DE2364891A1 - Verfahren zur herstellung von aethylcyclohexan - Google Patents
Verfahren zur herstellung von aethylcyclohexanInfo
- Publication number
- DE2364891A1 DE2364891A1 DE2364891A DE2364891A DE2364891A1 DE 2364891 A1 DE2364891 A1 DE 2364891A1 DE 2364891 A DE2364891 A DE 2364891A DE 2364891 A DE2364891 A DE 2364891A DE 2364891 A1 DE2364891 A1 DE 2364891A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenated
- mixture
- ethylbenzene
- xylene
- stage
- Prior art date
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title description 10
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 110
- 239000000203 mixture Substances 0.000 claims description 97
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 92
- 238000005984 hydrogenation reaction Methods 0.000 claims description 70
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 44
- 239000008096 xylene Substances 0.000 claims description 36
- 150000003738 xylenes Chemical class 0.000 claims description 35
- 238000004821 distillation Methods 0.000 claims description 23
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 19
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 13
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 11
- 229940078552 o-xylene Drugs 0.000 claims description 9
- 150000005194 ethylbenzenes Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- SGVUHPSBDNVHKL-UHFFFAOYSA-N 1,3-dimethylcyclohexane Chemical compound CC1CCCC(C)C1 SGVUHPSBDNVHKL-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KVZJLSYJROEPSQ-UHFFFAOYSA-N 1,2-dimethylcyclohexane Chemical compound CC1CCCCC1C KVZJLSYJROEPSQ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- -1 naphthene hydrocarbons Chemical class 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 235000015243 ice cream Nutrition 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001833 catalytic reforming Methods 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007700 distillative separation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 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
- 238000001179 sorption measurement Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- GEAHSFIOZABQIK-UHFFFAOYSA-N 1,2-xylene;1,3-xylene Chemical group CC1=CC=CC(C)=C1.CC1=CC=CC=C1C GEAHSFIOZABQIK-UHFFFAOYSA-N 0.000 description 1
- ADFVYWCDAKWKPH-UHFFFAOYSA-N 4-ethoxycarbonylbenzoic acid Chemical compound CCOC(=O)C1=CC=C(C(O)=O)C=C1 ADFVYWCDAKWKPH-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HXGNONMTCROKON-UHFFFAOYSA-N [Pt].[Si]=O Chemical compound [Pt].[Si]=O HXGNONMTCROKON-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- HBGFKRXFJPVYFB-UHFFFAOYSA-N ethylbenzene;1,4-xylene Chemical group CCC1=CC=CC=C1.CC1=CC=C(C)C=C1 HBGFKRXFJPVYFB-UHFFFAOYSA-N 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
Classifications
-
- 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
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT33784/72A IT974760B (it) | 1972-12-29 | 1972-12-29 | Procedimento di preparazione di etilcioloesano |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2364891A1 true DE2364891A1 (de) | 1974-07-04 |
Family
ID=11238111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2364891A Withdrawn DE2364891A1 (de) | 1972-12-29 | 1973-12-28 | Verfahren zur herstellung von aethylcyclohexan |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006038631A1 (de) * | 2006-08-17 | 2008-02-21 | Miltitz Aromatics Gmbh | Verfahren und Vorrichtung zur Herstellung von Ethylcyclohexan durch katalytische Hydrierung in der Flüssigphase |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2282231A (en) * | 1941-04-19 | 1942-05-05 | Universal Oil Prod Co | Separation of aromatic hydrocarbons |
| US3113978A (en) * | 1955-09-13 | 1963-12-10 | Gulf Research Development Co | Production of para-xylene |
| NL260446A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-01-25 | 1900-01-01 | ||
| US3341613A (en) * | 1964-10-30 | 1967-09-12 | Phillips Petroleum Co | Method for production of cyclohexane by the hydrogenation of benzene |
| US3384676A (en) * | 1965-01-15 | 1968-05-21 | Universal Oil Prod Co | Hydrogenation of para and meta xylene mixtrues |
| US3458589A (en) * | 1967-12-04 | 1969-07-29 | Universal Oil Prod Co | Conversion and separation of isomeric xylenes |
| US3715408A (en) * | 1970-01-30 | 1973-02-06 | Cosden Oil & Chem Co | Separation of diethylbenzene isomers by distillation and dehydrogenation |
-
1972
- 1972-12-29 IT IT33784/72A patent/IT974760B/it active
-
1973
- 1973-12-21 BE BE139138A patent/BE808952A/xx unknown
- 1973-12-27 US US428768A patent/US3890401A/en not_active Expired - Lifetime
- 1973-12-27 FR FR7346647A patent/FR2212312B1/fr not_active Expired
- 1973-12-27 CA CA188,956A patent/CA1010460A/en not_active Expired
- 1973-12-28 DE DE2364891A patent/DE2364891A1/de not_active Withdrawn
- 1973-12-28 NL NL7317781A patent/NL7317781A/xx not_active Application Discontinuation
- 1973-12-29 JP JP49004922A patent/JPS4994647A/ja active Pending
- 1973-12-31 GB GB6019573A patent/GB1425665A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006038631A1 (de) * | 2006-08-17 | 2008-02-21 | Miltitz Aromatics Gmbh | Verfahren und Vorrichtung zur Herstellung von Ethylcyclohexan durch katalytische Hydrierung in der Flüssigphase |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2212312A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-26 |
| NL7317781A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-02 |
| US3890401A (en) | 1975-06-17 |
| GB1425665A (en) | 1976-02-18 |
| JPS4994647A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-09 |
| BE808952A (fr) | 1974-06-21 |
| CA1010460A (en) | 1977-05-17 |
| FR2212312B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-08 |
| IT974760B (it) | 1974-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |