Method for synthesizing 1-ferrocenylethanol

A synthesis method and ferrocene technology, applied in chemical instruments and methods, metallocene, organic chemistry, etc., can solve the problems of discharging a large amount of waste water, increasing product cost, unfavorable promotion and utilization, etc., to reduce environmental protection pressure and reduce emissions , The effect of reducing waste water discharge and solvent loss

Inactive Publication Date: 2014-02-12
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a small number of manufacturers in China use a large amount of ethanol as a solvent, cooling down and adding sodium borohydride to the reduction process, and the yield is only about 91%. If it is too large, the recycling cost will be high, which will increase the cost of the product, which is not conducive to popularization and utilization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] In a 1000ml reaction flask equipped with stirring, thermometer and reflux condenser, add 47.2g (0.2mol) acetyl ferrocene and 600ml aqueous methanol solution, cool down to -5°C and stir, add 15.7g (0.4mol) in 6 times Sodium borohydride, reacted at 0°C for 3 hours. After the reaction, after the reaction was completed, 400mL of methanol was extracted for concentration, and 100g of ammonium chloride aqueous solution was added to destroy the reaction. Then, 300ml of solvent dichloroethane was added for extraction, and 200ml of water was added to stir. layer, the organic layer was taken for precipitation to obtain 44.3g of 1-ferrocenyl ethanol with a content of 95.2% and a yield of 98.9%.

Embodiment 2

[0013] In a 1000ml reaction flask equipped with stirring, thermometer and reflux condenser, add 97.7g (0.43mol) acetyl ferrocene and 800ml aqueous methanol solution, cool down to 0°C and stir, add 33.9g (0.86mol) boron in 6 times Sodium hydride, react at 5°C for 2 hours. After the reaction, after precipitation and concentration, add 200g of ammonium chloride aqueous solution to destroy the reaction, then add 600ml of solvent dichloroethane for extraction, add 400ml of water to stir, let the layers stand, and take the organic layer to desorb. Dissolved to obtain 94.7g of 1-ferrocenyl ethanol with a content of 95.1% and a yield of 99.1%.

Embodiment 3

[0015] In a 500ml reaction flask equipped with stirring, thermometer and reflux condenser, add 60.1g (0.255mol) acetyl ferrocene and 450ml aqueous methanol solution, cool down to 5°C and stir, add 20.1g (0.51mol) boron in 6 times Sodium hydride, reacted at 5°C for 4 hours. After the reaction was completed, after precipitation and concentration, 125g of ammonium chloride aqueous solution was added to destroy the reaction, and then 375ml of solvent dichloroethane was added for extraction, and 250ml of water was added to stir. Dissolved to obtain 60.1g of 1-ferrocenyl ethanol with a content of 92.6% and a yield of 96.8%.

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Abstract

The invention discloses a method for synthesizing 1-ferrocenylethanol, and relates to the technical field of technical material production. The method comprises the following steps of mixing an aqueous solution of methanol and acetyl ferrocene while stirring under the condition of reaction system temperature of -5 to 5 DEG C, putting sodium borohydride in batches for reaction, adding an aqueous solution of ammonium chloride to damage excessive sodium borohydride to prevent explosion during desolventizing after the reaction is finished, and performing desolventizing and concentration; and adding a solvent for extraction, adding water for demixing, and desolventizing an organic layer to obtain the 1-ferrocenylethanol. According to the synthesis method, ethanol is replaced by the aqueous solution of methanol in a fixed proportion, so that the reaction speed is increased, difficulty in the reaction is lowered, the reduction product content is increased to about 93 percent, the yield is increased to about 97 percent, the discharge of wastewater and the loss of the solvent during reaction are reduced, the energy consumption is lowered, the production cost is lowered, and the discharge of the wastewater is greatly reduced.

Description

technical field [0001] The invention relates to the technical field of original medicine production, in particular to the technical field of synthesis technology of 1-ferrocenyl ethanol, an intermediate of the hydrogenation catalyst bisphosphine ligand of the agricultural herbicide S-isopropyl metolachlor. Background technique [0002] 1-Ferrocenyl ethanol is an intermediate for the synthesis of the bisphosphine ligand of the hydrogenation catalyst of the agricultural herbicide S-isopropyl metolachlor. S-Metachlor is a selective herbicide that inhibits cell growth by hindering protein synthesis. Through the young shoots of plants, that is, the coleoptiles of monocotyledonous plants and the hypocotyls of dicotyledonous plants, the absorption and conduction is upward, and the absorption and conduction of seeds and root fluids are small, and the speed is slow. After emergence, it mainly relies on root absorption and upward conduction to inhibit the growth of young shoots and r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 于国权王建荣吉志扬窦伟
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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