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Method for preparing 3-methyl-2-butenol

A technology of butenol and methyl, which is applied in the field of preparing 3-methyl-2-butenol to achieve the effects of improving selectivity, increasing energy consumption, and avoiding by-products of hydrogenation

Active Publication Date: 2017-09-08
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The isomerization reaction of 3-methyl-3-butenol reported in patent CN102701910 uses iron pentacarbonyl and alkaline aqueous solution as a catalyst, and reacts at 80°C for 3 hours in the absence of hydrogen. The purified prenol product has a purity of 98.25%. , the yield is 30%, there is no report on the selectivity and catalyst separation, the analysis is that there is a problem in the recovery and application of the catalyst

Method used

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Embodiment 1

[0045] Under the protection of nitrogen atmosphere, 5 g (10 mmol) of triiron dodecacarbonyl and 0.75 g (5 mmol) of propylene oxide phenyl ether were mixed and stirred at room temperature for 24 h, then 5 g (50 mmol) of triethylamine was added and stirred at room temperature for 12 h. The mixture was transferred to an autoclave and 258 g (3 mol) of 3-methyl-3-butenol and 50 g of 18-crown-6 were added. The reactor was replaced 10 times with nitrogen containing 5000 ppm of carbon monoxide, the temperature of the reactor was raised to 80° C., the pressure was 0.5 MPa, and the reactor was stirred for 2 hours. The organic phase was analyzed by gas chromatography. The conversion was 47.3%, and the selectivity was 98.8%.

Embodiment 2

[0047] Under the protection of nitrogen atmosphere, 2g (10mmol) of iron pentacarbonyl and 0.65g (5mmol) of 2-phenylpropylene oxide were mixed and stirred at room temperature for 12h, then 8g (100mmol) of pyridine was added and stirred at room temperature for 6h. The mixed solution was transferred to the autoclave and added 17.2g (0.2mol) of 3-methyl-3-butenol and

[0048] 150 g macrogol 200. The reactor was replaced with nitrogen containing 10 000 ppm of carbon monoxide for 10 times, the temperature of the reactor was raised to 70° C., the pressure was 0.5 MPa, and the reactor was stirred for 24 hours. The organic phase was analyzed by gas chromatography. The conversion was 79.8%, and the selectivity was 99.0%.

Embodiment 3

[0050] Under the protection of nitrogen atmosphere, 3.6g (10mmol) of nonacarbonyl ferric iron and 0.15g (2mmol) of 3-hydroxy-1,2-propylene oxide were mixed and stirred at room temperature for 1h, and then 2g (20mmol) of triethylamine was added, Stir at room temperature for 1 h. The mixture was transferred to an autoclave and 172 g (2 mol) of 3-methyl-3-butenol and 200 g of polypropylene glycol 400 were added. The reactor was replaced 10 times with nitrogen containing 5 000 ppm of carbon monoxide, the temperature of the reactor was raised to 80° C., the pressure was 0.5 MPa, and the reactor was stirred for 0.5 h. The organic phase was analyzed by gas chromatography. The conversion was 51.3%, and the selectivity was 85.1%.

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Abstract

The invention provides a method for preparing 3-methyl-2-butenol (isoprenol) through isomerization of 3-methyl-3-butenol. A catalyst reaction system contains 1) a carbonyl iron compound, 2) an organic base, and 3) an epoxy group ligand. A solvent with an ether structure is added into an isomerization reaction, so that the activity of a catalyst can be improved, and the product selectivity is improved. During catalysis and separation, a mixed gas of carbon monoxide (CO) and nitrogen (N2) is introduced, wherein the volume content of the CO is 100-100000ppm. The catalyst and a raw material namely the 3-methyl-3-butenol are separated from a product namely isoprenol through rectification, and the catalyst does not need to be additionally separated. The catalyst keeps high activity and long life operation.

Description

technical field [0001] The invention relates to a method for preparing 3-methyl-2-butenol (prenol) through isomerization of 3-methyl-3-butenol. Background technique [0002] The chemical name of prenol is 3-methyl-2-butenol, which is an important organic intermediate and can be used in the production of various fine chemical products and pharmaceuticals such as citral, floral fragrance and vitamin A. The traditional method for producing prenol is mainly the isoprene method, that is, isoprene is used as a raw material to prepare prenol through processes such as oxidation, esterification, and alkaline solution saponification. This method has a long process route, large consumption of raw materials, many by-products, relatively high production cost and serious pollution. In recent years, the preparation method of isopentenol using isobutylene as raw material has become a research hotspot. It has simple process flow, few by-products, rich sources of raw materials, low productio...

Claims

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Application Information

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IPC IPC(8): C07C29/56C07C29/80C07C33/03
CPCC07C29/56C07C29/80C07C33/03
Inventor 鲍元野姜庆梅张永振黎源王文唐义权庞计昌于斌成
Owner WANHUA CHEM GRP CO LTD
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