JPS6251939B2 - - Google Patents
Info
- Publication number
- JPS6251939B2 JPS6251939B2 JP55096325A JP9632580A JPS6251939B2 JP S6251939 B2 JPS6251939 B2 JP S6251939B2 JP 55096325 A JP55096325 A JP 55096325A JP 9632580 A JP9632580 A JP 9632580A JP S6251939 B2 JPS6251939 B2 JP S6251939B2
- Authority
- JP
- Japan
- Prior art keywords
- isoprene
- liquid
- extraction
- fraction
- sulfolane
- 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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 126
- 238000000605 extraction Methods 0.000 claims description 64
- 229930195733 hydrocarbon Natural products 0.000 claims description 58
- 150000002430 hydrocarbons Chemical class 0.000 claims description 53
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 46
- 239000004215 Carbon black (E152) Substances 0.000 claims description 36
- 238000009835 boiling Methods 0.000 claims description 33
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 33
- 238000000638 solvent extraction Methods 0.000 claims description 32
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 15
- 238000004508 fractional distillation Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 238000011084 recovery Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 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 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- -1 isoprene Chemical compound 0.000 claims description 7
- PMJHHCWVYXUKFD-UHFFFAOYSA-N pentadiene group Chemical class C=CC=CC PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 6
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000012530 fluid Substances 0.000 description 61
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 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 8
- 238000004821 distillation Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012465 retentate Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- IIIGXUANQZOIHI-UHFFFAOYSA-N 1,1-dioxothiolan-2-amine Chemical compound NC1CCCS1(=O)=O IIIGXUANQZOIHI-UHFFFAOYSA-N 0.000 description 1
- QDRZGXHVBINHCR-UHFFFAOYSA-N 1,1-dioxothiolan-2-ol Chemical compound OC1CCCS1(=O)=O QDRZGXHVBINHCR-UHFFFAOYSA-N 0.000 description 1
- AWIVDPRAKCJMKA-UHFFFAOYSA-N 2-(1,1-dioxothiolan-2-yl)oxythiolane 1,1-dioxide Chemical class O=S1(=O)CCCC1OC1S(=O)(=O)CCC1 AWIVDPRAKCJMKA-UHFFFAOYSA-N 0.000 description 1
- QAHXBUGLZGGVEM-UHFFFAOYSA-N 2-(1,1-dioxothiolan-2-yl)sulfanylthiolane 1,1-dioxide Chemical compound O=S1(=O)CCCC1SC1S(=O)(=O)CCC1 QAHXBUGLZGGVEM-UHFFFAOYSA-N 0.000 description 1
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical group CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 description 1
- DNCGEOYDGQJILX-UHFFFAOYSA-N 2-nitrothiolane 1,1-dioxide Chemical compound [O-][N+](=O)C1CCCS1(=O)=O DNCGEOYDGQJILX-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002485 inorganic esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7925028 | 1979-07-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5616426A JPS5616426A (en) | 1981-02-17 |
| JPS6251939B2 true JPS6251939B2 (enExample) | 1987-11-02 |
Family
ID=10506576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9632580A Granted JPS5616426A (en) | 1979-07-18 | 1980-07-16 | Recovery of isoprene |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0023370B1 (enExample) |
| JP (1) | JPS5616426A (enExample) |
| CA (1) | CA1146978A (enExample) |
| DE (1) | DE3064122D1 (enExample) |
| ES (1) | ES493414A0 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5865674A (ja) | 1981-10-16 | 1983-04-19 | Ricoh Co Ltd | プリンタ |
| 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 |
| US4935498A (en) * | 1989-03-06 | 1990-06-19 | Board Of Regents, The University Of Texas System | Expanded porphyrins: large porphyrin-like tripyrroledimethine-derived macrocycles |
| KR100458361B1 (ko) * | 2001-09-25 | 2004-11-26 | 한국과학기술연구원 | 추출증류에 의하여 ｃ5 유분에서 이소프렌을 분리하는 방법 |
| US8246815B2 (en) * | 2010-08-10 | 2012-08-21 | Amt International Inc. | Methods for regeneration of solvents for extractive processes |
| EP4534168A1 (en) * | 2023-10-06 | 2025-04-09 | Sulzer Management AG | A process for separating c6-c9-aromatic hydrocarbons and isoprene using an improved extracting agent |
| WO2025073753A1 (en) * | 2023-10-06 | 2025-04-10 | Sulzer Management Ag | A process for separating C6-C9-aromatic hydrocarbons and isoprene using an improved extracting agent |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2360859A (en) * | 1943-02-08 | 1944-10-24 | Shell Dev | Solvent extraction process |
| US3520947A (en) * | 1968-08-19 | 1970-07-21 | Shell Oil Co | Olefin separation |
| FR2036057A5 (enExample) * | 1969-03-03 | 1970-12-24 | Inst Francais Du Petrole | |
| BE794552A (fr) * | 1972-01-28 | 1973-05-16 | Snam Progetti | Procede de separation de l'isoprene des melanges en contenant |
-
1980
- 1980-05-20 CA CA000352244A patent/CA1146978A/en not_active Expired
- 1980-07-04 DE DE8080200652T patent/DE3064122D1/de not_active Expired
- 1980-07-04 EP EP80200652A patent/EP0023370B1/en not_active Expired
- 1980-07-16 JP JP9632580A patent/JPS5616426A/ja active Granted
- 1980-07-16 ES ES493414A patent/ES493414A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5616426A (en) | 1981-02-17 |
| ES8202529A1 (es) | 1981-08-01 |
| ES493414A0 (es) | 1981-08-01 |
| CA1146978A (en) | 1983-05-24 |
| EP0023370B1 (en) | 1983-07-13 |
| EP0023370A1 (en) | 1981-02-04 |
| DE3064122D1 (en) | 1983-08-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3723256A (en) | Aromatic hydrocarbon recovery by extractive distillation, extraction and plural distillations | |
| US3714033A (en) | Process for the separation of aromatic hydrocarbons from a mixed hydrocarbon feedstock | |
| CA1218030A (en) | Recovery of isoprene from a c.sub.5-hydrocarbon mixture | |
| TW201934525A (zh) | 萃取精餾分離芳烴的方法 | |
| KR100203555B1 (ko) | 추출 증류에 의해 부텐과 부탄을 분리하는 방법 | |
| US4311583A (en) | Solvent extraction process | |
| JP5506680B2 (ja) | ベンジン留分および精製流からのベンゼンおよびベンゼン誘導体の回収 | |
| EP0033512B1 (en) | Separation of aromatic hydrocarbons from petroleum fractions | |
| CA1077967A (en) | Benzene production by solvent extraction and hydrodealkylation | |
| JP4243246B2 (ja) | 粗−１，３−ブタジエンの後処理法 | |
| KR20120030382A (ko) | 부타디엔의 분별 추출 | |
| US2395362A (en) | Separation of hydrocarbons | |
| JPS6251939B2 (enExample) | ||
| US3544453A (en) | Process for the extraction and recovery of aromatic hydrocarbons | |
| US3816302A (en) | Process for the recovery of aromatic hydrocarbons from mixtures containing the same | |
| US2766300A (en) | Solvent extraction process | |
| TW201542518A (zh) | 自裂解汽油回收異戊二烯的方法 | |
| US4401560A (en) | Process for the separation of aromatic hydrocarbons from petroleum fractions with heat recovery | |
| US2803685A (en) | Process for the extraction and recovery of aromatic hydrocarbons from hydrocarbon mixtures | |
| US2572583A (en) | Improved liquid-liquid contacting process using di(beta-cyanoethyl)-amine | |
| US3470088A (en) | Method for aromatic hydrocarbon recovery | |
| CA1262366A (en) | Extraction of aromatics with ethyl acetoacetate | |
| KR20240168973A (ko) | 추출물 재순환 스트림을 이용한 방향족의 액체-액체 추출 방법 | |
| CA1055876A (en) | Process for the separation of aromatic hydrocarbons from a mixed hydrocarbon feedstock | |
| US3674883A (en) | Recovering cyclopentadiene values from c{11 {11 fractions |