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Preparation method of phenyl isothiocyanate

A technology of phenyl isothiocyanate and ethyl acetate, which is applied in the field of preparation of phenyl isothiocyanate, can solve the problems of serious environmental pollution, cumbersome post-processing, and difficult operation, and achieve simple equipment and short reaction time Short, easy-to-use effects

Inactive Publication Date: 2013-05-08
ANHUI UNIVERSITY OF TECHNOLOGY AND SCIENCE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, the preparation method of phenyl isothiocyanate uses highly toxic thiophosgene, acyl chloride, acid anhydride or other highly corrosive raw materials to decompose the dithiocarbamate produced in the reaction process, and all of them are in the organic It is carried out in a solvent, the post-processing is cumbersome, and the environmental pollution is serious
In the prior art, a relatively environmentally friendly method is to prepare sodium carbadithiocarbamate by addition of amine and carbon disulfide under the action of a strong base in an organic solvent, then react with chloroformate, and then hydrolyze with caustic soda solution and Steam distillation, removal of alcohol and thiocarbonic acid to achieve, the steps are cumbersome and difficult to operate
So far no one-step direct preparation of phenylisothiocyanate by mechanochemical solvent-free technique has been reported

Method used

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  • Preparation method of phenyl isothiocyanate
  • Preparation method of phenyl isothiocyanate
  • Preparation method of phenyl isothiocyanate

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Weigh 1.23g of p-methoxyaniline, 2.28g of carbon disulfide and 0.56g of potassium hydroxide, place in a 25mL mechanochemical reaction tank, feed in parallel to another same mechanochemical reaction tank, and fix it after tightening the seal. On the swing arm of the German Leisch Mechanochemical Reactor (MM400). React for 40 minutes at an oscillation frequency of 30 Hz. After the reaction was completed, the reaction mixture of the two tanks was extracted with ethyl acetate / water, and the ethyl acetate phase was collected in combination, dried over anhydrous magnesium sulfate and filtered, and the filtrate was evaporated to dryness and separated by silica gel column chromatography (eluent: V Petroleum ether / V ethyl acetate=8:1) to obtain 1.55 g of pure p-methoxyphenyl isothiocyanate in the form of a white slightly yellow solid with a yield of 94%.

Embodiment 2-9

[0034] Adopt aniline or different substituted anilines to prepare phenyl isothiocyanate, experimental operation is the same as embodiment 1, and the results are shown in Table 1.

[0035] Table 1 is the phenyl isothiocyanate prepared by aniline or different substituted anilines as raw materials

[0036]

[0037] Table 1

[0038] The product nuclear magnetic resonance spectrogram of embodiment 1-6 (wherein resonant frequency is 300Hz, solvent used is CDCl 3 ) analysis results are as follows:

[0039] Product 1: p-methoxyphenylisothiocyanate

[0040] 1 HNMR: 7.16 (d, J = 8.6 Hz, 2H, ArH), 6.85 (d, J = 8.6 Hz, 2H, ArH), 3.80 (s, 3H, OCH 3 ); 13 CNMR: 158.6, 133.9 (NCS), 127.0, 123.5, 114.8, 55.6 (OCH 3 ).

[0041] Product 2: phenylisothiocyanate

[0042] 1 HNMR: 7.15–7.31 (m, 5H, ArH); 13 CNMR: 134.6 (NCS), 130.3, 128.5, 126.3, 124.7.

[0043] Product 3: o-methylphenylisothiocyanate

[0044] 1 HNMR: 7.19 (brs, 4H, ArH), 2.39 (s, 3H, CH 3 ); 13 CNMR: 134.9, 133.8...

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Abstract

The invention discloses a preparation method of phenyl isothiocyanate. The preparation method comprises the steps of: putting substituted aniline, carbon disulfide and potassium hydroxide in molar ratio of 1: (2-3):1 in a mechanical-chemical reactor for vibration and grinding, extracting, drying and filtering after reaction is ended, evaporating filtrate to dryness and then carrying out silica-gel column chromatography isolation, thus obtaining the phenyl isothiocyanate. According to the preparation method, reaction is completed in one step under the condition of inexistence of solvents, operation is simple, needed reaction time is short, and environment pollution is avoided; chloroformates or other high-corrosion raw materials with strong toxicity are not used for decomposing dithiocarbamate generated in a reaction process so that reaction is safe.

Description

technical field [0001] The invention relates to a preparation method of phenyl isothiocyanate. Background technique [0002] At present, the preparation method of phenyl isothiocyanate uses highly toxic thiophosgene, acyl chloride, acid anhydride or other highly corrosive raw materials to decompose the dithiocarbamate produced in the reaction process, and all of them are in the organic It is carried out in a solvent, and the post-processing is tedious, and the environmental pollution is serious. In the prior art, a relatively environmentally friendly method is to prepare sodium carbadithiocarbamate by addition of amine and carbon disulfide under the action of a strong base in an organic solvent, then react with chloroformate, and then hydrolyze with caustic soda solution and Steam distillation, removal of alcohol and thiocarbonic acid to achieve, the steps are cumbersome and difficult to operate. So far, no one-step direct preparation of phenylisothiocyanate by mechanochem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C331/28
Inventor 张泽吴浩浩
Owner ANHUI UNIVERSITY OF TECHNOLOGY AND SCIENCE
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