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Synthesis method for p-tert-butylcatechol

A technology of p-tert-butylcatechol and tert-butylcatechol, which is applied in the field of organic synthesis and can solve the problems of waste water, waste salt pollution, high reaction temperature requirements, and non-reusable catalysts.

Active Publication Date: 2019-07-23
江西兄弟医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current synthesis of 4-TBC is catalyzed by conventional liquid acid or sulfonic acid ion exchange resin or solid acid, which requires high reaction temperature, high equipment material requirements, serious corrosion, and the generated waste water and waste salt pollute the environment. The catalyst cannot be repeated. Utilizing the technical defects of low yield and selectivity, the present invention provides a synthetic method for p-tert-butylcatechol, which can carry out transposition repositioning of 3-TBC and 3,5-DTBC under the action of HMT catalyst. Exhaust reaction to generate 4-TBC, which can directly improve the selectivity of the reaction, and is a green synthesis method of p-tert-butylcatechol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] A kind of synthetic method of p-tert-butylcatechol, concrete steps are:

[0016] 1. Preparation of HMT catalyst: 500g of carbon tetrachloride as co-solvent, 250g of p-styrenesulfonic acid, 50g of divinylbenzene and 5g of piperazine, stirred at 75°C for 8h, then cooled to room temperature, and filtered to remove carbon tetrachloride solvent, and dried to obtain solid HMT catalyst particles.

[0017] 2. Synthesis of p-tert-butylcatechol:

[0018] Add 550g (4.95mol) of catechol and 13.7g of HMT catalyst into a 2L stainless steel high-pressure reactor equipped with mechanical stirring, heat transfer oil jacket temperature control, air duct, digital display pressure gauge, and isobutylene gas flowmeter, and seal it. Add N with stirring 2 Drive out the air. When the temperature rises to 105°C, isobutene can be fed in at a constant flow rate, and the reaction pressure is controlled at 0 to 0.5 bar. About 138.0 g (2.43 mol, purity >99%) of isobutene is fed in 7 hours, and th...

Embodiment 2

[0020] A kind of synthetic method of p-tert-butylcatechol, concrete steps are:

[0021] 1. Preparation of HMT catalyst: 500g of carbon tetrachloride as co-solvent, 250g of p-styrenesulfonic acid, 50g of divinylbenzene and 5g of piperazine, stirred at 75°C for 8h, then cooled to room temperature, and filtered to remove carbon tetrachloride solvent, and dried to obtain solid HMT catalyst particles.

[0022] 2. Synthesis of p-tert-butylcatechol:

[0023] Add 550g (4.95mol) of catechol and 13.7g of HMT catalyst into a 2L stainless steel high-pressure reactor equipped with mechanical stirring, heat transfer oil jacket temperature control, air duct, digital display pressure gauge, and isobutylene gas flowmeter, and seal it. Add N with stirring 2 Drive out the air. When the temperature rises to 105°C, isobutene can be fed in at a constant flow rate, and the reaction pressure is controlled at 0-0.5 bar. About 143.4g (2.53mol, purity >99%) of isobutene is fed in 7 hours, and the rea...

Embodiment 3

[0025] A kind of synthetic method of p-tert-butylcatechol, concrete steps are:

[0026] 1. Preparation of HMT catalyst: 500g of carbon tetrachloride as co-solvent, 250g of p-styrenesulfonic acid, 50g of divinylbenzene and 5g of piperazine, stirred at 75°C for 8h, then cooled to room temperature, and filtered to remove carbon tetrachloride solvent, and dried to obtain solid HMT catalyst particles.

[0027] 2. Synthesis of p-tert-butylcatechol:

[0028] Add 550g (4.95mol) of catechol and 13.7g of HMT catalyst into a 2L stainless steel high-pressure reactor equipped with mechanical stirring, heat transfer oil jacket temperature control, air duct, digital display pressure gauge, and isobutylene gas flowmeter, and seal it. Add N with stirring 2 Drive out the air. When the temperature rises to 105°C, isobutene can be fed in at a constant flow rate, and the reaction pressure is controlled at 0-0.5 bar. About 144.6g (2.55mol, purity >99%) of isobutene is fed in 7 hours, and the rea...

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PUM

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Abstract

The invention relates to a synthesis method for p-tert-butylcatechol. The method comprises the following steps that: catechol and isobutene are taken as raw materials; under the existence of an HMT (hexamine) catalyst, N2 is used for replacing air in a reaction still; after catechol is heated and dissolved, isobutene is introduced at a uniform speed at a temperature of 80-120 DEG C, wherein introduction time is controlled within 4-8 h; then, at a temperature of 105-110 DEG C, thermal insulation reaction is carried out, wherein thermal insulation reaction time is controlled within 0-5 h, and the molar ratio of catechol to isobutene is 1:(0.3-0.7); reaction liquid obtained after reaction is finished and the catalyst are subjected to filtering separation; the reaction liquid is subjected to product rectification and fractionation; the HMT catalyst is repeatedly used. According to the method, under the function of the HMT catalyst, 3-TBC (p-tert-butylcatechol) and 3,5-DTBC (3,5-di-tert-butylcatechol) can carry out transposition rearrangement reaction to generate 4-TBC, reaction selectivity can be directly improved, and the synthesis method is a green synthesis method for p-tert-butylcatechol.

Description

technical field [0001] The invention relates to a synthesis method of a high-efficiency polymerization inhibitor, in particular to a synthesis method of p-tert-butylcatechol, which belongs to the technical field of organic synthesis. Background technique [0002] 4-tert-Butylcatechol (4-TBC for short) is a white or light yellow crystal. It is mainly used as a high-efficiency polymerization inhibitor for olefin monomer distillation or storage and transportation, especially for styrene, butadiene and other ethylene monomers. Adding less than 0.001% p-tert-butylcatechol to styrene monomer at room temperature can be stored stably for 1 month. Its polymerization inhibitory effect is 25 times higher than that of hydroquinone at 60°C, and it is designated as a general-purpose polymerization inhibitor for styrene and the like by the American ASTM Association. At the same time, 4-TBC can also be used as a stabilizer for antioxidants and pesticides. [0003] At present, the traditi...

Claims

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Application Information

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IPC IPC(8): C07C37/14C07C37/00C07C39/08
CPCC07C37/14C07C37/00C07C39/08Y02P20/584
Inventor 石浒朱宇翔周中平钱志达
Owner 江西兄弟医药有限公司
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