CN111187237A - Preparation method of maleic anhydride - Google Patents
Preparation method of maleic anhydride Download PDFInfo
- Publication number
- CN111187237A CN111187237A CN202010078316.8A CN202010078316A CN111187237A CN 111187237 A CN111187237 A CN 111187237A CN 202010078316 A CN202010078316 A CN 202010078316A CN 111187237 A CN111187237 A CN 111187237A
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- China
- Prior art keywords
- reaction
- catalyst
- maleic anhydride
- mixture
- yield
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 92
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims abstract description 30
- UHIPUIJTNVJGON-UHFFFAOYSA-N (5-formylfuran-2-yl)methyl formate Chemical compound O=COCC1=CC=C(C=O)O1 UHIPUIJTNVJGON-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000001590 oxidative effect Effects 0.000 claims abstract description 12
- 239000007800 oxidant agent Substances 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 239000000654 additive Substances 0.000 claims abstract description 8
- 230000000996 additive effect Effects 0.000 claims abstract description 7
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 72
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 29
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims description 6
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 4
- 239000004323 potassium nitrate Substances 0.000 claims description 4
- 235000010333 potassium nitrate Nutrition 0.000 claims description 4
- 239000004317 sodium nitrate Substances 0.000 claims description 4
- 235000010344 sodium nitrate Nutrition 0.000 claims description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 4
- 230000002195 synergetic effect Effects 0.000 claims description 4
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- ZHXZNKNQUHUIGN-UHFFFAOYSA-N chloro hypochlorite;vanadium Chemical compound [V].ClOCl ZHXZNKNQUHUIGN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 3
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 2
- 229960003280 cupric chloride Drugs 0.000 claims description 2
- 229960004643 cupric oxide Drugs 0.000 claims description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 2
- 229940112669 cuprous oxide Drugs 0.000 claims description 2
- -1 oxone Chemical compound 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000003426 co-catalyst Substances 0.000 claims 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 9
- 239000002028 Biomass Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- NTXGERACGDZHSG-UHFFFAOYSA-N 5-(2-oxoethyl)furan-2-carbaldehyde Chemical compound C(=O)CC1=CC=C(C=O)O1 NTXGERACGDZHSG-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 58
- 239000008367 deionised water Substances 0.000 description 29
- 229910021641 deionized water Inorganic materials 0.000 description 29
- 238000003760 magnetic stirring Methods 0.000 description 29
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- HDMGAZBPFLDBCX-UHFFFAOYSA-M potassium;sulfooxy sulfate Chemical compound [K+].OS(=O)(=O)OOS([O-])(=O)=O HDMGAZBPFLDBCX-UHFFFAOYSA-M 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910015711 MoOx Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
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Classifications
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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
- C07D307/56—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 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
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/32—Manganese, technetium or rhenium
- B01J23/34—Manganese
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/745—Iron
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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
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/053—Sulfates
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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
- B01J27/06—Halogens; Compounds thereof
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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
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/122—Halides of copper
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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
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
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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
- B01J27/06—Halogens; Compounds thereof
- B01J27/132—Halogens; Compounds thereof 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
- B01J27/24—Nitrogen compounds
- B01J27/25—Nitrates
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- B01J35/19—
Abstract
A preparation method of maleic anhydride relates to maleic anhydride. Provides a preparation method of maleic anhydride with the characteristics of high yield, easy separation, low cost, less pollution and the like. 5-formyloxymethylfurfural or 5-hydroxymethylfurfural is used as a reaction substrate, mixed with a reaction solvent, an oxidant, an additive and a catalyst in a reactor according to a certain proportion, and subjected to a closed reaction for a certain time at a certain temperature to obtain maleic anhydride after the reaction is finished. A method for preparing MA by using atmospheric air oxygen as an oxidant and using a biomass platform compound 5-formylmethylfurfural or 5-hydroxymethylfurfural as a raw material. Has the characteristics of high yield, easy separation, low cost, less pollution and the like. The catalyst is efficient, the using amount is small, the catalyst is simple and easy to obtain, the product yield is high, the byproducts are few, the reaction condition is mild, the method is green, economic and environment-friendly, the conversion rate exceeds 99%, and the selectivity is more than 93%. The purity of the product after separation, recrystallization and purification is higher than 99.9 percent.
Description
Technical Field
The invention relates to maleic anhydride, in particular to a preparation method of maleic anhydride by taking 5-formyloxymethylfurfural or 5-hydroxymethylfurfural as a reaction substrate in a composite catalyst system.
Background
Due to the enormous social concern for energy supply and environmental pollution, biomass is considered as a promising raw material to meet the demands of the fully sustainable bio-commodity industry. In recent years, the development of new renewable chemicals from sugar platforms, such as biomass-derived chemicals based on 5-hydroxymethylfurfural and levulinic acid, has gained wide acceptance (ChemSusChem,7(2014)402-406.ChemSusChem,6(2013)1659-1667. angelwash Chemie,119(2007)7780-7783.ChemSusChem,4(2011) 1758-1761.). The conversion of biomass into fine chemicals to replace fossil resources will become an important layout of energy strategies in future green development of the world. Maleic Anhydride (MA) is a commonly used important basic organic chemical raw material, the third largest anhydride raw material second only to acetic anhydride and phthalic anhydride in the world. The downstream products have quite wide development and application prospects. It is mainly used for synthesizing unsaturated polyester resin, and is a raw material for manufacturing automobile parts, ships, corrosion-resistant chemical equipment and daily necessities. Maleic anhydride is also an important intermediate for producing additives, coatings, pesticides, fumaric acid, copolymers, food additives and the like for lubricating oils. Hydrogenated derivatives thereof include succinic anhydride, 1, 4-butanediol, r-j lactone and tetrahydrofuran (Angewchem Int Ed Engl,50(2011) 10502-10509.). In the current industrial production, MA is produced mainly by selective oxidation of benzene, o-xylene or n-butane. These routes are dependent on petroleum feedstocks, and the shortage of fossil resources and environmental problems caused by the petroleum industry are also of great concern to the world population.
Therefore, the preparation of renewable maleic anhydride using furfural (FF), a biomass platform compound, as a reaction substrate, has become a popular research since 1949, in which VO was developedx、MoOxCatalyst systems with predominantly metal active components (ChemSusChem,5(2012), 1984-1990.Green chem.,16(2014)4351-4358.Green Chemistry,18(2016) 2976-. At the same time researchers have also developed a potentially renewable route to MA from 5-Hydroxymethylfurfural (HMF). In several studies reported on the preparation of MA from HMF, the yield of MA hardly exceeded 52%, although the overall yield of MA and maleic acid was as high as 79% (ACS Catalysis,5(2015), 2035-2041.GreenChemistry,18(2016)643-647.Green Chemistry,13(2011) 554). In general, FF as a feedstock has a higher MA yield advantage and atom economy than HMF, but requires higher reaction temperatures. And no matter HMF or FF is used as a raw material, high-purity oxygen is needed as an oxidant and an acidic environment in the reaction process, so that the requirement on the reactor is high. Therefore, there is still a need to develop more economical and efficient reaction processes to produce MA with high efficiency, especially under mild reaction conditions.
Disclosure of Invention
The invention aims to provide a preparation method of maleic anhydride, which has the characteristics of high yield, easy separation, low cost, less pollution and the like. The maleic anhydride is prepared by catalyzing 5-formyloxymethylfurfural or 5-hydroxymethylfurfural.
The invention comprises the following steps:
5-formyloxymethylfurfural or 5-hydroxymethylfurfural is used as a reaction substrate, mixed with a reaction solvent, an oxidant, an additive and a catalyst in a reactor according to a certain proportion, and subjected to a closed reaction for a certain time at a certain temperature to obtain maleic anhydride after the reaction is finished.
The reaction solvent is at least one of acetonitrile, toluene, dichlorotoluene, 1, 4-dioxane, ethyl acetate, acetone and the like, and the mass concentration of a reaction substrate can be 0.001-0.3 g/mL.
The oxidant can be at least one of potassium persulfate, potassium hydrogen persulfate, ammonium persulfate, sodium hydrogen persulfate or oxygen, and the molar ratio of the oxidant to the reaction substrate can be (0.1-1.5): 1; the potassium sulfate or the potassium hydrogen persulfate not only plays a role of an oxidant in the reaction process, but also generates sulfuric acid in the reaction process to provide certain acidity for a reaction system; the mixed acid anhydride is formed by the byproduct formic acid generated by oxidizing the 5-formyloxymethylfurfural or the 5-hydroxymethylfurfural and the sulfuric acid, so that the maleic anhydride is not easy to be hydrolyzed into the maleic acid.
