CN110041354A - A kind of synthetic method of four penta phenyl fluoride borons acid potassium salt - Google Patents
A kind of synthetic method of four penta phenyl fluoride borons acid potassium salt Download PDFInfo
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- CN110041354A CN110041354A CN201910300291.9A CN201910300291A CN110041354A CN 110041354 A CN110041354 A CN 110041354A CN 201910300291 A CN201910300291 A CN 201910300291A CN 110041354 A CN110041354 A CN 110041354A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Abstract
The present invention discloses a kind of synthetic method of four penta phenyl fluoride boron acid potassium salts.Using iodomethane etc. as initiator, pentafluorophenyl group magnesium bromide is synthesized, four pentafluorophenyl boric acid magnesium salts are synthesized by grignard reaction, then react with potassium reagent and generate four penta phenyl fluoride boron acid potassium salts, the product total moles rate of recovery reaches 80% or more.Improve the organic boride auxiliary agent that four penta phenyl fluoride boron acid potassium salts are used to synthesize transition-metal catalyst as organic boride intermediate, the catalytic efficiency applied to olefin polymerization.
Description
Technical field
The present invention relates to a kind of synthetic methods of four penta phenyl fluoride boron acid potassium salts.
Technical background
Polyolefin is the high molecular material that yield is maximum in synthetic resin, purposes is most wide, be by ethylene, propylene, 1- butylene,
The alpha-olefins such as 1- amylene, 1- hexene, 1- octene and certain cycloolefins be polymerized alone or combined polymerization obtained from an analog thermoplastic
The general name of resin.Olefin polymer small, chemical resistance, water-tolerant with relative density；Good mechanical strength, electricity are absolutely
The features such as edge.It can be used for film, tubing, plate, various moulded products, wire and cable etc..In agricultural, packaging, electronics, electricity
Gas, automobile, machinery, daily use Sundry goods etc. have been widely used.Usual catalyst for olefines polymerizing be then manufacture of polyolefins and
The core of research and development.From traditional Ziegler-Natta catalyst, metallocene catalyst is arrived, then arrives transition-metal catalyst, it is novel
Polyolefin catalyst in particular for be copolymerized and functional polyolefin catalyst research and development, be always polymer chemistry,
The advanced subject of Organometallic Chemistry and material science.
Metallocene catalyst is the catalyst based on metallocene, be often referred to using metallocene compound as major catalyst and
The catalyst system that one Leiws acid is formed as co-catalyst, approval is that metallocene is urged with helping to catalytic polymerization mechanism substantially
Agent interacts the cationic catalytic active center to be formed.Therefore often referred to as " single site catalysts ".Because
The advantages that metallocene catalysis activity is high, the Polymer Molecular Weight narrowly distributing of generation, polymer molecular structure can design,
Countries in the world give the research of metallocene catalyst the attention of height.Compared to common Ziegler-Natta catalyst, cyclopentadienyl
Metallic catalyst is applied widely, active can also obtain the production of meet demand by changing self structure and reaction condition by force
Object.It is this if exxonmobil chemical company is using proprietary metallocene catalyst process production high viscosity Poly alpha Olefins (PAO) (PAO)
The more conventional poly- a alkene of new olefin polymerization has higher viscosity, lower pour point and preferable shear stability.Due to luxuriant gold
Metal catalyst high activity, single active center and to polymer molecular structure and performance the features such as, " can customize " product, cyclopentadienyl gold
Metal catalyst is increasing to the influence power of polymer production exploitation in industrialization and petrochemical industry, gradually becomes industry
The Main way of technical research.
