CA1075268A - Procede de transformation d'hydrocarbures aromatiques - Google Patents

Procede de transformation d'hydrocarbures aromatiques

Info

Publication number: CA1075268A
Authority: CA; Canada
Prior art keywords: catalyst; tif4; temperature; aromatic hydrocarbon; hours
Prior art date: 1977-09-13
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

CA286,610A

Other languages

English (en)

Inventor

Ji-Yong Ryu

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.)

Honeywell UOP LLC

Original Assignee

UOP LLC

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.)

1977-09-13

Filing date

1977-09-13

Publication date

1980-04-08

1977-09-13 Application filed by UOP LLC filed Critical UOP LLC

1977-09-13 Priority to CA286,610A priority Critical patent/CA1075268A/fr

1980-04-08 Application granted granted Critical

1980-04-08 Publication of CA1075268A publication Critical patent/CA1075268A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 20
150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 15
238000006243 chemical reaction Methods 0.000 title abstract description 18
239000003054 catalyst Substances 0.000 claims abstract description 64
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 21
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 20
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims abstract description 13
229910044991 metal oxide Inorganic materials 0.000 claims abstract description 8
150000004706 metal oxides Chemical class 0.000 claims abstract description 8
229940100198 alkylating agent Drugs 0.000 claims abstract description 7
239000002168 alkylating agent Substances 0.000 claims abstract description 7
229910003074 TiCl4 Inorganic materials 0.000 claims abstract 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 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 description 27
XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 claims description 23
239000010936 titanium Substances 0.000 claims description 13
229910010342 TiF4 Inorganic materials 0.000 claims description 12
239000000243 solution Substances 0.000 claims description 12
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 10
229910052719 titanium Inorganic materials 0.000 claims description 10
230000029936 alkylation Effects 0.000 claims description 9
238000005804 alkylation reaction Methods 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
239000012298 atmosphere Substances 0.000 claims description 5
150000001336 alkenes Chemical group 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 2
-1 ethylene, propylene Chemical group 0.000 claims description 2
239000007789 gas Substances 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
238000009997 thermal pre-treatment Methods 0.000 claims description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
239000012159 carrier gas Substances 0.000 claims 1
239000000017 hydrogel Substances 0.000 claims 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
239000003495 polar organic solvent Substances 0.000 claims 1
239000008096 xylene Substances 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 8
239000002131 composite material Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000007669 thermal treatment Methods 0.000 description 5
230000000694 effects Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000000859 sublimation Methods 0.000 description 4
230000008022 sublimation Effects 0.000 description 4
DFYVBMBVJVMTOU-UHFFFAOYSA-J [N].[Ti](Cl)(Cl)(Cl)Cl Chemical compound [N].[Ti](Cl)(Cl)(Cl)Cl DFYVBMBVJVMTOU-UHFFFAOYSA-J 0.000 description 3
239000011651 chromium Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
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 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000008246 gaseous mixture Substances 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
238000012360 testing method Methods 0.000 description 2
150000003609 titanium compounds Chemical class 0.000 description 2
238000011282 treatment Methods 0.000 description 2
KKIGDGWHHNXWNM-UHFFFAOYSA-N 1,2,3-tripropylbenzene Chemical compound CCCC1=CC=CC(CCC)=C1CCC KKIGDGWHHNXWNM-UHFFFAOYSA-N 0.000 description 1
VPHBYBUYWBZLEX-UHFFFAOYSA-N 1,2-dipropylbenzene Chemical compound CCCC1=CC=CC=C1CCC VPHBYBUYWBZLEX-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
241001050985 Disco Species 0.000 description 1
229910003708 H2TiF6 Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
150000001845 chromium compounds Chemical class 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
238000003795 desorption Methods 0.000 description 1
AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 1
229910001195 gallium oxide Inorganic materials 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910003437 indium oxide Inorganic materials 0.000 description 1
PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000011356 non-aqueous organic solvent Substances 0.000 description 1
WKMKTIVRRLOHAJ-UHFFFAOYSA-N oxygen(2-);thallium(1+) Chemical compound [O-2].[Tl+].[Tl+] WKMKTIVRRLOHAJ-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910003438 thallium oxide Inorganic materials 0.000 description 1
238000010555 transalkylation reaction Methods 0.000 description 1

Landscapes

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

CA286,610A 1977-09-13 1977-09-13 Procede de transformation d'hydrocarbures aromatiques Expired CA1075268A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA286,610A CA1075268A (fr)	1977-09-13	1977-09-13	Procede de transformation d'hydrocarbures aromatiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA286,610A CA1075268A (fr)	1977-09-13	1977-09-13	Procede de transformation d'hydrocarbures aromatiques

Publications (1)

Publication Number	Publication Date
CA1075268A true CA1075268A (fr)	1980-04-08

Family

ID=4109515

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA286,610A Expired CA1075268A (fr)	1977-09-13	1977-09-13	Procede de transformation d'hydrocarbures aromatiques

Country Status (1)

Country	Link
CA (1)	CA1075268A (fr)

1977
- 1977-09-13 CA CA286,610A patent/CA1075268A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-04-08	MKEX	Expiry

Publication	Publication Date	Title
JP3831821B2 (ja)	2006-10-11	接触水素化方法およびこの方法において使用可能な触媒
US4126645A (en)	1978-11-21	Selective hydrogenation of highly unsaturated hydrocarbons in the presence of less unsaturated hydrocarbons
US2773844A (en)	1956-12-11	Method for making supported silver catalysts
US2837587A (en)	1958-06-03	Purification of olefin-rich feed prior to polymerization
EP0206044B1 (fr)	1990-02-28	Procédé pour la conversion oxydante de composés organiques
KR100449965B1 (ko)	2004-12-13	선택적수소화반응촉매및그촉매를사용하는방법
US3644565A (en)	1972-02-22	Alkylation process
RU2108861C1 (ru)	1998-04-20	Способ активации каталитической композиции на основе соединения галлия и оксида алюминия и каталитическая композиция для дегидрирования с2 - с5-парафинов
DE68904372T2 (de)	1993-06-09	Verfahren zur selektiven oligomerisierung von olefinen und katalysator fuer ein solches verfahren.
US2658059A (en)	1953-11-03	Ethylene polymerization in the vapor phase
US3738977A (en)	1973-06-12	Polymerization of ethylene with a supported palladium catalyst
AU718621B2 (en)	2000-04-20	Process for preparing a catalyst suitable for use in isomerising hydrocarbons, the catalyst thus obtained, and its use
US4048248A (en)	1977-09-13	Process and catalyst for the conversion of aromatic hydrocarbons
US3836594A (en)	1974-09-17	Hydrocarbon conversion process and silica and/or alumina-containing catalyst therefor
CA1274254A (fr)	1990-09-18	Production de 1,5,9-tetradecatriene a forte teneur en isomeres (z,z)
CA1075268A (fr)	1980-04-08	Procede de transformation d'hydrocarbures aromatiques
US3014899A (en)	1961-12-26	Reduced group valpha metal oxide on silica/alumina support
CA1091700A (fr)	1980-12-16	No translation available
EP0180362A1 (fr)	1986-05-07	Composés organométalliques sur support destinés à la purification de fluides
GB1602460A (en)	1981-11-11	Process for the alkylation of aromatic hydrocarbons
US4239872A (en)	1980-12-16	Olefine polymerization with supported catalysts
US4048247A (en)	1977-09-13	Process for the conversion of aromatic hydrocarbons
US3163682A (en)	1964-12-29	Hydrogenation employing supported nickel and chromium containing metallo-organic catalysts
US5600054A (en)	1997-02-04	Process for the skeleton isomerization of linear olefins
US3072627A (en)	1963-01-08	Polymerization with a catalyst of an alkali metal chromate on silicaalumina