Method for preparing borneol

A technology of orthoborneol and borneol, which is applied in the field of preparing orthoborneol, can solve problems such as low yield, complicated reaction, and low cost, and achieve the effects of high product yield, simple post-processing, and reduced cost

Active Publication Date: 2014-09-10
株洲松本药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The present invention aims at the main defects of complex reaction and low yield in the prior art, and provides a method for preparing orthoborneol, which has the characteristics of high efficiency and low cost

Method used

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preparation example Construction

[0031]The method for preparing orthoborneol of the present invention comprises the following steps: dissolving the synthesized crude borneol in an organic solvent, and then standing for a certain period of time to remove impurities such as moisture and soil in the lower layer. Add boric anhydride, pyroboric acid, metaboric acid or metatitanic acid catalyst, react with a certain amount of anhydrous oxalic acid at a certain temperature for a period of time, filter to remove unreacted anhydrous oxalic acid and catalyst after the reaction, wash 3 to 5 times with water The catalyst and oxalic acid are further removed. After the organic solution is distilled to recover the solvent, tricyclene, camphene and a small amount of borneol and isoborneol are removed by steam distillation to obtain bornyl oxalate and isobornyl oxalate. The obtained bornyl oxalate and isobornyl oxalate are subjected to saponification to obtain a high content borneo product. This reaction can use aromatic hyd...

Embodiment 1

[0035] In a 250mL four-necked round-bottomed flask, add 10.0g of crude borneol (commercially available borneol, containing 60.6%wt of borneol), add 1.0g of boric anhydride catalyst and 2.5g of metatitanic acid catalyst, 15.0g of anhydrous oxalic acid, Use 30.0g of n-hexane as solvent, stir and condense to reflux, maintain the temperature at 54-56°C, and the reaction time is 24h. After the reaction is completed, remove the solvent, camphene and tricyclene, and saponify the remaining liquid to obtain a crude product. After refining, 3.1g The orthoborneol product has a content of 88.1% (orthoborneol:isoborneol=88.1:8.1), and the orthoborneol extraction rate is 45.1%.

Embodiment 2

[0037] In a 250mL four-necked round-bottomed flask, add 5.0g of crude borneol (containing 54.2%wt of borneol), add 1.0g of boric anhydride catalyst, 5.5g of anhydrous oxalic acid, and use 65.7g of n-hexane as a solvent, stir and condense to reflux , temperature is maintained at 54~56 ℃, and reaction time 35h, after reaction finishes, remove solvent and amphene, tricyclic olefin, remaining liquid saponification obtains crude product after refining and obtains 2.1g orthoborneol product, and content is 71.8% (orthoborneol Brain:isoborneol=71.8:12.3), the extraction rate of orthoborneol was 55.6%.

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Abstract

The invention discloses a method for preparing borneol. The method comprises the following steps: dissolving crude borneol into an organic solvent, reacting with an anhydrous oxalic acid under the action of a catalyst, filtering and removing the anhydrous oxalic acid and the catalyst, which do not completely react, washing and removing the catalyst and an oxalic acid, distilling a residual organic liquid and recovering the solvent; distilling residues by vapor to remove tricyclene, camphene and a part of unreacted borneol, so as to obtain a borneol oxalate ester intermediate product containing a part of oxalate isoborneol acetate; and then saponifying the borneol oxalate ester intermediate product, so as to obtain a borneol product with high content. The conventional heating mode is adopted, so that the method is fast in reaction speed, mild in condition, simple and convenient to operate, easy for separation of a product, and high in product yield.

Description

technical field [0001] The invention relates to a method for preparing orthoborneol from crude synthetic borneol (crude borneol) or synthetic borneol. Background technique [0002] Turpentine is a kind of natural essential oil with unique aroma obtained from pine resin secreted by pine trees through water vapor distillation. my country has abundant turpentine resources, and its annual output ranks first in the world. The main components of turpentine are α-pinene and β-pinene. Pine massoniana turpentine also contains a small amount of longifolene and caryophyllene. Therefore, turpentine can provide a C10 or C15 molecular skeleton, and at the same time provide multiple rings, bridge rings, and rings. Active structures such as external or internal double bonds have very high chemical reactivity, and are rare natural chemical synthesis raw materials, which are of great significance in the synthesis of spices and other functional substances [Zhao Zhendong, Liu Xianzhang. I)—Tur...

Claims

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Application Information

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IPC IPC(8): C07C35/30C07C29/88
CPCC07C29/095C07C29/88C07C67/08C07C35/30C07C69/36
Inventor 赵振东张平辉徐士超田新庭毕良武刘晓辉陈玉湘雷腊王婧张瑞华
Owner 株洲松本药业有限公司
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