CN107759451A - A kind of method for synthesizing Hexafluoro acetone and the method for synthesizing hexafluoroisopropanol - Google Patents
A kind of method for synthesizing Hexafluoro acetone and the method for synthesizing hexafluoroisopropanol Download PDFInfo
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- CN107759451A CN107759451A CN201711103212.2A CN201711103212A CN107759451A CN 107759451 A CN107759451 A CN 107759451A CN 201711103212 A CN201711103212 A CN 201711103212A CN 107759451 A CN107759451 A CN 107759451A
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Abstract
The invention provides a kind of method for synthesizing Hexafluoro acetone and the method for synthesizing hexafluoroisopropanol.A kind of method for synthesizing Hexafluoro acetone, comprises the following steps：Make hexachloroacetone and hydrogen fluoride that first step substitution reaction occur in the presence of the first catalyst, generate the first product, the temperature of the first step substitution reaction is 70~80 DEG C, and first catalyst is trivalent chromium compound；Make first product and hydrogen fluoride that second step substitution reaction occur in the presence of the second catalyst, generate Hexafluoro acetone, the temperature of the second step substitution reaction is 350~400 DEG C, and second catalyst includes trivalent chromium compound.Synthesis hexafluoroisopropanol be more than on the basis of restore hydrogenation.The present invention solves the problems, such as easily to tie carbon in traditional handicraft.
Description
Technical field
The present invention relates to chemical technology field, more particularly, to a kind of method for synthesizing Hexafluoro acetone and synthesis hexafluoro isopropyl
The method of alcohol.
Background technology
Hexafluoroisopropanol (i.e. HFIP) is a kind of new fluorochemical, is a kind of highly polar solvent, with water and perhaps
More organic solvents are easy to mix, and heat endurance is good, and good for the permeability of ultraviolet light, and these characteristics make answering for HFIP
With very extensive.For example, HFIP can turn into a kind of ideal solvent in many polymerization systems；HFIP is also served as in pharmaceuticals
Mesosome, suction-type anesthetic sevoflurane, and the intermediate of synthesis agricultural chemicals can be synthesized；HFIP may be used as electronics side
The solvent cleaner in face；HFIP can dissolve substantial portion of polymer, as polyester, polyamide, polyacrylonitrile, polyacetals and
Hydrolysising polyethylene ester etc., because such property can obtain application well in terms of analysis and be used as high polymer sharp again
Regenerative agent.
HFIP synthesis uses below scheme more：Acetone and chlorine reaction generation hexachloroacetone, hexachloroacetone is directly and fluorine
Change hydrogen reaction generation Hexafluoro acetone, reduction reaction generation hexafluoroisopropanol occurs for Hexafluoro acetone.In conventional art, hexachloroacetone with
The process of hydrogen fluoride reaction generation Hexafluoro acetone is in high temperature (350~450 DEG C) and catalyst (generally trivalent chromium compound)
Condition is completed in next step, because reaction temperature is too high (350-370 DEG C), is easily caused carbonization to cause catalyst poisoning, is added
Production cost.
In view of this, it is special to propose the present invention.
The content of the invention
The first object of the present invention is to provide a kind of method for synthesizing Hexafluoro acetone, this method solve in traditional handicraft
The problem of easily tying carbon.
The second object of the present invention is to provide a kind of method for synthesizing hexafluoroisopropanol, this method compared to existing process into
This reduction.
In order to realize the above object the invention provides following technical scheme：
A kind of method for synthesizing Hexafluoro acetone, comprises the following steps：
Make hexachloroacetone and hydrogen fluoride that first step substitution reaction, the production of generation first occur in the presence of the first catalyst
Thing, the temperature of the first step substitution reaction is 70~80 DEG C, and first catalyst is trivalent chromium compound；
Make first product and hydrogen fluoride that second step substitution reaction occur in the presence of the second catalyst, generate hexafluoro
Acetone, the temperature of the second step substitution reaction is 350~400 DEG C, and second catalyst includes trivalent chromium compound.
