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Diphenylethane diisocyanate prepared by a solid phosgene method and application thereof

A technology of diphenylethane diisocyanate and diaminodiphenylethane, which is applied in the field of polymer material monomer preparation, can solve the problems of strong corrosiveness of by-product hydrochloric acid, affecting product application performance, and difficulty in removing residual chlorine. , to achieve the effect of strong reaction stability, safe use, improved quality and yield

Inactive Publication Date: 2020-03-24
山东华阳农药化工集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing isocyanates are generally produced by the phosgene method, but phosgene is highly toxic, has great potential safety hazards, and the by-product hydrochloric a

Method used

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  • Diphenylethane diisocyanate prepared by a solid phosgene method and application thereof
  • Diphenylethane diisocyanate prepared by a solid phosgene method and application thereof
  • Diphenylethane diisocyanate prepared by a solid phosgene method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add 20.0L of chloroform to the reaction kettle, add 2.12kg of 4,4'-diaminodiphenylethane and stir to dissolve, then add 1.0L of DMF, freeze to -20℃, add 2.17kg of solid phosgene while stirring, maintain- After reacting at 20°C to 0°C for 1 hour, heat to reflux for 2-12 hours,

[0043] Developing agent: petroleum ether-ethyl acetate (1:1), color developing agent: 5% phosphomolybdic acid ethanol solution, TLC detects all the reaction of 4,4'-diaminodiphenylethane, the white is obtained after removing the solvent The powdered product is 2.55kg. The purity of the product detected by HPLC normalization method was 97.5%, 13 C NMR(100MHz, CDCl 3 )δ139.32,139.32,130.80,130.80,130.28,130.28,130.28,130.28,127.71,127.71,125.10,125.10,125.10,125.10,37.41,34.42; FAB-HRMS: M / e(264.2762), molecular formula: C 16 H 12 O 2 N 2 , Which is diphenylethane-4,4'-diisocyanate (EDI-a1).

[0044] According to the method similar to Example 4, selecting suitable starting materials 5,5'-diaminodipheny...

Embodiment 2

[0046] Add 30.0L of dichloromethane into the reaction kettle, add 2.40kg of 2,2'-dimethyl-4,4'-diaminodiphenylethane and stir to dissolve, then add 1.0L of DMF, and freeze to -20℃. Add 2.20kg of solid phosgene while stirring, keep at -20℃ to 0℃ for 1 hour, then heat and reflux for 2-12 hours.

[0047] Developing reagent: petroleum ether-ethyl acetate (1:1), developer: 5% phosphomolybdic acid ethanol solution, TLC detection 2,2'-dimethyl-4,4'-diaminodiphenylethane For the entire reaction, nitrogen gas was bubbled, hydrogen chloride was removed in vacuum for 0.5 h, and the solvent was removed to obtain 2.80 kg of white powder. The purity of the product detected by HPLC normalization method was 97.0%, 13 C NMR(100MHz, CDCl 3 )δ136.74,136.74,134.41,134.41,130.70,130.70,130.13,130.13,127.71,127.71,126.50,126.50,122.02,122.02,35.39,35.39,19.10,19.10; FAB-HRMS: M / e(292.3300), Molecular formula: C 18 H 16 O 2 N 2 , Which is 2,2'-dimethyl-diphenylethane-4,4'-diisocyanate (EDI-b1).

Embodiment 3

[0049] Add 10.0L DMF to the reactor, add 2.40kg of 2,2'-dimethyl-5,5'-diaminodiphenylethane, stir to dissolve, freeze to -20℃, add 2.95kg of solid phosgene while stirring After reacting at -20°C to 0°C for 1 hour, heat to 150°C and continue to react for 2-12 hours.

[0050] Developing reagent: petroleum ether-ethyl acetate (1:1), developer: 5% phosphomolybdic acid ethanol solution, TLC detection 2,2'-dimethyl-5,5'-diaminodiphenylethane For the entire reaction, nitrogen gas was bubbled, hydrogen chloride was removed in vacuum for 0.5 h, and the solvent was removed to obtain 2.75 kg of white powder. The purity of the product detected by HPLC normalization method was 98.0%, 13 C NMR(100MHz, CDCl 3 )δ138.30,138.30,132.71,132.71,130.47,130.47,128.82,128.82,127.40,127.40,125.29,125.29,122.21,122.21,36.39,36.39,19.08,19.08; FAB-HRMS: M / e(292.3298), Molecular formula: C 18 H 16 O 2 N 2 , Which is 2,2'-dimethyl-diphenylethane-5,5'-diisocyanate (EDI-b2).

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Abstract

The invention discloses diphenylethane diisocyanate prepared by a solid phosgene method and an application thereof, and relates to the technical field of preparation of high polymer material monomers.The method comprises the following steps: dissolving diaminodiphenyl ethane in a solvent; adding solid phosgene under the action of a catalyst; carrying out reaction at -20 to 20 DEG C for a certaintime; heating the substances to 80 to 200 DEG C and continuing to carry out reaction to the end point; and carrying out separation and purification to obtain a diphenylethane diisocyanate (EDI) compound. The EDI is prepared by adopting a solid phosgene method, so that the working condition is improved, the quality and the yield of the product EDI are improved, and meanwhile, the solid phosgene isrelatively strong in reaction stability and relatively safe to use.

Description

Technical field [0001] The invention discloses a solid phosgene method for preparing diphenylethane diisocyanate and its application, and relates to the technical field of polymer material monomer preparation. Background technique [0002] Polyurethane can be synthesized into many valuable synthetic materials, such as polyurethane foam, which is mainly used for heat preservation and transportation, detachable heat insulation board and rigid foam board. Among them, polyurethane semi-rigid foams can carry high loads and are used in cushions, mattresses and various products with good cushioning and shock resistance and impact energy in transportation vehicles such as airplanes, automobiles, and trains. They are widely used in the transportation industry. The products of soft polyurethane foam are mainly high resilience soft foam, fabric lining, car seat cushion, etc. Polyurethane monomers can also be used as adhesives, which can be used in daily household goods adhesives, construct...

Claims

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Application Information

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IPC IPC(8): C07C263/10C07C265/14C08G18/76
CPCC07C263/10C07C265/14C08G18/7657
Inventor 刘玉法闫新华孙绪兵
Owner 山东华阳农药化工集团有限公司
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