CN109721567A - A kind of method of catalyst and catalysis preparation glycidyl methacrylate - Google Patents
A kind of method of catalyst and catalysis preparation glycidyl methacrylate Download PDFInfo
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- CN109721567A CN109721567A CN201811524835.1A CN201811524835A CN109721567A CN 109721567 A CN109721567 A CN 109721567A CN 201811524835 A CN201811524835 A CN 201811524835A CN 109721567 A CN109721567 A CN 109721567A
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- ionic liquid
- transfer catalyst
- epoxychloropropane
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Abstract
The invention discloses a kind of catalyst and the methods of catalysis preparation glycidyl methacrylate, including the stage of reaction and separation phase.The stage of reaction is added ionic liquid collaboration phase transfer catalyst and is catalyzed, and obtains glycidyl methacrylate crude product；Separation phase is through filtering, rectification under vacuum removing epoxychloropropane, epoxy prapanol by-product, finally obtained glycidyl methacrylate purified product.The present invention cooperates with phase transfer catalyst using ionic liquid, and compared to the method for single use phase transfer catalyst, epoxychloropropane dosage reduces about 1/2, greatly reduces the concentration of epoxychloropropane in the energy consumption and waste liquid that recycle excess epoxy chloropropane in distillation process；Ionic liquid is added simultaneously and solves the problems, such as the occurrence of phase transfer catalyst is gradually precipitated, avoids stifled tower when subsequent continuous rectification removes epoxychloropropane in the process.
Description
Technical field
The present invention relates to a kind of catalyst and the methods of catalysis preparation glycidyl methacrylate, belong to Chemical Engineering Technology
Field.
Background technique
Glycidyl methacrylate (abbreviation GMA), molecular structure contain vinyl and epoxide ring, the two groups are living
Property it is all very high, a variety of reactions can be carried out and generate linear polymers or crosslinked, be widely used in powdery paints, synthetic resin,
Plastics, adhesive, medical material etc. can effectively improve heat resistance, waterproof performance, adhesive strength, the compatibility of material.
The production method of glycidyl methacrylate industrially mainly uses metering system acid alkali metal at present
Salt and excessive epoxychloropropane, carried out under the action of phase transfer catalyst a step lactate synthesis be made, the method yield compared with
Height, up to 90% or more, but this method needs epoxychloropropane significantly excessive, general metering system acid alkali metal salt and epoxy chlorine
Propane molar ratio is 1:6~1:8, as patent of invention CN1569823A discloses a kind of preparation of glycidyl methacrylate
Method, Sodium methacrylate and epoxychloropropane carry out anti-under conditions of phase transfer catalyst tetramethylethylenediamine is used alone
It answers, Sodium methacrylate and epoxychloropropane molar ratio are 1:7.3.Epoxychloropropane price is more expensive and to human health damage
Greatly, energy consumption can be larger when rectification under vacuum reuse epoxychloropropane after if natural ecosystems are destroyed big, and dosage is excessive.
It needs to carry out separation and purification, such as patent of invention after obtaining the crude reaction liquid of glycidyl methacrylate
CN105218487A reports a kind of production method of glycidyl methacrylate, and thick ester feed liquid is returned through thin film evaporation equipment
Solvent is received, is evaporated under reduced pressure using molecular distillation apparatus, obtains target product, this process simplify production procedures and industry to set
It is standby, it is easy to operate, but there are catalyst, and risk is precipitated for this method, and the catalyst accumulation being precipitated after long time running is easily damaged
Key equipment scraper film evaporator and molecular distillation apparatus.
Ionic liquid is a kind of ionic compound being in a liquid state at room temperature, also referred to as low temperature molten salt, ionic liquid due to
It is forced down with steam, not volatile, the features such as liquid condition range is wide, and thermal stability is good is a kind of environmentally friendly solvent.This hair
It is bright that the dissolution characteristics of organic salt are promoted ionic liquid and phase transfer catalyst collaboration use in reaction using ionic liquid
Mass transfer between solid liquid phase is added ionic liquid and can guarantee continuous rectification process to reduce the dosage of raw material epoxychloropropane
The case where quaternary ammonium salt phase transfer catalyst will not be precipitated, and rectifying column is not in blocking.
