GB1591968A - Process for the preparation of 8-oxoacetals - Google Patents
Process for the preparation of 8-oxoacetals Download PDFInfo
- Publication number
- GB1591968A GB1591968A GB19655/78A GB1965578A GB1591968A GB 1591968 A GB1591968 A GB 1591968A GB 19655/78 A GB19655/78 A GB 19655/78A GB 1965578 A GB1965578 A GB 1965578A GB 1591968 A GB1591968 A GB 1591968A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- process according
- carbon atoms
- hydrogen
- alkyl
- 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 28
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000002841 Lewis acid Substances 0.000 claims abstract description 11
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- -1 tin halide Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052753 mercury Inorganic materials 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000011592 zinc chloride Substances 0.000 claims description 7
- 235000005074 zinc chloride Nutrition 0.000 claims description 7
- AIUVIHYATZICHW-UHFFFAOYSA-N 5,5-diethoxy-3-methylpent-3-en-2-one Chemical compound CCOC(OCC)C=C(C)C(C)=O AIUVIHYATZICHW-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- TXBMCLDHFRIQLA-UHFFFAOYSA-N trimethyl(3-methylbuta-1,3-dienoxy)silane Chemical compound CC(=C)C=CO[Si](C)(C)C TXBMCLDHFRIQLA-UHFFFAOYSA-N 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 4
- MXVNUXZQRXWKBU-UHFFFAOYSA-N 5,5-dimethoxy-3-methylpent-3-en-2-one Chemical compound COC(C=C(C(C)=O)C)OC MXVNUXZQRXWKBU-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002148 esters Chemical group 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000001030 gas--liquid chromatography Methods 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 abstract description 4
- 150000002905 orthoesters Chemical class 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 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 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- VNDYJBBGRKZCSX-UHFFFAOYSA-L Zinc bromide Inorganic materials Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- OPEGYIVFJNBLRP-UHFFFAOYSA-N buta-1,3-dienoxy(triethyl)silane Chemical compound CC[Si](CC)(CC)OC=CC=C OPEGYIVFJNBLRP-UHFFFAOYSA-N 0.000 description 1
- UQGOYQLRRBTVFM-UHFFFAOYSA-N buta-1,3-dienoxy(trimethyl)silane Chemical compound C[Si](C)(C)OC=CC=C UQGOYQLRRBTVFM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- FGCLOJOLJQDQOG-UHFFFAOYSA-N ethoxymethanediol Chemical class CCOC(O)O FGCLOJOLJQDQOG-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZYRRKOAAQBHXBT-UHFFFAOYSA-N hexa-1,3-dienoxy(trimethyl)silane Chemical compound CCC=CC=CO[Si](C)(C)C ZYRRKOAAQBHXBT-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- CGSRCFXAHZCJKA-UHFFFAOYSA-N trimethyl(2-methylbuta-1,3-dienoxy)silane Chemical compound C=CC(C)=CO[Si](C)(C)C CGSRCFXAHZCJKA-UHFFFAOYSA-N 0.000 description 1
- NGEIBAZWTYUUEI-UHFFFAOYSA-N trimethyl(2-methylhexa-1,3-dienoxy)silane Chemical compound CCC=CC(C)=CO[Si](C)(C)C NGEIBAZWTYUUEI-UHFFFAOYSA-N 0.000 description 1
- UDECNVKNELCBHM-UHFFFAOYSA-N trimethyl(3-methylidenepent-1-enoxy)silane Chemical compound C(C)C(C=CO[Si](C)(C)C)=C UDECNVKNELCBHM-UHFFFAOYSA-N 0.000 description 1
- YYBUYNRYATXXAT-UHFFFAOYSA-N trimethyl(3-methylpenta-1,3-dienoxy)silane Chemical compound CC=C(C)C=CO[Si](C)(C)C YYBUYNRYATXXAT-UHFFFAOYSA-N 0.000 description 1
