3,3 -dithiodipropionic acid

Mercaptopropionic acid (HRSH) has been oxidised with ferricyanide in aqueous solution to give 3,3 -dithiodipropionic acid in 95 % yield. Whilst individual runs showed second-order disappearance of oxidant, the magnitude of 2 varied with increasing thiol, oxidant and ferrocyanide concentrations , viz. 

D. L. Trimm We have found no evidence of such attack on the alkyl and aryl disulfides produced in our study, even at a sodium hydroxide concentration of 5M. Such reactions would be expected to occur more easily, however, with substituted disulfides such as 3,3 -dithiodipropionic acid or 2,2 -dithiodiethylamine. 

Dithiodipropionic acid bis(M-hydroxysuccinimide ester) (DTSP, D3669) should be dissolved in dimethylsulfoxide (lOmg/mL), prepare freshly before use. 

Unsubstituted 10-, 11-, and 13-membered cyclic diazadisulfidcs were prepared in good yields by the reaction of ethylene- or trimethylenediamine with esters of dithiodiacetic acid or 3,3 -dithiodipropionic acid in the absence of a solvent (method Z-1) (Owen and Fayadh, 1970 Owen et al., 1973). No products were observed when substituted diamines were used. 

Dithia-I,8-octanedithiol, 474 Dithiasilolidine, 105 Dithiodiacetic acid, 476 3,3 -Dithiodipropionic acid, 476 iV,Af -Ditosylbis(2-aminoethyI)sulfide, 480 AiA -Ditosyl-l,4-butancdiamine, 62 A A -Ditosyldiaminodiols, 61, 62 A, iV -Ditosyl-l,5-diamino-3-oxapentane, 44 jV.jV -Ditosyl-1,11-diazacycloeicosane, 77 A, A -Ditosyl-4,9-diaza-l,12-dodecanediol, 62... 

In the lightening of petroleum hydrocarbon oil, esters of mercaptocarboxyhc acids can modify radical behavior during the distillation step (58). Thioesters of dialkanol and trialkanolamine have been found to be effective multihinctional antiwear additives for lubricants and fuels (59). Alkanolamine salts of dithiodipropionic acid [1119-62-6] are available as water-soluble extreme pressure additives in lubricants (60). 

Dithiodipropionic acid was without effect on the reaction rate but the reaction went faster at high pH, suggesting the participation of species HRS" (thiolate) and RS " (thiolate carboxylate). The retardation by ferrocyanide suggests the fol-... 

Addition to the disulfide function is also observed with OH (Bonifacic et al. 1975b). But here, in addition to the substitution reaction (45), generation of a disulfide radical cation and a hydroxide ion is also observed [reaction (46)]. The high solvation energy of the latter certainly provides additional driving force. There is EPR evidence that RSO- is also formed [reaction (47) Gilbert et al. 1975]. In dithiodipropionic acid and in cystine, the thiol is indeed a major product (30-40% Elliot et al. 1981). 

Pang, D., Z. Wang, and C.C. Zongli (1992). Electrocatalysis of metaUoporphyrins— Part 11 Catalytic electroreduction of dithiodipropionic acid with water-soluble cobalt tetrakis(4-trimethylammoniophenyl)porphyrin catalyst. Electrochim. Acta 37(14), 2591-2594. 

Dimethyidithiocarbamic acid, lead salt. See Lead dimethyidithiocarbamate Dimethyidithiocarbamic acid sodium salt. See Sodium dimethyidithiocarbamate Dimethyl dithiodipropionate Empirical C8H14O4S2 Formula (SCH2CH2COOCH3)2 Uses Reaction intermediate for fungicides, insecticides, thio compds., cyclic biocides ... 

Eval K102A, Eval L101A, Eval T102C. See Ethylene/vinyl acetate/vinyl alcohol copolymer Evanacid 3CS. See Carboxymethyl mercaptosuccinic acid Evangard 18MP. See Octadecyl 3-mercaptopropionate Evangard DTB. See Distearyl dithiodipropionate... 

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