The catalyst can adopt a bimetallic catalyst, and the bimetallic catalyst is a composite catalyst consisting of a main catalyst and a synergistic catalyst; the main catalyst is at least one of manganese dioxide, molybdenum trioxide, vanadium oxychloride, ferric nitrate, ferric chloride, ferric sulfate, ferric oxide and the like, and the synergistic catalyst is at least one of cupric chloride, cupric nitrate, cupric oxide, cuprous oxide, copper sulfate, sodium nitrate, potassium nitrate, aluminum oxide and the like; the mass ratio of the bimetallic catalyst to the reaction substrate can be (0.01-0.5): 1; the mass ratio of the synergistic catalyst to the main catalyst in the bimetallic catalyst can be (0-2): 1.
The additive is water, and the volume ratio of the additive to the reaction solvent is (0-1): 1.
The reaction temperature can be 70-130 ℃, and the reaction time can be 1-20 h.
Compared with the prior art, the invention has the following outstanding advantages:
the invention reports a method for preparing MA by using atmospheric air oxygen as an oxidant and using a biomass platform compound 5-formylmethylfurfural or 5-hydroxymethylfurfural as a raw material for the first time. The method has the characteristics of high yield, easy separation, low cost, less pollution and the like. The catalyst has the advantages of high efficiency, small using amount, simplicity, easy obtaining, high product yield, few byproducts, mild reaction conditions, green, economic and environment-friendly method, conversion rate of over 99 percent and selectivity of over 93 percent. The purity of the product after separation, recrystallization and purification is higher than 99.9 percent.
Drawings
FIG. 1 shows maleic anhydride isolated as a product of example 21H NMR(DMSO-d6) Nuclear magnetic resonance image.
FIG. 2 shows maleic anhydride isolated as a product of example 213C NMR(DMSO-d6) Nuclear magnetic resonance image.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the following embodiments will be further described with reference to the accompanying drawings. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. On the contrary, the invention is intended to cover alternatives, modifications, equivalents and alternatives which may be included within the spirit and scope of the invention as defined by the appended claims. Furthermore, in the following detailed description of the present invention, certain specific details are set forth in order to provide a better understanding of the present invention. It will be apparent to one skilled in the art that the present invention may be practiced without these specific details.
Example 1:
8.50g of 5-formyloxymethylfurfural (FMF), 22.32g of potassium persulfate, 2.13g of manganese dioxide, 2.13g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 130 ℃ with magnetic stirring and reacted for 10 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 80.39%.
Example 2:
3.00g of 5-formyloxymethylfurfural (FMF), 6.30g of potassium persulfate, 0.7g of manganese dioxide, 0.8g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 110 ℃ with magnetic stirring and reacted for 7 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 86.54%.
EXAMPLE 2 isolation of the product maleic anhydride1H NMR(DMSO-d6) Nuclear magnetic resonance image1. EXAMPLE 2 isolation of the product maleic anhydride13C NMR(DMSO-d6) The NMR chart is shown in FIG. 2.
Example 3:
1.50g of 5-formyloxymethylfurfural (FMF), 2.89g of potassium persulfate, 0.19g of manganese dioxide, 0.19g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 100 ℃ with magnetic stirring and reacted for 6 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 90.38%.
Example 4:
0.30g of 5-formyloxymethylfurfural (FMF), 0.58g of potassium persulfate, 0.015g of manganese dioxide, 0.015g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 90 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 94.38%.
Example 5:
0.03g of 5-formyloxymethylfurfural (FMF), 0.48g of potassium persulfate, 0.015g of manganese dioxide, 0.015g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 75 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 91.22%.
Example 6:
0.03g of 5-formyloxymethylfurfural (FMF), 0.48g of potassium persulfate, 0.002g of manganese dioxide, 0.001g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 100 ℃ with magnetic stirring and reacted for 8 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 93.45%.
Example 7:
0.30g of 5-formyloxymethylfurfural (FMF), 0.52g of potassium persulfate, 0.015g of manganese dioxide, 0.03g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 90 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 92.56%.
Example 8:
0.30g of 5-formyloxymethylfurfural (FMF), 0.69g of potassium persulfate, 0.03g of manganese dioxide, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 85 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 88.56%.
Example 9:
0.30g of 5-formyloxymethylfurfural (FMF), 0.06g of potassium persulfate, 0.015g of manganese dioxide, 0.015g of copper nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 90 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 83.78%.
Example 10:
0.30g of 5-formyloxymethylfurfural (FMF), 0.65g of potassium persulfate, 0.015g of molybdenum trioxide, 0.015g of copper chloride, 27mL of acetonitrile and 3mL of deionized water are added into a 50mL reaction kettle, and the mixture is heated to 100 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 86.52%.
Example 11:
0.30g of 5-formyloxymethylfurfural (FMF), 0.70g of potassium persulfate, 0.02g of vanadium oxychloride, 0.01g of cuprous chloride, 27mL of acetonitrile and 3mL of deionized water are added into a 50mL reaction kettle, and the mixture is heated to 80 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 88.45 percent.
Example 12:
0.30g of 5-formyloxymethylfurfural (FMF), 0.70g of potassium persulfate, 0.02g of ferric nitrate, 0.01g of copper sulfate, 27mL of acetonitrile and 3mL of deionized water were added to a 50mL reaction kettle, and the mixture was heated to 100 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 86.66%.
Example 13:
0.30g of 5-formyloxymethylfurfural (FMF), 0.75g of potassium persulfate, 0.02g of ferric chloride, 0.02g of copper sulfate, 27mL of acetonitrile and 3mL of deionized water were added to a 50mL reaction kettle, and the mixture was heated to 120 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 89.44%.
Example 14:
0.30g of 5-formyloxymethylfurfural (FMF), 0.65g of potassium persulfate, 0.03g of ferric sulfate, 0.03g of sodium nitrate, 27mL of acetonitrile and 3mL of deionized water were added to a 50mL reaction kettle, and the mixture was heated to 120 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 80.44%.
Example 15:
0.30g of 5-formyloxymethylfurfural (FMF), 0.60g of potassium persulfate, 0.04g of ferric oxide, 0.03g of sodium nitrate, 27mL of acetonitrile and 3mL of deionized water are added into a 50mL reaction kettle, and the mixture is heated to 130 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 89.84%.
Example 16:
0.30g of 5-formyloxymethylfurfural (FMF), 0.60g of potassium persulfate, 0.02g of manganese dioxide, 0.02g of potassium nitrate, 27mL of acetonitrile and 3mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 120 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 84.48%.
Example 17:
0.30g of 5-formyloxymethylfurfural (FMF), 0.65g of potassium persulfate, 0.02g of manganese dioxide, 0.02g of aluminum oxide, 27mL of acetonitrile and 3mL of deionized water are added into a 50mL reaction kettle, and the mixture is heated to 110 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 85.65%.
Example 18:
0.30g of 5-formyloxymethylfurfural (FMF), 0.60g of potassium persulfate, 0.02g of manganese dioxide, 0.01g of copper nitrate and 27mL of toluene were put into a 50mL reaction vessel, and the mixture was heated to 100 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 70.56%.
Example 19:
0.50g of 5-formyloxymethylfurfural (FMF), 0.88g of potassium persulfate, 0.03g of manganese dioxide, 0.02g of copper nitrate, 25mL of dichlorotoluene, and 5mL of deionized water were put into a 50mL reaction vessel, and heated to 90 ℃ with magnetic stirring for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 96.35%.
Example 20:
0.50g of 5-formyloxymethylfurfural (FMF), 1.00g of potassium persulfate, 0.025g of manganese dioxide, 0.025g of copper nitrate, 25mL of 1, 4-dioxane and 25mL of deionized water were put into a 50mL reaction vessel, heated to 80 ℃ with magnetic stirring, and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 84.76%.
Example 21:
0.30g of 5-formyloxymethylfurfural (FMF), 0.55g of potassium persulfate, 0.03g of manganese dioxide, 0.02g of copper nitrate, 25mL of ethyl acetate and 5mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 90 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 84.76%.
Example 22:
0.30g of 5-formyloxymethylfurfural (FMF), 0.55g of potassium persulfate, 0.03g of manganese dioxide, 0.02g of copper nitrate, 30mL of acetone and 10mL of deionized water were put into a 50mL reaction vessel, and the mixture was heated to 100 ℃ with magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 90.18%.
Example 23:
0.30g of 5-Hydroxymethylfurfural (HMF), 0.65g of potassium persulfate, 0.03g of manganese dioxide, 0.02g of copper nitrate, 25mL of acetonitrile in acetone and 5mL of deionized water are added into a 50mL reaction kettle, and the mixture is heated to 90 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 94.11%.
Example 24:
0.30g of 5-Hydroxymethylfurfural (HMF), 0.75g of potassium persulfate, 0.02g of manganese dioxide, 0.02g of copper nitrate, 50mL of acetonitrile in acetone and 10mL of deionized water are added into a 100mL reaction kettle, and the mixture is heated to 90 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 92.33%.
Example 25:
0.30g of 5-Hydroxymethylfurfural (HMF), 0.70g of potassium persulfate, 0.015g of manganese dioxide, 0.01g of copper nitrate, 100mL of acetonitrile and 20mL of deionized water are added into a 100mL reaction kettle, and the mixture is heated to 90 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 95.78%.
Example 26:
0.30g of 5-Hydroxymethylfurfural (HMF), 0.50g of potassium persulfate, 0.02g of manganese dioxide, 0.01g of copper nitrate, 50mL of 1, 4-dioxane and 10mL of deionized water are added into a 100mL reaction kettle, and the mixture is magnetically stirred and heated to 100 ℃ for reaction for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 92.88 percent.
Example 27:
0.30g of 5-Hydroxymethylfurfural (HMF), 0.80g of sodium persulfate, 0.03g of manganese dioxide, 0.01g of potassium nitrate, 50mL of 1, 4-dioxane and 10mL of deionized water are added into a 100mL reaction kettle, and the mixture is heated to 110 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 90.24%.
Example 28:
0.30g of 5-Hydroxymethylfurfural (HMF), 0.65g of ammonium persulfate, 0.03g of manganese dioxide, 0.03g of copper nitrate, 50mL of acetonitrile and 10mL of deionized water are added into a 100mL reaction kettle, and the mixture is heated to 90 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 93.45%.
Example 29:
0.30g of 5-Hydroxymethylfurfural (HMF), 0.45g of potassium peroxydisulfate, 0.025g of manganese dioxide, 0.025g of copper nitrate, 50mL of acetone and 10mL of deionized water are added into a 100mL reaction kettle, and the mixture is heated to 100 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system is cooled to room temperature, and the yield of the Maleic Anhydride (MA) is 88.56%.
Example 30:
0.30g of 5-Hydroxymethylfurfural (HMF), 1.00g of sodium peroxodisulfate, 0.025g of manganese dioxide, 0.015g of copper nitrate, 30mL of acetonitrile and 10mL of deionized water are added into a 100mL reaction kettle, and the mixture is heated to 90 ℃ by magnetic stirring and reacted for 5 hours. The mixture in the reaction system was cooled to room temperature, and the yield of Maleic Anhydride (MA) was 90.33%.
Claims (10)
1. A preparation method of maleic anhydride is characterized by comprising the following steps:
5-formyloxymethylfurfural or 5-hydroxymethylfurfural is used as a reaction substrate, mixed with a reaction solvent, an oxidant, an additive and a catalyst in a reactor according to a certain proportion, and subjected to a closed reaction for a certain time at a certain temperature to obtain maleic anhydride after the reaction is finished.
2. The method according to claim 1, wherein the reaction solvent is at least one of acetonitrile, toluene, dichlorotoluene, 1, 4-dioxane, ethyl acetate, and acetone.
3. The method according to claim 1, wherein the mass concentration of the reaction substrate is 0.001 to 0.3 g/mL.
4. The method for preparing maleic anhydride according to claim 1, wherein the oxidant is at least one selected from potassium persulfate, oxone, ammonium persulfate, sodium persulfate and oxygen, and the molar ratio of the oxidant to the reaction substrate is (0.1-1.5): 1.
5. The process for producing maleic anhydride according to claim 1, wherein the catalyst is a bimetallic catalyst.
6. The method according to claim 5, wherein the bimetallic catalyst is a composite catalyst comprising a main catalyst and a cocatalyst.
7. The method according to claim 5, wherein the main catalyst is at least one selected from manganese dioxide, molybdenum trioxide, vanadium oxychloride, ferric nitrate, ferric chloride, ferric sulfate and ferric oxide, and the co-catalyst is at least one selected from cupric chloride, cupric nitrate, cupric oxide, cuprous oxide, cupric sulfate, sodium nitrate, potassium nitrate and aluminum oxide; the mass ratio of the synergistic catalyst to the main catalyst in the bimetallic catalyst can be (0-2): 1.
8. The method according to claim 1, wherein the mass ratio of the catalyst to the reaction substrate is (0.01-0.5): 1.
9. The method according to claim 1, wherein the additive is water, and the volume ratio of the additive to the reaction solvent is (0-1): 1.
10. The method according to claim 1, wherein the reaction temperature is 70 to 130 ℃ and the reaction time is 1 to 20 hours.
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