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Preparation method for perfluorohexyl acetate

A technology of perfluorohexylethanol and perfluorohexyl, which is applied in the field of preparation of perfluorohexyl acetate, can solve the problems of carcinogenicity, chromium content and high cost, and achieves the effects of easy industrial production, mild reaction conditions and less catalyst amount

Inactive Publication Date: 2015-08-19
JUHUA GROUP TECH CENT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] As one of the substitutes, perfluorohexyl acetate has low surface tension and good emulsifying properties for the polymerization of fluorine-containing olefins. The properties and preparation methods of the surfactant have been reported in relevant literature, and the preparation methods are all To use an oxidizing agent, the oxidizing agent used includes Jones reagent (CrO 3 / H 2 SO 4 ), periodic acid (HIO 4 ) and potassium permanganate (KMnO 4 ), the above-mentioned methods all have deficiencies, such as Jones reagent containing chromium, poisonous and carcinogenic, very harmful to human body and environment, periodic acid has strong irritation and corrosiveness, harsh to equipment requirements, potassium permanganate method Sulfuric acid or alkaline solution is required to catalyze, and a large amount of waste water will be generated, and a large amount of waste solid manganese dioxide will be generated, and the treatment of the three wastes is difficult
For the oxidation of common fatty alcohols to acids, literature (Organic Letters 7 (2005) 2933–2936) reported that in 2-iodobenzoic acid (2IBAcid), 2-iodobenzoic acid (IBX) or 2-iodosobenzene The method for preparing carboxylic acid under the common oxidation of formic acid (IBA) and Oxone (potassium hydrogen persulfate complex salt), but it does not mention the oxidation of fluorine-containing alcohol to fluorine-containing carboxylic acid, and its catalyst (2IBAcid, IBX or IBA) consumption is bigger, mole fraction is 20~30%, cost is higher, and yield is lower

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] In a 500mL four-necked flask, add 36.4g (0.1mol) of perfluorohexylethanol, 160ml of acetonitrile, 80ml of deionized water, 2g of 2IBAcid (0.008mol), 46g of Oxone (0.15mol), and heated to 65°C in a water bath for reaction, every hour. Sampling once for chromatographic analysis. After 14 hours, the raw material perfluorohexylethanol reacted completely, the reaction was completed, and the layers were left to stand to obtain an upper organic phase and a lower aqueous phase. The lower aqueous phase was removed, and the upper organic phase was evaporated to dryness with a rotary evaporator. White solid, add this solid to 100ml deionized water at 60°C, neutralize it with ammonia water to pH 8, filter after cooling, wash the filter cake with 50ml×2 deionized water to obtain the crude product, dissolve the crude product in 200ml 60°C In hot water, after cooling, a white solid was precipitated, filtered under reduced pressure, and the filter cake was washed with 50ml×2 deionized w...

example 2

[0024] In a 500mL four-necked flask, add 36.4g (0.1mol) of perfluorohexylethanol, 250ml of dioxane, 25ml of deionized water, 5.3g (0.02mol) of IBA, 153.5g (0.5mol) of Oxone, and heat to 80°C in a water bath Carry out the reaction, take a sample every hour for chromatographic analysis, after 10 hours, the raw material perfluorohexylethanol reacts completely, finish the reaction, stand for stratification, obtain an upper organic phase and a lower aqueous phase, remove the lower aqueous phase, and use a rotary evaporator for the upper organic phase. Evaporate the solvent to dryness, white solid remains, add this solid to 100ml of deionized water at 60°C, neutralize it to pH 8 with aqueous sodium hydroxide solution, filter after cooling, and wash the filter cake with 50ml×2 of deionized water to obtain the crude product , the crude product was dissolved in 200ml of 60°C hot water, a white solid was precipitated after cooling, filtered under reduced pressure, and the filter cake was...

example 3

[0026] In a 500mL four-necked flask, add 36.4g (0.1mol) of perfluorohexylethanol, 30ml of acetonitrile, 2.8g (0.01mol) of IBX, heat to 70°C in a water bath, and dropwise add 300ml of deionized water (dissolved with 30.7g of Oxone) within 6h. , 0.1mol), continue the insulation reaction after dripping, take samples once per hour for chromatographic analysis, after 12h the raw material perfluorohexylethanol reacts completely, finish the reaction, stand for stratification, obtain the upper organic phase and the lower aqueous phase, remove the lower water Phase, the upper organic phase was evaporated to dryness with a rotary evaporator, leaving a white solid, which was added to 100 ml of deionized water at 60 ° C, neutralized to pH 8.5 with an aqueous potassium hydroxide solution, filtered after cooling, and the filter cake was used 50 ml The crude product was obtained by washing with ×2 deionized water. The crude product was dissolved in 200ml of hot water at 60°C. After cooling, a...

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Abstract

The invention discloses a preparation method for perfluorohexyl acetate. The method includes the steps of: (a) reacting perfluorohexyl ethanol, a catalyst and an oxidant in a mole ratio of 1:0.01-0.2:1-5 in a solvent at 50-80DEG C for 10-24h, at the end of reaction, conducting standing layering to obtain an upper layer organic phase and a lower layer aqueous phase, and subjecting the organic phase to solvent separation to obtain a white solid; and (b) adding the white solid obtained in step (a) into deionized water, conducting neutralizing with an alkali solution to a PH value of 8-9, carrying out cooling and filtering to obtain a filter cake, and subjecting the filter cake to washing, recrystallization and drying so as to obtain the product. The method provided by the invention has the advantages of simple process, high yield, safety and environmental protection, low cost, and easy realization of industrial production.

Description

technical field [0001] The invention relates to a preparation method of a fluorocarbon surfactant, in particular to a preparation method of perfluorohexyl acetate. Background technique [0002] Perfluorooctanoic acid and its primary salt containing ammonium (PFOA), perfluorooctanesulfonyl compounds (PFOS) is an indispensable processing aid for the production of high performance fluoropolymers. These high-performance fluoropolymers can be widely used in aviation technology, transportation, electronics industry, and household products such as kitchenware. PFOA is the most commonly used fluorine-containing surfactant in the emulsion polymerization of fluorine-containing monomers. However, because of its potential bioaccumulation, toxicity and regional diffusion, it has biological carcinogenicity. restricted use. In 2001, the US EPA proposed an autonomous reduction plan for PFOA, and large companies in the preparation of fluororesin also responded positively. In 2015, the use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C53/21C07C51/305C07C51/41
CPCC07C51/305C07C51/412C07C2601/14C07C53/21
Inventor 兰喜平周强汪星平耿为利吴庆王宗令王树华
Owner JUHUA GROUP TECH CENT
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