CA1217449A - Recovery of a conjugated diolefin and/or an olefin from a c.sub.4- or c.sub.5-hydrocarbon mixture - Google Patents
Recovery of a conjugated diolefin and/or an olefin from a c.sub.4- or c.sub.5-hydrocarbon mixtureInfo
- Publication number
- CA1217449A CA1217449A CA000466304A CA466304A CA1217449A CA 1217449 A CA1217449 A CA 1217449A CA 000466304 A CA000466304 A CA 000466304A CA 466304 A CA466304 A CA 466304A CA 1217449 A CA1217449 A CA 1217449A
- Authority
- CA
- Canada
- Prior art keywords
- zone
- separation zone
- separation
- olefin
- hydrocarbons
- 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 abstract description 76
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 60
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 39
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 150000001993 dienes Chemical class 0.000 title claims abstract description 28
- 238000011084 recovery Methods 0.000 title claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 72
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 72
- 239000002904 solvent Substances 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 38
- 230000008569 process Effects 0.000 claims abstract description 33
- 238000000895 extractive distillation Methods 0.000 claims abstract description 17
- 238000000926 separation method Methods 0.000 claims description 118
- 239000000047 product Substances 0.000 claims description 47
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 40
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 17
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000007700 distillative separation Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 3
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- -1 ali-phatic acid amides Chemical class 0.000 description 7
- 239000000306 component Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000013844 butane Nutrition 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000518994 Conta Species 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000000475 acetylene derivatives Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- SFPQDYSOPQHZAQ-UHFFFAOYSA-N 2-methoxypropanenitrile Chemical compound COC(C)C#N SFPQDYSOPQHZAQ-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000022563 Rema Species 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/141—Fractional distillation or use of a fractionation or rectification column where at least one distillation column contains at least one dividing wall
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833339157 DE3339157A1 (de) | 1983-10-28 | 1983-10-28 | Verfahren zur gewinnung eines konjugierten diolefins und/oder olefins aus einem c(pfeil abwaerts)4(pfeil abwaerts)- oder c(pfeil abwaerts)5(pfeil abwaerts)-kohlenwasserstoffgemisch |
| DEP3339157.2 | 1983-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1217449A true CA1217449A (en) | 1987-02-03 |
Family
ID=6212971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000466304A Expired CA1217449A (en) | 1983-10-28 | 1984-10-25 | Recovery of a conjugated diolefin and/or an olefin from a c.sub.4- or c.sub.5-hydrocarbon mixture |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0141356B1 (en, 2012) |
| JP (1) | JPS60104021A (en, 2012) |
| AT (1) | ATE21685T1 (en, 2012) |
| CA (1) | CA1217449A (en, 2012) |
| DE (2) | DE3339157A1 (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10226718B2 (en) * | 2013-07-29 | 2019-03-12 | Wacker Chemie Ag | Method and device for distillative separation of a three- or multi-component mixture |
| US10300401B2 (en) * | 2014-10-09 | 2019-05-28 | Wacker Chemie Ag | Purification of chlorosilanes by means of distillation and adsorption |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3710434A1 (de) * | 1987-03-28 | 1988-10-06 | Basf Ag | Verfahren zur gewinnung von 1,3-butadien |
| JP4134391B2 (ja) * | 1998-04-07 | 2008-08-20 | 日本ゼオン株式会社 | 不飽和炭化水素の分離精製装置および分離精製方法 |
| DE19818810A1 (de) * | 1998-04-27 | 1999-10-28 | Basf Ag | Verfahren zum Trennen eines C4-Kohlenwasserstoffgemisches |
| WO1999056848A1 (fr) * | 1998-05-06 | 1999-11-11 | Sumitomo Heavy Industries, Ltd. | Dispositif et procede de distillation |
| DE19849651C2 (de) * | 1998-10-29 | 2003-01-16 | Krupp Uhde Gmbh | Rektifizierkolonne für die Extraktivdestillation von eng- oder azeotrop siedenden Gemischen |
| DE10056841A1 (de) * | 2000-11-16 | 2002-05-23 | Basf Ag | Verfahren und Vorrichtung zur destillativen Gewinnung von 1,3-Reinbutadien aus 1,3-Rohbutadien |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE353078B (en, 2012) * | 1965-12-30 | 1973-01-22 | Japanese Geon Co Ltd |
-
1983
- 1983-10-28 DE DE19833339157 patent/DE3339157A1/de not_active Withdrawn
-
1984
- 1984-10-19 AT AT84112672T patent/ATE21685T1/de not_active IP Right Cessation
- 1984-10-19 EP EP84112672A patent/EP0141356B1/de not_active Expired
- 1984-10-19 DE DE8484112672T patent/DE3460567D1/de not_active Expired
- 1984-10-19 JP JP59218749A patent/JPS60104021A/ja active Granted
- 1984-10-25 CA CA000466304A patent/CA1217449A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10226718B2 (en) * | 2013-07-29 | 2019-03-12 | Wacker Chemie Ag | Method and device for distillative separation of a three- or multi-component mixture |
| US10300401B2 (en) * | 2014-10-09 | 2019-05-28 | Wacker Chemie Ag | Purification of chlorosilanes by means of distillation and adsorption |
| US10632398B2 (en) | 2014-10-09 | 2020-04-28 | Wacker Chemie Ag | Purification of chlorosilanes by means of distillation and adsorption |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60104021A (ja) | 1985-06-08 |
| DE3339157A1 (de) | 1985-05-09 |
| DE3460567D1 (en) | 1986-10-02 |
| EP0141356A2 (de) | 1985-05-15 |
| JPH0413330B2 (en, 2012) | 1992-03-09 |
| ATE21685T1 (de) | 1986-09-15 |
| EP0141356B1 (de) | 1986-08-27 |
| EP0141356A3 (en, 2012) | 1985-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |