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Preparation method of ferrocenecarboxylic acid

A technology of ferrocene formic acid and acetyl ferrocene, applied in chemical instruments and methods, metallocene, organic chemistry, etc., can solve the problems of many by-products, low total yield, and high requirements for experimental equipment, and achieves reaction consumption. Short, easy-to-control, inexpensive effects

Active Publication Date: 2011-11-02
启东市三江建筑机械有限公司
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AI Technical Summary

Benefits of technology

This patented process allows for producing ferrocene carbonyl oxide (FCO) by reacting an acetic acid ester derivative called 2-(acetyloxy)-N-2'-methoxytoluo-3 '-trifluorobutane-1 -ammononitrile or 4-(dimethylaminomalonicotinate). By adding hydrogen bromide at room temperatures below 100°C, it forms ferrocenesulfone monohydroxystrobin instead of iron cerozoquinone. These new compounds have unique properties such as high stability towards heat decomposition compared to existing methods like lithography techniques. They also exhibits excellent antiozonant activity against harmful chemical agents found inside buildings due to their ability to absorb ultraviolet light without losing its effectiveness when exposed to sunlight.

Problems solved by technology

The technical problem addressed in this patents relates to finding ways to efficiently produce large amounts (>100 grams per gram or even larger than 100 g/g) of specific types of ferrocenes that can have different bioactivities such as antimicrobial properties due to their ability to bind iron atoms within them.

Method used

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  • Preparation method of ferrocenecarboxylic acid

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Embodiment 1

[0022] In the first step, add 60 ml of deionized water and 10 g of sodium hydroxide to the reactor and stir to dissolve it to form a sodium hydroxide solution; cool the reactor to 0-5°C in an ice-water bath, and add 2 ml of PEG-400 under stirring (Polyethylene glycol) and 16.8 gram iodine-potassium iodides, add the acetyl ferrocene powder that total amount is 2.3 grams then in 40 minutes, each addition is equal, then fully stir 1h;

[0023] In the second step, the solution obtained in the first step is extracted and washed twice with dichloromethane, and the water phase is adjusted to PH=2 to 3 with strong acid, and a yellow precipitate is precipitated, filtered after cooling, washed twice with water, and the solid obtained by filtering is di Ferrocene formic acid, the calculated yield by weighing is 85.6%. see figure 1 Shown is the infrared spectrogram of embodiment 1 gained solid product, can find out that institute's product is ferrocenecarboxylic acid by spectrogram.

Embodiment 2

[0025] In the first step, 60 ml of deionized water and 10 g of sodium hydroxide were added to the reactor and stirred to dissolve to form a sodium hydroxide solution; the reactor was cooled to 10°C with an ice-water bath, and 2 ml of PEG-400 and 16.8 gram of iodine-potassium iodide, in 40 minutes, add the acetyl ferrocene powder that total amount is 2.76 grams in batches, then fully stir 1h;

[0026] In the second step, the solution obtained in the first step is extracted and washed twice with dichloromethane, and the water phase is adjusted to PH=2 to 3 with strong acid, and a yellow precipitate is precipitated, filtered after cooling, washed twice with water, and the solid obtained by filtering is di Ferrocene formic acid, the calculated yield by weighing is 84%.

Embodiment 3

[0028] In the first step, 60 ml of deionized water and 10 g of sodium hydroxide were added to the reactor and stirred to dissolve to form a sodium hydroxide solution; the reactor was cooled to 30°C with an ice-water bath, and 2 ml of PEG-400 and 16.8 Gram iodine-potassium iodide, add the acetyl ferrocene powder that total amount is 3.22 grams in 40 minutes, then fully stir 1h;

[0029] In the second step, the solution obtained in the first step is extracted and washed twice with dichloromethane, and the water phase is adjusted to PH=2 to 3 with strong acid, and a yellow precipitate is precipitated, filtered after cooling, washed twice with water, and the solid obtained by filtering is di Ferrocene formic acid has a yield of 79.3% by weight.

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Abstract

The invention relates to a preparation method of ferrocenecarboxylic acid, comprising the following steps of: firstly, adding polyethylene glycol, iodine-potassium iodide and acetylferrocene into an aqueous alkali with uniformly stirring, wherein the acetylferrocene undergoes an iodoform reaction to form ferrocene carboxylic acid salt dissolved in a non-organic phase; secondly, extracting the solution obtained from the reaction of the first step by the use of an organic solvent, adjusting the pH value of a water phase to 2-3 by the use of strong acid to change sodium ferrocene carboxylic acid into ferrocenecarboxylic acid precipitated from the water phase. According to the invention, non-organic aqueous alkali is used as a solvent to prepare ferrocenecarboxylic acid. The preparation method provided by the invention is easy to control. During the process, the mild reaction is carried out in a solution with the reaction temperature being from zero to 5 DEG C for a short time; ferrocenecarboxylic acid can be produced only within 2 hours. The used raw materials are commonly sold in the market and are cheap. The yield of the product in the invention can reach more than 85% by optimum technology.

Description

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Claims

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Application Information

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Owner 启东市三江建筑机械有限公司
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