Dithiocarbamate

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Chemical structure of dithiocarbamates

A dithiocarbamate is a functional group in organic chemistry. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms. Sodium diethyldithiocarbamate is a common example. Dithiocarbamates and their derivatives are widely used in the vulcanization of rubber.[1]

Formation and reactions[edit]

Many primary and secondary amines react with carbon disulfide and sodium hydroxide to form dithiocarbamate salts:[1]

R2NH + CS2 + NaOH → R2NCS2-Na+ + H2O

Ammonia reacts with CS2 similarly:

2 NH3 + CS2 → H2NCS2-NH4+

Dithiocarbamate salts are pale colored solid that are soluble in water and polar organic solvents.

Applications[edit]

Zinc dithiocarbamates are used to modify the crosslinking of certain polyolefins with sulfur, a process called vulcanization. They are used as ligands for chelating metals.[2]

Dithiocarbamates specifically ethylene bisdithiocarbamates, EBDCs, in the form of complexes with manganese (maneb), zinc (zineb) or a combination of manganese and zinc (mancozeb), have been used extensively as fungicides in agriculture from the 1940s.[3][4]

See also[edit]

References[edit]

  1. ^ a b Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a23_365.pub2
  2. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 0080379419. 
  3. ^ http://www.apsnet.org/publications/apsnetfeatures/Pages/Fungicides.aspx
  4. ^ Gullino, Maria Lodovica, et al. "Mancozeb: past, present, and future." Plant Disease 94.9 (2010): 1076-1087.