Tertiary acetylenic glycols

NON-IONIC SURFACTANTS Polyoxyethylenated alkylphenols, alkylphenol ethoxylates Polyoxyethylenated straight- chain alcohols, alcohol ethoxylates Polyoxyethylenated polyoxypropylene glycols Polyoxyethylenated mercaptans Long-chain carboxylic acid esters Alkanolamine condensates, alkanolamides Tertiary acetylenic glycols Polyoxyethylenated silicones N-alkylpyrrolidones Alkylpolyglycosides... 

Oxidation of secondary-tertiary acetylenic glycols (128) provides a route to furanones (129). ... 

Table 5. Commercial Secondary and Tertiary Acetylenic Alcohols and Glycols...

Economic Aspects. A number of secondary and tertiary acetylenic alcohols and glycols are manufactured by Air Products and Chemicals Co. In 1990, U.S. bulk prices of ethyloctynol, methylbutynol, and tetramethyldecynediol were about 8.35/kg, 3.95/kg, and 8.00/kg, respectively. 

This reaction was initially reported by Favorskii in 1905 and subsequently extended by Babayan in 1939. It is a base-promoted or -catalyzed ethynylation of aldehydes and ketones to produce secondary or tertiary acetylenic alcohols or glycols using anhydrous KOH or NaOH. Therefore, it is generally known as the Favorskii-Babayan reaction or Favorskii reaction. Although it has been proposed that this reaction might involve a reaction between acetylene and the adduct from the ketone and KOH or a coupling of potassium acetylide with the carbonyl compounds, the most recent experimental results indicate that potassium hydroxide and acetylene first form a complex, rather than potassium acetylide in liquid ammonia, which then reacts with carbonyl compounds to form the acetylenic alcohols, where ammonia functions as a co-catalyst. The experimental evidence includes... 

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