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Preparation method of 3, 3-dimethyl-1-butyne

A technology of dimethyl and butyne, applied in the field of preparation of 3,3-dimethyl-1-butyne, achieves the effects of high yield, mild reaction conditions and short synthesis route

Active Publication Date: 2021-04-16
SHANDONG BOYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the presence of 70% sulfuric acid, acetylene is passed through tert-butanol to obtain 3,3-dimethyl-1-butyne, but it is reported in the literature that although the conversion rate of tert-butanol can reach 42%, the main product is di Isobutene, 3,3-dimethyl-1-butene in only 2.1% yield

Method used

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  • Preparation method of 3, 3-dimethyl-1-butyne

Examples

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example 1

[0028] Example 1: Preparation of 3,3-dimethyl-1-butyne

[0029] Using tert-butanol and acetylene as starting materials, and using transition metal salts readily available in the market as catalysts, the product is directly reacted in the presence of acid to obtain a high-purity product, which is separated by simple distillation. The synthetic route is as follows:

[0030]

[0031] 1000ml (10.5mol) tert-butanol, 4.7g (0.018mol) nickel sulfate hexahydrate, 0.6g (0.003mol) palladium sulfate, 101g (1.05mol) methanesulfonic acid, 9g (0.5mol) deionized water, lower the temperature to -5~5°C, first replace the air in the kettle with nitrogen, then pass the acetylene gas through 40% sodium hydroxide solution, concentrated sulfuric acid solution and anhydrous calcium chloride desiccant, Put into the reactor to replace the gas in the reactor for 3 times, flow acetylene to 0.5MP, keep the temperature in the reactor at 0°C and react for 3 hours until the acetylene is no longer washed, ...

example 2

[0032] Example 2: Recycling of residues in the preparation of 3,3-dimethyl-1-butyne

[0033] Keep the distillation residue of Example 1 at an external temperature of 80°C, and distill under reduced pressure at -0.09Mp until no fractions are evaporated to obtain a total of 122.5g brownish-red solid-liquid mixture. This mixture is rinsed with 1000ml tert-butanol into a 2L liner IV In the fluorine autoclave, no further catalyst, methanesulfonic acid and water were added, and acetylene was reacted as in Example 1 to obtain a total of 781.2g colorless liquid with a yield of 90.7% and a product purity of 99.4% (GC method).

example 3

[0034] Example 3: Preparation of 3,3-dimethyl-1-butyne

[0035] 1000ml (10.5mol) tert-butanol, 7.2g (0.018mol) iron sulfate, 0.6g (0.003mol) palladium sulfate, 101g (1.05mol) methanesulfonic acid, 9g (0.5 mol) deionized water, lower the temperature to -5~5°C, first replace the air in the kettle with nitrogen, then pass the acetylene gas through 40% sodium hydroxide solution, concentrated sulfuric acid solution and anhydrous calcium chloride desiccant respectively, and pass into the reaction Replace the gas in the kettle for 3 times, pass acetylene to 0.5MP, keep the temperature in the kettle at 0°C and react for 3 hours until the acetylene is no longer washed, replace the gas in the kettle with nitrogen, exhaust the gas, and detect the content of tert-butanol in the reaction solution by GC ≤ 2% , transfer the material to a 2L four-necked bottle, distill at normal pressure, remove the previous fraction, collect the fraction at 37-40°C to obtain 553.3g of colorless liquid, which...

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Abstract

The invention discloses a preparation method of 3, 3-dimethyl-1-butyne, which comprises the following steps: by using tert-butyl alcohol and acetylene which are simple, readily available and cheap as initial raw materials and using transition metal salt which is readily available on the market as a catalyst, directly reacting in the presence of acid to obtain a product, and carrying out simple distillation separation to obtain a high-purity product. The method is simple and convenient to operate, less in environmental pollution, good in product quality, high in yield, low in cost and more suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 3,3-dimethyl-1-butyne, which belongs to the field of chemical synthesis. Background technique [0002] Terbinafine hydrochloride is an allylamine antifungal drug with broad-spectrum antifungal activity and strong antibacterial effect. Dermatomycosis especially onychomycosis. Terbinafine is currently the only antifungal drug that can be used externally and orally. It has effects on most pathogenic fungi, and the most sensitive ones are dermatophytes. [0003] 3,3-Dimethyl-1-butyne is an important intermediate of the antifungal drug terbinafine hydrochloride. The English name is 3,3-Dimethyl-1-butyne, the CAS number is 917-92-0, and the molecular formula is C 6 h 10 , the molecular weight is 82.14, and the structural formula is: [0004] [0005] The synthetic process of 3,3-dimethyl-1-butyne reported in the literature mainly contains the following types: [0006] Hsing-Pang Hsieh et al. reported ...

Claims

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Application Information

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IPC IPC(8): C07C1/24C07C11/22
Inventor 李太同朱义胜尚林峰昝金行
Owner SHANDONG BOYUAN PHARM CO LTD
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