Summary of the invention
The present invention separates work for the existing phase transfer catalysis (PTC) preparation process of glycidyl methacrylate and continuous rectification
Deficiency present in skill is improved, and is provided a kind of more efficient concerted catalysis method, is overcome single use quaternary ammonium salt phase
Epoxychloropropane dosage excessive problem when transfer catalyst.Quaternary ammonium salt phase transfer catalyst is applied to such solid-liquid reaction, needs
The metering system acid alkali metal salt for acting on solid phase, destroys its lattice, captures methacrylic acid radical ion therein and liquid phase
Epoxychloropropane is reacted, to realize the reaction between solid liquid phase, the catalysis of single use quaternary ammonium salt phase transfer catalyst is solid
Reaction generally requires large excess of epoxychloropropane between liquid phase, adequately surrounds infiltration metering system acid alkali metal salt ability
Realize the raising of metering system acid alkali metal salt conversion ratio.
Ionic liquid is added on this basis and carries out concerted catalysis by the present invention, using ionic liquid to metering system soda acid gold
Belong to the dissolution characteristics of salt, so that quaternary ammonium salt phase transfer catalyst destroys lattice and is more easier, so that quaternary ammonium salt phase transfer is urged
The efficiency that agent captures methacrylic acid radical ion improves, and more efficient mass transfer reaction, epoxy chloropropionate can be achieved between solid liquid phase
The dosage of alkane can effectively reduce.
Furthermore quaternary ammonium salt phase transfer catalyst is due to tower bottom after having separated epoxychloropropane during subsequent continuous rectification
There is no solvent epoxychloropropane, it may appear that precipitation phenomenon, if the stage of reaction ionic liquid is added, ionic liquid can one
It is same to enter continuous rectification system, the characteristic that can dissolve quaternary ammonium salt using it and be precipitated, during avoidable continuous rectification
Since catalyst precipitation causes tower long-term operation that stopping state occurs.
To achieve the above object, the present invention provides a kind of ionic liquid collaboration Catalyzed By Phase-transfer Catalyst and prepares metering system
The method of acid glycidyl ester, comprising the following steps:
(1) metering system acid alkali metal salt, epoxychloropropane are in polymerization inhibitor, quaternary ammonium salt phase transfer catalyst, ionic liquid
It is reacted under the conditions of existing, glycidyl methacrylate saliferous crude liquid is prepared.
(2) decompressing and continuous rectifying is carried out after crude reaction liquid being filtered out solid salt by continuous filter plant, isolates epoxy
The glycidyl methacrylate product of purity > 99% is obtained after chloropropane, epoxy prapanol by-product.
Further, in step (1) of the present invention, under ionic liquid collaboration phase transfer catalyst effect, methyl-prop
Olefin(e) acid alkali metal salt and epoxychloropropane molar ratio are 1:1.5~5, preferably 1:2~3.
Preferably, polymerization inhibitor is p-hydroxyanisole, hydroquinone, phenthazine, N, N bis- in step (1) of the present invention
One or more of butyl aminodithioformic acid copper, further preferably phenthazine, dosage are metering system soda acid gold
Belong to the 0.5-3wt%, preferably 1~2wt% of salt.
Preferably, quaternary ammonium salt phase transfer catalyst is triethyl benzyl ammonia chloride, tetraethyl in step (1) of the present invention
Ammonium chloride, tetrabutylammonium bromide, tetrabutylammonium chloride, dodecyl trimethyl ammonium chloride, in tetradecyl trimethyl ammonium chloride
One or more, further preferably triethyl benzyl ammonia chloride, dosage be metering system acid alkali metal salt 0.1~
2wt%, preferably 0.15~1wt%.
