NL193372C - Werkwijze voor het bereiden van paraxyleen uit tolueen en een methyleringsmiddel onder toepassing van een kristallijn-siliciumdioxidekatalysator, een kristallijn-siliciumdioxidekatalysator en een werkwijze voor het bereiden daarvan. - Google Patents
Werkwijze voor het bereiden van paraxyleen uit tolueen en een methyleringsmiddel onder toepassing van een kristallijn-siliciumdioxidekatalysator, een kristallijn-siliciumdioxidekatalysator en een werkwijze voor het bereiden daarvan. Download PDFInfo
- Publication number
- NL193372C NL193372C NL8002266A NL8002266A NL193372C NL 193372 C NL193372 C NL 193372C NL 8002266 A NL8002266 A NL 8002266A NL 8002266 A NL8002266 A NL 8002266A NL 193372 C NL193372 C NL 193372C
- Authority
- NL
- Netherlands
- Prior art keywords
- silica
- promoter
- catalyst
- oxide
- hours
- Prior art date
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims description 165
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title claims description 144
- 235000012239 silicon dioxide Nutrition 0.000 title claims description 79
- 239000003054 catalyst Substances 0.000 title claims description 75
- 229910002026 crystalline silica Inorganic materials 0.000 title claims description 45
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims description 26
- 239000012022 methylating agents Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 81
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 239000000377 silicon dioxide Substances 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 25
- 229910021488 crystalline silicon dioxide Inorganic materials 0.000 claims description 25
- 238000010438 heat treatment Methods 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 229910001868 water Inorganic materials 0.000 claims description 21
- 239000008096 xylene Substances 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 150000004706 metal oxides Chemical group 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- -1 alkaline earth metal carbonates Chemical class 0.000 claims description 9
- 229910052810 boron oxide Inorganic materials 0.000 claims description 7
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 238000001354 calcination Methods 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 6
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 6
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 6
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 5
- 229910000413 arsenic oxide Inorganic materials 0.000 claims description 5
- 229960002594 arsenic trioxide Drugs 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims description 5
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- KTTMEOWBIWLMSE-UHFFFAOYSA-N diarsenic trioxide Chemical group O1[As](O2)O[As]3O[As]1O[As]2O3 KTTMEOWBIWLMSE-UHFFFAOYSA-N 0.000 claims 3
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 52
- 238000000034 method Methods 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 239000012299 nitrogen atmosphere Substances 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 230000011987 methylation Effects 0.000 description 18
- 238000007069 methylation reaction Methods 0.000 description 18
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 16
- 150000002430 hydrocarbons Chemical class 0.000 description 15
- 239000004215 Carbon black (E152) Substances 0.000 description 14
- 239000012298 atmosphere Substances 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000010453 quartz Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000012018 catalyst precursor Substances 0.000 description 8
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 238000001994 activation Methods 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 230000001035 methylating effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000008119 colloidal silica Substances 0.000 description 3
