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Method for synthesizing 3-methyl-3-butenyl-1-ol by two-step process

A technology of methyl and butene, applied in chemical instruments and methods, preparation of organic compounds, preparation of oxygen-containing compounds, etc., can solve problems such as high reaction temperature and pressure, large amount of catalyst and organic solvent, excessive isobutene, etc. Achieve the effect of reducing energy consumption and material consumption of separation, reducing the difficulty of separation and processing, and reducing loss

Inactive Publication Date: 2013-07-31
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction pressure is as high as 9-15 MPa, which requires high equipment materials, which increases equipment investment costs and production risks.
[0006] In summary, the method of directly synthesizing 3-methyl-3-buten-1-ol by using isobutene and formaldehyde has the disadvantages of high reaction temperature and pressure, large amount of catalyst and organic solvent, and large excess of isobutene.

Method used

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  • Method for synthesizing 3-methyl-3-butenyl-1-ol by two-step process
  • Method for synthesizing 3-methyl-3-butenyl-1-ol by two-step process
  • Method for synthesizing 3-methyl-3-butenyl-1-ol by two-step process

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Add 805g of formic acid, 210g of paraformaldehyde and 1372g of isobutene into a 5L high-pressure stirred tank, control the reaction temperature at 130°C, and the reaction pressure at 1.5MPa. After 4 hours of reaction, 3-methyl-3-butene-1 -Alcohol formate yield is 94.6%.

[0037]The esterification reaction solution was rectified under reduced pressure to obtain 758.7 g of 3-methyl-3-buten-1-ol formate with a mass fraction of 99.5%. Add the obtained 3-methyl-3-buten-1-ol formate into a 5L stirred tank reactor, add 1942.4g of NaOH solution with a mass fraction of 15wt%, and react at 50°C for 0.8h to obtain water The phase was 2127.9g, and the weight of 3-methyl-3-buten-1-ol in the oil phase was 558.7g by internal standard method analysis, and the hydrolysis yield was 98.1%. The overall yield of 3-methyl-3-buten-1-ol was 93.0%.

Embodiment 2

[0039] Add 840g of acetic acid, 210g of paraformaldehyde and 1960g of isobutene into a 5L high-pressure stirred tank, control the reaction temperature at 120°C, and the reaction pressure at 1.2MPa. After 8 hours of reaction, 3-methyl-3-butene -1-ol acetate yield was 90.7%.

[0040] The esterification reaction solution was rectified under reduced pressure to obtain 816.8 g of 3-methyl-3-buten-1-ol acetate with a mass fraction of 99.5%. Add the obtained 3-methyl-3-buten-1-ol acetate into a 5L stirred tank reactor, add 666.6g of NaOH solution with a mass fraction of 40wt%, and react at 60°C for 0.5h to obtain water The phase is 844.4g, and the weight of 3-methyl-3-buten-1-ol in the oil phase is 526.4g by internal standard method analysis, and the hydrolysis yield is 96.4%. The overall yield of 3-methyl-3-buten-1-ol was 87.4%.

Embodiment 3

[0042] Add 2072g of propionic acid, 210g of paraformaldehyde and 1568g of isobutene into a 5L high-pressure stirred tank, control the reaction temperature at 190°C, and the reaction pressure at 4MPa. After 1 hour of reaction, 3-methyl-3-butene -1-ol propionate yield was 93.1%.

[0043] The esterification reaction solution was rectified under reduced pressure to obtain 930.1 g of 3-methyl-3-buten-1-ol propionate with a mass fraction of 99.5%. Add the obtained 3-methyl-3-buten-1-ol propionate into a 5L stirred tank reactor, add 2606.8g of NaOH solution with a mass fraction of 10wt%, and react at 100°C for 0.1h to obtain water The phase is 2971.8g, and the weight of 3-methyl-3-buten-1-ol in the oil phase is 508.3g by internal standard method analysis, and the hydrolysis yield is 90.7%. The overall yield of 3-methyl-3-buten-1-ol was 84.4%.

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Abstract

The invention belongs to the field of synthesis of organic compounds, and relates to a method for synthesizing 3-methyl-3-butenyl-1-ol by a two-step process. The method comprises the following steps: carrying out condensation and esterification reaction on carboxylic acid, isobutylene and formaldehyde in a high-pressure reaction kettle to generate methyl-3-butenyl-1-ol carboxylate; rectifying the condensation and esterification reaction solution in vacuum to obtain 3-methyl-3-butenyl-ol carboxylate, and carrying out hydrolysis reaction; after the hydrolysis reaction finishes, standing to stratify, wherein the organic phase contains rich 3-methyl-3-butenyl-1-ol, and the water phase contains carboxylate; and adding solid alkali with the same metallic ion as the carboxylate into the water phase, wherein after the carboxylate precipitates, the water phase containing alkali is circulated in the hydrolysis reaction of the 3-methyl-3-butenyl-1-ol carboxylate, and the insufficient water can be supplemented. The method for producing 3-methyl-3-butenyl-1-ol does not any catalyst, has the advantages of high conversion rate of raw materials, high product selectivity and high product yield, and can lower the energy consumption and material consumption for separation.

Description

technical field [0001] The invention relates to the synthesis of organic compounds, in particular to a two-step method for synthesizing 3-methyl-3-buten-1-ol. Background technique [0002] 3-Methyl-3-buten-1-ol can be used in the synthesis of pyrethroid insecticides and the production of polycarboxylate cement superplasticizers, and is an important organic synthesis intermediate. [0003] At present, the method for synthesizing 3-methyl-3-buten-1-ol is mainly obtained by Prins addition reaction using paraformaldehyde and isobutylene as raw materials. As U.S. Patent [US4028424,1977-6-7] reported the method that isobutylene and paraformaldehyde Prins addition reaction generates 3-methyl-3-butene-1-alcohol, this method uses phosphate and its derivatives as Catalyst, the amount of catalyst is 2.5% of the mass of paraformaldehyde added; with tert-butanol or ethyl acetate as solvent, the mass of tert-butanol added is more than 13 times the mass of paraformaldehyde added; the reac...

Claims

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Application Information

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IPC IPC(8): C07C33/025C07C27/02
Inventor 乔旭陈献刘清周哲费兆阳崔咪芬汤吉海
Owner NANJING UNIV OF TECH
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