Sulfonation of Long Chain Alkene-2 and Vinylidenes in a Continuous Sulfonation Unit

升三, 永山; 勝美, 谷口; 誠, 青木

doi:10.1246/nikkashi1898.74.4_710

Cited by 6 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There is now a substantial body of evidence indicating that the initial reaction products from sulphonation of unbranched alkenes are the corresponding fisultones (1)(2)(3)(4)(5), as shown in Scheme i. In the sulphonation of unbranched alk-l-enes (referred to from here on as ~-olefins) the initially formed/%sultone decomposes rapidly to give a product mixture containing the corresponding ~/-sultone as a major component, together with the alk-2-ene-l-sulphonic acid (6).…”

mentioning

confidence: 99%

“…However, the initial formation of ~sultones, with retention of stereochemistry (2), has been established and it is known that stable sultones of the 7 and/or 5 type are formed subsequently (7). However, the initial formation of ~sultones, with retention of stereochemistry (2), has been established and it is known that stable sultones of the 7 and/or 5 type are formed subsequently (7).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Formation of sultones in olefin sulphonation

Roberts

Williams

1990

J Americ Oil Chem Soc

View full text Add to dashboard Cite

Sultones are formed in the sulphonation of unbranched ~ and internal olefins in the sequence /~ -~ ? -~ 5. In the case of ~-olefin sulphonation by sulphur trioxide in a short residence time (ca. 60 s) reactor, the t3 -~ ? sultone reaction has already gone to completion when the reaction mixture emerges from the reactor. Kinetic data are presented for the ? --, 5 terminal sultone isomerization. In the case of internal olefin sulphonation, formation of ? and 5 sultones has not proceeded to a significant extent when the reaction product emerges from the reactor. Kinetic data are presented for the /? -~ ~ internal sultone isomerization. Two internal ~f-sultones -cis and trans -are formed, but only one internal 5-sultone, the trans isomer. The internal y -~ internal 5 sultone isomerizations required forcing conditions (150 ~ C, 3 hr incomplete reactions) or prolonged aging (20-25~ 21 days; 5 sultone still the minor sultone). The cis internal ~ sultone is more resistant to isomerization than is its trans isomer. These reactivity differences are rationalized using arguments developed from that proposed by Bordwell, Osborne and Chapman in 1959 to interpret the effects of methyl substitution on rates of ?-sultone solvolysis.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%