http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-820296-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_2fa8f8941ecc2d9521285617dbb93322 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D307-20 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D307-20 |
| filingDate | 1957-05-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_644143bd0105a5dd9ce46a69bd43955a |
| publicationDate | 1959-09-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-820296-A |
| titleOfInvention | Process for the production of 3-chloro-4-hydroxytetrahydrofuran |
| abstract | The adipic acid ester of mixed geometric isomers of 3-chloro-4-hydroxytetrahydrofuran is compatible with polyvinyl chloride and is a good plasticizer therefor in all proportions.ALSO:3-Chloro-4-hydroxytetrahydrofuran is prepared by heating 1 : 2-dichloro-3 : 4-dihydroxybutane under neutral or acid conditions whereby hydrogen chloride is eliminated between the terminal hydroxy and chloro groups. The low boiling isomer of the product, B.P. 87-90 DEG C. at 15 mm. Hg., is novel. The 1 : 3-dichloro-3 : 4-dihydroxybutane may be present in the reaction mixture as such or may be formed in situ, e.g. from the mono- or di-esters with carboxylic acids such as acetic or formic acids by hydrolysis or by alcoholysis in the presence of p-toluene sulphonic acid or sulphuric acid. The glycol exists as two geometric isomers which can be used to produce the corresponding geometric isomers of the tetrahydrofuran compound, or a mixture of isomers may be used, the isomers of the product being separated by fractional distillation. The cyclisation may take place at temperatures above 70 DEG C. and generally below 250 DEG C. Liquid diluents may be present, the heating being effected so that the diluent refluxes. A preferred procedure comprises reacting 1 : 2-dichlorobutene-3 with hydrogen peroxide in the presence of formic or acetic acid to produce 1 : 2-dichloro-3 : 4-epoxybutane or a mono ester of 1 : 3-dichloro-3 : 4-dihydroxybutane, converting the 1 : 2-dichloro-3 : 4-epoxybutane to 1 : 2-dichloro-3 : 4-dihydroxy-butane or to mono- or di-carboxylic acid esters thereof, and heating the glycol or esters under neutral or acid conditions to produce 3-chloro-4-hydroxytetrahydrofuran. Both geometric forms of the product are valuable solvents and by esterifying the free hydroxy group, e.g. with adipic acid to form the adipate, useful plasticizers for polymeric resins are obtained. |
| priorityDate | 1957-05-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 37.