CN113845419B - Preparation method of levulinate - Google Patents
Preparation method of levulinate Download PDFInfo
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- CN113845419B CN113845419B CN202111224407.9A CN202111224407A CN113845419B CN 113845419 B CN113845419 B CN 113845419B CN 202111224407 A CN202111224407 A CN 202111224407A CN 113845419 B CN113845419 B CN 113845419B
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- trialkoxymethane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
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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
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
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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
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
- B01J27/19—Molybdenum
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of levulinate, which comprises the following steps: adding a hexasaccharide compound and a catalyst into trialkoxymethane, and generating levulinate under the catalysis of the trialkoxymethane and the catalyst under the conditions of a first preset temperature, a first preset pressure and a first preset length.
Description
Technical Field
The invention relates to a preparation method of chemicals, in particular to a preparation method of levulinate.
Background
The ever-decreasing and global warming of petroleum resources requires the search for a green, environmentally sustainable energy source to reduce reliance on fossil fuels. Levulinate is one of important platform molecules of biomass base, can perform various reactions such as oxidation, reduction, substitution, polymerization, addition and the like, and is an important platform molecule with wide application prospects in industries such as coating, perfume, food, medicine and the like. Short chain fatty acid esters of levulinic acid, because of their very similar nature to biodiesel, can be used as a potential biofuel or fuel additive.
At present, the production method of levulinate mainly comprises four paths: levulinic acid direct esterification, furfuryl alcohol alcoholysis, 5-chloromethyl furfural alcoholysis and saccharide direct alcoholysis. The levulinic acid direct esterification method has mild reaction conditions and higher yield, but the levulinic acid production cost of the method is higher due to the fact that raw levulinic acid is high in price and difficult to purify. The furfuryl alcohol acid alcoholysis method is to hydrogenate furfuryl alcohol to obtain furfuryl alcohol, and the furfuryl alcohol is alcoholyzed to obtain ethyl levulinate under an acidic condition, the method designs multi-step reaction, and the furfuryl alcohol is difficult to purify, and relates to high-pressure hydrogenation, so that the process is complex, the equipment requirement is high, and the development of the path is limited; the raw material 5-chloromethyl furfural of the 5-chloromethyl furfural alcoholysis method needs to participate in concentrated hydrochloric acid in the preparation process, and the yield is lower, so that the equipment corrosion is serious and the atom utilization rate is low; the saccharide compound is directly hydrolyzed, the source of raw materials is wide, the process is simple, and the method is a path which has the development prospect in the production of levulinate at present.
Disclosure of Invention
In view of the above, the present invention provides a method for preparing levulinate ester, so as to solve the above technical problems.
In order to achieve the technical purpose, the invention provides a preparation method of levulinate, which comprises the following steps:
adding a hexasaccharide compound and a catalyst into trialkoxymethane, and generating levulinate under the catalysis of the trialkoxymethane and the catalyst under the conditions of a first preset temperature, a first preset pressure and a first preset length.
According to an embodiment of the present invention, the six-carbon carbohydrate includes at least one of the following: fructose, glucose, maltose, sucrose, microcrystalline cellulose.
According to an embodiment of the present invention, the catalyst includes any one of the following: a catalyst for supporting phosphotungstic acid, a catalyst for supporting phosphomolybdic acid, a catalyst for supporting silicotungstic acid, and a catalyst for supporting silicomolybdic acid.
According to the embodiment of the invention, the carrier of the phosphotungstic acid-loaded catalyst, the carrier of the phosphomolybdic acid-loaded catalyst, the carrier of the silicotungstic acid-loaded catalyst and the carrier of the silicomolybdic acid-loaded catalyst all comprise any one of the following: silica, zirconium dioxide, titanium oxide, activated carbon.
According to an embodiment of the present invention, the trialkoxymethane includes at least one of the following: trimethyl orthoformate and triethyl orthoformate.
According to the embodiment of the invention, the mass ratio of the six-carbon carbohydrate to the trialkoxymethane is 1:5-1:100.
According to an embodiment of the present invention, the mass ratio of the catalyst to the hexose compound is 0.1 to 10.
According to an embodiment of the present invention, the first preset temperature includes 50 to 100 ℃.
According to an embodiment of the present invention, the first preset pressure includes 0.1-5 Mpa.
According to the embodiment of the invention, the first preset time period comprises 1-48 hours.
The invention provides a preparation method of levulinate, which comprises the steps of adding a hexacarbosaccharide compound and a catalyst into trialkoxymethane, reacting the hexacarbosaccharide compound and the trialkoxymethane to generate an intermediate product 5- (methoxymethyl) -2-furfural under the catalysis of the catalyst at a specific temperature and under the specific pressure, and further reacting the intermediate product 5- (methoxymethyl) -2-furfural with the trialkoxymethane to generate the levulinate.
Drawings
Fig. 1 schematically shows a gas chromatogram for detecting methyl levulinate prepared by the invention using gas chromatography.
FIG. 2 schematically shows a nuclear magnetic resonance hydrogen spectrum of levulinate prepared according to the invention.
FIG. 3 schematically shows a nuclear magnetic resonance carbon spectrum of levulinate prepared according to the invention.
Detailed Description
The present invention will be further described in detail below with reference to specific embodiments and with reference to the accompanying drawings, in order to make the objects, technical solutions and advantages of the present invention more apparent.
The synthesis methods of levulinate in the related art mainly comprise a levulinic acid direct esterification method, a furfuryl alcohol acid alcoholysis method and a 5-chloromethyl furfural alcoholysis method, and the three synthesis methods have the problems of high raw material price, difficult purification, high production cost, complex process, high equipment requirement, low product yield, serious equipment corrosion, low atom utilization rate and the like.
The levulinate prepared by the method is easy to separate and purify from a biomass solution, and is a path with development prospect in the current production of levulinate.
Accordingly, the present invention provides a process for the preparation of levulinate esters comprising: adding a hexasaccharide compound and a catalyst into trialkoxymethane, and generating levulinate under the catalysis of the trialkoxymethane and the catalyst under the conditions of a first preset temperature, a first preset pressure and a first preset length.
HC(OCH 3 ) 3 +2H 2 O→HCOOH+3CH 3 OH (1)(1)
In the embodiment of the invention, the hexacarbosaccharide compound and the catalyst are added into the trialkoxymethane, and under the catalysis of the catalyst, the hexacarbosaccharide compound and the trialkoxymethane react to generate an intermediate product 5- (methoxymethyl) -2-furfural, and the intermediate product 5- (methoxymethyl) -2-furfural further reacts with the trialkoxymethane to generate levulinate.
According to the embodiment of the invention, the hexacarbosaccharide compound generates 5- (methoxymethyl) -2-furfural under the catalysis of the trialkoxymethane and the catalyst; the 5- (methoxymethyl) -2-furfural is catalyzed by the trialkoxymethane and the catalyst to produce levulinate.
In the embodiment of the invention, under the catalysis of a catalyst at a first preset temperature and a first preset pressure, the hexacarbosaccharide compound reacts with trialkoxymethane to generate an intermediate product 5- (methoxymethyl) -2-furfural, and then the intermediate product continues to react with the trialkoxymethane to generate levulinate.
According to an embodiment of the present invention, the six-carbon carbohydrate includes at least one of the following: fructose, glucose, maltose, sucrose, microcrystalline cellulose.
In the embodiment of the invention, the hexacarbosaccharide compound is used as a reaction raw material and comprises fructose, glucose, maltose, sucrose and microcrystalline cellulose, the main components of the raw materials are glucose and fructose, the fructose is easy to hydrolyze, and simultaneously, the maltose, the sucrose and the microcrystalline cellulose are used as raw materials with a glucose structure, can be isomerized into the fructose under the action of a catalyst, and the fructose is further hydrolyzed to participate in the next reduction reaction.
According to an embodiment of the present invention, the catalyst includes any one of the following: a catalyst for supporting phosphotungstic acid, a catalyst for supporting phosphomolybdic acid, a catalyst for supporting silicotungstic acid, and a catalyst for supporting silicomolybdic acid.
According to the embodiment of the invention, the carrier of the catalyst for supporting the phosphotungstic acid, the carrier of the catalyst for supporting the silicotungstic acid and the carrier of the catalyst for supporting the silicomolybdic acid all comprise any one of the following: silica, zirconium dioxide, titanium oxide, activated carbon.
In the embodiment of the invention, the catalyst is a base metal-based supported catalyst system, has the advantages of low cost, easy preparation, good cycle performance, long service life, high efficiency, stability, low cost, green and the like, and is used for catalyzing levulinate hydrogenation, and the preparation of gamma-valerolactone is an important current development trend.
According to an embodiment of the present invention, the trialkoxymethane includes any one of the following: trimethyl orthoformate and triethyl orthoformate.
