WIP(Q)if WWW m3M®fS®l ^©ILWlif W DMF'SOs complex is a unique agent for sulfating and amide preparation DMF«S03 sulfation agents are an ideal source of S0 3 for various reactions • • • •
Discover the opportunities for improving products and processes with Du Pont DMF
Stable in storage Easily prepared Easily controlled in reactions Titratable to determine SO3 content
High substitution of polysaccharides without degradation The disadvantages of common methods of making cellulose sulfates have been overcome by using DMF*S0 3 complex. Sulfation of cellulose at low temperature with high degree of substitution was achieved through the use of DMF«S03 complex (Chemistry and Industry, 5/28/66, 900). Degrees of substitution of 2.6 to 2.7 were achieved on wood, cellulose and cotton linters by sulfating with DMF-SOs complex at 5°C for three hours. Preparation of polypeptides with DMF*S03 The use of DMF and DMF-S03 overcomes many difficulties usually associated with polypeptide syntheses. Mixed anhydrides containing the COOSO3 group were prepared using DMF«S0 3 complex. It was reported (U.S. patent 2,766,225) that high yields were obtained from monoamino acids. -CH-C-OV 1 NH I
DMF-SO, DMF '
- CH - C I 0S0"K* NH I C-0 I R'
c=o
I R'
+ NHt-R"-C00H
Economy in production-scale use DMF is the least expensive of the "super" (highly dipolar aprotic) solvents-25# per lb. for bulk quantities. In addition, easy recovery, high conversions and faster reaction, rates result in low use-costs. Versatility in chemical processes DMF is used in the manufacture of a wide range of products, involving many classes of organic reactions, often with existing equipment. Efficiency through high yields and pure products Higher conversions and faster reaction rates are often possible with DMF, resulting in higher product yields. Product purity results from reduced by-product contamination. Easy recovery DMF can easily be recovered by simple distillation at atmospheric or reduced pressure. High recoveries (up to 99%) not only reduce production costs, but also improve pollution control. Du Pont's new DMF Recovery and Purification Bulletin provides basic data on methods and equipment for recovery of DMF in production operations. Mail the coupon for more information on Du Pont DMF.
0 II J) R-CH-C-N-R"-C-0H
DMF
NH R* = protecting group RN= polypeptide
C= 0 I R'
Ergine synthesis Certain heterocyclic carboxylic acids are difficult to convert to amides. Amides of ergot alkaloid derivatives were prepared in good yields through the use of DMF*S0 3 complex. Diamides were prepared by reacting lysergic acid with lithium hydroxide hydrate in methanol, removing the solvent, redissolving in DMF, chilling, and reacting with the DMF-S03 complex, followed by reaction with a desired amine [J. Org. Chem., 24, 368 (1959)].
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Please send • DMF Bulletin • DMF Recovery and Purification Bulletin
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