2-Ethoxyethanol

Base Information

• Chemical Name: 2-Ethoxyethanol
• CAS No.: 110-80-5
• Deprecated CAS: 96231-36-6
• Molecular Formula: C4H10O2
• Molecular Weight: 90.1222
• Hs Code.: 29094990
• European Community (EC) Number: 203-804-1
• ICSC Number: 0060
• NSC Number: 8837
• UN Number: 1171
• UNII: IDK7C2HS09
• DSSTox Substance ID: DTXSID7024087
• Nikkaji Number: J1.980A
• Wikipedia: 2-Ethoxyethanol
• Wikidata: Q209381
• NCI Thesaurus Code: C77465
• RXCUI: 1314365
• Metabolomics Workbench ID: 44755
• ChEMBL ID: CHEMBL119596
• Mol file: 110-80-5.mol

Synonyms:2-ethoxyethanol;Cellosolve;ethylcellosolve;ethylene glycol monoethyl ether;Oxitol

Chemical Property of 2-Ethoxyethanol

Chemical Property:

• Appearance/Colour: clear, colorless, nearly odorless liquid
• Vapor Pressure: 3.8 mm Hg ( 20 °C)
• Melting Point: -100 °C
• Refractive Index: n20/D 1.407(lit.)
• Boiling Point: 135.6 °C at 760 mmHg
• PKA: 14.44±0.10(Predicted)
• Flash Point: 44 °C
• PSA: 29.46000
• Density: 0.915 g/cm³
• LogP: 0.01520
• Storage Temp.: Flammables area
• Solubility.: water: miscible
• Water Solubility.: miscible
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 90.068079557
• Heavy Atom Count: 6
• Complexity: 21.5
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

2-Ethoxyethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-61-10-20/21/22-20/22
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Glycol Ethers (E Series)
• Canonical SMILES: CCOCCO
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and respiratory tract. The substance may cause effects on the central nervous system, blood, bone marrow, kidneys and liver. Exposure at high levels could cause unconsciousness. Medical observation is indicated.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the blood and bone marrow. This may result in anaemia and lesions of blood cells. May cause toxicity to human reproduction or development.
• Description: 2-Ethoxyethanol is a stable, colorless, flammable liquid, synthetically produced throughout the world. It belongs to a larger group of glycol ether solvents. 2-Ethoxyethanol is commercially referred to as Ethyl Cellosolve or Cellosolve, a trademark registered by Union Carbide in 1924. It was first synthesized to have the same chemical properties of both alcohols and ethers (hydrophilic and lipophilic) but less volatile, which improves production characteristics. The glycol ethers are made by reacting anhydrous alcohols with ethylene oxide.
• Physical properties: Clear, colorless liquid with a sweetish odor. Experimentally determined detection and recognition odor threshold concentrations were 1.1 mg/m3 (300 ppbv) and 2.0 mg/m3 (540 ppbv), respectively (Hellman and Small, 1974).
• Uses: 2-Ethoxyethanol is widely used as an industrial solvent and production intermediate. It is produced by the reaction of ethylene oxide with ethanol. The glycol ethers are miscible in polar and nonpolar solutions, which make them useful solvents in paints and surface coatings, stains, lacquers, inks, and dyes. Additional uses include industrial deicing, hydraulic fluids, and cleaning agents. 2-Ethoxyethanol was once used in cosmetic products but is no longer used due to toxicity associated with dermal absorption. Global production has been on the decline in recent years based on demonstrated toxicity through oral, dermal, and inhalation routes of exposure. The use of ethylene glycol ethers has largely been replaced by relatively safer substitutes, primarily propylene glycol ethers; however, their use as a solvent and chemical process intermediate poses potential for release into the environment. Ethylene glycol monoethyl ether is used in varnish removers, lacquers, and as a solvent for printing inks, duplicating fluids, and epoxy. Ethylene glycol monobutyl ether is used in hydraulic fluids, as a coupling agent for water-based coatings, in vinyl and acrylic paints and varnishes, and as a solvent for varnishes, enamels, spray lacquers, dry cleaning compounds, textiles, and cosmetics. Ethylene glycol monoethyl ether (EGEE) isused as a solvent for nitrocellulose, lacquers,and varnishes; in dye baths and cleansingsolutions; and as an emulsion stabilizer. antiobesity agent pancreatic lipase inhibitor

Technology Process of 2-Ethoxyethanol

There total 64 articles about 2-Ethoxyethanol 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: 47.2%

oxirane (75-21-8,99932-75-9) + ethanol (64-17-5) → 2-ethoxy-ethanol (110-80-5)

Guidance literature:

With carbon dioxide; at 149.84 ℃; for 3h; under 22502.3 Torr;

DOI:10.1016/j.apcata.2013.11.031

Reference yield: 29.6%

oxirane (75-21-8,99932-75-9) + ethanol (64-17-5) + carbon dioxide (124-38-9,18923-20-1) → [1,3]-dioxolan-2-one (96-49-1) + 2-ethoxy-ethanol (110-80-5) + ethylene glycol (107-21-1) + Diethyl carbonate (105-58-8,76619-83-5)

Guidance literature:

With sodium ethanolate; potassium bromide; at 423 ℃; for 3h; under 22502.3 Torr;

DOI:10.1016/j.apcata.2013.11.031

Reference yield: 21.4%

oxirane (75-21-8,99932-75-9) + ethanol (64-17-5) → 2-ethoxy-ethanol (110-80-5) + ethylene glycol (107-21-1)

Guidance literature:

at 149.84 ℃; for 3h; under 22502.3 Torr; Inert atmosphere;

DOI:10.1016/j.apcata.2013.11.031

upstream raw materials:

oxirane

ethanol

sodium ethanolate

ethyl 2-ethoxyethanoate

Downstream raw materials:

ethoxyethoxyethanol

phenyl-phosphonic acid bis-(2-ethoxy-ethyl ester)

oxalic acid bis-(2-ethoxy-ethyl ester)

benzyl cellosolve

Refernces

• 1、 Garcia-Rio, L.,Leis, J. R.,Mejuto, J. C.. "Pseudophase Approach to Reactivity in Microemulsions: Quantitative Explanation of the Kinetics of the Nitrosation of Amines by Alkyl Nitrides in AOT/Isooctane/Water Microemulsions". . p. 10981 - 10988. Retrieved 1996.
• 2、 Boonmongkolras, Passarut,Choi, Eun-Gyu,Han, Seunghyun,Kim, Jinhyun,Kim, Kayoung,Kim, Yong Hwan,Lee, Sahng Ha,Lee, Yang Woo,Park, Chan Beum,Shin, Byungha,Trang, Nguyen Vu Thien,Wang, Ding. "Lignin-fueled photoelectrochemical platform for light-driven redox biotransformation". supporting information. p. 5151 - 5160. Retrieved 2020/08/25.
• 3、 Bortoluzzi, Marco,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano. "Reactivity of [WCl6] with Ethers: A Joint Computational, Spectroscopic and Crystallographic Study". . p. 3169 - 3177. Retrieved 2016/07/14.