The organoboron compound auxiliary agent of metallocene catalyst exists generally by aromatic halogenated compound (such as five bromofluorobenzenes)
(- 78 DEG C) are reacted with butyl lithium under cryogenic conditions, are generated lithium salts, then react with borating agents such as boron trifluorides, are obtained four or five fluorine
Phenyl boric acid lithium salts intermediate.Lithium salts intermediate in the reaction process is unstable, it is necessary to cryo-conservation, simultaneously because having used valence
The butyl lithium of lattice valuableness, the synthesis technology are not suitable for industrialized production.Patent US5488169 successfully reports anti-by format
The method that this kind of organic boride should be synthesized, pentafluorophenyl group magnesium bromide react at room temperature with borating agents such as boron trifluorides
Reaction, obtains four pentafluorophenyl boric acid magnesium salts intermediates, which, which further reacts, obtains corresponding metallocene catalysis
Agent aid organoboron compound.But the patent does not introduce the preparation process of grignard reagent pentafluorophenyl group magnesium bromide, generation
Magnesium salts intermediate is in industry amplification generating process, and magnesium salts is not easy to remove, it is more to remain, and causes catalyst efficiency low.The present invention couple
The technical process is further studied, and reaction process is optimized, and has selected grignard reaction solvent and initiator appropriate, synthesis
Pentafluorophenyl group magnesium bromide synthesizes four pentafluorophenyl boric acid magnesium salts by grignard reaction, then react with potassium reagent and synthesize four phenyl-pentafluorides
Boric acid sylvite, the total moles yield for optimizing technique reach 80% or more, and the product total moles yield under the conditions of optimization process reaches
To 88%, the purity is high of product reaches 99% or more.The four penta phenyl fluoride borons acid potassium salt can be used as among crucial organic boride
Body is used to synthesize the organic boride auxiliary agent of transition-metal catalyst, the polymerization reaction applied to alkene.
Summary of the invention
For the deficiencies in the prior art in production process, the present invention provides a kind of synthesis side of four penta phenyl fluoride boron acid potassium salts
Method.Five bromofluorobenzene of raw material and magnesium chips generate grignard reagent, are reacted in four or five fluoboric acid sylvite of synthesis with borane reagents such as boron trifluorides
Mesosome, the sylvite intermediate can react to obtain triphen carbon four (pentafluorophenyl group) boron with trityl chloride (or n,N-Dimethylaniline)
Hydrochlorate (or N, N- dimethyl puratized agricultural spray four (pentafluorophenyl group) borate) is used as metallocene catalysis agent aid, can be used for the polymerization of alkene
Reaction.Specific technical solution is as follows:
A kind of synthetic method of four penta phenyl fluoride borons acid potassium salt, comprising the following steps:
1) under the protection of nitrogen or inert gas, five bromofluorobenzenes, magnesium chips, solvent I and initiator is added and reacted
In container, reaction temperature and time are controlled, pentafluorophenyl group magnesium bromide grignard reagent is obtained；
2) continue under the protection of nitrogen or inert gas, to the pentafluorophenyl group magnesium bromide grignard reagent described in step 1)
Middle addition solvent II and boronating agent control reaction temperature and time, synthesize four pentafluorophenyl boric acid magnesium salts；Then carry out acid processing and
The processing of potassium reagent, obtains four penta phenyl fluoride boron acid potassium salts.
Specific technology path is as follows:
Wherein, in step 1), the dosage of the magnesium chips is 5~20wt% of the five bromofluorobenzenes quality, preferably 10~
15wt%, more preferably 10~11wt%.The reaction temperature is -10~60 DEG C, preferably -5~40 DEG C, more preferable 0~25 DEG C.
The reaction time is 1~10h, preferably 2~8h, more preferable 2~5h.In step 2), the reaction temperature is 10~90 DEG C, excellent
Select 25~80 DEG C, more preferable 35~65 DEG C.The reaction time is 4~15h, preferably 6~10h, more preferable 6~8h.
As a preferred technical solution, in step 1), the solvent be ether, methyl tertiary butyl ether(MTBE), Isosorbide-5-Nitrae-dioxane,
One of tetrahydrofuran, methyltetrahydrofuran or cyclopentyl methyl ether are a variety of；Preferably tetrahydrofuran, methyltetrahydrofuran or
Cyclopentyl methyl ether；Further preferably cyclopentyl methyl ether.The dosage of the solvent is 1~2 times of the five bromofluorobenzenes quality, excellent
Select 1~1.5 times, more preferably 1.25 times.
As a preferred technical solution, in step 1), the initiator is iodine, 1,2- Bromofume, methyl chloride
One of magnesium, methyl-magnesium-bromide or iodomethane are a variety of；Preferably methyl-magnesium-chloride or iodomethane；Further preferably iodine first
Alkane.The dosage of the initiator be the five bromofluorobenzenes quality 5~20wt%, preferably 10~20wt%, more preferable 15~
20wt%.
