Chemical Properties
Pale yellowish oily liquid. Slightly soluble in water, soluble in alcohol and oils.
Occurrence
Reported found in beef (boiled, cooked) and coffee
Uses
Furfuryl disulfide has been used in the preparation of poly(disulfido-imide)s by Diels-Alder (DA) reaction with the various bismaleimides.
Definition
ChEBI: Bis(2-furanylmethyl) disulfide is a heteroarene.
Preparation
Difurfuryl disulfide is produced from Furfural and Hydrogen sulfide gas.
Taste threshold values
Taste characteristics at 20 ppm: roasted, sulfuraceous, alliaceous, green and meaty.
General Description
Difurfuryl disulfide is a sulfur-containing volatile compound mainly found in roasted coffee. It is also the main degradation product of furfuryl mercaptan under Fenton-type reaction conditions.
Synthesis
The general procedure for the synthesis of difurfuryldisulfide from furfuryl(base)thiols was as follows: a non-homogeneous mixture of 4-chlorobenzenethiol (0.145 g, 1 mmol) with KBrO3 (0.167 g, 1 mmol), (NH4)6Mo7O24-4H2O (0.124 g, 10 mmol), and CH3CN/H2O (7:3, 5 mL) was mixed. The reaction mixture was stirred in a fume hood for 4 min under ambient atmosphere and at room temperature. The reaction progress was monitored by thin layer chromatography (TLC) using EtOAc/n-C6H14 (1:13) as eluent. Upon completion of the reaction, CH2Cl2 (20 mL) was added and the reaction mixture was filtered. The filtrate was washed sequentially with 5% NaOH solution and water and then dried with anhydrous MgSO4. Finally, the difurfuryldisulfide product of sufficient purity was obtained by evaporating the solvent.
References
[1] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 3, p. 685 - 691
[2] Synthesis, 2007, # 21, p. 3286 - 3289
[3] Journal of Chemical Research - Part S, 2002, # 11, p. 564 - 566
[4] Synthetic Communications, 2011, vol. 41, # 2, p. 170 - 176
[5] Journal of Organic Chemistry, 1995, vol. 60, # 11, p. 3266 - 3267
