CA1123004A - Preparation of methyl and ethyl esters - Google Patents
Preparation of methyl and ethyl estersInfo
- Publication number
- CA1123004A CA1123004A CA306,002A CA306002A CA1123004A CA 1123004 A CA1123004 A CA 1123004A CA 306002 A CA306002 A CA 306002A CA 1123004 A CA1123004 A CA 1123004A
- Authority
- CA
- Canada
- Prior art keywords
- group
- carbon atoms
- reaction
- nitrile
- methyl
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title description 5
- 125000004494 ethyl ester group Chemical group 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- -1 dimethylvinyl group Chemical group 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000001117 sulphuric acid Substances 0.000 claims abstract description 6
- 235000011149 sulphuric acid Nutrition 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 4
- 239000007809 chemical reaction catalyst Substances 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000002516 radical scavenger Substances 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- HFUWHULRJBGIQJ-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrile Chemical compound CC1(C)C(C=C(Cl)Cl)C1C#N HFUWHULRJBGIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- WDSAIUNCHKDXDU-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonitrile Chemical compound CC(C)=CC1C(C#N)C1(C)C WDSAIUNCHKDXDU-UHFFFAOYSA-N 0.000 claims description 2
- KJYYKNQFSYTVPY-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonitrile Chemical compound CC1(C)C(C=C(Br)Br)C1C#N KJYYKNQFSYTVPY-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- RKURKRQKAOQDBG-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropane-1-carbonitrile Chemical compound CC1(C)C(C#N)C1(C)C RKURKRQKAOQDBG-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 7
- 238000006136 alcoholysis reaction Methods 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000003482 Pinner synthesis reaction Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- 238000010932 ethanolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- JCHUCGKEGUAHEH-UHFFFAOYSA-N 1,1,2,2-tetramethylcyclopropane Chemical compound CC1(C)CC1(C)C JCHUCGKEGUAHEH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- QJOOIMSFFIUFKX-UHFFFAOYSA-N methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(Cl)Cl)C1(C)C QJOOIMSFFIUFKX-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30470/77A GB1599888A (en) | 1977-07-20 | 1977-07-20 | Preparation of methyl and ethyl esters of cyclopropane carboxylic acids |
| GB30470/77 | 1977-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123004A true CA1123004A (en) | 1982-05-04 |
Family
ID=10308187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA306,002A Expired CA1123004A (en) | 1977-07-20 | 1978-06-22 | Preparation of methyl and ethyl esters |
Country Status (13)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ185635A (en) * | 1976-11-18 | 1980-04-28 | Ici Ltd | Preparation of 3-dihalovinyl-2,2-dimethylcyclopropane carboxylic acid derivatives |
| AU4839279A (en) * | 1978-07-18 | 1980-01-24 | Imperial Chemical Industries Ltd. | Cyclopropane carboxylic acids |
| JPS5793493U (enrdf_load_stackoverflow) * | 1980-11-28 | 1982-06-09 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1553818A (en) * | 1975-07-24 | 1979-10-10 | Nat Res Dev | Synthesis of cyclopropane carboxylic acids |
| NZ185635A (en) * | 1976-11-18 | 1980-04-28 | Ici Ltd | Preparation of 3-dihalovinyl-2,2-dimethylcyclopropane carboxylic acid derivatives |
-
1977
- 1977-07-20 GB GB30470/77A patent/GB1599888A/en not_active Expired
-
1978
- 1978-06-22 CA CA306,002A patent/CA1123004A/en not_active Expired
- 1978-07-11 BE BE1008978A patent/BE868901A/xx not_active IP Right Cessation
- 1978-07-18 NL NL7807658A patent/NL7807658A/xx not_active Application Discontinuation
- 1978-07-18 LU LU79993A patent/LU79993A1/xx unknown
- 1978-07-18 BR BR7804637A patent/BR7804637A/pt unknown
- 1978-07-18 IE IE1441/78A patent/IE47130B1/en not_active IP Right Cessation
- 1978-07-18 JP JP8682978A patent/JPS5422345A/ja active Granted
- 1978-07-18 CH CH774278A patent/CH635064A5/de not_active IP Right Cessation
- 1978-07-18 DK DK321978A patent/DK158343C/da not_active IP Right Cessation
- 1978-07-18 DE DE19782831555 patent/DE2831555A1/de active Granted
- 1978-07-18 IT IT25820/78A patent/IT1097870B/it active
- 1978-07-18 FR FR7821245A patent/FR2398042A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH635064A5 (en) | 1983-03-15 |
| DK158343C (da) | 1990-10-01 |
| IE781441L (en) | 1979-01-20 |
| JPS6145612B2 (enrdf_load_stackoverflow) | 1986-10-08 |
| JPS5422345A (en) | 1979-02-20 |
| LU79993A1 (fr) | 1979-04-09 |
| BR7804637A (pt) | 1979-04-17 |
| IE47130B1 (en) | 1983-12-28 |
| FR2398042A1 (fr) | 1979-02-16 |
| IT1097870B (it) | 1985-08-31 |
| DK158343B (da) | 1990-05-07 |
| BE868901A (nl) | 1979-01-11 |
| GB1599888A (en) | 1981-10-07 |
| FR2398042B1 (enrdf_load_stackoverflow) | 1983-04-29 |
| IT7825820A0 (it) | 1978-07-18 |
| DE2831555A1 (de) | 1979-02-01 |
| DE2831555C2 (enrdf_load_stackoverflow) | 1987-09-10 |
| NL7807658A (nl) | 1979-01-23 |
| DK321978A (da) | 1979-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |