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Preparation method of n-hexyl carborane

A technology of n-hexyl carborane and bromomethyl carborane, which is applied in the field of preparation of n-hexyl carborane, can solve the problems such as high price of 1-octyne, and achieves reduction of production cost, small steric hindrance, and total cost reduction. high yield effect

Active Publication Date: 2014-09-03
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The shortcoming of this method is: (1) the cage yield of last step has only 40%, causes the yield of whole route to be only 33.3%; (2) raw material 1-octyne is expensive

Method used

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  • Preparation method of n-hexyl carborane
  • Preparation method of n-hexyl carborane
  • Preparation method of n-hexyl carborane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Add 4.0g (15.1mmol) ditetraethylammonium decahydrodecaborate and 35mL diethyl sulfide into the reaction flask, add 12mL of a mixture of concentrated sulfuric acid and diethyl sulfide in an equal volume ratio at 0°C, and then After the reaction was completed for 6 hours, the supernatant was poured out, neutralized with triethylamine to pH ≈ 8, filtered, and the filtrate was evaporated to dryness under reduced pressure to obtain 2.76 g of dodecahydrodecaboron bis-diethylsulfide complex. The yield was 87.0%.

[0024] (2) Add 3.0 g (10 mmol) of dodecahydrodecaboron bis-diethyl sulfide complex, 15 mL of toluene, and 3 g (20 mmol) of propynyl bromide toluene solution with a mass fraction of 80% into the reaction flask, and heat at 85° C. Reacted for 9 hours, after the reaction was completed, filtered, the filtrate was neutralized with triethylamine to pH ≈ 8, and the solvent was distilled off under reduced pressure to obtain 1.90 g of bromomethylcarborane with a yield of ...

Embodiment 2

[0035] (1) Add 4.0g (15.1mmol) ditetraethylammonium decahydrodecaborate and 30mL diethyl sulfide into the reaction flask, add 10mL of concentrated sulfuric acid and diethyl sulfide equal volume mixture at 10°C, and then 15°C After the reaction was completed for 5 hours, the supernatant liquid was poured out, neutralized with triethylamine to pH ≈ 8, filtered, and the filtrate was evaporated to dryness under reduced pressure to obtain 2.38 g of dodecahydrodecaboron bis-diethylsulfide complex. The yield was 75.0%.

[0036] (2) 3.0 g (10 mmol) of dodecahydrodecaboron bis-diethylsulfide complex, 15 mL of toluene, and 1.5 g (10 mmol) of bromopropynyl toluene solution with a mass fraction of 80% were added to the reaction flask, and After reaction at ℃ for 10 h, after the reaction, filter, the filtrate was neutralized with triethylamine to pH ≈ 8, and the solvent was distilled off under reduced pressure to obtain 1.88 g of bromomethylcarborane with a yield of 79.2%.

[0037] (3) Re...

Embodiment 3

[0039] (1) Add 4.0g (15.1mmol) ditetraethylammonium decahydrodecaborate and 30mL diethyl sulfide into the reaction flask, add 15mL of concentrated sulfuric acid and ethyl sulfide equal volume mixture at 5°C, and then 10°C React for 5.5 hours. After the reaction is over, pour out the supernatant, neutralize with triethylamine to pH ≈ 8, filter, and evaporate the filtrate to dryness under reduced pressure to obtain 2.71 g of dodecahydrodecaboron bis-diethylsulfide complex , and the yield was 85.3%.

[0040] (2) 3.0g (10mmol) of dodecahydrodecaboron bis-diethylsulfide complex, 15mL toluene, and 4.5g (30mmol) of bromopropynyl toluene solution with a mass fraction of 80% were added to the reaction flask, and After reaction at ℃ for 9 hours, after the reaction, filter, the filtrate was neutralized with triethylamine to pH ≈ 8, and the solvent was distilled off under reduced pressure to obtain 1.88 g of bromomethylcarborane with a yield of 79.3%.

[0041] (3) React 1.31 mL (10.5 mmo...

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Abstract

The invention provides a preparation method of n-hexyl carborane, and the preparation method comprises the following steps: by taking decahydro-decaborate ditetraethylammonium as a raw material and ethyl thioether as a reaction raw material and a solvent, reacting the materials in the presence of a concentrated sulfuric acid used as a catalyst, so that a dodecahydrogen-decabo-diethyl thioether complex is obtained; by taking methylbenzene as a solvent, reacting the dodecahydrogen-decabo-diethyl thioether complex with propargyl bromide, so that brooethyl carborane is obtained; by taking tetrahydrofuran as a solvent, reacting the brooethyl carborane with a grignard reagent of bromopentane, so that n-hexyl carborane is obtained. The method is cheap and easily available in raw materials, relatively high in yield and low in preparation cost, and the method disclosed by the invention is applied to the preparation of n-hexyl carborane.

Description

technical field [0001] The invention relates to a method for preparing carborane, in particular to a method for preparing n-hexylcarborane. Background technique [0002] Carborane derivatives with a closed cage structure have always been concerned by aviation and rocket workers because they inherit the high combustion calorific value of borohydrides and overcome the latter’s shortcomings such as high chemical activity and high toxicity. The one with the most and high practical value is n-hexylcarborane. According to reports, the U.S. Department of the Army uses n-hexylcarborane as a burning rate regulator in the formulation of the alternative butylated hydroxyl propellant specially developed for the "Guardian" anti-ballistic missile system, and its addition is 13.10%, so that the propellant can obtain It has a high burning rate of 144.78mm / s (13.73MPa) and a high specific impulse of 2400N.s / Kg, and has good overall comprehensive performance. [0003] Due to the excellent p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/05
Inventor 李娇毅吕剑薛云娜李春迎杜咏梅唐晓博孙道安吕婧万洪张建伟
Owner XIAN MODERN CHEM RES INST
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