CA1118443A - Process for the separation of stereoisomeric vinylcyclopropanecarboxylic acids - Google Patents
Process for the separation of stereoisomeric vinylcyclopropanecarboxylic acidsInfo
- Publication number
- CA1118443A CA1118443A CA000301172A CA301172A CA1118443A CA 1118443 A CA1118443 A CA 1118443A CA 000301172 A CA000301172 A CA 000301172A CA 301172 A CA301172 A CA 301172A CA 1118443 A CA1118443 A CA 1118443A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- cis
- distillation
- effected
- trans
- 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
- 238000000034 method Methods 0.000 title claims abstract description 22
- PDOBSLHNWIVQJX-UHFFFAOYSA-N 1-ethenylcyclopropane-1-carboxylic acid Chemical class OC(=O)C1(C=C)CC1 PDOBSLHNWIVQJX-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000000926 separation method Methods 0.000 title claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- YACLCMMBHTUQON-UHFFFAOYSA-N 1-chloro-1-fluoroethane Chemical compound CC(F)Cl YACLCMMBHTUQON-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 238000004508 fractional distillation Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000017105 transposition Effects 0.000 claims description 2
- 229950005499 carbon tetrachloride Drugs 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 7
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000009183 running Effects 0.000 description 3
- 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 2
- 238000001816 cooling Methods 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 description 1
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2716898.5 | 1977-04-16 | ||
| DE2716898A DE2716898B2 (de) | 1977-04-16 | 1977-04-16 | Verfahren zur Trennung von cis- und trans-Vinylcyclopropancarbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1118443A true CA1118443A (en) | 1982-02-16 |
Family
ID=6006442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000301172A Expired CA1118443A (en) | 1977-04-16 | 1978-04-14 | Process for the separation of stereoisomeric vinylcyclopropanecarboxylic acids |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS53130639A (cs) |
| AT (1) | AT353772B (cs) |
| BE (1) | BE865983A (cs) |
| BR (1) | BR7802324A (cs) |
| CA (1) | CA1118443A (cs) |
| CS (1) | CS199725B2 (cs) |
| DD (1) | DD136046A5 (cs) |
| DE (1) | DE2716898B2 (cs) |
| DK (1) | DK164978A (cs) |
| ES (1) | ES468825A1 (cs) |
| FR (1) | FR2387210A1 (cs) |
| GB (1) | GB1570557A (cs) |
| HU (1) | HU174669B (cs) |
| IL (1) | IL54498A (cs) |
| IT (1) | IT7822335A0 (cs) |
| NL (1) | NL7803994A (cs) |
| SU (1) | SU703014A3 (cs) |
| ZA (1) | ZA782157B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010875B1 (en) * | 1978-10-27 | 1983-06-22 | Imperial Chemical Industries Plc | Process of separating cis and trans isomers of cyclopropane carboxylic acids |
| DE3613975A1 (de) * | 1986-04-25 | 1987-10-29 | Bayer Ag | Trennung von diastereomeren |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4931978A (cs) * | 1972-07-29 | 1974-03-23 |
-
1977
- 1977-04-16 DE DE2716898A patent/DE2716898B2/de not_active Withdrawn
-
1978
- 1978-04-11 GB GB14136/78A patent/GB1570557A/en not_active Expired
- 1978-04-13 IL IL54498A patent/IL54498A/xx unknown
- 1978-04-13 HU HU78BA3648A patent/HU174669B/hu unknown
- 1978-04-14 IT IT7822335A patent/IT7822335A0/it unknown
- 1978-04-14 JP JP4340078A patent/JPS53130639A/ja active Pending
- 1978-04-14 FR FR7811076A patent/FR2387210A1/fr active Granted
- 1978-04-14 DD DD78204799A patent/DD136046A5/xx unknown
- 1978-04-14 NL NL7803994A patent/NL7803994A/xx not_active Application Discontinuation
- 1978-04-14 BE BE186788A patent/BE865983A/xx unknown
