110-88-3 Usage
Description
1,3,5-Trioxane, also known as trioxane, is a transparent crystal or white crystalline solid with a pleasant odor resembling the odor of chloroform. It is the cyclic trimer of formaldehyde and is a saturated organic heteromonocyclic parent that is cyclohexane in which the carbon atoms at positions 1, 3, and 5 are replaced by oxygen atoms. Trioxane melts at 62°C and boils at 115°C without polymerization.
Uses
1. Used in Organic Chemical Processes:
1,3,5-Trioxane is used as a source of anhydrous formaldehyde in various organic chemical processes, such as aldol condensation of amides and syntheses of chloromethyl esters or other plastics.
2. Used in the Synthesis of Polymers and Natural Products:
1,3,5-Trioxane is used as a starting material for the synthesis of polyoxymethylene and hyperbranched polyesters. It is also used in the synthesis of calixarenes, such as calix[4]resorcinarene, calix[6]resorcinarene, and para-tert-butylcalix[8] and [9]arene. Additionally, it is used in the synthesis of various natural products, including (+)-motuporin, (+)-sundiversifolide, (+)-lyconadin A, and (+)-lyconadin B.
3. Used in the Production of Paraformaldehyde:
Paraformaldehyde is a white crystalline solid with an irritating odor. The term "trioxane" specifically applies to the trimer (CH2O)3, but paraformaldehyde is applied to both trioxane and other low polymers or oligomers of formaldehyde.
Chemical Properties:
Trioxane is an unusual chemical and an excellent solvent for many classes of materials. Concentrated aqueous solutions of trioxane have solvent properties that 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.
Air & Water Reactions
Highly flammable. Water soluble.
Reactivity Profile
s-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 Hazard
ACUTE/CHRONIC HAZARDS: s-Trioxane is toxic and flammable. It can emit toxic fumes on contact with acid or acid fumes.
Fire Hazard
s-Trioxane is combustible.
Safety Profile
Mutation 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 Exposure
Paraformaldehyde is used in polyacetal
resin manufacture; as a food additive; and as an
odorless fuel.
Shipping
UN2213 Paraformaldehyde, Hazard Class: 4.1;
Labels: 4.1-Flammable solid.
Purification Methods
Crystallise 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.]
Incompatibilities
Paraformaldehyde 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 Disposal
Dissolve 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.
Check Digit Verification of cas no
The CAS Registry Mumber 110-88-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 110-88:
(5*1)+(4*1)+(3*0)+(2*8)+(1*8)=33
33 % 10 = 3
So 110-88-3 is a valid CAS Registry Number.
InChI:InChI=1/C3H6O3/c1-2-4-6-5-3-1/h1-3H2
110-88-3Relevant articles and documents
The salt effect on the yields of trioxane in reaction solution and in distillate
Yin, Liuyi,Hu, Yufeng,Zhang, Xianming,Qi, Jianguang,Ma, Weiting
, p. 37697 - 37702 (2015)
Batch reaction experiments were performed to investigate the salt effect on the yield of trioxane in the reaction solution. The salts considered include NaHSO4, Na2SO4, NaH2PO4, Na2HPO4, KCl, NaCl, LiCl, ZnCl2, MgCl2, and FeCl3. The effects of the anionic structure and the cation charge density on the yield of trioxane in the reaction solution were elucidated and the mechanisms that govern such effects were established. It is shown that the first four salts exerted a negative effect on the yield of trioxane in the reaction solution and such an effect increased progressively from left to right. This trend is due to the formation of NaHSO4, H3PO4, or (H3PO4 and NaH2PO4), which decreased the concentration of H+ in the solution. The latter six salts showed a positive effect on the yield of trioxane in the reaction solution. The salt effect paralleled the ability of the salt to decrease the water activity of the reaction solution and followed the order KCl 2 2 3. Continuous production experiments were performed to investigate the salt effect on the concentration of trioxane in the distillate. The salts considered were KCl, NaCl, LiCl, ZnCl2, MgCl2, and FeCl3, and the salt effect increased progressively from left to right. Such an effect was shown to be determined by the ability of the salt to increase the yield of trioxane in the reaction solution and to increase the relative volatilities of trioxane and water and of trioxane and oligomers.
Study of trioxane production process with super- or subcritical fluid as solvent and extractant
Tanaka, Michio,Ogino, Kenji
, p. 1927 - 1932 (2006)
A super- or subcritical fluid was used as a reaction solvent for nonaqueous trioxane synthesis instead of common organic solvents. The generation of trioxane from paraformaldehyde was observed in the presence of the catalyst when carbon dioxide reached a supercritical region, suggesting that the supercritical carbon dioxide acted as the reaction solvent. In the case of Freon 12, the trioxane was effectively produced even in a subcritical state. Copyright Taylor & Francis Group, LLC.
Selective Reduction of CO2 to CH4 by Tandem Hydrosilylation with Mixed Al/B Catalysts
Chen, Jiawei,Falivene, Laura,Caporaso, Lucia,Cavallo, Luigi,Chen, Eugene Y.-X.
, p. 5321 - 5333 (2016)
This contribution reports the first example of highly selective reduction of CO2 into CH4 via tandem hydrosilylation with mixed main-group organo-Lewis acid (LA) catalysts [Al(C6F5)3 + B(C6F5)3] {[Al] + [B]}. As shown by this comprehensive experimental and computational study, in this unique tandem catalytic process, [Al] effectively mediates the first step of the overall reduction cycle, namely the fixation of CO2 into HCOOSiEt3 (1) via the LA-mediated C - O activation, while [B] is incapable of promoting the same transformation. On the other hand, [B] is shown to be an excellent catalyst for the subsequent reduction steps 2-4, namely the hydrosilylation of the more basic intermediates [1 to H2C(OSiEt3)2 (2) to H3COSiEt3 (3) and finally to CH4] through the frustrated Lewis pair (FLP)-type Si-H activation. Hence, with the required combination of [Al] and [B], a highly selective hydrosilylative reduction of CO2 system has been developed, achieving high CH4 production yield up to 94%. The remarkably different catalytic behaviors between [Al] and [B] are attributed to the higher overall Lewis acidity of [Al] derived from two conflicting factors (electronic and steric effects), which renders the higher tendency of [Al] to form stable [Al]-substrate (intermediate) adducts with CO2 as well as subsequent intermediates 1, 2, and 3. Overall, the roles of [Al] and [B] are not only complementary but also synergistic in the total reduction of CO2, which render both [Al]-mediated first reduction step and [B]-mediated subsequent steps catalytic.
Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide
Fu, Duo,Dong, Jun,Du, Hongguang,Xu, Jiaxi
, p. 2752 - 2758 (2020/01/31)
A phenyltrimethylammonium tribromide-mediated nucleophilic substitution/oxygen transformation reaction of benzyl halides with DMSO has been developed. In this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source, thus providing a convenient method for the efficient and direct synthesis of various benzyl methyl sulfoxides.