CN106111173B - A kind of method for preparing pyruvate - Google Patents
A kind of method for preparing pyruvate Download PDFInfo
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- CN106111173B CN106111173B CN201610489910.XA CN201610489910A CN106111173B CN 106111173 B CN106111173 B CN 106111173B CN 201610489910 A CN201610489910 A CN 201610489910A CN 106111173 B CN106111173 B CN 106111173B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses a kind of method for preparing pyruvate：The catalyst is selected from more than one or both of cementite, zirconium carbide, vanadium carbide, ferric phosphate, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate, the present invention is using lactate as raw material, oxygen or air are oxidant, under above-mentioned catalyst action, pyruvate is prepared by catalytic oxidation；The catalytic reaction can be carried out in atmospheric conditions, and can not need solvent, product yield high, and catalyst is recyclable to be reused.
Description
Technical field
The present invention relates to the preparation of pyruvate, and in particular to a kind of catalyst for being used to prepare pyruvate by lactate
And the method for preparing pyruvate.
Background technology
Pyruvate is a kind of important fine chemicals and chemical intermediate, is widely used in medicine, food, agricultural chemicals, change
The industries such as cosmetic.
The route of current synthesizing pyruvate has a variety of, such as tartrate conversion method, this method prepares pyruvate
Yield is low, and cost is high, and environmental pollution is serious.It is most directly effective approach, breast to prepare pyruvate by lactate oxidation
The method that acid esters prepares pyruvate mainly has lactate vapour phase oxidation process and lactate liquid phase oxidation；Wherein, lactate gas
The reaction temperature of phase oxidation is higher, requirement to equipment is high, production cost is high；Lactate liquid phase oxidation mainly uses Gao Meng
The oxidants such as sour potassium are aoxidized, and this method is seriously polluted, and oxidation efficiency is low.Have been reported that and use loaded noble metal catalyst,
Oxygen is oxidant, and water is solvent, and lactate catalyzing oxidation prepares pyruvate, and this method uses noble metal catalyst, cost
Height, and catalyst preparation process is complicated, the cycle is long.
The content of the invention
In order to solve the above problems, the method that lactate prepares pyruvate, this method are catalyzed the invention provides a kind of
Using air or oxygen as oxygen source, it can carry out in atmospheric conditions, reaction condition is gentle, and it is anti-without solvent or in aqueous solvent
Should, the reaction is heterogeneous catalytic reaction, and catalyst is recyclable to be recycled.
To achieve these goals, technical scheme is as follows：
A kind of catalyst for being used to prepare pyruvate by lactate, the catalyst is selected from cementite, zirconium carbide, carbonization
It is more than one or both of vanadium, ferric phosphate, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate.
The catalyst can be loaded catalyst, and the carrier of the loaded catalyst is selected from SiO2、Al2O3、TiO2、
It is more than one or both of molecular sieve, kaolin, activated carbon, CNT, graphene.
It is a kind of to use a kind of catalyst preparation pyruvate for being used to prepare pyruvate by lactate as described above
Method：This method is using molecular oxygen as oxidant, in the presence of the catalyst, is that raw material passes through catalysis oxidation by lactate
Reaction prepares pyruvate.
Further, the consumption of the catalyst is the 0.001-20.0mol% of raw milk acid esters.
Further, the raw milk acid esters is selected from methyl lactate, ethyl lactate, lactic acid n-propyl ester, isopropyl lactate, breast
One or more in the secondary butyl ester of acid butyl ester, isobutyl lactate, lactic acid.
Further, oxidant used is air or oxygen, and offering oxygen way is atmospheric bubbling.
Further, oxidant used is air or oxygen, and offering oxygen way is high pressure voltage supply, and pressure value is 0.01-5MPa.
Further, the method for preparing pyruvate is carried out without solvent or in aqueous solvent.
Further, the flow velocity of air or oxygen is 0.01-1000 liters/m of material/minute in the atmospheric bubbling.
Further, the reaction temperature for preparing pyruvate is 50-200 DEG C.
Technical scheme of the present invention is relative to prior art, the beneficial effect of acquirement：
(1) catalyst that the present invention is used is cheap non-precious metal catalyst, and cost is relatively low, and the reaction can be in normal pressure
Under the conditions of carry out, requirement to consersion unit is than relatively low, and on the other hand, using oxygen or air as oxidant, reaction condition is gentle,
And product yield high.
(2) reaction that lactate of the present invention prepares pyruvate is heterogeneous catalytic reaction, and catalyst can be reclaimed again
Utilize, in addition, the catalytic reaction is not required to solvent or using water as solvent, reaction condition is gentle, and the waste of generation is few, energy-conserving and environment-protective.
Embodiment
In order that technical problems, technical solutions and advantages to be solved are clearer, clear, tie below
Embodiment is closed, the present invention will be described in further detail.It should be appreciated that specific embodiment described herein is only to explain
The present invention, is not intended to limit the present invention.
A kind of catalyst for being used to prepare pyruvate by lactate of the present invention, the catalyst is selected from carbonization
It is more than one or both of iron, zirconium carbide, vanadium carbide, ferric phosphate, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate.
The catalyst can be loaded catalyst, and the carrier of the loaded catalyst is selected from SiO2、Al2O3、TiO2、
It is more than one or both of molecular sieve, kaolin, activated carbon, CNT, graphene.
Loaded catalyst of the present invention, carrier is selected from SiO2、Al2O3、TiO2, molecular sieve, kaolin, activated carbon,
More than one or both of CNT, graphene, the preparation method of the loaded catalyst is polishing or ball-milling method, is urged
Agent load capacity is 5-15%.
It is a kind of to use a kind of catalyst preparation pyruvate for being used to prepare pyruvate by lactate as described above
Method：This method is using molecular oxygen as oxidant, in the presence of the catalyst, is that raw material passes through catalysis oxidation by lactate
Reaction prepares pyruvate；The consumption of the catalyst is the 0.001-20.0mol% of raw milk acid esters；The raw milk acid esters
In methyl lactate, ethyl lactate, lactic acid n-propyl ester, isopropyl lactate, butyl lactate, isobutyl lactate, the secondary butyl ester of lactic acid
One or more.
Specifically, oxidant used is air or oxygen, and offering oxygen way is atmospheric bubbling or high pressure voltage supply；The normal pressure drum
The flow velocity of air or oxygen is 0.01-1000 liters/m of material/minute in bubble；The pressure value of high pressure is 0.01-5MPa.
Specifically, the method for preparing pyruvate is carried out without solvent or in aqueous solvent.
Enter more specifically, the reaction temperature for preparing pyruvate is 50-200 DEG C.
Embodiment one：
Ethyl lactate 1mol is added into normal-pressure reaction kettle, cementite 0.00001mol is added, sky is passed through into reactor
Gas, air velocity is 0.01 liter/m of material/minute, and reactor is heated into 50 DEG C, after reacting 6 hours, cooling discharging,
Reclaimed after catalyst filtration to reuse, product passes through efficient liquid phase chromatographic analysis.Reaction result：Lactic acid ester conversion rate is
92.5%, pyruvate yield is 90.7%.
Embodiment two：
Methyl lactate 1mol is added into normal-pressure reaction kettle, SiO is added2Support type carbonization vanadium catalyst, vanadium carbide mole
Measure as 0.2mol, load capacity is 5%, oxygen is passed through into reactor, oxygen gas flow rate is 1 liter/m of material/minute, will be anti-
Kettle is answered to be heated to 120 DEG C, after reaction 2 hours, cooling discharging is reclaimed to reuse after catalyst filtration, product passes through efficient
Liquid-phase chromatographic analysis.Reaction result：Lactic acid ester conversion rate is 91.2%, and pyruvate yield is 90.3%.
Embodiment three：
Butyl lactate 1mol is added into normal-pressure reaction kettle, zirconium carbide 0.0001mol is added, oxygen is passed through into reactor
Gas, oxygen gas flow rate is 10 liters/m of material/minutes, and reactor is heated into 60 DEG C, and after reacting 12 hours, cooling discharging is urged
Reclaimed after agent filtering to reuse, product passes through efficient liquid phase chromatographic analysis.Reaction result：Lactic acid ester conversion rate is
95.2%, pyruvate yield is 92.3%.
Example IV：
Propyl lactate 1mol is added into normal-pressure reaction kettle, water 0.1mol is added, vanadyl phosphate 0.1mol is added, to reaction
Air is passed through in kettle, air velocity is 1000 liters/m of material/minutes, and reactor is heated into 200 DEG C, reacted 5 hours
Afterwards, cooling discharging, product passes through efficient liquid phase chromatographic analysis.Reaction result：Lactic acid ester conversion rate is 96.0%, and pyruvate is received
Rate is 92.5%.
Embodiment five：
Ethyl lactate 1mol is added into autoclave, ferric phosphate 0.005mol is added, oxygen is passed through into reactor,
Oxygen pressure is 0.01MPa, and reactor is heated into 100 DEG C, after reaction 8 hours, cooling discharging, reclaimed after catalyst filtration with
Reuse, product passes through efficient liquid phase chromatographic analysis.Reaction result：Lactic acid ester conversion rate is 92.0%, pyruvate yield
For 90.5%.
Embodiment six：
Isopropyl lactate 1mol is added into autoclave, water 0.1mol is added, Al is added2O3Load zirconium phosphate oxygen is urged
Agent, zirconium phosphate oxygen mole 0.01mol, load capacity is 10%, air is passed through into reactor, air pressure is 5MPa, will
Reactor is heated to 60 DEG C, and after reacting 10 hours, cooling discharging, product passes through efficient liquid phase chromatographic analysis.Reaction result：Lactic acid
Ester conversion rate is 95.0%, and pyruvate yield is 91.5%.
Embodiment seven：
Isobutyl lactate 1mol is added into normal-pressure reaction kettle, phosphoric acid oxygen copper catalyst, phosphoric acid oxygen amount of copper is added
0.02mol, oxygen is passed through into reactor, and oxygen gas flow rate is 10 liters/m of material/minutes, and reactor is heated into 150
DEG C, after reaction 20 hours, cooling discharging is reclaimed after catalyst filtration to reuse, product passes through efficient liquid phase chromatographic analysis.
Reaction result：Lactic acid ester conversion rate is 92.3%, and pyruvate yield is 93.0%.
Embodiment eight：
Ethyl lactate 1mol is added into autoclave, activated carbon supported vanadyl phosphate catalyst, vanadyl phosphate is added
0.005mol is measured, load capacity is 15%, and oxygen is passed through into autoclave, and oxygen pressure is 2MPa, and reactor is heated to
100 DEG C, after reaction 5 hours, cooling discharging is reclaimed after catalyst filtration to reuse, product passes through high performance liquid chromatography point
Analysis.Reaction result：Lactic acid ester conversion rate is 96.0%, and pyruvate yield is 95.8%.
Comparative example one：
Isobutyl lactate 1mol is added into normal-pressure reaction kettle, activated carbon supported palladium catalyst is added, palladium load capacity is
0.02mol, load capacity 5% is passed through oxygen into reactor, oxygen gas flow rate is 10 liters/m of material/minutes, by reactor
150 DEG C are heated to, after reacting 20 hours, cooling discharging, product passes through efficient liquid phase chromatographic analysis.Reaction result：Lactate turns
Rate is 65.2%, and pyruvate yield is 60.3%.
Comparative example two：
Ethyl lactate 1mol is added into autoclave, activated carbon supported platinum catalyst is added, platinum load capacity is
0.005mol, load capacity 15% is passed through oxygen into autoclave, and oxygen pressure is 2MPa, and reactor is heated into 100
DEG C, after reacting 5 hours, cooling discharging, product passes through efficient liquid phase chromatographic analysis.Reaction result：Lactic acid ester conversion rate is
73.2%, pyruvate yield is 65.8%.
Compared by the experimental data of embodiment and comparative example, it is known that, lactic acid ester conversion rate and pyruvate of the present invention
Yield has the raising of conspicuousness.
The catalyst that the present invention is used is cheap non-precious metal catalyst, and cost is relatively low, and the reaction can be in normal pressure bar
Carried out under part, the requirement to consersion unit is than relatively low, another aspect, using oxygen or air as oxidant, and reaction condition is gentle, and
Product yield high.
