CN109096087A - A kind of preparation method of trifluoroacetic acid - Google Patents
A kind of preparation method of trifluoroacetic acid Download PDFInfo
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- CN109096087A CN109096087A CN201811053778.3A CN201811053778A CN109096087A CN 109096087 A CN109096087 A CN 109096087A CN 201811053778 A CN201811053778 A CN 201811053778A CN 109096087 A CN109096087 A CN 109096087A
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- trifluoroacetic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Abstract
The invention discloses a kind of preparation methods of trifluoroacetic acid, include the following steps: (1) 1, and the fixed bed reactors equipped with catalyst, gas phase chlorination reaction 1,1,1- tri- fluoro- 2,2- dichloroethanes of synthesis are entered after 1,1- trifluoro-2-chloroethane and chlorine vaporization；After (2) 1,1,1- tri- fluoro- 2,2- dichloroethanes and oxygen vaporization, oxidation reaction obtains trifluoro-acetyl chloride under light source effect, returns to reactor after unreacted 1,1,1- tri- fluoro- 2,2- dichloroethanes condensation；(3) trifluoro-acetyl chloride hydrolyzes to obtain trifluoroacetic acid.The present invention has many advantages, such as that simple process, high income, the three wastes are few, and reaction conversion ratio is high, and selectivity is high, reacts continuous production, safety and environmental protection.
Description
Technical field
The invention belongs to chemical fields, and in particular to a kind of preparation method of trifluoroacetic acid.
Background technique
Trifluoroacetic acid: nickname TFA, CAS 76-05-1, English name trifluoroacetic acid, molecular weight
114.02, -15.2 DEG C of fusing point, 72.4 DEG C of boiling point, density 1.535g/cm3, water-soluble, aqueous solution highly acid.It is many organic
The good solvent of compound, such as shares with carbon disulfide, can dissolve protein.It is also the fine solvent of organic reaction, can be obtained
Be difficult to obtain in common solvent as a result, for example in common solvent when catalytic hydrogenation, pyridine ring preferentially hydrogenates quinoline, but
Phenyl ring preferentially hydrogenates in trifluoroacetic acid.Trifluoroacetic acid resolves into fluoroform and carbon dioxide in the presence of aniline.
The production technology of trifluoroacetic acid is more, and (1) for raw material, is being urged with 1,1,1- trifluoro-2-chloroethane (HCFC-123)
Under the action of change, HCFC-123 is direct oxidation into trifluoroacetic acid and trifluoro-acetyl chloride using oxygen, which needs in high temperature
It is carried out under high pressure, reaction temperature needs 250~320 DEG C, and reaction pressure needs 2.5~3.5Mpa.(2) with trifluorotrichloroethane
(HCFC-113a) and SO3For raw material, the route of catalyst is made of mereurous sulfate, is oxidized to trifluoro-acetyl chloride, and second step is hydrolyzed to
Trifluoroacetic acid product.The process route uses SO3Equal hazardous chemicals, and need to use during the preparation process to use toxic mercury salt
As catalyst, there are biggish safety and environmentally friendly hidden danger.The most mature route of industrialization is with the fluoro- 2- chlorine of 1,1,1- tri- at present
Ethane (HCFC-133a) is raw material, and chlorination synthesizes 1,1,1- tri- fluoro- 2,2- dichloroethanes (HCFC-123), then reoxidizes conjunction
At trifluoro-acetyl chloride (TFAC), hydrolysis obtains product trifluoroacetic acid (TFA).
There are three types of process routes for HCFC-133a chlorination: (1) liquid phase thermal chlorination: by HCFC-33a and chlorine in reactor
Middle contact progress chlorination, catalyst choice azodiisobutyronitrile, liquid phase reactor, pressure 5 to 15bar, 80 to 110 DEG C of temperature, chlorine
With 1~2:1 of HCFC-133a molar ratio.(2) gas-phase catalysis: HCFC-133a and chlorine are passed through the reactor equipped with catalyst
In, reaction obtains R123 under certain temperature, molar ratio, and catalyst is typically chosen carrier AlF3Load NiCl2、CuCl2
Deng；(3) light chlorination process: HCFC-133a and chlorine are reacted under ultraviolet light or white light.
