CN106365967A - Preparation method for 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-acetone - Google Patents
Preparation method for 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-acetone Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
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Abstract
The invention provides a preparation method for a hydroxy-ketone photoinitiator, i.e., 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-acetone. In tradition production processes, chlorine or liquid bromine is used as a halogenation reagent, and halogenation and hydrolysis are successively carried out so as to obtain a target product; however, chlorine is severely poisonous gas prone to leakage while liquid bromine is easily volatile liquid with strong toxicity and corrosivity and produces a great amount of acidic exhaust gas in the process of halogenation, which leads to production of a great amount of waste water in the process of aftertreatment. The preparation method provided by the invention avoids usage of chlorine or liquid bromine as the halogenation reagent and directly prepares the target product in one step by using a carbon tetrachloride process. The preparation method provided by the invention has the advantages that the amount of exhaust gas produced in the process of reaction is small; feeding and aftertreatment are simple to operate; the output of wastewater is low; product content reaches 99% or above; and production cost is low.
Description
Technical field
The present invention relates to technical field of organic chemistry is and in particular to the 2- hydroxyl -1- [4- of one kind-alcohol ketone photoinitiator
(2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone preparation method.
Technical background
- alcohol ketone photoinitiator 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone is unique fda
Authentication system allows available light trigger.It can be used for the adhesive of food non-direct-contact in, there is low abnormal smells from the patient, low wave
Send out, the characteristic such as low-yellowing；Can also be used for aqueous photo-curing system；Also can be used for uv cured powder paint.At present-hydroxy-ketone light
The main production of initiator 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone is with ethylene glycol phenyl ether vinegar
Acid esters is initiation material, through being acylated, halogenation, and hydrolysis obtains crude product, and final refining obtains qualified products.This production technology operates
Step is long, and the halide reagent bromine used belongs to the volatile strong liquid poisoned with severe corrosive, brings greatly to operative
Inconvenience, and have substantial amounts of acid waste gas to produce, a large amount of waste water can be produced in post processing again, environment is produced with a large amount of harm.
With the increase of the p- alcohol ketone photoinitiator in market 2959 consumption, old production technology can not meet the market demand and ring
Guaranteed request, so one environmental protection of exploitation-alcohol ketone photoinitiator 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2-
The preparation method of methyl isophthalic acid-acetone is imperative.
Content of the invention
The technical problem to be solved be the deficiencies in the prior art are provided a kind of operating procedure advantages of simple,
Low cost, safety and environmental protection, more can be suitably used for industrialized-alcohol ketone photoinitiator 2- hydroxyl -1- [4- (2- hydroxy ethoxy) benzene
Base] -2- methyl isophthalic acid-acetone preparation method.
Technical problem for solving the present invention adopts the following technical scheme that
A kind of preparation method of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone, its step is as follows:
(1) preparation of intermediate a: it is raw material using ethylene glycol phenyl ether acetate, respectively Deca in the solvent adding catalyst
Ethylene glycol phenyl ether acetate and isobutyryl chloride, the mass ratio of catalyst and solvent is 1:2, temperature control at -10 DEG C -0 DEG C, second
The mol ratio of glycol phenylate acetate and isobutyryl chloride is 1:1.1-1.3, wherein ethylene glycol phenyl ether acetate and solvent quality ratio
For 1:3.0, after dripping off, control -3 DEG C -0 DEG C reaction 3h-6h of temperature, afterwards reactant liquor 3.0-6.0h is slowly added dropwise into frozen water
In, after dripping off, stirring 10 minutes, static 10 minutes, separate organic faciess, organic faciess be washed once with 5% sodium bicarbonate solution,
Static separate organic faciess, organic faciess are concentrated to dryness in vacuum 0.08mpa, temperature 70 C, both a；
(2) preparation of crude product c: under catalyst, upper step gained a is mixed with carbon tetrachloride, room temperature drops to mass fraction and is
In the sodium hydroxide solution of 32%-50%, 30 DEG C -70 DEG C of controlling reaction temperature, after reaction 16h-24h, Deca concentrated hydrochloric acid adjusts ph
To neutral, add methyl acetate to be extracted twice, merge organic faciess and be concentrated to dryness, backward debris in add its quality twice
1,2- dichloroethanes, stirring is cooled between -5 DEG C -0 DEG C crystallization, and after keeping this temperature 2h, filter both c；
(3) product purification: crude product c is added in 1, the 2- dichloroethanes of its quality twice, stirring is warming up to 50 DEG C -55 DEG C, plus
Enter the activated carbon decolorizing 1 hour of crude product c mass 10%, filter afterwards, filtrate is lowered the temperature crystallize, filter both final product 2- hydroxyl -1-
[4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone.
In described step (1), catalyst is aluminum chloride or ferric chloride.
In described step (1), solvent is dichloromethane or 1,2- dichloroethanes or 1,2- dichloropropane.
In described step (1), ethylene glycol phenyl ether acetate and isobutyryl chloride are first Deca isobutyl toward the order of Deca in solvent
Acyl chlorides, rear Deca ethylene glycol phenyl ether acetate.
In described step (2), a and carbon tetrachloride mol ratio are 1:1.1-1.8.
In described step (2), a and solid sodium hydroxide mol ratio are 1:3-8.
In described step (2), catalyst is dimethylformamide dmf or dimethyl acetylamide dmac, and catalyst quality is a
The 15%-50% of weight.
In described step (2), extractant is methyl acetate or ethyl acetate.
In described step (3), activated carbon is injection 767 activated carbon.
- 10 DEG C -5 DEG C of crystallization temperature in described step (3).
The having of the present invention-alcohol ketone photoinitiator 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone
Machine synthesis chemical equation is:
The first step:
Second step:
The existing production technology of the present invention is compared, and it avoids with chlorine or bromine as halide reagent in traditional processing technology, first warp
Cross halogenation, after obtain target product through hydrolysis, the chlorine used in traditional handicraft belongs to severe toxicity and easily reveals gas, and bromine belongs to
In volatile there is extremely strong strong toxic and corrosive liquid, and its halogenation during can produce substantial amounts of spent acidic
Gas, last handling process can produce substantial amounts of waste water.And the present invention obtains target product using the direct step of carbon tetrachloride method, it is excellent
Point is: is easy to get in terms of raw material, toxic is low；In course of reaction, exhaust gas production is few；And feed intake and post-processing operation
Simply；Waste water quantum of output is few；The product content obtaining can reach more than 99%；Low production cost, more suitable for commercial production.
Specific embodiment
The life of the present invention-alcohol ketone photoinitiator 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone
Production. art needs two-step reaction to carry out obtaining crude product altogether, then is recrystallized to give finished product through a step, and specific embodiment is provided below
The present invention will be further elaborated, but embodiment does not limit the scope of the invention.
Implement row 1
A kind of preparation method of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone, its step is as follows:
(1) preparation of a
In the tetra- mouthfuls of reaction bulbs of 2l being totally dried, put into dichloroethanes 900g, stirring adds aluminum chloride 450g, be cooled to-
10 DEG C, it is slowly added dropwise isobutyryl chloride 195 g(1.83mol), drip off rear -10 DEG C of reaction 30min of keeping temperature, be slowly added dropwise second two
Alcohol phenylate acetate 300 g(1.66 mol) drip complete -10 DEG C of reaction 6h of keeping temperature, afterwards reactant liquor 3h is slowly added dropwise into ice
In water, after stirring 10 minutes, stratification, lower floor's organic faciess be washed once with 5% sodium bicarbonate solution, after stirring 10 minutes,
Stratification, lower floor's organic faciess are concentrated in vacuo, recovery after the process of effluent dichloroethanes, and debris are intermediate a, weight
It is about 408 g, content 98%, molar yield 98%.
(2) preparation of crude product c
In clean tetra- mouthfuls of reaction bulbs of 3l, add water 400 g, stirring puts into sodium hydroxide 400 g(10mol), treat hydroxide
After sodium is completely dissolved, that is, mass fraction is 50% sodium hydroxide solution, 30 DEG C of controlling reaction temperature, Deca a:408 g at a slow speed
(1.63mol)/carbon tetrachloride: 276 g(1.63mol)/dmac:61 g mixed liquor, after dripping off, 30 DEG C of controlling reaction temperature is anti-
Answer 24h, reaction end concentrated hydrochloric acid adjusts reactant liquor ph to neutral, adds the methyl acetate of 1.4l afterwards, stir 10 minutes,
Cross the side product chlorinated sodium filtering off in feed liquid, filtrate static layering, the methyl acetate that lower floor's aqueous phase adds 1l extracts once, it
Merge organic faciess afterwards, normal pressure reclaims methyl acetate with recovery, when methyl acetate discharge is smaller, is changed to vacuum dense
Contracting, control temperature 70 C, vacuum 0.08mpa, concentrate half an hour after, backward debris in add the 1,2- of its quality twice
Dichloroethanes, stirring is cooled to 0 DEG C of crystallize, and after keeping this temperature 2h, filters to obtain crude product a weight in wet base 395 g, dries 315 g,
Content is more than 97%, and molar yield is about 85%.
(3) crude product c must refine
Add 630g dichloroethanes in clean tri- mouthfuls of reaction bulbs of 1l, stirring adds crude product c315 g, is warming up to 55 DEG C afterwards,
After crude product thoroughly dissolves, add activated carbon 31.5 g, stirring decolouring 1 hour, filter afterwards, and washed with 50 g dichloroethanes tops
Filter cake, last merging filtrate and washing liquid proceed in tri- mouthfuls of reaction bulbs of clean 1l, and stirring is cooled to 5 DEG C of crystallizes, filters to obtain finished product
Dry weight 280 g, content is more than 99%.
Implement row 2
A kind of preparation method of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone, its step is as follows:
(1) preparation of a
In the tetra- mouthfuls of reaction bulbs of 2l being totally dried, put into dichloromethane 900 g, stirring adds ferric chloride 450 g, is cooled to
0 DEG C, it is slowly added dropwise isobutyryl chloride 195 g(1.83mol), drip off rear 0 DEG C of reaction 30min of keeping temperature, be slowly added dropwise ethylene glycol
Phenylate acetate 300 g(1.66mol) drip complete 0 DEG C of reaction 3h of keeping temperature, afterwards reactant liquor 6h is slowly added dropwise in frozen water,
After stirring 10 minutes, stratification, lower floor's organic faciess be washed once with 5% sodium bicarbonate solution, after stirring 10 minutes, standing
Layering, lower floor's organic faciess are concentrated in vacuo, effluent dichloroethanes process after recovery, debris are intermediate a, again for
395 g, content 93%, molar yield 95%.
(2) preparation of crude product c
In clean tetra- mouthfuls of reaction bulbs of 3l, add water 850 g, stirring puts into solid piece alkali 400 g(10 mol), treat that piece alkali is complete
After CL, 70 DEG C of controlling reaction temperature, Deca a:395 g(1.58mol at a slow speed)/carbon tetrachloride: 438 g(2.84 mol)/
The mixed liquor of dmac:197 g, after dripping off, 70 DEG C of reaction 16h of controlling reaction temperature, reaction end concentrated hydrochloric acid adjusts reactant liquor
Ph, to neutral, adds the methyl acetate of 1.4l afterwards, stirs 10 minutes, crosses the side product chlorinated sodium filtering off in feed liquid, and filtrate is quiet
Only it is layered, the methyl acetate that lower floor's aqueous phase adds 1l extracts once, merges organic faciess afterwards, normal pressure reclaims methyl acetate to return
Receipts are applied mechanically, and when methyl acetate discharge is smaller, are changed to concentrated in vacuo, control temperature 70 C, vacuum 0.08mpa, concentrate
After half an hour, backward debris in add 1, the 2- dichloroethanes of its quality twice, stirring is cooled to -5 DEG C of crystallizes, filters
Crude product a weight in wet base 370 g, 288 g after drying, content 92%, molar yield is 81%.
(3) crude product c must refine
Add 576 g dichloroethanes in clean tri- mouthfuls of reaction bulbs of 1l, stirring adds crude product c288 g, is warming up to 50 afterwards
DEG C, after crude product thoroughly dissolves, add activated carbon 28.8 g, stirring decolouring 1 hour, filter afterwards, and with 50 g dichloroethanes
Top filter wash cake, last merging filtrate and washing liquid proceed in tri- mouthfuls of reaction bulbs of clean 1l, and stirring is cooled to -10 DEG C of crystallizes, filter
Obtain finished product dry weight 260 g, content is 95%.
Implement row 3
A kind of preparation method of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone, its step is as follows:
(1) preparation of a
In the tetra- mouthfuls of reaction bulbs of 2l being totally dried, put into dichloroethanes 900 g, stirring adds aluminum chloride 450g, be cooled to-
5 DEG C, it is slowly added dropwise ethylene glycol phenyl ether acetate 300 g(1.66mol), drip off -5 DEG C of reaction half an hour of rear keeping temperature, afterwards
It is slowly added dropwise isobutyryl chloride 195 g(1.83mol) drip complete -5 DEG C of reaction 3h of keeping temperature, afterwards reactant liquor is slowly added dropwise into ice
In water, after stirring 10 minutes, stratification, lower floor's organic faciess be washed once with 5% sodium bicarbonate solution, after stirring 10 minutes,
Stratification, lower floor's organic faciess are concentrated in vacuo, recovery after the process of effluent dichloroethanes, and debris are intermediate a, weight
About 400 g, content 98%, molar yield 96%.
(2) preparation of crude product c
In clean tetra- mouthfuls of reaction bulbs of 3l, add drinking water 600 g, stirring puts into solid piece alkali 400 g(10mol), treat piece
After alkali is completely dissolved, 35 DEG C of controlling reaction temperature, Deca a:400 g(1.6mol at a slow speed)/carbon tetrachloride: 370g(2.4mol)/
The mixed liquor of dmac:80 g, after dripping off, 65 DEG C of reaction 4h of controlling reaction temperature, reaction end adjusts reactant liquor ph with concentrated hydrochloric acid
To neutrality, add the ethyl acetate of 1.4l afterwards, stir 10 minutes, cross the side product chlorinated sodium filtering off in feed liquid, filtrate is static
Layering, lower floor's aqueous phase adds the ethyl acetate extraction of 1l once, merges organic faciess afterwards, concentrated in vacuo, concentration terminates, to residual
Stay in liquid plus dichloroethanes 800ml, stirring is cooled to -5 DEG C of crystallizes, filters to obtain crude product a weight in wet base 400 g, 300 g after drying, contains
Amount 96%, molar yield is 83%.
(3) crude product c must refine
Add 600 g dichloroethanes in clean tri- mouthfuls of reaction bulbs of 1l, stirring adds crude product c300 g, is warming up to 55 afterwards
DEG C, after crude product thoroughly dissolves, add activated carbon 30 g, stirring decolouring half an hour, filter afterwards, and with 50 g dichloroethanes tops
Filter wash cake, last merging filtrate and washing liquid proceed in tri- mouthfuls of reaction bulbs of clean 1l, and stirring is cooled to -5 DEG C of crystallizes, filters
Product dry weight 268 g, content is 98%.
Implement row 4
A kind of preparation method of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone, its step is as follows:
(1) preparation of a
In the tetra- mouthfuls of reaction bulbs of 2l being totally dried, put into dichloroethanes 900 g, stirring adds ferric chloride 450 g, cooling
To -10 DEG C, it is slowly added dropwise isobutyryl chloride 195 g(1.83mol), drip off -10 DEG C of reaction half an hour of rear keeping temperature, afterwards slowly
Deca ethylene glycol phenyl ether acetate 300 g(1.66mol) drip complete -10 DEG C of reaction 3h of keeping temperature, afterwards reactant liquor is slowly dripped
Add in frozen water, after stirring 10 minutes, stratification, lower floor's organic faciess be washed once with 5% sodium bicarbonate solution, stirs 10
After minute, stratification, lower floor's organic faciess are concentrated in vacuo, and recovery after the process of effluent dichloroethanes, during debris are
Mesosome a, again for 408 g, content 98%, molar yield 98%.
(2) preparation of crude product c
In clean tetra- mouthfuls of reaction bulbs of 3l, add drinking water 400 g, stirring puts into solid piece alkali 400 g(10mol), treat piece
After alkali is completely dissolved, 35 DEG C of controlling reaction temperature, Deca a:408 g(1.63mol at a slow speed)/carbon tetrachloride: 377 g
(2.45mol) mixed liquor of/dmf:90 g, after dripping off, 35 DEG C of reaction 16h of controlling reaction temperature, reaction end concentrated hydrochloric acid is adjusted
Save reactant liquor ph to neutral, add the methyl acetate of 1.4l afterwards, stir 10 minutes, cross side product chlorinated in elimination feed liquid
Sodium, filtrate static layering, the methyl acetate that lower floor's aqueous phase adds 1l extracts once, merges organic faciess afterwards, concentrated in vacuo, dense
It is reduced to after doing, adds dichloroethanes 800ml in debris, stirring is cooled to 0 DEG C of crystallize, filters to obtain crude product a weight in wet base 380 g, dries
280 g after dry, content 97%, molar yield is 76.7%.
(3) crude product c must refine
Add 560 g dichloroethanes in clean tri- mouthfuls of reaction bulbs of 1l, stirring adds crude product c280g, is warming up to 55 DEG C afterwards,
After crude product thoroughly dissolves, add activated carbon 28g, stirring decolouring half an hour, filter afterwards, and with 50g dichloroethanes top filter wash
Cake, last merging filtrate and washing liquid proceed in tri- mouthfuls of reaction bulbs of clean 1l, stirring be cooled to -5 DEG C of crystallizes, filter finished product do
Weight 260g, content is 98.5%.
Claims (10)
1. a kind of preparation method of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone is it is characterised in that walk
Suddenly as follows:
(1) preparation of intermediate a: it is raw material using ethylene glycol phenyl ether acetate, respectively Deca in the solvent adding catalyst
Ethylene glycol phenyl ether acetate and isobutyryl chloride, the mass ratio of catalyst and solvent is 1:2, temperature control at -10 DEG C -0 DEG C, second two
The mol ratio of alcohol phenylate acetate and isobutyryl chloride is 1:1.1-1.3, and wherein ethylene glycol phenyl ether acetate and solvent quality ratio is
1:3.0, after dripping off, controls -3 DEG C -0 DEG C reaction 3h-6h of temperature, afterwards reactant liquor 3 h-6h is slowly added dropwise in frozen water, drips
After complete, stirring 10 minutes, static 10 minutes, separate organic faciess, organic faciess be washed once with 5% sodium bicarbonate solution, static
Separate organic faciess, organic faciess are concentrated to dryness in vacuum 0.08mpa, temperature 70 C, both obtain a；
(2) preparation of crude product c: under catalyst, upper step gained a is mixed with carbon tetrachloride, room temperature drops to mass fraction and is
In the sodium hydroxide solution of 32%-50%, 30 DEG C -70 DEG C of controlling reaction temperature, after reaction 16h-24h, Deca concentrated hydrochloric acid adjusts ph
To neutral, add methyl acetate to be extracted twice, merge organic faciess and be concentrated to dryness, backward debris in add its quality twice
1,2- dichloroethanes, stirring is cooled between -5 DEG C -0 DEG C crystallization, and after keeping this temperature 2h, filter both c；
(3) product purification: crude product c is added in 1, the 2- dichloroethanes of its quality twice, stirring is warming up to 50 DEG C -55 DEG C, plus
Enter the activated carbon decolorizing 1 hour of crude product c mass 10%, filter afterwards, filtrate is lowered the temperature crystallize, filter both final product 2- hydroxyl -1-
[4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone.
2. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (1) catalyst be aluminum chloride or ferric chloride.
3. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (1) solvent be dichloromethane or 1,2- dichloroethanes or 1,2- dichloropropane.
4. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (1), ethylene glycol phenyl ether acetate and isobutyryl chloride are first to drip toward the order of Deca in solvent
Plus isobutyryl chloride, rear Deca ethylene glycol phenyl ether acetate.
5. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (2), a and carbon tetrachloride mol ratio are 1:1.1-1.8.
6. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (2), a and solid sodium hydroxide mol ratio are 1:3-8.
7. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (2) catalyst be dimethylformamide dmf or dimethyl acetylamide dmac, catalyst matter
Measure the 15%-50% for a weight.
8. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (2) extractant be methyl acetate or ethyl acetate.
9. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: in described step (3) activated carbon be injection 767 activated carbon.
10. the preparation side of 2- hydroxyl -1- [4- (2- hydroxy ethoxy) phenyl] -2- methyl isophthalic acid-acetone according to claim 1
Method it is characterised in that: -10 DEG C -5 DEG C of crystallization temperature in described step (3).
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116265427A (en) * | 2021-12-16 | 2023-06-20 | 爱生华(苏州)光学有限公司 | Treatment method of 2- (4-benzoyl-3-hydroxyphenoxy) ethyl 2-acrylate kettle residues |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861916A (en) * | 1985-04-03 | 1989-08-29 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Photoinitiators for photopolymerization of unsaturated systems |
| US4922004A (en) * | 1985-09-28 | 1990-05-01 | Merck Patent Gesellschaft mit bescrankter Haftung | Copolymerizable photoinitiators |
| CN101811951A (en) * | 2010-05-07 | 2010-08-25 | 甘肃金盾化工有限责任公司 | Preparation method of 2-hydroxyl-1-{4-(2-hydroxyethyl) phenyl}-2-methyl-1-acetone |
| CN102603509A (en) * | 2011-12-20 | 2012-07-25 | 常州大学 | Preparation method of bifunctional phenylindane photoinitiator |
-
2016
- 2016-08-16 CN CN201610672820.4A patent/CN106365967A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861916A (en) * | 1985-04-03 | 1989-08-29 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Photoinitiators for photopolymerization of unsaturated systems |
| US4922004A (en) * | 1985-09-28 | 1990-05-01 | Merck Patent Gesellschaft mit bescrankter Haftung | Copolymerizable photoinitiators |
| CN101811951A (en) * | 2010-05-07 | 2010-08-25 | 甘肃金盾化工有限责任公司 | Preparation method of 2-hydroxyl-1-{4-(2-hydroxyethyl) phenyl}-2-methyl-1-acetone |
| CN102603509A (en) * | 2011-12-20 | 2012-07-25 | 常州大学 | Preparation method of bifunctional phenylindane photoinitiator |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116265427A (en) * | 2021-12-16 | 2023-06-20 | 爱生华(苏州)光学有限公司 | Treatment method of 2- (4-benzoyl-3-hydroxyphenoxy) ethyl 2-acrylate kettle residues |
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