CN101851147A - Synthesis method of diaryl hexafluoropropane compound - Google Patents

Synthesis method of diaryl hexafluoropropane compound Download PDF

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CN101851147A
CN101851147A CN201010189099A CN201010189099A CN101851147A CN 101851147 A CN101851147 A CN 101851147A CN 201010189099 A CN201010189099 A CN 201010189099A CN 201010189099 A CN201010189099 A CN 201010189099A CN 101851147 A CN101851147 A CN 101851147A
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hydrogen fluoride
propylene oxide
diaryl
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谢伟东
郑建瑞
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Sanming Hexafluo Chemicals Co Ltd
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Sanming Hexafluo Chemicals Co Ltd
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Abstract

The invention relates to a synthesis method of a diaryl hexafluoropropane compound, which comprises the following steps that: aromatics with one or more electron repulsive groups are mixed with anhydrous hydrogen fluoride in a reactor, and then hexafluoropropylene oxide is added into the reactor to be mixed and heated; after the reaction, the hydrogen fluoride is removed, the remained product is refined to obtain the diaryl hexafluoropropane compound; with the method, the isomerization of hexafluoropropylene oxide and the concentration reaction of aromatics are integrated into one process stage to be realized, so the process procedure of the synthesis is reduced, and the production cost and side product can be reduced.

Description

A kind of synthetic method of diaryl hexafluoropropane compound
Technical field
The present invention relates to a kind of synthetic method of diaryl hexafluoropropane compound.
Background technology
Diaryl hexafluoropropane compound is meant 2, and the hexafluoropropane compound that the 2-diaryl replaces is as 2,2-phenylbenzene-HFC-236fa, 2,2-two (4-hydroxy phenyl)-HFC-236fa (being commonly called as bisphenol AF or BPAF), 2,2-two (3, the 4-3,5-dimethylphenyl)-HFC-236fa (is commonly called as 6FXY; Or BoxAF), 2,2-two (4-aminomethyl phenyl)-HFC-236fa (being commonly called as BTAF or BIS-T-AF).These compounds are products very with practical value in special fluorine-containing chemical industry, for example 2,2-two (4-hydroxy phenyl)-HFC-236fa is the used vulcanizing agents of 26 class viton, 2,2-two (3, the 4-3,5-dimethylphenyl)-HFC-236fa is the raw material of the principal monomer 6FDA of synthetic fluorinated polyimide.
The synthetic method that this compounds is traditional is with specific aromatic hydrocarbon, with the Perfluoroacetone trihydrate, in anhydrous hydrogen fluoride, reacts under certain temperature and pressure.
Reaction formula is as follows:
2ArH+CF 3COCF 3-3H 2O-------→Ar-C(CF 3) 2-Ar+4H 2O
Because the mechanism of this reaction is Fu-Ke reaction, is the aromatic hydrocarbon with one or more electron donating groups so require the specific aromatic hydrocarbon as reaction raw materials, such aromatic hydrocarbon just has enough reactive behavioies of carrying out Fu-Ke reaction.Like this specific aromatic hydrocarbon such as phenol, benzene that alkyl replaces such as toluene, o-Xylol, benzene that alkoxyl group replaces such as anisole, phenetole, dialkyl amido benzene such as diethylaniline etc.
Russian patent USSR117491 described with phenol and Perfluoroacetone trihydrate in the presence of anhydrous hydrogen fluoride in the reaction of 100 degrees centigrade of synthesis of bisphenol A F.
Among the U.S. Pat P3310573, E.I.Du Pont Company expands to multiple aromatic hydrocarbon and the reaction of Perfluoroacetone trihydrate with this traditional technology, for example, toluene mixes with Perfluoroacetone trihydrate and anhydrous hydrogen fluoride, 160 degrees centigrade of reactions, obtain 2,2-two (4-aminomethyl phenyl)-HFC-236fa.
Used Perfluoroacetone trihydrate in the above prior synthesizing method generally is by the Propylene oxide hexafluoride isomerization after water absorbs and refining obtaining.In addition, in this process, relate to multiple arrangements such as reactor, water absorption unit, rectifying tower, and pilot process there is highly toxic anhydrous Perfluoroacetone, causes environmental protection and safety problem easily.
In addition, use the Perfluoroacetone trihydrate during tradition is synthetic, bring the water of three times of molar weights of real reaction raw material Perfluoroacetone into for reaction system, and reaction itself needs to use anhydrous hydrogen fluoride as catalysts and dewatering agent, the water-content of Zeng Jiaing makes real reaction compare condensation reaction itself in theory like this needs to use more hydrogen fluoride, and increasing of water-content can cause its metal to reactor to produce bigger corrodibility in the hydrogen fluoride, thereby brings the production safety problem into.
Summary of the invention
The object of the present invention is to provide a kind of synthetic method of diaryl hexafluoropropane compound, present method makes the Propylene oxide hexafluoride isomerization and merges in the technology with the condensation reaction of specific aromatic hydrocarbon and realizes, reduced the synthetic processing step, reduce production cost and by product and generated, helped environmental protection and safety.
The present invention is achieved in that
A kind of synthetic method of diaryl hexafluoropropane compound is characterized in that, the aromatic hydrocarbon that will have one or more electron donating groups mixes in reactor earlier with anhydrous hydrogen fluoride, adds Propylene oxide hexafluoride then, stirs afterwards and heats; Reaction after finishing is removed hydrogen fluoride, and surplus product is made with extra care, and obtains the diaryl hexafluoropropane compound product;
Reaction formula is
Figure GSA00000137866200021
The principle of reaction of the present invention is as described below:
Two reactions that relate among the present invention, first reaction belongs to the Propylene oxide hexafluoride isomerization reaction of Louis acid catalysis, and second reaction belongs to the condensation reaction of Fu-Ke reaction property.Because the mechanism of second reaction is Fu-Ke reaction, is the aromatic hydrocarbon with one or more electron donating groups so require the specific aromatic hydrocarbon as reaction raw materials, such aromatic hydrocarbon just has enough reactive behavioies of carrying out Fu-Ke reaction.Like this specific aromatic hydrocarbon such as phenol, benzene that alkyl replaces such as toluene, o-Xylol, benzene that alkoxyl group replaces such as anisole, phenetole, dialkyl amido benzene such as diethylaniline etc.The aromatic hydrocarbon raw material is identical with traditional technology.
In hydrogen fluoride, under reaction conditions of the present invention, isomerization reaction can take place in Propylene oxide hexafluoride, generates Perfluoroacetone.On reaction mechanism, be because hydrogen fluoride belongs to Lewis acid, and Lewis acid can make Propylene oxide hexafluoride carry out isomerization reaction to Perfluoroacetone rather than five fluorine propionyl fluoride directions under certain condition.
