CS195664B2 - Process for the regeneration of isoprene from mixture containing isoprene and cyclopentadiene - Google Patents
Process for the regeneration of isoprene from mixture containing isoprene and cyclopentadiene Download PDFInfo
- Publication number
- CS195664B2 CS195664B2 CS719078A CS907871A CS195664B2 CS 195664 B2 CS195664 B2 CS 195664B2 CS 719078 A CS719078 A CS 719078A CS 907871 A CS907871 A CS 907871A CS 195664 B2 CS195664 B2 CS 195664B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- mol
- column
- isoprene
- extractive distillation
- stream
- Prior art date
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims abstract description 120
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 230000008929 regeneration Effects 0.000 title description 5
- 238000011069 regeneration method Methods 0.000 title description 5
- 239000002904 solvent Substances 0.000 claims abstract description 45
- 238000000895 extractive distillation Methods 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 238000004821 distillation Methods 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
- -1 dimethylocetamide Chemical compound 0.000 claims abstract description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims description 9
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 230000000670 limiting effect Effects 0.000 claims description 2
- 238000005215 recombination Methods 0.000 claims description 2
- 230000006798 recombination Effects 0.000 claims description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims 2
- 244000144992 flock Species 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 abstract description 5
- 238000011084 recovery Methods 0.000 abstract description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 abstract description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000539 dimer Substances 0.000 abstract description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract description 4
- 239000011877 solvent mixture Substances 0.000 abstract 8
- 238000007599 discharging Methods 0.000 abstract 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- NMPUXBGMZJSNLB-UHFFFAOYSA-N cyclopenta-1,3-diene;2-methylbuta-1,3-diene Chemical compound CC(=C)C=C.C1C=CC=C1 NMPUXBGMZJSNLB-UHFFFAOYSA-N 0.000 abstract 1
- 230000000447 dimerizing effect Effects 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 238000002317 scanning near-field acoustic microscopy Methods 0.000 abstract 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 6
- 238000006471 dimerization reaction Methods 0.000 description 5
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical group CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- NPEFCBOZLJONQL-UHFFFAOYSA-N cyclopentane;2-methylbuta-1,3-diene Chemical compound CC(=C)C=C.C1CCCC1 NPEFCBOZLJONQL-UHFFFAOYSA-N 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Natural products O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004711 α-olefin 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3361370 | 1970-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195664B2 true CS195664B2 (en) | 1980-02-29 |
Family
ID=11237947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS719078A CS195664B2 (en) | 1970-12-29 | 1971-12-29 | Process for the regeneration of isoprene from mixture containing isoprene and cyclopentadiene |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3860496A (ro) |
| JP (1) | JPS5328403B1 (ro) |
| AT (1) | AT319192B (ro) |
| AU (1) | AU468106B2 (ro) |
| BE (1) | BE777186A (ro) |
| BG (1) | BG22800A3 (ro) |
| BR (1) | BR7108716D0 (ro) |
| CA (1) | CA957321A (ro) |
| CS (1) | CS195664B2 (ro) |
| DK (1) | DK130919B (ro) |
| ES (1) | ES398777A1 (ro) |
| FR (1) | FR2124658A5 (ro) |
| GB (1) | GB1340149A (ro) |
| HU (1) | HU167163B (ro) |
| LU (1) | LU64525A1 (ro) |
| NL (1) | NL171150C (ro) |
| PL (1) | PL82897B1 (ro) |
| RO (1) | RO61668A (ro) |
| SU (1) | SU473353A3 (ro) |
| YU (1) | YU34872B (ro) |
| ZA (1) | ZA718692B (ro) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081332A (en) * | 1976-08-27 | 1978-03-28 | The B. F. Goodrich Company | Extractive distillation of C5 hydrocarbons using acetonitrile and additives |
| JPS6021125B2 (ja) * | 1976-12-20 | 1985-05-25 | ジェイエスアール株式会社 | イソプレンの精製法 |
| US4134795A (en) * | 1978-04-05 | 1979-01-16 | The Goodyear Tire & Rubber Company | Acetylenes removal from diolefin streams by extractive distillation |
| DE2911395C2 (de) * | 1979-03-23 | 1985-03-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung eines konjugierten Diolefins aus einem C↓4↓- oder C↓5↓-Kohlenwasserstoffgemisch |
| EP0130244A1 (en) * | 1983-06-29 | 1985-01-09 | The C.W. Nofsinger Company | Extractive distillation process for the purification of diolefins |
| DE3338269A1 (de) * | 1983-10-21 | 1985-05-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von isopren aus einem c(pfeil abwaerts)5(pfeil abwaerts)-kohlenwasserstoffgemisch |
| US4629533A (en) * | 1985-01-31 | 1986-12-16 | Phillips Petroleum Company | Isolation of 3-methyl-1-butene from a hydrocarbon stream |
| US4955468A (en) * | 1989-09-08 | 1990-09-11 | Phillips Petroleum Company | Separation of hydrocarbon mixtures |
| US4954224A (en) * | 1989-09-08 | 1990-09-04 | Brown Ronald E | Extractive distillation of hydrocarbon feeds employing mixed solvent |
| US5154802A (en) * | 1991-07-17 | 1992-10-13 | Phillips Petroleum Company | Separation of unsaturated hydrocarbons by extractive distillation |
| CN101516830B (zh) * | 2006-09-28 | 2013-11-27 | 巴斯夫欧洲公司 | 通过蒸馏连续分离含有吗啉（mo）、单氨基二甘醇（adg）、氨和水的混合物的方法 |
| ATE459607T1 (de) * | 2006-09-28 | 2010-03-15 | Basf Se | Verfahren zur kontinuierlichen destillativen auftrennung von gemischen enthaltend morpholin (mo), monoaminodiglykol (adg), ammoniak und wasser |
| CN101522650B (zh) * | 2006-09-28 | 2012-02-08 | 巴斯夫欧洲公司 | 通过蒸馏连续分离含有吗啉（mo）、单氨基二甘醇（adg）、氨和水的混合物的方法 |
| CN101337132B (zh) * | 2008-08-04 | 2013-08-21 | 董保军 | 萃取精馏工艺 |
| AR101431A1 (es) * | 2013-06-05 | 2016-12-21 | Gtc Technology Us Llc | Proceso y aparatos para separar di-olefinas c₅ de naftas de pirólisis |
| WO2015026649A1 (en) | 2013-08-22 | 2015-02-26 | General Electric Company | Use of polyamines as a cs2 scavenger in isoprene production |
| WO2016097999A1 (en) | 2014-12-18 | 2016-06-23 | Sabic Global Technologies B.V. | Isoprene extraction with preserved c5 feedstock |
| CN111320520B (zh) * | 2018-12-14 | 2024-01-23 | 中国石油化工股份有限公司 | 一种用于丁二烯分离的萃取精馏塔和分离方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426705A (en) * | 1942-12-29 | 1947-09-02 | Standard Oil Dev Co | Recovery of isoprene by fractionation and extractive distillation |
| US2461346A (en) * | 1944-12-28 | 1949-02-08 | Standard Oil Dev Co | Separation of hydrocarbons |
| US3012947A (en) * | 1959-06-15 | 1961-12-12 | Exxon Research Engineering Co | Recovery of high purity isoprene from light steam cracked distillate |
| US3038016A (en) * | 1959-08-17 | 1962-06-05 | Phillips Petroleum Co | Isoprene separation |
| BE672305A (ro) * | 1962-05-18 | |||
| SE353078B (ro) * | 1965-12-30 | 1973-01-22 | Japanese Geon Co Ltd | |
| US3510405A (en) * | 1967-11-11 | 1970-05-05 | Nippon Zeon Co | Isoprene purification process |
| US3634537A (en) * | 1969-05-14 | 1972-01-11 | Phillips Petroleum Co | Solvent extraction process |
| BE754702A (fr) * | 1969-08-13 | 1971-01-18 | Metallgesellschaft Ag | Procede de dissociation de melanges d'hydrocarbures, et produits obtenus |
-
1971
- 1971-12-13 AU AU36794/71A patent/AU468106B2/en not_active Expired
- 1971-12-23 GB GB6008971A patent/GB1340149A/en not_active Expired
- 1971-12-23 BE BE777186A patent/BE777186A/xx not_active IP Right Cessation
- 1971-12-24 FR FR7146538A patent/FR2124658A5/fr not_active Expired
- 1971-12-24 CA CA131,174A patent/CA957321A/en not_active Expired
- 1971-12-25 RO RO69193A patent/RO61668A/ro unknown
- 1971-12-27 ES ES398777A patent/ES398777A1/es not_active Expired
- 1971-12-27 YU YU3273/71A patent/YU34872B/xx unknown
- 1971-12-28 SU SU1728983A patent/SU473353A3/ru active
- 1971-12-28 HU HUSA2296A patent/HU167163B/hu unknown
- 1971-12-28 PL PL1971152528A patent/PL82897B1/pl unknown
- 1971-12-28 DK DK639671AA patent/DK130919B/da not_active IP Right Cessation
- 1971-12-28 BG BG019358A patent/BG22800A3/xx unknown
- 1971-12-28 LU LU64525D patent/LU64525A1/xx unknown
- 1971-12-29 ZA ZA718692A patent/ZA718692B/xx unknown
- 1971-12-29 NL NLAANVRAGE7118073,A patent/NL171150C/xx not_active IP Right Cessation
- 1971-12-29 CS CS719078A patent/CS195664B2/cs unknown
- 1971-12-29 US US213544A patent/US3860496A/en not_active Expired - Lifetime
- 1971-12-29 JP JP723717A patent/JPS5328403B1/ja active Pending
- 1971-12-29 AT AT1123971A patent/AT319192B/de not_active IP Right Cessation
- 1971-12-31 BR BR8716/71A patent/BR7108716D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU468106B2 (en) | 1976-01-08 |
| BR7108716D0 (pt) | 1973-03-08 |
| NL171150B (nl) | 1982-09-16 |
| BG22800A3 (bg) | 1977-04-20 |
| NL7118073A (ro) | 1972-07-03 |
| SU473353A3 (ru) | 1975-06-05 |
| DK130919C (ro) | 1975-10-06 |
| DE2165454B2 (de) | 1977-06-30 |
| JPS5328403B1 (ro) | 1978-08-15 |
| US3860496A (en) | 1975-01-14 |
| RO61668A (ro) | 1977-02-15 |
| HU167163B (ro) | 1975-08-28 |
| CA957321A (en) | 1974-11-05 |
| GB1340149A (en) | 1973-12-12 |
| DK130919B (da) | 1975-05-05 |
| ZA718692B (en) | 1972-09-27 |
| AU3679471A (en) | 1973-06-14 |
| PL82897B1 (ro) | 1975-10-31 |
| FR2124658A5 (ro) | 1972-09-22 |
| BE777186A (fr) | 1972-04-17 |
| DE2165454A1 (de) | 1972-07-06 |
| AT319192B (de) | 1974-12-10 |
| ES398777A1 (es) | 1975-06-01 |
| YU34872B (en) | 1980-04-30 |
| YU327371A (en) | 1979-10-31 |
| NL171150C (nl) | 1983-02-16 |
| LU64525A1 (ro) | 1972-06-20 |
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