Difference with the prior art of the present invention is that a step substitution reaction is changed into two step substitution reactions, is by chlordene third first
Part chlorine atom substitution in ketone, generates trifluoro trichloroacetone and tetrafluoro dichloroacetone, then again by both compounds
Chlorine atom is all substituted by fluorine, obtains Hexafluoro acetone.Because in above-mentioned flow, the temperature of first step substitution reaction is extremely low, will not
Carbonization, it would not also cause catalyst poisoning, and the fluoro thing (trifluoro trichloroacetone and tetrafluoro dichloroacetone) generated is all resistance to
It high temperature, will not be carbonized at 350~400 DEG C, therefore carbonization problem is also not present in second step substitution reaction.To sum up, it is of the invention
After substitution reaction is divided into the progress of two steps, carbonization problem is avoided, catalyst poisoning phenomenon is eliminated, is produced into so as to reduce
This.
In addition, the method for the present invention can be at least up to the level suitable with prior art in terms of other benefits, for example,
The yield of Hexafluoro acetone can reach more than 90% in the present invention, and existing single step reaction is only capable of reaching 70~80%.
The above method of the present invention can also be improved from the following aspect, as described below.
Preferably, the weight of first catalyst and the volume ratio of the hexachloroacetone are 3~4g：500mL.
Through investigating, when adding 3~4g catalyst in every 500mL hexachloroacetones, trifluoro trichloroacetone and tetrafluoro dichloro third
The yield of ketone is higher, and accessory substance is few.Specifically, in per 500mL hexachloroacetones, can add 3g, 3.2g, 3.5g, 3.6g, 3.8g or
4g catalyst.First catalyst can be arbitrary trivalent chromium compound, such as common chrome green.
Preferably, in the first step substitution reaction, the volume ratio of the hydrogen fluoride and the hexachloroacetone for 1~
1.5:2。
Through investigating, hydrogen fluoride is added in every 2mL hexachloroacetones, and controlling reaction temperature is 70~80 DEG C, hexachloroacetone
Part substitution reaction occurs, for product based on tetrafluoro dichloroacetone, trifluoro trichloroacetone is pair.
Preferably, the time of the first step substitution reaction is 2~3 hours.
Preferably, rectifying, extraction therein three are also carried out to first product before the second step substitution reaction
Fluorine trichloroacetone and tetrafluoro dichloroacetone.
The yield of second step substitution reaction can be improved by rectifying extraction, avoids accessory substance disturbing reaction from carrying out.
Preferably, in the second step substitution reaction, the weight of second catalyst and the first described product
Volume ratio is 2~4g：100mL.
Through investigating, when adding 2~3g catalyst per the products of 100mL first, the yield of Hexafluoro acetone is higher, and accessory substance is few.
Specifically, per in the products of 100mL first, 2g, 2.2g, 2.5g, 2.6g, 2.8g or 3g catalyst can be added.First catalyst
Can be arbitrary trivalent chromium compound, such as common chrome green.
Preferably, second catalyst also contains palladium bichloride.
Trivalent chromium compound and palladium bichloride synergy can improve yield.
Preferably, in the second step substitution reaction, the volume ratio of the hydrogen fluoride and first product is 1~1.5:
1。
Through investigating, hydrogen fluoride is added in every products of 2mL first, and controlling reaction temperature is 350~370 DEG C, hexafluoro third
The yield of ketone is higher.
Preferably, the time of the second step substitution reaction is 50 minutes~100 minutes.
After second step substitution reaction, product is purified, preferable method of purification is：
First rectifying, gaseous Hexafluoro acetone is passed through in water again by rectifying and forms Hexafluoro acetone trihydrate continuation essence
Evaporate to obtain high-purity Hexafluoro acetone trihydrate.
Preferably, the first step substitution reaction and the second step substitution reaction are reacted in microreactor, are passed through
Improve raw material contacting efficiency and improve yield.
Present invention also offers the synthetic method of hexafluoroisopropanol：
Hexafluoro acetone is made first with method as discussed above, then makes it that reduction reaction occur with hydrogen, generates hexafluoro
Isopropanol.
As described above, carbon problem is finished due to eliminating, therefore the method cost of the synthesis hexafluoroisopropanol is greatly reduced.
Preferably, the condition of the reduction reaction is：
Pressure is 0.4~0.6MPa, temperature is 60~80 DEG C.
Preferably, the condition of the reduction reaction is：Back flow reaction more than 8 hours.
To sum up, compared with prior art, invention achieves following technique effect：
(1) knot carbon problem during hexachloroacetone synthesis Hexafluoro acetone is eliminated：
Hexachloroacetone is first converted into fluoride at low temperature, avoids finishing carbon using the high-temperature stability of fluoride and asks
Topic；
(2) production cost reduces：Due to solving the problems, such as catalyst poisoning, therefore save the cost of more catalyst changeout；
(3) yield of Hexafluoro acetone is improved.
Brief description of the drawings
, below will be to specific in order to illustrate more clearly of the specific embodiment of the invention or technical scheme of the prior art
The required accompanying drawing used is briefly described in embodiment or description of the prior art, it should be apparent that, in describing below
Accompanying drawing is some embodiments of the present invention, for those of ordinary skill in the art, before creative work is not paid
Put, other accompanying drawings can also be obtained according to these accompanying drawings.
Fig. 1 is the flow chart for the synthesis hexafluoroisopropanol that the embodiment of the present invention 1 provides.
Embodiment
Technical scheme is clearly and completely described below in conjunction with the drawings and specific embodiments, but
Be it will be understood to those of skill in the art that following described embodiment is part of the embodiment of the present invention, it is rather than whole
Embodiment, the present invention is merely to illustrate, and is not construed as limiting the scope of the present invention.Based on the embodiment in the present invention, ability
The every other embodiment that domain those of ordinary skill is obtained under the premise of creative work is not made, belongs to guarantor of the present invention
The scope of shield.Unreceipted actual conditions person in embodiment, the condition suggested according to normal condition or manufacturer are carried out.Agents useful for same
Or the unreceipted production firm person of instrument, it is the conventional products that can be obtained by commercially available purchase.
The all examples below of the present invention is based on following core process：
Make hexachloroacetone and hydrogen fluoride that first step substitution reaction, the production of generation first occur in the presence of the first catalyst
Thing, the temperature of the first step substitution reaction is 70~80 DEG C, and first catalyst is trivalent chromium compound.
Make first product and hydrogen fluoride that second step substitution reaction occur in the presence of the second catalyst, generate hexafluoro
Acetone, the temperature of the second step substitution reaction is 350~400 DEG C, and second catalyst includes trivalent chromium compound.
Hydrogen is passed through into Hexafluoro acetone, reduction reaction occurs, generates hexafluoroisopropanol.
Each embodiment has carried out following improvement respectively in above key foundation：
Preferably, in the first step substitution reaction, the weight of first catalyst and the body of the hexachloroacetone
Product ratio is 3~4g：500mL.
Preferably, in the first step substitution reaction, the volume ratio of the hydrogen fluoride and the hexachloroacetone for 1~
1.5:2。
Preferably, rectifying, extraction therein three are also carried out to first product before the second step substitution reaction
Fluorine trichloroacetone and tetrafluoro dichloroacetone.
Preferably, in the second step substitution reaction, the weight of second catalyst and the first described product
Volume ratio is 2~4g：100mL；
Preferably, second catalyst also contains palladium bichloride.
Preferably, in the second step substitution reaction, the volume ratio of the hydrogen fluoride and first product is 1~1.5:
1。
Preferably, the condition of the reduction reaction is：
Pressure is 0.4~0.6MPa, temperature is 60~80 DEG C.
Preferably, the condition of the reduction reaction is：Back flow reaction more than 8 hours.
Embodiment 1
Hexafluoroisopropanol is synthesized, flow is as shown in Figure 1：
1st, 500mL 99% hexachloroacetone is added in reactor, is passed through anhydrous hydrogen fluoride 250mL, add catalyst three
Two chromium 3g are aoxidized ,~70 DEG C is heated to and flows back 2 hours, sample chromatography, trifluoro trichloroacetone and tetrafluoro dichloroacetone content
Reach 47%.
2nd, first step product is slightly evaporated by rectifying column, 70-80 DEG C of temperature, is collected into trifluoro trichloroacetone (a small amount of) and four
Fluorine dichloroacetone (volume) 94.3mL.
3rd, trifluoro trichloroacetone and tetrafluoro dichloroacetone mixture (the 2nd step product) are added into another reactor, added
Catalyst chrome green 2g, palladium bichloride 2g, it is passed through anhydrous hydrogen fluoride 90mL heatings and is heated to~350 DEG C 50 minutes, be passed through water
In, Hexafluoro acetone trihydrate is obtained, by rectifying column rectifying, middle control sampling, Hexafluoro acetone reaches 90% qualified, accessory substance
It is reflowable to continue to react.
4th, by previous step product-Hexafluoro acetone trihydrate put into new reactor be passed through 20mL hydrogen pressure for~
0.4MPa, it is warming up to 60-80 DEG C and flows back 8 hours, detected by being sampled after rectifying column, hexafluoroisopropanol content is 99.5%, production
Product are qualified.
5th, product is dried.
The total recovery for calculating hexafluoroisopropanol is 90%.
Embodiment 2
Hexafluoroisopropanol is synthesized, the difference from embodiment 1 is different in catalytic amount used in the 1st step：
1st, 500mL 99% hexachloroacetone is added in reactor, is passed through anhydrous hydrogen fluoride 250mL, add catalyst three
Two chromium 4g are aoxidized ,~70 DEG C is heated to and flows back 2 hours, sample chromatography, trifluoro trichloroacetone and tetrafluoro dichloroacetone content
Reach 51%.
2nd, first step product is slightly evaporated by rectifying column, 70-80 DEG C of temperature, is collected into trifluoro trichloroacetone and tetrafluoro dichloro
Acetone 103mL.
3rd, trifluoro trichloroacetone and tetrafluoro dichloroacetone mixture (the 2nd step product) are added into another reactor, added
Catalyst chrome green 2g, palladium bichloride 2g, it is passed through anhydrous hydrogen fluoride 90mL heatings and is heated to~350 DEG C 50 minutes, be passed through water
In, Hexafluoro acetone trihydrate is obtained, by rectifying column rectifying, middle control sampling, it is qualified that Hexafluoro acetone reaches 90%.
4th, by previous step product-Hexafluoro acetone trihydrate put into new reactor be passed through 20mL hydrogen pressure for~
0.4MPa, it is warming up to 60-80 DEG C and flows back 8 hours, detected by being sampled after rectifying column, hexafluoroisopropanol content is 99.5%, production
Product are qualified.
5th, product is dried.
The total recovery for calculating hexafluoroisopropanol is 93%.
Embodiment 3
Hexafluoroisopropanol is synthesized, the difference from embodiment 1 is different in the catalyst in the 3rd step：
1st, 500mL 99% hexachloroacetone is added in reactor, is passed through anhydrous hydrogen fluoride 250mL, add catalyst three
Two chromium 3g are aoxidized, 70 DEG C is heated to and flows back 2 hours, sample chromatography, trifluoro trichloroacetone and tetrafluoro dichloroacetone content reach
To 46%.
2nd, first step product is slightly evaporated by rectifying column, 70-80 DEG C of temperature, is collected into trifluoro trichloroacetone and tetrafluoro dichloro
Acetone 93mL.
3rd, trifluoro trichloroacetone and tetrafluoro dichloroacetone mixture (the 2nd step product) are added into another reactor, added
Catalyst chrome green 2g, it is passed through anhydrous hydrogen fluoride 90mL heatings and is heated to 350 DEG C 50 minutes, be passed through in water, obtain hexafluoro
Acetone trihydrate, by rectifying column rectifying, middle control sampling, it is qualified that Hexafluoro acetone reaches 90%.
4th, previous step product-new reactor of Hexafluoro acetone trihydrate input is passed through 20mL hydrogen pressure and is
0.4MPa, it is warming up to 60-80 DEG C and flows back 8 hours, detected by being sampled after rectifying column, hexafluoroisopropanol content is 99.4%, production
Product are qualified.
5th, product is dried.
The total recovery for calculating hexafluoroisopropanol is 91%.
Embodiment 4
It is different from the temperature that the difference of embodiment 1 is the reaction of the 1st step：
1st, 500mL 99% hexachloroacetone is added in reactor, is passed through anhydrous hydrogen fluoride 250mL, add catalyst three
Two chromium 3g are aoxidized ,~80 DEG C is heated to and flows back 2 hours, sample chromatography, trifluoro trichloroacetone and tetrafluoro dichloroacetone content
Reach 47%.
2nd, first step product is slightly evaporated by rectifying column, 70-80 DEG C of temperature, is collected into trifluoro trichloroacetone and tetrafluoro dichloro
Acetone 95mL.
3rd, trifluoro trichloroacetone and tetrafluoro dichloroacetone mixture (the 2nd step product) are added into another reactor, added
Catalyst chrome green 2g, palladium bichloride 2g, it is passed through anhydrous hydrogen fluoride 90mL heatings and is heated to~400 DEG C 50 minutes, be passed through water
In, Hexafluoro acetone trihydrate is obtained, by rectifying column rectifying, middle control sampling, it is qualified that Hexafluoro acetone reaches 90%.
4th, by previous step product-Hexafluoro acetone trihydrate put into new reactor be passed through 20mL hydrogen pressure for~
0.6MPa, it is warming up to 60-80 DEG C and flows back 8 hours, detected by being sampled after rectifying column, hexafluoroisopropanol content is 99.4%, production
Product are qualified.
5th, product is dried.
The total recovery for calculating hexafluoroisopropanol is 94%.
Embodiment 5
It is different from the temperature that the difference of embodiment 1 is the reaction of the 3rd step：
1st, 500mL 99% hexachloroacetone is added in reactor, is passed through anhydrous hydrogen fluoride 250mL, add catalyst three
Two chromium 3g are aoxidized ,~70 DEG C is heated to and flows back 2 hours, sample chromatography, trifluoro trichloroacetone and tetrafluoro dichloroacetone content
Reach 47%.
2nd, first step product is slightly evaporated by rectifying column, 70-80 DEG C of temperature, is collected into trifluoro trichloroacetone and tetrafluoro dichloro
Acetone 93.3mL.
3rd, trifluoro trichloroacetone and tetrafluoro dichloroacetone mixture (the 2nd step product) are added into another reactor, added
Catalyst chrome green 2g, palladium bichloride 2g, it is passed through anhydrous hydrogen fluoride 90mL heatings and is heated to~400 DEG C 50 minutes, be passed through water
In, Hexafluoro acetone trihydrate is obtained, by rectifying column rectifying, middle control sampling, it is qualified that Hexafluoro acetone reaches 90%.
4th, by previous step product-Hexafluoro acetone trihydrate put into new reactor be passed through 20mL hydrogen pressure for~
0.6MPa, it is warming up to 60-80 DEG C and flows back 8 hours, detected by being sampled after rectifying column, hexafluoroisopropanol content is 99.3%, production
Product are qualified.
5th, product is dried.
The total recovery for calculating hexafluoroisopropanol is 90%.
Embodiment 6
It is that the dosage of hydrogen fluoride is different from the difference of embodiment 1：
1st, 500mL 99% hexachloroacetone is added in reactor, is passed through anhydrous hydrogen fluoride 250mL, add catalyst three
Two chromium 3g are aoxidized, 80 DEG C is heated to and flows back 2 hours, sample chromatography, trifluoro trichloroacetone and tetrafluoro dichloroacetone content reach
To 48%.
2nd, first step product is slightly evaporated by rectifying column, 70-80 DEG C of temperature, is collected into trifluoro trichloroacetone and tetrafluoro dichloro
Acetone 5.1mL.
3rd, trifluoro trichloroacetone and tetrafluoro dichloroacetone mixture (the 2nd step product) are added into another reactor, added
Catalyst chrome green 2g, palladium bichloride 2g, it is passed through anhydrous hydrogen fluoride 90mL heatings and is heated to 400 DEG C 50 minutes, be passed through in water,
Hexafluoro acetone trihydrate is obtained, by rectifying column rectifying, middle control sampling, it is qualified that Hexafluoro acetone reaches 90%.
4th, previous step product-new reactor of Hexafluoro acetone trihydrate input is passed through 20mL hydrogen pressure and is
0.6MPa, it is warming up to 60-80 DEG C and flows back 8 hours, detected by being sampled after rectifying column, hexafluoroisopropanol content is 99.4%, production
Product are qualified.
5th, product is dried.
The total recovery for calculating hexafluoroisopropanol is 92%.
Finally it should be noted that：Various embodiments above is merely illustrative of the technical solution of the present invention, rather than its limitations；To the greatest extent
The present invention is described in detail with reference to foregoing embodiments for pipe, it will be understood by those within the art that：Its according to
The technical scheme described in foregoing embodiments can so be modified, either which part or all technical characteristic are entered
Row equivalent substitution；And these modifications or replacement, the essence of appropriate technical solution is departed from various embodiments of the present invention technology
The scope of scheme.
Claims (10)
- A kind of 1. method for synthesizing Hexafluoro acetone, it is characterised in that comprise the following steps：Make hexachloroacetone and hydrogen fluoride that first step substitution reaction occur in the presence of the first catalyst, generate the first product, institute The temperature for stating first step substitution reaction is 70~80 DEG C, and first catalyst is trivalent chromium compound；Make first product and hydrogen fluoride that second step substitution reaction occur in the presence of the second catalyst, generate hexafluoro third Ketone, the temperature of the second step substitution reaction is 350~400 DEG C, and second catalyst includes trivalent chromium compound.
- 2. according to the method for claim 1, it is characterised in that in the first step substitution reaction, first catalysis The weight of agent and the volume ratio of the hexachloroacetone are 3~4g：500mL.
- 3. method according to claim 1 or 2, it is characterised in that in the first step substitution reaction, the hydrogen fluoride Volume ratio with the hexachloroacetone is 1~1.5:2.
- 4. according to the method for claim 1, it is characterised in that also to described first before the second step substitution reaction Product carries out rectifying, extracts trifluoro trichloroacetone and tetrafluoro dichloroacetone therein.
- 5. according to the method for claim 1, it is characterised in that in the second step substitution reaction, second catalysis The weight of agent and the volume ratio of the first described product are 2~4g：100mL.
- 6. according to the method for claim 1, it is characterised in that second catalyst also contains palladium bichloride.
- 7. method according to claim 1 or 5, it is characterised in that in the second step substitution reaction, the hydrogen fluoride with The volume ratio of first product is 1~1.5:1.
- A kind of 8. method for synthesizing hexafluoroisopropanol, it is characterised in that comprise the following steps：Hexafluoro acetone is synthesized using the method described in claim any one of 1-7, makes it that reduction reaction, generation six occur with hydrogen Fluorine isopropanol.
- 9. according to the method for claim 8, it is characterised in that the condition of the reduction reaction is：Pressure is 0.4~0.6MPa, temperature is 60~80 DEG C.
- 10. method according to claim 8 or claim 9, it is characterised in that the condition of the reduction reaction is：Back flow reaction 8 is small When more than.
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| CN201711103212.2A CN107759451A (en) | 2017-11-10 | 2017-11-10 | A kind of method for synthesizing Hexafluoro acetone and the method for synthesizing hexafluoroisopropanol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113717030A (en) * | 2021-09-01 | 2021-11-30 | 江苏福赛乙德药业有限公司 | Preparation method of hexafluoroisopropanol |
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| CN113717030A (en) * | 2021-09-01 | 2021-11-30 | 江苏福赛乙德药业有限公司 | Preparation method of hexafluoroisopropanol |
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