DE2263601A1 - Verfahren zum abtrennen von cyclopentadien, cyclopenten und/oder pentadien-1,3 - Google Patents
Verfahren zum abtrennen von cyclopentadien, cyclopenten und/oder pentadien-1,3Info
- Publication number
- DE2263601A1 DE2263601A1 DE19722263601 DE2263601A DE2263601A1 DE 2263601 A1 DE2263601 A1 DE 2263601A1 DE 19722263601 DE19722263601 DE 19722263601 DE 2263601 A DE2263601 A DE 2263601A DE 2263601 A1 DE2263601 A1 DE 2263601A1
- Authority
- DE
- Germany
- Prior art keywords
- fraction
- cyclopentadiene
- pentane
- pentadiene
- cyclopentene
- 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.)
- Pending
Links
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims description 372
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title claims description 222
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims description 121
- 238000000034 method Methods 0.000 title claims description 59
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 223
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 119
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 115
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 72
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 69
- 238000000895 extractive distillation Methods 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 61
- 238000004821 distillation Methods 0.000 claims description 57
- 239000002904 solvent Substances 0.000 claims description 55
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 42
- 238000009835 boiling Methods 0.000 claims description 32
- 238000010533 azeotropic distillation Methods 0.000 claims description 29
- 238000000605 extraction Methods 0.000 claims description 29
- 238000010438 heat treatment Methods 0.000 claims description 23
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 14
- 239000002798 polar solvent Substances 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000036961 partial effect Effects 0.000 claims description 4
- -1 1,3-pentadiene hydrocarbon Chemical class 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- 238000005336 cracking Methods 0.000 claims description 2
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- GPPPLWNBCOTBLB-UHFFFAOYSA-N C1CC=CC1.C1C=CC=C1 Chemical compound C1CC=CC1.C1C=CC=C1 GPPPLWNBCOTBLB-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 210000003918 fraction a Anatomy 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 27
- 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 description 25
- 238000010992 reflux Methods 0.000 description 22
- 238000003795 desorption Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 14
- 150000001993 dienes Chemical class 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006471 dimerization reaction Methods 0.000 description 7
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical group CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000727 fraction Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000004227 thermal cracking Methods 0.000 description 2
- GIJIKFKGLZGENN-UHFFFAOYSA-N (4-ethoxyphenyl) 4-butoxycarbonyloxybenzoate Chemical compound C1=CC(OC(=O)OCCCC)=CC=C1C(=O)OC1=CC=C(OCC)C=C1 GIJIKFKGLZGENN-UHFFFAOYSA-N 0.000 description 1
- XAJOPMVSQIBJCW-SNAWJCMRSA-N (E)-3-penten-1-yne Chemical group C\C=C\C#C XAJOPMVSQIBJCW-SNAWJCMRSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- OPCMVVKRCLOEDQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(methylamino)pentan-1-one Chemical compound ClC1=CC=C(C=C1)C(C(CCC)NC)=O OPCMVVKRCLOEDQ-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- NZZMNINUUFWWNR-UHFFFAOYSA-N CCCCC.CCC(C)C Chemical compound CCCCC.CCC(C)C NZZMNINUUFWWNR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
- C07C13/61—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system with a bridged indene ring, e.g. dicyclopentadiene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- 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
- C07C7/06—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by azeotropic 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP130172A JPS5529967B2 (enExample) | 1971-12-27 | 1971-12-27 | |
| JP645172A JPS5529968B2 (enExample) | 1972-01-14 | 1972-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2263601A1 true DE2263601A1 (de) | 1973-07-12 |
Family
ID=26334498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722263601 Pending DE2263601A1 (de) | 1971-12-27 | 1972-12-27 | Verfahren zum abtrennen von cyclopentadien, cyclopenten und/oder pentadien-1,3 |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE2263601A1 (enExample) |
| FR (1) | FR2166100A1 (enExample) |
| GB (1) | GB1404970A (enExample) |
| IT (1) | IT976168B (enExample) |
| NL (1) | NL7217692A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103086822B (zh) * | 2011-11-02 | 2016-03-30 | 中国石油化工股份有限公司 | 一种间戊二烯的分离方法 |
| CN103570576B (zh) * | 2012-07-20 | 2016-06-15 | 中国石油化工集团公司 | 一种裂解碳五分离装置循环溶剂再生系统及方法 |
| WO2021048657A1 (en) * | 2019-09-11 | 2021-03-18 | Sabic Global Technologies B.V. | Recovery of isoprene and cpd from a pygas stream |
| CN114436741B (zh) * | 2020-10-16 | 2024-04-19 | 中国石油化工股份有限公司 | 一种环戊烯的制备方法 |
-
1972
- 1972-12-22 GB GB5952872A patent/GB1404970A/en not_active Expired
- 1972-12-27 FR FR7246490A patent/FR2166100A1/fr not_active Withdrawn
- 1972-12-27 DE DE19722263601 patent/DE2263601A1/de active Pending
- 1972-12-27 IT IT7109772A patent/IT976168B/it active
- 1972-12-27 NL NL7217692A patent/NL7217692A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT976168B (it) | 1974-08-20 |
| FR2166100A1 (enExample) | 1973-08-10 |
| GB1404970A (en) | 1975-09-03 |
| NL7217692A (enExample) | 1973-06-29 |
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