CN1958549B - Method for preparing tertiary butyl 4' methoxy dibenzoyl methane - Google Patents
Method for preparing tertiary butyl 4' methoxy dibenzoyl methane Download PDFInfo
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- CN1958549B CN1958549B CN2006101185392A CN200610118539A CN1958549B CN 1958549 B CN1958549 B CN 1958549B CN 2006101185392 A CN2006101185392 A CN 2006101185392A CN 200610118539 A CN200610118539 A CN 200610118539A CN 1958549 B CN1958549 B CN 1958549B
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- dibenzoyl methane
- methoxy dibenzoyl
- tertiary butyl
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Abstract
This invention relates to a method for preparing 4-tert-butyl-4'-methoxy dibenzoyl methane. The method comprises: condensing 4-tert-butyl methyl benzoate and 4-methoxyl acetophenone in the presence of alkaline catalyst and corresponding solvent to obtain 4-tert-butyl-4'-methoxy dibenzoyl methane crude product, and decoloring and refining to obtain 4-tert-butyl-4'-methoxy dibenzoyl methane product. The method utilizes specific alkaline catalyst and solvent, thus has such advantages as little pollution, light color, little odor, high quality and high yield.
Description
Affiliated technical field
The present invention relates to the preparation method of a kind of 4-tertiary butyl-4 '-methoxy dibenzoyl methane, belong to the fine chemical technology field.
Background technology
The meticulous organic products of the 4-tertiary butyl-4 '-methoxy dibenzoyl methane.It is that the novel diphenylpropane-1,3-dione(DPPO) class long wave ultraviolet UVA of 1980s exploitation is (the most representative a kind of in the absorption agent of 320nm～400nm).It can present the tautomerism characteristic of keto-acid/enol form, causes it to have the UV resistant performance of " innately ".The λ max of its keto-acid isomer is about 260nm, the λ max of enol form isomer is about 350nm, just in time be positioned at the UVA wave band, can absorb high energy ultraviolet (UV) A in both tautomeric processes, it is a kind of in only in the world at present a few UVA absorption agent.It can effectively be blocked, and UVA forms the destruction of skin, melanochrome and color spot increases the weight of, thereby avoid that skin premature aging, cutin form, coarsely chap, the formation of chloasma and freckle, prevent most of solar dermatitis and illumination allergy that UVA causes, therefore be widely used in the sunscreen products.In April, 1997, U.S. FDA is classified it as nonprescription drugs (OTC), permits using in the U.S., and European Union and Japan have also ratified its use, is sun-screening agent safely and effectively.
Summary of the invention
The present invention proposes the preparation method of a kind of 4-tertiary butyl-4 '-methoxy dibenzoyl methane, have following technical process: with 4-p t butylbenzoic acid methyl esters and 4-methoxyacetophenone is raw material, in basic catalyst and related solvents, carry out condensation reaction, get the 4-tertiary butyl-4 '-methoxy dibenzoyl methane raw product.The thick 4-tertiary butyl-4 '-methoxy dibenzoyl methane obtains the 4-tertiary butyl-4 '-methoxy dibenzoyl methane product behind decolorizing and refining.
As preferably: described basic catalyst can be yellow soda ash, sodium hydroxide, sodium methylate, sodium amide or butyllithium, preferred sodium amide.
As preferably: the consumption of described basic catalyst sodium amide is 0.5～2.5 times of material molar ratio, preferred 1.3～1.7 times.
As preferably: described solvent can be alcoholic solvent or varsol, preferred hydrocarbons kind solvent, more preferably aromatic hydrocarbon solvent.
As preferably: described aromatic hydrocarbon solvent is benzene, toluene or dimethylbenzene, preferred toluene solvant.
Reactional equation of the present invention is:
The invention has the beneficial effects as follows that the preparation method of the 4-tertiary butyl-4 ' of the present invention-methoxy dibenzoyl methane has following advantage:
1, production cost is low, environmental pollution is little, product odour is little
Owing to use toluene to be reaction solvent and recrystallization solvent, this solvent energy recycled has reduced production cost, has reduced environmental pollution.And because the volatility of toluene solvant is big, remove easily in treating process, product odour is little.
