CA1146978A - Process for the recovery of isoprene, and isoprene so recovered - Google Patents
Process for the recovery of isoprene, and isoprene so recoveredInfo
- Publication number
- CA1146978A CA1146978A CA000352244A CA352244A CA1146978A CA 1146978 A CA1146978 A CA 1146978A CA 000352244 A CA000352244 A CA 000352244A CA 352244 A CA352244 A CA 352244A CA 1146978 A CA1146978 A CA 1146978A
- Authority
- CA
- Canada
- Prior art keywords
- isoprene
- liquid
- sulfolane
- fraction
- counter
- 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 title claims abstract description 142
- 238000000034 method Methods 0.000 title claims description 24
- 238000011084 recovery Methods 0.000 title description 4
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 64
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 64
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 39
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000284 extract Substances 0.000 claims abstract description 34
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 238000009835 boiling Methods 0.000 claims abstract description 21
- 238000000638 solvent extraction Methods 0.000 claims abstract description 20
- 238000000622 liquid--liquid extraction Methods 0.000 claims abstract description 19
- 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 abstract description 19
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 9
- 238000000605 extraction Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 16
- 238000004508 fractional distillation Methods 0.000 claims description 15
- PMJHHCWVYXUKFD-UHFFFAOYSA-N pentadiene group Chemical class C=CC=CC PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 12
- -1 isoprene Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004821 distillation Methods 0.000 abstract description 9
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-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
- 239000007788 liquid Substances 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 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
- 239000005864 Sulphur Substances 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
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- IIIGXUANQZOIHI-UHFFFAOYSA-N 1,1-dioxothiolan-2-amine Chemical class NC1CCCS1(=O)=O IIIGXUANQZOIHI-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 class O=S1(=O)CCCC1SC1S(=O)(=O)CCC1 QAHXBUGLZGGVEM-UHFFFAOYSA-N 0.000 description 1
- DNCGEOYDGQJILX-UHFFFAOYSA-N 2-nitrothiolane 1,1-dioxide Chemical class [O-][N+](=O)C1CCCS1(=O)=O DNCGEOYDGQJILX-UHFFFAOYSA-N 0.000 description 1
- 241000905957 Channa melasoma 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
- 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
- 241000283986 Lepus Species 0.000 description 1
- 235000018734 Sambucus australis Nutrition 0.000 description 1
- 244000180577 Sambucus australis Species 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 241000927721 Tritia Species 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 150000001875 compounds Chemical class 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
- 238000005336 cracking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002485 inorganic esters Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 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
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical class CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000000926 separation method 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
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7925028 | 1979-07-18 | ||
| GB7925028 | 1979-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1146978A true CA1146978A (en) | 1983-05-24 |
Family
ID=10506576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000352244A Expired CA1146978A (en) | 1979-07-18 | 1980-05-20 | Process for the recovery of isoprene, and isoprene so recovered |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0023370B1 (https=) |
| JP (1) | JPS5616426A (https=) |
| CA (1) | CA1146978A (https=) |
| DE (1) | DE3064122D1 (https=) |
| ES (1) | ES8202529A1 (https=) |
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 |
| CN121889199A (zh) * | 2023-10-06 | 2026-04-17 | 苏尔寿管理有限公司 | 使用改进的萃取剂用于分离c6-c9-芳族烃和异戊二烯的方法 |
| 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 |
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 (https=) * | 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/ES8202529A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES493414A0 (es) | 1981-08-01 |
| DE3064122D1 (en) | 1983-08-18 |
| EP0023370B1 (en) | 1983-07-13 |
| JPS5616426A (en) | 1981-02-17 |
| EP0023370A1 (en) | 1981-02-04 |
| JPS6251939B2 (https=) | 1987-11-02 |
| ES8202529A1 (es) | 1981-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |