CA1061769A - Catalyseur a base de phosphore, preparation et utilisation - Google Patents

Catalyseur a base de phosphore, preparation et utilisation

Info

Publication number: CA1061769A
Authority: CA; Canada
Prior art keywords: phosphorus; zeolite; catalyst; process according; weight
Prior art date: 1974-09-23
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

Application number

CA235,939A

Other languages

English (en)

Other versions

CA235939S (en

Inventor

Stephen A. Butter

Warren W. Kaeding

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mobil Oil AS

Original Assignee

Mobil Oil AS

Priority date (The priority date 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 date listed.)

1974-09-23

Filing date

1975-09-22

Publication date

1979-09-04

1974-09-23 Priority claimed from US508306A external-priority patent/US3906054A/en

1974-09-23 Priority claimed from US508307A external-priority patent/US3911041A/en

1974-09-23 Priority claimed from US05/508,308 external-priority patent/US3972832A/en

1975-01-06 Priority claimed from US05/538,666 external-priority patent/US3965208A/en

1975-09-22 Application filed by Mobil Oil AS filed Critical Mobil Oil AS

1979-09-04 Application granted granted Critical

1979-09-04 Publication of CA1061769A publication Critical patent/CA1061769A/fr

Status Expired legal-status Critical Current

Links

229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 289
239000011574 phosphorus Substances 0.000 title claims abstract description 286
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 283
238000002360 preparation method Methods 0.000 title abstract description 12
239000010457 zeolite Substances 0.000 claims abstract description 306
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 277
239000003054 catalyst Substances 0.000 claims abstract description 272
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 260
238000006243 chemical reaction Methods 0.000 claims abstract description 162
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 49
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 43
239000000377 silicon dioxide Substances 0.000 claims abstract description 23
229910000323 aluminium silicate Inorganic materials 0.000 claims abstract description 15
150000002894 organic compounds Chemical class 0.000 claims abstract description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 339
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 265
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 112
239000000203 mixture Substances 0.000 claims description 89
238000000034 method Methods 0.000 claims description 73
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 49
230000008569 process Effects 0.000 claims description 45
229910001868 water Inorganic materials 0.000 claims description 45
150000001336 alkenes Chemical class 0.000 claims description 43
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 34
238000005804 alkylation reaction Methods 0.000 claims description 32
229930195733 hydrocarbon Natural products 0.000 claims description 30
150000002430 hydrocarbons Chemical class 0.000 claims description 30
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 29
229910052725 zinc Inorganic materials 0.000 claims description 29
239000011701 zinc Substances 0.000 claims description 29
238000010438 heat treatment Methods 0.000 claims description 28
230000029936 alkylation Effects 0.000 claims description 25
239000013078 crystal Substances 0.000 claims description 21
-1 ethylene, propylene Chemical group 0.000 claims description 20
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 19
239000004215 Carbon black (E152) Substances 0.000 claims description 17
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 17
239000002168 alkylating agent Substances 0.000 claims description 15
229940100198 alkylating agent Drugs 0.000 claims description 15
239000000376 reactant Substances 0.000 claims description 15
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 12
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 12
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 10
239000012022 methylating agents‎ Substances 0.000 claims description 10
230000011987 methylation Effects 0.000 claims description 10
238000007069 methylation reaction Methods 0.000 claims description 10
150000003751 zinc Chemical class 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 8
XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 claims description 7
238000001035 drying Methods 0.000 claims description 7
229940050176 methyl chloride Drugs 0.000 claims description 7
239000012188 paraffin wax Substances 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 6
239000011159 matrix material Substances 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
235000011007 phosphoric acid Nutrition 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000012071 phase Substances 0.000 claims description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
229910002651 NO3 Inorganic materials 0.000 claims description 3
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
230000009471 action Effects 0.000 claims description 3
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 3
229940077445 dimethyl ether Drugs 0.000 claims description 3
JIKVJUUIMIGAAO-UHFFFAOYSA-N diphenylphosphinous acid Chemical compound C=1C=CC=CC=1P(O)C1=CC=CC=C1 JIKVJUUIMIGAAO-UHFFFAOYSA-N 0.000 claims description 3
229940102396 methyl bromide Drugs 0.000 claims description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
239000007791 liquid phase Substances 0.000 claims description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
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239000000047 product Substances 0.000 description 103
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 70
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125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 47
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QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 36
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238000011282 treatment Methods 0.000 description 21
239000002904 solvent Substances 0.000 description 20
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 19
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 17
230000003197 catalytic effect Effects 0.000 description 17
239000008096 xylene Substances 0.000 description 17
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
230000004913 activation Effects 0.000 description 15
238000001994 activation Methods 0.000 description 15
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 15
125000001931 aliphatic group Chemical group 0.000 description 14
238000004458 analytical method Methods 0.000 description 14
150000003738 xylenes Chemical class 0.000 description 14
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 13
239000001257 hydrogen Substances 0.000 description 13
229910052739 hydrogen Inorganic materials 0.000 description 13
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 13
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 13
