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A kind of preparation method of o-aminothiophenol

A technology of o-aminothiophenol and o-chloronitrobenzene, which is applied in the field of compound preparation, can solve the problems of many reaction by-products, low product purity, and difficulty in obtaining raw materials, and achieve less side reactions, high product yield, and mechanism clear effect

Active Publication Date: 2021-02-26
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, the demand for o-aminothiophenol in the electronics industry has been increasing year by year, but it is difficult to supply a large amount of products with a purity greater than 99.9% in the market. Therefore, it is urgent to develop a process for preparing high-purity o-aminothiophenol
[0003] There are many synthesis methods of o-aminothiophenol at present, and these methods mainly have two major problems in terms of industrialization: one is that the raw materials are difficult to obtain and the price is high; the other is that there are many reaction by-products, the yield is low, and the product purity is low
[0005] However, the raw material benzothiazole and its derivatives are very expensive, and the market cannot supply them in large quantities, which hinders the scale and cost control of industrialization

Method used

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  • A kind of preparation method of o-aminothiophenol
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Embodiment 1

[0045] The present embodiment provides a kind of preparation method of o-aminothiophenol, and specific reaction process is as follows figure 1 shown. Specifically include the following steps.

[0046] Add o-chloronitrobenzene: 157.6g (1mol, 1.0eq) to 1000mL, 20% sodium methyl mercaptide aqueous solution: 525g (1.5mol, 1.5eq), tetrabutylammonium bromide: 9.7g (0.03mol, 0.03 eq), start stirring and heat up to 55°C, heat preservation reaction for 6 hours, the control o-chloronitrobenzene in HPLC is 0.6%, the reaction is over, cool down to 20°C, stand for 0.5 hours, and separate layers, the lower layer is o-nitrobenzyl Thioether: 164.0 g, yield: 97.1%, purity 99.3%. The proton nuclear magnetic spectrum of the o-nitroanisole sulfide of the present embodiment- 1 HNMR such as figure 2 as shown, figure 2 As can be seen 1 H NMR (500 MHz, CDCl 3 ), δ=2.52(s, 3H, CH 3 ),7.50(t,1H,A r H), 7.70-7.80 (m, 2H, A r H), 8.21(d, 1H, A r h).

[0047]In a 2000mL autoclave, add o-nitr...

Embodiment 2

[0050] This embodiment provides a preparation method of o-aminothiophenol, which specifically includes the following steps.

[0051] Add o-chloronitrobenzene: 157.6g (1mol, 1.0eq) to 1000mL, 20% sodium methyl mercaptide aqueous solution: 560g (1.6mol, 1.6eq), chain polyethylene glycol: 5.0g, start stirring and heat up to 68 ° C, heat preservation reaction for 5 hours, the control of o-chloronitrobenzene in HPLC is 0.4%, the reaction is completed, the temperature is lowered to 20 ° C, standing for 0.5 hours, and the layers are separated. The lower layer is o-nitroanisole sulfide: 162.5g, collected Yield: 96.2%, purity 99.2%.

[0052] In a 2000mL autoclave, add o-nitroanisole sulfide: 162.5g (0.96mol, 1.0eq), ethanol: 800g, Raney nickel: 1g, pass nitrogen replacement three times, then pass hydrogen replacement three times, and increase the pressure to 1.7MPa, heat up to 65°C for hydrogenation reaction, start the central control when the pressure no longer drops significantly, i...

Embodiment 3

[0055] This embodiment provides a preparation method of o-aminothiophenol, which specifically includes the following steps.

[0056] Add o-chloronitrobenzene: 157.6g (1mol, 1.0eq), 20% sodium methyl mercaptide aqueous solution: 700g (2.0mol, 2.0eq), cyclodextrin: 8.0g to 1000mL, start stirring and heat up to 70°C, Insulation reaction for 5 hours, the control of o-chloronitrobenzene in HPLC was 0.3%, the reaction was completed, the temperature was lowered to 20°C, and stood for 0.5 hours, and the layers were separated. The lower layer was o-nitroanisole sulfide: 163.3g, yield: 96.5 %, 99.5% purity.

[0057] Add o-nitroanisole sulfide: 163.3g (0.965mol, 1.0eq), methanol: 700g, platinum carbon: 1g into a 2000mL autoclave, replace with nitrogen three times, then replace with hydrogen three times, and raise the pressure to 1.5 MPa, heat up to 80°C for hydrogenation reaction, and start central control when the pressure no longer drops significantly. It takes about 5 hours to keep w...

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Abstract

The invention provides a preparation method of o-aminothiophenol. The preparation method comprises the following steps: putting o-chloronitrobenzene into sodium methyl mercaptide, and performing heating under the action of a catalyst to carry out a methyl vulcanization reaction so as to prepare o-nitrophenyl dimethyl sulfide; putting o-nitrophenyl thioether into a solvent, and carrying out hydrogenation reduction to prepare o-aminobenzene thioether; and demethylating the o-aminothiophenol under the action of hydrobromic acid to obtain the o-aminothiophenol. The preparation method of o-aminothiophenol has the advantages of high yield and high product purity.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of o-aminothiophenol, and belongs to the technical field of compound preparation. Background technique [0002] O-aminothiophenol is an important organic chemical intermediate widely used in medicine, rubber and other industries. Its appearance is needle-like crystal or light yellow liquid with a melting point of 26°C. In recent years, the demand for o-aminothiophenol in the electronics industry has been increasing year by year, but it is difficult to supply a large amount of products with a purity greater than 99.9% in the market. Therefore, it is urgent to develop a process for preparing high-purity o-aminothiophenol. [0003] At present, there are many synthesis methods of o-aminothiophenol. These methods mainly have two major problems in terms of industrialization: one is that the raw materials are difficult to obtain and the price is high; the other ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/06C07C323/34C07C319/14C07C323/09C07C319/20C07C323/36
CPCC07C319/06C07C319/14C07C319/20C07C323/09C07C323/36C07C323/34
Inventor 曾淼徐剑锋赵飞孙思沈洁
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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