Method for synthesizing squalene

A synthesis method and technology of squalene, applied in chemical instruments and methods, hydrocarbons, hydrocarbons, etc., can solve the problems of explosion of polymerization reaction, unfavorable industrial production, harsh reaction requirements of sodium acetylene, etc., and improve safety. , The advantages of industrialization are obvious and the operation is convenient.

Inactive Publication Date: 2010-11-24
SHANGYU NHU BIOCHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Equally, the used sodium acetylene of this route is harsh to reaction, and during coupling reaction, there is the danger of polymerization reaction explosion, is unfavorable for suitability for industrialized production

Method used

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  • Method for synthesizing squalene
  • Method for synthesizing squalene
  • Method for synthesizing squalene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1) Put 41.5g (0.25mol) of triethyl phosphite into a four-necked flask, heat it in an oil bath to 110°C, add 12.7g (0.1mol) of dichlorobutane dropwise, after the drop, raise the temperature to 180°C, and keep warm 6.0 hours of reaction. Sampling, gas phase detection to stop the reaction when the intermediate is less than 0.2%. A distillation unit was connected to remove the low boilers to obtain 30 g of crude oil with a yield of 90.9%.

[0024] 2) Dissolve 30g of crude oil in 200ml of toluene and cyclohexane mixed solvent (1:1), add 48.5g (0.25mol) geranyl acetone, stir, cool to 30°C, slowly add 10.8g (0.2mol) ) sodium methoxide, keep the temperature at about 50° C., keep it warm for 5.0 hours, drop ice water into the reaction container, stir for half an hour, and let stand to separate layers. The water layer was separated, and the organic layer was washed with water, washed with brine, dried over anhydrous magnesium sulfate, and concentrated to obtain 35 g of crude pr...

Embodiment 2

[0026] 1) Put 41.5g (0.25mol) of triethyl phosphite into a four-necked flask, heat it in an oil bath to 140°C, add 12.7g (0.1mol) of dichlorobutane dropwise, after the drop, raise the temperature to 180°C, and keep warm 6.0 hours of reaction. Sampling, gas phase detection to stop the reaction when the intermediate is less than 0.2%. Connect the distillation unit to remove low boilers to obtain 31 g of crude oil with a yield of 93.9%.

[0027] 2) Dissolve 31g of crude oil in 200ml of toluene and cyclohexane mixed solvent (1:2), add 48.5g (0.25mol) geranyl acetone, stir, cool to 30°C, slowly add 12g (0.3mol) Sodium hydroxide, keep the temperature at about 50°C, keep warm for 5.0 hours, drop ice water into the reaction container, stir for half an hour, let stand and separate into layers. The water layer was separated, and the organic layer was washed with water, washed with brine, dried over anhydrous magnesium sulfate, and concentrated to obtain 36 g of crude product, which wa...

Embodiment 3

[0029] 1) Put 41.5g (0.25mol) of triethyl phosphite into a four-necked flask, heat it in an oil bath to 140°C, add 12.7g (0.1mol) of dichlorobutane dropwise, after the drop, raise the temperature to 180°C, and keep warm 6.0 hours of reaction. Sampling, gas phase detection to stop the reaction when the intermediate is less than 0.2%. A distillation unit was connected to remove the low boilers to obtain 30 g of crude oil with a yield of 90.9%.

[0030] 2) Dissolve 30g of crude oil in a mixed solvent (1:1) of 200ml toluene and cyclohexane, add 48.5g (0.25mol) geranyl acetone, stir, cool to 30°C, slowly add 41.4g (0.3mol) ) Potassium carbonate, keep the temperature at about 50° C., keep the temperature for 8.0 hours to react, drop ice water into the reaction container, stir for half an hour, and let stand to separate layers. The water layer was separated, and the organic layer was washed with water, washed with brine, dried over anhydrous magnesium sulfate, and concentrated to o...

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Abstract

The invention discloses a method for synthesizing squalene. Certain conventional synthetic routes are too long and require operation at an extremely low temperature; and certain conventional synthetic routes have harsh requirements on reactions and have the risk of polymerization reaction explosion so that the conventional synthetic routes are not beneficial for industrial production. The method comprises the following steps of: performing a reaction of dichlorobutane serving as a raw material and triethyl phosphite to generate phosphonate; and performing a Wittig-Horner reaction of the phosphonate and geranylacetone to obtain the squalene. The raw material in the invention does not contain any substance which is easy to be polymerized so that safety is enhanced greatly; and a formed double bond has trans-selectivity and high overall yield so that a synthesis route which has very remarkable industrial advantages is achieved.

Description

technical field [0001] The invention relates to polyterpenoids, especially a method for synthesizing squalene. Background technique [0002] The chemical name of squalene is: 2, 6, 10, 15, 19, 23-hexamethyl-2, 6, 10, 14, 18, 22-tetracosahexaene, which is a long-chain triterpenoid . Squalene is a colorless or slightly yellow oily liquid with a pleasant smell, and becomes viscous into linseed oil after absorbing oxygen, with a specific gravity of 0.8584 g / cm 3 , melting point -75°C, boiling point about 330°C (atmospheric pressure, decomposed), 280°C / 2.27KPa, 285°C / 3.30KPa, 240°C-242°C / 533Pa, flash point 110°C, refractive index n D 20 1.4965, viscosity 0.012Pa·s, soluble in ether, petroleum ether, acetone and carbon tetrachloride, slightly soluble in ethanol and glacial acetic acid, insoluble in water. [0003] Squalene is a lipid unsaponifiable substance, which has many physiological functions such as improving the activity of superoxide dismutase (SOD) in the body, enhanc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C11/21C07C1/34
Inventor 曾庆宇宋文杰沈烨高均勇梁志军张琴
Owner SHANGYU NHU BIOCHEM IND
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