Aoxidizing preparation TFAC with HCFC-123, there are mainly three types of process routes: (1) liquid phase oxidation: reaction pressure is high, item
Part is harsh, very high to equipment requirement, it is difficult to realize industrialization；(2) catalytic gas phase oxidation method: HCFC-123 and oxygen are passed through
It is aoxidized in reactor equipped with catalyst, catalyst choice active carbon or its metal-supported catalyst, selectivity of product
Difference, catalyst life are short；(3) photooxidation method: trifluoro will be obtained in reactor that HCFC-123 and oxygen are passed through under illumination condition
Chloroacetic chloride, reaction temperature, pressure are low.
United States Patent (USP) US5414166 provides a kind of preparation method of 1,1,1- tri- fluoro- 2,2- dichloroethanes, the invention
With HCFC-133a and Cl2、H2HCFC-123 is prepared under activated carbon catalysis effect.Reaction condition: 350~450 DEG C, time of contact
15~45s, Cl2/ HCFC-133a molar ratio 1~5:1, H2/ HCFC-133a 0.5~3:1 of molar ratio, 8~10atm of pressure, reaction
Equipment matter Inconel600 or Hastelloy or nickel, conversion ratio 42~79%, selectivity 76~92%.The invention is passed through H2Purpose
It is to improve HCFC-123 selectivity to reduce trifluorotrichloroethane (HCFC-113a) and generate.The technological reaction temperature is high, work
Skill is complicated, and catalyst easily ties carbon inactivation.
Patent CN200910156965, CN200910155787 is reported with HCFC-123 or trifluoroethane chlorinated mixture
It for raw material, is passed through in the enamel still equipped with mercury lamp with oxygen, chlorine, reaction product is discharged from upper gaseous phase.Reaction temperature 10~
35 DEG C, 0.02~0.5MPa of pressure, chlorine plays initiation, and by-product is mainly HCFC-113a.
Patent US5569782A, it discloses the light of HCFC-123 and chlorine more than wavelength 290nm and irradiates to obtain trifluoro second
Acyl chlorides.50~130 DEG C of reaction temperature, HCFC-123/O2For 1:1.2, Cl is passed through in reaction process2。
Patent US5241113 report, HCFC-123 and oxygen are by active carbon in 250-300 DEG C, time of contact 10-60s
Gas phase reaction.Reactor material C-276, Inconel600.HCFC-123 conversion ratio 100%, trifluoro-acetyl chloride selectivity about 45%.
Summary of the invention
To solve the above-mentioned problems, the present invention provides a kind of preparation method of trifluoroacetic acid.
The present invention is achieved by the following technical solutions:
A kind of preparation method of trifluoroacetic acid, comprising the following steps:
(1) with 1,1,1- trifluoro-2-chloroethane and chlorine for raw material, under the effect of the catalyst, under certain reaction condition,
Gas phase chlorination synthesizes the fluoro- 2,2- dichloroethanes of 1,1,1- tri-；
After (2) 1,1,1- tri- fluoro- 2,2- dichloroethanes and oxygen mix vaporization, it is passed through in the gas-phase reactor equipped with light source, sends out
Raw oxidation reaction obtains trifluoro-acetyl chloride；
(3) trifluoro-acetyl chloride is passed through in water and is reacted with water, obtained trifluoroacetic acid and hydrogen chloride, trifluoro second is obtained after separation
Acid product.
Preferably, catalyst is the metal of load iron, copper and chromium using active carbon and/or aluminum fluoride as carrier in step (1)
Chloride is made.It is highly preferred that copper chloride in step (1), iron chloride and the total load capacity of chromium chloride are 1~5wt.%.
Preferably, the temperature reacted in step (1) is 260~300 DEG C, and chlorine and 1,1,1- trifluoro-2-chloroethane rubs
, than being 1~2:1, air speed is 600~1000h for you-1。
Preferably, in step (2) 1,1,1- tri- fluoro- 2,2- dichloroethanes and oxygen according to the mixed steam of molar ratio 1:1~2
Change, is passed through in the reactor equipped with the built-in double-deck cooling light source and carries out, contain the anti-of trifluoro-acetyl chloride, hydrogen chloride and excessive oxygen
Object is answered continuously to be discharged from reactor top, 5~20 DEG C of reaction temperature.