As a preferred technical solution, in step 2), the boronating agent is boron chloride dichloromethane solution, boron chloride
One of n-heptane solution, Boron tribromide, Boron tribromide dichloromethane solution, boron trifluoride ether or boron trifluoride tetrahydrofuran
Or it is a variety of；Preferably boron trifluoride ether or boron trifluoride tetrahydrofuran, more excellent is boron trifluoride ether.The use of the boronating agent
Amount is the 10~20wt%, preferably 10~15wt%, more preferable 12~15wt% of the five bromofluorobenzenes quality.
As a preferred technical solution, in step 2), the solvent be toluene, dimethylbenzene, normal heptane, normal octane and/or
One of n -nonane is a variety of；Preferably toluene or normal heptane, more preferably toluene.The dosage of the solvent is five fluorine
2~6 times of bromobenzene quality, preferably 3~5 times, more preferable 3.5~4 times.
As a preferred technical solution, in step 2), the acid processing, used acid reagent is 37wt% concentrated hydrochloric acid,
One of 65wt% concentrated nitric acid, the 98wt% concentrated sulfuric acid, glacial acetic acid or 85wt% phosphoric acid are a variety of；Preferably 37wt% concentrated hydrochloric acid
Or the 98wt% concentrated sulfuric acid, more preferably 37wt% concentrated hydrochloric acid.The dosage of the acid be the five bromofluorobenzenes quality 40~
80wt%, preferably 50~60wt%, more preferable 50~55wt%.
As a preferred technical solution, in step 2), the potassium reagent be potassium chloride, potassium bromide, potassium iodide, potassium nitrate,
One of potassium acid sulfate, potassium sulfate, potassium hydroxide, potassium phosphate, potassium hydrogen phosphate, potassium dihydrogen phosphate, potassium carbonate or saleratus
Or it is a variety of；Preferably potassium phosphate, potassium carbonate or saleratus；More preferably potassium phosphate or potassium carbonate.The dosage of the potassium reagent
For 5~30wt% of the five bromofluorobenzenes quality, preferably 10~20wt%, more preferable 10~15wt%.
The beneficial effects of the present invention are:
For compared with the prior art, have following advantage:
1, four penta phenyl fluoride borons acid potassium salt synthesis of the present invention uses grignard reaction, and synthesis technology is simple, reaction raw materials
It is easy to get, is suitble to industrialized production.Four penta phenyl fluoride boron acid potassium salts belong to synthesis of the organic boride intermediate for boron ligand, and boron is matched
Body can form complex with transition metal element (such as Cu, Co, Ni, Ti, Zr), be applied to olefin polymerization catalysis, have huge
Big economic value.
2, four penta phenyl fluoride borons acid potassium salt of the present invention, since potassium ion is easy to remove and (such as wash), in boron ligand
The boron ligand purity of the residual of non-metallic ion in synthesis process, synthesis is high, meets in olefin polymerization process to catalyst
Active pharmaceutical.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with embodiment, to skill of the invention
Art scheme is clearly and completely described.
Embodiment 1
Under nitrogen protection, it weighs 385G tetrahydrofuran and 30.5G magnesium chips is added in 5L reaction kettle.Reactor temperature
It is down to 0 DEG C, 1, the 2- Bromofume of 53G is added.Stop cooling, temperature is warmed to room temperature (25 DEG C).At room temperature, start to drip
Add five bromofluorobenzene of 306G, the used time 70 minutes.Continue stirring 1 hour at room temperature.Then the toluene and 41G of addition 1170 are borontrifluoride
Diethyl etherate stirs 5 hours at 35 DEG C of reactor temperature.Then reactor temperature rises to 60 DEG C and continues to be stirred to react
2 hours.Stop reaction, 37% concentrated hydrochloric acid of 750G water and 160G is added in the reactive mixture, continues stirring up to no gas
It releases.Lower layer's water phase is separated, 850G water and 40G potassium carbonate is added in organic phase, continues stirring 1 hour.Lower layer's water phase is separated, is had
950G water is added in machine phase, vacuum distillation removes low boiling point organic solvent.Upper organic phase is separated, lower layer's water phase is kept the temperature at 5 DEG C
Crystallization 4 hours.Vacuum filter, washing, obtains solid crude product.Crude product is dried in vacuo 10 hours at 50 DEG C and obtains white powder solid
178G (purity 99%, molar yield 80%).
Embodiment 2
Under nitrogen protection, it weighs 385G cyclopentyl methyl ether and 30.5G magnesium chips is added in 5L reaction kettle.It is warm in reaction kettle
Degree is down to 0 DEG C, and 1, the 2- Bromofume of 53G is added.Stop cooling, temperature is warmed to room temperature (25 DEG C).At room temperature, start
Dropwise addition five bromofluorobenzene of 306G, the used time 60 minutes.Continue stirring 1 hour at room temperature.Then 1170 toluene and 41G trifluoro is added
Change diethyl etherate, is stirred 5 hours at 35 DEG C of reactor temperature.Then reactor temperature rises to 60 DEG C and continues to stir instead
It answers 2 hours.Stop reaction, 37% concentrated hydrochloric acid of 750G water and 160G is added in the reactive mixture, continues stirring up to no gas
Body is released.Lower layer's water phase is separated, 850G water and 40G potassium carbonate is added in organic phase, continues stirring 1 hour.Lower layer's water phase is separated,
950G water is added in organic phase, vacuum distillation removes low boiling point organic solvent.Upper organic phase is separated, lower layer's water phase is protected at 5 DEG C
Temperature crystallization 4 hours.Vacuum filter, washing, obtains solid crude product.Crude product obtains white powder for 10 hours in 50 DEG C of vacuum drying and consolidates
Body 189G (purity 99%, molar yield 85%).
Embodiment 3
Under nitrogen protection, it weighs 385G cyclopentyl methyl ether and 30.5G magnesium chips is added in 5L reaction kettle.It is warm in reaction kettle
Degree is down to 0 DEG C, and the iodomethane of 53G is added.Stop cooling, temperature is warmed to room temperature (25 DEG C).At room temperature, start to be added dropwise
Five bromofluorobenzene of 306G, the used time 60 minutes.Continue stirring 1 hour at room temperature.Then 1170 toluene and 41G boron trifluoride is added
Etherate stirs 5 hours at 35 DEG C of reactor temperature.Then reactor temperature rises to 60 DEG C and continues to be stirred to react 2
Hour.Stop reaction, 37% concentrated hydrochloric acid of 750G water and 160G is added in the reactive mixture, continues stirring up to no gas is put
Out.Lower layer's water phase is separated, 850G water and 40G potassium carbonate is added in organic phase, continues stirring 1 hour.Lower layer's water phase is separated, it is organic
950G water is added in phase, vacuum distillation removes low boiling point organic solvent.Upper organic phase is separated, lower layer's water phase is tied in 5 DEG C of heat preservations
It is 4 hours brilliant.Vacuum filter, washing, obtains solid crude product.Crude product is dried in vacuo 10 hours at 50 DEG C and obtains white powder solid
(195.5G purity 99%, molar yield 88%).
Embodiment 4
Under nitrogen protection, it weighs 385G cyclopentyl methyl ether and 30.5G magnesium chips is added in 5L reaction kettle.It is warm in reaction kettle
Degree is down to 0 DEG C, and the iodomethane of 53G is added.Stop cooling, temperature is warmed to room temperature (25 DEG C).At room temperature, start to be added dropwise
Five bromofluorobenzene of 306G, the used time 60 minutes.Continue stirring 1 hour at room temperature.Then the toluene and 39.9G of addition 1170 are borontrifluoride
Boron tetrahydrofuran complex stirs 5 hours at 35 DEG C of reactor temperature.Then reactor temperature rises to 60 DEG C and continues to stir
Reaction 2 hours.Stop reaction, 37% concentrated hydrochloric acid of 750G water and 160G is added in the reactive mixture, continues stirring until nothing
Gas is released.Lower layer's water phase is separated, 850G water and 40G potassium carbonate is added in organic phase, continues stirring 1 hour.Separate lower water
Phase, 950G water is added in organic phase, and vacuum distillation removes low boiling point organic solvent.Upper organic phase is separated, lower layer's water phase is at 5 DEG C
Heat preservation crystallization 4 hours.Vacuum filter, washing, obtains solid crude product.Crude product is dried in vacuo 10 hours at 50 DEG C and obtains white powder
Solid 186.5G (purity 99%, molar yield 84%).
