ChemicalBook > Product Catalog > Organic Chemistry > Alcohols,Phenols,Phenol alcohols > Acyclic alcohols > Diethylene glycol
Diethylene glycol Chemical Properties
- Melting point:−10 °C(lit.)
- Boiling point:245 °C(lit.)
- Density 1.118 g/mL at 25 °C(lit.)
- vapor density 2.14 (vs air)
- vapor pressure 0.01 mm Hg ( 20 °C)
- refractive index n
- Flash point:143 °C
- storage temp. Keep in dark place,Sealed in dry,Room Temperature
- solubility H2O: 50 mg/mL at 20 °C, clear, colorless
- form Oily Liquid
- color colorless
- OdorPractically odorless.
- Relative polarity0.713
- PH5.5-7.0 (25℃, 50mg/mL in H2O)
- explosive limit2-12.3%
- Water Solubility SOLUBLE
- FreezingPoint -10.45℃
- Sensitive Hygroscopic
- λmaxλ: 260 nm Amax: ≤0.02
λ: 280 nm Amax: ≤0.01
- Merck 14,3119
- BRN 969209
- CAS DataBase Reference111-46-6(CAS DataBase Reference)
- NIST Chemistry ReferenceEthanol, 2,2'-oxybis-(111-46-6)
- EPA Substance Registry SystemDiethylene glycol (111-46-6)
- Hazard Codes Xn,T,Xi
- Risk Statements 22
- Safety Statements 46
- WGK Germany 1
- RTECS ID5950000
- F 10
- Autoignition Temperature442 °F
- Hazard Note Toxic/Irritant
- TSCA Yes
- HS Code 29094100
- Hazardous Substances Data111-46-6(Hazardous Substances Data)
- ToxicityLD50 in rats, guinea pigs (g/kg): 20.76, 13.21 orally (Smyth)
Diethylene glycol Usage And Synthesis
- Chemical PropertiesDiethylene glycol is a clear colorless, odorless and stable oily liquid. It is also slightly viscous, noncorrosive and nonvolatile. Because of its ether and alcohol group, diethylene glycol exhibits chemical properties characteristic of both primary alcohols and ethers. Its boiling point is considerably higher than that of ethylene glycol, and its solvent is greater. Diethylene glycol is miscible with water, ethers, lower aliphatic alcohols, aldehydes and ketones and is partially soluble in benzene, carbon tetrachloride, monobenzene, orthodichlorobenzene and toluene. It dissolves many dyes, resins, oils, nitrocellulose and many organic substances. Because of its solvent power, low volatility and hygroscopicity, it is used in textile lubricants, cutting oils, dry cleaning soap, printing inks, steam-set inks, and nongrain wood stains. In the textile industry diethylene glycol is used as a conditioning agent for wool, rayon, and cotton. As a solvent for dyes it makes a valuable assistant in dyeing and printing. The high hygroscopicity of diethylene glycol makes it an efficient softening agent for tobacco, paper, synthetic sponges, glues and casein. Diethylene glycol is especially useful in the dehydration of natural gas. A mixture of diethylene glycol and monoethanolamine will remove moisture, hydrogen sulfide and carbon dioxide from natural gas.
diethylene glycol structure
- UsesIn antifreeze solution for sprinkler systems, water seals for gas tanks, etc. (water with 40% diethylene glycol freezes at -18°; with 50% at -28°); as lubricating and finishing agent for wool, worsted, cotton, rayon, and silk; as solvent for vat dyes; in composition corks, glues, gelatin, casein, and pastes to prevent drying out.
- UsesDiethylene glycol is a colorless, odorless, clear liquid. It is miscible with water in any ratio. It has many industrial uses. It is a component of antifreeze, brake fluids, cosmetics, inks, and drying agents, and it is used as a plasticizer.
- UsesDiethylene glycol (DEG) is a commonly used solvent and ingredient in numerous commercial products. It is used as a dehydrating agent for natural gas processing; as a lubricating and finishing agent for textiles; a constituent in brake fluids, lubricants, antifreeze formulations, wallpaper strippers and in artificial fog solutions; a solvent for printing inks and textile dyes; and is used as an intermediate in the production of some resins, triethylene glycol, surfactants, and diethylene glycol esters and ethers.
- Production MethodsDiethylene glycol is produced commercially as a by-product of ethylene glycol production. It can also be produced directly by reaction between ethylene glycol and ethylene oxide .
- General DescriptionA colorless liquid. Denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.
- Air & Water ReactionsSlightly soluble in water.
- Reactivity ProfileDiethylene glycol is incompatible with strong oxidizing agents. Diethylene glycol is also incompatible with strong bases. Diethylene glycol can react with sulfuric acid and other dehydrating agents, nitric acid, oxygen, hydrogen peroxide, perchloric acid and strong acids. Mixtures with sodium hydroxide decompose exothermically when heated to 446° F.
- Health HazardIngestion of large amounts may cause degeneration of kidney and liver and cause death. Liquid may cause slight skin irritation.
- Fire HazardDiethylene glycol is combustible.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pert.
- ToxicologyThe toxicity of diethylene glycol is similar to ethylene glycol and clearly is a CNS depressant. It has a low inhalation hazard because of its low vapor pressure; however, inhalation of the mist or aerosol is to be avoided. Workplace levels for vapors and aerosols cannot exceed 50 ppm. In case of accidental release of diethylene glycol, use of a full-face positive air pressure respirator is recommended. Even though the toxicokinetics in humans is not completely understood, its toxic nature is confirmed by animal studies. Several human cases were reported in the medical literature. Several children in Haiti died in 1995 and 1996 following the consumption of medication containing diethylene glycol. Similar other cases in children were reported in other countries as well. A 24-year-old man developed encephalopathy and rapidly became quadriplegic following ingestion of a solution containing diethylene glycol . Thus, the toxicity of diethylene glycol is well established.
- Safety ProfileModerately toxic to humans by ingestion. Poison experimentally by inhalation. Moderately toxic by ingestion and intravenous routes. Questionable carcinogen with experimental carcinogenic,tumorigenic, and teratogenic data. An eye and human skin irritant. Combustible when exposed to heat or flame; can react with oxidning materials. To fight fire, use alcohol foam, water, Con, dry chemical. Mixtures with sodium hydroxide decompose exothermically when heated to 230℃ and release explosive hydrogen gas. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.
- CarcinogenicityWeil et al. , in their longterm studies on rats of three different age levels, found only one bladder tumor in those fed diets that contained 4% diethylene glycol. This tumor was in a rat that also had bladder stones . To clarify the question of the cause of the tumor, Weil et al. implanted calcium oxalate stones or glass beads into the bladders of rats. They found that bladder tumors never developed without the presence of a foreign body in the bladder. This led to the conclusion that diethylene glycol essentially free of ethylene glycol is not a primary carcinogen.
- Environmental FateDiethylene glycol is metabolized by alcohol dehydrogenase to toxic metabolites predominantly, HEAA and DGA. DEG can cause an anion gap metabolic acidosis, cortical necrosis resulting in permanent renal failure and neurotoxicity. DGA, not HEAA, was recently identified as being the primary nephrotoxic agent causing proximal tubule cell death. The neurotoxicity seen after DEG poisoning is only recently described. The neurotoxicity is delayed and has cranial and peripheral demyelinating sensorimotor polyneuropathy pattern. The exact mechanism of the neurotoxicity remains unclear and in the cases described in the literature, it appears to be prolonged but does show evidence of reversibility.
- Toxicity evaluationDiethylene glycol is miscible with water, has a low vapor
pressure of 0.008 hPa at 25°C, a very low log Kow of 1.98, and also a low Koc. Consequently, water is the most relevant environmental
compartment. Calculation according to Mackay,
Level I indicates the following distribution among environmental
compartments: air 0.75%, water 99.25%, soil 0%,
sediment 0%; confirming the relevance of the pelagic systems.
The substance is readily biodegradable and the very low log Kow suggests a low potential for bioaccumulation.
Diethylene glycol Preparation Products And Raw materials
- Preparation ProductsTolueneBenzeneXyleneEthylene glycol1-Oxa-4-azacyclohexaneCasein4-BENZYLPIPERIDINE4-Methylmorpholine 2-Chloro-4-dodecylphenolUnsaturated polyester resin4-(4-Methoxyphenyl)butyric acid6-PHENYLHEXANOIC ACID2,6-Dichloroindophenol sodium salt4-(2-THIENYL)BUTYRIC ACID1-PYRENEBUTYRIC ACID1-PYRENEDECANOIC ACID2,3-DIHYDROXYQUINOXALINE-6-CARBOXYLIC ACID2(2-Ethoxyethoxy)ethanolUrsodeoxycholic acid4-Amino-2,6-dichlorophenolpolyurethae finishes PUC seriesdefoaming agent OTDBT modified acrylic resin binder seriesCSF series modified sacrylic binderAC anti-fungus leather finishing agent2-Ethoxyethyl etherweather-proof acrylic binder series21-Iodo-16-methylpregna-1,4,9(11)-trien-17-ol-3,20-dioneN-Ethylmorpholine1,3-DIFLUORO-2-PROPANOLthickening agent PAS16-Methylpregna-1,4,9(11)-trien-17-ol-3,20-dione1-CHLORO-3-FLUOROISOPROPANOL2-(2-HEXYLOXYETHOXY)ETHANOLDisperse Yellow 1262,2'-OXYDIACETYL CHLORIDEpolyurethane water-based emulsion finishes PU-II seriesdiamfenetide Bis(2-butoxyethyl)etherDiethylene glycol dibenzoate
- Raw materialsETHYLENE OXIDE
- Diethylene glycol Poly(ethylene glycol) Dipropylene glycol N-phenyl-3-(trifluoromethyl)aniline N-(alpha,alpha,alpha-Trifluoro-m-tolyl)anthranilic acid 2-hydroxyethyl ester 2-[[3-(Trifluoromethyl)phenyl]amino]benzoic acid oxydi-2,1-ethanediyl ester Etofenamate Flufenamic acid ufenamate Diethylene glycol sesquiester of tall oil acid Titanium, diethylene glycol iso-Pr alc. triethanolamine aluminum complexes Diethylene glycol monobutyl ether formal DIETHYLENE GLYCOL DIISONONANOATE Glycerides, tallow mono-, hydrogenated, mixed esters with diethylene glycol and stearic acid DIETHYLENE GLYCOL DIETHYLHEXANOATE/DIISONONANOATE Castor oil, mixed esters with adipic acid, diethylene glycol and tall oil 1-BUTYL-3-METHYLIMIDAZOLIUM (DIETHYLENE GLYCOL MONOMETHYL ETHER) SULFATE DIETHYLENE GLYCOL ETHYL TERT.-BUTYL ETH&
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