Preferably, 1,1,1- tri- fluoro- 2,2- dichloroethanes, trifluoro-acetyl chloride, chlorination are contained in reactor top in step (2)
The reactant of hydrogen and excessive oxygen is separated through knockout tower, and tower top obtains product trifluoro-acetyl chloride, and tower reactor has 1,1,1- tri- fluoro- 2,
The reaction was continued for 2- dichloroethanes Returning reactor, and hydrogen chloride water absorbs.
It is highly preferred that light source is mercury lamp, Metal halogen lamp or xenon lamp in step (2).
Preferably, reaction temperature is 30~60 DEG C in step (3), 40~100h of air speed-1。
HCFC-133a and chlorine reaction are gas-solid phase reactions in step (1), and catalyst choice support type, load capacity is more, urges
Agent activity is good, it may occur that superchlorination reaction obtains HCFC-113a, and load capacity is low, and conversion ratio is low.Second step photooxidation is anti-
It answers, enters reactor after HCFC-123 and oxygen vaporization, exterior light is shone, and has been reacted gas phase trifluoro-acetyl chloride and has been arranged from reactor top
Out, the liquid level of reactor is controlled by the way that HCFC-123 is added.
Beneficial effect
Compared with prior art, the invention has the following advantages that
1, simple process, high income, the three wastes are few；
2, first step reaction conversion ratio > 50%, selective > 99.5%, second step react continuous production, catalyst are not added, safety
Environmental protection.
Detailed description of the invention
Fig. 1 is process flow chart of the invention.
As shown in the figure: 1 is chlorination reactor, and 2 be first rectifying column, and 3 be Second distillation column, and 4 be photooxidation integrated reaction
Device, 5 be hydrolysis reactor.
Specific embodiment
It elaborates below to the embodiment of the present invention, the present embodiment carries out under the premise of the technical scheme of the present invention
Implement, the detailed implementation method and specific operation process are given, but protection scope of the present invention is not limited to following implementation
Example.
It is passed through chlorination reactor 1 after raw material HCFC-133a and chlorine vaporization, the material of reactor outlet enters the first rectifying
Tower 2 separates, and tower top is chlorine and HCl, and tower reactor contains HCFC-123, a small amount of HCFC-113a and unreacted HCFC-133a enters
Second distillation column 3 is separated, and tower top obtains HCFC-133a, returns to chlorination reactor, the HCFC-123 of tower reactor, a small amount of
HCFC-113a and fresh oxygen enter photooxidation reaction device 4, and the TFAC reacted is discharged on the top of reactor, into water
Reactor 5 is solved, TFA and HCl is obtained, product TFA is obtained after separation.
Below by embodiment, present invention is further described in detail, but the present invention is not limited to the embodiment described.
Embodiment 1
First by 20ml CuCl2/FeCl3/CrCl3/ C(CuCl2Load capacity be 2wt.%, FeCl3Load capacity be 2wt.%,
CrCl3Load capacity be 0.5wt.%) catalyst is fitted into chlorination reactor, is warming up to 260 DEG C, feed intake reaction, chlorine with
The molar ratio of HCFC-133a is 1.5:1, air speed 600h-1, reactor outlet sampling analysis, the conversion ratio of HCFC-133a
The selectivity 99.7% of 64.8%, HCFC-123, the selectivity 0.3% of HCFC-113a.
HCFC-123 and oxygen are to enter photooxidation integrated reactor after the mixing vaporization of 1:2 molar ratio, and 5 DEG C of reaction temperature,
Light source is mercury lamp.Sampling analysis after reaction 1 hour, selectivity 99.8% of the HCFC-123 conversion ratio up to 92.8%, TFAC.
The TFAC that second step is reacted is passed through in water, and 40 DEG C of temperature, air speed 40h-1, it absorbs 2 hours, sampling analysis,
Obtain the TFA that purity is 99.8%.
Embodiment 2
First by 20ml CuCl2/FeCl3/CrCl3/ C(CuCl2Load capacity be 1wt.%, FeCl3Load capacity be 2wt.%,
CrCl3Load capacity be 2wt.%) catalyst is fitted into chlorination reactor, be warming up to 300 DEG C, feed intake reaction, chlorine and HCFC-
The molar ratio of 133a is 2:1, air speed 600h-1, reactor outlet sampling analysis, the conversion ratio 55% of HCFC-133a, HCFC-
123 selectivity 99.3%, the selectivity 0.7% of HCFC-113a.
