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diethylene glycol

Product name diethylene glycol
Synonyms 2,2'-oxydiethanol
digol
(2-hydroxyethoxy)ethan-2-ol
3-oxa-1,5-pentanediol
diglycol
DEG
GOST 10136-77
CAS 111-46-6

Diethylene glycol (DEG) is a colorless, viscous, hygroscopic, odorless liquid with sweetish taste. It is fully miscible with water, lower alcohols, glycols, cellosolves, carbitols, acetone, chloroform and phenol. It is partly soluble in benzene, toluene, styrene, diethyl ether, carbon tetrachloride and phthalates. Mineral and natural oils are poorly soluble in diethylene glycol.

DEG is ethylene glycol ether. It possesses chemical properties both ethers and glycols. It can be esterified by acton of carboxylic acids or their anhydrides to form mono- and di- esters. It condences with carbonyl aldehydes and ketones to give cyclic acetals. Thus, reaction with acetone results in 2,2-dimethyl-1,3,6-trioxacyclooctane:

diethylene glycol condensation with carbonyl compounds


Diethylene glycol dehydrates in alkaline media to give 1,4-dioxane or tetraethylene glycol depending on reaction conditions. Interaction with ethylene oxide at 150-200°C results in polyethelene glycol with a good yield. This reaction accelerates by alkaline catalysts. It also reacts with ammonia under high temperature and pressure to form morpholine:

diethylene glycol reaction with ammonia


DEG is a toxic compound. The result of poisoning is central nervous system and kidney injury.

Production.

  • by interaction of monoethylene glycol (MEG) with ethylene oxide at 160-180°C with molar ratio ethylene oxide:MEG = 1:2. The reaction yield is about 60%:

    (CH2)2O + HOCH2CH2OH --> HOCH2CH2OCH2CH2OH

  • as a byproduct in MEG production by ethylene oxide hydration at 160-200°C and pressure 1-1.2MPa with molar ratio ethylene oxide:water = 1:10. Actually up to 15% of ethylene oxide is converted into diethylene glycol under these conditions.

    Uses.

    Diethylene glycol is applied:

  • as an intermediate in 1,4-dioxane, tetraethylene glycol, morpholine and other chemical products making;
  • as a feedstock in production of esters, polyurethanes, oligoesteracrylates, polyethyleneglycol maleinates and so on;
  • a humectant for tobacco, cork, printing ink, and glues;
  • as an intermediate in making of pharmaceiticals;
  • as a plasticizer for polyvinyl chloride (PVC) and other polymers;
  • as an effective agent for extraction of aromatic hydrocarbons from products of reforming process;
  • as a dehydration agent gor gases;
  • as a solvent for nitrocellulose, resins, dyes and some organic compounds;
  • as a coolant;
  • as a component of hydraulic and brake fluids;

  • Manufacturer(s) JSC "Nizhnekamskneftekhim" Inc.
    JSC Kazanorgsintez
    JSC Sibur-Neftehim
    Chemical structure of diethylene glycol

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