CN106111173A - A kind of for being prepared the catalyst of pyruvate by lactate and preparing the method for pyruvate - Google Patents
A kind of for being prepared the catalyst of pyruvate by lactate and preparing the method for pyruvate Download PDFInfo
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- CN106111173A CN106111173A CN201610489910.XA CN201610489910A CN106111173A CN 106111173 A CN106111173 A CN 106111173A CN 201610489910 A CN201610489910 A CN 201610489910A CN 106111173 A CN106111173 A CN 106111173A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/22—Carbides
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
- B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
- B01J27/1802—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates
- B01J27/1817—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates with copper, silver or gold
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
- B01J27/1853—Phosphorus; Compounds thereof with iron group metals or platinum group metals with iron, cobalt or nickel
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses a kind of for being prepared the catalyst of pyruvate by lactate and preparing the method for pyruvate: described catalyst is selected from one or more in cementite, zirconium carbide, vanadium carbide, iron phosphate, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate, the present invention is with lactate as raw material, oxygen or air are oxidant, under above-mentioned catalyst action, prepare pyruvate through catalytic oxidation；This catalytic reaction can be carried out in atmospheric conditions, and can need not solvent, and product yield is high, and catalyst is recyclable to be re-used.
Description
Technical field
The present invention relates to the preparation of pyruvate, be specifically related to a kind of catalyst for being prepared pyruvate by lactate
And the method preparing pyruvate.
Background technology
Pyruvate is a kind of important fine chemicals and chemical intermediate, is widely used in medicine, food, pesticide, change
The industries such as cosmetic.
The route of synthesizing pyruvate has multiple at present, and such as tartrate conversion method, the method prepares pyruvate
Yield is low, and cost is high, and environmental pollution is serious.Preparing pyruvate by lactate oxidation is the most effective approach, breast
Acid esters prepares the method for pyruvate mainly lactate vapour phase oxidation process and lactate liquid phase oxidation；Wherein, lactate gas
The reaction temperature of phase oxidation is higher, high to requirement height, the production cost of equipment；Lactate liquid phase oxidation mainly uses Gao Meng
The oxidants such as acid potassium aoxidize, and the method is seriously polluted, and oxidation efficiency is low.Have been reported that employing loaded noble metal catalyst,
Oxygen is oxidant, and water is solvent, and pyruvate is prepared in lactate catalyzing oxidation, and the method uses noble metal catalyst, cost
Height, and catalyst preparation process is complicated, the cycle is long.
Summary of the invention
In order to solve the problems referred to above, the invention provides and a kind of be catalyzed the method that lactate prepares pyruvate, the method
With air or oxygen as oxygen source, can carry out in atmospheric conditions, reaction condition is gentle, and without solvent or in aqueous solvent anti-
Should, this reaction is heterogeneous catalytic reaction, the recyclable recycling of catalyst.
To achieve these goals, technical scheme is as follows:
A kind of catalyst for being prepared pyruvate by lactate, described catalyst is selected from cementite, zirconium carbide, carbonization
One or more in vanadium, iron phosphate, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate.
Described catalyst can be loaded catalyst, and the carrier of described loaded catalyst is selected from SiO2、Al2O3、TiO2、
One or more in molecular sieve, Kaolin, activated carbon, CNT, Graphene.
A kind of a kind of catalyst for being prepared pyruvate by lactate as described above is used to prepare pyruvate
Method: the method is with molecular oxygen as oxidant, under the effect of described catalyst, lactate is raw material through catalysis oxidation
Pyruvate is prepared in reaction.
Further, the consumption of described catalyst is the 0.001-20.0mol% of raw milk acid esters.
Further, described 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 force value is 0.01-5MPa.
Further, the described method preparing pyruvate is carried out without solvent or in aqueous solvent.
Further, in described atmospheric bubbling the flow velocity of air or oxygen be 0.01-1000 liter/m of material/minute.
Further, the described reaction temperature preparing pyruvate is 50-200 DEG C.
