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Process for preparing levogyrate alpha-terpineol

A technology of terpineol and resin, applied in hydroxyl addition preparation, organic chemistry and other directions, can solve the problem of low yield of α-terpineol, and achieve the effects of less solvent consumption, high temperature and high activity

Inactive Publication Date: 2004-03-17
GUANGXI RES INST OF CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Domestic Hu Meikang [Chemical World. 1987, (6). 249~251], Lin Zhongxiang et al. [Guangdong Chemical Industry. 1992. (1). 43~44], Li Qianhe et al. [Journal of Natural Science of Hunan Normal University. 1).36~39], Zhang Zhiliu et al. [Journal of Central South Forestry University. 2000, 20(2).32~35], Yang Yan et al. [Forest Industry. 2000, 27(2). The research of cation-exchange resin catalyzed synthesis of terpineol, although the reaction time, product yield etc. are compared with Japanese patent, the yield of α-terpineol is not high (about 55%), and the product is still racemic Terpineol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Catalyst preparation

[0013] Put the hydrogen type D001 macroporous strongly acidic styrene-based cation exchange resin into 1.2% ferric chloride solution, the volume ratio of the ion exchange resin to the solution is 1:3, at a temperature of 50 to 55°C and -0.05 to - Under a vacuum of 0.06MPa, soak for 8 hours, filter out the ferric chloride solution, and repeat the treatment 2 to 3 times under the same conditions. In the same way, the ion exchange resin was treated with 1.3% copper chloride solution, 0.2% titanium tetrachloride solution, and 0.5% zirconium nitrate solution successively, and then washed with deionized water until no chloride ions were used. Dry at a temperature of 110-120°C and a vacuum of -0.09--0.095 MPa to prepare a modified D001 hydrogen-type strongly acidic styrene-based cation exchange resin catalyst.

Embodiment 2

[0015] Catalyst preparation

[0016] Put hydrogen type 001×7 strongly acidic styrene-based cation exchange resin into 0.5% ferric chloride solution, the volume ratio of ion exchange resin to solution is 1:3, at a temperature of 50~55°C and -0.05~- Under a vacuum of 0.06MPa, soak for 11 hours, filter out the ferric chloride solution, and repeat the treatment 2 to 3 times under the same conditions. In the same way, the ion exchange resin was treated with 0.3% cupric chloride solution, 0.1% titanium tetrachloride solution, and 0.2% zirconium nitrate solution successively, and then washed with deionized water until there was no chloride ion. Dry at a temperature of 100°C and a vacuum of -0.09 to -0.095 MPa to prepare a modified 001×7 hydrogen-type strongly acidic styrene-based cation exchange resin catalyst.

Embodiment 3

[0018] Synthesis of L-α-Terpineol

[0019] 280 grams of the modified D001 hydrogen-type strongly acidic styrene-based cation-exchange resin catalyst prepared in Example 1 are loaded into a tubular fixed-bed reactor with a diameter of 20 mm and a length of 600 mm. Add 300 grams of α 25 D =-12.5 ° of turpentine (about containing pinene 91%, 2 moles), 54 grams of water (3 moles) and 60 grams of 99% n-propanol (1 mole), heating makes pinene, water and n-propanol evaporate and control The evaporation amount, after being condensed by the condenser, enters the tubular fixed-bed reactor for reaction, and then refluxes into the three-necked flask for continuous circulation, maintaining the temperature of the fixed-bed reactor at about 90°C, and reacting for 9 hours. After completion of the reaction, remove n-propanol by simple distillation, and then rectify under reduced pressure to collect 130~140 ℃ / 40mmHg cuts to obtain 243 grams of L-α-terpineol, and the product yield is 75%; α 2...

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Abstract

The present invention provides one-step levo-alpha-terpineol synthesizing process, in which turpentine oil with alpha-pinene as main component is used as the material, low-carbon alcohol or ketone assolvent and modified strong acid styrene cationic exchange resin as catalyst and the catalytic hydration is completed in a fixed bed reactor. It has catalyst / alpha-pinene weight ratio of 1 to 1-10, alpha-pinene / water molar ratio of 1 to 1.1-2, water / solvent molar ratio of 1 to 0.1-0.9, reaction temperature of 70-100 deg.c, reaction period of 5-13 hr, alpha-pinene converting rate over 95 % and levo-alpha-terpineol yield over 65 %.

Description

technical field [0001] The invention relates to a preparation method of L-α-terpineol. More specifically, it relates to a method for synthesizing L-alpha-oleyl alcohol in one step with a modified cation exchange resin as a catalyst in a fixed bed. Background technique [0002] Terpineol, also known as sycamore oil and terpineol, is a monocyclic monoterpene alcohol compound with molecular formula C 10 h 18 O, with a molecular weight of 154.24, has three isomers of α-, β-, and γ-, among which α-terpineol is the most common in nature. It has been found that α-terpineol exists in the leaves, flowers, and in grass stems. α-Terpineol has three optical forms: left-handed, right-handed and racemic. D-Terpineol exists in plant essential oils such as cypress, cardamom, star anise, and orange blossom. L-Terpineol exists in miscellaneous lavender Among the plant essential oils such as melaleuca, white lemon, cinnamon leaf, etc., racemic terpineol exists in geranium oil, white dry la...

Claims

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Application Information

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IPC IPC(8): C07C29/04C07C35/08
Inventor 黄科林樊晓丹王桂英龙玉艳韦毅
Owner GUANGXI RES INST OF CHEM IND CO LTD
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