Guanylureas

N,]Sf -DicHoiocaibodiimide is useful ia preparation of photothermographic materials (101). Chlorinated guanylurea (av CI2 85%), prepared from dicyanamide, is useful as a bleach for synthetic fabrics (102). Chlorazodin, dichloroa2odicarbonarnidine, NH2C(=NC1) N=NC(=NC1) NH2, [502-98-7]... 

Hydrolysis (47) of dicyandiamide occurs easily at elevated temperatures ia the presence of an equivalent of mineral acid to yield guanylurea salts. This reaction is quantitative and can be used for the determination of dicyandiamide (48). 

Specifications, Analysis, and Toxicity. Dicyandiamide is identified quaHtatively by paper chromatography and quantitatively by ultraviolet spectrometry of the chromatogram. More commonly, total nitrogen analysis is used as a purity control or the dicyandiamide is converted by hydrolysis to guanylurea, which is determined gravimetrically as the nickel salt (50). Methods based on the precipitation of silver dicyandiamide picrate are sometimes used (51). Dicyandiamide can also be titrated with tetrabutylammonium hydroxide ia pyridine solution. Table 4 gives a typical analysis of a commercial sample. Dicyandiamide is essentially nontoxic. It may, however, cause dermatitis. 

Complex compounds of biguanides and guanylureas with metallic elements. P. Ray, Chem. Rev., 1961,61,313-359(188). 

Monocyclic zwitterionic triheteraborines (44-47) were synthesized quite some time ago by treating biguanidine <62JA2529> or guanylurea or its O-alkyl ethers <72JINC3643> with trialkylborates. The borate esters 44a and 47a were easily hydrolyzed to the stable corresponding dihydroxy borate anion-based zwitterions 44b and 47b, respectively. 

Helf (Ref 6) investigated ten hew materials as flash smoke suppressants in proplnts. Guanylurea Nitrate was the most promising compd with regard to physical chemical props, stability, and 0 balance. Guanylnitro Urea was unsuitable for proplnts contg NG. Carbohydrazide-N-carboxyamide Carbohy-drazide-N,N -dicarboxyamide showed desirable promise but depended on a special starting material. Ammonium Nitrourea, Diammonium -methylene-bis-(nitrosohydroxylamine) ... 

St CA 54, 15934(1960) (Differential thermal analysis and thermo gravimetry of some salts of Gu and related compounds) (Compares thermal stability, decon temp and 5-kg impact sensitivity of Picrates and Styph-natesof Hydrazine, aminoguanidine, N-tnethyl-guantdine, guanylurea, N-ethylguanidine and Gu)... 

N 51.06%, OB —53.5% (to /4C12) crysts, mp 157° sol in w insol in organics explodes on heating. Prepd by treating l-amino-3-guanylurea dihydrochioride with N2Os in chlf. Its expl props were not investigated Refs 1) Beil 3, 130 2) J. Thiele E. 

Guanylurea. Dicyandiamidine or Carbamyl-guanidine and Derivatives. See Vol 5, p D1217-R... 

FB 0.0% (See under Pentafluoroguanidine) gas, bp ca —30°, dec at 208°. Prepd by fluori-nation of guanylurea sulfate (nitrogen dilution)... 

N-guanylurea dinitramide (commonly known as FOX-12) has low sensitivity and is an excellent candidate for insensitive munitions [72]. It is neither hygroscopic nor soluble in water. Its thermal stability is comparable to RDX and superior to that of ADN. The substitution of ammonium in dinitramide by an organic cation results in the change of combustion temperature and reactivity of the fuel. 

Table 13 Some Oxovanadium(IV) Biguanide, Guanylurea and Dibiguanide Complexes...

Ethylene sulfide has been employed as an intermediate in poly meric compositions from cryanamide,70 biguanide,78 and guanylurea,71 which are claimed to be UBeful aa insecticides, rubber addenda, and dehairing agents. 

In view of the presence of active functional groups at suitable sites in the above ligands and their substituted derivatives, these tend to form coordination compounds/chelates with a large number of metals. Excellent reviews have been published on the complex compounds of biguanides151152 and guanylureas, 51 and biuret.153,154... 

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