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Novel methyl benzoylformate initiator and preparation method thereof

A technology of benzoylformic acid and an initiator, which is applied in the field of reactive benzoylformate initiators and their preparation, can solve the problems of unpleasant production process, high initiation effect, high cost, etc. Good effect, simple operation effect

Inactive Publication Date: 2015-05-13
TIANJIN MOSEN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of this structure in water is low, and the triggering effect is not as high as that of benzoyl formate compounds. The production process is complicated, the amount of waste water is large, and the cost is very high. There are many disadvantages while the advantages are obvious.

Method used

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  • Novel methyl benzoylformate initiator and preparation method thereof
  • Novel methyl benzoylformate initiator and preparation method thereof
  • Novel methyl benzoylformate initiator and preparation method thereof

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preparation example Construction

[0047] 4, a kind of preparation method of novel benzoyl formate initiator (1) as claimed in claim 1, is characterized in that: comprise the following steps:

[0048] (1) Add phase transfer catalyst, substituent phenol and glyoxylic acid into water and methylene chloride in the reaction vessel, stir, and add sodium hydroxide aqueous solution dropwise at a certain temperature. After the dropwise addition, continue to react for a period of time, add water to let The solid is dissolved, the organic phase is separated, the aqueous phase is acidified with acid, and then extracted and washed with ethyl acetate or ether;

[0049]

[0050] ⑵When peroxide or bromine is used as an oxidant to catalyze the oxidation of aromatic hydrocarbons to synthesize aromatic ketones, and esterify with alcohols to form esters

[0051]

[0052] (3) The product of compound (5) reacts with ethylene oxide and propylene oxide to obtain the target product compound (1).

[0053]

[0054]In the step ...

Embodiment 1

[0076] The preparation of 4-hydroxybenzoylformic acid methyl ester, concrete method is as follows:

[0077]

[0078] (1) Put 9.4g of phenol, 6.7g of glyoxylic acid, 50ml of dichloromethane, and 0.9g of tetrabutylammonium bromide into a 100mL four-necked flask under nitrogen protection, and add 24g of 50% sodium hydroxide aqueous solution dropwise under rapid stirring to control The temperature is 0-10°C, HPLC or GC monitors the reaction until the reaction is completed, then cools down to room temperature, extracts the product with ethyl acetate, concentrates under reduced pressure, washes with water 1-3 times, and separates the organic phase;

[0079] (2) Add 8g of 30% hydrogen peroxide dropwise and oxidize at 40°C. Extract with 50ml of toluene to obtain the organic phase;

[0080] (3) 2.5 g of methanol and 1.4 g of p-toluenesulfonic acid were added to the organic phase for esterification at 110° C., desolvated and crystallized to obtain 15.3 g of methyl 4-hydroxybenzoylfo...

Embodiment 2

[0082] The preparation of 4-(2-hydroxyethoxy) methyl benzoylformate, the steps are as follows:

[0083]

[0084] (1) Put 100ml of toluene and 15.3g of methyl 4-hydroxybenzoylformate into a 250mL four-necked flask under the protection of nitrogen, slowly introduce ethylene oxide, stir and heat to 70°C, keep the temperature for about 2 hours, and use The reaction was monitored by thin-layer chromatography or liquid phase. After the reaction was complete, the temperature was lowered to room temperature, and the solvent was removed.

[0085] (2) The residue was diluted with 100ml of dichloromethane, washed with 100ml of water, dried with anhydrous sodium sulfate, desolvated, and purified by distillation under reduced pressure to obtain 17.5g of a colorless oil with a yield of 92.0% and a purity of 99.2%.

[0086] Proton nuclear magnetic resonance spectrum 1HNMR (CDCl3, ppm unit): 8.11 (s, 2H), 7.18 (s, 2H), 4.33 (s, 2H), 3.69 (s, 2H), 3.68 (s, 3H), 3.65 (s , 1H) C NMR spectrum...

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Abstract

The invention discloses a novel methyl benzoylformate initiator and a preparation method thereof. The general formula of the novel methyl benzoylformate initiator is as shown by a compound (1), a compound (2), a compound (3) and a compound (4) in the specification, wherein the substituent group R1 is selected from hydrogen, aryl, C1-C12 linear (branched) alkyls or alkoxys, C3-C12 naphthenic bases, and C4-C12 naphthenic alkyls, R2 is selected from aryl, C1-C12 linear (branched) alkyls, C3-C12 naphthenic bases, and C4-C12 naphthenic alkyls, and the substituent groups R3 and R4 are selected from C1-C12 linear (branched) alkyls. The invention provides a reactive and water-soluble methyl benzoylformate free radical initiator for taking part in photo-polymerization in an olefinic unsaturated compound system, and meanwhile, aims at thoroughly solving the problems of volatilization and migration.

Description

technical field [0001] The invention belongs to the technical field of photoinitiators, in particular to a reactive benzoylformate initiator and a preparation method thereof. The preparation method of this type of compound and the photoinitiator containing this type of compound used in the photopolymerization reaction of ethylenically unsaturated compound system. Background technique [0002] Benzoyl formic ester compounds are free radical photoinitiators with high efficiency and no yellowing, and some compounds have been commercialized, such as methyl benzoyl formate (Darocur MBF) and Irgacure754 of BASF company, and subsequent applicants are in On the basis of the structural modification of benzoyl formate, photoinitiators with new structures (CN1157359A and CN1307207A) have been proposed one after another. [0003] For the first time, Shenzhen Youwei Chemical Technology Co., Ltd. combined the structures of benzoylformic acid ester compounds and α-hydroxyketone compounds ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/28C08G65/332C08G65/38C07C69/738C07C67/08C07C67/31
Inventor 孙建郑康健
Owner TIANJIN MOSEN TECH CO LTD
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