CN110776436A - Synthesis method and application of 4' -dimethylamino-2, 2-diethoxyacetophenone - Google Patents
Synthesis method and application of 4' -dimethylamino-2, 2-diethoxyacetophenone Download PDFInfo
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- CN110776436A CN110776436A CN201911105602.2A CN201911105602A CN110776436A CN 110776436 A CN110776436 A CN 110776436A CN 201911105602 A CN201911105602 A CN 201911105602A CN 110776436 A CN110776436 A CN 110776436A
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- dimethylamino
- diethoxyacetophenone
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- ethyl nitrite
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
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Abstract
The invention provides a synthesis method of 4 '-dimethylamino-2, 2-diethoxyacetophenone, which is characterized in that 4-dimethylamino acetophenone is adopted as a starting material and reacts with ethyl nitrite under the catalysis of acid or alkali to obtain the 4' -dimethylamino-2, 2-diethoxyacetophenone. The invention also provides application of the 4' -dimethylamino-2, 2-diethoxyacetophenone. The invention has the following beneficial effects: does not generate carcinogenicity or reproductive toxicity, can be applied to printing ink and has good application prospect.
Description
[ technical field ] A method for producing a semiconductor device
The invention relates to the technical field of photoinitiators, and particularly relates to a synthesis method and application of 4' -dimethylamino-2, 2-diethoxyacetophenone.
[ background of the invention ]
The UV light curing technology is a novel technology appeared in the middle of the 20 th century, and is a process for initiating a liquid substance with chemical reaction activity to be quickly converted into a solid by using ultraviolet light (the wavelength is 200-400nm) as an energy source. Compared with the traditional heat curing technology, the method has the advantages of high curing speed, high efficiency, less pollution, excellent performance and low cost, and is a new 'green' technology which is developed rapidly. The UV light-cured product consists of three parts of materials, namely a light-cured resin, a diluent and a photoinitiator.
In recent years, with the strict control of VOC emission in China, the UV light curing technology becomes more and more important, and will gradually replace the traditional thermal curing and two-component curing, so that the UV light curing technology develops more rapidly. In addition to the disablement of some conventional photoinitiators, such as ITX,907 and TPO, it is necessary to develop new photoinitiators with high safety to replace the conventional photoinitiators.
The compounds of α -hydroxyacetophenone and α -aminoacetophenone are the photoinitiators for free radical photopolymerization reactions commonly used in the market today, which are disclosed in various patent documents, such as PCT international publication nos. 2008122504A1, 2005014515A2 and 2008084853a1, us patents 4582862, 4318791, 4795766, 4992547, 5541308, 5077402, 4559371, 4739052, 7482392B2, german patent 2808459 and japanese patent 2009203299a, patent applications with chinese publication/publication nos. 1668648a, 1871200a, 1942424A and 101104582A also disclose some mono-and di-functionalized α -hydroxyacetophenone and α -aminoacetophenone.
[ summary of the invention ]
The invention discloses a synthesis method of 4' -dimethylamino-2, 2-diethoxyacetophenone, and aims to solve the problems involved in the background technology.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a synthesis method of 4 ' -dimethylamino-2, 2-diethoxyacetophenone adopts 4-dimethylamino acetophenone as a starting material, and reacts with ethyl nitrite under the catalysis of acid or alkali to obtain the 4 ' -dimethylamino-2, 2-diethoxyacetophenone, wherein the 4 ' -dimethylamino-2, 2-diethoxyacetophenone intermediate has the following general formula:
preferably, the base is selected from sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide.
Preferably, the reaction temperature in the synthesis of the photoinitiator 4' -dimethylamino-2, 2-diethoxyacetophenone is 30-50 ℃.
The invention also provides application of the 4 '-dimethylamino-2, 2-diethoxyacetophenone, wherein the 4' -dimethylamino-2, 2-diethoxyacetophenone is applied to ink.
The invention has the following beneficial effects: does not generate carcinogenicity or reproductive toxicity, can be applied to printing ink and has good application prospect.
[ detailed description ] embodiments
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to specific embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a synthesis method of 4 ' -dimethylamino-2, 2-diethoxyacetophenone, which adopts 4-dimethylamino acetophenone as a starting material and reacts with ethyl nitrite under the catalysis of acid or alkali to obtain the 4 ' -dimethylamino-2, 2-diethoxyacetophenone, wherein the synthesis chemical formula of the 4 ' -dimethylamino-2, 2-diethoxyacetophenone is as follows:
the 4' -dimethylamino-2, 2-diethoxyacetophenone intermediate has the following general formula:
wherein the base is selected from sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide. The reaction temperature in the synthesis of the photoinitiator 4' -dimethylamino-2, 2-diethoxyacetophenone is 30-50 ℃.
The invention also provides application of the 4 '-dimethylamino-2, 2-diethoxyacetophenone, wherein the 4' -dimethylamino-2, 2-diethoxyacetophenone is applied to ink.
The present invention will be described in detail with reference to specific examples 1 to 3.
Example 1
Adding 300g of toluene and 80g of p-dimethylaminoacetophenone into a 1000-ml reaction bottle, introducing hydrogen chloride gas and ethyl nitrite gas at the same time at the temperature of 30-60 ℃, wherein the ventilation capacity of the hydrogen chloride gas is 22g, the ventilation capacity of the ethyl nitrite is 85g, keeping the reaction temperature at 30-60 ℃ in the ventilation process, after the reaction is finished, adding 200g of water for washing once, separating liquid, removing a water layer, removing toluene to obtain a crude product, and carrying out reduced pressure distillation to obtain 98g of a product, wherein the yield is 79.5%.
