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Method for preparing high-purity borneol from camphor, camphor reduction product and borneol

A high-purity, camphor-based technology, used in the fields of chemistry and medicine, can solve problems such as difficult industrialization, pollution, and low yield

Inactive Publication Date: 2014-04-23
闻永举
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The metabolic rate of the two is different in the body. The hydroxyl group of borneol is in the flat bond, which is conducive to the combination with glucuronic acid, while the hydroxyl group of isoborneol is in the vertical bond. The steric hindrance of the base makes the combination difficult; after the combination, the upper end of the sugar ring in the glucuronide, 6-COOH and isoborneol, are both large groups, especially the upright 1,7,7-three Methyl, resulting in a large steric tension of the sugar ring, very unstable and easy to hydrolyze
The role of the two makes its metabolism slow, stays in the body for a long time, and has a large effect, which also leads to more prominent side effects
Using steam distillation alone to remove heavy metals will consume more energy
[0011] The separation and disadvantages of borneol and camphor: the solubility of borneol and camphor in ethanol is slightly different, and the solubility of camphor in ethanol is large. In the case of cooling, the precipitation rate of borneol is slower than that of borneol, and repeated ethanol recrystallization is required. separate
[0012] Separation and disadvantages of borneol and isoborneol: due to the very similar properties of borneol and isoborneol, it is difficult to separate them on a large scale with the current conventional scientific methods
However, the traditional boric anhydride catalyzed a-pinene esterification-saponification method has disadvantages such as easy flushing, low safety, high corrosion, and serious pollution, and it is difficult to realize industrialization ([8] Liu Yonggen, Deng Zhihong, etc. Synthesis of external borneol A new method of [J].Journal of Jiangxi Normal University, 2004, 28(3):193-195)
(4) Using Grignard reagents: Song Xinlu and others used natural camphor to react with Grignard reagents with active hydrogen on β-2C to mainly obtain isoborneol, and the yield of borneol was very low
Natural borneol and mugwort are extracted from borneol camphor and Ainaxiang respectively. On the one hand, their extracts contain more camphor. Repeated recrystallization of ethanol to remove camphor requires complicated process and low yield.
On the other hand, D-borneol and L-borneol are low in plants, which require large-scale planting and will also occupy a large amount of arable land
Two aspects lead to the high price of natural borneol or moxa, up to thousands of yuan per kilogram

Method used

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  • Method for preparing high-purity borneol from camphor, camphor reduction product and borneol
  • Method for preparing high-purity borneol from camphor, camphor reduction product and borneol
  • Method for preparing high-purity borneol from camphor, camphor reduction product and borneol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Isopropanol is an example,

[0068] Take 4g aluminum powder (AR) and add 4g anhydrous AlCl 3 (AR), mix quickly, add 200ml of isopropanol (AR), under airtight, reflux in a water bath for 12h, add 100g of borneol, in a water bath until the borneol is dissolved, shake well to form a homogeneous solution. Distill about 170 ml -180 ml of isopropanol in a gas bath at 120°C. Under airtight, react at 150°C for 15h in a gas bath, add water, and after heating for 2h, pass into steam distillation, condense, and the distillate first comes out of a liquid containing camphene and a small amount of camphene. The latter mainly contains borneol crystalline solid and a small amount of camphene. A small amount of camphene was heated to dissolve borneol, and then sublimated at 170°C-180°C to obtain 40.2g. The purity of borneol was determined by GC to be 96.8%. Based on borneol, the yield of borneol was 40.2%.

Embodiment 2

[0070] Take 4g aluminum powder (AR) and add 4g anhydrous AlCl 3 (AR), mix quickly, add 200ml of isopropanol (AR), under airtight, reflux in a water bath for 12h, add 100g of borneol, in a water bath until the borneol is dissolved, shake well to form a homogeneous solution. Distill about 170 ml -180 ml of isopropanol in a gas bath at 120°C. Under airtight, react at 150°C for 15h in a gas bath, add water, and after heating for 2h, pass into steam distillation, condense, and the distillate first comes out of a liquid containing camphene and a small amount of camphene. The latter mainly contains borneol crystalline solid and a small amount of camphene. Add a small amount of camphene and 4 times the amount of borneol to dissolve in cyclohexane, divide the upper layer solution, dry with anhydrous sodium sulfate, add 200ml DMSO (AR), evenly, place it at 10℃ for 3-4h, divide the lower layer solution Or siphon the lower layer solution, dilute with water, filter, and crystallize it once...

Embodiment 3

[0072] Take 4g aluminum powder (AR) and add 4g anhydrous AlCl 3 (AR), mix quickly, add 200ml of isopropanol (AR), under airtight, reflux in a water bath for 12h, add 100g of borneol, in a water bath until the borneol is dissolved, shake well to form a homogeneous solution. Distill about 170ml -180ml of isopropanol in a gas bath at 120°C. Under airtight, react at 150℃ for 15h in a gas bath, add water, heat for 2h, pass into steam distillation, condense, the distillate first comes out of the liquid containing camphene and a small amount of camphene, using 4 times the amount of cyclohexane The alkane is dissolved and dried with anhydrous sodium sulfate to obtain sample solution (I). The latter mainly contains borneol crystalline solid and a small amount of camphene. Add a small amount of camphene and 4 times the amount of borneol to dissolve in cyclohexane, divide the upper solution, and dry with anhydrous sodium sulfate to obtain sample solution (II). Take 350g of column chroma...

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Abstract

The invention provides a method for preparing high-purity borneol from camphor, a camphor reduction product and borneol. Camphor borneol and isoborneol are produced through the reduction of the camphor, camphor in the camphol reduction product and camphor in borneol by the methods of aluminum isopropoxide, sodium-alcohol, raney nickel and the like. Secondary alcohol or tertiary alcohol with a low boiling point is evaporated to produce borneol aluminum or isoborneol aluminum through the airtight heating of the camphol reduction product or the borneol and secondary alcohol-secondary alcohol aluminum with a low boiling point or tertiary alcohol-tertiary alcohol aluminum with a low boiling point, camphene is produced by the dehydration and the rearrangement of the isoborneol aluminum through continuous airtight heating, the camphene and borneol are evaporated through steam distillation, and the camphene is separated from the borneol by one or a combination of the distilling-sublimation method, the extracting method and the column chromatographic method. The method has the advantages of smooth whole technology, simplicity in operation, greenness, environment-friendliness, cheap reagent, low cost, easiness in industrial production and high borneol yield. The camphor, heavy metal and the isoborneol in the borneol and the camphor reduction product can be removed by the method, the obtained camphor content is high, and the method for preparing the camphene from the borneol and the camphor reduction product is provided.

Description

Technical field [0001] A method for preparing high-purity borneol from camphor, its reduction products, and borneol. Its field is chemistry and medicine. Background technique [0002] The pharmacological effects and clinical application of Borneol: Borneol has the effects of resuscitation and refreshing, clearing away heat and relieving pain. It is used for fever, fainting, convulsions, stroke, phlegm, qi depression, coma, nausea, chest pain, red eyes, mouth sores, Symptoms such as sore throat and ear drainage. Borneol exerts a variety of effects in Chinese patent medicine preparations and is widely used in the field of medicine. Briefly explain the pharmacological effects and main drugs of Borneol from 4 aspects: (1) The effect on the central nervous system: Borneol has a strong two-way regulation effect on the excitability of the central nervous system. It has both sedative and tranquilizing effects and refreshing effects. The main products are Xueyinole, Naotong injection, Z...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C35/30C07C29/143C07C29/09C07C29/80C07C29/76C07C13/40C07C5/27C07C1/24C07C7/04C07C7/00
CPCC07C1/24C07C29/143C07C29/705C07C2602/42C07C35/30C07C35/46C07C13/40
Inventor 闻永举申秀丽
Owner 闻永举
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