111-90-0 Usage
Chemical Properties
Diethylene glycol monoethyl ether is a colorless, stable, hygroscopic liquid of a mild, pleasant odor. It is completely miscible with water, alcohols, ethers, ketones, aromatic and aliphatic hydrocarbons, and halogenated hydrocarbons. Owing to the fact that it contains an ether-alcohol-hydrocarbon group in the molecule, it has the power to dissolve a wide variety of substances such as oils, fats, waxes, dyes, camphor and natural resins like copal resin, kauri, mastic, rosin, sandarac, shellac, as well as several types of synthetic resins. It is used as a solvent in synthetic resin coating compositions, and in lacquers, where high-boiling solvents are desired.
Occurrence
Has apparently not been reported to occur in nature.
Uses
Different sources of media describe the Uses of 111-90-0 differently. You can refer to the following data:
1. Diethylene glycol monoethyl ether has low setting point and low viscocity at low temperature so it is used in manufacturing brake fluid. It is used as a flow and gloss promoter in paint industries, in production of printing ink and as a cleaner in offset printing. Also used in textile as a solvent for dyestuff in the printing and dying of fiber & fabrics, in the production & wood preservaties.
2. Di(ethylene glycol) ethyl ether is suitable for use as solvent for the polymer electrospinning.
3. Usually used as solvent for the polymer electrospinning.
Definition
ChEBI: A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.
Preparation
From ethyl alcohol plus ethylene oxide (Arctander, 1969).
General Description
A colorless, slightly viscous liquid with a mild pleasant odor. Flash point near 190°F. Used to make soaps, dyes, and other chemicals.
Air & Water Reactions
Slightly denser than water and soluble in water. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164].
Reactivity Profile
Mixing 2(2-Ethoxyethoxy)ethanol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid and oleum, NFPA 1991.
Health Hazard
None expected.
Fire Hazard
2(2-Ethoxyethoxy)ethanol is combustible.
Safety Profile
irritation, and unspecified eye effects, cough,
Metabolism
The major part of an administered dose of diethylene glycol monoethyl ether is oxidized in the body or excreted as the glucuronate, administration to rabbits orally or by sc injection being followed by a marked increase in the urinary content of glucuronic acid (Fellows, Luduena & Hanzlik, 1947).
Purification Methods
Ethylene glycol can be removed by extracting 250g in 750mL of *benzene with 5mL portions of water, allowing for phase separation, until successive aqueous portions show the same volume increase. Dry, and free from peroxides, as described for diethylene glycol mono-n-butyl ether. [Beilstein 1 IV 2393.]
Check Digit Verification of cas no
The CAS Registry Mumber 111-90-0 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 1 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 111-90:
(5*1)+(4*1)+(3*1)+(2*9)+(1*0)=30
30 % 10 = 0
So 111-90-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O3.C4H10O/c5-1-3-7-4-2-6;1-3-5-4-2/h5-6H,1-4H2;3-4H2,1-2H3
111-90-0Relevant articles and documents
Isergonic relationship in the acid-catalyzed hydrolysis of carboxylic esters with hydrogen-bonding capability
Mata-Segreda, Julio F.
, p. 567 - 571 (2007/10/03)
The average value of the enthalpies of activation for the acid-catalyzed hydrolyses of ethyl 2-hydroxypropanoate and five acetate esters with hydrogen bonding capability is 57 ± 7 kJ mol-1 (p = 0.05). This value is 11 kJ mol-1 lower than the mean observed for primary and secondary alkyl acetates and ethyl alkanoates, measured in water and in mixtures of water with organic solvent with high water content. The difference is attributed to tighter transition-state complex hydration via hydrogen bonding, relative to reactant ester species. Enthalpy-entropy compensation with an isokinetic temperature of 346 K was found to be valid at p 0.05, a value typical for solvent-mediated kinetic effects. Copyright
Synthesis of Trifluorovinyl Ethers Incorporating Functionalized Hydrocarbon Ether Groups: Insight into the Mechanism of Trifluorovinyl Ether Formation from Trimethylsilyl 2-Alkoxy-2,3,3,3-tetrafluoropropionates
Lousenberg, Robert D.,Shoichet, Molly S.
, p. 7844 - 7849 (2007/10/03)
Novel trifluorovinyl ethers (TFVEs, ROCF=CF2), where R is an oligoether, were synthesized from the corresponding sodium alkoxide and hexafluoropropene oxide.The sodium alkoxide ring opened hexafluoropropene oxide at the more highly substituted carbon (C2) to give 2-alkoxy-2,3,3,3-tetrafluoropropionic acid ester incorporating 2 equiv of the alcohol, ROCF(CF3)CO2R.Hydrolysis of the ester and reaction of the resulting sodium 2-alkoxy-2,3,3,3-tetrafluoropropionate with chlorotrimethylsilane gave the trimethylsilyl 2-alkoxy-2,3,3,3-tetrafluoropropionate, ROCF(CF3)CO2Si(CH3)3.Gas phase vacuum thermolysis of the trimethylsilyl ester at 140-150 deg C gave the corresponding TFVEs in 55-63percent yields.Thus, 1--1,2,2-trifluoroethene and 1--1,2,2-trifluoroethene were synthesized from 2-(2-ethoxyethoxy)ethanol and 2-(2-tert-butoxyethoxy)ethanol, respectively.Interestingly, thermolysis of sodium or potassium 2-alkoxy-2,3,3,3-tetrafluoropropionates resulted in negligible to low yields of TFVEs.1 For example, thermolysis of sodium 2--2,3,3,3-tetrafluoropropionate gave a trifluoroacetate ester, 2-(2-ethoxyethoxy)ethyl trifluoroacetate.Variable temperature 19F NMR spectroscopy of trimethylsilyl 2--2,3,3,3-tetrafluoropropionate suggests that an equilibrium exists between two structural conformations of these trimethylsilyl esters: one in which there is an intramolecular "interaction" of silicon with fluorine and one in which there is no silicon-fluorine interaction.This interaction may affect the outcome of the trimethylsilyl ester thermolysis.
