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Method of producing alpha- terpineol

A technology of terpineol and petroleum ether, applied in the field of preparation of alpha-terpineol, can solve the problems of less reuse, equipment corrosion, long time consumption and the like

Inactive Publication Date: 2009-11-04
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many by-products, large consumption of raw materials, complex production process, long time-consuming, serious equipment corrosion, and "three wastes" pollution
In the 1970s, Yoshiharu Matsubara of Japan, etc., used chloroacetic acid to catalyze the hydration of pinene, and opened up a precedent for the preparation of terpineol by organic acid catalyzed hydration of pinene. The yield and selectivity of the final product terpineol can be compared with the sulfuric acid method Comparable, but consume more chloroacetic acid, less reuse, high cost and other disadvantages
There are phase-transfer catalysis, membrane catalysis, etc., but these methods cannot solve the shortcoming of low purity in the preparation of α-terpineol

Method used

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  • Method of producing alpha- terpineol
  • Method of producing alpha- terpineol

Examples

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preparation example Construction

[0012] The preparation method of α-terpineol comprises the following steps: a preparation method of α-terpineol comprises the following steps:

[0013] a. Add lithium aluminum hydride to the organic solvent at 0°C, dissolve 8,9-epoxy limonene in the organic solvent, add 8,9-epoxy limonene solution dropwise to the lithium aluminum hydride solution, Carry out the ring-opening reaction at 0-5°C for 5-10 hours, add ice water drop by drop to the reaction system under stirring until no hydrogen is released, then add 5-20% dilute sulfuric acid to the reaction system to dissolve The aluminum hydroxide produced by the reaction precipitates, separates the water layer, extracts with ether, washes with saline solution, and filters to remove the ether to obtain a crude product, wherein the organic solvent is selected from ether, tetrahydrofuran, N,N-dimethylformamide or di One of methyl chloride; b. The crude product is separated with a silica gel column, and the product is rinsed with a m...

Embodiment 1

[0015] Weigh 0.9865 g of lithium aluminum hydride into a 100 mL three-necked flask filled with 30 mL of anhydrous ether, and at 0°C, add 1.0148 g of 8,9-epoxylimonene and 10 ml of anhydrous ether solution dropwise, and simultaneously turn on the magnetic Stirrer, after the raw material is added dropwise, react at room temperature for 6.5 hours. Cool the product obtained by the reaction with ice water, and add ice water very carefully (drop by drop) under stirring until no hydrogen is released, and then add 25 ml of 10% sulfuric acid by mass fraction to precipitate aluminum hydroxide was dissolved. Separate the water layer with a separatory funnel, and extract three times with ether, combine the ether extracts, wash with saturated saline solution, add Na 2 SO 4 Drying, filtration and evaporation of ether gave 0.6316 g of product. Such as figure 1 Shown, the terpineol purity of the present invention is greater than 98% as determined by gas chromatography.

[0016] Table 1 g...

Embodiment 2

[0024] Weigh 0.5034 grams of lithium aluminum hydride and pour it into a 100 mL three-necked flask filled with 30 ml of anhydrous tetrahydrofuran, cool it with ice water and stir it magnetically, add dropwise a mixture of 0.5011 grams of 8,9-epoxylimonene and 10 ml of anhydrous tetrahydrofuran solution, reacted at room temperature for 6.5 hours. After the reaction was finished, cool with ice water, add ice water dropwise under stirring until no more hydrogen gas was released, then add 25ml of sulfuric acid with a mass fraction of 10%, and the aluminum hydroxide precipitate was dissolved. Separate with a separatory funnel, extract the aqueous layer three times with ether, combine the ether solutions and wash with saturated brine, add Na 2 SO 4 Drying, filtration and evaporation of ether gave 0.2985 g of product.

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Abstract

The invention discloses a preparation method of α-terpineol. Lithium aluminum hydride is dissolved in an organic solvent at a low temperature, and then the ether solution of 8,9-epoxy terpinene is added to carry out ring-opening reaction of epoxide , the aluminum hydroxide precipitate generated by the dissolution reaction of dilute sulfuric acid, the aqueous layer was separated, extracted with ether, washed with common saline solution, filtered, and the ether was removed to obtain the crude product; the crude product was separated with a silica gel column, and a mixed solvent of petroleum ether and ethyl acetate was used to separate the crude product Use as eluent to elute the product, and after removing the solvent, a colorless and thick α-terpineol is obtained with a purity greater than 98%.

Description

technical field [0001] The present invention relates to a kind of preparation method of aromatic terpene alcohol, more specifically relates to a kind of preparation method of α-terpineol. Background technique [0002] α-Terpineol is a colorless thick liquid with a density of about 0.931-0.941 at 20°C, a refractive index of 1.4825-1.4850, and a boiling point of 214-224°C. It is soluble in ethanol and other organic solvents, insoluble in water, and has a stable The lilac aroma is widely present in a variety of essential oils. There are three isomers of terpineol, namely α-form, β-form and γ-form terpineol. Commercial terpineol is a mixture of these three isomers, of which α-form is the main one. α-terpineol with a content higher than 90% is often used as a solvent, bactericide, disinfectant, detergent, cleaning agent, blending essence, flotation agent for non-ferrous metal ore, etc., except for solvents and spices In addition, it is also used as an intermediate in organic sy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/14C07C29/132
Inventor 杨始刚周晓君施凌捷
Owner SHANGHAI INST OF TECH
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