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
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- 150000004756 silanes Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- IKWTVSLWAPBBKU-UHFFFAOYSA-N a1010_sial Chemical group O=[As]O[As]=O IKWTVSLWAPBBKU-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CCDWGDHTPAJHOA-UHFFFAOYSA-N benzylsilicon Chemical compound [Si]CC1=CC=CC=C1 CCDWGDHTPAJHOA-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 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
- 239000003085 diluting agent Substances 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 239000011148 porous material Substances 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Chemical compound [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
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- 239000005995 Aluminium silicate Substances 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- REDZBBAPPIPUBI-UHFFFAOYSA-N CCCCO.CCCCO.CCCCO.[AsH3] Chemical compound CCCCO.CCCCO.CCCCO.[AsH3] REDZBBAPPIPUBI-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
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- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
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- XVDGUXYOXCNUBD-UHFFFAOYSA-N benzyl(diphenyl)silicon Chemical compound C=1C=CC=CC=1C[Si](C=1C=CC=CC=1)C1=CC=CC=C1 XVDGUXYOXCNUBD-UHFFFAOYSA-N 0.000 description 1
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- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
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- RPEKTFIWNREKII-UHFFFAOYSA-N ethyl(3,3,3-trifluoropropyl)silicon Chemical compound CC[Si]CCC(F)(F)F RPEKTFIWNREKII-UHFFFAOYSA-N 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 229940102396 methyl bromide Drugs 0.000 description 1
- PDMYPTLGUMRHMI-UHFFFAOYSA-N methyl(3,3,3-trifluoropropyl)silicon Chemical compound C[Si]CCC(F)(F)F PDMYPTLGUMRHMI-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 238000002791 soaking Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- YGBFTDQFAKDXBZ-UHFFFAOYSA-N tributyl stiborite Chemical compound [Sb+3].CCCC[O-].CCCC[O-].CCCC[O-] YGBFTDQFAKDXBZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
-
- 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
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- 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
- B01J23/18—Arsenic, antimony or bismuth
-
- 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
- B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
- B01J29/035—Microporous crystalline materials not having base exchange properties, such as silica polymorphs, e.g. silicalites
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/865—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an ether
-
- 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
- B01J2229/12—After treatment, characterised by the effect to be obtained to alter the outside of the crystallites, e.g. selectivation
-
- 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
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/32—Reaction with silicon compounds, e.g. TEOS, siliconfluoride
-
- 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
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/42—Addition of matrix or binder particles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/03—Catalysts comprising molecular sieves not having base-exchange properties
- C07C2529/035—Crystalline silica polymorphs, e.g. silicalites
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3200179 | 1979-04-20 | ||
US06/032,001 US4444989A (en) | 1979-04-20 | 1979-04-20 | Methylation of toluene to para-xylene catalyzed by crystalline silica |
US06/129,272 US4283306A (en) | 1979-04-20 | 1980-03-26 | Crystalline silica and use in alkylation of aromatics |
