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

Ethylene glycol ^*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 and Industrial Applications: Ethylene glycol (EG) is commonly used as an antifreeze agent and a feedstock for the production of polyethylene terephthalate, which is utilized in bottles and packaging materials. Its widespread application across industries underscores its importance as a versatile chemical compound.
• Market Overview and Applications: The EG market is projected to experience rapid expansion, with an expected value surpassing USD 61.7 billion by 2031. This growth is driven by the booming plastic industry, particularly in packaging applications where EG serves as a platform chemical for polyethylene terephthalate (PET). EG is also utilized as a solvent, antifreeze, and anti-icer in the automotive and aviation industries. Saudi Arabia, the United States, and Kuwait are among the leading producers of EG.
• Chemical Composition and Production: Ethylene glycol (EG) is a 1,2-glycol compound produced by the reaction of ethylene oxide with water. It is classified as a glycol and an ethanediol. The primary commercial process for EG production involves the direct oxidation of petroleum-based ethylene to obtain ethylene oxide, followed by the hydration of ethylene oxide to produce EG. Alternatively, EG can be synthesized from dimethyl oxalate (DMO) through hydrogenation over precious metal palladium catalysts at high pressures.
• Renewable Sources and Sustainability: There is increasing awareness regarding sustainable development and raw material security, leading to the exploration of innovative pathways for EG production from renewable sources. Bio-based EG synthesis reduces dependence on petroleum and potentially decreases carbon footprint. Plant biomass, consisting of cellulose, hemicellulose, and lignin, is a widely available and cost-effective feedstock for bio-EG production.
• Biological Pathways for EG Synthesis: Microorganisms such as yeast, bacteria, and mold are employed in the biological conversion of carbon-rich intermediates into ethanol. This biochemical process is conducted at low temperatures, with ethanol subsequently dehydrated to form bio-ethylene. Bioethylene undergoes similar processing steps as petroleum-based ethylene for EG production. Feedstocks for bio-ethanol production include corn starch, sugarcane, and wheat starch.
• Bulk Production and Synthesis Routes: EG is considered a bulk chemical, with an annual production of approximately 57 million metric tonnes. Apart from conventional synthesis from ethylene oxide, EG can also be synthesized from syngas via dimethyl oxalate as an intermediate. These various synthesis routes contribute to the versatility and availability of EG for diverse industrial applications.

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: 98.0%

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: 96.0%

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.