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Home > Encyclopedia > 1,3,5-Trioxane

1,3,5-Trioxane

1,3,5-Trioxane structure

1,3,5-Trioxane 

structure
  • CAS No:

    110-88-3

  • Formula:

    C3H6O3

  • Chemical Name:

    1,3,5-Trioxane

  • Synonyms:

    1,3,5-Trioxane;s-Trioxane;Trioxane;Triformol;Trioxan;sym-Trioxane;Trioxymethylene;Formaldehyde,trimer;NSC 26347;T 0505;113783-48-5

  • Categories:

    Organic Chemistry  >  Aldehydes

Description

WHITE SOLID IN VARIOUS FORMS WITH PUNGENT ODOUR.


Transparent 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.|OtherSolid


Transparent 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.|1,3,5-trioxane 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. It is a trioxane and a saturated organic heteromonocyclic parent.

1,3,5-Trioxane Basic Attributes

90.08

90.08

102769

203-812-5

46BNU65YNY

26347

1325

DTXSID4021925

CRYSTALLINE SOLID|RHOMBIC NEEDLES FROM ETHER|WHITE

2934999090

Characteristics

27.7

-0.62

Colorless to white Crystals or Crystalline Flakes

1.17 g/cm3 @ Temp: 65 °C

64 °C

114.5 °C @ Press: 759 Torr

113 °F

1.385

H2O: 221 g/L (25 ºC)

Flammables area

Vapour pressure, kPa at 25°C:

Relative vapour density (air = 1): 1.03

It is flammable in case of open flame, high temperature and oxidant; produces toxic formaldehyde gas in case of strong acid and heat

3.6-28.7%(V)

CHARACTERISTIC CHLOROFORM-LIKE ODOR

6.20e-12 cm3/molecule*sec

ON DISTILLATION WITH WATER, FORMS AZEOTROPE BOILING @ 91.4 °C CONTAINING APPROX 70% TRIOXANE BY WT|SUBLIMES READILY; SLOWLY DEPOLYMERIZED BY STRONG ACIDS IN AQ SOLN; INERT TO ALKALIES

Highly flammable. Water soluble.

Ethers

Highly Flammable

1,3,5-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 (NTP, 1992). 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.

1,3,5-Trioxane|D*: Other compounds that may form peroxides|Bretherick's|Contact detonation occured while trying to break up clumps of trioxane. See Bretherick's.

777 °F (NTP, 1992)|777 °F

Safety Information

III

4.1

UN 1325 4.1/PG 2

1

11-37-63

36/37-46

YK0350000

F,Xn

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

Mixed with oxidant, open flame can be explosive

STABLE, CYCLIC TRIMER OF FORMALDEHYDE

P210-P261-P281

H228-H335-H361d

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Incineration & landfill: Mix with a combustible solvent and incinerate using an afterburner or bury in an approved landfill.

This chemical is combustible. (NTP, 1992)

|Warning|H228: Flammable solid [Danger Flammable solids]|P201, P202, P210, P240, P241, P261, P271, P280, P281, P304+P340, P308+P313, P312, P370+P378, P403+P233, P405, and P501|H228 (100%): Flammable solid [Danger Flammable solids]|Aggregated GHS information provided by 296 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H336: May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]|P201, P202, P260, P261, P271, P281, P304+P340, P308+P313, P312, P314, P403+P233, P405, and P501

Excerpt from ERG Guide 133 [Flammable Solids]: As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 100 meters (330 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. This compound is a Schedule IV DEA Controlled Substance and is to be stored according to State and Federal Regulations. Refer to Code of Federal Regulations Title 21 Part 1300 to End. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

MODERATE FIRE RISK.|VOLATILE SOLID THAT GIVES OFF FLAMMABLE VAPOR OF FORMALDEHYDE WHEN HEATED. /PARAFORMALDEHYDE/

EXPLOSIVE LIMITS IN AIR 3.5-29%.

USE WATER SPRAY, CARBON DIOXIDE, DRY CHEM OR "ALCOHOL" FOAM. WATER SPRAY MAY BE USED TO FLUSH SPILLS AWAY FROM EXPOSURES. /PARAFORMALDEHYDE/|WATER SPRAY MAY BE USED TO EXTINGUISH THE FIRE BECAUSE MATERIAL CAN BE COOLED BELOW ITS FLASH POINT.|ALCOHOL FOAM.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

PARAFORM INTRODUCES BOTH A DUST & A FORMALDEHYDE GAS EXPOSURE... /PARAFORM/

Drug Information

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OUNCE FOR 70 KG PERSON (150 LB).

SAME INTERNAL TOXICITY AS FORMALDEHYDE, WHICH IT SLOWLY RELEASES AT BODY TEMP.

ACUTE/CHRONIC HAZARDS: This compound is toxic and flammable. It can emit toxic fumes on contact with acid or acid fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

SEE FORMALDEHYDE. 1. ADMIN BY MOUTH 1 OR MORE OF FOLLOWING: WATER, MILK, 0.2% AMMONIA WATER...AMMONIUM ACETATE (3 TEASPOONSFUL IN WATER), EGG WHITES, ACTIVATED CHARCOAL. AMMONIUM SALTS ARE PROBABLY BEST BECAUSE THEY TRANSFORM FORMALDEHYDE INTO METHENAMINE... /FORMALDEHYDE/|SEE FORMALDEHYDE. 2. DEMULCENTS: MILK, EGGS, ALUMINUM HYDROXIDE GELS. 3. MORPHINE FOR CONTROL OF PAIN... 4. COMBAT SHOCK BY IV ADMIN OF ISOTONIC SALINE, PLASMA, OR WHOLE BLOOD... 5. TO CORRECT ACIDOSIS, GIVE SODIUM BICARBONATE OR M/6 SODIUM LACTATE SOLN IV... 6. ARTIFICIAL RESP, IF INDICATED... /FORMALDEHYDE/|SEE FORMALDEHYDE. 7. PENICILLIN OR OTHER ANTIBIOTIC IF INFECTION APPEARS... 8. WASH AFFECTED SKIN WITH LARGE QUANTITIES OF SOAP & WATER. LAB. URINALYSIS MAY REVEAL RED BLOOD CELLS (SOMETIMES GROSS HEMATURIA) & CASTS. /FORMALDEHYDE/

MALE & FEMALE 4TH YR DENTAL STUDENTS SHOWED HIGH INCIDENCE OF LATENT ALLERGIES, 65% COMPARED TO 13.6% FOR SAME STUDENTS @ END OF 2ND YR. ATTRIBUTED TO EXPOSURE TO ALLERGY-PRODUCING SUBSTANCES SUCH AS TRIOXYMETHYLENE.|SAME INTERNAL TOXICITY AS FORMALDEHYDE, WHICH IT SLOWLY RELEASES AT BODY TEMP.|SEE FORMALDEHYDE. SYMPTOMATOLOGY: A. INHALATION. 1. IRRITATION OF MUCOUS MEMBRANES, ESP OF EYES, NOSE & UPPER RESP TRACT. 2. WITH HIGHER CONCN, COUGH, DYSPHAGIA, BRONCHITIS, PNEUMONIA, EDEMA OR SPASM OF LARYNX. /FORMALDEHYDE/|SEE FORMALDEHYDE. SYMPTOMATOLOGY: B. INGESTION. 1. ...PAIN IN MOUTH, PHARYNX & STOMACH. 2. NAUSEA, VOMITING, HEMATEMESIS, ABDOMINAL PAIN, &...DIARRHEA (WHICH MAY BE BLOODY). 3. ...SHOCK. 4. DIFFICULT MICTURITION, HEMATURIA, ANURIA. 5. VERTIGO, CONVULSIONS...COMA. 6. DEATH DUE TO RESP FAILURE. /FORMALDEHYDE/|SEE FORMALDEHYDE. SYMPTOMATOLOGY: SKIN CONTACT. 1. IRRITATION & HARDENING OF SKIN. STRONG SOLN PRODUCE COAGULATION NECROSIS. 2. DERMATITIS & HYPERSENSITIVITY FROM PROLONGED EXPOSURE. /FORMALDEHYDE/

s-trioxane

1,3,5-Trioxane Use and Manufacturing

Methods of Manufacturing

The 60% formaldehyde aqueous solution containing 2%-5% sulfuric acid is continuously distilled, and the residual liquid is extracted with benzene and then distilled to prepare. Under certain conditions, it can also generate paraformaldehyde. Tetraformaldehyde has a melting point of 112°C and a boiling point of 175°C. Both paraformaldehyde and tetraformaldehyde can be decomposed into formaldehyde under the action of acid, which is a special form of formaldehyde.

Uses

1,3,5-Trioxane is used in organic chemical processes such as aldol condensation of amides and syntheses of chloromethyl esters or other plastics.


Intermediates


Building/construction materials - wood and engineered wood products

Pharmaceutical and medicine manufacturing|1,3,5-Trioxane: ACTIVE|SYM-TRIOXANE...A TRIMER OF FORMALDEHYDE; NOT TO BE CONFUSED WITH PARAFORMALDEHYDE...WHICH CONSISTS OF 8 OR MORE FORMALDEHYDE UNITS.|IN NON-AQ SYSTEMS, READILY CONVERTED TO MONOMERIC FORMALDEHYDE BY SMALL CONCN STRONG ACIDS @ RATE DETERMINED BY ACID CONCN.|SUBLIMABLE PERFUME COMPOUNDS CONTAIN TRIOXYMETHYLENE.|CYCLIC ETHERS SUCH AS SYM-TRIOXANE ARE USED TO PREVENT DECOMP OF HALOAMIDE ANTIMICROBIAL AGENTS, SUCH AS DBNPA.

Agrochemicals -> Fungicides

Computed Properties

Molecular Weight:90.08
XLogP3:-0.4
Hydrogen Bond Acceptor Count:3
Exact Mass:90.031694049
Monoisotopic Mass:90.031694049
Topological Polar Surface Area:27.7
Heavy Atom Count:6
Complexity:21.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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