STUDIES IN ISO-UREAS AND ISO-UREIDES: I. SOME NEW ISO-UREAS; SALTS AND ACYL DERIVATIVES

1929 ◽  
Vol 1 (3) ◽  
pp. 261-272 ◽  
Author(s):  
Steward Basterfield ◽  
Edward C. Powell

In this investigation a series of new iso-urea ethers has been prepared by the general reaction of addition of alcohols to cyanamide in the presence of dry hydrogen chloride. Where the hydrochlorides of the iso-ureas were difficult to isolate and purify, conversion to the salicylates gave excellent results. The new iso-ureas were further characterized by condensing them with methyl malonate to form iso-urea salts of 2-alkoxy-barbituric acids, from which the acids themselves could be easily liberated by the addition of dilute mineral acid. A few open-chain acyl derivatives were also prepared.

2016 ◽  
Vol 2016 ◽  
pp. 1-12 ◽  
Author(s):  
Rogers E. Harry-O’kuru ◽  
Girma Biresaw ◽  
Brent Tisserat ◽  
Roque Evangelista

In a previous study of the characteristics of acyl derivatives of polyhydroxy milkweed oil (PHMWO), it was observed that the densities and viscosities of the respective derivatives decreased with increased chain length of the substituent acyl group. Thus from the polyhydroxy starting material, attenuation in viscosity of the derivatives relative to PHMWO was found in the order: PHMWO ≫ PAcMWE ≫ PBuMWE ≫ PPMWE (2332 : 1733 : 926.2 : 489.4 cSt, resp., at 40°C), where PAcMWE, PBuMWE, and PPMWE were the polyacetyl, polybutyroyl, and polypentanoyl ester derivatives, respectively. In an analogous manner, the densities also decreased as the chain length increased although not as precipitously compared to the viscosity drop. By inference, derivatives of vegetable oils with short chain length substituents on the triglyceride would be attractive in lubricant applications in view of their higher densities and possibly higher viscosity indices. Pursuant to this, we have explored the syntheses of formyl esters of three vegetable oils in order to examine the optimal density, viscosity, and related physical characteristics in relation to their suitability as lubricant candidates. In the absence of ready availability of formic anhydride, we opted to employ the epoxidized vegetable oils as substrates for formyl ester generation using glacial formic acid. The epoxy ring-opening process was smooth but was apparently followed by a simultaneous condensation reaction of the putativeα-hydroxy formyl intermediate to yield vicinal diformyl esters from the oxirane. All three polyformyl esters milkweed, soy, and pennycress derivatives exhibited low coefficient of friction and a correspondingly much lower wear scar in the 4-ball antiwear test compared to the longer chain acyl analogues earlier studied.


Author(s):  
V. A. Haidukevich ◽  
S. K. Petkevich ◽  
E. G. Karankevich ◽  
P. V. Kurman ◽  
Z. I. Kuvaeva ◽  
...  

Tert-butyloxycarbonylprolylleucylglycinamide is obtained both by the interaction of tert-butyloxycarbonylprol ylleucylglycine ethyl ester with a methanolic ammonia solution and by the reaction of glycine amide with a mixed anhydride which was synthesized from tert-butyloxycarbonylprolylleucine and isobutylchloroformate. The removal of the tert-butyloxycarbonyl group by the action of formic acid or a dioxane solution of hydrogen chloride and treatment of the resulting salts with the corresponding base yielded a prolylleucylglycinamide, by the interaction of which with acetic, benzoic or 5-phenylisoxazole-3-carboxylic acids chlorides acyl derivatives of prolylleucylglycinamide are obtained.


Author(s):  
Ya. G. Avdeev ◽  
◽  
D.S. Kuznetsov ◽  
Yu.I. Kuznetsov ◽  
◽  
...  

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