CN115418246A - Naphthenic hydrocarbon fuel and preparation method thereof - Google Patents
Naphthenic hydrocarbon fuel and preparation method thereof Download PDFInfo
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- CN115418246A CN115418246A CN202210973068.2A CN202210973068A CN115418246A CN 115418246 A CN115418246 A CN 115418246A CN 202210973068 A CN202210973068 A CN 202210973068A CN 115418246 A CN115418246 A CN 115418246A
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- solid acid
- metal
- acid catalyst
- fuel
- naphthenic
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- 239000000446 fuel Substances 0.000 title claims abstract description 57
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 21
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 21
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 68
- 239000011973 solid acid Substances 0.000 claims abstract description 66
- 239000004033 plastic Substances 0.000 claims abstract description 43
- 229920003023 plastic Polymers 0.000 claims abstract description 43
- 239000002699 waste material Substances 0.000 claims abstract description 40
- 229910052751 metal Inorganic materials 0.000 claims abstract description 38
- 239000002184 metal Substances 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000001301 oxygen Substances 0.000 claims abstract description 28
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
- 239000002808 molecular sieve Substances 0.000 claims abstract description 20
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000010457 zeolite Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 4
- 239000004927 clay Substances 0.000 claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 claims abstract description 4
- OJLGWNFZMTVNCX-UHFFFAOYSA-N dioxido(dioxo)tungsten;zirconium(4+) Chemical compound [Zr+4].[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O OJLGWNFZMTVNCX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 4
- ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 claims abstract description 4
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 claims abstract description 4
- CNHRNMLCYGFITG-UHFFFAOYSA-A niobium(5+);pentaphosphate Chemical compound [Nb+5].[Nb+5].[Nb+5].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O CNHRNMLCYGFITG-UHFFFAOYSA-A 0.000 claims abstract description 4
- 229910000166 zirconium phosphate Inorganic materials 0.000 claims abstract description 4
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 claims abstract description 4
- -1 polyethylene terephthalate Polymers 0.000 claims description 20
- 239000004417 polycarbonate Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 9
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 6
- 239000003502 gasoline Substances 0.000 claims description 6
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 6
- 229920002530 polyetherether ketone Polymers 0.000 claims description 6
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 6
- 239000002283 diesel fuel Substances 0.000 claims description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 claims description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 4
- 239000011112 polyethylene naphthalate Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000005470 impregnation Methods 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 229920001652 poly(etherketoneketone) Polymers 0.000 claims description 2
- 229920001955 polyphenylene ether Polymers 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 18
- 238000001816 cooling Methods 0.000 description 12
- 238000011068 loading method Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Chemical compound CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 229910002845 Pt–Ni Inorganic materials 0.000 description 3
- 229910002787 Ru-Ni Inorganic materials 0.000 description 3
- 229910002793 Ru–Ni Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920006380 polyphenylene oxide Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001657 poly(etheretherketoneketone) Polymers 0.000 description 1
- 229920001660 poly(etherketone-etherketoneketone) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/10—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal from rubber or rubber waste
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J29/42—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing iron group metals, noble metals or copper
- B01J29/46—Iron group metals or copper
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
- B01J29/76—Iron group metals or copper
- B01J29/7615—Zeolite Beta
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/06—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation
-
- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1003—Waste materials
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/70—Catalyst aspects
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/02—Gasoline
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/04—Diesel oil
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
Abstract
The invention provides a naphthenic fuel and a preparation method thereof. The preparation method of the naphthenic fuel comprises the following steps: in the presence of a solvent, catalyzing aromatic oxygen-containing waste plastics by adopting a supported metal-solid acid catalyst to perform hydrodeoxygenation reaction to obtain the naphthenic hydrocarbon fuel; wherein the supported metal-solid acid catalyst comprises an active metal and a solid acid support, the active metal being supported on the solid acid support; the active metal comprises at least one of Ru, ir, pd, pt, rh, ni, fe, co and Cu; the solid acid carrier comprises at least one of zeolite molecular sieve, amorphous silicon-aluminum material, heteropoly acid, zirconium phosphate, zirconium tungstate, acidic clay, niobium phosphate, niobium pentoxide and acidic cation exchange resin. The method is simple, efficient and low in cost, and can be carried out under low temperature.
Description
Technical Field
The invention relates to the technical field of energy sources, in particular to a naphthenic hydrocarbon fuel and a preparation method thereof.
Background
With the increasing use of plastic articles by humans, waste plastic has become a global problem. Currently, the main method for disposing of these waste plastic products is to recycle them mechanically, but this method's deterioration of the plastic quality limits the wide application of the method, for example, only 7% of polyethylene terephthalate (PET) is recycled. Therefore, the method has positive significance for the development of environmental protection and recycling economy in order to reduce the discharge of plastics into the environment as much as possible and simultaneously degrade and convert waste plastics into high-value chemical products. Gasoline, jet fuel or diesel fuel are transportation fuels which are in great demand internationally. At present, gasoline, aviation kerosene and diesel oil are mainly prepared by using crude oil as a raw material through processes of rectification, cracking, reforming and the like, and have non-regenerability. With the decreasing of petroleum resources and the rising of international crude oil prices, the prices of gasoline, aviation kerosene or diesel oil are also rising.
Waste plastics are used as wastes of fossil resource using terminals, and can be used as a novel resource for synthesis and preparation of fuels. The realization of the process technology has important significance for the upgrading utilization of waste plastics and can reduce the dependence on fossil resources to a certain extent. The existing synthetic method for preparing fuel by utilizing waste plastics has the following problems: 1) The steps are complex, two different reactions (alcoholysis of waste plastics into monomers and hydrodeoxygenation monomers) are required; 2) The hydrodeoxygenation step requires a relatively high reaction temperature (200-400 ℃); 3) Two different catalysts are required.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
The present invention is directed to solving, at least to some extent, one of the technical problems in the related art. Therefore, one object of the present invention is to provide a method for preparing naphthenic hydrocarbon fuel, which is simple, efficient, low-cost, can be performed at low temperature, and can realize a one-pot method for directly preparing naphthenic hydrocarbon fuel by completely hydrodeoxygenating aromatic oxygen-containing waste plastics.
In one aspect of the present invention, there is provided a method for preparing a naphthenic fuel, the method comprising:
in the presence of a solvent, catalyzing aromatic oxygen-containing waste plastics by adopting a supported metal-solid acid catalyst to perform hydrodeoxygenation reaction to obtain the naphthenic hydrocarbon fuel;
wherein the supported metal-solid acid catalyst comprises an active metal and a solid acid support, the active metal being supported on the solid acid support;
the active metal comprises at least one of Ru, ir, pd, pt, rh, ni, fe, co and Cu; the solid acid carrier comprises at least one of zeolite molecular sieve, amorphous silicon-aluminum material, heteropoly acid, zirconium phosphate, zirconium tungstate, acidic clay, niobium phosphate, niobium pentoxide and acidic cation exchange resin.
Further, the zeolite molecular sieve comprises at least one of H-ZSM-5, H-Y, H-USY, H-beta, H-MOR, H-MCM-22, and H-SAPO molecular sieves.
Further, the content of the active metal is 0.1 to 50wt% based on the total mass of the supported metal-solid acid catalyst;
and/or the active metal is contained in an amount of 1 to 30wt% based on the total mass of the supported metal-solid acid catalyst.
Further, the preparation method of the supported metal-solid acid catalyst comprises the following steps:
adding a metal soluble salt solution into the solid acid carrier for isovolumetric impregnation, then drying at 50-120 ℃ for 2-24 h, then roasting at 300-700 ℃ for 0-6 h to obtain the supported metal-solid acid catalyst,
wherein the metal in the metal soluble salt corresponds to the metal in the active metal.
Further, the supported metal-solid acid catalyst needs to be subjected to reduction treatment before use;
and/or the reduction treatment comprises the following steps: in a batch type reaction kettle, the supported metal-solid acid catalyst is placed in a hydrogen atmosphere of 0.1 to 20MPa and reduced for 0.5 to 6 hours at the temperature of 180 to 300 ℃;
and/or the reduction treatment comprises the following steps: in a tubular furnace, the supported metal-solid acid catalyst is placed in a normal pressure hydrogen atmosphere at the hydrogen flow rate of 10-200 ml/min, and is reduced for 0.5-6 h at the temperature of 300-600 ℃.
Further, the solvent comprises an alkane and/or water.
Further, the aromatic oxygen-containing waste plastic comprises at least one of polycarbonate, polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene isophthalate, polyethylene naphthalate, polyether ether ketone, polyether ketone, polyether ether ketone, polyether ketone ether ketone, and polyphenylene oxide.
Further, the conditions of the hydrodeoxygenation reaction include: the temperature is 100-400 ℃, the hydrogen pressure is 0.1-20 MPa, the stirring speed is 100-2000 rpm, and the reaction time is 0-96 h.
Further, the naphthenic fuel comprises naphthenic fuel in the range of C6-C15;
and/or the naphthenic fuel comprises at least one of gasoline, jet fuel and diesel.
In another aspect of the present invention, the present invention provides a naphthenic fuel, which is prepared by the preparation method described above.
Compared with the prior art, the invention can at least obtain the following beneficial effects:
the solid acid carrier in the load type metal-solid acid multifunctional catalyst has rich acid sites, can effectively activate C-O bonds, efficiently catalyzes aromatic oxygen-containing waste plastics to carry out hydrodeoxygenation under the synergistic action of active metal components which are easy to activate hydrogen, ensures that the waste plastics degradation reaction is carried out under the condition of mild temperature and pressure, simultaneously improves the selectivity and yield of a product cycloparaffin fuel, ensures that the yield of the cycloparaffin fuel can reach more than 90 percent, and ensures the oil property of the product fuel; the invention can realize the one-pot method to directly and completely hydrodeoxygenate the aromatic oxygen-containing waste plastics to prepare the naphthenic fuel, has simple process, high efficiency, low cost and low energy consumption, and is a green and simple new production line for preparing the high-density aviation fuel oil by taking the aromatic oxygen-containing waste plastics as the raw material; the invention not only provides a method for solving the problem of environmental pollution of waste plastics, but also helps to reduce the dependence on fossil energy.
Drawings
FIG. 1 GC graph of the reaction product of example 1;
FIG. 2 is a GC-MS plot of cyclohexane, the main product of the reaction product of example 1;
FIG. 3 is a GC-MS plot of the main product isopropylcyclohexane in the reaction product of example 1;
FIG. 4 is a GC-MS plot of the main product, the C15 bicyclic product, in the reaction product of example 1.
Detailed Description
The following describes embodiments of the present invention in detail. The following examples are illustrative only and are not to be construed as limiting the invention. The examples, where specific techniques or conditions are not indicated, are to be construed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.
In one aspect of the present invention, there is provided a method for preparing a naphthenic fuel, the method comprising:
in the presence of a solvent, catalyzing aromatic oxygen-containing waste plastics by adopting a supported metal-solid acid catalyst to perform hydrodeoxygenation reaction to obtain the naphthenic hydrocarbon fuel;
wherein the supported metal-solid acid catalyst comprises an active metal and a solid acid support, the active metal being supported on the solid acid support;
the active metal includes at least one of Ru (ruthenium), ir (iridium), pd (palladium), pt (platinum), rh (rhodium), ni (nickel), fe (iron), co (cobalt), and Cu (copper); the solid acid carrier comprises at least one of zeolite molecular sieve, amorphous silicon-aluminum material, heteropoly acid, zirconium phosphate, zirconium tungstate, acidic clay, niobium phosphate, niobium pentoxide and acidic cation exchange resin.
The solid acid carrier in the supported metal-solid acid multifunctional catalyst has rich acid sites, can effectively activate C-O bonds, efficiently catalyzes aromatic oxygen-containing waste plastic to carry out hydrodeoxygenation under the synergistic action of active metal components which can easily activate hydrogen, ensures that the waste plastic degradation reaction is carried out under the condition of mild temperature and pressure (in some preferred embodiments of the invention, the waste plastic degradation reaction can be carried out under the condition of 160-200 ℃), improves the selectivity and yield of the product naphthenic hydrocarbon fuel, ensures the yield of the naphthenic hydrocarbon fuel to be more than 90 percent, and ensures the oil property of the product fuel; the invention can realize the one-pot method to directly and completely hydrodeoxygenate the aromatic oxygen-containing waste plastics to prepare the naphthenic fuel, has simple process, high efficiency, low cost and low energy consumption, and is a green and simple new production line for preparing the high-density aviation fuel oil by taking the aromatic oxygen-containing waste plastics as the raw material; the invention not only provides a method for solving the problem of environmental pollution of waste plastics, but also helps to reduce the dependence on fossil energy.