US12927280 | 1980-03-26 |
Publications (3)
Publication Number | Publication Date |
---|---|
NL8002266A NL8002266A (nl) | 1980-10-22 |
NL193372B NL193372B (nl) | 1999-04-01 |
NL193372C true NL193372C (nl) | 1999-08-03 |
Family
ID=26707857
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8002266A NL193372C (nl) | 1979-04-20 | 1980-04-18 | Werkwijze voor het bereiden van paraxyleen uit tolueen en een methyleringsmiddel onder toepassing van een kristallijn-siliciumdioxidekatalysator, een kristallijn-siliciumdioxidekatalysator en een werkwijze voor het bereiden daarvan. |
Country Status (9)
Country | Link |
---|---|
US (1) | US4283306A (de) |
AU (1) | AU529021B2 (de) |
CA (1) | CA1144532A (de) |
DE (1) | DE3015037C2 (de) |
FR (1) | FR2454328B1 (de) |
GB (1) | GB2051853B (de) |
IT (1) | IT1141290B (de) |
MX (2) | MX153632A (de) |
NL (1) | NL193372C (de) |
Families Citing this family (84)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4518703A (en) * | 1979-02-16 | 1985-05-21 | Union Oil Company Of California | Crystalline silica catalysts |
US4565802A (en) * | 1979-02-16 | 1986-01-21 | Union Oil Company Of California | Silica-containing catalysts |
US4740651A (en) * | 1979-08-23 | 1988-04-26 | Amoco Corporation | Catalytic compositions and process uses |
US4428862A (en) | 1980-07-28 | 1984-01-31 | Union Oil Company Of California | Catalyst for simultaneous hydrotreating and hydrodewaxing of hydrocarbons |
US4387260A (en) * | 1981-04-20 | 1983-06-07 | Cosden Technology, Inc. | Alkylation of aromatic compounds with silicalite catalysts in the presence of steam |
US4362653A (en) | 1981-04-27 | 1982-12-07 | Uop Inc. | Hydrocarbon conversion catalyst |
US4877762A (en) * | 1981-05-26 | 1989-10-31 | Union Oil Company Of California | Catalyst for simultaneous hydrotreating and hydrodewaxing of hydrocarbons |
US4428825A (en) | 1981-05-26 | 1984-01-31 | Union Oil Company Of California | Catalytic hydrodewaxing process with added ammonia in the production of lubricating oils |
US4790927A (en) * | 1981-05-26 | 1988-12-13 | Union Oil Company Of California | Process for simultaneous hydrotreating and hydrodewaxing of hydrocarbons |
US4604371A (en) * | 1981-06-19 | 1986-08-05 | Union Oil Company Of California | Oxidation catalyst |
DE3267754D1 (en) * | 1981-06-19 | 1986-01-16 | Coal Industry Patents Ltd | Amorphous silica-based catalyst and process for its production |
US4562269A (en) * | 1981-12-07 | 1985-12-31 | Union Oil Company Of California | Method of producing maleic anhydride |
US4639530A (en) * | 1981-06-19 | 1987-01-27 | Union Oil Company Of California | Process for making maleic anhydride |
US4801567A (en) * | 1981-06-19 | 1989-01-31 | Union Oil Company Of California | Oxidation catalyst |
US4513090A (en) * | 1981-07-09 | 1985-04-23 | Exxon Research And Engineering Co. | Crystalline silica zeolite-containing catalyst |
US4599477A (en) * | 1981-08-03 | 1986-07-08 | Union Oil Company Of California | Oxidative-dehydrogenation process |
US4564603A (en) * | 1981-12-07 | 1986-01-14 | Union Oil Company Of California | Oxidative-dehydrogenation catalyst and process |
US4455388A (en) * | 1981-12-07 | 1984-06-19 | Union Oil Company Of California | Catalyst and process for producing diolefins |
US4567314A (en) * | 1981-12-07 | 1986-01-28 | Union Oil Company Of California | Process for producing diolefins |
US4782166A (en) * | 1981-12-30 | 1988-11-01 | Union Oil Company Of California | Process for producing maleic anhydride utilizing a catalyst containing a siliceous metal-containing crystalline composition |
US4776946A (en) * | 1981-12-30 | 1988-10-11 | Union Oil Company Of California | Hydrodewaxing process utilizing a catalyst containing a siliceous metal-containing crystalline composition |
