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Preparation method of 1,5-naphthalene diisocyanate

A technology of naphthalene diisocyanate and acid-binding agent, which is applied in the field of preparation of 1,5-naphthalene diisocyanate, which can solve the problems of unconformity with atom economy, complex process flow, and highly toxic phosgene, and achieve redox catalytic performance Excellent, simple process, high reactivity and stability

Active Publication Date: 2019-07-30
万仑新材料(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Patent No. CN103274966B discloses a method for preparing 1,5-naphthalene diisocyanate by solid-state phosgene method. Although the preparation process of phosgene method is quite mature, phosgene is highly toxic, seriously pollutes the environment, and is a by-product in the synthesis A lot of hydrochloric acid
Patent No. CN103450047B discloses a method for preparing 5-naphthalene diisocyanate, but the method has low yield per unit efficiency and complicated process flow, and hydrogenation and nitrogenation in the reaction process need to remove the organic solvent after the reaction, which does not conform to atomic economy

Method used

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  • Preparation method of 1,5-naphthalene diisocyanate
  • Preparation method of 1,5-naphthalene diisocyanate
  • Preparation method of 1,5-naphthalene diisocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 0.0240g (0.02mmol) copper-centered polyoxometalates [NH 4 ] 4 [CuMo 6 o 18 (OH) 6 ]·7H 2 O(CuMo 6 ), 0.3164g (2mmol) 1,5-diaminonaphthalene, 6mL anhydrous acetonitrile solvent, 0.2164g (4mmol) phenylsilane, 0.1012g (1mmol) triethylamine, 0.3067g (2mmol) phosphorus oxychloride, and finally in An oxygen balloon filled with carbon dioxide was put over the reaction tube and reacted at 30°C for 12h. After the reaction, the above sample was taken to measure GC-MS. The test analysis showed that the conversion rate of the reaction substrate was greater than 93%, and the product selectivity was 89%. After separation and purification, a light yellow crystalline solid was obtained, which was confirmed by NMR to be the product 1,5-naphthalene diisocyanate.

Embodiment 2

[0029] Add 0.0240 g (0.02 mmol) of chromium-centered polyoxometalates [NH 4 ] 3 [CrMo 6 o 18 (OH) 6 ]·7H 2 O(CrMo 6 ), 0.3164g (2mmol) 1,5-diaminonaphthalene, 6mL anhydrous acetonitrile solvent, 0.2164g (4mmol) phenylsilane, 0.1012g (1mmol) triethylamine, 0.3067g (2mmol) phosphorus oxychloride, and finally in An oxygen balloon filled with carbon dioxide was put over the reaction tube and reacted at 30°C for 12h. After the reaction, the above sample was taken to measure GC-MS. It was found that the conversion rate of the reaction substrate was greater than 90%, and the selectivity of the product was 91%. After separation and purification, a light yellow crystalline solid was obtained, which was confirmed to be the product 1,5-naphthalene diisocyanate by NMR. .

Embodiment 3

[0031] Add 0.0240 g (0.02 mmol) iron-centered polyoxometalate [NH 4 ] 3 [FeMo 6 o 18 (OH) 6 ]·7H 2 O(FeMo 6 ), 0.3164g (2mmol) 1,5-diaminonaphthalene, 6mL anhydrous acetonitrile solvent, 0.2164g (4mmol) phenylsilane, 0.1012g (1mmol) triethylamine, 0.3067g (2mmol) phosphorus oxychloride, and finally in An oxygen balloon filled with carbon dioxide was put over the reaction tube and reacted at 30°C for 12h. After the reaction, the above sample was taken to measure GC-MS. It was found that the conversion rate of the reaction substrate was greater than 96%, and the selectivity of the product was 93%. After separation and purification, a light yellow crystalline solid was obtained, which was confirmed to be the product 1,5-naphthalene diisocyanate by NMR. .

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Abstract

The invention relates to a preparation method of 1,5-naphthalene diisocyanate. The preparation method comprises the steps that a catalyst polyoxometallate and a solvent are added into a reaction container; then raw materials including 1,5-diaminonaphthalene, phenylsilane, an acid-binding agent and a dehydrating agent are added, and the materials are evenly mixed; finally, gaseous carbon dioxide isadded, the materials are stirred magnetically at a certain temperature for sufficient reaction, and the product is obtained. According to the method, an M-Anderson type heteropoly acid serves as a catalyst, the catalyst is mild in required reaction condition, high in specific selectivity, capable of being recycled and environmentally friendly, the cleanness of industrial reaction is improved, theeconomical efficiency of the technology is improved, the manufacturing cost and generation of three wastes are reduced, the environment-friendly pressure is reduced, and industrial production is facilitated.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 1,5-naphthalene diisocyanate. Background technique [0002] 1,5-Naphthalene diisocyanate can be used in workplaces where ordinary polyurethane cannot meet the requirements or is prematurely damaged due to its high hardness, good resilience, good heat resistance, excellent dynamic performance, and good wear resistance. , such as high temperature and oily environment, so it is mostly used as a raw material for the synthesis of advanced polyurethane. In addition, it is also often used in pesticides and pharmaceutical intermediates. Due to the high melting point of 1,5-dinaphthyl isocyanate products, and the advantages of excellent elasticity, good dynamic performance, and long life, its application prospects are very broad, and the current research on the synthesis of 1,5-dinaphthyl isocyanate is still in its infancy. The development of a new clea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C263/10C07C265/14B01J31/16B01J31/34B01J27/188
CPCB01J23/28B01J23/881B01J23/883B01J23/885B01J27/188B01J31/34B01J2231/4277C07C263/10C07C265/14
Inventor 余焓但德敏吴志康魏永革韩生
Owner 万仑新材料(上海)有限公司
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