Embodiment 5
Under nitrogen protection, it weighs 385G methyltetrahydrofuran and 30.5G magnesium chips is added in 5L reaction kettle.In reaction kettle
Temperature is down to 0 DEG C, and the iodomethane of 53G is added.Stop cooling, temperature is warmed to room temperature (25 DEG C).At room temperature, start to be added dropwise
Five bromofluorobenzene of 306G, the used time 60 minutes.Continue stirring 1 hour at room temperature.Then 1170 toluene and 41G boron trifluoride is added
Etherate stirs 5 hours at 35 DEG C of reactor temperature.Then reactor temperature rises to 60 DEG C and continues to be stirred to react 2
Hour.Stop reaction, 37% concentrated hydrochloric acid of 750G water and 160G is added in the reactive mixture, continues stirring up to no gas is put
Out.Lower layer's water phase is separated, 850G water and 40G potassium carbonate is added in organic phase, continues stirring 1 hour.Lower layer's water phase is separated, it is organic
950G water is added in phase, vacuum distillation removes low boiling point organic solvent.Upper organic phase is separated, lower layer's water phase is tied in 5 DEG C of heat preservations
It is 4 hours brilliant.Vacuum filter, washing, obtains solid crude product.Crude product is dried in vacuo 10 hours at 50 DEG C and obtains white powder solid
191G (purity 99%, molar yield 86%).
Embodiment 6
Under nitrogen protection, it weighs 385G cyclopentyl methyl ether and 30.5G magnesium chips is added in 5L reaction kettle.It is warm in reaction kettle
Degree is down to 0 DEG C, and the iodomethane of 53G is added.Stop cooling, temperature is warmed to room temperature (25 DEG C).At room temperature, start to be added dropwise
Five bromofluorobenzene of 306G, the used time 60 minutes.Continue stirring 1 hour at room temperature.Then 1170 toluene and 41G boron trifluoride is added
Etherate stirs 5 hours at 35 DEG C of reactor temperature.Then reactor temperature rises to 60 DEG C and continues to be stirred to react 2
Hour.Stop reaction, 37% concentrated hydrochloric acid of 750G water and 160G is added in the reactive mixture, continues stirring up to no gas is put
Out.Lower layer's water phase is separated, 850G water and 61.5G potassium phosphate is added in organic phase, continues stirring 1 hour.Lower layer's water phase is separated, is had
950G water is added in machine phase, vacuum distillation removes low boiling point organic solvent.Upper organic phase is separated, lower layer's water phase is kept the temperature at 5 DEG C
Crystallization 4 hours.Vacuum filter, washing, obtains solid crude product.Crude product is dried in vacuo 10 hours at 50 DEG C and obtains white powder solid
195.0G (purity 99%, molar yield 88%).
It is up to it can be seen from the above embodiments using four penta phenyl fluoride boron acid potassium salt purity made from the method for the present invention
99%, for molar yield up to 80% or more, the product total moles yield under the conditions of optimization process reaches 88%, effectively overcomes
The more problem of the intermediate residual generated in production process, improves the polymerization reaction of four penta phenyl fluoride boron acid potassium salts for alkene
The catalytic efficiency of catalyst.
It is obvious to a person skilled in the art that invention is not limited to the details of the above exemplary embodiments, Er Qie
In the case where without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter
From the point of view of which point, the present embodiments are to be considered as illustrative and not restrictive.Although in addition, it should be understood that originally
Specification is described in terms of embodiments, but only includes not one technical solution, and this narrating mode of specification is only
It is only for clarity that the skilled in the art should refer to the specification as a whole, the technical solution in embodiment can also
To be properly combined, form other embodiments that can be understood by those skilled in the art.
