DUPONT DMT REACTION SOLVENT NEWS DMF»S03 complex is a unique agent for sulfating and amide preparation DMF«S03 sulfation agents are an ideal source of S0 3 for various reactions • • • •
Stable in storage Easily prepared Easily controlled in reactions Titratable to determine SO3 content
High substitution of polysaccharides without degradation The disadvantages of c o m m o n methods of m a k i n g c e l l u lose sulfates have been o v e r c o m e by using D M F » S 0 3 c o m plex. S u l f a t i o n of cellulose at low t e m p e r a t u r e w i t h high degree of s u b s t i t u t i o n was achieved t h r o u g h the use of D M F - S 0 3 comp\ex(Chemistry and Industry, 5 / 2 8 / 6 6 , 900). Degrees of s u b s t i t u t i o n of 2.6 to 2.7 were achieved on w o o d , cellulose and c o t t o n linters by sulfating w i t h DMF •SOa c o m p l e x at 5°C for three hours. Preparation of polypeptides with D M F - S 0 3 The use of DMF and DMF*S03 overcomes many difficulties usually associated w i t h polypeptide syntheses. Mixed anhydrides c o n t a i n i n g the COOSO3 g r o u p were prepared using D M F - S 0 3 c o m p l e x . It was reported (U.S. patent 2,766,225) that high yields were o b t a i n e d f r o m m o n o a m i n o acids. R
- CH-C 1 NH I C= 0
+
NHt-R"-C00H
R » protecting group R"= polypeptide
DMF-SO, DMF '
R-CH-C I OSO.-K* NH I
c=o
I R1
DMF is the least expensive of the " s u p e r " (highly dipolar aprotic) solvents—it recently was reduced to 22^ per lb. for bulk quantities. In a d d i t i o n , easy recovery, high c o n versions and faster reaction rates result in low use-costs. Versatility in chemical processes DMF is used in the m a n u f a c t u r e of a w i d e range of p r o d ucts, involving many classes of organic reactions, often w i t h existing e q u i p m e n t . Efficiency through high yields and pure products Higher conversions and faster reaction rates are often possible w i t h DMF, resulting in higher p r o d u c t yields. P r o d u c t purity results f r o m reduced b y - p r o d u c t c o n t a m - . ination. Easy recovery DMF can easily be recovered by simple distillation at a t m o s p h e r i c or reduced pressure. High recoveries (up to 99%) not only reduce p r o d u c t i o n costs, but also i m p r o v e p o l l u t i o n c o n t r o l . Du Pont's new DMF Recovery and P u r i f i c a t i o n Bulletin provides basic data on methods and e q u i p m e n t for recovery of DMF in p r o d u c t i o n operations.
DMF
Du Pont Company Room 5977 Wilmington, Delaware 19898 Please send • DMF Bulletin • DMF Recovery and Purification Bulletin NameTitleCompany-
COOLi+
N
Economy in production-scale use
Mail the c o u p o n for m o r e i n f o r m a t i o n o n Du Pont DMF.
0 II J* R-CH-C-N-R"-C-OH I NH I C= 0 I R'
Ergine synthesis Certain heterocyclic carboxylic acids are difficult to c o n vert to amides. Amides of ergot alkaloid derivatives were prepared in g o o d yields t h r o u g h the use of D M F * S 0 3 c o m plex. Diamides were prepared by reacting lysergic acid w i t h l i t h i u m h y d r o x i d e hydrate in m e t h a n o l , r e m o v i n g the solvent, redissolving in DMF, c h i l l i n g , and reacting w i t h t h e DMF-SCb c o m p l e x , f o l l o w e d by reaction w i t h a desired a m i n e [J. Org. Chem., 24, 368 (1959)].
LiOH • HtO MeOH
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DMF • S O j .
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_State_
CH,
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-Telephone-
fflTPnR5> D M F HAFN
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