CN113896699A - Preparation method of gamma-valerolactone - Google Patents
Preparation method of gamma-valerolactone Download PDFInfo
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- CN113896699A CN113896699A CN202111224421.9A CN202111224421A CN113896699A CN 113896699 A CN113896699 A CN 113896699A CN 202111224421 A CN202111224421 A CN 202111224421A CN 113896699 A CN113896699 A CN 113896699A
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- 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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
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- C07C67/00—Preparation of carboxylic acid esters
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Abstract
The invention discloses a preparation method of gamma-valerolactone, which comprises the following steps: adding a hexose compound and a catalyst into trialkoxymethane, and generating methyl levulinate by the hexose compound under the catalysis of the catalyst at a first preset temperature, a first preset pressure and a first preset length; trialkoxymethane generates hydrogen at a first preset temperature; the methyl levulinate is reduced in situ to gamma-valerolactone under the action of a catalyst and hydrogen.
Description
Technical Field
The invention relates to a preparation method of chemicals, in particular to a preparation method of gamma-valerolactone.
Background
The gradual depletion of traditional non-renewable resources such as coal, petroleum, natural gas and the like promotes the vigorous development of biological energy technology, biomass is used as a unique renewable carbon resource and can be converted into an important biomass platform molecule of a biofuel gamma-valerolactone through catalysis, the biomass platform molecule can be used in the industrial fields such as edible spices and the like, and simultaneously is a novel biological energy with great potential, and the biomass platform molecule is more suitable to be used as a fuel additive compared with fuels such as ethanol and methanol. Engine experiments with 15% gamma-valerolactone blend oil (petroleum and gamma-valerolactone) show that the addition of gamma-valerolactone has no adverse effect on the engine, and the tail gas emission of carbon monoxide and particles is reduced while the fuel octane number is improved.
The gamma-valerolactone is prepared from levulinic acid, and because the levulinic acid serving as a raw material has the characteristics of high boiling point and low vapor pressure, the gamma-valerolactone is difficult to separate from biomass hydrolysate, therefore, the energy consumption and the cost of the separation process are improved, most of the existing levulinate catalytic hydrogenation systems have the defects of using precious metal catalysts, using organic alcohol solvents, poor catalyst cycle performance, complex catalyst preparation process, high overall reaction process cost and the like, however, the gamma-valerolactone serving as a novel energy compound with great development potential requires the characteristics of cheap and easily prepared catalysts, good cycle performance and long service life, and the development of the supported catalyst system based on base metals and having the advantages of high efficiency, stability, low cost, greenness and the like, the preparation of gamma-valerolactone by catalytic hydrogenation of levulinate is currently an important development trend.
Disclosure of Invention
In view of the above, the present invention provides a method for preparing gamma-valerolactone, which is intended to at least partially solve the above technical problems.
In order to achieve the technical purpose, the invention provides a preparation method of gamma-valerolactone, which comprises the following steps: adding a hexose compound and a catalyst into trialkoxymethane, and generating methyl levulinate from the hexose compound under the catalysis of the catalyst at a first preset temperature, a first preset pressure and a first preset length; said trialkoxymethane generating hydrogen at said first predetermined temperature;
and the methyl levulinate is reduced into gamma-valerolactone in situ under the action of the catalyst and the hydrogen.
According to an embodiment of the present invention, the six-carbon sugar compound includes at least one of the following: fructose, sucrose.
According to an embodiment of the present invention, the catalyst includes any one of the following: a catalyst loaded with phosphotungstic acid, a catalyst loaded with phosphomolybdic acid and a catalyst loaded with silicotungstic acid.
According to an embodiment of the present invention, the carrier of the phosphotungstic acid-supported catalyst, the carrier of the phosphomolybdic acid-supported catalyst, and the carrier of the silicotungstic acid-supported catalyst each include any one of: silicon dioxide, zirconium dioxide and titanium oxide.
According to an embodiment of the present invention, wherein the trialkoxymethane comprises at least one of: trimethyl orthoformate, triethyl orthoformate.
According to the embodiment of the invention, the mass ratio of the six-carbon sugar compound to the trialkoxymethane is 1: 20-1: 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 predetermined temperature is 180 to 220 ℃.
According to an embodiment of the present invention, the first predetermined pressure is 0.1 to 5 Mpa.
According to an embodiment of the present invention, the first preset time period includes 1 to 48 hours.
The invention provides a preparation method of gamma-valerolactone, which is characterized in that a hexose compound and a catalyst are added into trialkoxymethane, the hexose compound generates methyl levulinate under the catalytic action of the catalyst at high temperature, the trialkoxymethane generates hydrogen at high temperature, and then the methyl levulinate is reduced in situ into the gamma-valerolactone under the action of the hydrogen and the catalyst.
Drawings
Fig. 1 schematically shows a gas chromatogram for detecting gamma-valerolactone prepared according to the invention by means of gas chromatography.
Figure 2 schematically shows the nmr hydrogen spectrum of gamma valerolactone prepared according to the invention.
Figure 3 schematically shows the nmr carbon spectrum of gamma valerolactone prepared according to the invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments.
The gamma-valerolactone prepared by levulinic acid in the related art is difficult to separate from the biomass hydrolysis solution, and the separation energy consumption cost is high.
The vapor pressure of the levulinic acid ester obtained by alcoholysis is more than 10 times of that of levulinic acid due to the hydrophobicity of the levulinic acid ester, the levulinic acid ester is easy to separate, the levulinic acid ester obtained by alcoholysis has the characteristic of hydrophobicity, and the prepared gamma-valerolactone is easy to separate from a biomass hydrolysis solution and has obvious advantages compared with the gamma-valerolactone prepared by levulinic acid.
Accordingly, the present invention provides a method for preparing gamma-valerolactone, comprising: adding a hexose compound and a catalyst into trialkoxymethane, and generating methyl levulinate from the hexose compound under the catalysis of the catalyst at a first preset temperature, a first preset pressure and a first preset length; said trialkoxymethane generating hydrogen at said first predetermined temperature; and the methyl levulinate is reduced into gamma-valerolactone in situ under the action of the catalyst and the hydrogen.
In the embodiment of the invention, a hexose compound and a catalyst are added into trialkoxymethane, the hexose compound generates methyl levulinate under the catalytic action of the catalyst at high temperature, the trialkoxymethane combines with 3 molecules of water at high temperature to generate methyl formate and hydrogen, the methyl formate combines with 2 molecules of water at high temperature to generate formic acid and methanol, the formic acid is decomposed into hydrogen and carbon dioxide at high temperature, and then the methyl levulinate is reduced in situ to gamma-valerolactone under the action of the hydrogen and the catalyst.
In an embodiment of the present invention, the trialkoxymethane generates methyl formate at the first predetermined temperature; generating formic acid and methanol from the methyl formate at the first preset temperature; the formic acid generates hydrogen and carbon dioxide at the first predetermined temperature.
In the embodiment of the invention, trialkoxymethane is used as a solvent and is also used as an alcohol reagent in the reaction process to participate in the generation reaction of methyl levulinate, methyl formate is obtained by the reaction of trialkoxymethane at high temperature, the methyl formate is further decomposed to produce hydrogen as a product at high temperature, and the hydrogen is used as an in-situ hydrogen source to participate in the subsequent hydrogenation reaction to generate gamma-valerolactone.
According to an embodiment of the present invention, the six-carbon sugar compound includes at least one of the following: fructose, sucrose.
In the embodiment of the invention, the hexose compound is mainly selected as fructose, the molecular structure of the fructose is simple and easy to convert, the hydrolysis is easy, the reaction is simpler, and the next reduction reaction is facilitated.
According to an embodiment of the present invention, the catalyst includes any one of the following: a catalyst loaded with phosphotungstic acid, a catalyst loaded with phosphomolybdic acid and a catalyst loaded with silicotungstic acid.
According to an embodiment of the present invention, the carrier of the phosphotungstic acid-supported catalyst, the carrier of the phosphomolybdic acid-supported catalyst, and the carrier of the silicotungstic acid-supported catalyst each include any one of: silicon dioxide, zirconium dioxide and titanium oxide.
In the embodiment of the invention, the catalyst is a base metal-based supported catalyst system, has the advantages of low price, easiness in preparation, good cycle performance, long service life, high efficiency, stability, low cost, greenness and the like, and is used for catalyzing the hydrogenation of levulinate to prepare gamma-valerolactone, which is an important development trend at present.
According to an embodiment of the present invention, wherein the trialkoxymethane comprises any one of: trimethyl orthoformate, triethyl orthoformate.
According to the embodiment of the invention, the mass ratio of the six-carbon sugar compound to the trialkoxymethane is 1: 20-1: 100.
In an embodiment of the present invention, the mass ratio of the six-carbon sugar compound to the trialkoxymethane is 1:20 to 1:100, for example, 1:20, 1:40, 1:70, 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, 3, 6, 10.
According to an embodiment of the present invention, the first predetermined temperature is 180 to 220 ℃.
In an embodiment of the invention, the first predetermined temperature includes 180-220 ℃, for example, 180 ℃, 200 ℃, 210 ℃, 220 ℃.
In the embodiment of the invention, at a first preset temperature, a hexose compound generates methyl levulinate under the catalysis of a catalyst; decomposing trialkoxy methane at a first preset temperature to generate hydrogen; and at a first preset temperature, reducing methyl levulinate in situ into gamma-valerolactone under the action of a catalyst and hydrogen.
According to an embodiment of the present invention, the first predetermined pressure is 0.1 to 5 Mpa.
In an embodiment of the invention, the first predetermined pressure includes 0.1 to 5Mpa, for example, 0.1Mpa, 1Mpa, 3Mpa, 5 Mpa.
According to an embodiment of the present invention, the first preset time period includes 1 to 48 hours.
In an embodiment of the invention, the first preset time period includes 1 to 48 hours, for example, 1 hour, 10 hours, 18 hours, and 24 hours.
The present invention will be described in detail with reference to specific examples.
Example 1
To 30ml of an aqueous solution containing 0.3g of phosphotungstic acid was added 1g of ZrO2Stirring and dipping for 3h at room temperature, standing for 24h, evaporating redundant water, drying for 24h at 110 ℃, and then calcining for 3h at 300 ℃ to prepare the phosphotungstic acid/zirconium oxide catalyst.
Example 2
To 30ml of an aqueous solution containing 0.3g of phosphomolybdic acid, 1g of TiO was added2Stirring and immersing for 3h at room temperature, standing for 24h, evaporating excessive water, drying for 24h at 110 ℃, and then calcining for 3h at 300 ℃ to prepare the phosphomolybdic acid/titanium oxide catalyst.
Preparation of gamma-valerolactone
The following examples were implemented in pressure resistant tubing.
Example 3
0.1g of fructose, 0.1g of phosphomolybdic acid/zirconium oxide catalyst and 10mL of trimethyl orthoformate were put into a 15mL pressure-resistant tube, heated to 180 ℃ under magnetic stirring, and reacted for 15 hours with stirring. After the reaction, the reaction solution was cooled to room temperature, and transferred to a 100ml volumetric flask, and after diluting with methanol to a constant volume, the product content was measured by gas chromatography (GC (2104, Shimazu, FID) equipped with a DM-WAX (30 m. times.0.32 mm. times.0.25 μm) column, the gasification temperature was set at 250 ℃, the measurement temperature was set at 280 ℃, the column box temperature was set at 180 ℃, the reaction solution was maintained for 20min, the linear velocity was 45cm/s, and the split ratio was 50.
And (3) detecting the product by adopting an external standard method, diluting a certain amount of the product with methanol, then fixing the volume to 100ml, sampling, carrying out gas phase detection for three times, and taking an average value. The product yield calculation method is as follows:
the compound in the reaction system is quantitatively detected, and the yield of the gamma-valerolactone is 82 percent.
Fig. 1 schematically shows a gas chromatogram for detecting gamma-valerolactone prepared according to the invention by means of gas chromatography.
By referring to the retention time of the standard substance, as can be seen from the retention time shown in fig. 1, the gas chromatography peak at the retention time of 1.35min is the solvent peak in the reaction system, and the gas chromatography peak at the retention time of 3.1min is the gamma-valerolactone peak prepared by the present invention.
Example 4
The specific reaction process and detection method were the same as in example 3 except that 15mL of the organic solvent was used instead. The product obtained as a result was gamma valerolactone and the yield was 86%.
Example 5
The specific reaction procedure and detection method were the same as in example 3 except that 0.1g of fructose was changed to 0.2g of fructose. As a result, the product obtained was γ -valerolactone, and the yield was 79%.
Example 6
The specific reaction procedure and detection method were the same as in example 3 except that 0.1g of fructose was changed to 0.2g of fructose. As a result, the product obtained was γ -valerolactone, and the yield was 87%.
Example 7
The specific reaction process and detection method were the same as in example 3 except that the phosphomolybdic acid/zirconia catalyst was changed to phosphotungstic acid/zirconia. As a result, the product obtained was γ -valerolactone, and the yield was 81%.
Example 8
The specific reaction process and detection method were the same as in example 3 except that the phosphomolybdic acid/zirconia catalyst was changed to phosphotungstic acid/titania. As a result, the product obtained was γ -valerolactone, and the yield was 80%.
Example 9
The specific reaction process and detection method were the same as in example 3 except that the reaction temperature was adjusted to 200 ℃. The product obtained as a result was gamma valerolactone and the yield was 74%.
Example 10
The specific reaction process and detection method were the same as in example 3 except that the reaction temperature was adjusted to 190 ℃. The product obtained as a result was gamma valerolactone and the yield was 76%.
Example 11
The specific reaction process and 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 gamma valerolactone and the yield was 76%.
Example 12
The specific reaction process and detection method are the same as in example 3, except that the reaction time is changed to 24 h. The product obtained as a result was gamma valerolactone and the yield was 88%.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of gamma-valerolactone comprises the following steps:
adding a hexose compound and a catalyst into trialkoxymethane, and generating methyl levulinate from the hexose compound under the catalytic action of the catalyst at a first preset temperature, a first preset pressure and a first preset length; the trialkoxymethane is generated into hydrogen at the first preset temperature;
and the methyl levulinate is reduced to gamma-valerolactone in situ under the action of the catalyst and the hydrogen.
2. The method of producing γ -valerolactone according to claim 1, wherein the six-carbon sugar compound comprises at least one of: fructose, sucrose.
3. The method of producing γ -valerolactone according to claim 1, wherein the catalyst comprises any one of: a catalyst loaded with phosphotungstic acid, a catalyst loaded with phosphomolybdic acid and a catalyst loaded with silicotungstic acid.
4. The gamma-valerolactone preparation method according to claim 3, wherein the support of the phosphotungstic acid-supported catalyst, the support of the phosphomolybdic acid-supported catalyst, the support of the silicotungstic acid-supported catalyst each comprise any one of: silicon dioxide, zirconium dioxide and titanium oxide.
5. The method of producing γ -valerolactone according to claim 1, wherein the trialkoxymethane comprises any one of: trimethyl orthoformate, triethyl orthoformate.
6. The method for producing γ -valerolactone according to claim 1, wherein the mass ratio of the hexose compound to trialkoxymethane comprises 1:20 to 1: 100.
7. The method for producing γ -valerolactone according to claim 1, wherein the mass ratio of the catalyst to the hexose compound is from 0.1 to 10.
8. The method of producing gamma valerolactone according to claim 1, wherein the first predetermined temperature comprises from 180 ℃ to 220 ℃.
9. The method of preparing gamma-valerolactone according to claim 1, wherein the first predetermined pressure comprises 0.1 to 5 Mpa.
10. The method for preparing gamma valerolactone according to claim 1, wherein the first predetermined period of time comprises 1 to 48 hours.
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| CN104829559A (en) * | 2015-05-29 | 2015-08-12 | 厦门大学 | Method of preparing Nu-valerolactone from methyl levulinate |
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| JP2015145355A (en) * | 2014-02-04 | 2015-08-13 | 国立研究開発法人産業技術総合研究所 | METHOD FOR PRODUCING γ-VALEROLACTONE |
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