DE1941946B2 - Verfahren zur abtrennung von isopren aus dessen gemisch mit mindestens einem isoamylen und gegebenenfalls weiteren kohlenwasserstoffen mit 5 c-atomen - Google Patents
Verfahren zur abtrennung von isopren aus dessen gemisch mit mindestens einem isoamylen und gegebenenfalls weiteren kohlenwasserstoffen mit 5 c-atomenInfo
- Publication number
- DE1941946B2 DE1941946B2 DE19691941946 DE1941946A DE1941946B2 DE 1941946 B2 DE1941946 B2 DE 1941946B2 DE 19691941946 DE19691941946 DE 19691941946 DE 1941946 A DE1941946 A DE 1941946A DE 1941946 B2 DE1941946 B2 DE 1941946B2
- Authority
- DE
- Germany
- Prior art keywords
- sulfolane
- solvent
- isoprene
- column
- propiononitrile
- 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.)
- Granted
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 40
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 18
- 229930195733 hydrocarbon Natural products 0.000 title claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 title claims description 17
- 238000000926 separation method Methods 0.000 title description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 36
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 32
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 24
- -1 propionic acid nitrile Chemical class 0.000 claims description 22
- 235000019260 propionic acid Nutrition 0.000 claims description 18
- 239000000284 extract Substances 0.000 claims description 14
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000012071 phase Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 12
- 238000000895 extractive distillation Methods 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- 229910000336 copper(I) sulfate Inorganic materials 0.000 description 3
- WIVXEZIMDUGYRW-UHFFFAOYSA-L copper(i) sulfate Chemical compound [Cu+].[Cu+].[O-]S([O-])(=O)=O WIVXEZIMDUGYRW-UHFFFAOYSA-L 0.000 description 3
- 230000002706 hydrostatic effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical group CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- JEUAKJVLHISJDY-UHFFFAOYSA-N 2,3-dimethylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1C JEUAKJVLHISJDY-UHFFFAOYSA-N 0.000 description 1
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- ZCDDAQJNJWLCLL-UHFFFAOYSA-N 2-ethylthiolane 1,1-dioxide Chemical compound CCC1CCCS1(=O)=O ZCDDAQJNJWLCLL-UHFFFAOYSA-N 0.000 description 1
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 description 1
- SOZYDBBOFTUUPT-UHFFFAOYSA-N 3-ethylthiolane 1,1-dioxide Chemical compound CCC1CCS(=O)(=O)C1 SOZYDBBOFTUUPT-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- HXMSRXOTRGOTQZ-UHFFFAOYSA-N S1(=O)(=O)CCCC1.C(CC)#N Chemical compound S1(=O)(=O)CCCC1.C(CC)#N HXMSRXOTRGOTQZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- LEBJWEKXSNLCBQ-UHFFFAOYSA-M copper(1+);2,2,2-trifluoroacetate Chemical compound [Cu+].[O-]C(=O)C(F)(F)F LEBJWEKXSNLCBQ-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- DGTVXEHQMSJRPE-UHFFFAOYSA-M difluorophosphinate Chemical compound [O-]P(F)(F)=O DGTVXEHQMSJRPE-UHFFFAOYSA-M 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75348268A | 1968-08-19 | 1968-08-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1941946A1 DE1941946A1 (de) | 1970-02-26 |
| DE1941946B2 true DE1941946B2 (de) | 1977-08-04 |
| DE1941946C3 DE1941946C3 (cg-RX-API-DMAC10.html) | 1978-04-13 |
Family
ID=25030824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691941946 Granted DE1941946B2 (de) | 1968-08-19 | 1969-08-18 | Verfahren zur abtrennung von isopren aus dessen gemisch mit mindestens einem isoamylen und gegebenenfalls weiteren kohlenwasserstoffen mit 5 c-atomen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3520947A (cg-RX-API-DMAC10.html) |
| BE (1) | BE737586A (cg-RX-API-DMAC10.html) |
| CA (1) | CA927849A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1941946B2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2015905A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1214249A (cg-RX-API-DMAC10.html) |
| NL (1) | NL159076B (cg-RX-API-DMAC10.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819510A (en) * | 1972-09-21 | 1974-06-25 | Standard Oil Co | Method for producing high quality polymerization reaction media |
| CA1146978A (en) * | 1979-07-18 | 1983-05-24 | Henricus S.A. Douwes | Process for the recovery of isoprene, and isoprene so recovered |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3401112A (en) * | 1966-02-28 | 1968-09-10 | Shell Oil Co | Separation of hydrocarbons by cuprous salts |
-
1968
- 1968-08-19 US US753482A patent/US3520947A/en not_active Expired - Lifetime
-
1969
- 1969-08-18 BE BE737586D patent/BE737586A/xx unknown
- 1969-08-18 FR FR6928221A patent/FR2015905A1/fr not_active Withdrawn
- 1969-08-18 DE DE19691941946 patent/DE1941946B2/de active Granted
- 1969-08-18 CA CA059814A patent/CA927849A/en not_active Expired
- 1969-08-18 GB GB41050/69A patent/GB1214249A/en not_active Expired
- 1969-08-18 NL NL6912515.A patent/NL159076B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US3520947A (en) | 1970-07-21 |
| NL6912515A (cg-RX-API-DMAC10.html) | 1970-02-23 |
| DE1941946A1 (de) | 1970-02-26 |
| GB1214249A (en) | 1970-12-02 |
| NL159076B (nl) | 1979-01-15 |
| CA927849A (en) | 1973-06-05 |
| BE737586A (cg-RX-API-DMAC10.html) | 1970-02-18 |
| FR2015905A1 (cg-RX-API-DMAC10.html) | 1970-04-30 |
| DE1941946C3 (cg-RX-API-DMAC10.html) | 1978-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |