628-55-7Relevant articles and documents
Characterization by NMR of reactants and products of hydrofluoroether isomers, CF3(CF2)3OCH3 and (CF 3)2C(F)CF2OCH3, reacting with isopropyl alcohol
Knachel, Howard C.,Benin, Vladimir,Moddeman, William E.,Birkbeck, Janine C.,Kestner, Thomas A.,Young, Tanya L.
, p. 407 - 413 (2013)
The 3M Company product Novec 71IPA DL, a mixture of methoxyperfluorobutane, methoxyperfluoroisobutane and 4.5 wt.% isopropyl alcohol, has been found to be very stable at ambient temperature, producing fluoride at the rate of ~1 ppm/year. Our earlier kinetic and theoretical studies have identified the reaction mechanism. This paper identifies the 1H and 19F NMR chemical shifts, multiplicities, and coupling constants of reactants and the major products that result from aging the mixture in sealed Pyrex NMR tubes for periods up to 1.8 years at temperatures from 26 °C to 102 °C. Chemical shifts and coupling constants of fluorine and hydrogen atoms on the hydrofluoroethers and isopropyl alcohol are traced through the reactions to their values in the products - esters, isopropylmethyl ether, and HF. These spectral positions, multiplicities, and coupling constants are presented in table format and as figures to clarify the transformations observed as the samples age. Copyright 2013 John Wiley & Sons, Ltd. The titled hydrofluoroether isomers react slowly with isopropyl alcohol in a two-step process yielding isopropylmethyl ether, the corresponding isopropyl ester isomers, and HF. 19F and 1H NMR chemical shifts, multiplicities, and coupling constants are assigned to the reactants and major products in this paper. Copyright
Antimony(v) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes
Arias Ugarte, Renzo,Devarajan, Deepa,Mushinski, Ryan M.,Hudnall, Todd W.
supporting information, p. 11150 - 11161 (2016/07/20)
1-Diphenylphosphinonaphthyl-8-triphenylstibonium triflate ([2][OTf]) was prepared in excellent yield by treating 1-lithio-8-diphenylphosphinonaphthalene with dibromotriphenylstiborane followed by halide abstraction with AgOTf. This antimony(v) cation was found to be stable toward oxygen and water, and exhibited exceptional Lewis acidity. The Lewis acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf] catalyzed the cyclotrimerization of aliphatic and aromatic aldehydes to afford the industrially-useful 1,3,5 trioxanes (N) in good yields, and with great selectivity. This phosphine-stibonium motif represents one of the first catalytic systems of its kind that is able to catalyze these reactions with aldehydes in a controlled, efficient manner. The mechanism of these processes has been explored both experimentally and theoretically. In all cases the Lewis acidic nature of the antimony(v) cation was found to promote these reactions.
Process for making dibutyl ethers from aqueous isobutanol
-
Page/Page column 7-8, (2008/06/13)
The present invention relates to a catalytic process for making dibutyl ethers using a reactant comprising isobutanol and water. The dibutyl ethers so produced are useful in transportation fuels.