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Synthetic method of p-acetoxystyrene

A technology of acetoxystyrene and acetoxybenzene, which is applied in the field of new preparation of p-acetoxystyrene, can solve the problems of large amount of wastewater that is difficult to treat, and achieve good application value, less three wastes and high yield Effect

Pending Publication Date: 2020-05-01
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of the intermediate p-acetoxystyrene is catalyzed by a strong base, and the amount of waste water is large and difficult to treat.

Method used

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  • Synthetic method of p-acetoxystyrene
  • Synthetic method of p-acetoxystyrene
  • Synthetic method of p-acetoxystyrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In a three-necked flask, add 5.0g (0.028mol) of p-acetoxyphenylethanol, 5.0g of Hβ molecular sieve catalyst, 100mL of toluene and 0.05g of tert-butylcatechol, stir and react at 90 °C for 30 minutes, filter off the catalyst etc., spin-dried toluene, and rectified under reduced pressure to obtain 3.52 g of p-acetoxystyrene, and the yield was 78%. 1 H NMR (600 MHz, CDCl 3 ) δ7.51-7.43 (m, 2H), 7.16-7.07 (m, 2H), 6.82-6.68 (m, 1H), 5.76 (dd, J = 17.7,2.7 Hz, 1H), 5.29 (dd, J = 11.2, 2.6 Hz, 1H), 2.31 (s, 3H).

Embodiment 2

[0026] In a three-necked flask, add 5.0 g (0.028 mol) of p-acetoxyphenethyl alcohol, 5.0 g of H-ZSM-5 molecular sieve catalyst, 100 mL of toluene and 0.03 g of tert-butylcatechol, and stir the reaction at 90 °C for 30 Minutes, the catalyst was filtered off, the toluene was spin-dried, and rectified under reduced pressure to obtain 3.25 g of p-acetoxystyrene, with a yield of 72%.

Embodiment 3

[0028] In a three-necked flask, add 5.0 g (0.028 mol) of p-acetoxyphenethyl alcohol, 5.0 g of acidic alumina, and 100 mL of toluene, stir and react at 90 °C for 30 minutes, filter out the catalyst, spin dry the toluene, and purify under reduced pressure. Distillation gave 2.5 g of p-acetoxystyrene, and the yield was 55%.

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Abstract

The invention relates to a synthetic method of p-acetoxystyrene, in particular to a novel process for synthesizing p-acetoxystyrene serving as an intermediate of 248-nm photoresist monomer p-hydroxystyrene. The method comprises the following steps of: performing solid acid catalysis on p-hydroxyphenethyl alcohol serving as a raw material, and performing dehydrating in an organic solvent in the presence of a polymerization inhibitor to obtain a target product. According to the synthetic method of p-acetoxystyrene, the p-hydroxyphenethyl alcohol is taken as the raw material for solid acid catalysis to prepare the 248-nm photoresist monomer p-hydroxystyrene intermediate p-acetoxystyrene through one-pot boiling, and the new synthesis process has the advantages that the yield is high, a catalyst is easy to recycle and reuse, few three wastes are generated and the like.

Description

technical field [0001] The invention relates to a synthesis method of p-acetoxystyrene, in particular to a new preparation method of p-acetoxystyrene for preparing 248nm photoresist monomer. Background technique [0002] Photoresist, also known as photoresist, refers to a corrosion-resistant film material whose solubility changes through irradiation or radiation of ultraviolet light, electron beams, particle beams, X-rays, etc. Photoresist is the key material to complete the photolithography process in microelectronics manufacturing, and it determines the development level of microelectronics technology. [0003] In 1984, IBM discovered that the use of photoacid generators can remove the hydrophobic protective group of the polymer chain and decompose it, making it soluble in alkaline water, greatly improving the light efficiency and obtaining a photoresist with a smaller line width, namely For deep ultraviolet photoresist. 248nm photoresist belongs to deep ultraviolet phot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/297C07C69/157
CPCC07C67/297C07C69/157Y02P20/584
Inventor 蒋绍亮范跃镔韩亮张蓉娟
Owner ZHEJIANG UNIV OF TECH
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