2, product colour is shallow, quality good, yield is high, the market competitiveness is strong, is easy to promote
Owing to adopt the moderate sodium amide of alkalescence as catalyzer, raw material substantially can total overall reaction, and reaction can steadily carry out, and side reaction is few.During aftertreatment, through decolorizing and refining, the finished product are of light color, quality good, yield is high, the market competitiveness is strong, are easy to industry and promote.
Embodiment
Embodiment 1:
In being installed, drops into by churned mechanically 1L reaction flask 300ml toluene, 21.6g (0.4mol) catalyzer sodium amide, 60.8g (0.318mol) 4-p t butylbenzoic acid methyl esters.Be warming up to 100-108 ℃, begin to add 38g (0.253mol) 4-methoxyacetophenone.Refluxing is incubated 4 hours, and reaction finishes.Cool to 80 ℃ and add water 300ml.Branch vibration layer, after organic layer was washed 2 times, toluene (this toluene is except that recycled behind the moisture) was reclaimed in distillation, and crystallisation by cooling gets crude product 78g.With toluene decolorizing and refining 2 times, product 53g, yield (in the 4-methoxyacetophenone) is 67.9%.Product is the off-white color crystalline powder, detects through GC, and purity reaches more than 99.5%, fusing point 84-85 ℃, and weight loss on drying≤0.5%.
Embodiment 2:
In being installed, drops into by churned mechanically 1L reaction flask 300ml recycled toluene, 23.2g (0.43mol) catalyzer sodium amide, 60.8g (0.318mol) 4-p t butylbenzoic acid methyl esters.Be warming up to 100-108 ℃, begin to add 38g (0.253mol) 4-methoxyacetophenone.Refluxing is incubated 4 hours, and reaction finishes.Cool to 80 ℃ and add water 300ml.Branch vibration layer after organic layer is washed 2 times, adopts the post-treating method of embodiment 1 can get product 54g, and yield (4-p-methoxy-acetophenone meter) is 69.2%.Product is the off-white color crystalline powder, detects through GC, and purity reaches more than 99.5%, fusing point 84-85 ℃.Weight loss on drying≤0.5%.
Claims (1)
1. the preparation method of the 4-tertiary butyl-4 '-methoxy dibenzoyl methane, it is characterized in that having following technical process: with 4-p t butylbenzoic acid methyl esters and 4-methoxyacetophenone is raw material, in sodium amide and toluene solvant, carry out condensation reaction, the consumption of sodium amide is 1.3～1.7 times of material molar ratio, temperature of reaction is 100 ℃～108 ℃, get the 4-tertiary butyl-4 '-methoxy dibenzoyl methane raw product, the thick 4-tertiary butyl-4 '-methoxy dibenzoyl methane obtains the 4-tertiary butyl-4 '-methoxy dibenzoyl methane product behind the toluene decolorizing and refining.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2006101185392A CN1958549B (en) | 2006-11-21 | 2006-11-21 | Method for preparing tertiary butyl 4' methoxy dibenzoyl methane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2006101185392A CN1958549B (en) | 2006-11-21 | 2006-11-21 | Method for preparing tertiary butyl 4' methoxy dibenzoyl methane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1958549A CN1958549A (en) | 2007-05-09 |
| CN1958549B true CN1958549B (en) | 2011-02-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2006101185392A Active CN1958549B (en) | 2006-11-21 | 2006-11-21 | Method for preparing tertiary butyl 4' methoxy dibenzoyl methane |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786403B (en) * | 2012-07-30 | 2014-11-12 | 黄冈美丰化工科技有限公司 | Preparation method for 4-tertiary butyl-4'-methoxy dibenzoyl methane |
| CN104876814B (en) * | 2015-05-28 | 2017-02-01 | 江西永通科技股份有限公司 | Synthetic method of avobenzone |
| CN109305897B (en) * | 2017-07-27 | 2021-08-24 | 安徽圣诺贝化学科技有限公司 | Production process of high-yield 1, 3-diphenyl propylene diketone compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4387089A (en) * | 1978-11-13 | 1983-06-07 | Givaudan Corporation | 4-(1,1-Dimethylethyl)-4'-methoxydibenzoylmethane |
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2006
- 2006-11-21 CN CN2006101185392A patent/CN1958549B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4387089A (en) * | 1978-11-13 | 1983-06-07 | Givaudan Corporation | 4-(1,1-Dimethylethyl)-4'-methoxydibenzoylmethane |
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| CN1958549A (en) | 2007-05-09 |
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