646-06-0 Usage
Chemical Properties
Colourless Liquid. Miscible with water, soluble in alcohol, ether and benzene. The azeotrope formed with water, the azeotrope is 70-73°C, and the water content is 6.7%. Decolorize bromine water.
Uses
1,3-Dioxolane is an intermediate for the preparation of Acyclovir (A192400). Also, 1,3-Dioxolane is used in the synthesis of new Vandetanib (V097100) analogs.
Definition
ChEBI: 1,3-dioxolane is a cyclic acetal that is pentane in which the carbon atoms at positions 1 and 3 are replaced by oxygen atoms respectively. It is a dioxolane and a cyclic acetal.
Application
1,3-Dioxolane (DOXL) is a cyclic ether. It is a green solvent. It undergoes reaction with C60 to afford an epoxide and 1,3-dioxolane derivative. Reaction has been reported to proceed via a diradical mechanism. A mixture of tetra(ethylene glycol) dimethyl ether (TEGDME) and DOXL has been used to compose the binary electrolyte for use in lithium-sulfur battery. Its efficacy as a solvent in a non-aqueous redox flow battery system has been tested. 1,3-Dioxolane may be used in the fabrication of batteries and capacitors. It may be used as one of the co-solvent to prepare the electrolyte for lithium-sulfur batteries.
General Description
A clear colorless liquid. Flash point 35°F. Slightly denser than water. Vapors heavier than air.
Air & Water Reactions
Highly flammable. When exposed to air 1,3-Dioxolane undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. Soluble in water.
Reactivity Profile
Ethers, such as 1,3-Dioxolane, can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
Health Hazard
Different sources of media describe the Health Hazard of 646-06-0 differently. You can refer to the following data:
1. Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.
2. The acute inhalation and oral toxicity of1,3-dioxolane is low in test animals. Thevapor is irritant to eyes and respiratory tract.Application of the liquid produced severeirritation in rabbits’ eyes and mild action onthe animals’ skin. The information on thetoxicity of this compound in humans is notknown.The inhalation LC50 value of 4-hour exposurein rats is in the range of 20,000 mg/m3,and the oral LD50 is 3000 mg/kg (NIOSH1986).
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Highlyflammable
Industrial uses
1,3-Dioxolane is used to dissolve a wide spectrum of polymeric materials such as
acrylates, alkyds, cellulosics, epoxies, polycarbonates, polyesters, urethanes, and
vinyl resins. In many cases, 1,3-dioxolane solvent can replace the chlorinated
solvents that were used previously to dissolve many of these polymers. The
excellent solvency of 1,3-dioxolane for polymeric compositions makes this cyclic
ether a valuable component in paint remover formulations. 1,3-Dioxolane is used to
treat polyester fibers for improved dye retention, application of cross-linking agents
to cellulosic fibers, and bonding of acrylonitrile polymers. 1,3-Dioxolane is used in
metal working and electroplating formulations, as a complexing solvent for
organometallic and inorganic salts, and in the preparation of lithium battery
electrolyte solutions. 1,3-Dioxolane is a valuable reactant in the polymerization
reactions to produce polyacetals. Polymerization reactions of dioxolane with itself
or with aldehydes and ethers are catalyzed by a Lewis acid to yield the polyacetal
polymers. The methylene group (CH2) bonded to the two oxygen atoms in
dioxolane is susceptible to radical abstraction of a hydrogen atom and the resultant
dioxolane radical species can be added across various double bond configurations.
Safety Profile
Moderately toxic by
ingestion and intraperitoneal routes. Mildly
toxic by skin contact and inhalation. A shin
and severe eye irritant. Mutation data
reported. A very dangerous fire hazard when
exposed to heat or flame; can react with
oxidizers. Used in lithium batteries.
Potentially explosive reaction with lithium perchlorate. When heated to decomposition
it emits acrid smoke and irritating fumes.
