1,3,5-trioxane

1,3,5-trioxane Basic information
Product Name:1,3,5-trioxane
Synonyms:1,3,5-Trioxan;1,3,5-TRIOXACYCLOHEXANE;1,3,5-TRIOXANE;TRIOXYMETHYLENE;TRIFORMOL;1,3,5-trioxane (sym.);Formaldehyde trimer~s-Trioxan;METAFORMALDEHYDE
CAS:110-88-3
MF:C3H6O3
MW:90.08
EINECS:203-812-5
Product Categories:Acetals/Ketals/Ortho Esters;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
Mol File:110-88-3.mol
1,3,5-trioxane Structure
1,3,5-trioxane Chemical Properties
Melting point 59-62 °C(lit.)
Boiling point 112-115 °C
density 1.17
vapor pressure 7.5 hPa (20 °C)
refractive index 1.4168 (estimate)
Fp 113 °F
storage temp. Store below +30°C.
solubility 221g/l
form Crystals or Crystalline Flakes
color Colorless to white
explosive limit3.6-28.7%(V)
Water Solubility 221 g/L (25 ºC)
Sublimation 115 ºC
Merck 14,9734
BRN 102769
InChIKeyBGJSXRVXTHVRSN-UHFFFAOYSA-N
CAS DataBase Reference110-88-3(CAS DataBase Reference)
NIST Chemistry Reference1,3,5-Trioxane(110-88-3)
EPA Substance Registry System1,3,5-Trioxane (110-88-3)
Safety Information
Hazard Codes F,Xn
Risk Statements 11-37-63
Safety Statements 36/37-46
RIDADR UN 1325 4.1/PG 2
WGK Germany 1
RTECS YK0350000
Autoignition Temperature777 °F
TSCA Yes
HS Code 2912 50 00
HazardClass 4.1
PackingGroup III
Hazardous Substances Data110-88-3(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 8190 mg/kg LD50 dermal Rabbit > 3980 mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
1,3,5-trioxane Usage And Synthesis
Chemical PropertiesTrioxane is a most unusual chemical. It is an excellent solvent for many classes of materials. Concentrated aqueous solutions of trioxane have solvent properties which are not possessed by trioxane itself. Molten trioxane dissolves numerous organic compounds, such as naphthalene, urea, camphor, dichlorobenzene, etc. It is stable in alkaline or neutral solutions, yet it is depolymerized to formaldehyde by small amounts of strong acid or acid-forming materials, and the rate of depolymerization can be readily controlled.
Chemical PropertiesParaformaldehyde is a white crystalline solid. Irritating odor. The term “trioxane” applies specifically to this trimer (CH2O)3 but paraformaldehyde is applied both to trioxane and other low polymers or oligomers of formaldehyde.
Uses1,3,5-Trioxane is widely used as a source of anhydrous formaldehyde.
It can be used to synthesize:
  • Polyoxymethylene and hyperbranched polyesters.
  • Calixarenes such as calix[4]resorcinarene, calix[6]resorcinarene and para-tert-butylcalix[8] and [9]arene.
  • Various natural products including (?)-motuporin, (+)-sundiversifolide, (+)-lyconadin A and (?)-lyconadin B.

Uses1,3,5-Trioxane is used in organic chemical processes such as aldol condensation of amides and syntheses of chloromethyl esters or other plastics.
DefinitionChEBI: A saturated organic heteromonocyclic parent that is cyclohexane in which the carbon atoms at positions 1, 3 and 5 are replaced by oxygen atoms.
General DescriptionTransparent crystals or white crystalline solid with a pleasant odor resembling the odor of chloroform. Melts at 62°C; boils at 115°C without polymerization. The cyclic trimer of formaldehyde.
Air & Water ReactionsHighly flammable. Water soluble.
Reactivity Profiles-Trioxane is stable under normal laboratory conditions but is unstable in the presence of acids, which initiate polymerization. Sublimes readily. May react with oxidizing matter . A stable polymeric product of formaldehyde that in the presence of strong aqueous acids will depolymerize (reforming the parent formaldehyde). Inert to strong alkalis. Readily converted in non aqueous solutions to the monomeric formaldehyde by small concentrations of acid---the rate of conversion is directly proportional to the concentration of the acid.
Health HazardACUTE/CHRONIC HAZARDS: s-Trioxane is toxic and flammable. It can emit toxic fumes on contact with acid or acid fumes.
Fire Hazards-Trioxane is combustible.
Safety ProfileMutation data reported. Can evolve toxic formaldehyde fumes when heated strongly or in contact with strong acids or acid fumes. Flammable liquid when exposed to heat, flame, or oxidzers. May explode when heated. Explosive in the form of vapor when exposed to heat or flame. Explodes on impact, possibly due to peroxide contamination. Mixtures with hydrogen peroxide are explosives sensitive to heat, shock, or contact with lead. Mixtures with liquid oxygen are highly explosive. Incompatible with oxidizing materials. To fight fire, use foam, CO2, or dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also FORMALDEHYDE.
Potential ExposureParaformaldehyde is used in polyacetal resin manufacture; as a food additive; and as an odorless fuel.
ShippingUN2213 Paraformaldehyde, Hazard Class: 4.1; Labels: 4.1-Flammable solid.
Purification MethodsCrystallise 1,3,4-trioxane from sodium-dried diethyl ether or water, and dry it over CaCl2. It can also be purified by zone refining. [Beilstein 19 H 381, 19 II 392, 19 III/IV 4710, 19/9 V 103.]
IncompatibilitiesParaformaldehyde dust forms an explosive mixture with air. Decomposes on contact with oxidizers, strong acids; acid fumes; and bases; with elevated temperatures, forming formaldehyde. May explode when heated. May explode on impact if peroxide contamination develops. Mixtures with hydrogen peroxide or liquid oxygen are explosives sensitive to heat, shock, or contact with lead.
Waste DisposalDissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
PARA-PROPIONALDEHYDE 2,4,6-TRIS(CHLOROMETHYL)-1,3,5-TRIOXANE 2,4,6-TRIS(1-BROMO-1-METHYLETHYL)-1,3,5-TRIOXANE 2,4,6-triisobutyl-1,3,5-trioxane 4,6-DIMETHYL-2-ETHYL-1,3,5-TRIOXANE 2,4,6-TRIMETHYL-1,3,5-TRIOXANE n-Tridecane Diantimony trioxide Cyclohexane 2,4-DIETHYL-6-METHYL-1,3,5-TRIOXANE Triallylamine 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE Paraformaldehyde 1,3,5-trioxane 4,4',4''-(1,3,5-TRIOXANE-2,4,6-TRIYL)TRIBUTANOIC ACID Tridecanoic acid isotridecan-1-ol Aluminum oxide

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