DE1468566C3 - Verfahren zur Isolierung von aromatischen Kohlenwasserstoffen aus Gemischen, die Alkene und stärker ungesättigte Verbindungen enthalten - Google Patents
Verfahren zur Isolierung von aromatischen Kohlenwasserstoffen aus Gemischen, die Alkene und stärker ungesättigte Verbindungen enthaltenInfo
- Publication number
- DE1468566C3 DE1468566C3 DE1468566A DES0078569A DE1468566C3 DE 1468566 C3 DE1468566 C3 DE 1468566C3 DE 1468566 A DE1468566 A DE 1468566A DE S0078569 A DES0078569 A DE S0078569A DE 1468566 C3 DE1468566 C3 DE 1468566C3
- Authority
- DE
- Germany
- Prior art keywords
- column
- extraction
- unsaturated compounds
- alkenes
- percent
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 46
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 150000001336 alkenes Chemical class 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 20
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 18
- 238000002955 isolation Methods 0.000 title claims description 7
- 239000002904 solvent Substances 0.000 claims description 46
- 229930195733 hydrocarbon Natural products 0.000 claims description 25
- 150000002430 hydrocarbons Chemical class 0.000 claims description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000007791 liquid phase Substances 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 102
- 238000000605 extraction Methods 0.000 description 50
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 45
- 239000007858 starting material Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 30
- 238000009835 boiling Methods 0.000 description 25
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 22
- 239000012071 phase Substances 0.000 description 21
- 238000004821 distillation Methods 0.000 description 20
- 239000000284 extract Substances 0.000 description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 12
- 150000001491 aromatic compounds Chemical class 0.000 description 11
- 239000000539 dimer Substances 0.000 description 11
- 239000003502 gasoline Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- 150000001993 dienes Chemical class 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- 150000001925 cycloalkenes Chemical class 0.000 description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- -1 Alkylene glycols Chemical class 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004992 fission Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004227 thermal cracking Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- KBLZUSCEBGBILB-UHFFFAOYSA-N 2,2-dimethylthiolane 1,1-dioxide Chemical compound CC1(C)CCCS1(=O)=O KBLZUSCEBGBILB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen
- C10G67/0409—Extraction of unsaturated hydrocarbons
- C10G67/0427—The hydrotreatment being a selective hydrogenation of diolefins or acetylenes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL262671 | 1961-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1468566A1 DE1468566A1 (de) | 1968-12-05 |
| DE1468566C3 true DE1468566C3 (de) | 1979-11-29 |
Family
ID=19752936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1468566A Expired DE1468566C3 (de) | 1961-03-22 | 1962-03-20 | Verfahren zur Isolierung von aromatischen Kohlenwasserstoffen aus Gemischen, die Alkene und stärker ungesättigte Verbindungen enthalten |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3316318A (enrdf_load_stackoverflow) |
| BE (1) | BE615315A (enrdf_load_stackoverflow) |
| DE (1) | DE1468566C3 (enrdf_load_stackoverflow) |
| DK (1) | DK105331C (enrdf_load_stackoverflow) |
| GB (1) | GB954439A (enrdf_load_stackoverflow) |
| NL (2) | NL113747C (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE438615B (sv) * | 1976-04-28 | 1985-04-29 | Thermal Dynamics Corp | Bagsvetsapparat |
| FR2553760B1 (fr) * | 1983-10-25 | 1986-05-02 | Inst Francais Du Petrole | Procede d'hydrogenation selective en presence de solvant des composes acetyleniques d'une coupe d'hydrocarbures c4 riche en butadiene |
| DE19603901A1 (de) * | 1996-02-03 | 1997-08-07 | Krupp Uhde Gmbh | Verfahren zur Gewinnung von Reinaromaten aus Reformatbenzin und Vorrichtung zur Durchführung des Verfahrens |
| KR102464480B1 (ko) * | 2020-06-16 | 2022-11-07 | 주식회사 엘지화학 | 방향족 탄화수소의 제조방법 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694671A (en) * | 1950-09-01 | 1954-11-16 | Standard Oil Dev Co | Selective hydrogenation process |
| US2799627A (en) * | 1953-08-17 | 1957-07-16 | Universal Oil Prod Co | Process for obtaining concentrated aromatic hydrocarbons |
| US2717861A (en) * | 1954-08-11 | 1955-09-13 | Exxon Research Engineering Co | Selective hydrogenation process |
| US2870226A (en) * | 1956-03-19 | 1959-01-20 | Universal Oil Prod Co | Production and recovery of aromatic hydrocarbons |
| US2952717A (en) * | 1957-04-18 | 1960-09-13 | Union Oil Co | Separation of hydrocarbons by dual solvent extraction |
| BE588708A (enrdf_load_stackoverflow) * | 1959-03-18 |
-
0
- BE BE615315D patent/BE615315A/xx unknown
- NL NL262671D patent/NL262671A/xx unknown
- NL NL113747D patent/NL113747C/xx active
-
1962
- 1962-03-09 US US178615A patent/US3316318A/en not_active Expired - Lifetime
- 1962-03-20 DE DE1468566A patent/DE1468566C3/de not_active Expired
- 1962-03-20 GB GB10638/62A patent/GB954439A/en not_active Expired
- 1962-03-21 DK DK129662AA patent/DK105331C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| US3316318A (en) | 1967-04-25 |
| GB954439A (en) | 1964-04-08 |
| NL113747C (enrdf_load_stackoverflow) | |
| NL262671A (enrdf_load_stackoverflow) | |
| DE1468566A1 (de) | 1968-12-05 |
| DK105331C (da) | 1966-09-19 |
| BE615315A (enrdf_load_stackoverflow) |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |