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Preparation method of 3-methyl-2-butenol

A technology of butenol and methyl, applied in the preparation of medicine and pharmaceutical intermediate 3-methyl-2-butenol, in the field of perfume, can solve the problem of accelerating catalyst system, the influence of reaction yield stability, and high synthesis cost problems, to achieve high industrial application value and environmental protection value, reduce the operation of solvent recovery and application, and improve the conversion rate and selectivity.

Active Publication Date: 2020-11-24
SHANDONG NHU PHARMA
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0006] (1) The traditional method for producing 3-methyl-2-butenol mainly takes isoprene as raw material, and obtains 3-methyl-2-butenol through chlorination, esterification and alkaline hydrolysis. Classic, esterification, alkali hydrolysis yield is high, and the reaction is easy to control, but because the yield of isoprene and hydrogen chloride reaction is about 78%, the synthesis cost of 3-methyl-2-butenol is relatively high
[0007] (2) Patent US4028424 uses isobutene and formaldehyde as raw materials to produce 3-methyl-2-butenol through condensation, but the product contains 3-methyl-2-butenol and 3-methyl-3-butenol , the content of the former only accounts for about 5%; 3-methyl-3-butenol can be further converted into 3-methyl-2-butenol, the patent US4219638 under hydrogen and palladium conditions, the conversion rate is 39%- 54%, the selectivity is 82%-99%; the patent JP08268939 uses magnesium oxide as a catalyst, and the conversion rate of 3-methyl-3-butenol into 3-methyl-2-butenol can reach 57%, The above-mentioned method for synthesizing 3-methyl-2-butenol with isobutene as a raw material has the disadvantages of harsh reaction conditions, low conversion rate, large separation difficulty and high technical requirements
[0008] (3) With 2-methyl-3-buten-2-ol as raw material, in the presence of a catalyst, it is directly converted into 3-methyl-2-butenol, which has the disadvantages of low conversion rate and poor yield
[0009] CN101381283A discloses a method for continuous production of 3-methyl-2-butenol. The catalyst system mentioned in this patent is sensitive to water, and high water content in the system will accelerate the deactivation of the catalyst system, resulting in an increase in side reactions
At the same time, the waste accumulated in the reactor and the catalyst with reduced activity need to be unloaded intermittently or continuously, and the stability of the reaction yield is affected by this

Method used

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  • Preparation method of 3-methyl-2-butenol
  • Preparation method of 3-methyl-2-butenol
  • Preparation method of 3-methyl-2-butenol

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Experimental program
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Effect test

Embodiment 1

[0033] Using a high-pressure metering pump, the mixed solution of 2-methyl-3-butene-2-ol and catalyst is pumped into the preheater at a constant rate of 25g / min, and the amount of catalyst is 2-methyl-3-butene- 0.02% of the mass of 2-alcohol, and at the same time set the temperature of the preheater to 130°C, preheat the reaction raw material 2-methyl-3-buten-2-ol and the catalyst to 130°C, and set the temperature of the tubular reactor to After the temperature of the tubular reactor is stabilized, adjust the reverse pressure controller to control the pressure at 0.6±0.01MPa, continuously feed and discharge the material, and the reaction residence time is 30min. After the reaction is completed, the reaction liquid is separated by rectification The crude product 3-methyl-2-butenol was obtained, and the reaction conversion was calculated to be 60.1%, and the selectivity was 98.5%.

[0034] The catalyst is composed of bis(triphenylphosphine)dicarbonylruthenium dichloride and tris...

Embodiment 2

[0036] Using a high-pressure metering pump, the mixed solution of 2-methyl-3-butene-2-ol and catalyst is pumped into the preheater at a constant rate of 25g / min, and the amount of catalyst is 2-methyl-3-butene- 0.02% of the mass of 2-alcohol, and at the same time set the temperature of the preheater to 120°C, preheat the reaction raw material 2-methyl-3-buten-2-ol and the catalyst to 120°C, and set the temperature of the tubular reactor to After the temperature of the tubular reactor is stabilized, adjust the reverse pressure controller to control the pressure at 0.5±0.01MPa, continuously feed and discharge the material, and the reaction residence time is 30min. After the reaction is completed, the reaction liquid is separated by rectification The crude product 3-methyl-2-butenol was obtained, and the reaction conversion rate was calculated to be 53.5%, and the selectivity was 97.5%.

[0037] The catalyst is composed of bis(triphenylphosphine)dicarbonylruthenium dichloride and...

Embodiment 3

[0039]Using a high-pressure metering pump, the mixed solution of 2-methyl-3-butene-2-ol and catalyst is pumped into the preheater at a constant rate of 25g / min, and the amount of catalyst is 2-methyl-3-butene- 0.02% of the mass of 2-alcohol, and at the same time set the temperature of the preheater to 140°C, preheat the reaction raw material 2-methyl-3-buten-2-ol and the catalyst to 140°C, and set the temperature of the tubular reactor to After the temperature of the tubular reactor is stabilized, adjust the reverse pressure controller to control the pressure at 0.8±0.01MPa, continuously feed and discharge the material, and the reaction residence time is 30min. After the reaction is completed, the reaction liquid is separated by rectification The crude product 3-methyl-2-butenol was obtained, and the reaction conversion rate was calculated to be 62.2%, and the selectivity was 94.2%.

[0040] The catalyst is composed of bis(triphenylphosphine)dicarbonylruthenium dichloride and ...

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Abstract

The invention provides a preparation method of 3-methyl-2-butenol. The preparation method comprises the following steps: carrying out an isomerization reaction on 2-methyl-3-butene-2-ol in a tubular reactor under the catalysis of a ruthenium catalyst to obtain the 3-methyl-2-butenol. No solvent is added in a reaction process, 2-methyl-3-butene-2-ol is subjected to the isomerization reaction in thetubular reactor to obtain a mixture of the 3-methyl-2-butene-2-ol and the 2-methyl-3-butene-2-ol, the mixture is rectified and separated to obtain the pure 3-methyl-2-butene-2-ol, and the 3-methyl-2-butene-2-ol obtained through recovery is returned to a reaction process, and continues to participate in the reaction. The method has the advantages of simple process flow, few side reactions, high reaction selectivity and high conversion rate.

Description

technical field [0001] The invention relates to a method for preparing perfume, medicine and medicine intermediate 3-methyl-2-butenol, which belongs to the field of fine chemical industry. Background technique [0002] 3-Methyl-2-butenol, also known as isopentenol, is an important organic intermediate; 3-methyl-2-butenol is mainly used in the production of citral, isophytol, benting Methyl chrysanthemum acid, DV methyl chrysanthemum acid, intermediates for synthesizing vitamin A and carotenoids, synthetic rubber monomers, and can also be used in other organic synthesis. [0003] The structural formula of 3-methyl-2-butenol is as follows: [0004] ; [0005] At present, 3-methyl-2-butenol mainly has the following synthetic methods: [0006] (1) The traditional method for producing 3-methyl-2-butenol mainly takes isoprene as raw material, and obtains 3-methyl-2-butenol through chlorination, esterification and alkaline hydrolysis. Classic, esterification, alkali hydrolysi...

Claims

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Application Information

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IPC IPC(8): C07C29/56C07C33/42
CPCC07C29/56C07C33/423
Inventor 方万军马啸徐家浩李聪聪樊国涛徐敏范玉雪
Owner SHANDONG NHU PHARMA
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