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Process for preparing sulfidomethyl phenol derivatives

A technology of alkyl and formaldehyde, applied in the field of antioxidant preparation, can solve the problems of easy volatility and difficult separation of dibutylamine, and achieve the effects of easy separation and high yield

Inactive Publication Date: 2007-07-04
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In U.S. Patent No. 4,623,745, dibutylamine is used as a catalyst, and phenol, formaldehyde and mercaptan are reacted in one step to synthesize 2,6-di-tert-butyl-4-ester-based thiomethylphenol, but dibutylamine is difficult to separate from the product
In U.S. Patent No. 5,427,701, dimethylamine gas or its ethanol solution is used as a catalyst, and phenol, formaldehyde and mercaptan are reacted in one step to synthesize sulfur methylphenol derivatives, but dimethylamine gas or its ethanol solution is extremely volatile, and the reaction requires Pressure device

Method used

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  • Process for preparing sulfidomethyl phenol derivatives
  • Process for preparing sulfidomethyl phenol derivatives
  • Process for preparing sulfidomethyl phenol derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: 2, the synthesis of 6-di-tert-butyl-4-((n-dodecylsulfanyl) methyl) phenol

[0023] In a 150mL three-necked flask equipped with mechanical stirring and a reflux condenser, add 20.6g (0.1mol) 2,6-di-tert-butylphenol, 4.5g (0.15mol) paraformaldehyde (relative molecular mass 240) and 20.2g (0.1mol) dodecyl mercaptan, 15g following silica-supported catalyst (Cat.) 1 (that is R in above-mentioned formula (2) 5 =O 3 Si(CH 2 ) 3 , R 6 =H)

[0024]

[0025] and 15mL of N,N-dimethylformamide, heated to 120°C, reacted for 3 hours, cooled, filtered, washed with water, and dried to obtain 41.2g of light yellow liquid with a yield of 98%. It is confirmed by analysis that the product is a compound of formula (1), wherein R 1 , R 2 For tert-butyl, respectively located in the ortho position of -OH, R 3 For n-dodecyl, -CH 2 SR 3 Located in the para position of -OH.1 HNMR analysis result shows that purity > 98%, analysis data is as follows:

[0026] 1 HNMR (CD...

Embodiment 2

[0027] Embodiment 2: the synthesis of 2-(2-hydroxyethylthio)methylphenol

[0028] In a 150mL three-necked flask equipped with mechanical stirring and a reflux condenser, add 9.4g (0.1mol) of phenol, 4.5g (0.15mol) of paraformaldehyde (relative molecular mass 240) and 7.8g (0.1mol) of mercaptoethanol , and 10 g of silica-supported catalyst 1 (that is, R in the above formula (2) 5 =O 3 Si(CH 2 ) 3 ,R 6 =H), 12g (0.1mol), and 15mL of N,N-dimethylformamide, heated to 155°C, reacted for 1 hour, cooled, filtered, washed with water, and dried to obtain 41.2g of light yellow liquid with a yield of 98% . It is confirmed by analysis that the product is a compound of formula (1), wherein R 1 ,R 2 is H, located at the ortho and para positions of -OH, R 3 for -CH 2 CH 2 OH, -CH 2 SR 3 Ortho to -OH. The analysis data is as follows:

[0029] 1 HNMR (CDCl 3 ): 7.25-7.10 (m, 2H, C 6 H 4 ), 6.85-6.70 (m, 2H, C 6 H 4 ), 6.65-6.00 (br, 1H, Ph-O H ), 3.90 (s, 2H, PhC H 2 S...

Embodiment 3

[0030] Example 3: Synthesis of 2,6-di-tert-butyl-4-((n-dodecylthio)methyl)phenol

[0031] In a 150mL three-necked flask equipped with mechanical stirring and a reflux condenser, add 20.6g (0.1mol) 2,6-di-tert-butylphenol, 4.5g (0.15mol) paraformaldehyde, 20.2g (0.1mol) Dodecyl mercaptan, 8g following catalyst 2 supported by polystyrene (i.e. R in the formula (2) 5 CH 2 ,R 6 =H)

[0032]

[0033] Replacing the catalyst supported by silica (1) Other conditions are the same as in Example 1. Heated to 120° C., reacted for 3 hours, cooled, filtered, washed with water, and dried to obtain 39.8 g of light yellow liquid. The product was the same as in Example 1, with a yield of 94.7%.

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Abstract

The invention relates to a method for preparing sulfur methyl phenol derivative which is shown in formula (1). The inventin is characterized in that it takes compound in formula (2) and (3) as catalyst, and proceeds reaction with phenol, formaldehyde and thiols compounds under 50- 250 Deg. C; the carrier in compound of formula (2) is inorganic compound or organic ploymer, R5 is alkyl of direct or branch chain for C1-C8, substituent with benzene ring or alkyl of direct or branch chain containing N, O and / or Si and other atoms; R6 is H or alkyl of direct or branch chain for C1-C8 or alkyl of direct or branch chain containing N, O and / or Si and other atoms or miscellaneous naphthenic base; the carrier in compound of formula (3) is inorganic matter or organic polymer, said R7 and R8 are alkyl of direct or branch chain for C1-C12 respectivly, and R7 and R8 can also be different.

Description

technical field [0001] The invention relates to a preparation method of an antioxidant, in particular to a preparation method of thiomethylphenol derivatives. Background technique [0002] It is well known that adding a small amount of antioxidants to polymers can prevent or impede the degradation of polymers and improve the service life of polymers. Thiomethylphenol derivatives are a class of high-efficiency antioxidants with self-synergistic effects. In 1989, Massy, ​​D.J.R. used p-toluenesulfonic acid as a catalyst to synthesize thiomethylphenol derivatives by reacting hydroxymethylphenol with mercaptan, with a total yield of 37.8%. In U.S. Patent No. 3,553,270, a strong base such as sodium hydroxide is used as a catalyst, and phenol, formaldehyde, and mercaptan are reacted in one step to synthesize thiomethylphenol derivatives, and the reaction yield is less than 10%. In U.S. Patent No. 3,832,328, Mannich base is used as a raw material to eliminate volatile amines by h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C321/12C07C321/20B01J31/02
Inventor 刘鹏陈鸣才张怀平祝纶宇许凯何涛
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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