US4842720A (en) * | 1981-12-30 | 1989-06-27 | Union Oil Company Of California | Fischer-Tropsch synthesis process utilizing a catalyst containing a siliceous metal-containing crystalline composition |
US4520220A (en) * | 1982-02-22 | 1985-05-28 | Cosden Technology, Inc. | Alkylation of aromatics employing silicalite catalysts |
US4490570A (en) * | 1982-02-22 | 1984-12-25 | Cosden Technology, Inc. | Method for para selective alkylation employing silicalite catalysts |
US4489214A (en) * | 1982-03-01 | 1984-12-18 | Cosden Technology, Inc. | Production of ortho-suppressed dialkyl benzenes |
US4618738A (en) * | 1982-03-09 | 1986-10-21 | Union Oil Company Of California | Hydrocarbon conversion process with catalytically active amorphous silica |
US4501925A (en) * | 1982-03-09 | 1985-02-26 | Union Oil Company Of California | Chemical reaction promoted by catalytically active amorphous silica |
US4513158A (en) * | 1982-03-09 | 1985-04-23 | Union Oil Company Of California | Polymerization and oligomerization with catalytically active amorphous silica |
US4481102A (en) * | 1982-03-09 | 1984-11-06 | Union Oil Company Of California | Cracking with catalytically active amorphous silica |
US4548705A (en) * | 1982-03-09 | 1985-10-22 | Union Oil Company Of California | Hydrocracking with catalytically active amorphous silica and zeolites |
US4400570A (en) * | 1982-05-21 | 1983-08-23 | Cosden Technology, Inc. | Ethylbenzene production employing tea-silicate catalysts |
CA1196617A (en) * | 1982-07-14 | 1985-11-12 | George E. Morris | Catalyst composition, method for its production and its use in the production of hydrocarbons from synthesis gas |
US4560675A (en) * | 1982-08-13 | 1985-12-24 | Uop Inc. | Adsorbent for separating fatty acids from rosin acids |
US4452909A (en) * | 1982-09-13 | 1984-06-05 | E. I. Du Pont De Nemours And Company | Process for coating crystalline silica polymorphs |
DE3377793D1 (en) * | 1982-10-19 | 1988-09-29 | Idemitsu Kosan Co | Process for the production of para-xylene |
AU2508384A (en) * | 1983-02-28 | 1984-09-06 | E.I. Du Pont De Nemours And Company | Crystaline silica polymorphs and preparation method |
US4732747A (en) * | 1983-04-11 | 1988-03-22 | The Dow Chemical Company | Magnesium silicate compositions and process for making |
US4451686A (en) * | 1983-05-09 | 1984-05-29 | Cosden Technology, Inc. | Dehydrogenation process |
US4801364A (en) * | 1983-07-15 | 1989-01-31 | Uop | Separation and conversion processes using metal aluminophosphates |
US4570027A (en) * | 1984-04-27 | 1986-02-11 | Exxon Research And Engineering Co. | Alkylation of aromatic molecules using a silica-alumina catalyst derived from zeolite |
US4758327A (en) * | 1984-06-21 | 1988-07-19 | Union Oil Company Of California | Shock calcined crystalline silica catalysts |
US4623636A (en) | 1984-06-21 | 1986-11-18 | Union Oil Company Of California | Shock calcined crystalline silica catalysts |
US4582694A (en) * | 1984-06-21 | 1986-04-15 | Union Oil Company Of California | Shock calcined crystalline silica catalysts |
US4623530A (en) * | 1985-02-20 | 1986-11-18 | United States Steel Corporation | Crystalline magnesia-silica composites and process for producing same |
US4683334A (en) * | 1985-04-30 | 1987-07-28 | E. I. Du Pont De Nemours & Company | Modified 8-ring zeolites as catalysts for conversion of methanol and ammonia to dimethylamine |
DK507686D0 (da) * | 1985-10-24 | 1986-10-23 | Monsanto Co | Katalysatorbaerer, fremgangsmaade til oxidation af so2 til so3 samt katalysator til anvendelse herved |
US4670617A (en) * | 1985-12-30 | 1987-06-02 | Amoco Corporation | Propylation of toluene with a high surface area, zinc-modified, crystalline silica molecular sieve |
US4751340A (en) * | 1986-06-16 | 1988-06-14 | Union Carbide Corporation | Selective production of para-aromatics |
