter, add 25 g of Ru / LiAlO 2 (metal content 4wt%) catalyst and 500g PACM20 (reverse body content is 21.1%), add 1.5g tetramethyl ammonium hydroxide, with the N of 10bar (absolute pressure) 2 After three replacements, fill with 10bar (absolute pressure) of N 2 . Raise the temperature to 100°C, stir the modification reaction for 1 hour, then start the isomerization reaction when the temperature is raised to 190°C, and take samples online through the built-in filter every 2 hours for gas chromatography analysis. The analysis results are shown in Table 5. After 10 hours, the anti-anti-body content in the reaction solution reached over 50%, the temperature was lowered to stop the reaction, and the reaction was filtered to obtain 4,4'-diaminodicyclohexylmethane (PACM50) with high anti-anti-body content.

[0055] Table 5 reaction result changes table (unit / wt%) with reaction time

[0056] Reaction time / h

anti-an...

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Abstract

The invention discloses a preparation method of high-anomer 4,4'-diaminodicyclohexylmethane. The content of anomer (PACM50) in the prepared product is 45-55 wt%. The preparation method comprises the following steps: performing a modification reaction on a raw material low-anomer 4,4'-diaminodicyclohexylmethane at 100-110 DEG C under the action of a catalyst and a modifier, raising the temperatureto 120-250 DEG C, and performing an isomerization reaction to prepare the high-anomer 4,4'-diaminodicyclohexylmethane. The method allows the PACM20 conversion rate to reach 99-100% and the PACM50 yield to reach 98-99%. The method has the advantages of realization of a high-temperature catalysis reaction under solvent-free and low-pressure nitrogen conditions without high-pressure nitrogen, simplicity in operation, safety, environmental protection, and suitableness for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and relates to a preparation method of 4,4'-diaminodicyclohexylmethane with high anti-antibody content. Background technique [0002] 4,4’-Diaminodicyclohexylmethane (PACM for short) has three stereoisomers with different thermodynamic properties: anti-trans, cis-trans and cis-cis. The composition ratio of the three isomers determines the properties and uses of PACM products and their follow-up products, and it is difficult to obtain PACM products with a single or specific ratio of isomers by means of separation, so the industry is accustomed to using the anti-anti-body content in PACM to determine Define PACM products with different specifications and uses. Wherein anti-antibody content below 24wt% is collectively referred to as PACM20, mainly as the anti-aging polyurethane-dicyclohexylmethane diisocyanate (H 12 MDI), the isocyanate can be used to prepare light and stable ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/82C07C211/36
CPCC07B2200/09C07C209/82C07C2601/14C07C211/36
Inventor 李鑫张聪颖刘振国任树杰唐磊刘志鹏吴健黎源姜庆梅宋锦宏华卫琦丁皓
Owner WANHUA CHEM GRP CO LTD
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