- WKTNFXWRUHDTFA-UHFFFAOYSA-N trimethyl(4-methylpenta-1,3-dienoxy)silane Chemical compound CC(C)=CC=CO[Si](C)(C)C WKTNFXWRUHDTFA-UHFFFAOYSA-N 0.000 description 1
- QOMHQPJJGFLALB-UHFFFAOYSA-N trimethyl(5-methylhexa-3,5-dien-3-yloxy)silane Chemical compound CC(=C)C=C(CC)O[Si](C)(C)C QOMHQPJJGFLALB-UHFFFAOYSA-N 0.000 description 1
- RUQSUPCMWLPYOB-UHFFFAOYSA-N trimethyl(penta-2,4-dien-2-yloxy)silane Chemical compound C[Si](C)(C)OC(C)=CC=C RUQSUPCMWLPYOB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7715070A FR2391181A1 (fr) | 1977-05-17 | 1977-05-17 | Procede de preparation de d-oxoacetals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1591968A true GB1591968A (en) | 1981-07-01 |
Family
ID=9190911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19655/78A Expired GB1591968A (en) | 1977-05-17 | 1978-05-15 | Process for the preparation of 8-oxoacetals |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2654105A1 (fr) * | 1989-11-09 | 1991-05-10 | Univ Rouen | Nouveaux dienoxysilanes, leur procede d'obtention, et nouveaux aldehydes alpha-ethyleniques alpha-halogenes auxquels ils donnent acces. |
-
1977
- 1977-05-17 FR FR7715070A patent/FR2391181A1/fr active Granted
-
1978
- 1978-05-09 NL NLAANVRAGE7804965,A patent/NL188634C/xx not_active IP Right Cessation
- 1978-05-15 GB GB19655/78A patent/GB1591968A/en not_active Expired
- 1978-05-15 JP JP5672078A patent/JPS53141204A/ja active Granted
- 1978-05-16 BE BE187743A patent/BE867127A/xx not_active IP Right Cessation
- 1978-05-16 CH CH529178A patent/CH633246A5/fr not_active IP Right Cessation
- 1978-05-16 DD DD78205394A patent/DD135481A5/xx unknown
- 1978-05-16 CA CA303,499A patent/CA1108646A/fr not_active Expired
- 1978-05-16 HU HU78RO980A patent/HU179295B/hu not_active IP Right Cessation
- 1978-05-17 IT IT23510/78A patent/IT1096298B/it active
- 1978-05-17 DE DE19782821540 patent/DE2821540A1/de active Granted
- 1978-05-17 SU SU782615802A patent/SU869553A3/ru active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2654105A1 (fr) * | 1989-11-09 | 1991-05-10 | Univ Rouen | Nouveaux dienoxysilanes, leur procede d'obtention, et nouveaux aldehydes alpha-ethyleniques alpha-halogenes auxquels ils donnent acces. |
| EP0428460A1 (fr) * | 1989-11-09 | 1991-05-22 | Universite De Rouen | Nouveaux diénoxysilanes, leur procédé d'obtention, et nouveaux aldéhydes alpha-éthyléniques alpha-halogénés auxquels ils donnent accès |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2391181B1 (enrdf_load_stackoverflow) | 1981-01-09 |
| BE867127A (fr) | 1978-11-16 |
| NL188634C (nl) | 1992-08-17 |
| DE2821540C2 (enrdf_load_stackoverflow) | 1988-02-18 |
| DE2821540A1 (de) | 1978-11-23 |
| CA1108646A (fr) | 1981-09-08 |
| NL188634B (nl) | 1992-03-16 |
| HU179295B (en) | 1982-09-28 |
| CH633246A5 (en) | 1982-11-30 |
| NL7804965A (nl) | 1978-11-21 |
| IT7823510A0 (it) | 1978-05-17 |
| DD135481A5 (de) | 1979-05-09 |
| IT1096298B (it) | 1985-08-26 |
| FR2391181A1 (fr) | 1978-12-15 |
| SU869553A3 (ru) | 1981-09-30 |
| JPS53141204A (en) | 1978-12-08 |
| JPS6159298B2 (enrdf_load_stackoverflow) | 1986-12-16 |
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| Date | Code | Title | Description |
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| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950515 |