In the embodiment of the invention, the trialkoxymethane is easy to combine with two molecules of water at high temperature to react to generate formic acid and methanol, so that the trialkoxymethane is used as a solvent and an alcohol reagent to participate in the generation of levulinate in the reaction process.
According to the embodiment of the invention, the mass ratio of the six-carbon carbohydrate to the trialkoxymethane is 1:5-1:100.
In the embodiment of the invention, the mass ratio of the six-carbon carbohydrate to the trialkoxymethane comprises 1:5-1:100, for example, 1:5, 1:30, 1:50, 1:80 and 1:100.
According to an embodiment of the present invention, the mass ratio of the catalyst to the hexose compound is 0.1 to 10.
In the embodiment of the present invention, the mass ratio of the catalyst to the hexose compound is 0.1 to 10, for example, 0.1, 5, 8, 10.
According to an embodiment of the present invention, the first preset temperature includes 50 to 100 ℃.
In the embodiment of the present invention, the first preset temperature includes 50 to 100 ℃, for example, 50 ℃, 70 ℃, 85 ℃, 100 ℃.
According to an embodiment of the present invention, the first preset pressure includes 0.1-5 Mpa.
In this embodiment of the present invention, the first preset pressure includes 0.1 to 5Mpa, for example, 0.1Mpa, 1Mpa, 3Mpa, 5Mpa.
According to the embodiment of the invention, the first preset time period comprises 1-48 hours.
In this embodiment of the present invention, the first preset duration includes 1 to 48 hours, for example, 1 hour, 12 hours, 24 hours, 36 hours, 48 hours.
The present invention will be explained in further detail with reference to specific examples.
Example 1
To 30ml of an aqueous solution containing 0.3g of phosphotungstic acid was added 1g of ZrO 2 Stirring and soaking for 3h at room temperature, standing for 24h, evaporating excessive water, drying at 110deg.C for 24h, and calcining at 300deg.C for 3h to obtain phosphotungstic acid-Zirconia catalyst.
Example 2
To 30ml of an aqueous solution containing 0.3g of phosphomolybdic acid was added 1g of TiO 2 Stirring and soaking for 3 hours at room temperature, standing for 24 hours, evaporating excessive water, drying for 24 hours at 110 ℃, and calcining for 3 hours at 300 ℃ to prepare the phosphomolybdic acid/titanium oxide catalyst.
Preparation of levulinate esters
The following examples are implemented in pressure-resistant tubes.
Example 3
Into a 15mL pressure-resistant tube, 0.1g of fructose, 0.1g of phosphomolybdic acid/titanium oxide catalyst and 10mL of trimethyl orthoformate were added, and the mixture was heated to 120℃under magnetic stirring, and reacted for 10 hours under stirring. After the completion of the reaction, the reaction mixture was cooled to room temperature, transferred to a 100ml volumetric flask, diluted with methanol to a constant volume, and then subjected to detection of the product content by assembling DM-WAX (30 m. Times.0.32 mm. Times.0.25 μm) column on a gas chromatograph (GC 2104, shimadzu, FID). The gasification temperature is set at 250 ℃, the detection temperature is set at 280 ℃, and the column box temperature is set at 180 ℃ and kept for 20min. The linear velocity was 45cm/s and the split ratio was 50. And detecting the product by adopting an external standard method. Taking a certain amount of product, diluting the product with methanol, then fixing the volume to 100ml, sampling, carrying out gas phase detection, detecting for three times, and taking an average value. The product yield calculation method is as follows:
the compound of the reaction system is quantitatively detected, and the yield of methyl levulinate is 95%.
Fig. 1 schematically shows a gas chromatogram for detecting methyl levulinate prepared by the invention using gas chromatography.
By examining the retention time of the standard substance, it is known from the retention time shown in FIG. 1 that the gas chromatographic peak at the retention time of 1.35min is the methyl levulinate peak prepared by the reaction, and the gas chromatographic peak at the retention time of 8.28min is the intermediate product 5- (methoxymethyl) -2-furfural peak of the present invention.
Example 4
The specific reaction procedure and detection method were the same as in example 3, except that the organic solvent was changed to 5 mL. As a result, methyl levulinate was obtained in 92% yield.
Example 5
The specific reaction procedure was the same as in example 3, except that fructose was changed to glucose. The resulting product was methyl levulinate with a yield of 72%.
Example 6
The specific reaction procedure was the same as in example 3, except that fructose was changed to glucose. As a result, methyl levulinate was obtained in a yield of 70%.
Example 7
The specific reaction procedure was the same as in example 3, except that the phosphomolybdic acid/titanium oxide catalyst was changed to phosphotungstic acid/titanium oxide. As a result, methyl levulinate was obtained as the product, and the yield was 90%.
Example 8
The specific reaction procedure was the same as in example 3, except that the phosphomolybdic acid/titanium oxide catalyst was changed to phosphotungstic acid/titanium oxide. As a result, methyl levulinate was obtained, and the yield was 84%.
Example 9
The specific reaction procedure and the detection method were the same as in example 3, except that the reaction temperature was adjusted to 100 ℃. As a result, methyl levulinate was obtained in a yield of 81%.
Example 10
The specific reaction procedure and the detection method were the same as in example 3, except that the reaction temperature was adjusted to 140 ℃. The resulting product was methyl levulinate with a yield of 88%.
Example 11
The specific reaction procedure and the detection method were the same as in example 3, except that the reaction solvent was changed to triethyl orthoformate. The product obtained as a result was ethyl levulinate, and the yield was 76%.
Example 12
The specific reaction procedure and detection method were the same as in example 3, except that the reaction time was changed to 24 hours. As a result, methyl levulinate was obtained, and the yield was 93%.
The foregoing description of the embodiments has been provided for the purpose of illustrating the general principles of the invention, and is not meant to limit the invention thereto, but to limit the invention thereto, and any modifications, equivalents, improvements and equivalents thereof may be made without departing from the spirit and principles of the invention.
Claims (4)
1. A method for preparing methyl levulinate, comprising:
adding a six-carbon carbohydrate and a catalyst into trimethyl orthoformate, and generating methyl levulinate under the catalysis of the trimethyl orthoformate and the catalyst at a first preset temperature, a first preset pressure and a first preset time period;
wherein the six-carbon carbohydrate comprises at least one of the following: fructose, glucose, maltose, sucrose;
the catalyst is any one of the following: a phosphotungstic acid-supported catalyst and a phosphomolybdic acid-supported catalyst;
the first preset temperature is 120 ℃, and the first preset time period is 10-24 hours;
the carrier of the phosphotungstic acid-loaded catalyst and the carrier of the phosphomolybdic acid-loaded catalyst are titanium oxide.
2. The method for producing methyl levulinate according to claim 1, wherein a mass ratio of the six-carbon saccharide compound to the trimethyl orthoformate is 1:5 to 1:100.
3. The method for producing levulinate according to claim 1, wherein a mass ratio of the catalyst to the hexose compound is 0.1 to 10.
4. The method for producing methyl levulinate according to claim 1, wherein the first preset pressure comprises 0.1-5 Mpa.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3621517A1 (en) * | 1986-06-27 | 1988-01-07 | Klaus Dipl Chem Dr Garves | Synthesis of alkoxymethylfurfurals and alkyl levulinates from cellulose or lignocelluloses or starch and alcohols |
| CN1643116A (en) * | 2002-04-01 | 2005-07-20 | 纳幕尔杜邦公司 | Preparation of levulinic acid esters and formic acid esters from biomass and olefins |
| CN107162899A (en) * | 2017-05-22 | 2017-09-15 | 中国农业大学 | A kind of microwave radiation technology phosphotungstic acid or and its salt catalysis biomass carbohydrate alcoholysis synthesis of acetyl propionic ester method |
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| US11498892B2 (en) * | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3621517A1 (en) * | 1986-06-27 | 1988-01-07 | Klaus Dipl Chem Dr Garves | Synthesis of alkoxymethylfurfurals and alkyl levulinates from cellulose or lignocelluloses or starch and alcohols |
| CN1643116A (en) * | 2002-04-01 | 2005-07-20 | 纳幕尔杜邦公司 | Preparation of levulinic acid esters and formic acid esters from biomass and olefins |
| CN107162899A (en) * | 2017-05-22 | 2017-09-15 | 中国农业大学 | A kind of microwave radiation technology phosphotungstic acid or and its salt catalysis biomass carbohydrate alcoholysis synthesis of acetyl propionic ester method |
Non-Patent Citations (2)
| Title |
|---|
| Patricia Fontes Pinheiro等."One-pot synthesis of alkyl levulinates from biomass derivative carbohydrates in tin(II) exchanged silicotungstates-catalyzed reactions".Cellulose.2019,第26卷(第13-14期),第7953-7969页. * |
| 吴世敏等.《简明精细化工大辞典》.辽宁科学技术出版社,1999,(第1版),第573页. * |
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