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Carborane and preparation method thereof

A carborane and formula technology, applied in the field of carborane, can solve problems such as migration, and achieve the effects of low synthesis cost, strong reactivity and favorable industrial production

Inactive Publication Date: 2011-08-03
天元航材(营口)科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The invention provides a carborane and a preparation method thereof, specifically a cage carborane containing an alkenyl ether side chain and a preparation method thereof, in which the carbon-carbon double bond in the alkenyl ether side chain is used to participate in solid propulsion The cross-linking and curing reaction of the agent can solve the migration problem existing when the existing plasticized carborane is added as a solid propellant burning rate catalyst

Method used

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  • Carborane and preparation method thereof
  • Carborane and preparation method thereof
  • Carborane and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of allyloxymethylcarborane

[0036] In a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, add 200 g of ether, 70.1 g of pyridine and 20.6 g of allyl alcohol, and add 50.8 g of propyne bromide under stirring at room temperature. After the addition, keep warm at 30°C and stir for 12h. After the reaction, the generated salt was removed by filtration, and the solvent was distilled off from the filtrate at 40-45° C. to obtain 25.0 g of light yellow transparent oily liquid allyl propargyl ether with a purity of 99.0% and a yield of 74.2%.

[0037] Add 12.4g of decaborane, 19.2g of allyl propargyl ether and 70g of acetonitrile into a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, stir, heat to reflux, and react for 16 hours. After finishing the reaction, the reaction solution was cooled to room temperature, filtered, and the fil...

Embodiment 2

[0040] Embodiment 2: the preparation of allyloxyethoxymethylcarborane

[0041] In a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, add 150g of tetrahydrofuran, 35.5g of pyridine and 36.3g of ethylene glycol allyl ether, and add 26.7g of chloropropyne under stirring at room temperature. After the addition, keep warm at 65°C and stir for 18h. After the reaction was finished, the generated salt was removed by filtration, and the filtrate was distilled to remove the solvent at 65-70° C. to obtain 26.8 g of light yellow transparent oily liquid allyloxyethoxypropargyl ether with a purity of 98.9% and a yield of 54.6%.

[0042]Add 6.2g of decaborane, 14.1g of allyloxyethoxypropargyl ether and 125g of acetonitrile into a three-neck flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, stir, heat to reflux, and react for 16h. After finishing the reaction, the reaction solution was coo...

Embodiment 3

[0045] Embodiment 3: the preparation of hexeneoxymethylcarborane

[0046] In a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, 280g of tetrahydrofuran, 33.5g of pyridine and 37.6g of 5-enylhexanol were added, and 50.8g of propyne bromide was added under stirring at room temperature. After the addition, keep warm at 65°C and stir for 16h. After the reaction, the generated salt was removed by filtration, and the filtrate was distilled to remove the solvent at 65-70° C. to obtain 28.3 g of light yellow transparent oily liquid allyloxyethoxy propargyl ether with a purity of 97.6% and a yield of 57.7%.

[0047] Add 12.2g of decaborane, 28.0g of allyloxyethoxypropargyl ether and 300g of acetonitrile into a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, stir, heat to reflux, and react for 20 hours. After finishing the reaction, the reaction solution was cooled to ...

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Abstract

The invention discloses a carborane and a synthesis method thereof. In the method, propiolic halide is adopted as a raw material to synthesize propargyl ether containing unsaturated carbon-carbon double bond through nucleophile substitution reaction, and the alkynyl in the propargyl ether is adducted with decaborane to obtain reactive carborane in which a carbon-carbon double bond is bonded on a cage type carborane structure through an ether bond. The synthesized reactive carborane, which is liquid at normal temperature, can have an effect of a plasticizer while being used as a composite solid burning-rate catalyst of a propellant. The unsaturated group carbon-carbon double bond, which has disconjugacy and strong reactivity, contained in the carborane is expected to overcome migration through taking part in the crosslinking curing reaction with the composite solid propellant. The carborane containing unsaturated carbon-carbon double bond has low synthesis cost and simple and convenient production technique, and is beneficial for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis for propellants, and uses propargyl halides as raw materials to synthesize propargyl ethers containing unsaturated carbon-carbon double bonds through nucleophilic substitution reactions. Addition of borohydrogen yields a class of carboranes containing unsaturated carbon-carbon double bonds. Background technique [0002] Carborane is a compound with a tetrahedral closed cage structure formed by the reaction of borohydride compounds and alkynes. It has been widely studied abroad as a solid propellant high burning rate regulator or binder, and has been developed A series of stable carborane compounds, which are compatible with propellant components, can especially enable composite propellants and double-base propellants to obtain good ballistic properties such as high burning rate or ultra-high burning rate. For example, in 1976, the composite propellant for the "Viper" rocket launcher developed by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/05B01J31/14
Inventor 李战雄吕德斌
Owner 天元航材(营口)科技股份有限公司
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