Consequent Perfluoroacetone under the condition of hydrogen fluoride as catalyzer and dewatering agent, and has certain active aromatic hydrocarbon generation condensation reaction, generates diaryl hexafluoropropane compound.This is reflected at and belongs to Fu-Ke reaction on the mechanism.This reactions steps and traditional synthesis of diaryl hexafluoropropane compound basically identical, but because a raw material of reaction is the Perfluoroacetone that a last isomerization reaction produces, rather than the Perfluoroacetone trihydrate that adds in the traditional technology, so can reduce hydrogen fluoride consumption as dewatering agent, and the moisture content number in reaction system is few, thereby hydrogen fluoride is little to the metal protection of reactor.
Used reactor is meant and can tolerates certain temperature and pressure in the technology of the present invention, and the reactor of hydrogen fluoride corrosion, particularly carbon steel, stainless steel, nickel-base alloy steel, or the autoclave class reactor of the metal made of internal surface coating or liner fluoro-resin, precious metal, alloy material.
The ratio of raw material in the technology of the present invention is pressed mass ratio and is calculated, and aromatic hydrocarbon: Propylene oxide hexafluoride: the ratio of anhydrous hydrogen fluoride is generally 1: 0.1-5: 0.1-10, and preferably 1: 0.5-2.5: 0.5-5.If raw material exceeds 1: 0.1-5: the 0.1-10 ratio, productive rate can reduce, but reaction still can take place.
The temperature of reacting in the technology of the present invention is generally at 50 to 200 degrees centigrade, preferably at 80 to 180 degrees centigrade.
The reaction times is generally at 1 to 20 hour, preferably at 2-15 hour in the technology of the present invention.Concrete temperature of reaction and reaction times are generally depended on the reactive behavior of the aromatic hydrocarbon of reaction.
The present invention has following beneficial effect:
1. the synthetic method of diaryl hexafluoropropane compound of the present invention, be to make the Propylene oxide hexafluoride isomerization and merge in the technology to realize (promptly so-called " one pot of change " or one-pot react) with the condensation reaction of aromatic hydrocarbon, thus, reduced the synthetic processing step, reduced production cost and by product and generated.
2. another advantage of the inventive method is, because used Perfluoroacetone trihydrate is by the Propylene oxide hexafluoride isomerization after water absorbs and refining obtaining in the traditional technology, in this process, relate to multiple arrangements such as reactor, water absorption unit, rectifying tower, and pilot process has highly toxic anhydrous Perfluoroacetone, causes environmental protection and safety problem easily; Two are reflected in the reactor order and carry out in the novel process, Perfluoroacetone original position (in situ) that the Propylene oxide hexafluoride isomerization produces and aromatic hydrocarbon reaction have reduced equipment, personnel, energy expenditure and the safety of reacting required and the hidden danger of environmental protection aspect.
3. as seen reaction formula of the present invention and traditional method reactive mode contrast, and the water that produces in the inventive method reaction has lacked 3 parts than traditional technology; As everyone knows, introducing water in anhydrous hydrogen fluoride can increase it greatly to Corrosion of Metallic Materials, and the content of moisture and relevant in this corrodibility and the hydrogen fluoride is so the corrodibility of the inventive method reaction pair reactor can greatly reduce.
Embodiment
Following examples are as the explanation to embodiment of the present invention, but do not limit content of the present invention.(annotate: the calculation of yield in following examples is a benchmark with the aromatic hydrocarbon that drops into.)
Embodiment 1:
400 gram phenol are dropped in 5 liters the nickelalloy steel autoclave, add 1600 gram anhydrous hydrogen fluorides, connect the pipeline with the Propylene oxide hexafluoride steel cylinder then, add 800 gram Propylene oxide hexafluorides by pipeline.Close each charging/discharging valve behind the door, start stirring, be heated to 80 degrees centigrade of internal temperatures, be incubated and stir 20 hours.After reaction finished, the cooling reactor slowly imported reaction product in 10 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used ethyl alcohol recrystallization then, obtains white crystals shape solid, and fusing point is 160 degrees centigrade, and product is a bisphenol AF, and weight is 612 grams, calculates and knows that productive rate is 85.6%.
Embodiment 2:
In the stainless steel autoclave with 200 liters of 50 kilograms of phenol inputs, add 25 kilograms of anhydrous hydrogen fluorides by pipeline, the pipeline of connection and Propylene oxide hexafluoride steel cylinder adds 100 kilograms of Propylene oxide hexafluorides then.Close each charging/discharging valve behind the door, start stirring, be heated to 125 degrees centigrade of internal temperatures, be incubated and stir 12 hours.After reaction finishes, the gasification of hydrogen fluoride in the reactor is absorbed in the receiving tank of peripheral hardware, cool off reactor then, take out solid product to normal temperature, wash neutrality, drying is used ethyl alcohol recrystallization then, obtains white crystals shape solid, fusing point is 161 degrees centigrade, product is a bisphenol AF, and weight is 786 kilograms, calculates and knows that productive rate is 87.9%.
Embodiment 3:
In the stainless steel autoclave with 50 liters of 3 kilograms of toluene inputs, add 20.5 kilograms of anhydrous hydrogen fluorides by pipeline, the pipeline of connection and Propylene oxide hexafluoride steel cylinder adds 6 kilograms of Propylene oxide hexafluorides then.Close each charging/discharging valve behind the door, start stirring, be heated to 150 degrees centigrade of internal temperatures, be incubated and stir 20 hours.After reaction finished, the cooling reactor slowly imported reaction product in 10 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used the Virahol recrystallization then, obtain white crystals shape solid, fusing point is 85 degrees centigrade, determines that by analysis product is 2,2-two (4-aminomethyl phenyl)-HFC-236fa, weight is 4.23 kilograms, calculates and knows that productive rate is 78.1%.
Embodiment 4:
In the stainless steel high-voltage device with 10 liters of 3.4 kilograms of o-Xylols inputs, add 3.1 kilograms of anhydrous hydrogen fluorides, the pipeline of connection and Propylene oxide hexafluoride steel cylinder adds 2.8 kilograms of Propylene oxide hexafluorides then.Close each charging/discharging valve behind the door, start stirring, be heated to 175 degrees centigrade of internal temperatures, be incubated and stir 11 hours.After reaction finished, cooling reactor slowly imported reaction product in 10 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used the ethylene dichloride recrystallization then, obtain white crystals shape solid, fusing point is 76 degrees centigrade, determines that by analysis product is 2, and 2-two (3, the 4-aminomethyl phenyl)-and HFC-236fa, weight is 4.92 kilograms, calculates and knows that productive rate is 85.2%.
Embodiment 5:
In the stainless steel high-voltage device with 10 liters of 3.6 kilograms of anisoles inputs, add 1.8 kilograms of anhydrous hydrogen fluorides, the pipeline of connection and Propylene oxide hexafluoride steel cylinder adds 7 kilograms of Propylene oxide hexafluorides then.Close each charging/discharging valve behind the door, start stirring, be heated to 200 degrees centigrade of internal temperatures, be incubated and stir 1 hour.After reaction finished, cooling reactor slowly imported reaction product in 10 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used the isopropyl ether recrystallization then, obtain white crystals shape solid, fusing point is 71 degrees centigrade, determines that by analysis product is 2,2-two (4-p-methoxy-phenyl)-HFC-236fa, weight is 2.65 kilograms, calculates and knows that productive rate is 43.7%.
Embodiment 6:
1000 gram phenol are dropped in 2 liters the carbon steel autoclave of lined with fluoroplastic material, add 100 gram anhydrous hydrogen fluorides, connect the pipeline with the Propylene oxide hexafluoride steel cylinder then, add 100 gram Propylene oxide hexafluorides by pipeline.Close each charging/discharging valve behind the door, start stirring, be heated to 50 degrees centigrade of internal temperatures, be incubated and stir 20 hours.After reaction finished, the cooling reactor slowly imported reaction product in 5 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used ethyl alcohol recrystallization then, obtains white crystals shape solid, and fusing point is 159 degrees centigrade, and product is a bisphenol AF, and weight is 197 grams, calculates and knows that productive rate is 11.0%.
Embodiment 7:
100 gram phenol are dropped in 2 liters the stainless steel autoclave, add 1000 gram anhydrous hydrogen fluorides, connect the pipeline with the Propylene oxide hexafluoride steel cylinder then, add 500 gram Propylene oxide hexafluorides by pipeline.Close each charging/discharging valve behind the door, start stirring, be heated to 200 degrees centigrade of internal temperatures, be incubated and stir 1 hour.After reaction finished, the cooling reactor slowly imported reaction product in 5 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used ethyl alcohol recrystallization then, obtains white crystals shape solid, and fusing point is 161 degrees centigrade, and product is a bisphenol AF, and weight is 171 grams, calculates and knows that productive rate is 95.7%.
Embodiment 8:
1000 gram phenol are dropped in 10 liters the carbon steel autoclave of lining nickel-base alloy hastelloy, add 100 gram anhydrous hydrogen fluorides, connect the pipeline with the Propylene oxide hexafluoride steel cylinder then, add 5000 gram Propylene oxide hexafluorides by pipeline.Close each charging/discharging valve behind the door, start stirring, be heated to 110 degrees centigrade of internal temperatures, be incubated and stir 20 hours.After reaction finished, the cooling reactor slowly imported reaction product in 15 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used ethyl alcohol recrystallization then, obtains white crystals shape solid, and fusing point is 159 degrees centigrade, and product is a bisphenol AF, and weight is 1120 grams, calculates and knows that productive rate is 62.7%.
Embodiment 9:
500 gram phenol are dropped in 10 liters the carbon steel autoclave of lined with fluoroplastic material, add 5000 gram anhydrous hydrogen fluorides, connect the pipeline with the Propylene oxide hexafluoride steel cylinder then, add 50 gram Propylene oxide hexafluorides by pipeline.Close each charging/discharging valve behind the door, start stirring, be heated to 78 degrees centigrade of internal temperatures, be incubated and stir 15 hours.After reaction finished, the cooling reactor slowly imported reaction product in 20 liters of cold water to normal temperature, and visible product solid is separated out; Filter out solid product, wash neutrality, drying is used ethyl alcohol recrystallization then, obtains white crystals shape solid, and fusing point is 160 degrees centigrade, and product is a bisphenol AF, and weight is 93 grams, calculates and knows that productive rate is 10.4%.

Claims (4)

1. the synthetic method of a diaryl hexafluoropropane compound is characterized in that, the aromatic hydrocarbon that will have one or more electron donating groups mixes in reactor earlier with anhydrous hydrogen fluoride, adds Propylene oxide hexafluoride then, stirs afterwards and heats; Reaction after finishing is removed hydrogen fluoride, and surplus product is made with extra care, and obtains the diaryl hexafluoropropane compound product;
Reaction formula is
Figure FSA00000137866100011
2. the synthetic method of diaryl hexafluoropropane compound as claimed in claim 1 is characterized in that, aromatic hydrocarbon: Propylene oxide hexafluoride: anhydrous hydrogen fluoride is 1 by mass ratio: 0.1-5: 0.1-10.
3. the synthetic method of diaryl hexafluoropropane compound as claimed in claim 1 or 2 is characterized in that, the temperature of reaction is 50 to 200 degrees centigrade.
4. the synthetic method of diaryl hexafluoropropane compound as claimed in claim 1 or 2 is characterized in that, the reaction times is 1 to 20 hour.
CN201010189099A 2010-06-01 2010-06-01 Synthesis method of diaryl hexafluoropropane compound Pending CN101851147A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104326882A (en) * 2014-11-27 2015-02-04 三明市海斯福化工有限责任公司 Method for synthesizing diaryl hexafluoropropane compound
CN104326873A (en) * 2014-09-24 2015-02-04 东莞市长安东阳光铝业研发有限公司 Preparation method of 2-(3,4-ditolyl)-1,1,1,3,3,3-hexafluoro-2-propanol
CN104370669A (en) * 2014-11-27 2015-02-25 三明市海斯福化工有限责任公司 Synthesis method of diaryl hexafluoropropane compound
CN104496763A (en) * 2014-11-27 2015-04-08 三明市海斯福化工有限责任公司 Method for synthesizing diaryl hexafluoropropane compound

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3321515A (en) * 1963-04-24 1967-05-23 Du Pont Method of making fluorinated carbonyl compounds
US4358624A (en) * 1980-12-31 1982-11-09 General Electric Company Fluorinated monophenols and diphenols and method for their preparation
US4400546A (en) * 1980-12-11 1983-08-23 Hoechst Aktiengesellschaft Process for the preparation of hexafluoroacetone and direct use of the solution obtained by the process

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3321515A (en) * 1963-04-24 1967-05-23 Du Pont Method of making fluorinated carbonyl compounds
US4400546A (en) * 1980-12-11 1983-08-23 Hoechst Aktiengesellschaft Process for the preparation of hexafluoroacetone and direct use of the solution obtained by the process
US4358624A (en) * 1980-12-31 1982-11-09 General Electric Company Fluorinated monophenols and diphenols and method for their preparation

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104326873A (en) * 2014-09-24 2015-02-04 东莞市长安东阳光铝业研发有限公司 Preparation method of 2-(3,4-ditolyl)-1,1,1,3,3,3-hexafluoro-2-propanol
CN104326882A (en) * 2014-11-27 2015-02-04 三明市海斯福化工有限责任公司 Method for synthesizing diaryl hexafluoropropane compound
CN104370669A (en) * 2014-11-27 2015-02-25 三明市海斯福化工有限责任公司 Synthesis method of diaryl hexafluoropropane compound
CN104496763A (en) * 2014-11-27 2015-04-08 三明市海斯福化工有限责任公司 Method for synthesizing diaryl hexafluoropropane compound
CN104370669B (en) * 2014-11-27 2016-03-30 三明市海斯福化工有限责任公司 A kind of synthetic method of diaryl hexafluoropropane compound
CN104326882B (en) * 2014-11-27 2016-06-08 三明市海斯福化工有限责任公司 A kind of synthetic method of diaryl hexafluoropropane compound

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