CN108440289B - Method for preparing pyruvate by water-phase catalytic oxidation of lactate - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/10—Magnesium; Oxides or hydroxides thereof
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- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
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- B01J37/34—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation
- B01J37/341—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation
- B01J37/343—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation of ultrasonic wave energy
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- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
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Abstract
The invention discloses a method for preparing pyruvate by catalyzing and oxidizing lactate in a water phase, which takes lactate as a raw material, oxygen or air as an oxidant and supported nano magnesium oxide as a catalyst to prepare pyruvate through a catalytic oxidation reaction; the catalytic reaction can be carried out under normal pressure, an organic solvent is not needed, the product yield is high, and the catalyst can be recycled.
Description
Technical Field
The invention relates to preparation of pyruvate, in particular to a method for preparing pyruvate by catalyzing and oxidizing lactate in a water phase.
Background
Pyruvate is an important fine chemical and chemical intermediate, and can be widely applied to industries such as medicines (sedatives, antiviral agents and the like), foods, spices, daily chemicals (preservatives, whitening agents and the like). There are many synthetic routes for pyruvate, for example, pyruvate can be obtained by dehydration and decarboxylation of tartrate, but the method has low product yield, high production cost and serious environmental pollution; pyruvic acid can also be prepared by oxidizing aqueous solution of methylglyoxal with chlorine, but this method is also costly to produce and pollutes the environment. Of the various synthetic methods for pyruvate esters, the preparation of pyruvate esters by oxidation of lactate is considered to be the most direct and efficient route and is therefore of great interest.
There are many routes for synthesizing pyruvate, such as tartrate conversion, which has low yield, high cost and serious environmental pollution. The most direct and effective way to prepare pyruvate through lactate oxidation is that the method for preparing pyruvate from lactate mainly comprises lactate gas-phase oxidation method and lactate liquid-phase oxidation method; wherein, the lactate gas-phase oxidation method has higher reaction temperature, high requirement on equipment and high production cost; the liquid phase oxidation method of lactate mainly adopts oxidants such as potassium permanganate to carry out oxidation, and the method has serious pollution and low oxidation efficiency. It is reported that the supported noble metal catalyst, oxygen as oxidant, water as solvent and lactate are used for catalytic oxidation to prepare pyruvate.
The main methods for preparing pyruvate by oxidation of lactate are the stoichiometric oxidation and the catalytic oxidation. The metering oxidation method mainly adopts an oxidant such as KMnO4 and the like to oxidize the lactate, but the method has serious pollution and low oxidation efficiency. The catalytic oxidation method, particularly the catalytic oxidation method taking molecular oxygen as an oxygen source, has the remarkable advantages of small pollution and the like. Dudeck et al have reported the catalytic oxidation of lactate to pyruvate using crystalline silver, but the process requires a reaction temperature of 450 ℃ and 700 ℃ and yields of pyruvate are low (65-75%) (U.S. Pat. No. 6, 4229590). Shenwei et al, using Ag/NaY as a catalyst, catalyzed and oxidized lactate to prepare pyruvate, showed a product selectivity of 91.1% and a reaction temperature of 400 deg.C (Chin.J.Catal.1998,19, 428-. Hayashi et al TeO 2-MoO 3 as catalyst, and the ethyl lactate is catalytically oxidized at 300 ℃ with the conversion rate of about 80% (Catal. Lett.1993,19, 273) and the reaction temperature is still higher in the process.
Therefore, the development of the method for preparing pyruvate by catalyzing and selectively oxidizing lactate under mild conditions by taking air as an oxidant has important significance and application prospect.
Disclosure of Invention
The invention aims to provide a method for preparing pyruvate by catalyzing and oxidizing lactate in an aqueous phase.
The reaction raw material used in the present invention may be one or more of methyl lactate, ethyl lactate, propyl lactate and butyl lactate.
The carrier of the loaded nano magnesium oxide is selected from one or more of activated carbon, silica gel, ZSM-5 zeolite and ZSM-11 zeolite. The preparation method comprises the following steps:
1) weighing MgCl2Dissolving in absolute ethyl alcohol, adding PEG400 as a dispersing agent, heating to 50-60 ℃ after uniform mixing, slowly dropwise adding a certain amount of ammonia water ethanol solution with a volume ratio of (1:1) under continuous magnetic stirring to form white precipitate; keeping the temperature and reacting for 1.5h, taking out, and standing and aging at room temperature; filtering and separating the precipitate, washing a filter cake for a plurality of times by using water and ethanol respectively, and then carrying out vacuum drying at the temperature of 60 ℃ to obtain a white precursor; finally calcining for 1.5h at 500 ℃ in air atmosphere to obtain nano magnesium oxide powder;
2) adding the nano magnesium oxide into absolute ethyl alcohol, uniformly stirring, and performing ultrasonic dispersion with the ultrasonic frequency of 40KHz for 15min to form a nano magnesium oxide ethanol solution; and adding a carrier into the prepared nano magnesium oxide ethanol solution, heating at 100-200 ℃, treating with ultrasonic frequency of 40KHz for 120min, performing centrifugal separation, drying in a vacuum freeze drying oven at the temperature of-80 ℃, and finally grinding and sieving to obtain the loaded nano magnesium oxide.
The mass ratio of the catalyst to the reaction substrate used in the method is 0.1-10.
The reaction is carried out in a pressure reactor, and oxygen or air is used as an oxygen source. Wherein the oxygen partial pressure is 0.05-2.0MPa, and the optimal oxygen partial pressure is 0.1-1.5 MPa. The reaction temperature is 40-160 ℃, and the optimal reaction temperature is 100-120 ℃. The reaction time is 0.5-15h, and the optimal reaction time is 3-7 h.
The catalyst is reused by adopting the following method: after the reaction is finished, the catalyst is separated by a centrifugal method, washed by deionized water until the pH value is 7, fully washed by ethanol and then dried. When the catalytic activity is remarkably reduced, the recovered catalyst can be reduced for 1-5 h under the condition of 150-250 ℃ in a hydrogen atmosphere. The obtained solid catalyst can be repeatedly used according to the method.
Compared with the prior art, the invention has the following characteristics:
(1) the method for preparing pyruvate by liquid-phase catalytic oxidation of lactate provided by the invention has the advantages of mild reaction conditions, high product yield and obvious advantages compared with the existing gas-phase oxidation method.
(2) Oxygen or air is used as an oxygen source, water is used as a reaction solvent, the cost is low, the raw materials are easy to obtain, and the generated waste is small. The product and the catalyst are easy to separate, and the catalyst can be recycled, so that the method has a good application prospect.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
[ example 1 ]
1) Weighing 1 part by weight of MgCl2Dissolving in absolute ethyl alcohol, and adding 2 parts by weight of PEG400 as a dispersing agent. After mixing evenly, heating to 60 ℃, slowly dripping a certain amount of ammonia water ethanol solution with the volume ratio of (1:1) under the continuous magnetic stirring to form white precipitate. After the dripping is finished, the reaction is continued for 1.5h under heat preservation, and the mixture is taken out, kept stand and aged at room temperature. And filtering and separating the precipitate, washing a filter cake for a plurality of times by using water and ethanol respectively, and drying in vacuum at the temperature of 60 ℃ to obtain a white precursor. And finally calcining the mixture for 1.5 hours at 500 ℃ in air atmosphere to obtain the nano magnesium oxide powder.
2) Adding the nano magnesium oxide into absolute ethyl alcohol, uniformly stirring, and performing ultrasonic dispersion with the ultrasonic frequency of 40KHz for 15min to form a nano magnesium oxide ethanol solution; adding activated carbon into the prepared nano magnesium oxide ethanol solution, heating at 100 ℃, treating with ultrasonic frequency of 40KHz, performing ultrasonic treatment for 120min, performing centrifugal separation, drying in a vacuum freeze drying oven at the temperature of-80 ℃, and finally grinding and sieving to obtain the activated carbon-loaded nano magnesium oxide.
[ example 2 ]
1) Weighing 1 part by weight of MgCl2Dissolving in absolute ethyl alcohol, and adding 2 parts by weight of PEG400 as a dispersing agent. After mixing well, literWhen the temperature is 60 ℃, slowly dropwise adding a certain amount of ammonia water ethanol solution with the volume ratio of (1:1) under the continuous magnetic stirring to form white precipitate. After the dripping is finished, the reaction is continued for 1.5h under heat preservation, and the mixture is taken out, kept stand and aged at room temperature. And filtering and separating the precipitate, washing a filter cake for a plurality of times by using water and ethanol respectively, and drying in vacuum at the temperature of 60 ℃ to obtain a white precursor. And finally calcining the mixture for 1.5 hours at 500 ℃ in air atmosphere to obtain the nano magnesium oxide powder.
2) Adding the nano magnesium oxide into absolute ethyl alcohol, uniformly stirring, and performing ultrasonic dispersion with the ultrasonic frequency of 40KHz for 15min to form a nano magnesium oxide ethanol solution; adding ZSM-5 into the prepared nano magnesium oxide ethanol solution, heating at 100 ℃, treating with ultrasonic frequency of 40KHz, performing ultrasonic treatment for 120min, performing centrifugal separation, drying in a vacuum freeze drying oven at the temperature of-80 ℃, and finally grinding and sieving to obtain ZSM-5 loaded nano magnesium oxide.
[ example 3 ]
1) Weighing 1 part by weight of MgCl2Dissolving in absolute ethyl alcohol, and adding 2 parts by weight of PEG400 as a dispersing agent. After mixing evenly, heating to 60 ℃, slowly dripping a certain amount of ammonia water ethanol solution with the volume ratio of (1:1) under the continuous magnetic stirring to form white precipitate. After the dripping is finished, the reaction is continued for 1.5h under heat preservation, and the mixture is taken out, kept stand and aged at room temperature. And filtering and separating the precipitate, washing a filter cake for a plurality of times by using water and ethanol respectively, and drying in vacuum at the temperature of 60 ℃ to obtain a white precursor. And finally calcining the mixture for 1.5 hours at 500 ℃ in air atmosphere to obtain the nano magnesium oxide powder.
2) Adding the nano magnesium oxide into absolute ethyl alcohol, uniformly stirring, and performing ultrasonic dispersion with the ultrasonic frequency of 40KHz for 15min to form a nano magnesium oxide ethanol solution; adding silica gel into the prepared nano magnesium oxide ethanol solution, heating at 100 ℃, treating with ultrasonic frequency of 40KHz for 120min, centrifuging, drying in a vacuum freeze drying oven at-80 ℃, and finally grinding and sieving to obtain silica gel-loaded nano magnesium oxide.
[ example 4 ]
The methyl lactate is oxidized by the active carbon supported nano magnesium oxide catalyst to prepare the methyl pyruvate.
100g of methyl lactate and 300mL of deionized water are added into a reaction kettle, then 1g of the activated carbon-supported nano magnesium oxide catalyst prepared in the example 1 is added, oxygen is charged to 0.1MPa, the temperature is raised to 100 ℃ under continuous stirring, and the temperature is kept for 5 hours. If the oxygen partial pressure is reduced, the oxygen is supplemented, and the oxygen pressure is maintained at about 0.1 MPa. After the reaction was completed, it was cooled to room temperature. The product was analyzed by gas chromatography, and the yield of methyl pyruvate was 91%.
[ example 5 ]
The ZSM-5 loaded nano magnesium oxide catalyst oxidizes methyl lactate to prepare methyl pyruvate.
100g of methyl lactate and 300mL of deionized water are added into a reaction kettle, then 1g of the ZSM-5 supported nano magnesium oxide catalyst prepared in the example 2 is added, oxygen is charged to 0.1MPa, the temperature is raised to 100 ℃ under continuous stirring, and the reaction kettle is kept for 5 hours. If the oxygen partial pressure is reduced, the oxygen is supplemented, and the oxygen pressure is maintained at about 0.1 MPa. After the reaction was completed, it was cooled to room temperature. The product was analyzed by gas chromatography, and the yield of methyl pyruvate was 93%.
[ example 6 ]
The silica gel loaded nano magnesium oxide catalyst oxidizes methyl lactate to prepare methyl pyruvate.
100g of methyl lactate and 300mL of deionized water are added into a reaction kettle, then 1g of the silica gel supported nano magnesium oxide catalyst prepared in the embodiment 3 is added, oxygen is charged to 0.1MPa, the temperature is raised to 100 ℃ under continuous stirring, and the temperature is kept for 5 hours. If the oxygen partial pressure is reduced, the oxygen is supplemented, and the oxygen pressure is maintained at about 0.1 MPa. After the reaction was completed, it was cooled to room temperature. The product was analyzed by gas chromatography, and the yield of methyl pyruvate was 89%.
The foregoing description has disclosed fully preferred embodiments of the present invention. It should be noted that those skilled in the art can make modifications to the embodiments of the present invention without departing from the scope of the appended claims. Accordingly, the scope of the appended claims is not to be limited to the specific embodiments described above.
Claims (4)
1. A method for preparing pyruvate through aqueous phase catalytic oxidation of lactate is characterized in that air or oxygen is used as an oxygen source, supported nano magnesium oxide is used as a catalyst, aqueous solution is used as a medium, and the pyruvate is prepared through efficient catalytic oxidation of the lactate under mild conditions;
the carrier of the loaded nano magnesium oxide is selected from one or more of activated carbon, silica gel, ZSM-5 zeolite and ZSM-11 zeolite;
the preparation method of the supported nano magnesium oxide comprises the following steps: 1) weighing MgCl2Dissolving in absolute ethyl alcohol, adding PEG400 as a dispersing agent, heating to 50-60 ℃ after uniform mixing, slowly dropwise adding a certain amount of ammonia water ethanol solution with a volume ratio of 1:1 under continuous magnetic stirring to form white precipitate; keeping the temperature and reacting for 1.5h, taking out, and standing and aging at room temperature; filtering and separating the precipitate, washing a filter cake for a plurality of times by using water and ethanol respectively, and then carrying out vacuum drying at the temperature of 60 ℃ to obtain a white precursor; finally calcining for 1.5h at 500 ℃ in air atmosphere to obtain nano magnesium oxide powder; 2) adding the nano magnesium oxide into absolute ethyl alcohol, uniformly stirring, and performing ultrasonic dispersion with the ultrasonic frequency of 40KHz for 15min to form a nano magnesium oxide ethanol solution; and adding a carrier into the prepared nano magnesium oxide ethanol solution, heating at 100-200 ℃, treating with ultrasonic frequency of 40KHz for 120min, performing centrifugal separation, drying in a vacuum freeze drying oven at the temperature of-80 ℃, and finally grinding and sieving to obtain the loaded nano magnesium oxide.
2. The method of claim 1, wherein the raw material for the reaction is one or more of methyl lactate, ethyl lactate, propyl lactate, and butyl lactate.
3. The method for preparing pyruvate through aqueous phase catalytic oxidation of lactate according to claim 1, wherein: the mass ratio of the catalyst to the reaction substrate is 0.1-10.
4. The method for preparing pyruvate through aqueous phase catalytic oxidation of lactate according to claim 1, wherein: the reaction is carried out in a pressure reactor, and oxygen or air is taken as an oxygen source; wherein the oxygen partial pressure is 0.05-2.0 MPa; the reaction temperature is 40-160 ℃; the reaction time is 0.5-15 h.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH099960A (en) * | 1995-07-03 | 1997-01-14 | Gekkeikan Sake Co Ltd | New pyruvic oxidase, its production and analysis of pyruvic acid |
| CN101579625A (en) * | 2008-05-15 | 2009-11-18 | 湖南大学 | Catalyst and reaction process for preparing pyruvic acid by lactic acid in catalytic oxydehydrogenation way |
| CN104276951A (en) * | 2013-07-02 | 2015-01-14 | 中国科学院大连化学物理研究所 | Method for using water phase to catalytically oxidize lactates for preparing pyruvates |
| CN106111173A (en) * | 2016-06-28 | 2016-11-16 | 厦门市净屋环保科技有限公司 | A kind of for being prepared the catalyst of pyruvate by lactate and preparing the method for pyruvate |
| CN106927718A (en) * | 2017-04-07 | 2017-07-07 | 佛山市蓝瑞欧特信息服务有限公司 | A kind of antimildew and antibacterial tile grout and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5820441B2 (en) * | 2013-02-25 | 2015-11-24 | 国立大学法人京都大学 | Production method of pyruvic acid from alginic acid |
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Patent Citations (5)
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|---|---|---|---|---|
| JPH099960A (en) * | 1995-07-03 | 1997-01-14 | Gekkeikan Sake Co Ltd | New pyruvic oxidase, its production and analysis of pyruvic acid |
| CN101579625A (en) * | 2008-05-15 | 2009-11-18 | 湖南大学 | Catalyst and reaction process for preparing pyruvic acid by lactic acid in catalytic oxydehydrogenation way |
| CN104276951A (en) * | 2013-07-02 | 2015-01-14 | 中国科学院大连化学物理研究所 | Method for using water phase to catalytically oxidize lactates for preparing pyruvates |
| CN106111173A (en) * | 2016-06-28 | 2016-11-16 | 厦门市净屋环保科技有限公司 | A kind of for being prepared the catalyst of pyruvate by lactate and preparing the method for pyruvate |
| CN106927718A (en) * | 2017-04-07 | 2017-07-07 | 佛山市蓝瑞欧特信息服务有限公司 | A kind of antimildew and antibacterial tile grout and preparation method thereof |
Non-Patent Citations (2)
| Title |
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| Synthesis of pyruvic acid by vapour phase catalytic oxidative dehydrogenation of lactic acid;Lomate S et al.;《Journal of Molecular Catalysis A Chemical》;20130520(第377期);第123-128页 * |
| 乳酸氧气氧化法制备丙酮酸;杨辉琼等;《化学世界》;20020630(第6期);第307-309页 * |
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