Preferably, step (1) intermediate ion liquid of the present invention is benzyl triethylamine tetrafluoroborate, benzyl triethylamine six
One or more of fluorophosphate, benzyl triethylamine disulfate, benzyl triethylamine imidazole salts, dosage are methacrylic acid
1~10wt% of alkali metal salt, further preferably 3~5wt%.
Further, in step (1) of the present invention, reaction temperature is 90~110 DEG C, and the reaction time is 1~3h.
Continuous filter plant is drum pressurizing filter in step (2) of the present invention, disk plate centrifuge, horizontal spiral sink
One of centrifuge drops, and wherein drum pressurizing filter operating pressure is 0.2~0.3Mpa (A), revolving speed is 0.5~2rpm,
Disk plate centrifuge revolving speed is 4000~6000rpm, and horizontal type screw settling centrifuge revolving speed is 2500~3000rpm.Generally, thick anti-
Liquid is answered to enter the crude reaction liquid temperature of continuous filter plant at 20~40 DEG C.
Filtrate continuous feed obtained by continuous filter plant enters continuous rectification equipment in step (2) of the present invention, continuously
Rectifying device is composed in series by three rectifying columns, the rectification under vacuum under the conditions of 60~80 DEG C, 4~5kPa (A) of first rectifying column
It removes excess epoxy chloropropane to be recycled, reuse epoxychloropropane purity > 99%；Second rectifying column is 80~90
DEG C, rectification under vacuum removes epoxy prapanol by-product under the conditions of 3~4kPa (A)；Third rectifying column is in 100~110 DEG C, 2-3kPa
(A), purified product glycidyl methacrylate, purity > is made in rectification under vacuum under the conditions of preferably 2.5kPa (A)
99%, it is preferable that the theoretical cam curve of first tower is 6-10, and the theoretical cam curve of preferably 8, second towers is 12-18, preferably
15, the theoretical cam curve of third tower be 12-18, preferably 15.
Invention further provides one kind to prepare methyl for metering system acid alkali metal salt and epichlorohydrin reaction
The catalyst of glycidyl acrylate comprising the combination of quaternary ammonium salt phase transfer catalyst, ionic liquid, wherein ionic liquid
Dosage is 1~10wt% of metering system acid alkali metal salt, and preferably 3~5wt%, phase transfer catalyst dosage is methacrylic acid
0.1~2wt% of alkali metal salt, preferably 0.15~1wt%.Generally, the quality of quaternary ammonium salt phase transfer catalyst and ionic liquid
Than for 1:0.5~10.
Preferably, quaternary ammonium salt phase transfer catalyst is triethyl benzyl ammonia chloride, etamon chloride, tetrabutyl phosphonium bromide
One of ammonium, tetrabutylammonium chloride, dodecyl trimethyl ammonium chloride, tetradecyl trimethyl ammonium chloride are a variety of, into one
Step is preferably triethyl benzyl ammonia chloride.
Preferably, ionic liquid is benzyl triethylamine tetrafluoroborate, benzyl triethylamine hexafluorophosphate, benzyl triethylamine
One or more of disulfate, benzyl triethylamine imidazole salts.
Present invention uses ionic liquid collaboration Catalyzed By Phase-transfer Catalysts to prepare glycidyl methacrylate, and existing
There is one-step method preparation glycidyl methacrylate technique to compare, has the advantages that
1, due to having used ionic liquid collaboration phase transfer catalyst to be catalyzed, solid liquid phase mass transfer is more abundant, required ring
Oxygen chloropropane dosage greatly reduces, and reduces the energy consumption of reuse epoxychloropropane, reduces the generation of the three wastes, and production cost can obtain
To reduction.
2, since system introduces ionic liquid, quaternary ammonium salt phase transfer catalyst therein will not taking off with epoxychloropropane
It removes and is precipitated, ensure that the stable operation of entire continuous rectification process, improve the stability of technique, be suitable for scale serialization
Produce glycidyl methacrylate.
Detailed description of the invention
Fig. 1 is continuous rectification equipment schematic diagram of the present invention, is composed in series by three rectifying columns, first rectifying column 60~
80 DEG C, rectification under vacuum removes excess epoxy chloropropane and is recycled under the conditions of 4~5kPa (A), and reuse epoxychloropropane is pure
Spend > 99%；The rectification under vacuum under the conditions of 80~90 DEG C, 3~4kPa (A) of second rectifying column removes epoxy prapanol by-product；The
Purified product methyl propenoic acid glycidyl is made in rectification under vacuum under the conditions of 100~110 DEG C, 2.5kPa (A) of three rectifying columns
Ester, purity > 99%.
Specific embodiment
It will be further elucidated by the following examples the present invention, but be not limited to the embodiment.
Comparative example 1
The stage of reaction: into 250L reaction kettle put into 54kg Sodium methacrylate powder, 139kg epoxychloropropane,
0.35kg triethyl benzyl ammonia chloride, 0.6kg phenthazine.Stirring heating is reacted, and control temperature of reaction kettle is 90~95 DEG C,
It cools after insulation reaction 3h.
Separation phase: crude reaction liquid is cooled to 40 DEG C, squeezes into horizontal type screw settling centrifuge by pump, setting revolving speed is
2500rpm, filtrate persistently squeeze into continuous rectification equipment by pump, and first theoretical number of plates of rectifying tower is 8, controlled at 70
DEG C, tower top pressure is 4kPa (A), and tower top steams light component epoxychloropropane and carries out reuse, and tower bottom liquid continuously enters the by pump
Two rectifying columns, theoretical cam curve 15, controlled at 90 DEG C, tower top pressure is that 3kPa (A) rectification under vacuum removes epoxy third
Alcohol by-product, tower bottom liquid continuously enter third rectifying column by pump, theoretical cam curve 15, controlled at 110 DEG C, tower top
Pressure is 2.5kPa (A), obtains colorless and transparent glycidyl methacrylate product 52kg, purity 99.2%, yield 72.6%.
Comparative example 2
The stage of reaction: 54kg Sodium methacrylate powder, 139kg epoxychloropropane, 0.6kg are put into 250L reaction kettle
Phenthazine, 2kg benzyl triethylamine hexafluorophosphate.Stirring heating is reacted, and control temperature of reaction kettle is 90~95 DEG C, heat preservation
It cools after reaction 3h.
Separation phase: crude reaction liquid is cooled to 40 DEG C, squeezes into horizontal type screw settling centrifuge by pump, setting revolving speed is
2500rpm, filtrate persistently squeeze into continuous rectification equipment by pump, and first theoretical number of plates of rectifying tower is 8, controlled at 70
DEG C, tower top pressure is 4kPa (A), and tower top steams light component epoxychloropropane and carries out reuse, and tower bottom liquid continuously enters the by pump
Two rectifying columns, theoretical cam curve 15, controlled at 90 DEG C, tower top pressure is that 3kPa (A) rectification under vacuum removes epoxy third
Alcohol by-product, tower bottom liquid continuously enter third rectifying column by pump, theoretical cam curve 15, controlled at 110 DEG C, tower top
Pressure is 2.5kPa (A), obtains colorless and transparent glycidyl methacrylate product 25.4kg, purity 98.8%, yield
35.3%.
Embodiment 1
The stage of reaction: into 250L reaction kettle put into 54kg Sodium methacrylate powder, 139kg epoxychloropropane,
0.35kg triethyl benzyl ammonia chloride, 0.6kg phenthazine, 2kg benzyl triethylamine hexafluorophosphate.Stirring heating is reacted,
Controlling temperature of reaction kettle is 90~95 DEG C, is cooled after insulation reaction 3h.
Separation phase: crude reaction liquid is cooled to 40 DEG C, squeezes into horizontal type screw settling centrifuge by pump, setting revolving speed is
2500rpm, filtrate persistently squeeze into continuous rectification equipment by pump, and first theoretical number of plates of rectifying tower is 8, controlled at 70
DEG C, tower top pressure is 4kPa (A), and tower top steams light component epoxychloropropane and carries out reuse, and tower bottom liquid continuously enters the by pump
Two rectifying columns, theoretical cam curve 15, controlled at 90 DEG C, tower top pressure is that 3kPa (A) rectification under vacuum removes epoxy third
Alcohol by-product, tower bottom liquid continuously enter third rectifying column by pump, theoretical cam curve 15, controlled at 110 DEG C, tower top
Pressure is 2.5kPa (A), obtains colorless and transparent glycidyl methacrylate product 69.2kg, purity 99.3%, yield
96.8%.
Embodiment 2
The stage of reaction: into 250L reaction kettle put into 54kg Sodium methacrylate powder, 139kg epoxychloropropane,
0.35kg triethyl benzyl ammonia chloride, 0.6kg phenthazine, 1kg benzyl triethylamine tetrafluoroborate, 0.6kg benzyl triethylamine miaow
Azoles salt.Stirring heating is reacted, and control temperature of reaction kettle is 90~95 DEG C, is cooled after insulation reaction 2h.
Separation phase: crude reaction liquid is cooled to 40 DEG C, squeezes into horizontal type screw settling centrifuge by pump, setting revolving speed is
2500rpm, filtrate persistently squeeze into continuous rectification equipment by pump, and first theoretical number of plates of rectifying tower is 8, controlled at 70
DEG C, tower top pressure is 4kPa (A), and tower top steams light component epoxychloropropane and carries out reuse, and tower bottom liquid continuously enters the by pump
Two rectifying columns, theoretical cam curve 15, controlled at 90 DEG C, tower top pressure is that 3kPa (A) rectification under vacuum removes epoxy third
Alcohol by-product, tower bottom liquid continuously enter third rectifying column by pump, theoretical cam curve 15, controlled at 110 DEG C, tower top
Pressure is 2.5kPa (A), obtains colorless and transparent glycidyl methacrylate product 69.9kg, purity 99.2%, yield
97.7%.
Embodiment 3
The stage of reaction: into 250L reaction kettle put into 54kg Sodium methacrylate powder, 139kg epoxychloropropane,
0.35kg triethyl benzyl ammonia chloride, 0.6kg phenthazine, 1kg benzyl triethylamine disulfate, 1kg benzyl triethylamine imidazole salts.
Stirring heating is reacted, and control temperature of reaction kettle is 90~95 DEG C, is cooled after insulation reaction 2.5h.
Separation phase: crude reaction liquid is cooled to 35 DEG C, squeezes into disc centrifuge by pump, and setting revolving speed is 5000rpm,
Filtrate persistently squeezes into continuous rectification equipment by pump, and first theoretical number of plates of rectifying tower is 8, controlled at 70 DEG C, tower top
Pressure is 4kPa (A), and tower top steams light component epoxychloropropane and carries out reuse, and tower bottom liquid continuously enters second rectifying by pump
Tower, theoretical cam curve 15, controlled at 90 DEG C, tower top pressure is that 3kPa (A) rectification under vacuum removes epoxy prapanol by-product,
Tower bottom liquid continuously enters third rectifying column by pump, theoretical cam curve 15, and controlled at 110 DEG C, tower top pressure is
2.5kPa (A) obtains colorless and transparent glycidyl methacrylate product 70.3kg, purity 99.4%, yield 98.4%.
Embodiment 4
The stage of reaction: 54kg Sodium methacrylate powder, 139kg epoxychloropropane, 0.1kg are put into 250L reaction kettle
Triethyl benzyl ammonia chloride, 0.6kg phenthazine, 1kg benzyl triethylamine disulfate, 1.5kg benzyl triethylamine imidazole salts.Stirring
Heating is reacted, and control temperature of reaction kettle is 90~95 DEG C, is cooled after insulation reaction 2h.
