http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-812727-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_5bb89ee4c7370d063635e913bc926c49 |
| filingDate | 1956-09-11-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_4e43765a03c2a0c62237b7d078a00e80 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5b098ce28de4a84b6cc320db01f49bb8 |
| publicationDate | 1959-04-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-812727-A |
| titleOfInvention | A new process for the preparation of pseudo isomethyl ionone and the isomethyl ionones |
| abstract | Pseudo isomethyl ionone is obtained from mixtures thereof with pesudo normal methyl ionone which are made by condensing citral with butanone in the presence of a condensation agent consisting of a potassium cation or an organic cation in which all the valencies of the central atom are occupied by substituted or unsubstituted hydrocarbon groups, and of a basic anion with a base strength equal to or higher than the base strength of the cyanide anion and in the presence of a medium in which the solubility of the reactants is sufficiently high to allow the reaction to take place at a practical rate. The pseudo isomethyl ionone so obtained may be cyclized by known methods to give alpha or beta isomethyl ionone, or the mixture of pseudo isomethyl ionone with the normal isomer may be cyclized to give a mixture of the corresponding alpha or beta methyl ionones, from which the alpha or beta isomethyl ionone may be separated. In the condensation agent the organic cation may be quaternary ammonium such as tetramethyl, tetraethyl, trimethyl phenyl, trimethyl benzyl, triethyl benzyl, trimethyl myristyl and di-isobutyl cresoxy ethoxy ethyl dimethyl benzyl ammonium, benzyl pyridinium, and ethyl quinolinium, quaternary phosphonium such as triethyl benzyl phosphonium, ternary sulphonium such as trimethyl sulphonium or methyl benzyl butyl sulphonium, quaternary arsonium such as triphenyl methylarsonium, or quaternary stibonium. It is indicated that the cations of lithium, sodium, rubidium and caesium are unsuitable for use in the reaction. The anions mentioned are hydroxide, alcoholate and cyanide. It is stated that halide and acetate anions are inactive. The condensation agent may be made by addition of moist silver oxide or an alkali-metal hydroxide, alcoholate or cyanide to a solution of a quaternary ammonium salt in water, alcohol or pyridine, or by treating tertiary amines, phosphines, arsines or stibines or a secondary sulphide with an alkyl, aryl or aralkyl halide, e.g. triethylamino with benzyl chloride, triethyl phosphine with benzyl chloride, triphenyl arsine with methyl iodide, or methyl benzyl sulphide with butyl iodide, followed by addition of an alkaline agent such as potassium hydroxide or sodium methoxide. The condensation may be conducted in a medium of aliphatic alcohols containing from 1 to 4 carbon atoms such as methanol, ethanol, or isopropanol, ethyl butyl ether, pyridine, or benzyl alcohol. Water may or may not be present. The mixture of pseudo methyl ionones obtained may be cyclized with phosphoric acid or boron trifluoride to give alpha methyl ionones. Separation of the isomeric pseudo compounds or of the isomethyl ionones from the mixed ionones obtained by cyclization may be effected by fractional distillation. The proportion of pseudo isomethyl ionone in the mixture obtained from the condensation is determined by semicarbazide formation. Examples are given. |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 103.