Method for synthesizing adamantane acid ester

A technology of adamantanoic acid ester and a synthesis method, which is applied in the field of adamantanoic acid ester synthesis, can solve problems such as being unsuitable for industrial production, difficult to purify by reaction, and achieve a simple and easy separation method, high yield, and easy experimental conditions. Effect

Inactive Publication Date: 2010-04-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the prior art uses H 2 SO 4 Synthesis of adamantane ester for catalyst reaction, its reaction purification is difficult, not suitable for large-scale industrial production

Method used

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  • Method for synthesizing adamantane acid ester
  • Method for synthesizing adamantane acid ester
  • Method for synthesizing adamantane acid ester

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Dry adamantanecarboxylic acid in a vacuum drying oven at 85°C for 3h, take 5g (27.2mmol) of adamantanecarboxylic acid and 10ml of dichloromethane into a 50ml round-bottomed flask, and drop slowly at a rate of 0.5ml / min with a constant pressure dropping funnel Add a mixture of oxalyl chloride 4ml and dichloromethane 10ml, and react at 5°C for 6h to obtain a brown-black liquid. Unreacted oxalyl chloride was removed by rotary evaporation to obtain adamantanecarbonyl chloride.

[0023] Add dropwise a mixture of n-butanol 2ml (21.7mmol), dichloromethane 4ml and pyridine 2ml to the above product, react in an ice bath at 0°C (reaction temperature is -20-30°C) for 2h, and filter to remove Pyridinium salt, wash the filtrate with 1mol / L hydrochloric acid, wash with water, separate the liquid, wash with alkali again, and separate the oil phase liquid. An appropriate amount of calcium chloride was added to dry the product, filtered, and the remaining dichloromethane was removed by...

Embodiment 2

[0026] Dry adamantanecarboxylic acid in a vacuum oven at 85°C for 5h, take 5g (27.2mmol) of adamantanecarboxylic acid and 10ml of dichloromethane in a 50ml round-bottomed flask, and drop slowly at a rate of 0.5ml / min with a constant pressure dropping funnel Add excess 6ml of oxalyl chloride and 10ml of dichloromethane to react at 20°C for 1 hour to obtain a brownish-black liquid. Unreacted oxalyl chloride was removed by rotary evaporation to obtain adamantanecarbonyl chloride.

[0027] Add dropwise a mixture of 4ml of lauryl alcohol (18.1mmol), 6ml of dichloromethane and 4ml of freshly distilled pyridine to the above product, react at -10°C for 8h, remove the pyridinium salt by filtration, wash the filtrate with 2mol / L hydrochloric acid, and wash with water , liquid separation, and then alkali washing to separate the oil phase liquid. An appropriate amount of calcium chloride was added to dry the product, filtered, and the remaining dichloromethane was removed by rotary evapo...

Embodiment 3

[0029] 1,3-adamantanedicarboxylic acid was dried in a vacuum oven at 90°C for 5h, 5g (22.3mmol) of 1,3-adamantanedicarboxylic acid and 10ml chloroform were placed in a 50ml round bottom flask, and the Slowly add a mixture of excess oxalyl chloride 12ml and dichloromethane 10ml dropwise into the funnel at a rate of 1.5ml / min, and react at -10°C for 3h to obtain a brownish-black liquid. Unreacted oxalyl chloride was removed by rotary evaporation to obtain adamantanoyl chloride.

[0030] Add dropwise a mixture of n-octanol 13ml (83.3mmol), dichloromethane 6ml and freshly distilled pyridine 4ml to the above product, react in an ice-bath environment at 0°C for 8h, filter to remove the pyridine salt, and wash with 1mol / L hydrochloric acid The filtrate is washed with water, separated, and then washed with alkali to separate the oil phase liquid. An appropriate amount of calcium chloride was added to dry the product, filtered, and the remaining dichloromethane was removed by rotary e...

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Abstract

The method discloses a method for synthesizing adamantane acid ester. The method includes the following steps: firstly, adding adamantane carboxylic acid and straight chain fatty acid into a solvent, slowly dropping excess oxalyl chloride at the rate of 0.5-1.5 ml / min under the temperature from minus 10 to 30 DEG C to react for 1 to 6 hours, and acylating the adamantane carboxylic acid and the straight chain acid so as to prepare a corresponding acyl chloride product thereof; and secondly, preparing the organic solvent mixed liquor of dolichol and adamantanol, and respectively and slowly dropping the organic solvent mixed liquor into adamantanecarbonyl chloride according to the mole ratio of 1:1-3 of alcohol to acyl chloride groups to react for 1 to 10 hours, thereby synthesizing adamantane ester oil. The method has the advantages of easy implementation, and fast reaction rate, and high yield and purity of products.

Description

technical field [0001] The invention relates to adamantyl ester oil, in particular to a synthesis method of adamantyl ester. Background technique [0002] Synthetic lubricants are oils obtained by synthetic methods. These lubricants often have unique properties not found in mineral oils. According to the chemical structure of synthetic lubricating oil base oil, industrially produced synthetic lubricating oil is divided into six categories: ester oil, polyether, synthetic hydrocarbon, silicone oil, fluorine oil, and phosphate ester. There are many types of esters, including monoesters, dibasic acid diesters, glycol diesters, dibasic acid glycol double esters, polyol esters, polyether monoesters, polyether diesters, etc., and have been successfully applied in Jet engine oil, steam turbine oil, compressor oil and hydraulic oil and other fields. [0003] Adamantane (tricyclo[3.3.1.1 3，7 ]Decane) is a positively symmetrical and highly stable caged hydrocarbon with a wide vari...

Claims

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Application Information

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IPC IPC(8): C07C69/753C07C67/14
Inventor 刘卅郭建维任力张德智
Owner SOUTH CHINA UNIV OF TECH
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