General Description
White powder with a weak chlorine odor. Conflagrates at 414°F (turns brown). Chlorine gas evolves > 410°F.
Reactivity Profile
1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) reacts violently with xylene. 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) is incompatible with strong acids, easily oxidized materials, ammonia salts and sulfides. 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) will react with water or steam to produce toxic and corrosive fumes. At a pH of 9, 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) decomposes completely.
Air & Water Reactions
Sensitive to exposure to light, air, and moisture. Reacts with water or steam to produce toxic and corrosive fumes.
Potential Exposure
It is used as a chlorinating agent,
disinfectant, biocide, and laundry bleach. It is also used as
a polymerization catalyst in making vinyl chloride; and
in drug and pesticide synthesis.
Fire Hazard
Flash point data for this chemical are not available. 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN is probably combustible.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy.
Shipping
UN1479 Oxidizing solid, n.o.s., Hazard Class:
5.1; Labels: 5.1-Oxidizer, Technical Name Required
Incompatibilities
A strong oxidizer. Contact with water
forms poisonous and corrosive gases. Mixtures with xylene
may explode. Not compatible with moisture (especially hot
water, steam), strong acids; easily oxidized materials (such
as ammonia salts; sulfides, etc.); reducing agents; strong
bases; ammonium salts; sulfides. Compounds of the
carboxyl group react with all bases, both inorganic and
organic (i.e., amines) releasing substantial heat, water and
a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds,
dithiocarbamates, isocyanates, mercaptans, nitrides, and
sulfides (releasing heat, toxic and possibly flammable
gases), thiosulfates and dithionites (releasing hydrogen
sulfate and oxides of sulfur)
Description
DCDMH is a combustible, white powder witha chlorine-like odor. Molecular weight=197.03; Freezing/Melting point=130℃; Flash point=175℃. HazardIdentification (based on NFPA-704 M Rating System):Health 3, Flammability 1, Reactivity 0 Oxidizer, . Waterreactive; slightly soluble; solubility=0.2%.
Chemical Properties
DCDMH is a combustible, white powder.
Chlorine-like odor.
Waste Disposal
Incineration (815.5C/816C,
0.5 second for primary combustion; 104.4C/220F, 1.0 second for secondary combustion). The formation of elemental
chlorine can be prevented by injection of steam or methane
into the combustion process. Any nitrogen oxides may be
abated by the use of thermal or catalytic devices
Physical properties
White powder or four-sided crystals from chloroform with a chlorine-like odor. Aqueous solutions
are acidic.
Uses
Chlorinating agent; disinfectant;
laundry bleach; in water treatment; intermediate
for drugs; insecticides; polymerization
catalyst
Uses
Dantoin(R) DCDMH is an industrial bleaching agent based on dimethyl hydantoin. This product finds application wherever solid bleach is desired.
Uses
Dantoin(R) DCDMH LD (low dust) is an industrial bleaching agent based on dimethyl hydantoin. This product finds application wherever solid bleach is desired.
Health Hazard
1,3-Dichloro-5,5-dimethylhydantoin
powder in contact with water yields
hypochlorous acid, which is an irritant of the
eyes and mucous membranes.
Synthesis
General procedure for the synthesis of 1,3-dichloro-5,5-dimethylimidazoline-2,4-dione from 5,5-dimethylhydantoin: Preparation of ethyl acetate, tetrahydrofuran and liquid chlorine in the ratio of 1:1:0.7 by volume, as well as 5,5-dimethylglycolide urea, anhydrous sodium carbonate and lanthanum-modified nanoscale Ga/Al composite solid bases in the ratio of 1:1.2:0.15 by mass. The specific dosage was as follows 30 mL of ethyl acetate, 30 mL of tetrahydrofuran, 21 mL of liquid chlorine, 7 g of 5,5-dimethylglycolide, 8.4 g of anhydrous sodium carbonate and 1.05 g of lanthanum-modified nanoscale Ga/Al composite solid base. (1) 7 g of 5,5-dimethylglycolide urea and 8.4 g of anhydrous sodium carbonate were added to a reaction vessel equipped with a spherical condenser tube, magnetically stirred, and reacted for 6 h at room temperature; (2) 1.05 g of lanthanum-modified nanoscale Ga/Al composite solid bases, 30 mL of ethyl acetate, and 30 mL of tetrahydrofuran were added sequentially to the mixture of step (1). Then 21 mL of liquid chlorine was added dropwise at a rate of 60 drops per minute, magnetic stirring was turned on, and the reaction was heated at 100 °C for 2 h. (3) The heated mixture from step (2) was transferred to a microwave reactor for 5 h. The mixture was then heated for 2 h. The mixture was then heated for 2 h. The reaction was then transferred to a microwave reactor for 5 h. After the reaction was completed, the mixture was cooled, filtration was performed, and the filter cake was washed with tetrahydrofuran. The filtrate was rotary evaporated to recover part of ethyl acetate, tetrahydrofuran and lanthanum-modified nanoscale Ga/Al composite solid bases; (4) the residual filtrate from step (3) was poured into pure water under continuous stirring to precipitate the product sufficiently, and pumped and filtered to obtain the crude product. The crude product was successively recrystallized with ethanol and pure water, and then recrystallized with toluene for the second time, and the target product 1,3-dichloro-5,5-dimethylimidazoline-2,4-dione was finally obtained.
Environmental Fate
Chemical/Physical. Reacts with water (pH 7.0) releasing hypochlorous acid. At pH 9, nitrogen
chloride is formed (Windholz et al., 1983).
storage
(1) Color Code—Yellow: Reactive Hazard; Storein a location separate from other materials, especially flammables and combustibles. (2) Color Code—White:Corrosive or Contact Hazard; Store separately in a corrosion-resistant location. Prior to working with this chemicalyou should be trained on its proper handling and storage.1,3-Dichloro-5,5-dimethyl-hydantoin must be stored toavoid contact with strong acids (such as sulfuric acid, nitricacid, or hydrochloric acid) and easily oxidized materials(such as ammonium salts and sulfides) since violent reactions occur and poisonous gases can be produced. Store intightly closed containers in a cool, well-ventilated area awayfrom water or steam. 1,3-Dichloro-5,5-dimethyl-hydantoindecomposes with formation of poisonous gases at201-210℃. If 1,3-dichloro-5,5-dimethyl-hydantoin contacts water or steam, it decomposes at lower temperaturesand produces poisonous gases, including chlorine. Sourcesof ignition, such as smoking and open flames, are prohibitedwhere 1,3-dichloro-5,5-dimethyl-hydantoin is used, handled,or stored in a manner that could create a potential fire orexplosion hazard.
Purification Methods
Purify it by dissolving in conc H2SO4 and diluting with ice H2O, collect the solid, dry it in a vacuum and recrystallise it from CHCl3. It sublimes at 100o in a vacuum. It exhibits time-dependent hydrolysis at pH 9. [Petterson & Grzeskowiak J Org Chem 24 1414 1959, Beilstein 24 III/IV 1100.]
Toxics Screening Level
The initial threshold screening level (ITSL) for the following bromo- and chloro dimethylhydantoins is 2 μg/m3, based on an 8-hour averaging time.
References
[1] Patent: CN108484506, 2018, A. Location in patent: Paragraph 0016; 0018-0036
[2] Tetrahedron Letters, 2009, vol. 50, # 6, p. 656 - 658
[3] Journal fuer Praktische Chemie (Leipzig), 1926, vol. <2>113, p. 263 Anm.4