NO126079B - - Google Patents

Download PDF

Info

Publication number: NO126079B
Authority: NO; Norway
Prior art keywords: dehydrogenation; catalyst; chain; paraffins; hydrocarbon
Prior art date: 1966-10-31

Application number

NO170320A

Other languages

English (en)

Norwegian (no)

Inventor

E Jones

Original Assignee

Universal Oil Prod Co

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.)

1966-10-31

Filing date

1967-10-30

Publication date

1972-12-18

1967-10-30 Application filed by Universal Oil Prod Co filed Critical Universal Oil Prod Co

1972-12-18 Publication of NO126079B publication Critical patent/NO126079B/no

Links

239000003054 catalyst Substances 0.000 claims description 51
238000006356 dehydrogenation reaction Methods 0.000 claims description 50
229930195733 hydrocarbon Natural products 0.000 claims description 30
150000002430 hydrocarbons Chemical class 0.000 claims description 29
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 22
239000004215 Carbon black (E152) Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 17
239000007788 liquid Substances 0.000 claims description 17
239000007858 starting material Substances 0.000 claims description 17
238000005804 alkylation reaction Methods 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
230000029936 alkylation Effects 0.000 claims description 12
230000002378 acidificating effect Effects 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
229910052697 platinum Inorganic materials 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
239000012190 activator Substances 0.000 claims description 8
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
239000007789 gas Substances 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
229910052785 arsenic Inorganic materials 0.000 claims description 5
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
229910010272 inorganic material Inorganic materials 0.000 claims description 4
230000002152 alkylating effect Effects 0.000 claims description 3
229910052787 antimony Inorganic materials 0.000 claims description 3
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
229910052797 bismuth Inorganic materials 0.000 claims description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
150000002484 inorganic compounds Chemical class 0.000 claims description 3
150000002736 metal compounds Chemical class 0.000 claims description 2
238000010348 incorporation Methods 0.000 claims 1
238000006263 metalation reaction Methods 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 17
150000001336 alkenes Chemical class 0.000 description 16
239000003599 detergent Substances 0.000 description 15
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 14
125000003118 aryl group Chemical group 0.000 description 14
150000005673 monoalkenes Chemical class 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
125000002877 alkyl aryl group Chemical group 0.000 description 10
150000001491 aromatic compounds Chemical class 0.000 description 10
239000002808 molecular sieve Substances 0.000 description 9
239000012188 paraffin wax Substances 0.000 description 9
239000010865 sewage Substances 0.000 description 9
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
239000002168 alkylating agent Substances 0.000 description 8
229940100198 alkylating agent Drugs 0.000 description 8
239000003350 kerosene Substances 0.000 description 8
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
-1 sodium sulphonate derivatives Chemical class 0.000 description 8
239000002689 soil Substances 0.000 description 8
229910000040 hydrogen fluoride Inorganic materials 0.000 description 7
239000000376 reactant Substances 0.000 description 7
238000000926 separation method Methods 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
238000006317 isomerization reaction Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001335 aliphatic alkanes Chemical class 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910017052 cobalt Inorganic materials 0.000 description 4
239000010941 cobalt Substances 0.000 description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
239000006260 foam Substances 0.000 description 4
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
229910000510 noble metal Inorganic materials 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000008188 pellet Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
239000011148 porous material Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001339 alkali metal compounds Chemical class 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
239000011733 molybdenum Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000004763 sulfides Chemical class 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
239000010937 tungsten Substances 0.000 description 2
WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
241001507939 Cormus domestica Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
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 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
239000002156 adsorbate Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000008953 bacterial degradation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000000404 calcium aluminium silicate Substances 0.000 description 1
235000012215 calcium aluminium silicate Nutrition 0.000 description 1
WNCYAPRTYDMSFP-UHFFFAOYSA-N calcium aluminosilicate Chemical compound [Al+3].[Al+3].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O WNCYAPRTYDMSFP-UHFFFAOYSA-N 0.000 description 1
229940078583 calcium aluminosilicate Drugs 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005485 electric heating Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
229910021476 group 6 element Inorganic materials 0.000 description 1
229910052735 hafnium Inorganic materials 0.000 description 1
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
239000008233 hard water Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
229910001947 lithium oxide Inorganic materials 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
239000010955 niobium Substances 0.000 description 1
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
239000010801 sewage sludge Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
229940075554 sorbate Drugs 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
230000008961 swelling Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000000271 synthetic detergent Substances 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
CXVCSRUYMINUSF-UHFFFAOYSA-N tetrathiomolybdate(2-) Chemical compound [S-][Mo]([S-])(=S)=S CXVCSRUYMINUSF-UHFFFAOYSA-N 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
- 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3335—Catalytic processes with metals
- C07C5/3337—Catalytic processes with metals of the platinum group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
- C07C2523/04—Alkali metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/18—Arsenic, antimony or bismuth
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/42—Platinum
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1206—Hydrogen fluoride

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

NO170320A 1966-10-31 1967-10-30 NO126079B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US59049066A	1966-10-31	1966-10-31

Publications (1)

Publication Number	Publication Date
NO126079B true NO126079B (de)	1972-12-18

Family

ID=24362479

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO170320A NO126079B (de)	1966-10-31	1967-10-30

Country Status (14)

Country	Link
US (1)	US3432567A (de)
AT (1)	AT297680B (de)
BE (1)	BE705591A (de)
CH (1)	CH509953A (de)
DE (1)	DE1668781C3 (de)
DK (1)	DK137121B (de)
ES (1)	ES346569A1 (de)
GB (1)	GB1193486A (de)
GR (1)	GR34474B (de)
IL (1)	IL28792A (de)
NL (1)	NL157585B (de)
NO (1)	NO126079B (de)
OA (1)	OA02526A (de)
YU (1)	YU36361B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3491162A (en) *	1968-04-03	1970-01-20	Universal Oil Prod Co	Catalytic dehydrogenation of contaminated normal paraffin hydrocarbons
US3681424A (en) *	1968-12-26	1972-08-01	Universal Oil Prod Co	Secondary alkyl sulfate detergent process
US3681442A (en) *	1968-12-26	1972-08-01	Universal Oil Prod Co	Alkylaromatic sulfonate detergent process of preparation
IN164101B (de) *	1984-04-04	1989-01-14	Uop Inc
US4914246A (en) *	1986-10-24	1990-04-03	Exxon Research & Engineering Company	Alkylphenols and derivatives thereof via phenol alkylation by cracked petroleum distillates
HUP0003855A3 (en) *	1997-08-08	2001-11-28	Procter & Gamble	Improved processes for making surfactants via adsorptive separation and products thereof
ITMI981631A1 (it) *	1998-07-16	2000-01-16	Condea Augusta Spa	Procedimento per la produzione di idrocarburi alchilaromatici lineari

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3126426A (en) *		1964-03-24		Hydrogfcnation
BE612036A (de) *
US2972644A (en) *	1956-11-14	1961-02-21	British Petroleum Co	Dehydrogenation or dehydrocyclization of non-aromatic hydrocarbons
US2964577A (en) *	1959-02-05	1960-12-13	Socony Mobil Oil Co Inc	Activation of metals for hydrocarbon dehydrogenation

1966
- 1966-10-31 US US590490A patent/US3432567A/en not_active Expired - Lifetime
1967
- 1967-10-17 GB GB47229/67A patent/GB1193486A/en not_active Expired
- 1967-10-17 GR GR670134474A patent/GR34474B/el unknown
- 1967-10-18 IL IL28792A patent/IL28792A/xx unknown
- 1967-10-24 DE DE1668781A patent/DE1668781C3/de not_active Expired
- 1967-10-24 AT AT962367A patent/AT297680B/de active
- 1967-10-25 BE BE705591D patent/BE705591A/xx not_active IP Right Cessation
- 1967-10-26 CH CH1497867A patent/CH509953A/de not_active IP Right Cessation
- 1967-10-26 NL NL6714536.A patent/NL157585B/xx not_active IP Right Cessation
- 1967-10-27 YU YU02094/67A patent/YU36361B/xx unknown
- 1967-10-27 OA OA53090A patent/OA02526A/xx unknown
- 1967-10-30 ES ES346569A patent/ES346569A1/es not_active Expired
- 1967-10-30 DK DK540167AA patent/DK137121B/da not_active IP Right Cessation
- 1967-10-30 NO NO170320A patent/NO126079B/no unknown

Also Published As

Publication number	Publication date
IL28792A (en)	1972-07-26
AT297680B (de)	1972-04-10
DE1668781A1 (de)	1971-03-25
NL157585B (nl)	1978-08-15
US3432567A (en)	1969-03-11
YU209467A (en)	1981-11-13
GR34474B (el)	1968-05-14
GB1193486A (en)	1970-06-03
YU36361B (en)	1983-06-30
DE1668781B2 (de)	1975-05-07
BE705591A (de)	1968-03-01
DK137121C (de)	1978-06-19
DK137121B (da)	1978-01-23
OA02526A (fr)	1970-05-05
ES346569A1 (es)	1969-04-16
NL6714536A (de)	1968-05-01
CH509953A (de)	1971-07-15
DE1668781C3 (de)	1976-01-08

Publication	Publication Date	Title
EP0929502B1 (de)	2001-08-01	Alkylierungsverfahren in dem zeolith beta verwendet wird
RU2276662C2 (ru)	2006-05-20	Способ получения углеводородов с высоким октановым числом исходя из смесей н-бутан/изобутан, таких как бутаны газовых месторождений, и смесь углеводородов с высоким октановым числом
US9328037B2 (en)	2016-05-03	Benzene alkylation using acidic ionic liquids
BRPI0822083B1 (pt)	2017-11-21	??? gasoline production process with octano index up to 95 and coproduction of aromatic bases ??
US3238249A (en)	1966-03-01	Alkylbenzene sulfonate production via n-olefin dimerization
US4128593A (en)	1978-12-05	Production and recovery of para-cymene
US3931350A (en)	1976-01-06	Process for producing alkylaromatics
US2656397A (en)	1953-10-20	Isomerization and separation of xylenes
US3681442A (en)	1972-08-01	Alkylaromatic sulfonate detergent process of preparation
US4692270A (en)	1987-09-08	Surface active agent
EP0160145A2 (de)	1985-11-06	Verfahren zur Alkylierung von Aromaten mit Hilfe eines amorphen Kieselsäure-/Tonerde-Katalysators mit grossen Poren
US3910994A (en)	1975-10-07	Alkylaromatic sulfonate detergent process
US3078318A (en)	1963-02-19	Production of specific xylene isomers
US4300008A (en)	1981-11-10	Preparation of 2,6-dimethyldecalin and its isomers
US3312734A (en)	1967-04-04	Preparation of biodegradable surfactants
WO2003062178A1 (en)	2003-07-31	Process for the utilization of refinery c4 streams
US3919339A (en)	1975-11-11	Hydrogenolysis/isomerization process
US3432567A (en)	1969-03-11	Alkylaryl production
GB2159832A (en)	1985-12-11	Process of upgrading of natural gasoline
WO2010048400A2 (en)	2010-04-29	Hexene upgrading
US4814545A (en)	1989-03-21	Process for removing impurities from an aromatic stream
US9688589B2 (en)	2017-06-27	Process for preparation of n-propyl benzene
US4735703A (en)	1988-04-05	Method of increasing the concentration of straight chain paraffin material
NO141829B (no)	1980-02-11	Generator for sterilt, utvaskbart radioaktivt materiale
US3494970A (en)	1970-02-10	Preparation of aryl-substituted normal paraffin hydrocarbons