Ethylene Glycol

Base Information

• Chemical Name: Ethylene Glycol
• CAS No.: 107-21-1
• Deprecated CAS: 37221-95-7,71767-64-1,1371582-33-0,2088100-90-5,849688-22-8,71767-64-1
• Molecular Formula: C2H6O2
• Molecular Weight: 62.0684
• Hs Code.: 2905.31
• European Community (EC) Number: 203-473-3,920-413-8
• ICSC Number: 0270
• NSC Number: 155081,152325,152324,93876,57859,32854,32853
• UN Number: 3082
• UNII: FC72KVT52F
• DSSTox Substance ID: DTXSID8020597
• Nikkaji Number: J4.061D
• Wikipedia: Ethylene glycol
• Wikidata: Q194207
• NCI Thesaurus Code: C77464
• RXCUI: 1314364
• Metabolomics Workbench ID: 52011
• ChEMBL ID: CHEMBL457299
• Mol file: 107-21-1.mol

Synonyms:1,2 Ethanediol;1,2-Ethanediol;2 Hydroxyethanol;2-Hydroxyethanol;Ethylene Glycol;Glycol, Ethylene;Glycol, Monoethylene;Monoethylene Glycol

Chemical Property of Ethylene Glycol

Chemical Property:

• Appearance/Colour: clear, colorless syrupy liquid
• Vapor Pressure: 0.08 mm Hg ( 20 °C)
• Melting Point: -13 °C
• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 197.5 °C at 760 mmHg
• PKA: 14.22(at 25℃)
• Flash Point: 108.2 °C
• PSA: 40.46000
• Density: 1.097 g/cm³
• LogP: -1.02900
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: water: miscible
• Water Solubility.: miscible
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 62.036779430
• Heavy Atom Count: 4
• Complexity: 6

Purity/Quality:

≥99% ^*data from raw suppliers

1,2-EthyleneGlycol(EthyleneGlycol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-41
• Safety Statements: 26-39-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethylene Glycols
• Canonical SMILES: C(CO)O
• Recent ClinicalTrials: Evaluation of Fecal Microbiome Changes After Antegrade Continence Enema Placement and Initiation of Bowel Flush Regimen
• Recent EU Clinical Trials: Efficacy of a very low-volume Polyethylene Glycole (PEG 1L) bowel preparation vs. low-volume (2L) and high-volume (4L) PEG-based preparations. A randomized controlled study.
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract. The substance may cause effects on the kidneys, central nervous system and acid-base balance in the body. This may result in renal failure, brain injury and metabolic acidosis. Exposure could cause lowering of consciousness.
• Uses: Glycol is mainly used as the antifreeze agent for preparation of the automobile cooling systems and the raw material for the production of polyethylene terephthalate (the raw material of polyester fibers and plastics material). It can also be used for the production of synthetic resins, solvents, lubricants, surfactants, emollients, moisturizers, explosives and so on. Glycol can often used as alternative of glycerol and can often be used as hydration agent and solvent in the tanning industry and pharmaceutical industry. Glycol has a strong dissolving capability but it is easily to be oxidized to toxic metabolic oxalic acid and therefore can’t be widely used as a solvent. The ethylene glycol can be supplemented to the hydraulic fluid and can be used for preventing the erosion of oil-based hydraulic fluid on the rubber of the system; the water-based hydraulic fluid with ethylene glycol as a main component is an inflammable hydraumatic fluid and can be applied to the molding machine in aircraft, automobiles and high-temperature operation. There are many important derivatives of ethylene glycol. Low molecular weight polyethylene glycol (mono-uret ethylene glycol, bi-uret ethylene glycol, tri-uret ethylene glycol or respectively called as diethylene glycol, triethylene glycol, tetraethylene glycol) is actually the byproduct during the hydration of ethylene oxide B for preparation of ethylene glycol. Ethylene glycol is used as an antifreeze inheating and cooling systems (e.g., automobileradiators and coolant for airplane motors).It is also used in the hydraulic brake fluids;as a solvent for paints, plastics, and inks; as a softening agent for cellophane; and in themanufacture of plasticizers, elastomers, alkydresins, and synthetic fibers and waxes. Reagent typically used in cyclocondensation reactions with aldehydes1 and ketones1,2 to form 1,3-dioxolanes. Antifreeze in cooling and heating systems. In hydraulic brake fluids and de-icing solutions. Industrial humectant. Ingredient of electrolytic condensers (where it serves as solvent for boric acid and borates). Solvent in the paint and plastics industries. In the formulation of printers' inks, stamp pad inks, ball-point pen ink. Softening agent for cellophane. Stabilizer for soybean foam used to extinguish oil and gasoline fires. In the synthesis of safety explosives, glyoxal, unsatd ester type alkyd resins, plasticizers, elastomers, synthetic fibers (Terylene, Dacron), and synthetic waxes. To create artificial smoke and mist for theatrical uses.
• Production method: 1. Direct hydration of ethylene oxide is currently the only way for industrial-scale production of ethylene glycol. Ethylene oxide and water, under pressure (2.23MPa) and 190-200 ℃ conditions, and can directly have liquid-phase hydration reaction in a tubular reactor to generate ethylene glycol while being with byproducts diethylene glycol, tripropylene ethylene gl]ycol and multi-uret poly ethylene glycol. The dilute ethylene glycol solution obtained from the reaction further undergoes thin film evaporator condensation, and then dehydration, refinement to obtain qualified products and by-products. 2. sulfuric acid catalyzed hydration of ethylene oxide; ethylene oxide can react with water, in the presence of sulfuric acid as the catalyst, at 60-80 ℃ and pressure of 9.806-19.61kPa for hydration to generate ethylene glycol. The reaction mixture can be neutralized by liquid alkaline and evaporated of the water to obtain 80% ethylene glycol, and then distilled and concentrated in distillation column to obtain over 98% of the finished product. This method is developed in early time. Owing to the presence of corrosion, pollution and product quality problems, together with complex refining process, countries have gradually discontinued and instead change to direct hydration. 3. Direct ethylene hydration; directly synthesize ethylene glycol from ethylene instead of being via ethylene oxide. 4. dichloroethane hydrolysis. 5. Formaldehyde method. Industrial preparation of ethylene glycol adopts chlorine ethanol method, ethylene oxide hydration and direct ethylene hydration with various methods having their characteristics, as described below. Chlorohydrin method Take chloroethanol as raw materials for hydrolysis in alkaline medium to obtain it. The reaction is carried out at 100 ℃. First generate ethylene oxide. Then pressurize at 1.01 MPa pressure to obtain ethylene glycol. Ethylene oxide hydration Hydration of ethylene oxide contains catalytic hydration and direct hydration. The hydration process can be carried out under either normal pressure or under compression. Normal pressure method generally take a small amount of inorganic acid as catalyst for reaction at 50~70 ℃. Pressurized hydration had a high demand for the molar ratio of ethylene oxide over water which is higher than 1:6, to reduce the side reaction of producing the ether with the reaction temperature being at 150 °C and the pressure being 147kPa with hydration generating ethylene glycol. There are currently gas phase catalytic hydration with silver oxide being the catalyst and the alumina oxide being the carrier for reaction at 150~240 ℃ to generate ethylene glycol. Direct hydration of ethylene Ethylene, in the presence of catalyst (e.g., antimony oxide TeO2 with palladium catalyst) can be oxidized in acetic acid solution to generate monoacetate ester or diacetate ester with further hydrolysis obtaining the ethylene glycol. The above several methods takes ethylene oxide hydration as good with simple process and is suitable for industrialization.
• Description: Ethylene glycol was first synthesized in 1859; however, it did not become a public health concern until after World War II. In fact, the first published series of deaths from ethylene glycol consumption involved 18 soldiers who drank antifreeze as a substitute for ethanol. Despite the early recognition that patients who drank ethanol in addition to ethylene glycol had prolonged survival when compared to those drinking ethylene glycol alone, antidotal treatment of ethylene glycol toxicity with ethanol was not evaluated until the 1960s. Today, ethylene glycol poisoning continues to be a public health problem, particularly in the southeastern United States. In 2009, US poison control centers received 5282 calls about possible ethylene glycol exposures, and the toxicology community believes these exposures are underreported.

