Diethylene glycol

Base Information

• Chemical Name: Diethylene glycol
• CAS No.: 111-46-6
• Deprecated CAS: 4669-26-5,2126734-27-6
• Molecular Formula: C4H10O3
• Molecular Weight: 106.122
• Hs Code.: 2909.41
• European Community (EC) Number: 203-872-2
• ICSC Number: 0619
• NSC Number: 36391,35746,35745,35744,32856,32855
• UNII: 61BR964293
• DSSTox Substance ID: DTXSID8020462
• Nikkaji Number: J5.110A
• Wikipedia: Diethylene glycol,Diethylene_glycol
• Wikidata: Q421902
• Metabolomics Workbench ID: 52447
• ChEMBL ID: CHEMBL1235226
• Mol file: 111-46-6.mol

Synonyms:diethylene glycol

Chemical Property of Diethylene glycol

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 0.01 mm Hg ( 20 °C)
• Melting Point: -10 °C(lit.)
• Refractive Index: n20/D 1.447(lit.)
• Boiling Point: 245.689 °C at 760 mmHg
• PKA: 14.03±0.10(Predicted)
• Flash Point: 143.333 °C
• PSA: 49.69000
• Density: 1.106 g/cm³
• LogP: -1.01240
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: H2O: 50 mg/mL at 20 °C, clear, colorless
• Water Solubility.: SOLUBLE
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 106.062994177
• Heavy Atom Count: 7
• Complexity: 26.1

Purity/Quality:

99%Min ^*data from raw suppliers

Diethylene Glycol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T,Xi
• Hazard Codes: Xn,T,Xi
• Statements: 22
• Safety Statements: 46

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Ethylene Glycols
• Canonical SMILES: C(COCCO)O
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance may cause effects on the kidneys. This may result in kidney impairment. Ingestion could cause effects on the central nervous system and liver. Ingestion could cause death.
• Chemical Properties: Diethylene glycol (DEG) is a clear, practically odorless, colorless, and viscous liquid with a sweetish taste. It is soluble in water and ethanol.
• Industrial Uses: DEG has numerous industrial applications, including use as an antifreeze agent, chemical intermediary, solvent, heat transfer fluid, brake fluid, cement processing, and lubricant.
• Toxicity: While DEG itself has low toxicity, it undergoes biotransformation in the liver, leading to the production of highly toxic metabolites such as 2-hydroxyethoxyacetic (2-HEAA) and diglycolic acid (DGA). These metabolites can persist in the body for a long time and cause acute toxic syndrome, resulting in renal failure due to cortical tubular degeneration and proximal tubular necrosis.
• Adulteration in Pharmaceuticals: DEG has been mistakenly used as a less expensive alternative to glycerin in pharmaceutical preparations, resulting in fatal poisonings. Clinical manifestations of DEG poisoning include hepatotoxicity, metabolic acidosis, and acute kidney injury.
• Analytical Detection: Various analytical methods, including gas chromatography with flame ionization detection (GC-FID) and ultra-performance liquid chromatography鈥搕ime of flight mass spectrometry (UHPLC-MS), have been developed to detect DEG in pharmaceuticals, healthcare products, alcoholic beverages, toothpaste, food items, and even human plasma.
• Textile Printing: DEG has been utilized in digital inkjet printing technology for textile printing. Addition of DEG can improve the printability of reactive dye inks, change the aggregation of dye molecules, inhibit formation of satellite droplets, and enhance color strength and brightness in printed fabrics.

Technology Process of Diethylene glycol

There total 54 articles about Diethylene glycol 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: 99.8%

[1,3]-dioxolan-2-one (96-49-1) + methanol (67-56-1) → ethylene glycol (107-21-1) + carbonic acid dimethyl ester (616-38-6) + diethylene glycol (111-46-6)

Guidance literature:

potassium hydroxide; at 63.8 - 98 ℃; for 6.7h; Product distribution / selectivity;

Reference yield: 72.0%

[1,3]-dioxolan-2-one (96-49-1) + methanol (67-56-1) → 2-methoxy-ethanol (109-86-4,95507-80-5) + ethylene glycol (107-21-1) + carbonic acid dimethyl ester (616-38-6) + diethylene glycol (111-46-6)

Guidance literature:

at 76.7 - 79.6 ℃; under 757.576 Torr; Product distribution / selectivity; Industry scale;

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

upstream raw materials:

oxirane

ethylene glycol

ethylene dibromide

2-bromoethanol

Downstream raw materials:

Tetraethylene glycol

Pentaethylene glycol

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

bis-[2-(2-benzyloxycarbonyl-benzoyloxy)-ethyl]-ether

Refernces

• 1、 Ding, Tong,Gao, Guohua,Xia, Fei,Yuan, Huixia,Zha, Jinyin,Zhang, Dawei,Zhang, Jingshun. "CO2atmosphere enables efficient catalytic hydration of ethylene oxide by ionic liquids/organic bases at low water/epoxide ratios". supporting information. p. 3386 - 3391. Retrieved 2021/05/25.
• 2、 -. "Chromium-Catalyzed Production of Diols From Olefins". Paragraph 0111. . Retrieved 2021/03/19.