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Method for producing isocyanate compound

A technology of isocyanate and naphthalene diisocyanate, applied in the novel preparation field, can solve the problem of no carbonyl fluoride technology research, etc., and achieve the effects of low toxicity and high safety

Inactive Publication Date: 2011-05-11
NAT INST OF ADVANCED IND SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0027] This point is just as mentioned above, although 53 years have passed after the publication of the above-mentioned patent document 5, the relevant papers or patent documents on the method for preparing isocyanates by using carbonyl halides are mainly concentrated and limited to utilizing phosgene and In terms of the reaction of organic amines, it can also be understood that there is no technical research on carbonyl fluoride

Method used

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  • Method for producing isocyanate compound
  • Method for producing isocyanate compound
  • Method for producing isocyanate compound

Examples

Experimental program
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Effect test

Embodiment 1

[0099] The synthesis of embodiment 1 toluene di(carbamoyl fluoride)

[0100] 1 g of 2,4-toluenediamine and COF 2 5g in chlorobenzene, stirring at room temperature, the resulting product precipitated out. This was filtered to give 1.6 g of solid product. Determination of the resulting product 1 H-, 19 F-NMR, and IR spectrum confirmed that 2,4-toluene di(carbamoyl fluoride) (2,4-(FCONH) 2 C 6 h 3 CH 3 ).

[0101] 1 H-NMR (DMF-d 7 , TMS): δ2.3 (s, 3H), 7.2-7.8 (m, 3H), 10.0 (br, 1H), 10.7 (br, 1H)

[0102] 19 F-NMR (DMF-d 7 , CFCl3): φ6.9 (s, 1F), 10.3 (s, 1F)

[0103] IR: 3289, 1808, 1797, 1770, 1550cm-1

Embodiment 2

[0104] The synthesis of embodiment 2 diphenylmethane two (carbamoyl fluorides)

[0105] 1 g of 4,4'-diphenylmethanediamine and COF 2 3.5 g was dissolved in chlorobenzene, stirred at room temperature, and the resulting product precipitated out. It was filtered to obtain 1.0 g of solid product. Determination of the resulting product 1 H-, 19 F-NMR, and IR spectra confirmed the formation of 4,4'-diphenylmethane bis(carbamoyl fluoride) (4,4'-FCONHC 6 h 4 CH 2 C 6 h 4 NHCFO).

[0106] 1 H-NMR (CDCl 3 , TMS): δ3.9 (s, 2H), 6.7 (br, 2H), 7.2 (m, 4H), 7.3 (m, 4H)

[0107] 19 F-NMR (CDCl 3 , CFCl3): φ6.8 (s, 1F)

[0108] IR: 3325, 1815, 1777, 1527cm-1

Embodiment 3

[0109] Embodiment 3 adopts one-step method to synthesize TDI

[0110] 1 g of 2,4-toluenediamine and COF 2 5 g was reacted in chlorobenzene with stirring at 150° C., and then the resulting product was analyzed using a gas chromatograph. Compared with commercially available samples, it was confirmed that 2,4-toluene diisocyanate (2,4-(NCO) 2 C 6 h 3 CH 3 ).

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Abstract

Disclosed is a method for efficiently producing an isocyanate compound at a low reaction temperature at a low reaction pressure without using a highly toxic phosgene and without going through a complicated process. Specifically, an isocyanate compound is produced by reacting a carbonyl fluoride and an organic amine. A carbamoyl fluoride is produced by reacting the carbonyl fluoride and the organic amine, and then the carbamoyl fluoride is converted into an isocyanate. The carbamoyl fluoride is converted into the isocyanate by heating.

Description

technical field [0001] The present invention relates to novel processes for the preparation of isocyanate compounds. Background technique [0002] Isocyanate compounds are the main raw materials of polyurethane used as rigid and flexible foams, and are also widely used as raw materials for the production of elastomers, fibers, and synthetic leather. [0003] Typical industrially produced isocyanate compounds include toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), hexamethylene diisocyanate (HDI), and the like. [0004] These isocyanates such as TDI are mainly prepared by reacting corresponding organic amines with phosgene. Through organic amines (RNH 2 ) and phosgene (COCl 2 ) reaction to produce isocyanate is well known, by only mixing organic amine and phosgene and heating, isocyanate can be obtained, but as can be seen from the following reaction formula, the side reaction of this isocyanate reacting with raw material amine to generate urea will occur ...

Claims

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Application Information

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IPC IPC(8): C07C263/10C07C263/04C07C265/14C07C271/04
CPCC07C263/10
Inventor 权恒道田村正则关屋章
Owner NAT INST OF ADVANCED IND SCI & TECH
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