DE2463421C2 - Verfahren zur Herstellung von aromatischen Kohlenwasserstoffen - Google Patents
Verfahren zur Herstellung von aromatischen KohlenwasserstoffenInfo
- Publication number
- DE2463421C2 DE2463421C2 DE2463421A DE2463421A DE2463421C2 DE 2463421 C2 DE2463421 C2 DE 2463421C2 DE 2463421 A DE2463421 A DE 2463421A DE 2463421 A DE2463421 A DE 2463421A DE 2463421 C2 DE2463421 C2 DE 2463421C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- zsm
- methanol
- zeolite
- conversion
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 25
- 230000008569 process Effects 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 239000010457 zeolite Substances 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 47
- 230000015572 biosynthetic process Effects 0.000 claims description 37
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 36
- 238000003786 synthesis reaction Methods 0.000 claims description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 35
- 229910021536 Zeolite Inorganic materials 0.000 claims description 27
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000377 silicon dioxide Substances 0.000 claims description 17
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 16
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 9
- 229910052680 mordenite Inorganic materials 0.000 claims description 8
- 239000002803 fossil fuel Substances 0.000 claims description 7
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000007789 gas Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 29
- 229930195733 hydrocarbon Natural products 0.000 description 26
- 150000002430 hydrocarbons Chemical class 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- 239000011148 porous material Substances 0.000 description 17
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 15
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- -1 aliphatic organic compounds Chemical class 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000003502 gasoline Substances 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000003079 shale oil Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 229910002090 carbon oxide Inorganic materials 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000002309 gasification Methods 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002898 organic sulfur compounds Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000007669 thermal treatment Methods 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910004283 SiO 4 Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229910052675 erionite Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910001657 ferrierite group Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910002535 CuZn Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910017706 MgZn Inorganic materials 0.000 description 1
- 229910002847 PtSn Inorganic materials 0.000 description 1
- 229910002796 Si–Al Inorganic materials 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 241000711825 Viral hemorrhagic septicemia virus Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- JEWHCPOELGJVCB-UHFFFAOYSA-N aluminum;calcium;oxido-[oxido(oxo)silyl]oxy-oxosilane;potassium;sodium;tridecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.[Na].[Al].[K].[Ca].[O-][Si](=O)O[Si]([O-])=O JEWHCPOELGJVCB-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 1
- 239000003830 anthracite Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052663 cancrinite Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910001567 cementite Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 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
- 239000000356 contaminant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011990 functional testing Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001683 gmelinite Inorganic materials 0.000 description 1
- 229910052677 heulandite Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052674 natrolite Inorganic materials 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002006 petroleum coke Substances 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- 229910001743 phillipsite Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052665 sodalite Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052678 stilbite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
-
- 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
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
-
- 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
-
- 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
- B01J29/405—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 rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
-
- 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
- B01J29/44—Noble metals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- Chemical & Material Sciences (AREA)
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- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
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Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38722073A | 1973-08-09 | 1973-08-09 | |
US387223A US3894107A (en) | 1973-08-09 | 1973-08-09 | Conversion of alcohols, mercaptans, sulfides, halides and/or amines |
US387222A US3894106A (en) | 1973-08-09 | 1973-08-09 | Conversion of ethers |
US387224A US3907915A (en) | 1973-08-09 | 1973-08-09 | Conversion of carbonyl compounds to aromatics |
US387219A US3894104A (en) | 1973-08-09 | 1973-08-09 | Aromatization of hetero-atom substituted hydrocarbons |
US387221A US3894105A (en) | 1973-08-09 | 1973-08-09 | Production of durene |
US387218A US3894103A (en) | 1973-08-09 | 1973-08-09 | Aromatization reactions |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2463421C2 true DE2463421C2 (de) | 1986-10-02 |
Family
ID=27569739
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2463421A Expired DE2463421C2 (de) | 1973-08-09 | 1974-08-08 | Verfahren zur Herstellung von aromatischen Kohlenwasserstoffen |
DE2463420A Expired DE2463420C2 (de) | 1973-08-09 | 1974-08-08 | Verfahren zur Herstellung von im wesentlichen aus aliphatischen Kohlenwasserstoffen bestehenden Reaktionsprodukten |
DE19742463419 Pending DE2463419A1 (enrdf_load_stackoverflow) | 1973-08-09 | 1974-08-08 | |
DE2438252A Expired DE2438252C2 (de) | 1973-08-09 | 1974-08-08 | Verfahren zur Herstellung von Kohlenwasserstoffen durch katalytische Umwandlung von Methanol und/oder Dimethyläther |
DE2463418A Expired DE2463418C2 (de) | 1973-08-09 | 1974-08-08 | Verfahren zur Herstellung von im wesentlichen aliphatische, sauerstofffreie Kohlenwasserstoffe umfassenden Reaktionsprodukten |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2463420A Expired DE2463420C2 (de) | 1973-08-09 | 1974-08-08 | Verfahren zur Herstellung von im wesentlichen aus aliphatischen Kohlenwasserstoffen bestehenden Reaktionsprodukten |
DE19742463419 Pending DE2463419A1 (enrdf_load_stackoverflow) | 1973-08-09 | 1974-08-08 | |
DE2438252A Expired DE2438252C2 (de) | 1973-08-09 | 1974-08-08 | Verfahren zur Herstellung von Kohlenwasserstoffen durch katalytische Umwandlung von Methanol und/oder Dimethyläther |
DE2463418A Expired DE2463418C2 (de) | 1973-08-09 | 1974-08-08 | Verfahren zur Herstellung von im wesentlichen aliphatische, sauerstofffreie Kohlenwasserstoffe umfassenden Reaktionsprodukten |
Country Status (13)
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
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US3894102A (en) * | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Conversion of synthesis gas to gasoline |
NZ178543A (en) | 1974-09-23 | 1978-04-03 | Mobil Oil Corp | Conversion catalyst, crystalline alumin osilicate zeolite containing phosphorus |
US4025576A (en) * | 1975-04-08 | 1977-05-24 | Mobil Oil Corporation | Process for manufacturing olefins |
FR2313437A1 (fr) | 1975-04-08 | 1976-12-31 | Mobil Oil | Procede de conversion de charbon en essence a indice d'octane eleve |
US4016218A (en) * | 1975-05-29 | 1977-04-05 | Mobil Oil Corporation | Alkylation in presence of thermally modified crystalline aluminosilicate catalyst |
GB1526461A (en) * | 1975-07-02 | 1978-09-27 | Mobil Oil Corp | Manufacture of gasoline |
US4279830A (en) * | 1977-08-22 | 1981-07-21 | Mobil Oil Corporation | Conversion of synthesis gas to hydrocarbon mixtures utilizing dual reactors |
CA1117455A (en) * | 1977-12-20 | 1982-02-02 | Mobil Oil Corporation | Manufacture of lube base stock oil |
NL176933C (nl) * | 1978-04-21 | 1985-07-01 | Shell Int Research | Werkwijze voor de bereiding van een aromatisch koolwaterstofmengsel uit methanol. |
NL181001C (nl) * | 1978-05-30 | 1987-06-01 | Shell Int Research | Werkwijze voor de bereiding van aromatische koolwaterstoffen uit alifatische zuurstofbevattende verbindingen. |
US4205052A (en) * | 1979-02-01 | 1980-05-27 | Mobil Oil Corporation | Manufacture of synthetic mordenite |
US4205053A (en) * | 1979-02-01 | 1980-05-27 | Mobil Oil Corporation | Manufacture of nitrogenous zeolites |
US4197418A (en) * | 1979-03-01 | 1980-04-08 | Mobil Oil Corporation | Heat disposed in lower alcohols and derivatives conversion to gasoline hydrocarbons in a crystaline zeolite fluidized bed |
ZA801758B (en) * | 1979-04-04 | 1981-03-25 | Mobil Oil Corp | Steam-resistant zeolite catalyst |
DE3061930D1 (en) * | 1979-12-31 | 1983-03-17 | Mobil Oil Corp | Conversion of olefin containing mixtures to gasoline |
AU540104B2 (en) * | 1980-01-10 | 1984-11-01 | Mobil Oil Corp. | Calytic reforming |
US4394300A (en) | 1980-04-07 | 1983-07-19 | Mobil Oil Corporation | Zeolite catalyst modified with group IVB metal |
US4278827A (en) * | 1980-04-07 | 1981-07-14 | Mobil Oil Corporation | Shape selective reactions with zeolite catalyst modified with group IVB metal |
IN155637B (enrdf_load_stackoverflow) * | 1980-04-11 | 1985-02-16 | Imp Chemical Ind Plc Formerly | |
GB2075357A (en) * | 1980-05-09 | 1981-11-18 | Coal Industry Patents Ltd | Catalysts for the condensation of oxygenated organic compounds to give hydrocarbons |
US4302619A (en) * | 1980-06-04 | 1981-11-24 | Mobil Oil Corporation | Control of CO emissions in a process for producing gasoline from methanol |
JPS5712092A (en) * | 1980-06-26 | 1982-01-21 | Mitsubishi Heavy Ind Ltd | Recovering method for by-product water in synthesis of aromatic hydrocarbon mixture |
JPS57190081A (en) * | 1981-05-18 | 1982-11-22 | Res Assoc Petroleum Alternat Dev<Rapad> | Conversion of lower aliphatic oxygen compound into hydrocarbon |
NZ202811A (en) * | 1981-12-23 | 1984-12-14 | Mobil Oil Corp | Converting fossil fuel to hydrocarbon mixture rich in benzene,toluene and xylene |
JPS5997523A (ja) * | 1982-11-24 | 1984-06-05 | Agency Of Ind Science & Technol | アルカリ土類金属含有ゼオライト及びその製法 |
DD230545A3 (de) * | 1983-11-18 | 1985-12-04 | Akad Wissenschaften Ddr | Verfahren zur herstellung von niederen olefinen und aromaten |
LU85515A1 (fr) * | 1984-08-28 | 1986-03-11 | Belge Etat | Catalyseurs pour la transformation d'ethanol en ethylene et leur utilisation |
US5276240A (en) * | 1991-10-18 | 1994-01-04 | Board Of Regents, The University Of Texas System | Catalytic hydrodehalogenation of polyhalogenated hydrocarbons |
US9255227B2 (en) | 2006-12-13 | 2016-02-09 | Haldor Topsoe A/S | Process for the synthesis of hydrocarbon constituents of gasoline |
RU2472840C2 (ru) * | 2007-03-08 | 2013-01-20 | Вайрент, Инк. | Синтез жидкого топлива и химических реактивов из кислородсодержащих углеводородов |
ES2446542T3 (es) * | 2007-03-08 | 2014-03-10 | Virent, Inc. | Síntesis de combustibles líquidos y compuestos químicos a partir de hidrocarburos oxigenados |
CN101778808B (zh) * | 2007-08-13 | 2014-01-08 | 沙特基础工业公司 | 用于将脂族含氧化合物转化成芳族化合物的催化剂组合物和方法 |
JP5098704B2 (ja) * | 2008-03-04 | 2012-12-12 | 国立大学法人北海道大学 | ケトン類からオレフィンを製造するための触媒 |
JP5504494B2 (ja) * | 2009-03-02 | 2014-05-28 | 国立大学法人 鹿児島大学 | 芳香族炭化水素又はケトン化合物を製造する装置 |
WO2010101120A1 (ja) * | 2009-03-02 | 2010-09-10 | 国立大学法人 鹿児島大学 | 芳香族炭化水素又はケトン化合物を製造する装置/レブリン酸の製造装置、レブリン酸の分離装置及びレブリン酸から炭化水素を製造する装置 |
EP2576734B1 (en) * | 2010-06-03 | 2016-01-27 | Stora Enso Oyj | Hydrogen treatment of impure tall oil for the production of aromatic monomers |
RU2458898C1 (ru) * | 2011-02-18 | 2012-08-20 | Общество с ограниченной ответственностью Производственный научно-технический центр "ЭОН" (ООО ПНТЦ "ЭОН") | Способ получения ароматических углеводородов |
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US9440892B2 (en) * | 2013-03-14 | 2016-09-13 | Virent, Inc. | Production of aromatics from di- and polyoxygenates |
WO2014190124A1 (en) | 2013-05-22 | 2014-11-27 | Virent, Inc. | Hydrogenation of carboxylic acids to increase yield of aromatics |
US9873836B2 (en) | 2013-05-22 | 2018-01-23 | Virent, Inc. | Process for converting biomass to aromatic hydrocarbons |
US10196325B2 (en) | 2015-01-15 | 2019-02-05 | Exxonmobil Chemical Patents Inc. | Process for converting syngas to aromatics and catalyst system suitable therefor |
RU2594564C1 (ru) * | 2015-05-18 | 2016-08-20 | Федеральное государственное бюджетное учреждение науки Ордена Трудового Красного Знамени Институт нефтехимического синтеза им. А.В. Топчиева Российской академии наук (ИНХС РАН) | Катализатор и способ конверсии этанола, метанола или их смеси |
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US2950332A (en) * | 1958-11-26 | 1960-08-23 | Exxon Research Engineering Co | Conversion of ketones to aromatics |
US3728408A (en) * | 1969-05-05 | 1973-04-17 | Mobil Oil Corp | Conversion of polar compounds using highly siliceous zeolite-type catalysts |
-
1974
- 1974-08-02 CS CS745525A patent/CS191916B2/cs unknown
- 1974-08-05 FR FR7427086A patent/FR2240281B1/fr not_active Expired
- 1974-08-06 NL NLAANVRAGE7410583,A patent/NL181104C/xx not_active IP Right Cessation
- 1974-08-08 DE DE2463421A patent/DE2463421C2/de not_active Expired
- 1974-08-08 DE DE2463420A patent/DE2463420C2/de not_active Expired
- 1974-08-08 DE DE19742463419 patent/DE2463419A1/de active Pending
- 1974-08-08 DE DE2438252A patent/DE2438252C2/de not_active Expired
- 1974-08-08 IT IT26129/74A patent/IT1019796B/it active
- 1974-08-08 DE DE2463418A patent/DE2463418C2/de not_active Expired
- 1974-08-08 NO NO74742859A patent/NO145758C/no unknown
- 1974-08-08 DK DK422074A patent/DK422074A/da not_active Application Discontinuation
- 1974-08-09 GB GB3517774A patent/GB1446522A/en not_active Expired
- 1974-08-09 PL PL1974173365A patent/PL94448B1/pl unknown
- 1974-08-09 SU SU742056621A patent/SU589903A3/ru active
- 1974-08-09 BE BE147488A patent/BE818708A/xx not_active IP Right Cessation
- 1974-08-09 JP JP49090895A patent/JPS599525B2/ja not_active Expired
-
1977
- 1977-12-31 MY MY1977175A patent/MY7700175A/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2950332A (en) * | 1958-11-26 | 1960-08-23 | Exxon Research Engineering Co | Conversion of ketones to aromatics |
US3728408A (en) * | 1969-05-05 | 1973-04-17 | Mobil Oil Corp | Conversion of polar compounds using highly siliceous zeolite-type catalysts |
Also Published As
Publication number | Publication date |
---|---|
NO145758C (no) | 1982-06-02 |
NL7410583A (nl) | 1975-02-11 |
DE2463420C2 (de) | 1986-10-02 |
FR2240281B1 (enrdf_load_stackoverflow) | 1978-03-24 |
NO742859L (enrdf_load_stackoverflow) | 1975-03-10 |
IT1019796B (it) | 1977-11-30 |
SU589903A3 (ru) | 1978-01-25 |
MY7700175A (en) | 1977-12-31 |
DE2463419A1 (enrdf_load_stackoverflow) | 1985-02-28 |
DK422074A (enrdf_load_stackoverflow) | 1975-04-14 |
AU7215474A (en) | 1976-02-12 |
NL181104B (nl) | 1987-01-16 |
JPS599525B2 (ja) | 1984-03-03 |
DE2463418C2 (de) | 1987-02-19 |
CS191916B2 (en) | 1979-07-31 |
BE818708A (fr) | 1975-02-10 |
DE2438252C2 (de) | 1986-08-28 |
NL181104C (nl) | 1987-06-16 |
NO145758B (no) | 1982-02-15 |
JPS5076027A (enrdf_load_stackoverflow) | 1975-06-21 |
GB1446522A (en) | 1976-08-18 |
DE2438252A1 (de) | 1975-02-20 |
PL94448B1 (pl) | 1977-08-31 |
FR2240281A1 (enrdf_load_stackoverflow) | 1975-03-07 |
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