HCFC-123 and oxygen are to enter photooxidation integrated reactor after the mixing vaporization of 1:1 molar ratio, and 15 DEG C of reaction temperature,
Light source is mercury lamp.Sampling analysis after reaction 1 hour, selectivity 99.5% of the HCFC-123 conversion ratio up to 93.6%, TFAC.
The TFAC that second step is reacted is passed through in water, temperature 60 C, air speed 100h-1, it absorbs 2 hours, sampling analysis,
Obtain the TFA that purity is 99.8%.
Embodiment 3
First by 20ml CuCl2/FeCl3/CrCl3/ C(CuCl2Load capacity be 1wt.%, FeCl3Load capacity be 0.5wt.%,
CrCl3Load capacity be 0.5wt.%) catalyst is fitted into chlorination reactor, is warming up to 280 DEG C, feed intake reaction, chlorine with
The molar ratio of HCFC-133a is 1:1, air speed 1000h-1, reactor outlet sampling analysis, the conversion ratio of HCFC-133a
The selectivity 99.2% of 75.3%, HCFC-123, the selectivity 0.8% of HCFC-113a.
HCFC-123 and oxygen are to enter photooxidation integrated reactor, reaction temperature 10 after the mixing vaporization of 1:1.5 molar ratio
DEG C, light source is Metal halogen lamp.Sampling analysis after reaction 1 hour, selectivity 99.4% of the HCFC-123 conversion ratio up to 85.6%, TFAC.
The TFAC that second step is reacted is passed through in water, and 30 DEG C of temperature, air speed 60h-1, it absorbs 2 hours, sampling analysis,
Obtain the TFA that purity is 99.8%.
Embodiment 4
First by 20ml CuCl2/FeCl3/CrCl3/ AlF3(CuCl2Load capacity be 0.5wt.%, FeCl3Load capacity be
0.3wt.%, CrCl3Load capacity be 0.2wt.%) catalyst is fitted into chlorination reactor, be warming up to 280 DEG C, feed intake reaction, chlorine
The molar ratio of gas and HCFC-133a are 1.5:1, air speed 800h-1, reactor outlet sampling analysis, the conversion ratio of HCFC-133a
The selectivity 99.4% of 72.5%, HCFC-123, the selectivity 0.6% of HCFC-113a.
HCFC-123 and oxygen are to enter photooxidation integrated reactor, reaction temperature 20 after the mixing vaporization of 1:1.5 molar ratio
DEG C, light source is xenon lamp.Sampling analysis after reaction 1 hour, selectivity 99.4% of the HCFC-123 conversion ratio up to 78.3%, TFAC.
The TFAC that second step is reacted is passed through in water, temperature 50 C, air speed 80h-1, it absorbs 2 hours, sampling analysis,
Obtain the TFA that purity is 99.8%.
Embodiment 5
First by 20ml CuCl2/FeCl3/CrCl3/AlF3(CuCl2Load capacity be 2wt.%, FeCl3Load capacity be
0.5wt.%, CrCl3Load capacity be 0.5wt.%) catalyst is fitted into chlorination reactor, be warming up to 280 DEG C, feed intake reaction, chlorine
The molar ratio of gas and HCFC-133a are 2:1, air speed 600h-1, reactor outlet sampling analysis, the conversion ratio of HCFC-133a
The selectivity 98.7% of 66.8%, HCFC-123, the selectivity 1.3% of HCFC-113a.
HCFC-123 and oxygen are to enter photooxidation integrated reactor, reaction temperature 15 after the mixing vaporization of 1:1.5 molar ratio
DEG C, light source is Metal halogen lamp.Sampling analysis after reaction 1 hour, selectivity 99.6% of the HCFC-123 conversion ratio up to 81.4%, TFAC.
The TFAC that second step is reacted is passed through in water, and 40 DEG C of temperature, air speed 40h-1, it absorbs 2 hours, sampling analysis,
Obtain the TFA that purity is 99.8%.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
Mind and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to include these modifications and variations.
Claims (8)
1. a kind of preparation method of trifluoroacetic acid, which comprises the following steps:
(1) with 1,1,1- trifluoro-2-chloroethane and chlorine for raw material, under the effect of the catalyst, under certain reaction condition,
Gas phase chlorination synthesizes the fluoro- 2,2- dichloroethanes of 1,1,1- tri-；
After (2) 1,1,1- tri- fluoro- 2,2- dichloroethanes and oxygen mix vaporization, it is passed through in the gas-phase reactor equipped with light source, sends out
Raw oxidation reaction obtains trifluoro-acetyl chloride；
(3) trifluoro-acetyl chloride is passed through in water and is reacted with water, obtained trifluoroacetic acid and hydrogen chloride, trifluoro second is obtained after separation
Acid product.