The aromatic oxygen-containing waste plastic is a polymer plastic mainly obtained by polymerizing an aromatic oxygen-containing compound precursor.
In some embodiments of the present invention, the aromatic oxygen-containing waste plastic comprises polycarbonate (abbreviated as PC in English and having the structural formula
Polyethylene terephthalate (English is abbreviated as PET, and the structural formula is shown in the specification
) Polytrimethylene terephthalate (abbreviated as PPT in English and with the structural formula
) Polybutylene terephthalate (PBT for short in English, the structural formula is shown in the specification
) Polyethylene isophthalate and polyethylene naphthalate (PEN for short, the structural formula is shown in the specification
) Polyetheretherketone (PEEK for short English, with the structural formula
Polyether ketone (PEK for short, the structural formula is shown in the specification)
) Polyether ketone (PEKK, english abbreviation, structure formula)
) Polyether ether ketone (PEEKK for short, and the structural formula is shown in the specification
) Polyether ketone ether ketone (PEKEKK, the structural formula is shown in the specification)
) And polyphenylene oxide (abbreviated as PPO in English, with the structural formula
) At least one of; in the above structural formula, n represents a natural number of 2 or more.
In some embodiments of the invention, the zeolitic molecular sieve comprises a microporous zeolitic molecular sieve and a multigrade pore zeolitic molecular sieve.
In some embodiments of the invention, the zeolite molecular sieve comprises at least one of H-ZSM-5, H-Y, H-USY, H-beta, H-MOR, H-MCM-22, and H-SAPO molecular sieves.
In some embodiments of the invention, the active metal is present in an amount of 0.1 to 50wt% (e.g., can be 0.1wt%, 1wt%, 5wt%, 10wt%, 15wt%, 20wt%, 25wt%, 30wt%, 35wt%, 40wt%, 45wt%, or 50wt%, etc.) based on the total mass of the supported metal-solid acid catalyst.
In some preferred embodiments of the present invention, the active metal is contained in an amount of 1 to 30wt% based on the total mass of the supported metal-solid acid catalyst.
In some embodiments of the present invention, the supported metal-solid acid catalyst is prepared by a method comprising:
adding a metal soluble salt solution into the solid acid carrier for isovolumetric impregnation, then drying at 50-120 ℃ for 2-24 h, and then roasting at 300-700 ℃ for 0-6 h to obtain the supported metal-solid acid catalyst, wherein the metal in the metal soluble salt corresponds to the metal in the active metal, for example, when the active metal is Ni, the metal in the metal soluble salt is also Ni.
In some embodiments of the present invention, the supported metal-solid acid catalyst is subjected to a reduction treatment before use.
In some embodiments of the invention, the reduction treatment comprises: in a batch type reaction kettle, the supported metal-solid acid catalyst is placed in a hydrogen atmosphere of 0.1 to 20MPa and reduced for 0.5 to 6 hours at the temperature of 180 to 300 ℃.
In other embodiments of the present invention, the reduction treatment comprises: in a tubular furnace, the supported metal-solid acid catalyst is placed in a normal pressure hydrogen atmosphere at the hydrogen flow rate of 10-200 ml/min, and is reduced for 0.5-6 h at the temperature of 300-600 ℃.
In some embodiments of the invention, the solvent comprises an alkane and/or water.
In some embodiments of the invention, the conditions of the hydrodeoxygenation reaction include: the temperature is 100-400 ℃, the hydrogen pressure is 0.1-20 MPa, the stirring speed is 100-2000 rpm, and the reaction time is 0-96 h.
In some embodiments of the invention, the naphthenic fuel comprises a naphthenic fuel in the range of C6 to C15; in some embodiments of the present invention, the naphthenic fuel includes at least one of gasoline, jet fuel, and diesel fuel.