Separation phase: crude reaction liquid is cooled to 35 DEG C, squeezes into disc centrifuge by pump, and setting revolving speed is 6000rpm,
Filtrate persistently squeezes into continuous rectification equipment by pump, and first theoretical number of plates of rectifying tower is 8, controlled at 70 DEG C, tower top
Pressure is 4kPa (A), and tower top steams light component epoxychloropropane and carries out reuse, and tower bottom liquid continuously enters second rectifying by pump
Tower, theoretical cam curve 15, controlled at 90 DEG C, tower top pressure is that 3kPa (A) rectification under vacuum removes epoxy prapanol by-product,
Tower bottom liquid continuously enters third rectifying column by pump, theoretical cam curve 15, and controlled at 110 DEG C, tower top pressure is
2.5kPa (A) obtains colorless and transparent glycidyl methacrylate product 70.1kg, purity 99.2%, yield 97.9%.
Embodiment 5
The stage of reaction: 54kg Sodium methacrylate powder, 139kg epoxychloropropane, 0.1kg are put into 250L reaction kettle
Triethyl benzyl ammonia chloride, 0.6kg phenthazine, 2.7kg benzyl triethylamine disulfate.Stirring heating is reacted, and control is anti-
Answering kettle temperature degree is 90~95 DEG C, is cooled after insulation reaction 2h.
Separation phase: crude reaction liquid is cooled to 40 DEG C, squeezes into disc centrifuge by pump, and setting revolving speed is 6000rpm,
Filtrate persistently squeezes into continuous rectification equipment by pump, and first theoretical number of plates of rectifying tower is 8, controlled at 70 DEG C, tower top
Pressure is 4kPa (A), and tower top steams light component epoxychloropropane and carries out reuse, and tower bottom liquid continuously enters second rectifying by pump
Tower, theoretical cam curve 15, controlled at 90 DEG C, tower top pressure is that 3kPa (A) rectification under vacuum removes epoxy prapanol by-product,
Tower bottom liquid continuously enters third rectifying column by pump, theoretical cam curve 15, and controlled at 110 DEG C, tower top pressure is
2.5kPa (A) obtains colorless and transparent glycidyl methacrylate product 68.8kg, purity 99.4%, yield 96.3%.
Claims (10)
1. a kind of method of ionic liquid collaboration Catalyzed By Phase-transfer Catalyst preparation glycidyl methacrylate comprising:
(1) metering system acid alkali metal salt, epoxychloropropane exist in polymerization inhibitor, quaternary ammonium salt phase transfer catalyst, ionic liquid
Under conditions of react, glycidyl methacrylate saliferous crude liquid is prepared；
(2) decompressing and continuous rectifying is carried out after crude reaction liquid being filtered out solid salt by continuous filter plant, isolates epoxy chloropropionate
Glycidyl methacrylate product is obtained after alkane, epoxy prapanol by-product.
2. according to the method described in claim 1, it is characterized in that, in the step (1), ionic liquid collaboration quaternary ammonium salt phase turn
Under shifting catalyst effect, metering system acid alkali metal salt and epoxychloropropane molar ratio are 1:1.5~5, preferably 1:2~3.
3. method according to claim 1 or 2, characterized in that polymerization inhibitor is p-hydroxyanisole, hydroquinone, pheno thiophene
Piperazine, N, one or more of N copper dibutyldithiocarbamate, it is preferable that polymerization inhibitor dosage is metering system soda acid gold
Belong to the 0.5-3wt%, preferably 1~2wt% of salt.
4. method according to any one of claim 1-3, characterized in that ionic liquid is benzyl triethylamine tetrafluoro boric acid
One or more of salt, benzyl triethylamine hexafluorophosphate, benzyl triethylamine disulfate, benzyl triethylamine imidazole salts；It is excellent
Selection of land, ionic liquid dosage are the 1~10wt%, preferably 3~5wt% of metering system acid alkali metal salt.
5. method according to any of claims 1-4, characterized in that quaternary ammonium salt phase transfer catalyst is triethyl group benzyl
Ammonium chloride, etamon chloride, tetrabutylammonium bromide, tetrabutylammonium chloride, dodecyl trimethyl ammonium chloride, myristyl
One or more of trimethyl ammonium chloride；Preferably, quaternary ammonium salt phase transfer catalyst dosage is metering system acid alkali metal salt
0.1~2wt%, preferably 0.15~1wt%.
6. method according to any one of claims 1-5, characterized in that the reaction temperature of step (1) is 90~110
DEG C, the reaction time is 1~3h.
7. method according to claim 1 to 6, characterized in that separation phase enters the thick of continuous filter plant
Reacting liquid temperature is at 20~40 DEG C.
8. method according to any one of claims 1-7, characterized in that continuous filter plant is rotary drum pressure filtration
One of machine, disk plate centrifuge, horizontal type screw settling centrifuge.
9. method according to claim 1 to 8, characterized in that at 60~80 DEG C, 4~5kPa (A) decompression is smart
Distillation goes excess epoxy chloropropane to be recycled, and by-product epoxy prapanol subtracts under the conditions of 80~90 DEG C, 3~4kPa (A)
Rectifying removing is pressed, finally rectification under vacuum under the conditions of 100~110 DEG C, 2~3kPa (A) obtains the contracting of purified product methacrylic acid
Water glyceride, purity > 99%.
10. a kind of prepare urging for glycidyl methacrylate for metering system acid alkali metal salt and epichlorohydrin reaction
Agent comprising the combination of quaternary ammonium salt phase transfer catalyst, ionic liquid, wherein ionic liquid dosage is metering system soda acid
1~10wt% of metal salt, preferably 3~5wt%, phase transfer catalyst dosage be metering system acid alkali metal salt 0.1~
2wt%, preferably 0.15~1wt%；
Preferably, quaternary ammonium salt phase transfer catalyst is triethyl benzyl ammonia chloride, etamon chloride, tetrabutylammonium bromide, four
One of butyl ammonium chloride, dodecyl trimethyl ammonium chloride, tetradecyl trimethyl ammonium chloride are a variety of, further preferably
For triethyl benzyl ammonia chloride.
Preferably, ionic liquid is benzyl triethylamine tetrafluoroborate, benzyl triethylamine hexafluorophosphate, benzyl triethylamine sulfuric acid
One or more of hydrogen salt, benzyl triethylamine imidazole salts.
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| CN114292183A (en) * | 2021-12-29 | 2022-04-08 | 徐州博康信息化学品有限公司 | Preparation method of photoresist resin monomer containing hydroxyl structure |
| CN114292225A (en) * | 2022-01-10 | 2022-04-08 | 万华化学集团股份有限公司 | Quaternary ammonium type strong-basicity anion exchange resin and method for preparing glycidyl methacrylate through catalysis of quaternary ammonium type strong-basicity anion exchange resin |
| CN114292225B (en) * | 2022-01-10 | 2023-07-11 | 万华化学集团股份有限公司 | Quaternary ammonium type strong-alkalinity anion exchange resin and method for preparing glycidyl methacrylate by catalysis thereof |
| CN115572273A (en) * | 2022-08-30 | 2023-01-06 | 万华化学集团股份有限公司 | Continuous preparation method of glycidyl methacrylate |
| CN115572273B (en) * | 2022-08-30 | 2024-04-09 | 万华化学集团股份有限公司 | Continuous preparation method of glycidyl methacrylate |
| CN117777060A (en) * | 2023-12-26 | 2024-03-29 | 同宇新材料(广东)股份有限公司 | Preparation method of linoleic acid glycidyl ester |
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