Claims (10)
1. a kind of synthetic method of four penta phenyl fluoride boron acid potassium salts, it is characterised in that: the following steps are included:
1) under the protection of nitrogen or inert gas, reaction vessel is added in five bromofluorobenzenes, magnesium chips, solvent I and initiator
In, reaction temperature and time are controlled, pentafluorophenyl group magnesium bromide grignard reagent is obtained；
2) continue under the protection of nitrogen or inert gas, into the grignard reagent of pentafluorophenyl group magnesium bromide described in step 1)
Solvent II and boronating agent is added, controls reaction temperature and time, synthesizes four pentafluorophenyl boric acid magnesium salts；Then sour processing and potassium are carried out
Reagent processing, obtains four penta phenyl fluoride boron acid potassium salts.
2. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 1)
The dosage of magnesium chips is 5~20wt% of the five bromofluorobenzenes quality.
3. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 1)
Reaction temperature is -10~60 DEG C, and the reaction time is 1~10h.
4. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 2
Reaction temperature is -10~60 DEG C, and the reaction time is 4~15h.
5. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 1)
Solvent I is one in ether, methyl tertiary butyl ether(MTBE), 1,4- dioxane, tetrahydrofuran, methyltetrahydrofuran or cyclopentyl methyl ether
Kind is a variety of.
6. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 1)
Initiator is one of iodine, glycol dibromide, methyl-magnesium-chloride, methyl-magnesium-bromide or iodomethane or a variety of.
7. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 2
Solvent II is one of toluene, dimethylbenzene, normal heptane, normal octane or n -nonane or a variety of.
8. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 2
Boronating agent be boron chloride dichloromethane solution, boron chloride n-heptane solution, Boron tribromide, Boron tribromide dichloromethane solution,
One of boron trifluoride ether or boron trifluoride tetrahydrofuran are a variety of.
9. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 2
Acid processing acid used is 37wt% concentrated hydrochloric acid, one of 65wt% concentrated nitric acid, the 98wt% concentrated sulfuric acid, glacial acetic acid or 85wt% phosphoric acid
Or it is a variety of.
10. the synthetic method of four penta phenyl fluoride borons acid potassium salt according to claim 1, it is characterised in that: described in step 2
Potassium reagent be potassium chloride, potassium bromide, potassium iodide, potassium nitrate, potassium acid sulfate, potassium sulfate, potassium hydroxide, potassium phosphate, potassium hydrogen phosphate,
One of potassium dihydrogen phosphate, potassium carbonate or saleratus are a variety of.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111943968A (en) * | 2020-09-02 | 2020-11-17 | 陆海峰 | Process for preparing tetrakis (pentafluorophenyl) borate |
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| CN101265269A (en) * | 2008-03-21 | 2008-09-17 | 浙江工业大学 | Method for preparing pentafluorophenyl boric acid |
| CN101863913A (en) * | 2010-06-24 | 2010-10-20 | 上海化工研究院 | Preparation method of fluorinated aryl-containing boron compound |
| CN103304587A (en) * | 2013-06-25 | 2013-09-18 | 上海恩氟佳科技有限公司 | Preparation method of tri(pentafluorophenyl) borane |
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| US5488169A (en) * | 1992-12-28 | 1996-01-30 | Tosoh Akzo Corporation | Method of producing tetrakis(pentafluorophenyl)borate derivatives using pentafluorophenylmagnesium derivatives |
| US6169208B1 (en) * | 1999-12-03 | 2001-01-02 | Albemarle Corporation | Process for producing a magnesium di[tetrakis(Faryl)borate] and products therefrom |
| CN101265269A (en) * | 2008-03-21 | 2008-09-17 | 浙江工业大学 | Method for preparing pentafluorophenyl boric acid |
| CN101863913A (en) * | 2010-06-24 | 2010-10-20 | 上海化工研究院 | Preparation method of fluorinated aryl-containing boron compound |
| CN103304587A (en) * | 2013-06-25 | 2013-09-18 | 上海恩氟佳科技有限公司 | Preparation method of tri(pentafluorophenyl) borane |
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| CN111943968A (en) * | 2020-09-02 | 2020-11-17 | 陆海峰 | Process for preparing tetrakis (pentafluorophenyl) borate |
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Application publication date: 20190723 |