UST102908I4 - Catalyzed transesterification synthesis - Google Patents
Catalyzed transesterification synthesis Download PDFInfo
- Publication number
- UST102908I4 UST102908I4 US06/382,007 US38200782A UST102908I4 US T102908 I4 UST102908 I4 US T102908I4 US 38200782 A US38200782 A US 38200782A US T102908 I4 UST102908 I4 US T102908I4
- Authority
- US
- United States
- Prior art keywords
- lower alkyl
- formula
- catalyst
- carbon atoms
- phenoxy
- 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.)
- Pending
Links
- 238000005809 transesterification reaction Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- -1 lower alkyl phenoxy Chemical group 0.000 abstract 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- QPTWKDNRYCGMJM-UHFFFAOYSA-N ethyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C(Cl)Cl)C1(C)C QPTWKDNRYCGMJM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 230000002459 sustained effect Effects 0.000 abstract 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of the formula ##STR1## wherein X is chlorine or bromine and B is a benzyl group of the formula ##STR2## where Y and Z may be the same or different and are selected from the group consisting of hydrogen, halogen, lower alkyl, lowr alkoxy, phenyl, phenoxy, lower alkyl phenyl, lower alkyl phenoxy, halophenyl and halophenoxy, are prepared by transesterification between BOH and a compound of the formula ##STR3## wherein L is a lower alkyl radical of between 1 and 4 carbon atoms, using as catalyst an organometallic compound selected from (RO)4 Ti and R'2 SnO, where R and R' are alkyl radicals of between 1 and 6 carbon atoms.
Useful organometallic catalysts include tetrabutyl titanate, tetraisopropyl titanate, and dibutyl tin(IV)oxide. About 1% by weight of the total charge of reactants is catalyst.
The process is conducted at 100°-200° C. under vacuum, generally in the absence of solvent, with sustained distillation of the LOH by-product until the theoretical amount of alcohol is collected. The product ester is then distilled under vacuum.
For example, 126 g ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, 100 g m-phenoxybenzyl alcohol, and 2.25 grams of tetraisopropyl titanate reacted at 150° C./200 mm Hg yielded the m-phenoxybenzyl ester; bp 181° C./0.1 mm Hg, 89% yield, 99.5% pure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/382,007 UST102908I4 (en) | 1977-05-27 | 1982-05-25 | Catalyzed transesterification synthesis |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80134577A | 1977-05-27 | 1977-05-27 | |
| US06/382,007 UST102908I4 (en) | 1977-05-27 | 1982-05-25 | Catalyzed transesterification synthesis |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US80134577A Continuation | 1977-05-27 | 1977-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UST102908I4 true UST102908I4 (en) | 1983-04-05 |
Family
ID=27009596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/382,007 Pending UST102908I4 (en) | 1977-05-27 | 1982-05-25 | Catalyzed transesterification synthesis |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | UST102908I4 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147645A (en) * | 1988-06-21 | 1992-09-15 | Basf Aktiengesellschaft | Pyrethroids and their use for controlling pests |
| US6441220B1 (en) * | 1999-06-16 | 2002-08-27 | Sumitomo Chemical Company, Limited | Methods for producing cyclopropane carboxylates |
-
1982
- 1982-05-25 US US06/382,007 patent/UST102908I4/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147645A (en) * | 1988-06-21 | 1992-09-15 | Basf Aktiengesellschaft | Pyrethroids and their use for controlling pests |
| US6441220B1 (en) * | 1999-06-16 | 2002-08-27 | Sumitomo Chemical Company, Limited | Methods for producing cyclopropane carboxylates |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1241662A (en) | Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters | |
| EP0298734B1 (en) | Organosilicon compounds | |
| DE69703138T2 (en) | Process for the preparation of substituted hydroxy hydrocinnamate esters | |
| EP0334951A1 (en) | High yield method for preparation of dialkyl esters of polyhaloaromatic acids | |
| UST102908I4 (en) | Catalyzed transesterification synthesis | |
| EP0447141B1 (en) | Hafnium-catalyzed transesterification | |
| US5679821A (en) | Process for preparing organosilicon compound | |
| US5068382A (en) | Process for the production of organosilicon compounds | |
| DE2626173C2 (en) | 2-Methylenopropane-1,3-diol-bis-acetic acid ester and its use | |
| JP2002179619A (en) | Method for producing methylcyclohexyl(meth)acrylate | |
| ES8106693A1 (en) | Carboxylic ester compounds for use as insecticides | |
| CA1333615C (en) | Transesterification of alkoxyesters | |
| JPS5527147A (en) | Preparation of carboxylic acid having aryl substituent | |
| AU527266B2 (en) | Oxyimino-substituted cyclopropanecarboxylate esters | |
| US4827002A (en) | Process for preparing adducts of alcohols, ethers and esters with 1,2-dichlorodifluoroethylene | |
| US4324736A (en) | Tetravalent vanadium compounds which are soluble in organic solvents | |
| US6114562A (en) | Organosilicon compounds and method of making | |
| EP0253536A3 (en) | Fluorobenzyl esters | |
| EP0714886B1 (en) | Copolymerisable oxime ether | |
| JPS54163517A (en) | Production of dialkylaminoalkyl acrylate or dialkylaminoalkyl methacrylate | |
| JPS5538806A (en) | Catalyst for preparation of polyethylene | |
| JPS6450887A (en) | Organosilicon compound | |
| UST102907I4 (en) | Process to 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate | |
| JPH0797351A (en) | Novel (meth) acrylate compound and method for producing the same | |
| JPH0730096B2 (en) | α-Trifluoromethylacrylic acid triorganosilyl methyl ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |