CN112409125A - Method for continuously preparing diaryl hexafluoropropane - Google Patents
Method for continuously preparing diaryl hexafluoropropane Download PDFInfo
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- CN112409125A CN112409125A CN202011374997.9A CN202011374997A CN112409125A CN 112409125 A CN112409125 A CN 112409125A CN 202011374997 A CN202011374997 A CN 202011374997A CN 112409125 A CN112409125 A CN 112409125A
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- 238000000034 method Methods 0.000 title claims abstract description 24
- -1 diaryl hexafluoropropane Chemical compound 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 72
- 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
- 239000012043 crude product Substances 0.000 claims abstract description 18
- 239000000047 product Substances 0.000 claims abstract description 16
- 239000002608 ionic liquid Substances 0.000 claims abstract description 15
- 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
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 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
- 235000010265 sodium sulphite Nutrition 0.000 claims description 9
- 238000010924 continuous production Methods 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 208000012839 conversion disease Diseases 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 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
- 230000008569 process Effects 0.000 description 5
- 229940078552 o-xylene Drugs 0.000 description 4
- 231100000086 high toxicity Toxicity 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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
- 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
- 239000012295 chemical reaction liquid Substances 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 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
- 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 1
- 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
- 230000015572 biosynthetic process 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
- 231100000171 higher 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 238000004064 recycling 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
- 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
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- 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, and belongs to the technical field of organic synthesis. The method for continuously preparing diaryl hexafluoropropane comprises the following steps: (1) mixing hexafluoroacetone trihydrate, an aryl compound and a catalyst ionic liquid (which can also be used as a solvent), and adding an antioxidant; (2) introducing the crude product into a circulating loop reactor under a certain reaction temperature condition, and maintaining for a certain time to prepare a target product crude product; (3) and (3) cooling the crude product statically, filtering out solids, 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 the corrosion to equipment, improves the efficiency on the premise of keeping higher conversion rate and selectivity, enhances the safety of the reaction, and is energy-saving and environment-friendly.
Description
Technical Field
The invention relates to a method for continuously preparing diaryl hexafluoropropane, and belongs to the technical field of organic synthesis.
Background
Diarylhexafluoropropanes refer to 2, 2-diarylhexafluoropropane compounds, a class of molecules of significant value. Such as bisphenol AF, is a vulcanizing agent required by mixing fluororubber and an important intermediate material, and can be used as an intermediate for modifying polymers; 2, 2-bis (3, 4-dimethylphenyl) hexafluoropropane (6 FXY for short) is an important precursor for synthesizing a polyimide monomer 6 FDA.
The synthesis process of diaryl hexafluoropropane is basically open, and the following methods are mainly used at present:
patents US4,400,546 and CN101870641 both report that hexafluoroacetone and phenol are used to 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-.
Patent CN200810243703.1 reports that hexafluoroacetone trihydrate is used as a raw material, hexafluoroacetone trihydrate and aniline are used as raw materials, and four-step reactions of condensation diazotization, hydrolysis and alkylation are performed to synthesize bisphenol AF under normal pressure.
In patent CN104496763, under the action of hydrogen fluoride, hexafluoropropylene oxide and phenol are used to prepare bisphenol AF by a one-pot method, the use of HFA with high toxicity is avoided, the process is simple, but hydrogen fluoride has high corrosivity and high requirement on equipment; CN 101851147A adopts a similar method to prepare a diaryl hexafluoropropane compound.
Patent US57633699 reports the preparation of bisphenol AF by reacting phenol with anhydrous hexafluoroacetone using trifluoromethanesulfonic acid as catalyst, avoiding the use of HF, but still using HFA with high toxicity as raw material.
Patent CN 111233632 reports that hexafluoropropylene oxide and phenylalkyl ether are used as raw materials, and 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 strong corrosivity.
The method for preparing bisphenol AF by fluorination by taking bisphenol A as a raw material has high yield and low price, and is a very promising method, but the method uses high-toxicity F2 and has high danger, and specific reaction parameters are not reported.
Although the methods have various characteristics, and a plurality of methods and processes are very stable and mature, the problems of strong corrosivity, serious environmental pollution, greater risk in the production process and the like generally exist, so that the improvement of the existing process to realize safe and efficient production is still very meaningful.
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 the corrosion to equipment, improves the efficiency on the premise of keeping higher conversion rate and selectivity, enhances the safety of reaction, saves energy and protects environment.
The chemical general formula of the diaryl hexafluoropropane is as follows:
R1＝H,Me,Et，OH；
R2＝H,Me,Et,OH。
the method for continuously preparing diaryl hexafluoropropane comprises the following steps:
(1) mixing hexafluoroacetone trihydrate, an aryl compound and a catalyst ionic liquid (which can also be used as a solvent), and adding an antioxidant;
(2) introducing the crude product into a circulating loop reactor at a certain speed under a certain reaction temperature condition, and maintaining for a certain time to prepare a target product crude product;
(3) and (3) cooling the crude product statically, filtering out solids, 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 the hexafluoroacetone trihydrate is 1-3: 1.
preferably, the catalyst ionic liquid is imidazole [ C ]nmim][x](X＝HSO4，H2PO4Etc.) or quaternary ammonium salts [ R3NH][x](X＝HSO4，H2PO4) 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 based on the amount of the aromatic compound.
Preferably, in the step (2), the reaction temperature is 80-150 ℃, preferably 90-120 ℃; preferably, the reaction is carried out for 5-10 min.
The feeding speed is determined by the reaction retention time and the size of the equipment, and the feeding speed can be obtained according to the size of the reaction equipment under the condition of the precursor determined by the reaction retention time.
The ionic liquid recovered by the method 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 the 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 circulation loop reactor is used as a reaction device, so that the mass transfer and heat transfer of the reaction are enhanced, the continuous production of the product is realized, and the preparation efficiency is improved.
The loop reactor according to the invention is a device known to the person skilled in the art.
Compared with the prior art, the invention has the following beneficial effects:
(1) the efficiency is improved by adopting a continuous production mode on the premise of keeping higher conversion rate and selectivity;
(2) the ionic liquid catalyst is used, is nontoxic, can be repeatedly used for many times, and is environment-friendly;
(3) the use of substances with higher toxicity and strong corrosivity is avoided, and the safety of the reaction is improved;
(4) and a strong acid substance is not used, so that the generation of waste acid is avoided, and the environmental protection pressure is reduced.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the practice of the invention.
Example 1
500g of hexafluoroacetone trihydrate, 500g of [ C ]6mim][HSO4]481g of o-xylene and 5g of sodium sulfite are stirred and mixed at room temperature, and then pumped into a circulating loop reactor for reaction, the reaction temperature is 120 ℃, the reaction retention time is 8min, after the reaction is finished, the reaction is kept stand, a solid product is separated out from a reaction solution, a crude product is obtained by filtration and separation, the reaction conversion rate is 98 percent calculated by hexafluoroacetone trihydrate, the selectivity is 93 percent, and a pure product is obtained by recrystallization.
Example 2
500g of hexafluoroacetone trihydrate, 500g of [ C ]6mim][HSO4]433g of o-xylene and 5g of sodium sulfite are stirred and mixed at room temperature, and then pumped into a circulation loop reactor for reaction, the reaction temperature is 130 ℃, the reaction retention time is 10min, after the reaction is finished, the reaction is kept still, a solid product is separated out from a reaction solution, a crude product is obtained by filtration and separation, the reaction conversion rate is 99% by weight of hexafluoroacetone trihydrate, the selectivity is 89%, and a pure product is obtained by recrystallization.
Example 3
500g of hexafluoroacetone trihydrate, 500g of [ Et ]3N][HSO4]530g of o-xylene and 5g of sodium sulfite are stirred and mixed at room temperature, and then pumped into a circulation loop reactor for reaction, the reaction temperature is 90 ℃, the reaction retention time is 8min, after the reaction is finished, the reaction is kept stand, a solid product is separated out from a reaction solution, a crude product is obtained by filtration and separation, the reaction conversion rate is 90% by weight of hexafluoroacetone trihydrate, the selectivity is 94%, and a pure product is obtained by recrystallization.
Example 4
Will 500g hexafluoroacetone trihydrate, 500g [ C ]6mim][HSO4]448g of phenol and 10g of sodium sulfite are stirred and mixed at room temperature, and then are pumped into a circulating loop reactor for reaction, the reaction temperature is 100 ℃, the reaction retention time is 5min, after the reaction is finished, the reaction is kept stand, a solid product is separated out from a reaction solution, a crude product is obtained by filtration and separation, the reaction conversion rate is 98 percent by taking hexafluoroacetone trihydrate, the selectivity is 95 percent, and a pure product is obtained by recrystallization.
Example 5
500g of hexafluoroacetone trihydrate, 500g of [ Et ]3N][HSO4]493g of phenol and 10g 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 100 ℃, the reaction retention time is 6min, after the reaction is finished, the mixture is stood, a solid product is separated out from a reaction liquid, a crude product is obtained by filtration and separation, the reaction conversion rate is 99 percent calculated by hexafluoroacetone trihydrate, the selectivity is 96 percent, and a pure product is obtained by recrystallization.
Example 6
500g of hexafluoroacetone trihydrate, 500g of [ C ]6mim]HSO4403g of phenol and 6g of sodium sulfite are stirred and mixed at room temperature, and then pumped into a circulation loop reactor for reaction, the reaction temperature is 90 ℃, the reaction retention time is 8min, after the reaction is finished, the reaction is kept stand, a solid product is separated out from a reaction solution, a crude product is obtained by filtration and separation, the reaction conversion rate is 97 percent based on hexafluoroacetone trihydrate, the selectivity is 82 percent, and a pure product is obtained by recrystallization.
