http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-599366-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6108c9a7f7a472c2db8923daca0ec8d6 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C08K5-156 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D317-12 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D317-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C08K5-156 |
| filingDate | 1945-09-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1948-03-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-599366-A |
| titleOfInvention | Improvements in the production of cyclic acetals |
| abstract | 1 : 2 : 5 : 6-Tetrahydrobenzaldehyde ethylene acetal is prepared by reacting 1 : 2 : 5 : 6-tetrahydrobenzaldehyde with ethylene oxide in the presence of an acid-acting catalyst, which is, preferably, an acidic metal chloride such as anhydrous stannic chloride or lead tetrachloride. Advantageously, the aldehyde is dissolved in an anhydrous inert solvent, the catalyst added and ethylene oxide passed in with agitation at 40-50 DEG C. in an amount of 50 to 75 per cent of the weight of the aldehyde; the catalyst may then be neutralized, extracted with water and the ethylene acetal extracted from the residue with ethanol. The acetal may be reduced to hexahydrobenzaldehyde ethylene acetal, or oxidized to 3 : 4-dihydroxy-hexahydrobenzaldehyde ethylene acetal, whose hydroxyl groups may be esterified, for example, by means of an acid-chloride or anhydride or etherified, for example, by means of a dialkyl sulphate. The products of the invention are stated to be novel and find use as plasticisers for thermoplastics, especially cellulose acetate and other organic derivatives of cellulose, and as perfumes and intermediates. In examples: (1) 1 : 2 : 5 : 6-tetrahydrobenzaldehyde ethylene acetal is prepared by reacting ethylene oxide with the aldehyde in benzene solution using stannic chloride as catalyst; the ethylene acetal is (2) hydrogenated in ethanol in the presence of Raney nickel yielding hexahydrobenzaldehyde ethylene acetal and (3) oxidized by means of aqueous permanganate yielding 3 : 4-dihydroxy-hexahydrobenzaldehyde ethylene acetal which is (4) etherified by dissolving it in diethyl ether, adding sodium and then reacting with dimethyl sulphate yielding the 3 : 4-dimethoxy derivative, or (5) is esterified to the 3 : 4-diacetoxy compound by refluxing with acetic anhydride. Other similar esters and ethers may be formed; thus, etherifying groups may be ethyl, propyl, isopropyl, butyl, amyl, lauryl, vinyl, halogen or hydroxyl substituted alkyl groups, cyclohexyl, cyclohexenyl, phenyl, naphthyl, tolyl, cumyl, benzyl and halogen or other nuclear substituted aryl groups. 1 : 2 : 5 : 6-Tetrahydrobenzaldehyde may be made by the Diels-Alder synthesis from acrolein and 1 : 3-butadiene. |
| priorityDate | 1944-09-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 54.