Preparation of Chlorofluoro Derivatives of Ethylbenzene

McBee, E. T.; Hass, H. B.; Rothrock, G.; Newcomer, J. S.; Clipp, W.; Welch, Z.; Gochenour, C.

doi:10.1021/ie50447a631

Cited by 6 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chlorination with chlorine, ferric chloride and/or iron of ethylbenzene [74,75], isopropylbenzene [74], and 1,4-dibutylbenzene [74] gives perchlorobenzene, the conversion being favoured by longer reaction times and/or higher temperatures [74]. With ethylbenzene, ethyl chloride is formed, indicating that chlorinolysis occurs prior to side-chain chlorination.…”

Section: (D) By Chlorinolysis Of Alkylbenzenesmentioning

confidence: 99%

“…(1) (4) C Cl (2) (3) (4) (5) (6) Perhalo compounds of type C6 CIs C2 F x CIs _ x when chlorinated with chlorine and ferric chloride or treated with antimony pentafluoride give perchlorobenzene [75]. In the latter case, it is assumed that antimony chlorofluorides are formed by chlorine-fluorine exchange, causing subsequent chlorinolysis.…”

Section: (D) By Chlorinolysis Of Alkylbenzenesmentioning

confidence: 99%

“…McBee and co-workers obtained, by perchlorination with chlorine and white light, phenylpentachloroethane and, at higher temperatures (130°), a pentachloroethylchlorobenzene [75). Phenylpentachloroethane when submitted to aromatic perchlorination with chlorine and ferric chloride at 140-160° gives, presumably, oH-nonachloroethylbenzene which, at higher temperatures, yields perchlorobenzene.…”

Section: Perchloroethylbenzenementioning

confidence: 99%

See 2 more Smart Citations

Aromatic and Alkaromatic Chlorocarbons

Ballester

Olivella

1974

Polychloroaromatic Compounds

View full text Add to dashboard Cite

Section: (D) By Chlorinolysis Of Alkylbenzenesmentioning

confidence: 99%

Section: (D) By Chlorinolysis Of Alkylbenzenesmentioning

confidence: 99%

Section: Perchloroethylbenzenementioning

confidence: 99%

See 1 more Smart Citation

Aromatic and Alkaromatic Chlorocarbons

Ballester

Olivella

1974

Polychloroaromatic Compounds

View full text Add to dashboard Cite

Studies on the chlorination of the side chains of alkylaromatic compounds

Harvey¹,

Smith²,

Stacey³

et al. 1954

J. Appl. Chem.

View full text Add to dashboard Cite

Photochemical chlorinations of alkylaromatic compounds, such as toluene, the xylenes, mesitylene etc., give the corresponding side‐chain polychloro‐derivatives, though some nuclear chlorination, and also the formation of viscous condensation products, may occur concomitantly. Replacement by chlorine of the side‐chain hydrogen of alkylperchlorobenzenes does not, in general, appear to proceed to completion. Attempts to obtain perchloro‐compounds by further chlorination in ultraviolet light cause fission of dichloromethyl groups and the formation of hexachlorobenzene.

show abstract

Studies on the nuclear chlorination of aromatic compounds

et al. 1954

View full text Add to dashboard Cite

The direct chlorination of aromatic hydrocarbons, in the presence of a ferric chloride‐iron catalyst, proceeds smoothly to give nuclear‐chlorinated derivatives. Methyl side‐chains are retained, but larger alkyl groups, such as ethyl, isopropyl and n‐butyl, readily undergo cleavage by chlorinolysis. Halogenated alkyl side‐chains, such as CCI3 and C2Cl5, are usually not removed, though complete chlorination of the nuclei of compounds containing them cannot normally be achieved. In certain cases, one chlorine atom of a nuclear polychloro‐compound is susceptible to attack by alcoholic alkali.

show abstract

Preparation of Chlorofluoro Derivatives of Ethylbenzene

Cited by 6 publications

References 1 publication

Aromatic and Alkaromatic Chlorocarbons

Aromatic and Alkaromatic Chlorocarbons

Studies on the chlorination of the side chains of alkylaromatic compounds

Studies on the nuclear chlorination of aromatic compounds

Contact Info

Product

Resources

About