Purification Methods
Dry it with solid NaOH, KOH or CaSO4, and distil it from sodium or sodium amalgam. Barker et al. [J Chem Soc 802 1959] heated 34mL of dioxalane under reflux with 3g of PbO2 for 2hours, then cooled and filtered. After adding xylene (40mL) and PbO2 (2g) to the filtrate, the mixture is fractionally distilled. Addition of xylene (20mL) and sodium wire to the main fraction (b 70-71o) led to a vigorous reaction, following which the mixture was again fractionally distilled. Xylene and sodium additions are made to the main fraction (b 73-74o) before it is finally distilled. [Beilstein 19/1 V 6.]
Check Digit Verification of cas no
The CAS Registry Mumber 646-06-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 6 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 646-06:
(5*6)+(4*4)+(3*6)+(2*0)+(1*6)=70
70 % 10 = 0
So 646-06-0 is a valid CAS Registry Number.
InChI:InChI=1/C3H6O2/c1-2-5-3-4-1/h1-3H2
646-06-0Relevant articles and documents
Comparative Analysis of Electronic States of Saturated Dioxa and Dithia Heterocycles and Their Radical Cations
Momose, Takamasa,Tanimura, Ryuji,Ushida, Kinimori,Shida, Tadamasa
, p. 5582 - 5586 (1987)
ESR spectra of the radical cations of 1,3-dioxa- and 1,3-dithiacyclopentanes and their 2-methylated derivatives were studied both experimentally and theoretically.The orbital interaction analysis based on the localized orbital indicates that the order of the two highest occupied molecular orbitals is reversed between the dioxa and the dithia systems.It is concluded that the reversal is caused by the interaction of the orbital localized on the methylene C-H bonds of carbon atom 2 with the "out of plane" lone-pair MO composed of the lone-pair orbitals on the oxygen and the sulfur atoms.The use of the usual canonical orbital and the internally consistent SCF orbital proposed by Davidson as the base is discussed comparatively.
Efficient Plastic Waste Recycling to Value-Added Products by Integrated Biomass Processing
Beydoun, Kassem,Klankermayer, Jürgen
, p. 488 - 492 (2020/01/24)
The industrial production of polymeric materials is continuously increasing, but sustainable concepts directing towards a circular economy remain rather elusive. The present investigation focuses on the recycling of polyoxymethylene polymers, facilitated through combined catalytic processing of polymer waste and biomass-derived diols. The integrated concept enables the production of value-added cyclic acetals, which can flexibly function as solvents, fuel additives, pharmaceutical intermediates, and even monomeric materials for polymerization reactions. Based on this approach, an open-loop recycling of these waste materials can be envisaged in which the carbon content of the polymer waste is efficiently utilized as a C1 building block, paving the way to unprecedented possibilities within a circular economy of polyoxymethylene polymers.
A method for preparing 1, 3 - oxa naphthenic (by machine translation)
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Paragraph 0085; 0086-0090, (2019/05/16)
The invention discloses a 1, 3 - oxa naphthenic preparation method, the method comprises: diol, poly formaldehyde in water and ionic liquid catalyst in the presence of a cyclization reaction, containing the reaction product of the compound; wherein said diol is ethylene glycol or diethylene glycol; when the diol is ethylene glycol when, the target compound is 1, 3 - dioxolo; when the diol is diethylene glycol when, the target compound is 1, 3, 6 - heterocyclic octane; the ionic liquid catalyst comprises a cation and anion, the cation is selected from the isoquinoline kind of positive ion, quinoline kind of positive ion and benzimidazole in at least one of the kind of positive ion. The method of the invention the kind of positive ion cation is isoquinoline, quinoline kind of positive ion or benzimidazole kind of positive ion of the ionic liquid as catalyst to prepare 1, 3 - oxa naphthenic, mild reaction conditions, high product yield, catalyst is environment-friendly. (by machine translation)