125000003118 aryl group Chemical group 0.000 description 12
239000011230 binding agent Substances 0.000 description 12
239000011148 porous material Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 10
150000001768 cations Chemical class 0.000 description 10
239000002131 composite material Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
229940058172 ethylbenzene Drugs 0.000 description 9
239000000463 material Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 9
150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
235000013844 butane Nutrition 0.000 description 8
238000001354 calcination Methods 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
230000007423 decrease Effects 0.000 description 8
238000010348 incorporation Methods 0.000 description 8
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
239000001294 propane Substances 0.000 description 8
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 8
239000000470 constituent Substances 0.000 description 7
238000005470 impregnation Methods 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
239000008188 pellet Substances 0.000 description 6
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
230000008901 benefit Effects 0.000 description 5
239000001273 butane Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
230000003247 decreasing effect Effects 0.000 description 5
238000004821 distillation Methods 0.000 description 5
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 5
239000012535 impurity Substances 0.000 description 5
238000010926 purge Methods 0.000 description 5
230000008929 regeneration Effects 0.000 description 5
238000011069 regeneration method Methods 0.000 description 5
239000012808 vapor phase Substances 0.000 description 5
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 4
PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
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229910000147 aluminium phosphate Inorganic materials 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000001491 aromatic compounds Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
239000007792 gaseous phase Substances 0.000 description 4
239000001307 helium Substances 0.000 description 4
229910052734 helium Inorganic materials 0.000 description 4
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
230000004048 modification Effects 0.000 description 4
238000012986 modification Methods 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
229910052710 silicon Inorganic materials 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000012360 testing method Methods 0.000 description 4
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
238000002441 X-ray diffraction Methods 0.000 description 3
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
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230000001419 dependent effect Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
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150000002892 organic cations Chemical class 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
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238000001179 sorption measurement Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 3
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XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
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MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
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101100305864 Alteromonas mediterranea (strain DSM 17117 / CIP 110805 / LMG 28347 / Deep ecotype) rph2 gene Proteins 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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NHEULQMXMXIOJY-UHFFFAOYSA-N Cl[PH2]=O Chemical class Cl[PH2]=O NHEULQMXMXIOJY-UHFFFAOYSA-N 0.000 description 1
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241000282326 Felis catus Species 0.000 description 1
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JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241001214257 Mene Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
241000022563 Rema Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
241000193803 Therea Species 0.000 description 1
101100135363 Yarrowia lipolytica (strain CLIB 122 / E 150) RIM101 gene Proteins 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000005600 alkyl phosphonate group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
JYIBXUUINYLWLR-UHFFFAOYSA-N aluminum;calcium;potassium;silicon;sodium;trihydrate Chemical compound O.O.O.[Na].[Al].[Si].[K].[Ca] JYIBXUUINYLWLR-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000001454 anthracenes Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
OOSPDKSZPPFOBR-UHFFFAOYSA-N butyl dihydrogen phosphite Chemical compound CCCCOP(O)O OOSPDKSZPPFOBR-UHFFFAOYSA-N 0.000 description 1
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239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
NDDSMIZUPBHSCL-UHFFFAOYSA-N chloro hypochlorite;phenylphosphane Chemical compound ClOCl.PC1=CC=CC=C1 NDDSMIZUPBHSCL-UHFFFAOYSA-N 0.000 description 1
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical class OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
229910001603 clinoptilolite Inorganic materials 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
RDXABLXNTVBVML-UHFFFAOYSA-N diethoxyphosphanyl diethyl phosphite Chemical compound CCOP(OCC)OP(OCC)OCC RDXABLXNTVBVML-UHFFFAOYSA-N 0.000 description 1
ZUKLAAHCPUBQLQ-UHFFFAOYSA-N diethylphosphinous acid Chemical compound CCP(O)CC ZUKLAAHCPUBQLQ-UHFFFAOYSA-N 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
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230000003292 diminished effect Effects 0.000 description 1
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BEQVQKJCLJBTKZ-UHFFFAOYSA-N diphenylphosphinic acid Chemical compound C=1C=CC=CC=1P(=O)(O)C1=CC=CC=C1 BEQVQKJCLJBTKZ-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012013 faujasite Substances 0.000 description 1
229910001657 ferrierite group Inorganic materials 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052677 heulandite Inorganic materials 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
NFMHSPWHNQRFNR-UHFFFAOYSA-N hyponitrous acid Chemical compound ON=NO NFMHSPWHNQRFNR-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
108010052322 limitin Proteins 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052680 mordenite Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000005504 petroleum refining Methods 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical class PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000010025 steaming Methods 0.000 description 1
229910052678 stilbite Inorganic materials 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
230000001629 suppression Effects 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
FHYUCVWDMABHHH-UHFFFAOYSA-N toluene;1,2-xylene Chemical group CC1=CC=CC=C1.CC1=CC=CC=C1C FHYUCVWDMABHHH-UHFFFAOYSA-N 0.000 description 1
238000000844 transformation Methods 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1