- 1978-04-14 CA CA000301172A patent/CA1118443A/en not_active Expired
- 1978-04-14 ES ES468825A patent/ES468825A1/es not_active Expired
- 1978-04-14 CS CS782447A patent/CS199725B2/cs unknown
- 1978-04-14 BR BR7802324A patent/BR7802324A/pt unknown
- 1978-04-14 DK DK164978A patent/DK164978A/da not_active IP Right Cessation
- 1978-04-14 AT AT262478A patent/AT353772B/de not_active IP Right Cessation
- 1978-04-14 ZA ZA00782157A patent/ZA782157B/xx unknown
- 1978-04-14 SU SU782602553A patent/SU703014A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| IL54498A0 (en) | 1978-07-31 |
| JPS53130639A (en) | 1978-11-14 |
| NL7803994A (nl) | 1978-10-18 |
| ES468825A1 (es) | 1978-12-01 |
| DE2716898B2 (de) | 1979-02-15 |
| BR7802324A (pt) | 1978-12-19 |
| HU174669B (hu) | 1980-03-28 |
| DD136046A5 (de) | 1979-06-13 |
| FR2387210A1 (fr) | 1978-11-10 |
| DK164978A (da) | 1978-10-17 |
| BE865983A (fr) | 1978-10-16 |
| DE2716898A1 (de) | 1978-10-19 |
| AT353772B (de) | 1979-12-10 |
| SU703014A3 (ru) | 1979-12-05 |
| IL54498A (en) | 1981-06-29 |
| ATA262478A (de) | 1979-05-15 |
| IT7822335A0 (it) | 1978-04-14 |
| FR2387210B1 (cs) | 1981-08-07 |
| ZA782157B (en) | 1979-03-28 |
| CS199725B2 (en) | 1980-07-31 |
| GB1570557A (en) | 1980-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH046694B2 (cs) | ||
| JP3782051B2 (ja) | メソ−ゼアキサンチンの製造方法 | |
| US4196304A (en) | Separation of stereoisomeric cyclic carboxylic acids | |
| Dawson et al. | Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity | |
| CA1118443A (en) | Process for the separation of stereoisomeric vinylcyclopropanecarboxylic acids | |
| EP0511947B1 (en) | Process for the purification of 2,6-diisopropyl phenol | |
| US4345090A (en) | Process for preparing menthyl esters of enantiomers of chiral 3-(2,2-dichloro- and -dibromo-vinyl)-2,2-dimethylcyclopropanecarboxylic acids | |
| US4673761A (en) | Process for preparing anti-inflammatory cycloalkylidenemethylphenylacetic acid derivatives | |
| Horning et al. | Preparation of 3-methyl-5-aryl-2-cyclohexen-1-ones | |
| US4427598A (en) | Process for preparing cyclopropane carboxylic acid ester derivatives | |
| US3989758A (en) | Monoacetals of unsaturated aliphatic dialdehydes | |
| US4284796A (en) | Preparation of 4-acyloxy-2-methyl-crotonaldehydes | |
| Nair et al. | Improved synthesis of monofluoro-and monochloropyruvic acids | |
| US4259253A (en) | Process for the preparation of stereospecific trans, trans-farnesylacetic acid | |
| US4179446A (en) | Sex pheromone produced by the female Japanese beetle: specificity of male response to enantiomers | |
| Wailes | The synthesis of the stereoisomeric hexadeca-2, 4-dienoic acids and their isobutylamides | |
| EP0043143B1 (en) | Process for stereoselectively synthetizing cyclopropane carboxylates as intermediates for pyrethroids | |
| Baldwin et al. | Relative configurations of the chiral 2, 7-and 3, 7-dimethyl-7-(methoxymethyl) cyclohepta-1, 3, 5-trienes | |
| US4914229A (en) | Novel preparation of compounds of the 4-oxodamascone series, and novel scents from this class of compounds | |
| EP0842137B1 (en) | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor | |
| US4009202A (en) | 2(or 3)-methyl-1-acetoxy-4-alkoxy (or phenoxy)-1,3-butadienes | |
| US4419524A (en) | Process for the preparation of dihalovinylcyclopropanecarboxylic acids | |
| Elliott | 999. The pyrethrins and related compounds. Part V. Purification of (+)-pyrethrolone as the monohydrate, and the nature of “pyrethrolone-C” | |
| DE3429183C1 (de) | Verfahren zur Gewinnung von reinem Benzoesäuremethylester | |
| EP0032712B1 (en) | New process for preparing unsaturated bicyclic hydrocarbons |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |