Thiourea dioxide
Encyclopedia
Thiourea dioxide is an organosulfur compound that is used in the textile
industry. It functions as a reducing agent
. Thiourea dioxide is not a dioxide, but instead is a derivative of a sulfinic acid (RS(O)(OH), hence the alternative name formamidine sulfinic acid.
:
Aqueous hydrogen peroxide
is also an effective oxidant:2CS + 2H2O2 → (NH)(NH2)CSO2H + 2H2O
s in environmentally safer procedures. Thiourea dioxide has also been used for the reduction
of aromatic nitroaldehydes and nitroketones to nitroalcohols.
. The N2CS core is approximately planar but the CSO2H subunit is pyramidal. Selected bond length
s: S-C = 1.85, C-N = 1.31 , and S-O = 1.49 Å.
Textile
A textile or cloth is a flexible woven material consisting of a network of natural or artificial fibres often referred to as thread or yarn. Yarn is produced by spinning raw fibres of wool, flax, cotton, or other material to produce long strands...
industry. It functions as a reducing agent
Reducing agent
A reducing agent is the element or compound in a reduction-oxidation reaction that donates an electron to another species; however, since the reducer loses an electron we say it is "oxidized"...
. Thiourea dioxide is not a dioxide, but instead is a derivative of a sulfinic acid (RS(O)(OH), hence the alternative name formamidine sulfinic acid.
Synthesis
Thiourea dioxide is prepared by the oxidation of thiourea with chlorine dioxideChlorine dioxide
Chlorine dioxide is a chemical compound with the formula ClO2. This yellowish-green gas crystallizes as bright orange crystals at −59 °C. As one of several oxides of chlorine, it is a potent and useful oxidizing agent used in water treatment and in bleaching....
:
- 4 ClO2 + 5 (NH2)2CS + 2 H2O → 5 (NH)(NH2)CSO2H + 4 HCl
Aqueous hydrogen peroxide
Hydrogen peroxide
Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...
is also an effective oxidant:2CS + 2H2O2 → (NH)(NH2)CSO2H + 2H2O
Uses
Thiourea dioxide is used in reductive bleaching in textileTextile
A textile or cloth is a flexible woven material consisting of a network of natural or artificial fibres often referred to as thread or yarn. Yarn is produced by spinning raw fibres of wool, flax, cotton, or other material to produce long strands...
s in environmentally safer procedures. Thiourea dioxide has also been used for the reduction
Reduction
Reduction, reduced, or reduce may refer to:- Chemistry :* Reduction, part of a reduction-oxidation reaction where oxygen is being removed from a compound.** Reduced gas, a gas with a low oxidation number...
of aromatic nitroaldehydes and nitroketones to nitroalcohols.
Structure
The structure of thiourea dioxide is related to that for thioureaThiourea
Thiourea is an organosulfur compound of with the formula SC2 . It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom, but the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. "Thioureas" refers to a broad...
. The N2CS core is approximately planar but the CSO2H subunit is pyramidal. Selected bond length
Bond length
- Explanation :Bond length is related to bond order, when more electrons participate in bond formation the bond will get shorter. Bond length is also inversely related to bond strength and the bond dissociation energy, as a stronger bond will be shorter...
s: S-C = 1.85, C-N = 1.31 , and S-O = 1.49 Å.