CS195663B2 - Způsob oddělování butadienu nebo isoprenu za směsí uhlovodíků - Google Patents
Způsob oddělování butadienu nebo isoprenu za směsí uhlovodíků Download PDFInfo
- Publication number
- CS195663B2 CS195663B2 CS719077A CS907771A CS195663B2 CS 195663 B2 CS195663 B2 CS 195663B2 CS 719077 A CS719077 A CS 719077A CS 907771 A CS907771 A CS 907771A CS 195663 B2 CS195663 B2 CS 195663B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- isoprene
- solvent
- butadiene
- mol
- column
- Prior art date
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 56
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 42
- 229930195733 hydrocarbon Natural products 0.000 title claims description 27
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 11
- 238000000926 separation method Methods 0.000 title claims description 7
- 239000002904 solvent Substances 0.000 claims description 36
- 238000000895 extractive distillation Methods 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000011877 solvent mixture Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical group O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- CADBWPMBEYCJFU-UHFFFAOYSA-N morpholine-2-carbaldehyde Chemical compound O=CC1CNCCO1 CADBWPMBEYCJFU-UHFFFAOYSA-N 0.000 claims description 2
- VVHBCUUKJUWRBA-UHFFFAOYSA-N morpholine-3-carbaldehyde Chemical compound O=CC1COCCN1 VVHBCUUKJUWRBA-UHFFFAOYSA-N 0.000 claims description 2
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
- FWCHISPFSGCORQ-UHFFFAOYSA-N morpholine;hydrate Chemical compound O.C1COCCN1 FWCHISPFSGCORQ-UHFFFAOYSA-N 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 229920006395 saturated elastomer Chemical class 0.000 description 5
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- -1 oleic hydrocarbons Chemical class 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 4
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 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
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-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
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- NLYFPBIGYPICIA-UHFFFAOYSA-N O.C(=O)N1CCOCC1.N1CCOCC1 Chemical compound O.C(=O)N1CCOCC1.N1CCOCC1 NLYFPBIGYPICIA-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 1
- 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 1
- ARXRUGFLKOSYIJ-UHFFFAOYSA-N 2-methylbuta-1,3-diene 2-methylbut-2-ene Chemical compound CC=C(C)C.CC(=C)C=C ARXRUGFLKOSYIJ-UHFFFAOYSA-N 0.000 description 1
- IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 description 1
- ZGFGZHNVGRKIJQ-UHFFFAOYSA-N 3-morpholin-4-ylmorpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1N1CCOCC1 ZGFGZHNVGRKIJQ-UHFFFAOYSA-N 0.000 description 1
- HQFWVSGBVLEQGA-UHFFFAOYSA-N 4-aminobenzoic acid 3-(dibutylamino)propyl ester Chemical compound CCCCN(CCCC)CCCOC(=O)C1=CC=C(N)C=C1 HQFWVSGBVLEQGA-UHFFFAOYSA-N 0.000 description 1
- IHGQJEAXQYAQRT-UHFFFAOYSA-N CC#C.CC=C=C Chemical compound CC#C.CC=C=C IHGQJEAXQYAQRT-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
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- 229960003369 butacaine Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- SJAILLWIJJSQQH-UHFFFAOYSA-N morpholine morpholine-4-carbaldehyde Chemical compound C(=O)N1CCOCC1.N1CCOCC1 SJAILLWIJJSQQH-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3361470 | 1970-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195663B2 true CS195663B2 (cs) | 1980-02-29 |
Family
ID=11237956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS719077A CS195663B2 (cs) | 1970-12-29 | 1971-12-29 | Způsob oddělování butadienu nebo isoprenu za směsí uhlovodíků |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3784626A (en, 2012) |
| JP (1) | JPS5233085B1 (en, 2012) |
| AR (1) | AR205147Q (en, 2012) |
| AT (1) | AT323119B (en, 2012) |
| AU (1) | AU476017B2 (en, 2012) |
| BE (1) | BE777248A (en, 2012) |
| BG (1) | BG25067A3 (en, 2012) |
| CA (1) | CA976990A (en, 2012) |
| CS (1) | CS195663B2 (en, 2012) |
| DE (1) | DE2165453A1 (en, 2012) |
| EG (1) | EG10990A (en, 2012) |
| ES (1) | ES398783A1 (en, 2012) |
| FR (1) | FR2120862A5 (en, 2012) |
| HU (1) | HU165735B (en, 2012) |
| LU (1) | LU64527A1 (en, 2012) |
| NL (1) | NL171044C (en, 2012) |
| PL (1) | PL77160B1 (en, 2012) |
| RO (1) | RO61667A (en, 2012) |
| SU (1) | SU466650A3 (en, 2012) |
| ZA (1) | ZA718643B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140587A (en) * | 1969-07-18 | 1979-02-20 | Snamprogetti, S.P.A. | Process for the separation of diolefins from mixtures containing the same |
| US3953300A (en) * | 1972-11-29 | 1976-04-27 | Snam Progetti, S.P.A. | Process for separating a high purity vinyl aromatic hydrocarbon from hydrocarbon mixtures containing the same |
| IT994985B (it) * | 1973-07-20 | 1975-10-20 | Snam Progetti | Solvente per la separazione di diolefine da miscele che li contengono |
| IT1012685B (it) * | 1974-05-21 | 1977-03-10 | Snam Progetti | Processo per la separazione di buta diene da correnti idrocarburiche o 4 ottenute per steam cracking |
| 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 |
| 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 |
| DE2911393C2 (de) * | 1979-03-23 | 1984-07-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung eines konjugierten Diolefins aus einem C↓4↓-oder C↓5↓-Kohlenwasserstoffgemisch |
| US10836691B2 (en) * | 2015-09-22 | 2020-11-17 | Fina Technology, Inc. | Upgrading a C5 olefin stream |
-
1971
- 1971-12-21 HU HUSA2292A patent/HU165735B/hu unknown
- 1971-12-23 CA CA131,072A patent/CA976990A/en not_active Expired
- 1971-12-23 EG EG550/71A patent/EG10990A/xx active
- 1971-12-24 FR FR7146539A patent/FR2120862A5/fr not_active Expired
- 1971-12-24 AU AU37335/71A patent/AU476017B2/en not_active Expired
- 1971-12-24 BE BE777248A patent/BE777248A/xx not_active IP Right Cessation
- 1971-12-25 RO RO69192A patent/RO61667A/ro unknown
- 1971-12-28 SU SU1729140A patent/SU466650A3/ru active
- 1971-12-28 ES ES398783A patent/ES398783A1/es not_active Expired
- 1971-12-28 LU LU64527D patent/LU64527A1/xx unknown
- 1971-12-28 PL PL1971152529A patent/PL77160B1/pl unknown
- 1971-12-28 ZA ZA718643A patent/ZA718643B/xx unknown
- 1971-12-29 DE DE19712165453 patent/DE2165453A1/de active Pending
- 1971-12-29 NL NLAANVRAGE7118036,A patent/NL171044C/xx not_active IP Right Cessation
- 1971-12-29 CS CS719077A patent/CS195663B2/cs unknown
- 1971-12-29 JP JP47003718A patent/JPS5233085B1/ja active Pending
- 1971-12-29 BG BG019370A patent/BG25067A3/xx unknown
- 1971-12-29 AT AT1124071A patent/AT323119B/de not_active IP Right Cessation
- 1971-12-29 US US00213485A patent/US3784626A/en not_active Expired - Lifetime
-
1972
- 1972-01-01 AR AR240357A patent/AR205147Q/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5233085B1 (en, 2012) | 1977-08-26 |
| AT323119B (de) | 1975-06-25 |
| DE2165453A1 (de) | 1972-07-20 |
| AU3733571A (en) | 1973-06-28 |
| EG10990A (en) | 1976-11-30 |
| ES398783A1 (es) | 1975-05-16 |
| LU64527A1 (en, 2012) | 1972-06-20 |
| AR205147Q (es) | 1976-04-12 |
| BG25067A3 (en) | 1978-07-12 |
| BE777248A (fr) | 1972-04-17 |
| SU466650A3 (ru) | 1975-04-05 |
| NL7118036A (en, 2012) | 1972-07-03 |
| AU476017B2 (en) | 1976-09-09 |
| ZA718643B (en) | 1972-11-29 |
| US3784626A (en) | 1974-01-08 |
| CA976990A (en) | 1975-10-28 |
| FR2120862A5 (en, 2012) | 1972-08-18 |
| HU165735B (en, 2012) | 1974-10-28 |
| RO61667A (en, 2012) | 1977-01-15 |
| NL171044C (nl) | 1983-02-01 |
| NL171044B (nl) | 1982-09-01 |
| PL77160B1 (en, 2012) | 1975-04-30 |
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