Preparation method and application of C23-38 cycloaliphatic diisocyanate

A technology of diisocyanate and cycloaliphatic diisocyanate, which is applied in the field of preparation of C23-38 cycloaliphatic diisocyanate, can solve the problems of difficult production, difficult separation, large molecular weight, etc., and achieve low production difficulty, low cost, and high configuration single effect

Active Publication Date: 2014-12-10
陕西聚泰新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 2-octyl-3,4-bis(7-isocyanatoheptyl)-1-hexylcyclohexane disclosed in Chinese patent ZL200610154226.2 is a diisocyanate that can meet these requirements, but because its molecular weight is too large, Production is also relatively difficult, and the cost is naturally high, so it can only be used in some special industries. It is theoretically speculated that if the molecular weight is controlled between 300-500, its toxicity is relatively low and production is relatively easy.
[0004] At present, the basic raw material selected for the preparation method of dibasic acid ester, an intermediate product of cycloaliphatic diisocyanate, is oleic acid or ester, which contains three double bonds, and easily produces by-products in the reaction preparation process, and the by-products The structure is similar, not easy to separate

Method used

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  • Preparation method and application of C23-38 cycloaliphatic diisocyanate
  • Preparation method and application of C23-38 cycloaliphatic diisocyanate
  • Preparation method and application of C23-38 cycloaliphatic diisocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation C 23 Cycloaliphatic diisocyanate

[0037] Step 1: add 500g (1.7mol) dehydrated methyl ricinoleate, 146.2g (1.7mol) methyl acrylate, and inhibitor hydroquinone 1.5g in the 2000mL pressure reactor, and replace the air in the kettle with nitrogen, Heating to 160-180°C and reacting for 3.5 hours to obtain the crude dibasic acid methyl ester.

[0038] It should be noted that the reaction of dehydrated ricinoleic acid methyl ester and methyl acrylate in this embodiment can be replaced by the reaction of dehydrated ricinoleic acid and acrylic acid, and the dibasic acid methyl ester in the following steps can also be the corresponding binary Acids, in view of space, are not given one by one, and in this embodiment, only the reaction of dehydrated ricinoleic acid methyl ester and methyl acrylate is taken as an example.

[0039] Step 2: Add 380 g (1.0 mol) of the dibasic acid methyl ester generated in step 1 and 5 g of tributyl phosphate into a 1000 mL fo...

Embodiment 2

[0053] Example 2: Preparation C 24 Cycloaliphatic diisocyanate

[0054] The difference between this embodiment and Example 1 is that the raw materials for preparing cycloaliphatic diisocyanate are different, and the present embodiment uses 500g (1.7mol) dehydrated methyl ricinoleate and 170.0g (1.7mol) α-methyl methacrylate Reaction, preparation process is identical with embodiment 1, obtains target product C 24 Aliphatic diisocyanate, namely 1-hexyl-3'-methyl-3-(2-isocyanatoethyl)-4-(8-isocyanatooctyl)cyclohexane.

[0055] Molecular formula: C 24 h 42 N 2 o 2

[0056] Molecular weight: 390

[0057] Appearance: light yellow oily liquid

[0058] NCO content: 19.4-21.5%

[0059] Structural formula:

[0060]

[0061] The infrared spectrometry data are as follows:

[0062] IR(kBr)γ(cm -1 ):2853.7, 2924.4 (-CH 2 ,-CH 3 C-H stretching vibration);

[0063] 1463.81354.2 (C-CH 3 , C-H deformation vibration);

[0064] 723.0–(CH 2 ) 4 skeleton vibration;

[0065] 2...

Embodiment 3

[0066] Example 3: Preparation C 24 Cycloaliphatic diisocyanate

[0067] The difference between this embodiment and Example 1 is that the raw materials for preparing cycloaliphatic diisocyanate are different, and the present embodiment uses 500g (1.7mol) dehydrated methyl ricinoleate and 170.0g (1.7mol) β-methyl methacrylate Reaction, preparation process is identical with embodiment 1, obtains target product C 24 Aliphatic diisocyanate, namely 1-hexyl-2-methyl-3-(2-isocyanatoethyl)-4-(8-isocyanatooctyl)cyclohexane.

[0068] Molecular formula: C 24 h 42 N 2 o 2

[0069] Molecular weight: 390

[0070] Appearance: light yellow oily liquid

[0071] NCO content: 19.4-21.5%

[0072] Structural formula:

[0073]

[0074] The infrared spectrometry data are as follows:

[0075] IR(kBr)γ(cm -1 ):2853.7, 2924.4 (-CH 2 ,-CH 3 C-H stretching vibration);

[0076] 1463.81354.2 (C-CH 3 , C-H deformation vibration);

[0077] 723.0–(CH 2 ) 4 skeleton vibration;

[0078] 22...

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Abstract

The invention provides a preparation method and application of C23-38 cycloaliphatic diisocyanate. The method comprises the following steps: preparing unsaturated cycloaliphatic diacid or ester by using dehydrated ricinoleic acid or ester and a double-bond-containing fatty acid or ester as raw materials; preparing corresponding cyanogens through ammoniation dehydration; preparing corresponding saturated diamine by catalytic hydrogenation; and finally reacting with phosgene to prepare the corresponding cycloaliphatic diisocyanate. The acid or ester extracted from ricinus oil is used as a basic raw material, the production raw material is available, the cost is low, the configuration of the prepared cycloaliphatic diisocyanate is single, the side reaction is less, the molecular weight is between 300-500, the production difficulty is small, the preparation method is simple to operate, mild in condition, environment-friendly, safe in production, and in favor of industrial popularization application, and can be used for preparing polyurethane lacquer, coating, elastomer, adhesive, textile finishing agent and important component of rocket propellant.

Description

technical field [0001] The present invention relates to a class of alicyclic diisocyanates, in particular to a C 23-38 Preparation method and use of cycloaliphatic diisocyanate. Background technique [0002] Isocyanate is a substance with high reactivity, especially diisocyanate is a kind of substance that is used in a huge amount in the field of material industry. At present, toluene diisocyanate (TDI) is used in the largest amount, but due to the high toxicity of aromatic diisocyanate, Even the degradation products are relatively toxic and carcinogenic, and the pollution in the production process is relatively large, and the materials made of it are easy to yellow, so people turn their attention to alicyclic diisocyanate and isophorone diisocyanate. (IPDI) is one of them, but due to its small molecular weight and relatively high volatility, IPDI has relatively high inhalation toxicity. Therefore, people have been searching for less toxic or even non-toxic aliphatic diisoc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C265/14C07C263/10
Inventor 刘林学张明英李建民
Owner 陕西聚泰新材料科技有限公司
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