CN101811951A - Preparation method of 2-hydroxyl-1-{4-(2-hydroxyethyl) phenyl}-2-methyl-1-acetone - Google Patents
Preparation method of 2-hydroxyl-1-{4-(2-hydroxyethyl) phenyl}-2-methyl-1-acetone Download PDFInfo
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Abstract
The invention relates to a preparation method of 2-hydroxyl-1-{4-(2-hydroxyethyl) phenyl}-2-methyl-1-acetone, which comprises the following steps that: ethylene glycol phenyl ether acetate serves as the raw material and carries out friedel-crafts reaction with isobutyl chloride with the molar ratio of 1 to 1.2 times of equivalent under the catalysis of lewis acid, the reaction temperature is -5 to 5DEG C, and the reaction time is 3 to 6h; bromination is carried out under the catalysis of N, N-dimethylformamide or iodine; at room temperature, phase transfer catalyst is used for carrying out catalysis and hydrolysis to a brominated product; and finally the product is prepared through purification and crystallization. The preparation method of 2-hydroxyl-1-{4-(2-hydroxyethyl) phenyl}-2-methyl-1-acetone adopts dichloromethane or dichloroethane as the solvent during the bromination process, does not use acetic acid any more, carries out reaction under the catalysis of DMF or I2, so that the reaction time is greatly shortened. The phase transfer catalyst is introduced during the hydrolysis process, so that the intermediate brominated product directly has reaction with alkali in water, thereby preventing using a large amount of ethanol as the solvent, simplifying the process, reducing the production cost and improving the yield.
Description
Technical field
The present invention relates to technical field of organic chemistry, a kind of light trigger 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-synthetic method of 2-methyl isophthalic acid-acetone.
Background technology
2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone is a kind of ultraviolet light polymerization initiator, be that unique FDA certification system allows the available light initiator, can be used for the non-tackiness agent that directly contacts of food in, low smell, low volatilization, low-yellowing has active hydroxyl-oxethyl terminal hydroxy group, can participate in reaction.Can be used for the aqueous photo-curing system, the fusing point height also can be used for the UV cured powder paint.Present Synthetic 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-common method of 2-methyl isophthalic acid-acetone is: Fu-Ke takes place and reacts in ethylene glycol phenyl ether acetate and isobutyryl chloride under lewis acid catalysis, product carries out bromination in the solvent Glacial acetic acid, brominated product boils off and adds etoh solvent behind the solvent Glacial acetic acid and aqueous sodium hydroxide solution is hydrolyzed, and purified crystals obtains product 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone.The main drawback of this technology is that bromination reaction utilizes Glacial acetic acid as solvent, and is big to the corrodibility of equipment, and reaction is carried out slower, needs more than 10 hours.Hydrolytic process will utilize a large amount of ethanol as solvent, and aftertreatment is cumbersome, and cost is higher.
Summary of the invention
Technical problem to be solved by this invention provides a kind of a kind of 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl that can shorten the reaction times, reduce production costs, improve yield]-preparation method of 2-methyl isophthalic acid-acetone.
The present invention adopts following technical proposals to solve its technical problem:
A kind of 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-preparation method of 2-methyl isophthalic acid-acetone, it is characterized in that it is raw material that the first step adopts the ethylene glycol phenyl ether acetate, with mol ratio be that 1～1.2 times of normal isobutyryl chloride carries out Fu-Ke reaction under the catalysis of lewis acid, temperature of reaction is-5 ℃～5 ℃, and the reaction times is 3～6 hours; The reaction of second step is at N, carries out bromination reaction under dinethylformamide or the catalysis of iodine; The 3rd step at room temperature used phase-transfer catalyst to the brominated product catalytic hydrolysis; Carry out purifying crystal at last and make 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-product acetone.
Described lewis acid is aluminum chloride or iron trichloride, and the consumption of lewis acid is 2～2.2 times of isobutyryl chloride.
The catalyzer that described bromination reaction adopts is N, dinethylformamide or I
2, the amount of catalyzer is to add 1% of bromine weight, and temperature of reaction is 20 ℃～25 ℃, and the reaction times is 1～2 hour.
