DE2346201C2 - Verfahren zur Herstellung von ω-Cyan-derivaten von β-Alkoxycarbonsäureestern - Google Patents
Verfahren zur Herstellung von ω-Cyan-derivaten von β-AlkoxycarbonsäureesternInfo
- Publication number
- DE2346201C2 DE2346201C2 DE19732346201 DE2346201A DE2346201C2 DE 2346201 C2 DE2346201 C2 DE 2346201C2 DE 19732346201 DE19732346201 DE 19732346201 DE 2346201 A DE2346201 A DE 2346201A DE 2346201 C2 DE2346201 C2 DE 2346201C2
- Authority
- DE
- Germany
- Prior art keywords
- acetal
- ketene
- acid esters
- preparation
- cyano
- 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 description 10
- 150000002148 esters Chemical class 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 20
- 150000001241 acetals Chemical class 0.000 description 19
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DBHUNTXEFPOUMO-UHFFFAOYSA-N 5-cyano-3-ethoxypentanoic acid Chemical compound C(#N)CCC(CC(=O)O)OCC DBHUNTXEFPOUMO-UHFFFAOYSA-N 0.000 description 1
- YQRUUUIQYKQZCE-UHFFFAOYSA-N 5-cyano-3-methoxypentanoic acid Chemical compound C(#N)CCC(CC(=O)O)OC YQRUUUIQYKQZCE-UHFFFAOYSA-N 0.000 description 1
- FNEARBHZFXEPFD-UHFFFAOYSA-N 5-oxopentanenitrile Chemical compound O=CCCCC#N FNEARBHZFXEPFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- -1 α-cyano acetal Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7212604A NL7212604A (OSRAM) | 1972-09-16 | 1972-09-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2346201A1 DE2346201A1 (de) | 1974-03-28 |
| DE2346201C2 true DE2346201C2 (de) | 1983-10-27 |
Family
ID=19816955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732346201 Expired DE2346201C2 (de) | 1972-09-16 | 1973-09-13 | Verfahren zur Herstellung von ω-Cyan-derivaten von β-Alkoxycarbonsäureestern |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE804866A (OSRAM) |
| CA (1) | CA1013760A (OSRAM) |
| CH (1) | CH593243A5 (OSRAM) |
| DE (1) | DE2346201C2 (OSRAM) |
| FR (1) | FR2200254B1 (OSRAM) |
| GB (1) | GB1385637A (OSRAM) |
| IT (1) | IT1000069B (OSRAM) |
| NL (1) | NL7212604A (OSRAM) |
| SU (1) | SU468401A3 (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067798B (de) * | 1958-08-04 | 1959-10-29 | Wacker Chemie Gmbh | Verfahren zur Herstellung von beta-Alkoxycarbonsaeureestern |
-
1972
- 1972-09-16 NL NL7212604A patent/NL7212604A/xx not_active Application Discontinuation
-
1973
- 1973-09-13 DE DE19732346201 patent/DE2346201C2/de not_active Expired
- 1973-09-14 BE BE135658A patent/BE804866A/xx not_active IP Right Cessation
- 1973-09-14 CH CH1323173A patent/CH593243A5/xx not_active IP Right Cessation
- 1973-09-14 SU SU1962272A patent/SU468401A3/ru active
- 1973-09-14 GB GB4325073A patent/GB1385637A/en not_active Expired
- 1973-09-14 CA CA181,119A patent/CA1013760A/en not_active Expired
- 1973-09-14 FR FR7333071A patent/FR2200254B1/fr not_active Expired
- 1973-09-17 IT IT5256573A patent/IT1000069B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| CH593243A5 (OSRAM) | 1977-11-30 |
| BE804866A (fr) | 1974-03-14 |
| CA1013760A (en) | 1977-07-12 |
| IT1000069B (it) | 1976-03-30 |
| SU468401A3 (ru) | 1975-04-25 |
| NL7212604A (OSRAM) | 1974-03-19 |
| FR2200254A1 (OSRAM) | 1974-04-19 |
| DE2346201A1 (de) | 1974-03-28 |
| FR2200254B1 (OSRAM) | 1977-05-20 |
| GB1385637A (en) | 1975-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |