CN102372685A - Method for preparing maleic anhydride by catalytic oxidation of 5-hydroxymethylfurfural - Google Patents
Method for preparing maleic anhydride by catalytic oxidation of 5-hydroxymethylfurfural Download PDFInfo
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- CN102372685A CN102372685A CN201010258495XA CN201010258495A CN102372685A CN 102372685 A CN102372685 A CN 102372685A CN 201010258495X A CN201010258495X A CN 201010258495XA CN 201010258495 A CN201010258495 A CN 201010258495A CN 102372685 A CN102372685 A CN 102372685A
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Abstract
The invention relates to a new route for preparing maleic anhydride by catalytic oxidation of 5-hydroxymethylfurfural. According to the new route, air or oxygen is adopted as oxygen source; a vanadium oxide is adopted as a catalyst; the 5-hydroxymethylfurfural is subjected to selective oxidation at a temperature of 60-130 DEG C to obtain the maleic anhydride and the maleic acid. According to the method of the present invention, the biomass resources are adopted as the final raw material sources, the reaction conditions are mild, and the method has great development potential.
Description
Technical field
The present invention relates to and a kind ofly prepare the maleic anhydride method of (comprising the partial hydrolysate toxilic acid) through the catalytic selective oxidation 5 hydroxymethyl furfural.This method is final oxygen source with air or oxygen, and oxyvanadium compound is a catalyzer, at 60-130 ℃, the 5 hydroxymethyl furfural liquid-phase oxidation is obtained maleic anhydride (comprising the partial hydrolysate toxilic acid).
Background technology
Maleic anhydride (MALEIC ANHYDRIDE) is important Organic Chemicals, has important use in industries such as resin, agricultural chemicals, medicine, auxiliary agents at present.Organic industry is used to make fumaric acid and THF etc., also can produce 1,4-butyleneglycol, gamma-butyrolactone, THF, succsinic acid derived product etc.Synthetic resins industry is used to make unsaturated polyester resin, Synolac etc.Pesticide industry is used to make agricultural chemicals phosphothion and higher effective and lower toxic pesticide 4049 etc.2004; Whole world maleic anhydride aggregated capacity has reached 165.0 ten thousand tons/year; Wherein Chinese maleic anhydride aggregated capacity has reached 42.0 ten thousand tons/year, is one of maximum three big acid anhydrides (Tetra hydro Phthalic anhydride, diacetyl oxide, maleic anhydride) of output (Chinese chemical information, 2006 the 1st phases) in the world at present.
As shown in Figure 1: the major industry production route of maleic anhydride and the route that this patent provides.
The production process route of cis-butenedioic anhydride can be divided into 4 kinds of benzene oxidation style, n butane oxidation method, oxygenizement of butene and phthalic anhydride by-product methods etc. by raw material in the industry, and these methods all need be carried out under hot conditions, and energy consumption is bigger, and the over oxidation product is more; Simultaneously reactant concn also receives the restriction (like normal butane content in the n butane oxidation method about 2mol%) of itself and oxygen mixture limits of explosion in the gaseous oxidation.Mainly adopt the n butane oxidation method to produce (Fig. 1) at present in the world, the temperature of reaction of commercial fixed bed device is calculated by the normal butane amount of substance that adds about 400-450 ℃, the maleic anhydride yield be 47-64% (Chem.Rev.1988,88,55-80); On the other hand, along with the mass consumption of the mankind to limited resources such as oil and gas, exploitation is that the maleic anhydride new synthesis process of raw material has very big development potentiality with the renewable resources.The 5 hydroxymethyl furfural that obtains through the glucide dehydration is the important hardware and software platform compound in the biorefinery, causes extensive attention (Angew.Chem.Int.Ed.2007,46,7164-7183 both domestic and external in recent years; Chem.Rev.2007,107,2411-2502).Up to the present, do not see with the 5 hydroxymethyl furfural to be the research report of raw material synthesis of maleic anhydride.The present invention prepares maleic anhydride through liquid phase selective oxidation 5 hydroxymethyl furfural, and this is one and has very big development potentiality variation route, has great importance and application background.
Summary of the invention
The object of the present invention is to provide a kind of variation route for preparing maleic anhydride through the liquid-phase oxidation 5 hydroxymethyl furfural.The raw material of traditional mode of production route is benzene, normal butane etc., and raw material of the present invention is a 5 hydroxymethyl furfural, and this raw material can obtain from biomass resource.
