CN112409125B - Method for continuously preparing diaryl hexafluoropropane - Google Patents
Method for continuously preparing diaryl hexafluoropropane Download PDFInfo
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- CN112409125B CN112409125B CN202011374997.9A CN202011374997A CN112409125B CN 112409125 B CN112409125 B CN 112409125B CN 202011374997 A CN202011374997 A CN 202011374997A CN 112409125 B CN112409125 B CN 112409125B
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- hexafluoroacetone trihydrate
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- 238000000034 method Methods 0.000 title claims abstract description 25
- -1 diaryl hexafluoropropane Chemical compound 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 61
- SNZAEUWCEHDROX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;trihydrate Chemical compound O.O.O.FC(F)(F)C(=O)C(F)(F)F SNZAEUWCEHDROX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000047 product Substances 0.000 claims abstract description 16
- 239000012043 crude product Substances 0.000 claims abstract description 15
- 239000002608 ionic liquid Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 7
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 238000007670 refining Methods 0.000 claims abstract description 3
- 239000007787 solid Substances 0.000 claims abstract description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical group [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 235000010265 sodium sulphite Nutrition 0.000 claims description 9
- 229940078552 o-xylene Drugs 0.000 claims description 5
- 238000010924 continuous production Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 208000012839 conversion disease Diseases 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000012295 chemical reaction liquid Substances 0.000 description 7
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000012265 solid product Substances 0.000 description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 6
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- GLFKFHJEFMLTOB-UHFFFAOYSA-N 4-[2-(3,4-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-1,2-dimethylbenzene Chemical compound C1=C(C)C(C)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C)C(C)=C1 GLFKFHJEFMLTOB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2637—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for continuously preparing diaryl hexafluoropropane, belonging to the technical field of organic synthesis. The continuous preparation method of diaryl hexafluoropropane comprises the following steps: (1) Mixing hexafluoroacetone trihydrate, aryl compound and catalyst ionic liquid (which can also be used as solvent), and adding antioxidant; (2) Introducing the mixture into a circulation loop reactor under a certain reaction temperature condition, and maintaining for a certain time to obtain a crude product of a target product; (3) Filtering the solid after the crude product is cooled still, refining to obtain a pure product, and applying the ionic liquid to the next reaction. The method is scientific and reasonable, is simple and convenient to operate, reduces corrosion to equipment, improves efficiency on the premise of keeping higher conversion rate and selectivity, and simultaneously enhances the safety of reaction, and is energy-saving and environment-friendly.
Description
Technical Field
The invention relates to a method for continuously preparing diaryl hexafluoropropane, belonging to the technical field of organic synthesis.
Background
Diaryl hexafluoropropane refers to 2, 2-diaryl hexafluoropropane compounds, which are a class of molecules of great value. Such as bisphenol AF, is not only a vulcanizing agent required for mixing fluororubber, but also an important intermediate material, and can be used as an intermediate for modifying polymers; 2, 2-bis (3, 4-dimethylphenyl) hexafluoropropane (abbreviated as 6 FXY) is an important precursor for synthesizing polyimide monomer 6 FDA.
The synthesis process of diaryl hexafluoropropane is basically communicated, and the following methods are mainly adopted at present:
patent US4,400,546 and CN101870641 both report that hexafluoroacetone and phenol prepare bisphenol AF under the catalysis of hydrogen fluoride, the process is simple, the conditions are mature, but toxic gas hexafluoroacetone is used, and the use of hydrogen fluoride puts higher requirements on equipment; [ Journal of Fluorine Chemistry (123) (2003) 221-225] reported the preparation of 2, 2-bis (3, 4-dimethylphenyl) hexafluoropropane using a similar method.
Patent CN200810243703.1 reports that hexafluoroacetone trihydrate is used as a raw material, hexafluoroacetone trihydrate and aniline are used as raw materials, bisphenol AF is synthesized under normal pressure through four steps of condensation diazotization, hydrolysis and alkylation, the synthesis process is environment-friendly, the reaction condition is mild, the selectivity is good, the yield is higher, but the reaction steps are long, and the overall efficiency is low.
The patent CN104496763 prepares bisphenol AF by using hexafluoropropylene oxide and phenol under the action of hydrogen fluoride by adopting a one-pot method, the process avoids the use of HFA with larger toxicity, and has simple process, but the hydrogen fluoride has larger corrosiveness and high requirement on equipment; CN101851147 a employed a similar method to prepare the diarylhexafluoropropane compound.
Patent US57633699 reports that bisphenol AF is prepared by reacting phenol with anhydrous hexafluoroacetone with trifluoromethanesulfonic acid as catalyst, avoiding the use of HF, but still using HFA with greater toxicity as raw material.
Patent CN 111233632 reports that by taking hexafluoropropylene oxide and phenylalkyl ether as raw materials, three processes of isomerization, friedel-crafts alkylation and removal of alkyl in ether bond are completed through one-step reaction, and continuous high-yield preparation is realized, but fluorine-containing hydrogen chloride adopted in the reaction still has stronger corrosiveness.
Bisphenol A is used as a raw material for preparing bisphenol AF by fluorination, the yield is high, the price is low, and the method becomes a very promising method, but the method uses high-toxicity F2, has high risk, and meanwhile, specific reaction parameters have not been reported.
Although the methods have the characteristics, and many methods have very stable and mature processes, the problems of strong corrosiveness, serious environmental pollution, large risk in the production process and the like generally exist, so that the improvement of the existing processes and the realization of safe and efficient production are very significant.
Disclosure of Invention
The invention aims to provide a method for continuously preparing diaryl hexafluoropropane, which is scientific and reasonable, is simple and convenient to operate, reduces corrosion to equipment, improves efficiency on the premise of keeping higher conversion rate and selectivity, enhances the safety of reaction, and is energy-saving and environment-friendly.
The chemical general formula of the diaryl hexafluoropropane is as follows:
R1＝H,Me,Et，OH；
R2＝H,Me,Et,OH。
the continuous preparation method of diaryl hexafluoropropane comprises the following steps:
(1) Mixing hexafluoroacetone trihydrate, aryl compound and catalyst ionic liquid (which can also be used as solvent), and adding antioxidant;
(2) Introducing the mixture into a circulation loop reactor at a certain speed under a certain reaction temperature condition, and maintaining for a certain time to obtain a crude product of a target product;
(3) Filtering the solid after the crude product is cooled still, refining to obtain a pure product, and applying the ionic liquid to the next reaction.
Preferably, the molar ratio of hexafluoroacetone trihydrate to aryl compound is 1:1.5-3.
Preferably, the mass ratio of the catalyst ionic liquid to hexafluoroacetone trihydrate is 1-3:1.
preferably, the catalyst ionic liquid is an imidazole [ C n mim][x](X＝HSO 4 ，H 2 PO 4 Etc.) or quaternary ammonium salts [ R 3 NH][x](X＝HSO 4 ，H 2 PO 4 ) And (3) an ionic liquid.
Preferably, the antioxidant is sodium sulfite or sodium phosphite.
Preferably, the antioxidant is used in an amount of 0.5 to 5% by mass of the aryl compound.
Preferably, in step (2), the reaction temperature is 80-150 ℃, preferably 90-120 ℃; preferably, the reaction is carried out for 5 to 10 minutes.
The speed of the feeding is determined by the reaction retention time and the size of the equipment, and the feeding speed can be known according to the size of the reaction equipment under the precursor determined by the reaction retention time.
The ionic liquid recovered by the invention is recycled after vacuum drying, and the catalytic activity is not obviously reduced after 5 times of recycling.
The invention adopts the reusable ionic liquid catalyst and hexafluoroacetone trihydrate with higher safety as raw materials, thereby reducing the corrosion to equipment, improving the safety of the reaction and reducing the generation of three wastes; the circulating loop reactor is used as a reaction device, so that the mass and heat transfer of the reaction are enhanced, the continuous production of products is realized, and the preparation efficiency is improved.
The circulation loop reactor described in the present invention is a well known apparatus for those skilled in the art.