US4761513A (en) * | 1987-07-01 | 1988-08-02 | Uop Inc. | Temperature control for aromatic alkylation process |
US4843057A (en) * | 1988-03-29 | 1989-06-27 | E. I. Du Pont De Nemours And Company | Preparation of promoted silica catalysts |
US5043502A (en) * | 1990-03-16 | 1991-08-27 | Uop | Production of xylenes from light aliphatic hydrocarbons via dehydrocyclodimerization and methylation |
EP0555798B1 (de) * | 1992-02-13 | 1999-05-06 | Becton, Dickinson and Company | Celithydrat und Reinigung von DNS |
US5498814A (en) * | 1992-03-12 | 1996-03-12 | Mobil Oil Corp. | Regioselective methylation of toluene to para-xylene |
US5321183A (en) * | 1992-03-12 | 1994-06-14 | Mobil Oil Corp. | Process for the regioselective conversion of aromatics to para-disubstituted benzenes |
US5475179A (en) * | 1992-03-12 | 1995-12-12 | Mobil Oil | Regioselective production of para-dialkyl benzenes |
US5365003A (en) * | 1993-02-25 | 1994-11-15 | Mobil Oil Corp. | Shape selective conversion of hydrocarbons over extrusion-modified molecular sieve |
US5349113A (en) * | 1993-02-25 | 1994-09-20 | Mobil Oil Corp. | Shape selective hydrocarbon conversion over pre-selectivated, activated catalyst |
US5349114A (en) * | 1993-04-05 | 1994-09-20 | Mobil Oil Corp. | Shape selective hydrocarbon conversions over modified catalyst |
US5371312A (en) * | 1993-04-05 | 1994-12-06 | Mobil Oil Corp. | Shape selective hydrocarbon conversions over modified catalyst |
US5698756A (en) * | 1993-05-28 | 1997-12-16 | Mobil Oil Corporation | Toluene alkylation with ethylene to produce para-ethyloluene |
US6576582B1 (en) | 1993-05-28 | 2003-06-10 | Exxonmobil Oil Corporation | Binderless ex situ selectivated zeolite catalyst |
US5659098A (en) * | 1993-05-28 | 1997-08-19 | Beck; Jeffrey S. | High conversion touluene disproportionation with ex situ selectivated zeolite catalysts |
ES2185657T3 (es) * | 1993-05-28 | 2003-05-01 | Exxonmobil Oil Corp | Procedimiento para modificar la selectividad por la forma de un catalizador de zeolita y uso del catalizador modificado. |
US5476823A (en) * | 1993-05-28 | 1995-12-19 | Mobil Oil Corp. | Method of preparation of ex situ selectivated zeolite catalysts for enhanced shape selective applications and method to increase the activity thereof |
US5365004A (en) * | 1993-05-28 | 1994-11-15 | Mobil Oil Corp. | Selective toluene disproportionation process (STDP) with ex situ selectivated zeolite catalysts |
US5403800A (en) * | 1993-05-28 | 1995-04-04 | Mobil Oil Corp. | Multiple impregnation technique for the preparation of ex situ selectivated zeolite catalysts |
US5530170A (en) * | 1993-05-28 | 1996-06-25 | Mobil Oil Corporation | Ethylbenzene alkylation with ethylene to produce para-diethylbenzene |
US5406015A (en) * | 1993-05-28 | 1995-04-11 | Mobil Oil Corp. | Selective ethylbenzene disproportionation processes (SEBDP) with ex situ selectivated zeolite catalyst |
US5367099A (en) * | 1993-05-28 | 1994-11-22 | Mobil Oil Corp. | Selective toluene disproportionation process (STDP) with ex situ selectivated zeolite catalyst |
US5382737A (en) * | 1993-05-28 | 1995-01-17 | Mobil Oil Corp. | Selective ethylbenzene disproportionation process (SEBDP) with ex situ selectivated zeolite catalysts |
US5726114A (en) * | 1993-10-27 | 1998-03-10 | Mobil Oil Corporation | Method of preparation of ex situ selectivated zeolite catalysts for enhanced shape selective applications and methods to increase the activity thereof |
US5488194A (en) * | 1994-05-16 | 1996-01-30 | Mobil Oil Corp. | Selective production of para-dialkyl substituted benzenes and catalyst therefor |
US5625104A (en) * | 1995-06-06 | 1997-04-29 | Mobil Oil Corporation | Alkali metal ion exchanged selectivated zeolite catalyst |
US5849968A (en) * | 1995-06-06 | 1998-12-15 | Mobil Oil Corporation | Hydrocarbon conversion process with alkaline earth metal ion exchanged selectivated zeolite catalyst |