The oxygenated products of 5 hydroxymethyl furfural can have multiple, as 2, and 5-diacyl furans, 2,5-furans dioctyl phthalate etc.But the oxidation products under reaction conditions provided by the invention is to be main with maleic anhydride and toxilic acid, and this is a new oxidizing reaction route.
Catalyzer provided by the invention is an oxyvanadium compound.Comprise inorganic vanadium oxygen compound or organic vanadium oxygen compound.The inorganic vanadium oxide compound comprises vanadylic sulfate, vanadium phosphorus oxide, vanadium oxytrichloride, vanadyl pyrophosphate salt, Vanadium Pentoxide in FLAKES, phosphorus molybdenum vanadium heteropolyacid etc..The organic vanadium oxygen compound comprises that methyl ethyl diketone vanadyl, oxalic acid vanadyl, tartrate vanadyl, maltol vanadyl, pyridine carboxylic acid vanadyl, trimethoxy vanadyl, triethoxyoxyvanadium tripropoxy vanadyl, three isopropoxy vanadyl, two chloroethoxies close vanadyl etc.The consumption of catalyzer in oxidizing reaction is the 0.5-10mol% of 5 hydroxymethyl furfural amount.
The key step that the liquid-phase oxidation 5 hydroxymethyl furfural prepares maleic anhydride among the present invention has:
Catalyzer and 5 hydroxymethyl furfural are dropped in the autoclave, add proper amount of solvent, aerating oxygen or air, behind the closed reactor, stirring heating is warming up to 60-130 ℃, reaction times 0.5-10.0h.When temperature raising, catalyst levels increase, the reaction times can shorten, but cost up.Oxygen partial pressure is 0.3-2.5MPa, preferred 0.5-2.0MPa, and pressure increases the raising that helps maleic anhydride yield and speed of reaction, but the requirement of equipment and production safety is also significantly improved;
Solvent is common organic solvent, like acetonitrile, acetate, methyl alcohol, ethanol, cyanobenzene, N, and dinethylformamide, DMAC N,N etc., preferred acetonitrile, acetate.The used oxygen source of oxidizing reaction is oxygen or air.When being solvent, generate maleic anhydride and toxilic acid usually earlier, generate corresponding maleic acid methyl esters and ethyl maleate subsequently with methyl alcohol or ethanol.
The present invention has following characteristics:
It is oxygen source with the molecular oxygen that the present invention has reported a kind of, and 5 hydroxymethyl furfural is a raw material, and oxyvanadium compound is a catalyzer, through the variation route of liquid-phase oxidation synthesis of maleic anhydride.Raw material 5 hydroxymethyl furfural used in this route can obtain from biomass resource, can break away from the restriction of fossil resources such as oil; This route adopts liquid-phase oxidation, and reaction conditions is gentle, and energy consumption is low, oxidising process safety and easy handling; With oxygen or air is oxygenant, green economy; Catalyzer is cheap and easy to get simultaneously.Along with the consumption day by day of fossil resources such as oil, method provided by the invention has important application background and great development potentiality.
Description of drawings
Fig. 1: the major industry production route of maleic anhydride and the route that this patent provides;
Fig. 2: the parallel laboratory test GC comparison diagram of diacetyl oxide processed effect;
Fig. 3: the GC-MS of the oxidation products of not handling with diacetyl oxide.
Embodiment
Embodiment 1: with the 0.3150g 5 hydroxymethyl furfural, 5mol% methyl ethyl diketone vanadyl joins in the 50mL reaction kettle, adds the 5mL acetonitrile, closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 90 ℃ under stirring, and keeps 4h.Cool to room temperature then, normal pressure carefully reduces pressure.Whole products are transferred in the volumetric flask, and mark 2,3,5 in adding is used the acetone constant volume behind the 6-tetramethyl-benzene, and sampling uses the interior scalar quantity method of gas chromatographic analysis (GC) to obtain the content of maleic anhydride in the product then.Calculate according to formula maleic anhydride yield=(amount of substance of maleic anhydride)/(amount of substance of raw material 5 hydroxymethyl furfural), the yield of maleic anhydride is 43.4% (Fig. 2 is last).If add the 5mL diacetyl oxide, reflux product 2h promptly earlier changes into maleic anhydride with the toxilic acid in the product, and the total recovery that the chromatogram uantitative analytical gets maleic anhydride and toxilic acid is 51.7% (under Fig. 2).The gas chromatography retention time that uses GC-MS and reference material is to primary product qualitative (Fig. 3).
Embodiment 2: with the 0.3150g 5 hydroxymethyl furfural, 5mol% maltol vanadyl joins in the 50mL reaction kettle, adds the 5mL acetonitrile, closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 90 ℃ under stirring, and keeps 4h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, the total recovery that gets maleic anhydride and toxilic acid is 43.3%.
Embodiment 3: with the 0.3150g 5 hydroxymethyl furfural, 5mol% pyridine carboxylic acid vanadyl joins in the 50mL reaction kettle, adds 5mL acetate, closes still, and charging into oxygen pressure is 0.4MPa, is warming up to 60 ℃ under stirring, and keeps 8h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, the total recovery that gets maleic anhydride and toxilic acid is 29.6%.
Embodiment 4: with the 0.3150g 5 hydroxymethyl furfural, the 0.5mol% vanadylic sulfate joins in the 50mL reaction kettle, adds the 5mL acetonitrile, closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 90 ℃ under stirring, and keeps 6h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, the total recovery that gets maleic anhydride and toxilic acid is 32.6%.
Embodiment 5: with the 0.3150g 5 hydroxymethyl furfural, 2mol% methyl ethyl diketone vanadyl joins in the 50mL reaction kettle, adds the 5mL acetonitrile, closes still, and charging into oxygen pressure is 1.5MPa, is warming up to 100 ℃ under stirring, and keeps 4h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 42.1% of maleic anhydride and toxilic acid.
Embodiment 6: with the 0.3150g 5 hydroxymethyl furfural, the 10mol% vanadium phosphorus oxide joins in the 50mL reaction kettle, adds the 2mL acetonitrile, closes still, and charging into oxygen pressure is 0.5MPa, is warming up to 60 ℃ under stirring, and keeps 8h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 24.9% of maleic anhydride and toxilic acid.
Embodiment 7: with the 0.3150g 5 hydroxymethyl furfural, the 10mol% vanadium oxytrichloride joins in the 50mL reaction kettle, adds the 5mL acetonitrile, closes still, and charging into oxygen pressure is 0.5MPa, is warming up to 60 ℃ under stirring, and keeps 8h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 30.7% of maleic anhydride and toxilic acid.
Embodiment 8: with the 0.3150g 5 hydroxymethyl furfural, 1mol% methyl ethyl diketone vanadyl joins in the 50mL reaction kettle, adds the 5mL acetonitrile, closes still, and charging into oxygen pressure is 1.2MPa, is warming up to 120 ℃ under stirring, and keeps 2h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 52.3% of maleic anhydride and toxilic acid.
Embodiment 9: with the 0.3150g 5 hydroxymethyl furfural, the 0.5mol% Vanadium Pentoxide in FLAKES joins in the 50mL reaction kettle, adds the 5mL acetonitrile, closes still, and charging into oxygen pressure is 0.8MPa, is warming up to 60 ℃ under stirring, and keeps 12h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 32.6% of maleic anhydride and toxilic acid.
Embodiment 10: with the 0.3150g 5 hydroxymethyl furfural, 5mol% oxalic acid vanadyl joins in the 50mL reaction kettle, adds 5mL acetate, closes still, and charging into air pressure is 2.0MPa, is warming up to 90 ℃ under stirring, and keeps 2h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 50.2% of maleic anhydride and toxilic acid.
Embodiment 11: with the 0.3150g 5 hydroxymethyl furfural, 1mol% trimethoxy vanadyl joins in the 50mL reaction kettle, adds the 2mL acetonitrile, closes still, and charging into air pressure is 1.0MPa, is warming up to 100 ℃ under stirring, and keeps 4h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 48.2% of maleic anhydride and toxilic acid.
Embodiment 12: with the 3.15g 5 hydroxymethyl furfural, 2mol% three isopropoxy vanadyl join in the 100mL reaction kettle, add the 20mL acetonitrile, close still, and charging into oxygen pressure is 1.5MPa, are warming up to 80 ℃ under stirring, and keep 6h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 45.1% of maleic anhydride and toxilic acid.
Embodiment 13: with the 3.15g 5 hydroxymethyl furfural, 1mol% two chloroethoxies close vanadyl, join in the 100mL reaction kettle, add the 20mL acetonitrile, close still, and charging into oxygen pressure is 2.0MPa, are warming up to 120 ℃ under stirring, and keep 1h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 50.3% of maleic anhydride and toxilic acid.
Embodiment 14: with the 3.15g 5 hydroxymethyl furfural, the 10mol% phosphorus molybdenum vanadium heteropolyacid joins in the 100mL reaction kettle, adds the 20mL acetonitrile, closes still, and charging into oxygen pressure is 2.5MPa, is warming up to 130 ℃ under stirring, and keeps 0.5h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 55.0% of maleic anhydride and toxilic acid.
Embodiment 15: with the 3.15g 5 hydroxymethyl furfural, 2mol% vanadyl pyrophosphate salt joins in the 100mL reaction kettle, adds 10mL N, and dinethylformamide closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 60 ℃ under stirring, and keeps 15h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 45.4% of maleic anhydride and toxilic acid.
Embodiment 16: with the 3.15g 5 hydroxymethyl furfural, 0.5mol% tripropoxy vanadyl joins in the 100mL reaction kettle, adds the 40mL cyanobenzene, closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 120 ℃ under stirring, and keeps 5h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 55.4% of maleic anhydride and toxilic acid.
Embodiment 17: with the 6.3g 5 hydroxymethyl furfural, 5mol% tartrate vanadyl joins in the 100mL reaction kettle, adds 40mL acetate, closes still, and charging into oxygen pressure is 2.0MPa, is warming up to 100 ℃ under stirring, and keeps 5h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 57.3% of maleic anhydride and toxilic acid.
Embodiment 18: with the 1.20g 5 hydroxymethyl furfural, 10mol% triethoxy vanadyl joins in the 50mL reaction kettle, adds 10mL acetate, closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 90 ℃ under stirring, and keeps 4h.Cool to room temperature then, normal pressure carefully reduces pressure.According to the methods analyst product in the instance 1, get the total recovery 47.3% of maleic anhydride and toxilic acid.
Embodiment 19: with the 0.315g 5 hydroxymethyl furfural, 5mol% methyl ethyl diketone vanadyl joins in the 50mL reaction kettle, adds 5mL ethanol, closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 100 ℃ under stirring, and keeps 5h.Cool to room temperature then, normal pressure carefully reduces pressure.Analyze 43.3% diethyl maleate.
Embodiment 20: with the 0.315g 5 hydroxymethyl furfural, 5mol% methyl ethyl diketone vanadyl joins in the 50mL reaction kettle, adds 10mL methyl alcohol, closes still, and charging into oxygen pressure is 1.0MPa, is warming up to 100 ℃ under stirring, and keeps 4h.Cool to room temperature then, normal pressure carefully reduces pressure.Analyze 45.7% dimethyl maleate.
Claims (6)
1. a catalyzed oxidation 5 hydroxymethyl furfural prepares the method for maleic anhydride, and it is characterized in that: this method is oxygenant with the air or oxygen, and oxyvanadium compound is a catalyzer, and the liquid-phase oxidation 5 hydroxymethyl furfural prepares maleic anhydride and toxilic acid.
2. method according to claim 1 is characterized in that: it is oxyvanadium compound that the 5 hydroxymethyl furfural Selective Oxidation is saddled a horse for riding the catalyzer of acid anhydrides and toxilic acid; Oxyvanadium compound is one or more in inorganic vanadium oxygen compound and the organic vanadium oxygen compound.
3. method according to claim 2 is characterized in that: said inorganic vanadium oxygen compound is one or more in vanadylic sulfate, vanadium phosphorus oxide, vanadium oxytrichloride, vanadyl pyrophosphate salt, Vanadium Pentoxide in FLAKES, the phosphorus molybdenum vanadium heteropolyacid;
The organic vanadium oxygen compound is that methyl ethyl diketone vanadyl, oxalic acid vanadyl, tartrate vanadyl, maltol vanadyl, pyridine carboxylic acid vanadyl, trimethoxy vanadyl, triethoxyoxyvanadium tripropoxy vanadyl, three isopropoxy vanadyl, two chloroethoxies close one or more in the vanadyl.
4. method according to claim 1 is characterized in that: the 5 hydroxymethyl furfural Selective Oxidation is saddled a horse for riding in acid anhydrides and the toxilic acid process, and the oxyvanadium compound catalyst consumption is the 0.5-10mol% of raw material 5 hydroxymethyl furfural amount.
5. method according to claim 1 is characterized in that: saddling a horse for riding acid anhydrides and toxilic acid to react used oxygen source the 5 hydroxymethyl furfural Selective Oxidation is air or oxygen, and wherein oxygen partial pressure is 0.3-2.5MPa; Temperature of reaction is 60-130 ℃.
6. method according to claim 1 is characterized in that: react in the autoclave and carry out, the solvent that adopts in the reaction process liquid-phase system is acetonitrile, acetate, methyl alcohol, ethanol, cyanobenzene, N, dinethylformamide or DMAC N,N.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119219A (en) * | 2013-04-27 | 2014-10-29 | 中国科学院大连化学物理研究所 | Method for preparing maleic acid by virtue of oxidizing 5-hydroxymethyl furfural in aqueous phase |
| CN104119305A (en) * | 2013-04-27 | 2014-10-29 | 中国科学院大连化学物理研究所 | Method for preparing maleic anhydride through catalytic oxidation of 5-hydroxymethylfurfural |
| CN107011300A (en) * | 2017-05-27 | 2017-08-04 | 天津科林泰克科技有限公司 | A kind of method for preparing cis-butenedioic anhydride along sour continuous dehydration |
| US9725552B2 (en) | 2014-10-14 | 2017-08-08 | Industrial Technology Research Institute | HMF-based phenol formaldehyde resin |
| CN109608336A (en) * | 2018-12-21 | 2019-04-12 | 厦门大学 | A kind of method of a variety of dicarboxylic esters of coproduction |
| CN111187237A (en) * | 2020-02-03 | 2020-05-22 | 厦门大学 | Preparation method of maleic anhydride |
| JP7046977B2 (en) | 2017-04-27 | 2022-04-04 | 中国科学院大▲連▼化学物理研究所 | Equipment and methods for producing para-xylene from methanol and / or dimethyl ether and benzene and co-producing lower olefins |
| CN112645908B (en) * | 2019-10-11 | 2022-05-06 | 中国科学院大连化学物理研究所 | Method for preparing maleic anhydride |
| JP7462643B2 (en) | 2018-12-21 | 2024-04-05 | ネーデルランドセ・オルガニサティ・フォール・トゥーヘパスト－ナトゥールウェテンスハッペライク・オンデルズーク・テーエヌオー | Production of maleic acid by oxidation |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119219A (en) * | 2013-04-27 | 2014-10-29 | 中国科学院大连化学物理研究所 | Method for preparing maleic acid by virtue of oxidizing 5-hydroxymethyl furfural in aqueous phase |
| CN104119305A (en) * | 2013-04-27 | 2014-10-29 | 中国科学院大连化学物理研究所 | Method for preparing maleic anhydride through catalytic oxidation of 5-hydroxymethylfurfural |
| CN104119305B (en) * | 2013-04-27 | 2016-03-16 | 中国科学院大连化学物理研究所 | A kind of method of preparing maleic anhydride by catalytic oxidation of 5-hydroxymethylfurfural |
| CN104119219B (en) * | 2013-04-27 | 2016-08-10 | 中国科学院大连化学物理研究所 | A kind of method that aqueous phase oxidation 5 hydroxymethyl furfural prepares maleic acid |
| US9725552B2 (en) | 2014-10-14 | 2017-08-08 | Industrial Technology Research Institute | HMF-based phenol formaldehyde resin |
| JP7046977B2 (en) | 2017-04-27 | 2022-04-04 | 中国科学院大▲連▼化学物理研究所 | Equipment and methods for producing para-xylene from methanol and / or dimethyl ether and benzene and co-producing lower olefins |
| CN107011300A (en) * | 2017-05-27 | 2017-08-04 | 天津科林泰克科技有限公司 | A kind of method for preparing cis-butenedioic anhydride along sour continuous dehydration |
| CN107011300B (en) * | 2017-05-27 | 2020-04-24 | 天津科林泰克科技有限公司 | Method for preparing maleic anhydride by maleic acid continuous dehydration |
| CN109608336A (en) * | 2018-12-21 | 2019-04-12 | 厦门大学 | A kind of method of a variety of dicarboxylic esters of coproduction |
| JP7462643B2 (en) | 2018-12-21 | 2024-04-05 | ネーデルランドセ・オルガニサティ・フォール・トゥーヘパスト－ナトゥールウェテンスハッペライク・オンデルズーク・テーエヌオー | Production of maleic acid by oxidation |
| CN112645908B (en) * | 2019-10-11 | 2022-05-06 | 中国科学院大连化学物理研究所 | Method for preparing maleic anhydride |
| CN111187237A (en) * | 2020-02-03 | 2020-05-22 | 厦门大学 | Preparation method of maleic anhydride |
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Application publication date: 20120314 |