Dioxane

Base Information

• Chemical Name: Dioxane
• CAS No.: 123-91-1
• Deprecated CAS: 28347-88-8,28347-91-3,39449-24-6,54841-74-6,28347-91-3,39449-24-6
• Molecular Formula: C4H8O2
• Molecular Weight: 88.1063
• Hs Code.: 29329990
• European Community (EC) Number: 204-661-8
• ICSC Number: 0041
• NSC Number: 8728
• UN Number: 1165
• UNII: J8A3S10O7S
• DSSTox Substance ID: DTXSID4020533
• Nikkaji Number: J2.502J
• Wikipedia: 1,4-Dioxane
• Wikidata: Q161532,Q83069696
• NCI Thesaurus Code: C44298
• RXCUI: 2383534
• Metabolomics Workbench ID: 52456
• ChEMBL ID: CHEMBL453716
• Mol file: 123-91-1.mol

Synonyms:1,4-dioxane;diethylene ether;dioxan;dioxane;p-dioxane

Chemical Property of Dioxane

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 27 mm Hg ( 20 °C)
• Melting Point: 12 °C
• Refractive Index: n20/D 1.422(lit.)
• Boiling Point: 102.9 °C at 760 mmHg
• Flash Point: 12.2 °C
• PSA: 18.46000
• Density: 0.995 g/cm³
• LogP: 0.03320
• Storage Temp.: Flammables area
• Sensitive.: Hygroscopic
• Solubility.: Soluble in acetone, alcohol, benzene, and ether (Weast, 1986). Miscible with most organic solvents (Huntress and Mulliken, 1941) including 2-methylpropanol, toluene, cychexanone, and cyclopentanone.
• Water Solubility.: SOLUBLE
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 26.5
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dioxane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: Xn,F,T
• Statements: 45-46-11-36/38-48/23/24/25-65-66-40-36/37-19-41-37/38-39/23/24/25-23/24/25-48/20/22-38-22-36/37/38-10
• Safety Statements: 9-16-36/37-46-45-53-7-62-26-24/25-23-S9-S46-S36/37-S16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ethers (
• Canonical SMILES: C1COCCO1
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C , on spraying or dispersing much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis. Exposure at high levels could cause lowering of consciousness.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the central nervous system, kidneys and liver. This substance is possibly carcinogenic to humans.
• description: 1,4-Dioxane is a hexahydroxy heterocyclic compound containing two oxygen heteroatoms. molecular formula C4H8O2，a colorless, flammable liquid, slight ether smell, photosensitive. Its Vapor can easily form explosive peroxides by absorbing oxygen in the air. Explosion limit 1.97%-1.97% (volume), It should be disposed by reducing agent in distillation process. Melting point 11.8 ℃, boiling point of 101 ℃ (750 mmHg), density 1.0337 (20/4 ℃), refractive index 1.4224, flash point12℃. Soluble in water, ethanol, ether and other organic solvents. It can form azeotrope with water (water content 18.6%) and the boiling point is 87.8 ℃. It turns bright yellow when reacting with tetranitromethane. Trace amount of 2,6-Di-tert-butyl-4-methylphenol(BHT) is often added to the commodity as a stabilizer. Low toxicity, half lethal dose (rats, oral) 4200 mg/kg. A possible carcinogen, an irritating chemical. 1,4-Dioxane can be prepared by dehydration of ethylene glycol by sulfuric acid and it is the indirect product in the production of epoxy ethane. As a good organic solvent, it has a wide application such as the solvent for cellulose acetate and lots of resins. It Is mainly used in the pharmaceutical industry as extraction agent, as a stabilizer in the production of 1,1,1 – trichloroethane as a volatile solvent in the production of polyurethane in place of dimethylformamide and tetrahydrofuran, as stripping agent in the crafts of coating and painting, as a solvent and dispersant in the dye industry, as a stabilizer in printing ink, and also as treatment agent for metal surface. In addition , it can also be used in cosmetics, spices manufacture, electroplating, etc.
• uses: Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.
• Description: 1,4-dioxane is a clear liquid with ether-like odour. It is highly flammable and forms explosive peroxides in storage (rate of formation increased by heating, evaporation, or exposure to light). 1,4-Dioxane is incompatible with oxidising agents, oxygen, halogens, reducing agents, and moisture. Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.
• Physical properties: Clear, colorless, very flammable, volatile liquid with a faint pleasant, ether-like odor. Experimentally determined detection and recognition odor threshold concentrations were 2.9 mg/m3 (800 ppbv) and 6.5 mg/m3 (1.8 ppmv), respectively (Hellman and Small, 1974).
• Uses: 1,4-Dioxane is used as a solvent for celluloseesters, oils, waxes, resins, and numerousorganic and inorganic substances. It is alsoused in coatings and as a stabilizer in chlorinatedsolvents. 1,4-Dioxane, the six-member cyclic diether, is used as an aluminum inhibitor in chlorinated solvents like 1,1,1-trichloroethane and as a solvent for certain resins and polymers. Stabilizer in chlorinated solvents. Solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, oil and spirit-sol dyes, and many other organic as well as some inorganic Compounds.

Technology Process of Dioxane

There total 159 articles about Dioxane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.9%

ethylene glycol (107-21-1) → 2-methyl-1,3-dioxolane (497-26-7) + 1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + acetaldehyde (75-07-0,9002-91-9) + diethylene glycol (111-46-6)

Guidance literature:

With tungsten trioxide on silica; hydrogen; In water; at 340 ℃; Temperature; Inert atmosphere;

DOI:10.1016/j.apcata.2016.08.029

Reference yield: 5.0%

oxirane (75-21-8,99932-75-9) → 1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + 2-fluoroethanol (371-62-0)

Guidance literature:

With hydrogen fluoride; under 380 Torr; Product distribution;

DOI:10.1039/P29810001336

Reference yield:

2,2-dimethyl-3,6,9,12-tetraoxa-2-silatridecane (864079-62-9) → 1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + Dimethyl ether (115-10-6,157621-61-9) + Trimethylmethoxysilane (1825-61-2) + Hexamethyldisiloxane (107-46-0)

Guidance literature:

With Cp*Si⁽¹⁺⁾* B(C₆F₅)4^(1-); In dichloromethane-d2; at -30 ℃; Inert atmosphere;

DOI:10.1002/anie.201101139

upstream raw materials:

oxirane

triethyloxonium fluoroborate

Cbz-L-Gln

N-L-asparaginyl-S-benzyl-L-cysteine methyl ester

Downstream raw materials:

9-methoxy-2-methyl-benzo[f]chromen-3-one

17-hydroxyprogesterone

retusin

p-tolylsulphonylacetamide

Refernces

• 1、 Eychenne-Baron, Christophe,Ribot, Fran?ois,Steunou, Nathalie,Sanchez, Clément,Fayon, Franck,Biesemans, Monique,Martins, José C.,Willem, Rudolph. "Reaction of butyltin hydroxide oxide with p-toluenesulfonic acid: Synthesis, X-ray crystal analysis, and multinuclear NMR characterization of {(BuSn)12O14(OH)6}(4-CH3C 6H4SO3)2". . p. 1940 - 1949. Retrieved 2000.
• 2、 Skarulis,Ricci. "". . p. 3429. Retrieved 1941.
• 3、 Gordon et al.. "-". . p. 583,587. Retrieved 1955.
• 4、 Gruhn,Gorman. "". . p. 482. Retrieved 1965.
• 5、 Weicksel, J. A.,Lynch, C. C.. "". . p. 2632 - 2636. Retrieved 1950.
• 6、 Stone,Emeleus. "-". . p. 2755,2757. Retrieved 1950.
• 7、 Rohand, Taoufik,Tanemura, Kiyoshi. "Catalysis, kinetic and mechanistical studies for the transformation of ethylene glycol by alumina and silica gel under autogenous pressure and solvent-free conditions". . p. 387 - 394. Retrieved 2021/06/25.
• 8、 Biberger, Tobias,Makai, Szabolcs,Lian, Zhong,Morandi, Bill. "Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers". supporting information. p. 6940 - 6944. Retrieved 2018/05/14.