CH410885A - Verfahren zur Alkylierung aromatischer Kohlenwasserstoffe - Google Patents

Verfahren zur Alkylierung aromatischer Kohlenwasserstoffe

Info

Publication number: CH410885A
Authority: CH; Switzerland
Prior art keywords: zone; alkylation; boron trifluoride; aromatic hydrocarbons; transalkylation
Prior art date: 1959-05-25

Application number

CH601560A

Other languages

German (de)

English (en)

Inventor

John Ward Dennis

Oliver Stine Laurence

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.)

1959-05-25

Filing date

1960-05-25

Publication date

1966-04-15

1960-05-25 Application filed by Universal Oil Prod Co filed Critical Universal Oil Prod Co

1966-04-15 Publication of CH410885A publication Critical patent/CH410885A/de

Links

238000005804 alkylation reaction Methods 0.000 title claims description 63
230000029936 alkylation Effects 0.000 title claims description 57
150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 45
238000000034 method Methods 0.000 title claims description 42
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 84
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 76
238000010555 transalkylation reaction Methods 0.000 claims description 52
229910015900 BF3 Inorganic materials 0.000 claims description 42
229940100198 alkylating agent Drugs 0.000 claims description 27
239000002168 alkylating agent Substances 0.000 claims description 27
-1 benzene hydrocarbons Chemical class 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
229930195733 hydrocarbon Natural products 0.000 claims description 20
239000000047 product Substances 0.000 claims description 20
239000003054 catalyst Substances 0.000 claims description 19
229910052809 inorganic oxide Inorganic materials 0.000 claims description 17
239000007788 liquid Substances 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 11
239000004215 Carbon black (E152) Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 6
150000005673 monoalkenes Chemical class 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 2
150000001491 aromatic compounds Chemical class 0.000 description 39
239000007789 gas Substances 0.000 description 30
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 26
239000005977 Ethylene Substances 0.000 description 26
150000002430 hydrocarbons Chemical class 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
150000001336 alkenes Chemical class 0.000 description 8
238000005194 fractionation Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
150000001555 benzenes Chemical class 0.000 description 6
229910052796 boron Inorganic materials 0.000 description 6
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
230000004048 modification Effects 0.000 description 6
238000012986 modification Methods 0.000 description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000463 material Substances 0.000 description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229920000098 polyolefin Polymers 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000002912 waste gas Substances 0.000 description 4
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
238000004064 recycling Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 2
CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
150000008051 alkyl sulfates Chemical class 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000013844 butane Nutrition 0.000 description 2
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000006698 induction Effects 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
JIRNEODMTPGRGV-UHFFFAOYSA-N pentadecylbenzene Chemical compound CCCCCCCCCCCCCCCC1=CC=CC=C1 JIRNEODMTPGRGV-UHFFFAOYSA-N 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000001294 propane Substances 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
BNXNQXKAEVKUJG-UHFFFAOYSA-N 1-Methyl-2-n-hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1C BNXNQXKAEVKUJG-UHFFFAOYSA-N 0.000 description 1
PQAHWOUEBKVMQH-UHFFFAOYSA-N 1-dodecyl-2-methylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1C PQAHWOUEBKVMQH-UHFFFAOYSA-N 0.000 description 1
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 1
WGCJTTUVWKJDAX-UHFFFAOYSA-N 1-fluoro-2-methylpropane Chemical compound CC(C)CF WGCJTTUVWKJDAX-UHFFFAOYSA-N 0.000 description 1
FCBJLBCGHCTPAQ-UHFFFAOYSA-N 1-fluorobutane Chemical compound CCCCF FCBJLBCGHCTPAQ-UHFFFAOYSA-N 0.000 description 1
JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 1
ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 description 1
GSMZLBOYBDRGBN-UHFFFAOYSA-N 2-fluoro-2-methylpropane Chemical compound CC(C)(C)F GSMZLBOYBDRGBN-UHFFFAOYSA-N 0.000 description 1
IXHWZHXLJJPXIS-UHFFFAOYSA-N 2-fluorobutane Chemical compound CCC(C)F IXHWZHXLJJPXIS-UHFFFAOYSA-N 0.000 description 1
PRNZBCYBKGCOFI-UHFFFAOYSA-N 2-fluoropropane Chemical compound CC(C)F PRNZBCYBKGCOFI-UHFFFAOYSA-N 0.000 description 1
ZLCSFXXPPANWQY-UHFFFAOYSA-N 3-ethyltoluene Chemical compound CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
150000001349 alkyl fluorides Chemical class 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000004951 benzene Polymers 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
UAMZXLIURMNTHD-UHFFFAOYSA-N dialuminum;magnesium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Al+3] UAMZXLIURMNTHD-UHFFFAOYSA-N 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
DEQLTFPCJRGSHW-UHFFFAOYSA-N hexadecylbenzene Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1 DEQLTFPCJRGSHW-UHFFFAOYSA-N 0.000 description 1
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
LIXVMPBOGDCSRM-UHFFFAOYSA-N nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1 LIXVMPBOGDCSRM-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
229940045681 other alkylating agent in atc Drugs 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Polymers [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 1
RQFVHGAXCJVPBZ-UHFFFAOYSA-N propylene pentamer Chemical compound CC=C.CC=C.CC=C.CC=C.CC=C RQFVHGAXCJVPBZ-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
238000013022 venting Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- 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
- C07C2/68—Catalytic processes with halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
- 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
- C07C2527/1213—Boron fluoride
- 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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CH601560A 1959-05-25 1960-05-25 Verfahren zur Alkylierung aromatischer Kohlenwasserstoffe CH410885A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US81557559A	1959-05-25	1959-05-25

Publications (1)

Publication Number	Publication Date
CH410885A true CH410885A (de)	1966-04-15

Family

ID=25218205

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH601560A CH410885A (de)	1959-05-25	1960-05-25	Verfahren zur Alkylierung aromatischer Kohlenwasserstoffe

Country Status (4)

Country	Link
CH (1)	CH410885A (da)
DK (1)	DK103014C (da)
ES (1)	ES258338A1 (da)
GB (1)	GB905051A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1277231B (de) *	1964-03-21	1968-09-12	Universal Oil Prod Co	Verfahren zur Herstellung von monoalkylierten aromatischen Kohlenwasserstoffen

1960
- 1960-05-23 GB GB18049/60A patent/GB905051A/en not_active Expired
- 1960-05-24 ES ES0258338A patent/ES258338A1/es not_active Expired
- 1960-05-24 DK DK203960AA patent/DK103014C/da active
- 1960-05-25 CH CH601560A patent/CH410885A/de unknown

Also Published As

Publication number	Publication date
DK103014C (da)	1965-11-08
GB905051A (en)	1962-09-05
ES258338A1 (es)	1960-11-16

Publication	Publication Date	Title
DE3879204T2 (de)	1993-06-17	Alkylierungs-/transalkylierungsverfahren zur selektiven herstellung von monoalkylierten aromatischen kohlenwasserstoffen.
CH422739A (de)	1966-10-31	Verfahren zum Alkylieren aromatischer Kohlenwasserstoffe
DE69705958T2 (de)	2002-04-04	Alkylierungsverfahren in dem zeolith beta verwendet wird
US4051191A (en)	1977-09-27	Solid phosphoric acid catalyzed alkylation of aromatic hydrocarbons
DE69911248T2 (de)	2004-06-09	Verbessertes verfahren zur alkylierung von aromaten
DE68923795T2 (de)	1996-03-28	Herstellung von alkylbenzolen.
DE69304687T2 (de)	1997-01-23	Verfahren zur Herstellung von Ethylbenzol
CH504392A (de)	1971-03-15	Verfahren zur Alkylierung von aromatischen Verbindungen und Anwendung des Verfahrens
DE69525075T2 (de)	2002-07-18	Verfahren zur herstellung von ethylbenzol oder von cumol
DE1643110B1 (de)	1972-02-03	Verfahren zur Herstellung monoalkylierter aromatischer Verbindungen
US4237328A (en)	1980-12-02	Process for HF-catalyzed alkylation of aromatic hydrocarbons
CH410885A (de)	1966-04-15	Verfahren zur Alkylierung aromatischer Kohlenwasserstoffe
DE3877646T2 (de)	1993-06-24	Verfahren zur herstellung von p-alkylstyrolen.
AT214424B (de)	1961-04-10	Verfahren zur kontinuierlichen Alkylierung aromatischer Kohlenwasserstoffe
DE1493285A1 (de)	1969-04-03	Verfahren zur Alkylierung von aromatischen Verbindungen
EP0337273B1 (de)	1993-09-22	Verfahren zur Ethylierung oder Propylierung von Benzol
AT220141B (de)	1962-03-12	Verfahren zur kontinuierlichen Monoalkylierung aromatischer Kohlenwasserstoffe
DE69800564T2 (de)	2001-06-21	Mehrstufiges Alkylierungsverfahren
AT215978B (de)	1961-07-10	Verfahren zur Alkylierung aromatischer Kohlenwasserstoffe
DE2401923A1 (de)	1974-07-18	Verfahren zur alkylierung von aromatischen verbindungen
DE1418446C (de)	1971-01-28	Verfahren zur Alkylierung von aroma tischen Kohlenwasserstoffen mit Olefinen
DE69101645T2 (de)	1994-07-28	Oktanverbesserungsverfahren.
DE60112196T2 (de)	2005-12-29	Verfahren zur Herstellung von monoalkylierten aromatischen Verbindungen
DE1768021C3 (de)	1980-03-06	Verfahren zur Herstellung alkylaromatischer Kohlenwasserstoffe
DE1280828B (de)	1968-10-24	Verfahren zur Alkylierung von aromatischen Kohlenwasserstoffen