Example 7
500g of hexafluoroacetone trihydrate, 500g of [ C ]6mim][HSO4](fifth circulation), 448g of phenol and 10g of sodium sulfite are stirred and mixed at room temperature, and then are pumped into a circulation loop reactor for reaction, the reaction temperature is 100 ℃, the reaction retention time is 5min, after the reaction is finished, the reaction is kept still, a solid product is separated out from the reaction liquid, a crude product is obtained by filtration and separation, the reaction conversion rate is 95% by weight of hexafluoroacetone trihydrate, the selectivity is 93%, and a pure product is obtained by recrystallization.
Comparative example 1
377g of hexafluoroacetone (gas), 448g of phenol and 363g of 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% in terms of hexafluoroacetone, the selectivity is 89%, and the pure product is obtained after the crude product is subjected to alkali washing and recrystallization.
Comparative example 2
377g of hexafluoroacetone (gas), 363g of hydrogen fluoride and 505g of 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 in terms of hexafluoroacetone, the selectivity is 87 percent, and the crude product is recrystallized to obtain a pure product.
The above-mentioned embodiments are intended to illustrate the technical solutions and advantages of the present invention, and it should be understood that the above-mentioned embodiments are only specific embodiments of the present invention, and are not intended to limit the present invention, and any modifications, additions, equivalents, etc. made within the scope of the principles of the present invention should be included in the scope of the present invention.
Claims (7)
1. A method for continuously preparing diaryl hexafluoropropane is characterized in that: the method comprises the following steps:
(1) mixing hexafluoroacetone trihydrate, an aryl compound and a catalyst ionic liquid, and adding an antioxidant;
(2) introducing the crude product into a circulating loop reactor under a certain reaction temperature condition, and maintaining for a certain time to prepare a target product crude product;
(3) and (3) cooling the crude product statically, filtering out solids, refining to obtain a pure product, and applying the ionic liquid to the next reaction.
2. The continuous process for preparing diarylhexafluoropropanes according to claim 1, wherein: the molar ratio of the hexafluoroacetone trihydrate to the aryl compound is 1: 1.5-3.
3. The continuous process for preparing diarylhexafluoropropanes according to claim 1, wherein: the mass ratio of the catalyst ionic liquid to the hexafluoroacetone trihydrate is 1-3: 1.
4. the continuous process for the preparation of diarylhexafluoropropanes according to claim 1 or 3, wherein: the catalyst ionic liquid is imidazole [ C ]nmim][x](X＝HSO4，H2PO4Etc.) or quaternary ammonium salts [ R3NH][x](X＝HSO4，H2PO4) An ionic liquid.
5. The continuous process for preparing diarylhexafluoropropanes according to claim 1, wherein: the antioxidant is sodium sulfite or sodium phosphite.
6. The continuous process for preparing diarylhexafluoropropanes according to claim 1, wherein: the antioxidant is used in an amount of 0.5-5% by mass based on the mass of the aromatic compound.
7. The continuous process for preparing diarylhexafluoropropanes according to claim 1, wherein: in the step (2), the reaction temperature is 80-150 ℃, and the reaction lasts for 5-10 min.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113004144A (en) * | 2021-03-09 | 2021-06-22 | 西安瑞联新材料股份有限公司 | Synthesis method of perfluorobisphenol A |
| CN115636759A (en) * | 2022-10-27 | 2023-01-24 | 天津众泰材料科技有限公司 | Preparation method of 2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane |
| CN117164437A (en) * | 2023-08-08 | 2023-12-05 | 江苏福赛乙德药业有限公司 | Preparation process of high-purity bisphenol AF |
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| 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 |
| US20190058178A1 (en) * | 2017-08-17 | 2019-02-21 | Ohio Aerospace Institute | Polyimide-network and polyimide-urea-network battery separator compositions |
-
2020
- 2020-11-30 CN CN202011374997.9A patent/CN112409125B/en active Active
Patent Citations (4)
| 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 |
| US20190058178A1 (en) * | 2017-08-17 | 2019-02-21 | Ohio Aerospace Institute | Polyimide-network and polyimide-urea-network battery separator compositions |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113004144A (en) * | 2021-03-09 | 2021-06-22 | 西安瑞联新材料股份有限公司 | Synthesis method of perfluorobisphenol A |
| CN115636759A (en) * | 2022-10-27 | 2023-01-24 | 天津众泰材料科技有限公司 | Preparation method of 2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane |
| CN117164437A (en) * | 2023-08-08 | 2023-12-05 | 江苏福赛乙德药业有限公司 | Preparation process of high-purity bisphenol AF |
| CN117164437B (en) * | 2023-08-08 | 2024-04-19 | 江苏福赛乙德药业有限公司 | Bisphenol AF preparation process |
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