Trichloroisocyanuric acid

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Trichloroisocyanuric acid
TCCA-0.png
TCCA.png
Names
IUPAC name
1,3,5-Trichloro-1,3,5-triazinane-2,4,6-trione
Other names
1,3,5-Trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
Chloreal
Isocyanuric chloride
Symclosene
TCCA
TCICA
Trichlor
Trichloro-s-triazinetrione
Properties
C3Cl3N3O3
Molar mass 232.40 g/mol
Appearance Colorless solid
Odor Chlorine-like
Density 2.19 g/cm3
Melting point 246.7 °C (476.1 °F; 519.8 K) (decomposes)
Boiling point Decomposes
1.27 g/100 ml (25 °C)
Solubility Reacts with ammonia
Soluble in acetone, acetonitrile, chlorocarbons
Solubility in acetone 30 g/100 g (30 °C)
Vapor pressure 1.6·10-8 mmHg (25 °C)
Acidity (pKa) 4.4
Hazards
Safety data sheet Sigma-Aldrich
Flash point Non-flammable
Related compounds
Related compounds
Cyanuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trichloroisocyanuric acid (abbreviated TCCA) is a useful chlorinating agent and is commonly used to produce chlorine gas.

Properties

Chemical

TCCA is basically insoluble in water. On addition to hydrochloric acid, it looses chlorine to become cyanuric acid.

C3Cl3N3O3 + 3 HCl → C3H3N3O3 + 3/2 Cl2

Reaction with ammonia produces chloroamines.

Producing chlorine

The reaction between it and hydrochloric acid is favorable for a few reasons.

1) For a given amount of TCCA, it produces a lot of chlorine, more so than other methods.

2) The reaction is slow and steady, not releasing all its chlorine at once in a violent and foaming reaction as is often the case with calcium hypochlorite. A more violent reaction is also more likely to bring over water vapor and HCl fumes, as well as creating an inhalation hazard, which is generally unfavorable.

3) The solid comes in easy to handle blocks that can be broken down to suitable sized chunks or a powder.

4) All the reactants and products are easy to clean from glassware, unlike manganese dioxide.

5) TCCA is usually cheap, especially when bought in bulk, so the cost per amount of chlorine produced is very low.

Physical

A white solid that has an odor similar to chlorine itself, it is often sold in big white circular 'tablets'.

Availability

It is available in a quite pure form in many countries as a slow chlorinating agents for swimming pools, though it's more often encountered as its sodium salt. It can be purchased online too, where it is usually quite cheap.

Preparation

TCCA can not be made easily, nor is it often desired to be due to its wide availability and alternatives if it can not be found. It can be made by clorinating cyanuric acid.

Projects

  • Producing chlorine gas
  • Make cyanuric acid
  • Copper cyanurate
    Complex between copper and Na-DCCA
  • Making singlet oxygen

Handling

Safety

Gloves should be worn when dealing with TCCA and care should be taken to avoid breathing in any dust. TCCA spontaneously produces large volumes of toxic chlorine in many reactions, so safety plans that dramatically reduce the chlorine's danger to you should in place when dealing with this chemical.

Storage

TCCA is best stores in closed plastic containers, in dark, well ventilated areas. Keep it away from any flammable materials, bases, acids. Since it gives off chlorine over time, keep it in a separate place from other reagent.

Disposal

Can be neutralized with an aqueous solution of sodium thiosulfate/sulfite/bisulfite/metabisulfite.

References

Tdep.

Relevant Sciencemadness threads