The solvent that described Fu-Ke reaction and bromination reaction adopt is methylene dichloride or ethylene dichloride, and required weight of solvent is three times of starting raw material ethylene glycol phenyl ether acetate.
Described catalytic hydrolysis uses phase-transfer catalyst, and the catalyzed reaction temperature is 20～25, and the reaction times is 1 hour.
Described phase-transfer catalyst is Tetrabutyl amonium bromide or tetrabutyl ammonium sulfate or benzyl triethyl ammonium bromide, and the amount of catalyzer is 1% of a starting raw material ethylene glycol phenyl ether acetate weight.Described phase-transfer catalyst is Tetrabutyl amonium bromide or tetrabutyl ammonium sulfate or benzyl triethyl ammonium bromide.
The solvent of described purification usefulness is an ethyl acetate, and its consumption is 5 times of product theoretical weight, and recrystallization solvent is an ethylene dichloride, and its consumption is 3 times of product theoretical weight.
The present invention utilizes methylene dichloride or ethylene dichloride as solvent in the process of bromination, does not re-use acetic acid, at DMF or I
2React under the catalysis, the time of reaction is shortened greatly, shortened to 1～2 hour by original 10 hours.In addition, in the process of hydrolysis, the present invention introduces phase-transfer catalyst, make the bromo intermediate product in water directly and alkali react, avoid using a large amount of ethanol as solvent, simplified technical process, reduce production costs, improved yield.
Embodiment
2-hydroxyl-1-[4-of the present invention (2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone synthetic, need finish by following three-step reaction.
Intermediate A
Intermediate B
Initiator
The first step be isobutyryl chloride under the catalysis of lewis acid (Lewis acid) with ethylene glycol phenyl ether acetate generation aromatic nucleus on electrophilic substitution reaction (Friedel-Crafts reaction) generation intermediate A, second step by the carbonyl α hydrogen of intermediate A under catalytic condition with bromine generation substitution reaction, generate intermediate B, the 3rd step was that intermediate B is utilized the phase-transfer catalysis hydrolysis in aqueous sodium hydroxide solution, made 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone crude product.The 4th step purified by extraction, underpressure distillation, recrystallization and obtains 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone crystal.
Lewis acid comprises iron trichloride, aluminum chloride etc., preferred aluminum chloride, and its proportioning is 2.0～2.2 times (mol ratios) of ethylene glycol phenyl ether acetate.
Under the catalysis of lewis acid, the temperature of reaction of isobutyryl chloride and ethylene glycol phenyl ether acetate is-5 ℃～5 ℃, and the time of reaction is 3～6 hours.
The catalyzer of bromination reaction is N among the present invention, dinethylformamide (DMF) or I
2, preferred DMF.
The hydrolysis reaction of bromo intermediate B among the present invention, used alkali are 10%～60% aqueous sodium hydroxide solution, and the most frequently used is 32% aqueous sodium hydroxide solution, and sodium hydroxide concentration is 1.5 times of bromination product theoretical amount (mol amount).
The hydrolysis reaction of bromo intermediate B among the present invention, used phase-transfer catalyst are Tetrabutyl amonium bromide or tetrabutyl ammonium sulfate or benzyl triethyl ammonium bromide, preferred Tetrabutyl amonium bromide (TBBA).
Embodiment 1
1, Fu-Ke reaction
53.4g (0.4mol) aluminum trichloride (anhydrous) is dissolved in the 108g ethylene dichloride, under-5 ℃, begins to drip ethylene glycol phenyl ether acetate 36g (0.2mol), in 0.5 hour, add.Then, drip isobutyryl chloride 21.3g (0.2mol) down at-5 ℃, added at 1 hour, restir reaction 6 hours, controlled temperature be at-5 ℃～0 ℃, reaction mixture is poured in the mixture of 20ml hydrochloric acid and 450g frozen water in cancellation, tell organic phase, with 20% hydrochloric acid 80mL washing 2 times, drying gets intermediate A.