2. a kind of preparation method of trifluoroacetic acid according to claim 1, which is characterized in that catalyst is in step (1)
Using active carbon and/or aluminum fluoride as carrier, the metal chloride of load iron, copper and chromium is made.
3. a kind of preparation method of trifluoroacetic acid according to claim 2, which is characterized in that copper chloride, chlorine in step (1)
Change iron and the total load capacity of chromium chloride is 1~5wt.%.
4. a kind of preparation method of trifluoroacetic acid according to claim 1, which is characterized in that the temperature reacted in step (1)
Degree is 260~300 DEG C, chlorine and 1, and the molar ratio of 1,1- trifluoro-2-chloroethane is 1~2:1, and air speed is 600~1000h-1。
5. a kind of preparation method of trifluoroacetic acid according to claim 1, which is characterized in that 1,1,1- tri- in step (2)
Fluoro- 2,2- dichloroethanes and oxygen are mixed according to molar ratio 1:1~2 to be vaporized, and the reaction equipped with the built-in double-deck cooling light source is passed through
It is carried out in device, the reactant containing trifluoro-acetyl chloride, hydrogen chloride and excessive oxygen is continuously discharged from reactor top, reaction temperature
5~20 DEG C.
6. a kind of preparation method of trifluoroacetic acid according to claim 1, which is characterized in that in step (2) on reactor
Contain the reactant of the fluoro- 2,2- dichloroethanes of 1,1,1- tri-, trifluoro-acetyl chloride, hydrogen chloride and excessive oxygen through knockout tower point in portion
From, tower top obtains product trifluoro-acetyl chloride, and the reaction was continued for 1,1,1- tri- fluoro- 2, the 2- dichloroethanes Returning reactor that has of tower reactor,
Hydrogen chloride water absorbs.
7. a kind of preparation method of trifluoroacetic acid according to claim 1 or 5, which is characterized in that light source is in step (2)
Mercury lamp, Metal halogen lamp or xenon lamp.
8. a kind of preparation method of trifluoroacetic acid described in one of -6 according to claim 1, which is characterized in that anti-in step (3)
Answering temperature is 30~60 DEG C, 40~100h of air speed-1。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111039771A (en) * | 2019-12-25 | 2020-04-21 | 湖南有色郴州氟化学有限公司 | Preparation method of 3,3, 3-trifluoropropionic acid |
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| US5041647A (en) * | 1984-05-15 | 1991-08-20 | Asahi Glass Co., Ltd. | Process for producing trifluoroacetic acid and trifluoroacetyl chloride |
| US5296640A (en) * | 1992-09-15 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Process for preparing perhaloacyl chlorides |
| US5315044A (en) * | 1988-05-17 | 1994-05-24 | Daikin Industries Ltd. | Process for production of 1,1,1-trifluoro-2,2-dichloroethane |
| US5545298A (en) * | 1993-08-13 | 1996-08-13 | Solvay Fluor Und Derivate Gmbh | Process for preparing polyfluorocarboxylic acid chlorides and perfluorocarboxylic acid chlorides |
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| US3883407A (en) * | 1973-04-20 | 1975-05-13 | Halocarbon Prod Corp | Production of 2,2,2-trifluoroacetyl chloride |
| US5041647A (en) * | 1984-05-15 | 1991-08-20 | Asahi Glass Co., Ltd. | Process for producing trifluoroacetic acid and trifluoroacetyl chloride |
| US5315044A (en) * | 1988-05-17 | 1994-05-24 | Daikin Industries Ltd. | Process for production of 1,1,1-trifluoro-2,2-dichloroethane |
| US5296640A (en) * | 1992-09-15 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Process for preparing perhaloacyl chlorides |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111039771A (en) * | 2019-12-25 | 2020-04-21 | 湖南有色郴州氟化学有限公司 | Preparation method of 3,3, 3-trifluoropropionic acid |
| CN111039771B (en) * | 2019-12-25 | 2022-06-03 | 湖南有色郴州氟化学有限公司 | Preparation method of 3,3, 3-trifluoropropionic acid |
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