Landscapes

Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA235,939A 1974-09-23 1975-09-22 Catalyseur a base de phosphore, preparation et utilisation Expired CA1061769A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US508306A US3906054A (en)	1974-09-23	1974-09-23	Alkylation of olefins
US508307A US3911041A (en)	1974-09-23	1974-09-23	Conversion of methanol and dimethyl ether
US05/508,308 US3972832A (en)	1974-09-23	1974-09-23	Phosphorus-containing zeolite catalyst
US05/538,666 US3965208A (en)	1975-01-06	1975-01-06	Methylation of toluene

Publications (1)

Publication Number	Publication Date
CA1061769A true CA1061769A (fr)	1979-09-04

Family

ID=27504470

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA235,939A Expired CA1061769A (fr)	1974-09-23	1975-09-22	Catalyseur a base de phosphore, preparation et utilisation

Country Status (1)

Country	Link
CA (1)	CA1061769A (fr)

1975
- 1975-09-22 CA CA235,939A patent/CA1061769A/fr not_active Expired

Publication	Publication Date	Title
US4746763A (en)	1988-05-24	Process for producing aromatic compounds from C2 -C6 aliphatic hydrocarbons
US3972832A (en)	1976-08-03	Phosphorus-containing zeolite catalyst
CA1103703A (fr)	1981-06-23	Traduction non-disponible
CA1077455A (fr)	1980-05-13	Catalyseur a teneur d'antimoine, methode de preparation et emploi
US4044065A (en)	1977-08-23	Conversion utilizing a phosphorus-containing zeolite catalyst
US4499314A (en)	1985-02-12	Methanol conversion to hydrocarbons with zeolites and cocatalysts
US4554260A (en)	1985-11-19	Two stage process for improving the catalyst life of zeolites in the synthesis of lower olefins from alcohols and their ether derivatives
US4638106A (en)	1987-01-20	Two stage process for improving the catalyst life of zeolites in the synthesis of lower olefins from alcohols and their ether derivatives
CA2218869C (fr)	2005-07-12	Procede de preparation d'ethylbenzene ou de ses derives substitues
US4113788A (en)	1978-09-12	Selective production of para-xylene
RU2375337C2 (ru)	2009-12-10	Способ превращения кислородсодержащих соединений в пропилен с селективной гидроочисткой рециркулирующего потока тяжелых олефинов
JPS5815443B2 (ja)	1983-03-25	結晶性アルミノシリケ−トゼオライトの製法
CA2350957A1 (fr)	2001-03-29	Procede de conversion de methanol ou de dimethylether en olefines
US3906054A (en)	1975-09-16	Alkylation of olefins
CN101417235A (zh)	2009-04-29	一种甲苯甲醇烷基化制对二甲苯和低碳烯烃移动床催化剂
KR102888050B1 (ko)	2025-11-21	메소다공성 촉매 화합물 및 이의 용도
EP0014545B1 (fr)	1983-03-09	Méthode de préparation d'une composition catalytique zéolitique de sélectivité quant à la forme et de stabilité thermique améliorées et son utilisation dans un procédé catalytique de conversion d'hydrocarbures
CA1173865A (fr)	1984-09-04	Procede industriel
CA1122228A (fr)	1982-04-20	Reaction selective de composes benzeniques 1,4-disubstitues
US7393990B2 (en)	2008-07-01	Production of light olefins from oxygenate using framework gallium-containing medium pore molecular sieve
US4962266A (en)	1990-10-09	Process to convert linear alkanes
JPS60222428A (ja)	1985-11-07	炭化水素の接触転化法
Shibata et al.	1986	Transformation of propene into aromatic hydrocarbons over ZSM-5 zeolites
JPH0748573A (ja)	1995-02-21	合成結晶アルミノケイ酸塩および石油化学プロセスで炭化水素を触媒反応させる方法
EP0243129B1 (fr)	1990-06-06	Production d'hydrocarbures non saturés par craquage sélectif