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Method for producing all trans-teprenone

A technology of teprenone and all-trans, which is applied in the field of production of all-trans teprenone, can solve the problems that the separation degree cannot reach the expected goal, and it is difficult to produce in large quantities.

Active Publication Date: 2014-04-16
RIANLON TIANJIN IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, low-temperature separation technology is used at home and abroad to separate it, but the separation degree cannot reach the expected goal, and it is difficult to mass-produce

Method used

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  • Method for producing all trans-teprenone
  • Method for producing all trans-teprenone
  • Method for producing all trans-teprenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) After installing a glass column with a height of 400 mm and a diameter of 19 mm, a stirrer, and a thermometer on a 2500 ml glass four-necked flask, add 500 g of geranyllinalool, 280 g of methyl acetoacetate, and 8 g of aluminum isopropoxide. Raise the temperature, stir, slowly raise the temperature to 130°C and see bubbling, and methanol begins to flow out at 135°C, collect the methanol liquid, continue to heat up to about 170°C, stop heating, keep it warm for 4 hours, and after cooling down to room temperature, replace the above glass column Distillation under reduced pressure was carried out for a glass column with a height of 600 mm and a diameter of 24 mm. Use an electric heating mantle to start heating up, turn on the vacuum pump when the liquid phase temperature of the reaction liquid rises to 100°C, the vacuum degree is 0.9mmHg, and the temperature is about 140°C, the excess methyl acetoacetate gradually flows out from the reaction, and after all the methyl ac...

Embodiment 2

[0049] (1) Put 6.4Kg of geranyllinalool, 3.6Kg of methyl acetoacetate, and 102g of aluminum isopropoxide into a 20-liter stainless steel reaction tank. After stirring evenly, the temperature began to rise. Under stirring, the temperature was slowly raised to 135°C and methanol began to flow out, and the methanol liquid was collected. Continue to heat up to about 170°C, stop heating, start to keep warm for 4 hours, and then drop to normal temperature. Install a vacuum distillation device, the vacuum degree is 0.8mmHg, and start to heat up. At about 140°C, as the reaction deepens, excess methyl acetoacetate gradually flows out. After all the methyl acetoacetate is evaporated, the temperature is raised to 180°C. The crude renone (mixed type) began to flow out, and it was all evaporated at 190°C, and the residue in the kettle was centrally disposed of.

[0050] Take out and weigh to get the crude product teprenone 6.33Kg, take a sample, measure with Shimadzu GC-14C gas chromatogr...

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Abstract

The invention provides a method for producing all trans-teprenone, comprising the following steps of: (1) synthesizing teprenone through Carroll reaction to obtain a teprenone crude product; (2) pickling the teprenone crude product by the use of hexane and sulfuric acid, carrying out alkali washing by the use of a sodium bicarbonate solution, washing to neutral, and removing an emulsification layer and a water layer to obtain mixed teprenone after washing; (3) adding hexane for dilution, standing at minus 15-minus 20 DEG C for 20-24 hours, cooling to minus 30-minus 60 DEG C, and crystallizing all trans-teprenone; and (4) centrifuging the crystals at minus 20-minus 40 DEG C to obtain the all trans-teprenone having a purity of greater than 99%. Through an ultralow temperature separation method and an apparatus, all trans-teprenone having a purity of greater than 99% is obtained from a cis-trans isomer which is hard to separate under the condition of high temperature and other purities which can be separated by a rectification means. In addition, cis and other impurities do not exceed 1%.

Description

technical field [0001] The invention relates to a method for producing all-trans teprenone. Background technique [0002] Teprenone (also known as pentacentrone; chemical name is 6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraenone-2- Ketone), the English name is Teprenone, as a novel gastric mucosal protective agent, it has unique physical and chemical properties and a good anti-ulcer mechanism, and has a good curative effect on acute gastritis, chronic gastritis and gastric ulcer. [0003] At present, the synthetic method of the reported teprenone mainly contains following two kinds: [0004] 1. Under the action of an aluminum isopropoxide catalyst, geranyl linalool and alkyl acetoacetate are subjected to a Carroll reaction (Carroll reaction), and the obtained γ, δ-unsaturated ketone is teprenone; [0005] 2. Substitution reaction of halogenated tetramethylhexadetraene and sodium acetoacetate hydrocarbyl ester, followed by saponification and decarboxylation to obtain tepr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/203C07C45/78
Inventor 张越于开锋张玮
Owner RIANLON TIANJIN IND CO LTD
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