In some embodiments of the invention, the naphthenic fuel may be a mixture, the naphthenic fuel comprising predominantly a mixture of naphthenes having a carbon number in the range of C6-C15; in some embodiments of the invention, the naphthenic fuel consists essentially of cyclohexane, isopropylcyclohexane, a C15 bicyclic product (e.g., the C15 bicyclic product may be of the formula
Etc.) and the like.
In another aspect of the present invention, the present invention provides a naphthenic fuel, which is prepared by the preparation method described above.
In order to better understand the present invention, the following examples are further provided to illustrate the present invention, but the present invention is not limited to the following examples.
Examples
Example 1
Step 1: preparation of supported metal-solid acid catalyst
Configuration of Ni (NO) 3 ) 2 Dropping the aqueous solution on HZSM-5 molecular sieve as carrier, si/Al 2 =25, drying at a temperature of around 65 ℃ for 12h to obtain supported metal-solid acid catalyst (labelled Ni/HSZM-5-1) with Ni loading of 5wt%.
Pre-reduction of a supported metal-solid acid catalyst: putting the dried catalyst into a tubular fixed bed reactor, and introducing H 2 And reducing at the high temperature of 500 ℃ for 2h, and cooling to room temperature to obtain the reduced Ni/HSZM-5-1 catalyst.
Step 2: production of naphthenic fuels
0.3g of aromatic oxygen-containing waste plastic PC and 0.1g of reduced Ni/HSZM-5-1 catalyst are put into a cooled reaction kettle, and then the reaction kettle is sealed. At 4MPa H 2 Reacting at 190 deg.C under 500rpm for 16h in atmosphere, wherein the Gas Chromatography (GC) diagram of the reaction product is shown in FIG. 1, the gas chromatography-mass spectrometry (GC-MS) diagram of the main product cyclohexane in the reaction product is shown in FIG. 2, and the main product isopropyl cyclohexyl in the reaction productThe GC-MS pattern of the alkane is shown in FIG. 3, and the GC-MS pattern of the main product, C15 bicyclic product, in the reaction product is shown in FIG. 4. After cooling, the aromatic oxygen-containing waste plastics PC are all converted to obtain the naphthenic fuels, wherein the total yield of the C6-C15 naphthenic hydrocarbons is 83.4 percent.
Example 2
Step 1: preparation of supported metal-solid acid catalyst
Configuration of Ni (NO) 3 ) 2 Dropping the aqueous solution on HZSM-5 molecular sieve as carrier, si/Al 2 =25, drying at a temperature around 65 ℃ for 12h, obtaining a supported metal-solid acid catalyst (labelled Ni/HSZM-5-2) with a Ni loading of 15wt%.
Pre-reducing the supported metal-solid acid catalyst, drying the catalyst in a tubular fixed bed reactor, and introducing H 2 Reducing for 2h at 500 ℃, and cooling to room temperature to obtain the reduced Ni/HSZM-5-2 catalyst.
Step 2: production of naphthenic fuels
0.3g of aromatic oxygen-containing waste plastic PC and 0.1g of reduced Ni/HSZM-5-2 catalyst are put into a cooled reaction kettle, and then the reaction kettle is sealed. At 4MPa H 2 The reaction is carried out for 16h at the rotation speed of 500rpm under the temperature of 190 ℃ in the atmosphere. After cooling, the aromatic oxygen-containing waste plastics PC are completely converted to obtain the naphthenic hydrocarbon fuel, wherein the total yield of the C6-C15 naphthenic hydrocarbon is 94.3 percent, and the yield of the aromatic alkane fuel is 1.7 percent.
Example 3
Step 1: preparation of supported metal-solid acid catalyst
Configuration of Ni (NO) 3 ) 2 Dropping the aqueous solution on HZSM-5 molecular sieve as carrier, si/Al 2 =25, drying at a temperature of around 65 ℃ for 12h, obtaining a supported metal-solid acid catalyst (labelled Ni/HSZM-5-3) with a Ni loading of 20wt%.
Pre-reducing a supported metal-solid acid catalyst: putting the dried catalyst into a tubular fixed bed reactor, and introducing H 2 Reducing for 2h at 500 ℃, and cooling to room temperature to obtain the reduced Ni/HSZM-5-3 catalyst.
Step 2: production of naphthenic fuels
0.3g of aromatic oxygen-containing waste plastic PC and 0.1g of reduced Ni/HSZM-5-3 catalyst are put into a cooled reaction kettle, and then the reaction kettle is sealed. At 4MPa H 2 The reaction is carried out for 16h at the rotation speed of 500rpm under the temperature of 190 ℃ in the atmosphere. After cooling, the aromatic oxygen-containing waste plastics PC are completely converted to obtain the naphthenic hydrocarbon fuel, wherein the total yield of the C6-C15 naphthenic hydrocarbon is 96.3 percent, and the total yield of the paraffinic hydrocarbon is 99.8 percent.
Example 4
Step 1: preparation of supported metal-solid acid catalyst
Configuration of Ni (NO) 3 ) 2 Dropping the aqueous solution on the carrier H-beta molecular sieve, the molecular sieve Si/Al 2 And =25, drying at a temperature of about 65 ℃ for 12H to obtain a supported metal-solid acid catalyst (labeled as Ni/H- β), wherein the Ni loading is 5wt%.
Pre-reduction of a supported metal-solid acid catalyst: putting the dried catalyst into a tubular fixed bed reactor, and introducing H 2 And reducing at high temperature, and cooling to room temperature to obtain the reduced Ni/H-beta catalyst.
And 2, step: production of naphthenic fuels
0.3g of aromatic oxygen-containing waste plastic PC and 0.1g of reduced Ni/H-beta catalyst are put into a cooled reaction kettle, and then the reaction kettle is sealed. At 4MPa H 2 The reaction is carried out for 16h at the rotation speed of 500rpm under the temperature of 190 ℃ in the atmosphere. After cooling, the aromatic oxygen-containing waste plastics PC are all converted to obtain the naphthenic fuels, wherein the total yield of the C6-C15 naphthenic hydrocarbons is 39.2 percent.
Example 5
Step 1: preparation of supported metal-solid acid catalyst
Configuration H 2 PtCl 6 And Ni (NO) 3 ) 2 Mixing the water solution uniformly, and dripping the mixture on a carrier HZSM-5 molecular sieve of Si/Al 2 =25, drying at about 65 ℃ for 12h to obtain a supported metal-solid acid catalyst (labeled Pt-Ni/HZSM-5) with Ni loading of 4.5wt% and Pt loading of 0.5wt%.
Pre-reduction of a supported metal-solid acid catalyst: putting the dried catalyst into a tubular fixed bed reactor, and introducing H 2 Reducing at high temperature, and cooling to room temperature to obtain the reduced Pt-Ni/HZSM-5 catalyst.
Step 2: production of naphthenic fuels
0.3g of aromatic oxygen-containing waste plastic PC and 0.1g of reduced Pt-Ni/HZSM-5 catalyst are put into a cooled reaction kettle, and then the reaction kettle is sealed. At 4MPa H 2 The reaction is carried out for 16h at the rotation speed of 500rpm under the temperature of 190 ℃ in the atmosphere. After cooling, the aromatic oxygen-containing waste plastics PC are completely converted to obtain the naphthenic fuel, wherein the total yield of the C6-C15 naphthenic is 94.2%.
Example 6
Step 1: preparation of supported metal-solid acid catalyst
Configuration of RuCl 3 And Ni (NO) 3 ) 2 Mixing the water solution uniformly, and dripping the mixture on a carrier HZSM-5 molecular sieve of Si/Al 2 =25, drying at about 65 ℃ for 12h to obtain a supported metal-solid acid catalyst (labeled as Ru-Ni/HZSM-5) with Ni loading of 4.5wt% and Ru loading of 0.5wt%.
Pre-reduction of a supported metal-solid acid catalyst: putting the dried catalyst into a tubular fixed bed reactor, and introducing H 2 And reducing at high temperature, and cooling to room temperature to obtain the reduced Ru-Ni/HZSM-5 catalyst.
Step 2: production of naphthenic fuels
0.3g of aromatic oxygen-containing waste plastic PC and 0.1g of reduced Ru-Ni/HZSM-5 catalyst are put into a cooled reaction kettle, and then the reaction kettle is sealed. At 4MPa H 2 The reaction is carried out for 16h at the rotation speed of 500rpm under the temperature of 190 ℃ in the atmosphere. After cooling, the aromatic oxygen-containing waste plastics PC are all converted to obtain the naphthenic fuels, wherein the total yield of the C6-C15 naphthenic hydrocarbons is 93.3 percent.