2, bromination reaction
In A, add DMF 0.32g, (is amount that adds bromine in what ratio grasped at 20 ℃ of beginning dripping bromine 32g (0.2mol)?), keep temperature not to be higher than 25 ℃, added in 2 hours.Insulation reaction is 1 hour then, 25 ℃ of temperature.2 times (is problem the same, unqualified in the specification sheets, do not say that others knows that this program and raw material and consumption are arranged in water 60ml washing with saturated sodium sulfite solution cancellation?), steaming desolventizes, and gets thickness oily matter.
3, catalytic hydrolysis
In the oily product of previous step, add 36g water) and the mixing solutions of 0.36g phase-transfer catalyst Tetrabutyl amonium bromide, is (amount of hydro-oxidation sodium solution in what ratio grasped in the sodium hydroxide solution (sodium hydroxide concentration is 1.5 times of theoretical amount 0.4mol) that adds 75g32% below 20 ℃ again?), then under 20 ℃, react after 1 hour, be neutralized to neutrality with 37% hydrochloric acid
4, purifying crystal
Use the 225g ethyl acetate extraction, boil off ethyl acetate after washing, the drying; Add ethylene dichloride 135g, the heating activated carbon decolorizing, filtered while hot is removed gac and granule foreign, decrease temperature crystalline, the crystal filtering drying is got product 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl again]-2-methyl isophthalic acid-acetone 31.4g, the yield of the finished product is 70.2%, content 98.5%.
Embodiment 2
1, Fu-Ke reaction
58.7g (0.44mol) aluminum trichloride (anhydrous) is dissolved in the 108g methylene dichloride, begins to drip ethylene glycol phenyl ether acetate 36g (0.2mol), in 0.5 hour, add at 0 ℃.Then, drip isobutyryl chloride 25.6g (0.24mol) down at 0 ℃, added at 1 hour, restir reaction 3 hours, controlled temperature is poured reaction mixture in 20ml hydrochloric acid and 450g frozen water cancellation about 0 ℃～5 ℃, tell organic phase, with 20% hydrochloric acid 80mL washing 2 times, drying gets intermediate A.
2, bromination reaction
In A, add I
20.32g, begin to drip Br at 20 ℃
232g (0.2mol) keeps temperature not to be higher than 25 ℃, adds in 2 hours.Insulation reaction is 2 hours then, 20 ℃ of temperature.With the cancellation of 60g (20%) sodium sulfite solution, water 60ml washing 2 times, steaming desolventizes, and gets thickness oily matter.
3, catalytic hydrolysis
In the oily product of previous step, add 36g water and 0.36g tetrabutyl ammonium sulfate,, be neutralized to neutrality with 37% hydrochloric acid in reaction under 25 ℃ after 1 hour then again in adding 75g (32%) sodium hydroxide solution below 20 ℃.
4, purifying crystal
Use the 225g ethyl acetate extraction, boil off ethyl acetate after washing, the drying, add ethylene dichloride 135g, the heating activated carbon decolorizing, filtered while hot is removed gac and granule foreign, decrease temperature crystalline, filtration, dry product 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone 29.0g, the finished product yield is 64.8%, content 98.7%.
Embodiment 3
1, Fu-Ke reaction
53.4g (0.40mol) aluminum trichloride (anhydrous) is dissolved in the 108g ethylene dichloride, begins to drip ethylene glycol phenyl ether acetate 36g (0.2mol), in 0.5 hour, add at-5 ℃.Then, drip isobutyryl chloride 21.3g (0.20mol) down at-5 ℃, about 1 hour, add, restir reaction 6 hours, controlled temperature is poured reaction mixture in 20ml hydrochloric acid and 450g frozen water cancellation at-5 ℃～0 ℃, tell organic phase, with 20% hydrochloric acid 80mL washing 2 times, drying gets intermediate A.
2, bromination reaction
In A, add DMF 0.32g, about 20 ℃, begin to drip Br
232g (0.2mol) keeps temperature not to be higher than 25 ℃, adds in 2 hours.Insulation reaction is 1 hour then, 25 ℃ of temperature.With the cancellation of 60g (20%) sodium sulfite solution, water 60ml washing 2 times, steaming desolventizes, and gets thickness oily matter.