Example 2
Adding 350g of toluene and 80g of p-dimethylaminoacetophenone into a 1000-ml reaction bottle, introducing hydrogen chloride gas and ethyl nitrite gas at the same time at the temperature of 30-60 ℃, wherein the ventilation capacity of the hydrogen chloride gas is 25g, and the ventilation capacity of the ethyl nitrite is 90g, maintaining the reaction temperature at 30-60 ℃ in the ventilation process, after the reaction is finished, adding 200g of water for washing once, separating liquid, removing a water layer, removing toluene to obtain a crude product, and carrying out reduced pressure distillation to obtain 96g of a product, wherein the yield is 77.9%.
Example 3
Adding 400g of toluene and 80g of p-dimethylaminoacetophenone into a 1000-ml reaction bottle, introducing hydrogen chloride gas and ethyl nitrite gas at the same time at the temperature of 30-60 ℃, wherein the ventilation capacity of the hydrogen chloride gas is 25g, the ventilation capacity of the ethyl nitrite is 85g, keeping the reaction temperature at 30-60 ℃ in the ventilation process, after the reaction is finished, adding 200g of water for washing once, separating liquid, removing a water layer, removing toluene to obtain a crude product, and carrying out reduced pressure distillation to obtain 100g of the product, wherein the yield is 81.2%.
The invention has the following beneficial effects: does not generate carcinogenicity or reproductive toxicity, can be applied to printing ink and has good application prospect.
While embodiments of the invention have been disclosed above, it is not limited to the applications set forth in the description and embodiments, which are fully applicable to various fields of endeavor for which the invention pertains, and further modifications may readily be made by those skilled in the art, it being understood that the invention is not limited to the details shown and described without departing from the generic concept as defined by the claims and the equivalents thereof.
Claims (4)
1. A synthesis method of 4 ' -dimethylamino-2, 2-diethoxyacetophenone is characterized in that 4-dimethylamino acetophenone is adopted as a starting material and reacts with ethyl nitrite under the catalysis of acid or alkali to obtain the 4 ' -dimethylamino-2, 2-diethoxyacetophenone, wherein the 4 ' -dimethylamino-2, 2-diethoxyacetophenone intermediate has the following general formula:
2. the method for synthesizing 4' -dimethylamino-2, 2-diethoxyacetophenone according to claim 1, wherein the base is selected from sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide.
3. The method for synthesizing 4 '-dimethylamino-2, 2-diethoxyacetophenone according to claim 1, wherein the reaction temperature in the synthesis of the photoinitiator 4' -dimethylamino-2, 2-diethoxyacetophenone is 30-50 ℃.
4. The application of the 4 '-dimethylamino-2, 2-diethoxyacetophenone is characterized in that the 4' -dimethylamino-2, 2-diethoxyacetophenone is applied to ink.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201911105602.2A CN110776436A (en) | 2019-11-13 | 2019-11-13 | Synthesis method and application of 4' -dimethylamino-2, 2-diethoxyacetophenone |
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| CN201911105602.2A CN110776436A (en) | 2019-11-13 | 2019-11-13 | Synthesis method and application of 4' -dimethylamino-2, 2-diethoxyacetophenone |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0122479A1 (en) * | 1983-03-18 | 1984-10-24 | Wacker-Chemie GmbH | 3-Chloro-1,1-dialkoxy-acetones and process for their preparation |
| EP0222217A2 (en) * | 1985-11-08 | 1987-05-20 | BASF Aktiengesellschaft | Dialkoxyketones and a method for their production |
| US4895586A (en) * | 1985-11-21 | 1990-01-23 | Basf Aktiengesellschaft | Triazolyl glycol ethers, fungicides and bioregulators |
| US5124489A (en) * | 1989-12-14 | 1992-06-23 | Hoechst Celanese Corporation | Process for preparing phenethanol ethers by the reduction of corresponding phenylglyoxal acetals |
| US5254753A (en) * | 1992-02-25 | 1993-10-19 | Hoechst Celanese Corporation | Production of aryl ethanols |
| CN101735031A (en) * | 2009-12-21 | 2010-06-16 | 南开大学 | Synthetic method of 2,2-diethoxy acetophenone photoinitiator |
-
2019
- 2019-11-13 CN CN201911105602.2A patent/CN110776436A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0122479A1 (en) * | 1983-03-18 | 1984-10-24 | Wacker-Chemie GmbH | 3-Chloro-1,1-dialkoxy-acetones and process for their preparation |
| EP0222217A2 (en) * | 1985-11-08 | 1987-05-20 | BASF Aktiengesellschaft | Dialkoxyketones and a method for their production |
| US4895586A (en) * | 1985-11-21 | 1990-01-23 | Basf Aktiengesellschaft | Triazolyl glycol ethers, fungicides and bioregulators |
| US5124489A (en) * | 1989-12-14 | 1992-06-23 | Hoechst Celanese Corporation | Process for preparing phenethanol ethers by the reduction of corresponding phenylglyoxal acetals |
| US5254753A (en) * | 1992-02-25 | 1993-10-19 | Hoechst Celanese Corporation | Production of aryl ethanols |
| CN101735031A (en) * | 2009-12-21 | 2010-06-16 | 南开大学 | Synthetic method of 2,2-diethoxy acetophenone photoinitiator |
Non-Patent Citations (2)
| Title |
|---|
| 宋俊林等: "α,α一二烷氧基苯乙酮类光敏剂的合成", 《化学通报》 * |
| 魏忠诚等: "《光纤材料制备技术》", 30 September 2016 * |
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