CN101735060A - Novel method for synthesizing ethyl pyruvate - Google Patents
Novel method for synthesizing ethyl pyruvate Download PDFInfo
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- CN101735060A CN101735060A CN200910248986A CN200910248986A CN101735060A CN 101735060 A CN101735060 A CN 101735060A CN 200910248986 A CN200910248986 A CN 200910248986A CN 200910248986 A CN200910248986 A CN 200910248986A CN 101735060 A CN101735060 A CN 101735060A
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- ethyl ester
- acid ethyl
- pyruvic acid
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Abstract
The invention relates to a method for synthesizing an organic compound. The method for synthesizing ethyl pyruvate adopts ethyl lactate and sodium hydroxide bicarbonate as raw materials, and the raw materials of ethyl lactate and sodium bicarbonate are prepared according to certain mole ratios and are processed by synthetic reaction in an organic solvent under the existence of an oxynitride catalyst and oxidizer trichloroisocyanuric acid; and after reaction, reaction liquid is processed by filtration, solvent removal, pressure reduction and distillation and then is collected to obtain the ethyl pyruvate product. Compared with the traditional method, the method for synthesizing the ethyl pyruvate is outstandingly characterized by reasonable proportion of reaction raw materials, simple and easily operated process, nearly 100 percent of percent conversion of the raw materials by particularly adopting the novel catalyst oxynitride and the oxidizer trichloroisocyanuric acid (TCCA), capability of quantitative reaction and high purity and yield of products obtained by reaction, thereby meeting the requirement of each industry on application.
Description
One, technical field:
The present invention relates to the synthetic method of organic compound.
Two, background technology:
Pyruvic Acid Ethyl ester (Ethyl pyruvate) has another name called ethyl 2-oxopropanoate (Ethyl 2-oxopropionate), Brenztraubensaeure-ethylester, and molecular formula is C5H8O3.
Pyruvic Acid Ethyl ester is important organic synthesis intermediate, widespread use in industries such as medicine, makeup, agricultural chemicals, spices and laserable material.As medicine intermediate, can be used for medicines such as synthetic cardiovascular expander; Be applied to whiten and the makeup of skin nutrition, can promote skin wound healing, prevention and treatment with cracking, peel off the dermatosis that turns to feature with squama; As the high-efficiency activated composition in the air freshener, can effectively remove airborne ammonia and thiomethyl alcohol; Pyruvic Acid Ethyl ester itself has special fragrance, thereby can be applied in essence, the spices; Pyruvic Acid Ethyl ester also is the important source material of synthetic resins and plastics simultaneously.
Be the raw material synthetic method at present with the ethyl lactate, mainly be to adopt NO2 oxidation style, potassium permanganate oxidation method, hypochlorite oxidation method, ferrous sulfate hydrogen peroxide oxidation method etc., characteristics are convenient and swift, but these method for oxidation ethyl lactate oxidations are not thorough, yield is low, because the boiling point of material acid ethyl ester and Pyruvic Acid Ethyl ester is more or less the same, obtain relatively difficulty of highly purified Pyruvic Acid Ethyl ester, product purity is low.
Three, summary of the invention:
The objective of the invention is to overcome above-mentioned not enough problem, a kind of synthetic method of Pyruvic Acid Ethyl ester is provided, adopt a kind of novel catalyzer, is oxygenant with TCCA, can carry out quantitative reaction, selectivity 100%, and technology is simple, obtains highly purified Pyruvic Acid Ethyl ester.
The technical scheme that the present invention is adopted for achieving the above object is: the synthetic method of Pyruvic Acid Ethyl ester, adopt material acid ethyl ester and hydrogen-carbonate sodium oxide, the mol ratio of material acid ethyl ester and sodium bicarbonate, in organic solvent, nitrogen oxide catalyst and oxygenant trichloroisocyanuric acid exist down and carry out building-up reactions, react finish afterreaction liquid after filtration, desolventize, underpressure distillation collect the product Pyruvic Acid Ethyl ester.
Described material acid ethyl ester and sodium bicarbonate, catalyzer, organic solvent drops in the reactor, stir and cooling, and then add oxygenant trichloroisocyanuric acid (TCCA) in batches, the oxygenant adition process keeps 14～15 ℃ of reactor temperatures, after the oxygenant adding finishes, keep 13～15 ℃ of reactions of reactor temperature, sampling analysis (GC) behind the reaction 2h, content of ethyl lactate＜0.5% o'clock, stop to stir, filtering reacting liquid, filter cake washed with dichloromethane, merging filtrate, the filtrate air distillation steams organic solvent, cut is collected in underpressure distillation then, obtains the Pyruvic Acid Ethyl ester of content more than 99%.
Described catalyzer adopts 2,2,6,6-tetramethyl piperidine oxynitride, methylmorpholine oxynitride or pyridine nitric oxide.
Described catalyst levels is 1～2% of an ethyl lactate quality.
The consumption of described oxygenant trichloroisocyanuric acid is 0.75-1 a times of ethyl lactate quality.
Described organic solvent adopts methylene dichloride or ethylene dichloride, and consumption is 3-5 a times of ethyl lactate quality.
The synthetic method of Pyruvic Acid Ethyl ester of the present invention is compared with existing method, has outstanding feature: the reaction raw materials reasonable ratio, technology is simple to operation, particularly adopt novel catalyzer oxynitride and oxygenant TCCA, it is nearly 100% that feed stock conversion reaches, and can carry out quantitative reaction, and the product purity height that makes of reaction, the yield height has satisfied the application demand of every profession and trade.
Four, embodiment:
Below in conjunction with specific embodiment the present invention is described in further detail, but the present invention is not limited to specific embodiment.
Embodiment 1
The synthetic method of Pyruvic Acid Ethyl ester, concrete technology is: in the 500ml four-hole bottle, add 50g ethyl lactate, 37.5g sodium bicarbonate, 0.75g catalyzer 2,2,6,6-tetramethyl piperidine oxynitride, 250g methylene dichloride.Mechanical stirring, the ice-water bath cooling.Add 37.5g oxygenant trichloroisocyanuric acid (TCCA) in batches, keep 14～15 ℃ of reactor temperatures, add TCCA after, keep 13～15 ℃ of reactor temperatures, sampling analysis (GC) behind the reaction 2h, content of ethyl lactate＜0.5% stops to stir.Filtering reacting liquid, the filter cake washed with dichloromethane, merging filtrate, the filtrate air distillation steams methylene dichloride, and then underpressure distillation collection cut, obtains the Pyruvic Acid Ethyl ester of content more than 99%.
Embodiment 2
The synthetic method of Pyruvic Acid Ethyl ester, concrete technology is: in the 500ml four-hole bottle, add 50g ethyl lactate, 40g sodium bicarbonate, 0.5g catalyzer methylmorpholine oxynitride, 250g ethylene dichloride.Mechanical stirring, the ice-water bath cooling.Add 40g oxygenant TCCA in batches, keep 14～15 ℃ of reactor temperatures, add TCCA after, keep 13～15 ℃ of reactor temperatures, sampling analysis (GC) behind the reaction 2h, content of ethyl lactate＜0.5% stops to stir.Filtering reacting liquid, the filter cake washed with dichloromethane, merging filtrate, the filtrate air distillation steams methylene dichloride, and then underpressure distillation collection cut, obtains the Pyruvic Acid Ethyl ester of content more than 99%.
Embodiment 3
The synthetic method of Pyruvic Acid Ethyl ester, concrete technology is: in the 500ml four-hole bottle, add 50g ethyl lactate, 40g sodium bicarbonate, 1.0g catalyzer pyridine nitric oxide, 250g ethylene dichloride.Mechanical stirring, the ice-water bath cooling.Add 50g oxygenant TCCA in batches, keep 14～15 ℃ of reactor temperatures, add TCCA after, keep 13～15 ℃ of reactor temperatures, sampling analysis (GC) behind the reaction 2h, content of ethyl lactate＜0.5% stops to stir.Filtering reacting liquid, the filter cake washed with dichloromethane, merging filtrate, the filtrate air distillation steams methylene dichloride, and then underpressure distillation collection cut, obtains the Pyruvic Acid Ethyl ester of content more than 99%.
Claims (6)
1. the synthetic method of Pyruvic Acid Ethyl ester, it is characterized in that: adopt material acid ethyl ester and hydrogen-carbonate sodium oxide, the mol ratio of material acid ethyl ester and hydrogen-carbonate sodium oxide, in organic solvent, nitrogen oxide catalyst and oxygenant trichloroisocyanuric acid exist down and carry out building-up reactions, react finish afterreaction liquid after filtration, desolventize, underpressure distillation collect the product Pyruvic Acid Ethyl ester.
2. Pyruvic Acid Ethyl ester according to claim 1, it is characterized in that: material acid ethyl ester and sodium bicarbonate, catalyzer, organic solvent drops in the reactor, stir and cooling, and then add the oxygenant trichloroisocyanuric acid in batches, the oxygenant adition process keeps 14～15 ℃ of reactor temperatures, after the oxygenant adding finishes, keeps 13～15 ℃ of reactions of reactor temperature, sampling analysis behind the reaction 2h, content of ethyl lactate＜0.5% o'clock stops to stir filtering reacting liquid, the filter cake washed with dichloromethane, merging filtrate, the filtrate air distillation steams organic solvent, then underpressure distillation, collect cut, obtain the Pyruvic Acid Ethyl ester of content more than 99%.
3. Pyruvic Acid Ethyl ester according to claim 1 and 2 is characterized in that: catalyzer adopts 2,2,6,6-tetramethyl piperidine oxynitride, methylmorpholine oxynitride or pyridine nitric oxide.
4. Pyruvic Acid Ethyl ester according to claim 1 and 2 is characterized in that: catalyst levels is 1～2% of an ethyl lactate quality.
5. Pyruvic Acid Ethyl ester according to claim 1 and 2 is characterized in that: the consumption of oxygenant trichloroisocyanuric acid is 0.75-1 a times of ethyl lactate quality.
6. Pyruvic Acid Ethyl ester according to claim 1 and 2 is characterized in that: organic solvent employing ethylene dichloride alkane, consumption are 3-5 times of ethyl lactate quality
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| CN200910248986A CN101735060A (en) | 2009-12-29 | 2009-12-29 | Novel method for synthesizing ethyl pyruvate |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777507A (en) * | 2016-04-15 | 2016-07-20 | 大连信科化工有限公司 | Method for synthesizing methoxy acetone |
| CN105801388A (en) * | 2016-04-15 | 2016-07-27 | 大连信科化工有限公司 | Method for preparing methoxyacetone by oxidizing 1-methoxy-2-propanol with chlorine |
| CN107602393A (en) * | 2017-09-28 | 2018-01-19 | 安徽省庆云医药股份有限公司 | A kind of method that benzyl position C H keys are direct oxidation into ketone or acid |
| CN110054564A (en) * | 2019-05-24 | 2019-07-26 | 中触媒新材料股份有限公司 | A kind of method that serialization prepares ethyl pyruvate |
| CN110092721A (en) * | 2019-06-11 | 2019-08-06 | 湖北朗昕生化药业有限公司 | A kind of pyruvate synthesis preparation method |
| CN112811995A (en) * | 2021-01-14 | 2021-05-18 | 惠泽化学科技(濮阳)有限公司 | Synthesis method of 4-substituent cyclohexanone liquid crystal intermediate |
| CN115611742A (en) * | 2022-09-09 | 2023-01-17 | 常茂生物化学工程股份有限公司 | Method for preparing and extracting high-purity ethyl pyruvate by using mixed distillation method |
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| CN101318902A (en) * | 2008-06-27 | 2008-12-10 | 烟台海岸带可持续发展研究所 | Method for preparing ethyl pyruvate by oxidizing ethyl lactate with chlorine gas |
| CN101318903A (en) * | 2008-06-27 | 2008-12-10 | 烟台海岸带可持续发展研究所 | Method for preparing ethyl pyruvate |
| CN101486621A (en) * | 2008-01-16 | 2009-07-22 | 中国科学院大连化学物理研究所 | Method for preparing aldehyde or ketone by catalyzing air and oxidizing alcohol |
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- 2009-12-29 CN CN200910248986A patent/CN101735060A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101486621A (en) * | 2008-01-16 | 2009-07-22 | 中国科学院大连化学物理研究所 | Method for preparing aldehyde or ketone by catalyzing air and oxidizing alcohol |
| CN101318902A (en) * | 2008-06-27 | 2008-12-10 | 烟台海岸带可持续发展研究所 | Method for preparing ethyl pyruvate by oxidizing ethyl lactate with chlorine gas |
| CN101318903A (en) * | 2008-06-27 | 2008-12-10 | 烟台海岸带可持续发展研究所 | Method for preparing ethyl pyruvate |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777507A (en) * | 2016-04-15 | 2016-07-20 | 大连信科化工有限公司 | Method for synthesizing methoxy acetone |
| CN105801388A (en) * | 2016-04-15 | 2016-07-27 | 大连信科化工有限公司 | Method for preparing methoxyacetone by oxidizing 1-methoxy-2-propanol with chlorine |
| CN107602393A (en) * | 2017-09-28 | 2018-01-19 | 安徽省庆云医药股份有限公司 | A kind of method that benzyl position C H keys are direct oxidation into ketone or acid |
| CN110054564A (en) * | 2019-05-24 | 2019-07-26 | 中触媒新材料股份有限公司 | A kind of method that serialization prepares ethyl pyruvate |
| CN110092721A (en) * | 2019-06-11 | 2019-08-06 | 湖北朗昕生化药业有限公司 | A kind of pyruvate synthesis preparation method |
| CN112811995A (en) * | 2021-01-14 | 2021-05-18 | 惠泽化学科技(濮阳)有限公司 | Synthesis method of 4-substituent cyclohexanone liquid crystal intermediate |
| CN115611742A (en) * | 2022-09-09 | 2023-01-17 | 常茂生物化学工程股份有限公司 | Method for preparing and extracting high-purity ethyl pyruvate by using mixed distillation method |
| CN115611742B (en) * | 2022-09-09 | 2023-10-03 | 常茂(大连)新材料有限公司 | Method for preparing and extracting high-purity ethyl pyruvate by using mixed distillation method |
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Application publication date: 20100616 |