3, catalytic hydrolysis
In the oily product of previous step, add 36g water and 0.36g benzyl triethyl ammonium bromide,, be neutralized to neutrality with 37% hydrochloric acid in reaction under 20 ℃ after 1 hour then again in adding 75g (32%) sodium hydroxide solution below 20 ℃.
4, purifying crystal
Use the 225g ethyl acetate extraction, boil off ethyl acetate after washing, the drying, add ethylene dichloride 135g, the heating activated carbon decolorizing, filtered while hot is removed gac and solid impurity, decrease temperature crystalline, filtration, dry product 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone 30.0g, the finished product yield is 66.8%, content 98.2%.
Claims (6)
1. a 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-preparation method of 2-methyl isophthalic acid-acetone, it is characterized in that it is raw material that the first step adopts the ethylene glycol phenyl ether acetate, with mol ratio be that 1～1.2 times of normal isobutyryl chloride carries out Fu-Ke reaction under the catalysis of lewis acid, temperature of reaction is-5 ℃～5 ℃, and the reaction times is 3～6 hours; The reaction of second step is at N, carries out bromination reaction under dinethylformamide or the catalysis of iodine; The 3rd step at room temperature used phase-transfer catalyst to the brominated product catalytic hydrolysis; Carry out purifying crystal at last and make 2-hydroxyl-1-[4-(2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-product acetone.
2. 2-hydroxyl-1-[4-according to claim 1 (2-hydroxy ethoxy) phenyl]-preparation method of 2-methyl isophthalic acid-acetone, it is characterized in that described lewis acid is an aluminum chloride, the consumption of lewis acid is 2.0～2.2 times of mol ratios of ethylene glycol phenyl ether acetate.
3. 2-hydroxyl-1-[4-according to claim 1 (2-hydroxy ethoxy) phenyl]-preparation method of 2-methyl isophthalic acid-acetone, the molar weight that it is characterized in that the used bromine of described bromination reaction equates with the reactant molar weight, the catalyzer that bromination adopts is N, dinethylformamide or I
2, the amount of catalyzer is to add 1% of bromine weight, and temperature of reaction is 20 ℃～25 ℃, and the reaction times is 1～2 hour.
4. 2-hydroxyl-1-[4-according to claim 1 (2-hydroxy ethoxy) phenyl]-preparation method of 2-methyl isophthalic acid-acetone, it is characterized in that the solvent that described Fu-Ke reaction and bromination reaction process adopt is methylene dichloride or ethylene dichloride, the mol ratio of required weight of solvent is 3 times of starting raw material ethylene glycol phenyl ether acetate.
5. 2-hydroxyl-1-[4-according to claim 1 (2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone preparation method, it is characterized in that described catalytic hydrolysis uses phase-transfer catalyst, the catalyzed reaction temperature is 20 ℃～25 ℃, the reaction times is 1 hour.
6. 2-hydroxyl-1-[4-according to claim 1 (2-hydroxy ethoxy) phenyl]-2-methyl isophthalic acid-acetone preparation method, it is characterized in that described phase-transfer catalyst is Tetrabutyl amonium bromide or tetrabutyl ammonium sulfate or benzyl triethyl ammonium bromide, the amount of catalyzer is 1% of a starting raw material ethylene glycol phenyl ether acetate weight.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786405A (en) * | 2012-08-29 | 2012-11-21 | 天津久日化学股份有限公司 | Preparation method for 2-hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone |
| CN103987739A (en) * | 2011-12-16 | 2014-08-13 | 阿克伦大学 | Substituted phenacyl molecules and photoresponsive polymers |
| WO2015045857A1 (en) * | 2013-09-30 | 2015-04-02 | 富士フイルム株式会社 | METHOD FOR PRODUCING α-HALOGENOACETOPHENON COMPOUND, AND α-BROMOACETOPHENON COMPOUND |
