CH397621A - Verfahren zur Entalkylierung von alkylaromatischen Kohlenwasserstoffen - Google Patents

Verfahren zur Entalkylierung von alkylaromatischen Kohlenwasserstoffen

Info

Publication number: CH397621A
Authority: CH; Switzerland
Prior art keywords: dealkylation; sulfur; benzene; weight; toluene
Prior art date: 1961-06-19

Application number

CH734062A

Other languages

German (de)

English (en)

Inventor

Roy Herber Raymond

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.)

1961-06-19

Filing date

1962-06-19

Publication date

1965-08-31

1962-06-19 Application filed by Universal Oil Prod Co filed Critical Universal Oil Prod Co

1965-08-31 Publication of CH397621A publication Critical patent/CH397621A/de

Links

230000020335 dealkylation Effects 0.000 title claims description 12
238000006900 dealkylation reaction Methods 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 12
-1 alkyl aromatic hydrocarbons Chemical class 0.000 title claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 16
150000002430 hydrocarbons Chemical class 0.000 claims description 16
150000003464 sulfur compounds Chemical class 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 6
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
238000004140 cleaning Methods 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 21
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
239000007788 liquid Substances 0.000 description 12
239000007789 gas Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 7
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
235000010290 biphenyl Nutrition 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
238000011084 recovery Methods 0.000 description 4
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229910000423 chromium oxide Inorganic materials 0.000 description 2
239000004927 clay Substances 0.000 description 2
239000000571 coke Substances 0.000 description 2
230000017858 demethylation Effects 0.000 description 2
238000010520 demethylation reaction Methods 0.000 description 2
LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
238000009826 distribution Methods 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
239000012263 liquid product Substances 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
239000002699 waste material Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
239000005967 1,4-Dimethylnaphthalene Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
PVPLWTZXLXLQHI-UHFFFAOYSA-N [O-2].[Al+3].[Si+4].[Zr+4] Chemical compound [O-2].[Al+3].[Si+4].[Zr+4] PVPLWTZXLXLQHI-UHFFFAOYSA-N 0.000 description 1
YAIQCYZCSGLAAN-UHFFFAOYSA-N [Si+4].[O-2].[Al+3] Chemical compound [Si+4].[O-2].[Al+3] YAIQCYZCSGLAAN-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 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
238000004517 catalytic hydrocracking Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000005194 ethylbenzenes Chemical class 0.000 description 1
229920001038 ethylene copolymer Polymers 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
229940078552 o-xylene Drugs 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007670 refining Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 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
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 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
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

CH734062A 1961-06-19 1962-06-19 Verfahren zur Entalkylierung von alkylaromatischen Kohlenwasserstoffen CH397621A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US11819261A	1961-06-19	1961-06-19

Publications (1)

Publication Number	Publication Date
CH397621A true CH397621A (de)	1965-08-31

Family

ID=22377048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH734062A CH397621A (de)	1961-06-19	1962-06-19	Verfahren zur Entalkylierung von alkylaromatischen Kohlenwasserstoffen

Country Status (5)

Country	Link
CH (1)	CH397621A (da)
DE (1)	DE1493277A1 (da)
DK (1)	DK108672C (da)
ES (1)	ES278427A1 (da)
GB (1)	GB982522A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2002368299A1 (en) *	2002-10-24	2004-05-13	Aleksandr Olegovich Naumenko	Method for producing benzene from benzene and /or alkylbenzene-containing mixtures having a high content of sulphur-containing substances

1962
- 1962-06-16 DE DE19621493277 patent/DE1493277A1/de active Pending
- 1962-06-18 GB GB2328462A patent/GB982522A/en not_active Expired
- 1962-06-18 ES ES278427A patent/ES278427A1/es not_active Expired
- 1962-06-18 DK DK270762A patent/DK108672C/da active
- 1962-06-19 CH CH734062A patent/CH397621A/de unknown

Also Published As

Publication number	Publication date
DE1493277A1 (de)	1969-04-10
GB982522A (en)	1965-02-03
ES278427A1 (es)	1962-12-16
DK108672C (da)	1968-01-29

Publication	Publication Date	Title
DE2526887C2 (de)	1986-09-18	Verfahren zur Herstellung von aromatischen Kohlenwasserstoffen
DE2441516A1 (de)	1975-03-20	Xylolisomerisierung
US4101597A (en)	1978-07-18	Recovery of p-xylene and benzene from eight carbon atom aromatic fractions
DE69836155T2 (de)	2007-08-30	Verfahren zur Alkylierung von Benzol
BRPI0711657A2 (pt)	2011-11-29	processo para isomerizar xilenos
DE2706853A1 (de)	1977-08-25	Verbundverfahren zur xylolabtrennung und toluoltransalkylierung
DE69315403T2 (de)	1998-04-09	Verfahren zur Herstellung von linearen Alkylbenzolen
DE2400034C2 (de)	1983-02-17	Verfahren zur Entfernung von C&darr;4&darr;-Acetylenen aus Kohlenwasserstoff-Einsatzgemischen
DE1273510B (de)	1968-07-25	Verfahren zur Gewinnung von Naphthalin
ITMI981631A1 (it)	2000-01-16	Procedimento per la produzione di idrocarburi alchilaromatici lineari
DE1273509B (de)	1968-07-25	Verfahren zur Gewinnung von Naphthalin
US4247729A (en)	1981-01-27	Process for producing high purity benzene
CH397621A (de)	1965-08-31	Verfahren zur Entalkylierung von alkylaromatischen Kohlenwasserstoffen
DE3876917T2 (de)	1993-05-06	Verfahren zur erzeugung von dimethylnaphthalenen.
DE69001702T2 (de)	1993-10-14	Katalysatorzusammensetzung, Verfahren zum Kracken von Nichtaromaten und Verfahren zum Isomerisieren von C8-aromatischen Kohlenwasserstoffen.
DE1054624B (de)	1959-04-09	Verfahren zur Dehydrocyclisierung und Dehydrierung von ganz oder teilweise aus nichtaromatischen Kohlenwasserstoffen bestehenden Ausgangsmaterialien
DE1270017B (de)	1968-06-12	Verfahren zur Gewinnung von hochgereinigtem Benzol
US2913393A (en)	1959-11-17	Process for upgrading of straight run gasolines by a combination of catalytic reforming and isomerization
DE1493277B (de)		Verfahren zur Entalkylierung alkylaromatischer Kohlenwasserstoffe
DE69918337T2 (de)	2005-06-30	Verfahren zur herstellung von 2,6-dialkylnaphthalen
DE2139043A1 (de)	1972-02-10	Kontinuierliches Verfahren zur Be handlung eines Kohlenwasserstoffstromes aus einem Gemisch alkylaromatischer Kohlen Wasserstoffe
AT305978B (de)	1973-03-26	Verfahren zur Isomerisierung von einer C8-Aromatenfraktion
SU992502A1 (ru)	1983-01-30	Способ получени бензола
DE960631C (de)	1957-03-28	Verfahren zur Herstellung von Polymethylbenzolen durch katalytische Methylierung von Benzol und Toluol
DE924382C (de)	1955-03-03	Herstellung aromatischer Kohlenwasserstoffe