Technology Process of Ethylene Glycol

There total 920 articles about Ethylene 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: 98%

polyethylene terephthalate → disodium terephthalate (10028-70-3) + ethylene glycol (107-21-1)

Guidance literature:

With sodium hydroxide; In octanol; at 183 ℃; for 0.0833333h; Product distribution / selectivity;

Reference yield: 96%

polyethylene terephthalate → terephthalic acid (100-21-0) + ethylene glycol (107-21-1)

Guidance literature:

polyethylene terephthalate; With sodium hydroxide; In propan-1-ol; at 89 ℃; for 0.25h;

With hydrogenchloride; In propan-1-ol; water; Product distribution / selectivity;

Reference yield: 53.6%

cellulose (9004-34-6) → 1,2,3,4-butanetetrol (2319-57-5,2418-52-2,6968-16-7,7493-90-5,7541-59-5,10030-58-7,188346-77-2,149-32-6) + ethylene glycol (107-21-1)

Guidance literature:

With ruthenium-carbon composite; hydrogen; In water; at 215 ℃; for 1.5h; under 39003.9 Torr; Reagent/catalyst; Catalytic behavior; Autoclave;

DOI:10.1039/c6ra27524a

upstream raw materials:

oxirane

1,3-DIOXOLANE

[1,3]-dioxolan-2-one

glycerol

Downstream raw materials:

Tetraethylene glycol

diethylene glycol

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

2,2'-methanediyldioxy-bis-ethanol

Refernces

• 1、 Tian, Jingxia,Chen, Wei,Wu, Peng,Zhu, Zhirong,Li, Xiaohong. "Cu-Mg-Zr/SiO2 catalyst for the selective hydrogenation of ethylene carbonate to methanol and ethylene glycol". . p. 2624 - 2635. Retrieved 2018.
• 2、 Kaithal, Akash,H?lscher, Markus,Leitner, Walter. "Catalytic Hydrogenation of Cyclic Carbonates using Manganese Complexes". . p. 13449 - 13453. Retrieved 2018.
• 3、 Yang, Zhen-Zhen,Zhao, Ya-Nan,He, Liang-Nian,Gao, Jian,Yin, Zhong-Shu. "Highly efficient conversion of carbon dioxide catalyzed by polyethylene glycol-functionalized basic ionic liquids". . p. 519 - 527. Retrieved 2012.
• 4、 Esteve-Adell, Iván,Crapart, Bertrand,Primo, Ana,Serp, Philippe,Garcia, Hermenegildo. "Aqueous phase reforming of glycerol using doped graphenes as metal-free catalysts". . p. 3061 - 3068. Retrieved 2017.
• 5、 Miao,Zhu,Wang,Tan,Wang,Liu,Kong,Sun. "Efficient one-pot production of 1,2-propanediol and ethylene glycol from microalgae (Chlorococcum sp.) in water". . p. 2538 - 2544. Retrieved 2015.
• 6、 Cao, Yueling,Wang, Junwei,Kang, Maoqing,Zhu, Yulei. "Catalytic conversion of glucose and cellobiose to ethylene glycol over Ni-WO3/SBA-15 catalysts". . p. 90904 - 90912. Retrieved 2015.
• 7、 Li, Fengjiao,Wang, Liguo,Han, Xiao,He, Peng,Cao, Yan,Li, Huiquan. "Influence of support on the performance of copper catalysts for the effective hydrogenation of ethylene carbonate to synthesize ethylene glycol and methanol". . p. 45894 - 45906. Retrieved 2016.
• 8、 Wang, Luning,Menakath, Anjali,Han, Fudong,Wang, Yi,Zavalij, Peter Y.,Gaskell, Karen J.,Borodin, Oleg,Iuga, Dinu,Brown, Steven P.,Wang, Chunsheng,Xu, Kang,Eichhorn, Bryan W.. "Identifying the components of the solid–electrolyte interphase in Li-ion batteries". . p. 789 - 796. Retrieved 2019.
• 9、 Hanton, Martin J.,Tin, Sergey,Boardman, Brian J.,Miller, Philip. "Ruthenium-catalysed hydrogenation of esters using tripodal phosphine ligands". . p. 70 - 78. Retrieved 2011.
• 10、 Priebe, Jacks P.,Souza, Bruno S.,Micke, Gustavo A.,Costa, Ana C.O.,Fiedler, Haidi D.,Bunton, Clifford A.,Nome, Faruk. "Anion-specific binding to n-hexadecyl phosphorylcholine micelles". . p. 1008 - 1012. Retrieved 2010.