The above is not mentioned, is suitable for the prior art.
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above are not necessarily intended to refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Moreover, various embodiments or examples and features of various embodiments or examples described in this specification can be combined and combined by one skilled in the art without being mutually inconsistent.
While certain specific embodiments of the present invention have been described in detail by way of illustration, it will be understood by those skilled in the art that the foregoing is illustrative only and is not limiting of the scope of the invention, as various modifications or additions may be made to the specific embodiments described and substituted in a similar manner by those skilled in the art without departing from the scope of the invention as defined in the appending claims. It should be understood by those skilled in the art that any modifications, equivalents, improvements and the like made to the above embodiments in accordance with the technical spirit of the present invention are included in the scope of the present invention.
Claims (10)
1. A method for producing a naphthenic hydrocarbon fuel, comprising:
in the presence of a solvent, catalyzing aromatic oxygen-containing waste plastics by adopting a supported metal-solid acid catalyst to perform hydrodeoxygenation reaction to obtain the naphthenic hydrocarbon fuel;
wherein the supported metal-solid acid catalyst comprises an active metal and a solid acid support, the active metal being supported on the solid acid support;
the active metal comprises at least one of Ru, ir, pd, pt, rh, ni, fe, co and Cu; the solid acid carrier comprises at least one of zeolite molecular sieve, amorphous silicon-aluminum material, heteropoly acid, zirconium phosphate, zirconium tungstate, acidic clay, niobium phosphate, niobium pentoxide and acidic cation exchange resin.
2. The method of claim 1, wherein the zeolite molecular sieve comprises at least one of H-ZSM-5, H-Y, H-USY, H-beta, H-MOR, H-MCM-22, and H-SAPO molecular sieves.
3. The production method according to claim 1 or 2, characterized in that the active metal is contained in an amount of 0.1 to 50wt% based on the total mass of the supported metal-solid acid catalyst;
and/or the active metal is contained in an amount of 1 to 30wt% based on the total mass of the supported metal-solid acid catalyst.
4. The method according to claim 3, wherein the method for preparing the supported metal-solid acid catalyst comprises:
adding a metal soluble salt solution into the solid acid carrier for isovolumetric impregnation, then drying at 50-120 ℃ for 2-24 h, then roasting at 300-700 ℃ for 0-6 h to obtain the supported metal-solid acid catalyst,
wherein the metal in the metal soluble salt corresponds to the metal in the active metal.
5. The method according to claim 4, wherein the supported metal-solid acid catalyst is subjected to a reduction treatment before use;
and/or the reduction treatment comprises the following steps: in a batch type reaction kettle, the supported metal-solid acid catalyst is placed in a hydrogen atmosphere of 0.1 to 20MPa and reduced for 0.5 to 6 hours at the temperature of 180 to 300 ℃;
and/or the reduction treatment comprises the following steps: in a tubular furnace, the supported metal-solid acid catalyst is placed in a normal pressure hydrogen atmosphere at the hydrogen flow rate of 10-200 ml/min, and is reduced for 0.5-6 h at the temperature of 300-600 ℃.
6. The method of claim 1, wherein the solvent comprises an alkane and/or water.
7. The method of claim 1, wherein the aromatic oxygen-containing waste plastic comprises at least one of polycarbonate, polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene isophthalate, polyethylene naphthalate, polyetheretherketone, polyetherketone, polyetherketoneketone, polyetheretherketoneketone, polyetherketoneetherketoneketone, and polyphenylene ether.
8. The method according to claim 1, wherein the conditions of the hydrodeoxygenation reaction comprise: the temperature is 100-400 ℃, the hydrogen pressure is 0.1-20 MPa, the stirring speed is 100-2000 rpm, and the reaction time is 0-96 h.
9. The production method according to claim 1, wherein the naphthenic fuel includes a naphthenic fuel in a range of C6 to C15;
and/or, the naphthenic fuel comprises at least one of gasoline, jet fuel, and diesel fuel.
10. A naphthenic hydrocarbon fuel, characterized by being produced by the production method according to any one of claims 1 to 9.
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