Compared with the prior art, the invention has the following beneficial effects:
(1) The continuous production mode is adopted, and the efficiency is improved on the premise of keeping higher conversion rate and selectivity;
(2) The ionic liquid catalyst is nontoxic, can be repeatedly used for a plurality of times, and is environment-friendly;
(3) Avoiding the use of substances with larger toxicity and strong corrosiveness, and improving the safety of the reaction;
(4) No strong acid substance is used, thereby avoiding the generation of waste acid and reducing the environmental protection pressure.
Detailed Description
The invention is further illustrated below in connection with examples, which are not intended to limit the practice of the invention.
Example 1
500g hexafluoroacetone trihydrate, 500g [ C ] 6 mim][HSO 4 ]481g of o-xylene and 5g of sodium sulfite are stirred and mixed at room temperature, then the mixture is pumped into a circulating loop reactor for reaction, the reaction temperature is 120 ℃, the reaction residence time is 8min, after the reaction is finished, the mixture is stood, solid products are separated out from reaction liquid, crude products are obtained through filtration and separation, the reaction conversion rate is 98 percent and the selectivity is 93 percent by hexafluoroacetone trihydrate, and the pure products are obtained after recrystallization.
Example 2
500g hexafluoroacetone trihydrate, 500g [ C ] 6 mim][HSO 4 ]433g of o-xylene, 5g of sodium sulfite are stirred and mixed at room temperature and pumped into a circulation loopThe reaction is carried out in a reactor, the reaction temperature is 130 ℃, the reaction residence time is 10min, after the reaction is finished, the solid product is separated out from the reaction liquid by standing, the crude product is obtained by filtration and separation, the reaction conversion rate is 99 percent and the selectivity is 89 percent by using hexafluoroacetone trihydrate, and the pure product is obtained after recrystallization.
Example 3
500g hexafluoroacetone trihydrate, 500g [ Et ] 3 N][HSO 4 ]530g of o-xylene and 5g of sodium sulfite are stirred and mixed at room temperature, then the mixture is pumped into a circulating loop reactor for reaction, the reaction temperature is 90 ℃, the reaction residence time is 8min, after the reaction is finished, the mixture is stood, solid products are separated out from reaction liquid, crude products are obtained through filtration and separation, the reaction conversion rate is 90 percent and the selectivity is 94 percent according to hexafluoroacetone trihydrate, and the pure products are obtained after recrystallization.
Example 4
500g hexafluoroacetone trihydrate, 500g [ C ] 6 mim][HSO 4 ]448g of phenol and 10g of sodium sulfite are stirred and mixed at room temperature, then the mixture is pumped into a circulation loop reactor for reaction, the reaction temperature is 100 ℃, the reaction residence time is 5min, after the reaction is finished, the mixture is stood, solid products are separated out from reaction liquid, crude products are obtained through filtration and separation, the reaction conversion rate is 98 percent and the selectivity is 95 percent by using hexafluoroacetone trihydrate, and the pure products are obtained after recrystallization.
Example 5
500g hexafluoroacetone trihydrate, 500g [ Et ] 3 N][HSO 4 ]493g of phenol and 10g of sodium sulfite are stirred and mixed at room temperature, then the mixture is pumped into a circulation loop reactor for reaction, the reaction temperature is 100 ℃, the reaction residence time is 6min, after the reaction is finished, the mixture is stood, solid products are separated out from reaction liquid, crude products are obtained through filtration and separation, the reaction conversion rate is 99 percent and the selectivity is 96 percent according to hexafluoroacetone trihydrate, and the pure products are obtained after recrystallization.
Example 6
500g hexafluoroacetone trihydrate, 500g [ C ] 6 mim]HSO 4 403g of phenol, 6g of sodium sulfite are stirred and mixed at room temperature and then pumped inThe reaction is carried out in a loop reactor, the reaction temperature is 90 ℃, the reaction residence time is 8min, after the reaction is finished, solid products are separated out from reaction liquid by standing, crude products are obtained by filtration and separation, the reaction conversion rate is 97 percent and the selectivity is 82 percent based on hexafluoroacetone trihydrate, and the pure products are obtained after recrystallization.
