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2-octyl-3,4-di(7-diisocyanateheptyl)-1-hexylcyclohexane and its preparation method and use

An isocyanate and dimer acid technology, applied in the preparation of carboxylic acid nitrogen-containing derivatives, organic chemistry and other directions, can solve the problems of difficult industrialization, low yield, high toxicity, etc., and achieve the advantages of favorable industrialization, simple operation, and mild conditions.

Inactive Publication Date: 2008-01-09
刘林学 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of the phosgene method is that the process conditions are harsh, the toxicity is high, it is not easy to industrialize, the yield is low, the side reaction is easy to occur, and it brings inconvenience to the post-treatment, such as the reaction between the generated isocyanate and the raw material amine
It is reported that low molecular weight aliphatic isocyanate can be prepared by using sodium azide method, but it has not been used in the preparation of PRO1400

Method used

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  • 2-octyl-3,4-di(7-diisocyanateheptyl)-1-hexylcyclohexane and its preparation method and use
  • 2-octyl-3,4-di(7-diisocyanateheptyl)-1-hexylcyclohexane and its preparation method and use
  • 2-octyl-3,4-di(7-diisocyanateheptyl)-1-hexylcyclohexane and its preparation method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Example 1.2-octyl-3,4-bis(7-isocyanatoheptyl)-1-hexylcyclohexane)

[0037] step 1:

[0038] Put 350g xylene and 30g Pd (5%) / activated carbon catalyst (wet: dry weight 15g, 0.45g Pd) suspension into 2 liters of hydrogenation autoclave, then add 320g dimer acid (98%), draw separately Vacuum, nitrogen replacement, hydrogen replacement. The reaction mixture was stirred at 170-190° C., 1.5-2.0 Mp for about 7.5 hours, until the hydrogen absorption was complete, and the stirring was stopped. The material was filtered off under nitrogen pressure, leaving the catalyst in the filter. Use 350g xylene to backwash the catalyst into the reactor, add 320g dimer acid, repeat the hydrogenation, the catalyst activity does not decrease, carry out the hydrogenation 5 times in the same way, and reuse the catalyst 4 times, the obtained reaction mixture (colorless and transparent) was heated and dehydrated to obtain saturated dimer acid, which was reserved for the next step.

[0039] Step...

Embodiment 2

[0057] The preparation of embodiment 2.2-octyl-3,4-bis(7-isocyanatoheptyl)-1-hexylcyclohexane

[0058] According to the method similar to Example 1, only the reactions of steps 3 and 4 are combined. After adding sodium azide, the temperature is raised to above 120°C, and the azide compound generated by the sodium chloride generated without filtering is directly decomposed. Finish the product until the gas is no longer released, then filter sodium chloride, remove the solvent, and then molecularly distill under reduced pressure to obtain the target product.

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Abstract

Production of 2-octyl-3,4-di(7-isocyanate caprylic)-1-hexyl cyclohexane and fatty isocyanate containing it is carried out by hydrogenation catalyzing for dimmer acid between room temperature to 280 deg. C, dewatering for generated saturated dimmer acid, reacting with sulfurous chloride, reacting dimeric acid acyl bromide with sodium azide to generate dimeric acid azide, isomerization decomposing to convert into final product. It can be used to produce polyurethane varnish, elastomer, adhesive, spinning finishing agent and rocket impeller.

Description

technical field [0001] The present invention relates to 2-octyl-3,4-bis(7-isocyanatoheptyl)-1-hexylcyclohexane (hereinafter referred to as PRO1400) and its preparation method, and its application for producing various auxiliary agents. The invention also relates to a process for the preparation of aliphatic isocyanates. Background technique [0002] In the retrieved literature, there are mainly reports on the preparation of corresponding isocyanates or 2-heptyl-3,4-di(9-isocyanate nonyl)-1-pentylcyclohexane (DDI1410) from low-molecular-weight fatty acids or amines. Preparation method, but the phosgene method is generally used, and only low molecular weight aliphatic isocyanates are seen by the sodium azide method. The disadvantages of the phosgene method are harsh process conditions, high toxicity, difficult industrialization, low yield, prone to side reactions, and inconvenience to post-processing, such as the reaction between the generated isocyanate and the raw material ...

Claims

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Application Information

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IPC IPC(8): C07C265/04C07C263/12
Inventor 刘林学王研赵彬侠
Owner 刘林学
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