Technical scheme of the present invention provides the benefit that relative to prior art, acquirement:
(1) catalyst that the present invention uses is cheap non-precious metal catalyst, and cost is relatively low, and this reaction can be at normal pressure
Under the conditions of carry out, relatively low to the requirement ratio of consersion unit, on the other hand, with oxygen or air as oxidant, reaction condition is gentle,
And product yield is high.
(2) lactate of the present invention prepares the reaction of pyruvate is heterogeneous catalytic reaction, and catalyst can reclaim again
Utilizing, additionally, this catalytic reaction is not required to solvent or with water as solvent, reaction condition is gentle, and the refuse of generation is few, energy-conserving and environment-protective.
Detailed description of the invention
In order to make the technical problem to be solved, technical scheme and beneficial effect clearer, clear, below tie
Close embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein is only in order to explain
The present invention, is not intended to limit the present invention.
A kind of catalyst for being prepared pyruvate by lactate of the present invention, described catalyst is selected from carbonization
One or more in ferrum, zirconium carbide, vanadium carbide, iron phosphate, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate.
Described catalyst can be loaded catalyst, and the carrier of described loaded catalyst is selected from SiO2、Al2O3、TiO2、
One or more in 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,
One or more in CNT, Graphene, the preparation method of this loaded catalyst is polishing or ball-milling method, urges
Agent load capacity is 5-15%.
A kind of a kind of catalyst for being prepared pyruvate by lactate as described above is used to prepare pyruvate
Method: the method is with molecular oxygen as oxidant, under the effect of described catalyst, lactate is raw material through catalysis oxidation
Pyruvate is prepared in reaction；The consumption of described catalyst is the 0.001-20.0mol% of raw milk acid esters；Described 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；Described normal pressure drum
In bubble the flow velocity of air or oxygen be 0.01-1000 liter/m of material/minute；The force value of high pressure is 0.01-5MPa.
Specifically, the described method preparing pyruvate is carried out without solvent or in aqueous solvent.
Enter more specifically, the described reaction temperature preparing pyruvate is 50-200 DEG C.
Embodiment one:
In normal-pressure reaction kettle, add ethyl lactate 1mol, add cementite 0.00001mol, in reactor, be passed through sky
Gas, air velocity be 0.01 liter/m of material/minute, reactor is heated to 50 DEG C, after reacting 6 hours, cooling discharging,
Reclaiming after catalyst filtration to reuse, product passes through efficient liquid phase chromatographic analysis.Reaction result: lactate conversion ratio is
92.5%, pyruvate yield is 90.7%.
Embodiment two:
In normal-pressure reaction kettle, add methyl lactate 1mol, add SiO2Support type carbonization vanadium catalyst, vanadium carbide mole
Amount is for 0.2mol, and load capacity is 5%, is passed through oxygen in reactor, oxygen gas flow rate be 1 liter/m of material/minute, will be anti-
Still is answered to be heated to 120 DEG C, after reacting 2 hours, cooling discharging, reclaim after catalyst filtration to reuse, product is by efficiently
Liquid-phase chromatographic analysis.Reaction result: lactate conversion ratio is 91.2%, pyruvate yield is 90.3%.
Embodiment three:
In normal-pressure reaction kettle, add butyl lactate 1mol, add zirconium carbide 0.0001mol, in reactor, be passed through oxygen
Gas, oxygen gas flow rate be 10 liters/m of materials/minute, reactor is heated to 60 DEG C, after reacting 12 hours, cooling discharging, urge
Agent reclaims to reuse after filtering, and product passes through efficient liquid phase chromatographic analysis.Reaction result: lactate conversion ratio is
95.2%, pyruvate yield is 92.3%.
Embodiment four:
In normal-pressure reaction kettle, add propyl lactate 1mol, add water 0.1mol, add vanadyl phosphate 0.1mol, to reaction
Still is passed through air, air velocity be 1000 liters/m of materials/minute, reactor is heated to 200 DEG C, reacts 5 hours
After, cooling discharging, product passes through efficient liquid phase chromatographic analysis.Reaction result: lactate conversion ratio is 96.0%, pyruvate is received
Rate is 92.5%.
Embodiment five:
In autoclave, add ethyl lactate 1mol, add iron phosphate 0.005mol, in reactor, be passed through oxygen,
Oxygen pressure is 0.01MPa, and reactor is heated to 100 DEG C, after reacting 8 hours, cooling discharging, reclaim after catalyst filtration with
Reusing, product passes through efficient liquid phase chromatographic analysis.Reaction result: lactate conversion ratio is 92.0%, pyruvate yield
It is 90.5%.
Embodiment six:
In autoclave, add isopropyl lactate 1mol, add water 0.1mol, add Al2O3Load zirconium phosphate oxygen is urged
Agent, zirconium phosphate oxygen mole 0.01mol, load capacity is 10%, in reactor, it being passed through air, 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:
In normal-pressure reaction kettle, add isobutyl lactate 1mol, add phosphoric acid oxygen copper catalyst, phosphoric acid oxygen copper amount
0.02mol, is passed through oxygen in reactor, oxygen gas flow rate be 10 liters/m of materials/minute, reactor is heated to 150
DEG C, after reacting 20 hours, cooling discharging, reclaim after catalyst filtration to reuse, product passes through efficient liquid phase chromatographic analysis.
Reaction result: lactate conversion ratio is 92.3%, pyruvate yield is 93.0%.
Embodiment eight:
In autoclave, add ethyl lactate 1mol, add activated carbon supported vanadyl phosphate catalyst, vanadyl phosphate
Amount 0.005mol, load capacity is 15%, is passed through oxygen in autoclave, and oxygen pressure is 2MPa, is heated to by reactor
100 DEG C, after reacting 5 hours, cooling discharging, reclaim after catalyst filtration to reuse, product is divided by high performance liquid chromatography
Analysis.Reaction result: lactate conversion ratio is 96.0%, pyruvate yield is 95.8%.
Comparative example one:
Adding isobutyl lactate 1mol in normal-pressure reaction kettle, add activated carbon supported palladium catalyst, palladium load capacity is
0.02mol, load capacity 5%, in reactor, be passed through oxygen, oxygen gas flow rate be 10 liters/m of materials/minute, by reactor
Being heated to 150 DEG C, 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:
Adding ethyl lactate 1mol in autoclave, add activated carbon supported platinum catalyst, platinum load capacity is
0.005mol, load capacity 15%, in autoclave, it is passed through oxygen, oxygen pressure is 2MPa, and reactor is heated to 100
DEG C, after reacting 5 hours, cooling discharging, product passes through efficient liquid phase chromatographic analysis.Reaction result: lactate conversion ratio is
73.2%, pyruvate yield is 65.8%.
Compared by the experimental data of embodiment and comparative example, it is known that, lactate conversion ratio of the present invention and pyruvate
Yield all has the raising of significance.
The catalyst that the present invention uses is cheap non-precious metal catalyst, and cost is relatively low, and this reaction can be at normal pressure bar
Carrying out under part, relatively low to the requirement ratio of consersion unit, on the other hand, with oxygen or air as oxidant, reaction condition is gentle, and
Product yield is high.
It is heterogeneous catalytic reaction that lactate of the present invention prepares the reaction of pyruvate, and catalyst can reclaim profit again
With, additionally, this catalytic reaction is not required to solvent or with water as solvent, reaction condition is gentle, and the refuse of generation is few, energy-conserving and environment-protective.
Described above illustrate and describes the preferred embodiments of the present invention, as previously mentioned, it should be understood that the present invention not office
Be limited to form disclosed herein, be not to be taken as the eliminating to other embodiments, and can be used for other combinations various, amendment and
Environment, and can be changed by above-mentioned teaching or the technology of association area or knowledge in invention contemplated scope described herein
Dynamic.And the change that those skilled in the art are carried out and change are without departing from the spirit and scope of the present invention, the most all should be appended by the present invention
In scope of the claims.
Claims (10)
1. the catalyst being used for being prepared pyruvate by lactate, it is characterised in that: described catalyst is selected from cementite, carbon
Change in zirconium, vanadium carbide, iron phosphate, phosphoric acid oxygen copper, zirconium phosphate oxygen, vanadyl phosphate one or more.
A kind of catalyst for being prepared pyruvate by lactate, it is characterised in that urge described in:
Agent can be loaded catalyst, and the carrier of described loaded catalyst is selected from SiO2、Al2O3、TiO2, molecular sieve, Kaolin,
One or more in activated carbon, CNT, Graphene.
3. one kind uses a kind of catalyst for being prepared pyruvate by lactate to prepare third
The method of keto ester, it is characterised in that: the method is with molecular oxygen as oxidant, under the effect of described catalyst, by lactate
Pyruvate is prepared through catalytic oxidation for raw material.
A kind of method preparing pyruvate, it is characterised in that: the consumption of described catalyst is former
The 0.001-20.0mol% of material lactate.
A kind of method preparing pyruvate, it is characterised in that: described raw milk acid esters is selected from breast
One in acid methyl ester, ethyl lactate, lactic acid n-propyl ester, isopropyl lactate, butyl lactate, isobutyl lactate, the secondary butyl ester of lactic acid
Or it is multiple.
A kind of method preparing pyruvate, it is characterised in that: oxidant used is air or oxygen
Gas, offering oxygen way is atmospheric bubbling.
A kind of method preparing pyruvate, it is characterised in that: oxidant used is air or oxygen
Gas, offering oxygen way is high pressure voltage supply, and force value is 0.01-5MPa.
A kind of method preparing pyruvate the most as claimed in claims 6 or 7, it is characterised in that: described prepare pyruvate
Method carry out without solvent or in aqueous solvent.
A kind of method preparing pyruvate, it is characterised in that: in described atmospheric bubbling air or
The flow velocity of oxygen be 0.01-1000 liter/m of material/minute.
10. a kind of method preparing pyruvate as described in claim 3,4,5,6,7 or 9, it is characterised in that: described preparation
The reaction temperature of pyruvate is 50-200 DEG C.
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Cited By (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 |
| CN108440289A (en) * | 2018-04-18 | 2018-08-24 | 肖锦 | A kind of method that aqueous catalysis Oxidation of Lactic ester prepares pyruvate |
| CN108863796A (en) * | 2018-06-12 | 2018-11-23 | 大连理工大学 | A kind of method that liquid phase catalytic oxidation lactate prepares pyruvate |
| CN110183327A (en) * | 2019-06-14 | 2019-08-30 | 大连理工大学 | A kind of method that catalysis oxidation hydroxy ester prepares keto 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 |
| CN113634252A (en) * | 2021-09-06 | 2021-11-12 | 北京化工大学 | Preparation method of catalyst for catalyzing lactate dehydrogenation to prepare pyruvate |
| 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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Cited By (11)
| 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 |
| CN108440289A (en) * | 2018-04-18 | 2018-08-24 | 肖锦 | A kind of method that aqueous catalysis Oxidation of Lactic ester prepares 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 |
| CN108863796A (en) * | 2018-06-12 | 2018-11-23 | 大连理工大学 | A kind of method that liquid phase catalytic oxidation lactate prepares pyruvate |
| 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 |
| CN110183327A (en) * | 2019-06-14 | 2019-08-30 | 大连理工大学 | A kind of method that catalysis oxidation hydroxy ester prepares keto ester |
| 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 |
| CN113634252A (en) * | 2021-09-06 | 2021-11-12 | 北京化工大学 | Preparation method of catalyst for catalyzing lactate dehydrogenation to prepare pyruvate |
| 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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| Publication number | Publication date |
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| CN106111173B (en) | 2017-09-01 |
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