Preparation method of ethyl dicyclopentadienyl iron

A technology of ethyl ferrocene and acetyl ferrocene, applied in chemical instruments and methods, metallocene, organic chemistry and other directions, can solve problems such as high cost, incomplete conversion, unsuitable for industrial production, etc., and achieves low cost , The effect of short reaction time and high product yield

Inactive Publication Date: 2010-04-28
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method uses acetyl ferrocene as raw material, sodium borohydride as reducing agent, adds anhydrous zinc chloride to tetrahydrofuran solvent and reacts at room temperature for 10-12 hours, and the prepared ethyl ferrocene product needs to use the method of column Purification, incomplete conversion within the reaction time, high cost, unsuitable for industrial production (Synthetic communications, 1996, 26(24): 4647-4654)

Method used

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  • Preparation method of ethyl dicyclopentadienyl iron
  • Preparation method of ethyl dicyclopentadienyl iron

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 0.06mol (13.68g) acetyl ferrocene, 0.25mol (33.3g) anhydrous aluminum trichloride and 150ml chloroform to a 500ml three-necked reaction flask equipped with a thermometer, a reflux condenser and a magnetic stirring device. Stir, add 0.24mol (9.1g) sodium borohydride dropwise, heat to 50°C, react for 6 hours, cool to room temperature, add 20% ammonia water dropwise, adjust to PH=10, separate the organic phase, and use 100ml three Extracted twice with methyl chloride, combined the organic phases, washed with water until neutral, dried with anhydrous sodium sulfate, and evaporated the solvent from the dried liquid to obtain 12.3 g of crude product with a purity of 97.3% (HPLC), and distilled under reduced pressure to obtain ethyl di Ferrocene product 11.0g, yield 86.6%, purity 99.1% (HPLC), boiling point: 97-98°C / 170Pa.

Embodiment 2

[0025] Add 0.06mol (13.68g) acetyl ferrocene, 0.28mol (38.2g) anhydrous zinc chloride and 200ml 1,2-dichloro to a 500ml three-necked reaction flask equipped with a thermometer, a reflux condenser and a magnetic stirring device Ethane, stirred at room temperature, added dropwise 0.26mol (14g) potassium borohydride, heated to 60°C, reacted for 3.5 hours, cooled to room temperature, added dropwise 20% ammonia water, adjusted to PH = 12, separated the organic phase and the aqueous phase Extract twice with 100ml of 1,2-dichloroethane, combine the organic phases, wash with water until neutral, dry with anhydrous sodium sulfate, and evaporate the solvent from the dried solution to obtain 12.5 g of crude product with a purity of 97.8% (HPLC). Distilled under reduced pressure to obtain 11.6 g of ethyl ferrocene product, with a yield of 90%, a purity of 99% (HPLC), and a boiling point of 97-98°C / 170Pa.

Embodiment 3

[0027] Add 0.06mol (13.68g) acetyl ferrocene, 0.21mol (28.6g) anhydrous zinc chloride and 180ml 1,2-dichloro to a 500ml three-necked reaction flask equipped with a thermometer, a reflux condenser and a magnetic stirring device Ethane, stirred at room temperature, added dropwise 0.2mol (7.6g) sodium borohydride, heated to 65°C, reacted for 4.5 hours, cooled to room temperature, added dropwise 20% ammonia water, adjusted to PH = 11, separated the organic phase, water The phase was extracted twice with 100ml of 1,2-dichloroethane, the organic phases were combined, washed with water until neutral, dried with anhydrous sodium sulfate, and the dry solution was evaporated to remove the solvent to obtain 12.3g of crude product with a purity of 98.1% (HPLC) , Distilled under reduced pressure to obtain 11.8g of ethyl ferrocene product, yield 92%, purity 99.2% (HPLC), boiling point: 97~98°C / 170Pa.

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Abstract

The present invention discloses a preparation method of ethyl ferrocene. Said method includes the following steps: using acetylferrocene as raw material, using borohydride as reducing agent, using haloolefin as solvent, in the presence of Brnsted acid making them produce reduction reaction, using alkaline solution to regulate pH value so as to obtain the invented target product whose purity is upto above 99% and yield is 87-92%.

Description

technical field [0001] The invention relates to a preparation method of ethyl ferrocene. Background technique [0002] Ethyl ferrocene is an intermediate of a solid fuel burning rate catalyst, and can especially be used in a burning rate catalyst of a butylated hydroxyl composite solid propellant. Its structural formula is as follows: [0003] [0004] In the prior art, the methods reported by Wang Xueyan etc. use zinc powder, mercuric chloride, concentrated hydrochloric acid, and water to make zinc-amalgam, use benzene as solvent, heat reflux with raw material acetyl ferrocene, drop concentrated hydrochloric acid, and react After 5-7 hours, after post-treatment, ethyl ferrocene was obtained with a yield of 72% (Applied Chemistry 2002, 19(10): 950-954). The method needs to be reduced with zinc-amalgam, and benzene is used as a solvent. The operation is unsafe, the toxicity is high, the yield is low, the method is quite dangerous, and the industrialization prospect is no...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02
Inventor 何扣宝袁振文蒋旭亮
Owner SHANGHAI CHEM REAGENT RES INST
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