Synthesis method of thiodiethylene bis [3-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate]

A technology of di-tert-butylphenol and di-tert-butyl, which is applied in the field of synthesis of thiodiethylenebis[3-propionate], can solve the problems of cumbersome synthesis process operation, production constraints, and low yield. Achieve the effects of simple process, high purity and high product purity

Active Publication Date: 2022-03-22
JIANGSU JIYI NEW MATERIAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, in the above method, the synthesis process of the former is cumbersome and the yield is low; while the latter not only has a low yield, but also has many impurities.
In particular, thiodiethylene glycol used in existing synthetic methods is a raw material for the synthesis of chemical weapon mustard gas, and its production and circulation are strictly regulated, resulting in thiodiethylenebis[3-(3,5-di-tert-butyl-4 -Hydroxyphenyl) propionate] production is constrained

Method used

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  • Synthesis method of thiodiethylene bis [3-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate]
  • Synthesis method of thiodiethylene bis [3-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate]
  • Synthesis method of thiodiethylene bis [3-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate]

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Under a nitrogen atmosphere, add 50 mmol (10.3 g) of 2,6-di-tert-butylphenol into the reactor, heat up to 80°C to melt, then add 5 mmol (0.56 g) of potassium tert-butoxide in 15 ml of o-di Solution in toluene; reflux for 30min, the solution gradually turns light green. The temperature of the solution was raised to 125°C, and 50 mmol (4.3 g, 4.5 ml) of methyl acrylate was slowly added dropwise, and the reaction was stirred for 2.5 h, and the solution turned into light yellow. Then the temperature was lowered to 100°C, 50mmol (4.0g, 3.4ml) of 2-chloroethanol was slowly added dropwise, stirred and reacted for 4h, then stopped. The reaction product was cooled to room temperature, washed 3 times with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain the intermediate 3-(3,5-di-tert-butyl - 14.9 g of 2-chloroethyl 4-tetrahydroxyphenyl)propanoate (yield 87.6%). ESI-MS:...

Embodiment 2

[0049] Under nitrogen atmosphere, add 50mmol (10.3g) of 2,6-di-tert-butylphenol into the reactor, heat up to 80°C to melt, then add 6mmol (0.67g) of potassium tert-butoxide in 15ml of o-di Solution in toluene; reflux for 30min, the solution gradually turns light green. The solution was warmed up to 130°C, 55mmol (4.7g, 5ml) of methyl acrylate was slowly added dropwise, and the reaction was stirred for 2h, and the solution turned into light yellow. Then the temperature was lowered to 105°C, 55mmol (4.4g, 3.7ml) of 2-chloroethanol was slowly added dropwise, stirred and reacted for 3.5h, then stopped. The reaction product was cooled to room temperature, washed 3 times with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain the intermediate 3-(3,5-di-tert-butyl - 15.3 g of 2-chloroethyl 4-tetrahydroxyphenyl)propanoate (90.2% yield).

[0050] 20mmol (6.8g) of intermediate 3...

Embodiment 3

[0052] Under a nitrogen atmosphere, add 100mmol (20.6g) of 2,6-di-tert-butylphenol into the reactor, heat up to 80°C to melt it, then add 30mmol (3.36g) of potassium tert-butoxide in 40ml of o-di Solution in toluene; reflux for 30min, the solution gradually turns light green. The solution was warmed up to 120°C, 100 mmol (8.6 g, 9.0 ml) of methyl acrylate was slowly added dropwise, and the reaction was stirred for 2 h, and the solution turned into light yellow. Then the temperature was lowered to 95°C, 100mmol (8.0g, 6.8ml) of 2-chloroethanol was slowly added dropwise, stirred and reacted for 4.5h, then stopped. The reaction product was cooled to room temperature, washed 3 times with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain the intermediate 3-(3,5-di-tert-butyl - 29.5 g of 2-chloroethyl 4-tetrahydroxyphenyl)propionate (yield 86.9%).

[0053] 60mmol (20.4g) of...

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Abstract

The invention relates to a synthesis method of thiodiethylene bis [3-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate]. The method comprises the following steps: enabling 2, 6-di-tert-butylphenol to react with acrylate, and continuing to react with 2-chloroethanol, so as to obtain an intermediate 3-(3, 5-di-tert-butyl-4-tetrahydroxyphenyl) propionic acid 2-chloroethyl ester; and reacting with sodium sulfide in the presence of quaternary ammonium salt to obtain a target product. The synthesis method disclosed by the invention has the advantages of simple process, high product yield and high purity, and is particularly suitable for being applied to industrial production.

Description

technical field [0001] The invention relates to the field of antioxidants, in particular to a synthesis method of thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate]. Background technique [0002] Thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] is a thioether-type hindered phenolic antioxidant, its molecule contains both the main antioxidant The hindered phenolic group of the agent contains the low valence sulfur (S) atom of the auxiliary antioxidant, and the structure is as follows: [0003] [0004] Thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] has high molecular weight, low migration, good thermal stability and extraction resistance; low melting point, It is easy to mix evenly with materials during processing; it also has intramolecular synergy and extramolecular synergy, so it is widely used in polymer materials such as polyethylene, polypropylene, polystyrene, ABS resin, and various synthetic rubbers. Used ...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C319/28C07C323/12C07C67/347C07C67/287C07C69/732
CPCC07C319/14C07C67/347C07C67/287C07C319/28C07C323/12C07C69/732
Inventor 郭骄阳
Owner JIANGSU JIYI NEW MATERIAL CO LTD
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