| CN106255676A (en) * | 2014-05-15 | 2016-12-21 | 富士胶片株式会社 | The manufacture method of α bromoacetophenone compound |
| CN106365967A (en) * | 2016-08-16 | 2017-02-01 | 甘肃金盾化工有限责任公司 | Preparation method for 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-acetone |
| CN112723999A (en) * | 2020-12-31 | 2021-04-30 | 湖北英纳氏生物科技有限公司 | Synthetic method of 2- (4-ethoxyphenyl) -2-methylpropanol |
| CN114292172A (en) * | 2021-12-29 | 2022-04-08 | 天津久日新材料股份有限公司 | Preparation method of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-acetone |
| CN114315575A (en) * | 2021-12-29 | 2022-04-12 | 湖南久日新材料有限公司 | Preparation method and application of photoinitiator intermediate |
| CN114315544A (en) * | 2021-12-29 | 2022-04-12 | 天津久日新材料股份有限公司 | Preparation method of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-acetone |
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| CN103987739A (en) * | 2011-12-16 | 2014-08-13 | 阿克伦大学 | Substituted phenacyl molecules and photoresponsive polymers |
| CN103987739B (en) * | 2011-12-16 | 2017-04-05 | 阿克伦大学 | The phenacyl molecule being substituted and optical Response polymer |
| CN102786405A (en) * | 2012-08-29 | 2012-11-21 | 天津久日化学股份有限公司 | Preparation method for 2-hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone |
| JPWO2015045857A1 (en) * | 2013-09-30 | 2017-03-09 | 富士フイルム株式会社 | Method for producing α-halogenoacetophenone compound and α-bromoacetophenone compound |
| US9682911B2 (en) | 2013-09-30 | 2017-06-20 | Fujifilm Corporation | Method for producing α-halogenoacetophenon compound, and α-bromoacetophenon compound |
| CN105593200B (en) * | 2013-09-30 | 2018-01-02 | 富士胶片株式会社 | The manufacture method and α bromoacetophenone compounds of α halo acetophenone compounds |
| EP3053908A4 (en) * | 2013-09-30 | 2016-10-12 | Fujifilm Corp | METHOD FOR PRODUCING alpha-HALOGENOACETOPHENON COMPOUND, AND alpha-BROMOACETOPHENON COMPOUND |
| JP6089110B2 (en) * | 2013-09-30 | 2017-03-01 | 富士フイルム株式会社 | Method for producing α-halogenoacetophenone compound and α-bromoacetophenone compound |
| CN105593200A (en) * | 2013-09-30 | 2016-05-18 | 富士胶片株式会社 | Method for producing [alpha]-halogenoacetophenon compound, and [alpha]-bromoacetophenon compound |
| WO2015045857A1 (en) * | 2013-09-30 | 2015-04-02 | 富士フイルム株式会社 | METHOD FOR PRODUCING α-HALOGENOACETOPHENON COMPOUND, AND α-BROMOACETOPHENON COMPOUND |
| CN106255676A (en) * | 2014-05-15 | 2016-12-21 | 富士胶片株式会社 | The manufacture method of α bromoacetophenone compound |
| CN106255676B (en) * | 2014-05-15 | 2019-04-30 | 富士胶片株式会社 | The manufacturing method of alpha-brominated acetophenone compound |
| CN106365967A (en) * | 2016-08-16 | 2017-02-01 | 甘肃金盾化工有限责任公司 | Preparation method for 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-acetone |
| CN112723999A (en) * | 2020-12-31 | 2021-04-30 | 湖北英纳氏生物科技有限公司 | Synthetic method of 2- (4-ethoxyphenyl) -2-methylpropanol |
| CN114292172A (en) * | 2021-12-29 | 2022-04-08 | 天津久日新材料股份有限公司 | Preparation method of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-acetone |
| CN114315575A (en) * | 2021-12-29 | 2022-04-12 | 湖南久日新材料有限公司 | Preparation method and application of photoinitiator intermediate |
| CN114315544A (en) * | 2021-12-29 | 2022-04-12 | 天津久日新材料股份有限公司 | Preparation method of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-acetone |
| CN114292172B (en) * | 2021-12-29 | 2023-12-29 | 天津久日新材料股份有限公司 | Preparation method of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-acetone |
| CN114315544B (en) * | 2021-12-29 | 2023-12-29 | 天津久日新材料股份有限公司 | Preparation method of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-acetone |
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Application publication date: 20100825 |