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One-pot method for directly preparing thiodiglycol dimethyl acrylate

A technology of dimethacrylate and thiodiglycol, which is applied in the field of preparing thiodiglycol dimethacrylate, can solve the problems of removing quaternary ammonium salts, affecting application and the like, and achieves simple and mild reaction conditions and product yield. The effect of high, cheap and easy to obtain raw materials

Inactive Publication Date: 2012-03-21
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses quaternary ammonium salt as a phase transfer catalyst. After the reaction, the emulsification is serious, and heating or salt washing cannot completely remove the quaternary ammonium salt from the product, thereby affecting the application of the product in optical resins and heavy metal chelating resins.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 104mL (0.925 mol) of thiodiglycol into 260mL of dichloromethane, stir to dissolve, add 207g (1.5mol) of powdered potassium carbonate, stir vigorously to form a suspension, and drop into Mixed solution of methacryloyl chloride / dichloromethane, including 58mL (0.66 mol) of methacryloyl chloride and 116mL of dichloromethane, drop it in 2 hours, and continue to stir for 1 hour. Place in a centrifuge for centrifugation, 4000rpm, 15min, until potassium chloride and unreacted potassium carbonate are completely removed, the supernatant is washed 2 to 3 times, dried with calcium chloride, and the solvent is evaporated under reduced pressure to obtain Color transparent liquid 137.5g. Yield 89.3%, refractive index =1.4920, Abbe value =54.8, IR(NaCl): 1719(COO), 1637(C=C), 3105(=CH 2 ), 1377 (CH 3 ). 1 H NMR (CDCl 3 ): δ1.95(s, 6H), 2.86(tri, 4H), 4.33(tri, 4H), 5.59(s, 2H), 6.10(s, 2H).

Embodiment 2

[0016] Add 156mL of thiodiglycol into 468mL of dichloromethane, stir to dissolve, add 207g of powdered potassium carbonate, stir vigorously to form a suspension, add methacryloyl chloride / dichloromethane dropwise in an ice-water bath at 4-8°C The mixed solution, including 102 mL of methacryloyl chloride and 306 mL of dichloromethane, was dripped in 1.5 hours and continued to stir for 0.5 hours. Place in a centrifuge for centrifugation, 4000rpm, 15min, until potassium chloride and unreacted potassium carbonate are completely removed, the supernatant is washed 2 to 3 times, dried with calcium chloride, and the solvent is evaporated under reduced pressure to obtain Color transparent liquid 238.9g. Yield 88.0%, refractive index =1.4920, Abbe value =54.7, the result of product structure proof is the same as embodiment 1.

Embodiment 3

[0018] Add 10.4 L of thiodiglycol into 26.0 L of dichloromethane, stir to dissolve, add 20.7 kg of powdered potassium carbonate, stir vigorously to form a suspension, drop in methacryloyl chloride / The dichloromethane mixed solution, including 5.8 L of methacryloyl chloride and 11.6 L of dichloromethane, was dripped in 2 hours and continued to stir for 1 hour. Centrifuge in a centrifuge, 4000rpm, 15min, until KCl and unreacted potassium carbonate are completely removed, wash the supernatant with water 2 to 3 times, dry with calcium chloride, evaporate the solvent under reduced pressure, and obtain colorless and transparent Liquid 13.96kg. Yield 90.6%, refractive index =1.4921, Abbe value =54.8, the result of product structure proof is the same as embodiment 1.

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Abstract

A one-pot method for directly preparing thiodiglycol dimethyl acrylate belongs to the technical field of optical resin synthesis and includes steps of adding thiodiglycol into dichloromethane for mixing and dissolving, adding powdery potassium carbonate for intense mixing to generate turbid liquid, dropping methacryloyl chloride / dichloromethane mixed liquor by means of an ice-water bath method, placing reaction liquid into a centrifuge for centrifugal separation after reaction is completed until complete removing of potassium chloride and unreacted potassium carbonate, supernatant is washed for two to three times and dried by calcium chloride prior to steaming the solvent by means of pressure reduction, and finally obtaining colorless and clear liquid, namely thiodiglycol dimethyl acrylate products. The one-pot method for directly preparing thiodiglycol dimethyl acrylate is low-cost and easily obtainable in raw materials, simple and mild in reaction condition, convenient and safe in operation, simple in after-treatment, high in product yield and suitable for industrialized production, high in product purity, colorless, clear and capable of being used for radical polymerization caused by photo initiation and preparing optical resin with high refractive index. The one-pot method for directly preparing thiodiglycol dimethyl acrylate has higher implementation value and potential social and economic benefits.

Description

technical field [0001] The invention relates to a method for preparing thiodiethylene glycol dimethacrylate, in particular to a method for directly preparing thiodiethylene glycol dimethacrylate in a one-pot method using methacryloyl chloride and thiodiglycol as raw materials The method belongs to the technical field of optical resin synthesis. Background technique [0002] Optical resin has been widely used instead of optical glass in many fields such as spectacle lenses, building materials, and optical lenses due to its light weight, impact resistance, low price, and easy processing and molding. Sulfur-diethylene glycol dimethacrylate, a sulfur-containing unsaturated monomer, can be polymerized by free radicals to obtain sulfur-containing optical resins. This sulfur-containing optical resin has the advantages of high refractive index, low dispersion, and small specific gravity. , especially the thermo-light stability is significantly better than that of halogen-containing...

Claims

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Application Information

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IPC IPC(8): C07C323/12C07C319/20
Inventor 邹路易顾文秀
Owner JIANGNAN UNIV
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