Example 7
500g hexafluoroacetone trihydrate, 500g [ C ] 6 mim][HSO 4 ](fifth cycle), 448g of phenol and 10g of sodium sulfite are stirred and mixed at room temperature, then pumped into a circulating loop reactor for reaction, the reaction temperature is 100 ℃, the reaction residence time is 5min, after the reaction is finished, the solid product is separated out of the reaction liquid by standing, the crude product is obtained by filtration and separation, the reaction conversion rate is 95 percent and the selectivity is 93 percent by hexafluoroacetone trihydrate, and the pure product is obtained after recrystallization.
Comparative example 1
377g hexafluoroacetone (gas), 448g phenol and 363g hydrogen fluoride are added into a reaction kettle, the reaction temperature is 100 ℃, the pressure is 1.0MPa, the reaction is carried out for 8 hours, after the reaction is finished, the reaction conversion rate is 89% by hexafluoroacetone, the selectivity is 89%, and the crude product is subjected to alkali washing and recrystallization to obtain a pure product.
Comparative example 2
377g hexafluoroacetone (gas), 363g hydrogen fluoride and 505g o-xylene are added into a reaction kettle, the reaction temperature is 150 ℃, the pressure is 2.5MPa, the reaction is carried out for 12 hours, after the reaction is finished, the reaction conversion rate is 90 percent by hexafluoroacetone, the selectivity is 87 percent, and the crude product is recrystallized to obtain a pure product.
The foregoing embodiments have described the technical solutions and advantages of the present invention in detail, and it should be understood that the foregoing embodiments are merely illustrative of the present invention and are not intended to limit the invention, and any modifications, additions, substitutions and the like that fall within the principles of the present invention should be included in the scope of the invention.
Claims (2)
1. A process for the continuous preparation of diaryl hexafluoropropane, characterized by: the method comprises the following steps:
(1) Mixing hexafluoroacetone trihydrate, aryl compound and catalyst ionic liquid, and simultaneously adding an antioxidant; the molar ratio of hexafluoroacetone trihydrate to aryl compound is 1:1.5-3, and the mass ratio of catalyst ionic liquid to hexafluoroacetone trihydrate is 1-3:1; the antioxidant is sodium sulfite;
(2) Introducing the mixture into a circulation loop reactor under a certain reaction temperature condition, and maintaining for a certain time to obtain a crude product of a target product; the reaction temperature is 80-150 ℃ and the reaction time is 5-10min;
(3) Filtering out solid after standing and cooling the crude product, refining to obtain a pure product, and applying the ionic liquid to the next reaction;
the catalyst ionic liquid is [ C 6 mim] [HSO 4 ]Or [ Et ] 3 NH][HSO 4 ]；
The aryl compound is o-xylene or phenol.
2. The continuous process for preparing diaryl hexafluoropropane according to claim 1, characterized in that: the antioxidant is used in an amount of 0.5-5% by weight of the aryl compound.
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| CN117164437B (en) * | 2023-08-08 | 2024-04-19 | 江苏福赛乙德药业有限公司 | Bisphenol AF preparation process |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0650949A1 (en) * | 1993-10-29 | 1995-05-03 | Nippon Mektron, Ltd. | Process for preparing 2,2-diphenylhexafluoropropanes |
| CN102584569A (en) * | 2011-12-15 | 2012-07-18 | 北京林业大学 | Method for preparing diphenolic acid in ionic liquid |
| CN103553883A (en) * | 2013-11-15 | 2014-02-05 | 白银海博生化科技有限公司 | Method for co-catalytic synthesis of bisphenol AF through molecular sieve and heteropoly acid |
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| US20190058178A1 (en) * | 2017-08-17 | 2019-02-21 | Ohio Aerospace Institute | Polyimide-network and polyimide-urea-network battery separator compositions |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0650949A1 (en) * | 1993-10-29 | 1995-05-03 | Nippon Mektron, Ltd. | Process for preparing 2,2-diphenylhexafluoropropanes |
| CN102584569A (en) * | 2011-12-15 | 2012-07-18 | 北京林业大学 | Method for preparing diphenolic acid in ionic liquid |
| CN103553883A (en) * | 2013-11-15 | 2014-02-05 | 白银海博生化科技有限公司 | Method for co-catalytic synthesis of bisphenol AF through molecular sieve and heteropoly acid |
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