US5773679A (en) * | 1995-12-26 | 1998-06-30 | Mobil Oil Corporation | Performance enhancement of zeolite catalysts with water cofeed |
US6066770A (en) * | 1998-11-05 | 2000-05-23 | Phillips Petroleum Company | Selectivated zeolitic hydrocarbon conversion catalyst |
US6864200B2 (en) | 2001-01-23 | 2005-03-08 | Indian Petrochemicals Corporation Limited | Selectivated metallosilicate catalyst composite for alkylaromatic conversion, process for the preparation thereof, and use thereof in hydrocarbon conversion |
US7176339B2 (en) * | 2002-06-19 | 2007-02-13 | Exxonmobil Chemical Patents Inc. | Manufacture of xylenes using reformate |
US7119239B2 (en) * | 2002-06-19 | 2006-10-10 | Exxonmobil Chemical Patents Inc. | Manufacture of xylenes using reformate |
CN100428996C (zh) * | 2005-09-29 | 2008-10-29 | 南京工业大学 | 一种增强对位选择性的甲苯歧化沸石催化剂制备方法 |
US7648933B2 (en) | 2006-01-13 | 2010-01-19 | Dynamic Abrasives Llc | Composition comprising spinel crystals, glass, and calcium iron silicate |
US8609567B2 (en) * | 2009-12-16 | 2013-12-17 | Uop Llc | OCP catalyst with improved steam tolerance |
CN105283415B (zh) | 2013-06-13 | 2017-07-21 | 埃克森美孚化学专利公司 | 甲苯歧化催化剂的原位修饰焦炭选择性去活化 |
CN104447158A (zh) * | 2013-09-24 | 2015-03-25 | 中国石油化工股份有限公司 | 生产二甲苯的方法 |
Family Cites Families (10)
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US3941871A (en) | 1973-11-02 | 1976-03-02 | Mobil Oil Corporation | Crystalline silicates and method of preparing the same |
US4038211A (en) * | 1973-12-17 | 1977-07-26 | National Distillers And Chemical Corporation | Olefin hydration catalyst |
US4002698A (en) * | 1975-08-19 | 1977-01-11 | Mobil Oil Corporation | Methylation of toluene in the presence of a phosphorus-modified activated crystalline aluminosilicate catalyst |
NZ178543A (en) * | 1974-09-23 | 1978-04-03 | Mobil Oil Corp | Conversion catalyst, crystalline alumin osilicate zeolite containing phosphorus |
US4064070A (en) * | 1974-12-23 | 1977-12-20 | Chevron Research Company | Catalyst for producing maleic anhydride |
US4061724A (en) * | 1975-09-22 | 1977-12-06 | Union Carbide Corporation | Crystalline silica |
US4034053A (en) * | 1975-12-08 | 1977-07-05 | Mobil Oil Corporation | Selective production of para-xylene |
US4090981A (en) * | 1976-09-23 | 1978-05-23 | Mobile Oil Corporation | Catalyst for selective production of para dialkyl substituted benzenes |
GB1548567A (en) * | 1976-06-30 | 1979-07-18 | Ici Ltd | Production of xylenes |
US4073865A (en) * | 1976-09-27 | 1978-02-14 | Union Carbide Corporation | Silica polymorph and process for preparing same |
-
1980
- 1980-03-26 US US06/129,272 patent/US4283306A/en not_active Expired - Lifetime
- 1980-04-09 AU AU57271/80A patent/AU529021B2/en not_active Expired
- 1980-04-11 GB GB8011974A patent/GB2051853B/en not_active Expired
- 1980-04-15 CA CA000349878A patent/CA1144532A/en not_active Expired
- 1980-04-17 MX MX182001A patent/MX153632A/es unknown
- 1980-04-17 MX MX203949A patent/MX173883B/es unknown
- 1980-04-18 FR FR8008747A patent/FR2454328B1/fr not_active Expired
- 1980-04-18 DE DE3015037A patent/DE3015037C2/de not_active Expired - Lifetime
- 1980-04-18 IT IT21517/80A patent/IT1141290B/it active
- 1980-04-18 NL NL8002266A patent/NL193372C/nl not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
IT8021517A0 (it) | 1980-04-18 |
DE3015037C2 (de) | 1993-11-04 |
FR2454328A1 (fr) | 1980-11-14 |
FR2454328B1 (fr) | 1985-10-31 |
IT1141290B (it) | 1986-10-01 |
NL8002266A (nl) | 1980-10-22 |
GB2051853B (en) | 1983-02-09 |
DE3015037A1 (de) | 1980-10-30 |
MX173883B (es) | 1994-04-07 |
NL193372B (nl) | 1999-04-01 |
AU529021B2 (en) | 1983-05-19 |
US4283306A (en) | 1981-08-11 |
CA1144532A (en) | 1983-04-12 |
AU5727180A (en) | 1980-10-23 |
GB2051853A (en) | 1981-01-21 |
MX153632A (es) | 1986-12-09 |
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