The reaction that lactate of the present invention prepares pyruvate is heterogeneous catalytic reaction, and catalyst can reclaim profit again
With in addition, the catalytic reaction is not required to solvent or using water as solvent, reaction condition is gentle, and the waste of generation is few, energy-conserving and environment-protective.
The preferred embodiments of the present invention have shown and described in described above, as previously described, it should be understood that not office of the invention
Be limited to form disclosed herein, be not to be taken as the exclusion to other embodiment, and available for various other combinations, modification and
Environment, and can be changed in invention contemplated scope described herein by the technology or knowledge of above-mentioned teaching or association area
It is dynamic., then all should be appended by the present invention and the change and change that those skilled in the art are carried out do not depart from the spirit and scope of the present invention
In scope of the claims.
Claims (4)
1. a kind of method for preparing pyruvate, it is characterised in that：This method is using molecular oxygen as oxidant, in the effect of catalyst
Under, it is that raw material prepares pyruvate by catalytic oxidation by lactate；The catalyst is selected from cementite, zirconium carbide, carbon
Change more than one or both of vanadium, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate；The reaction temperature for preparing pyruvate
For 50-200 DEG C；The consumption of the catalyst is the 0.001-20.0mol% of raw milk acid esters；The raw milk acid esters is selected from breast
One kind in the secondary butyl ester of sour methyl esters, ethyl lactate, lactic acid n-propyl ester, isopropyl lactate, butyl lactate, isobutyl lactate, lactic acid
Or it is a variety of；Oxidant used is air or oxygen, and offering oxygen way is atmospheric bubbling, or high pressure oxygen supply, and pressure value is 0.01-
5MPa。
2. a kind of method for preparing pyruvate as claimed in claim 1, it is characterised in that：The catalyst is urged for support type
Agent, the carrier of the loaded catalyst is selected from SiO2、Al2O3、TiO2, molecular sieve, kaolin, activated carbon, CNT,
It is more than one or both of graphene.
3. a kind of method for preparing pyruvate as claimed in claim 1 or 2, it is characterised in that：It is described to prepare pyruvate
Method carry out without solvent or in aqueous solvent.
4. a kind of method for preparing pyruvate as claimed in claim 3, it is characterised in that：In the atmospheric bubbling air or
The flow velocity of oxygen is 0.01-1000 liters/m of material/minute.
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106622272A (en) * | 2016-11-25 | 2017-05-10 | 南宁市黑晶信息技术有限公司 | Preparation method of composite molecular sieve based catalyst used for synthesis of pyruvate |
| CN108440289B (en) * | 2018-04-18 | 2021-04-09 | 西安万德科技有限公司 | Method for preparing pyruvate by water-phase catalytic oxidation of lactate |
| CN108863796B (en) * | 2018-06-12 | 2021-06-11 | 大连理工大学 | Method for preparing pyruvate by liquid-phase catalytic oxidation of lactate |
| CN110183327B (en) * | 2019-06-14 | 2021-04-20 | 大连理工大学 | Method for preparing ketonic acid ester by catalytic oxidation of hydroxy ester |
| CN112479875A (en) * | 2020-12-01 | 2021-03-12 | 厦门大学 | Method for preparing alpha-oxo-carboxylic ester by selective oxidation of alpha-hydroxy-carboxylic ester |
| CN113634252B (en) * | 2021-09-06 | 2023-11-21 | 北京化工大学 | Preparation method of catalyst for preparing pyruvic acid ester by catalyzing lactate to be dehydrogenated |
| CN114591171A (en) * | 2022-03-17 | 2022-06-07 | 苏州仁晟新材料科技有限公司 | Preparation method of pharmaceutical grade ultra-high purity ethyl pyruvate |
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| CN102910675A (en) * | 2011-08-05 | 2013-02-06 | 中国科学院大连化学物理研究所 | Preparation of VO2 nanosheet material and applications thereof |
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| CN1167106A (en) * | 1997-04-10 | 1997-12-10 | 复旦大学 | Method for synthesizing pyruvate by lactate catalyzing |
| CN102910675A (en) * | 2011-08-05 | 2013-02-06 | 中国科学院大连化学物理研究所 | Preparation of VO2 nanosheet material and applications thereof |
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