H H298.15= A*t + B*t2/2 + ; Tilton, V.V., Eng. Uses of ethylene oxide Ethylene oxide is used as a chemical intermediate in the production of various. Ideal gas thermodynamic properties of oxygen heterocyclic compounds. For a cleaner product, the reaction is conducted in the gas phase or in an organic solvent. mono-ethylene glycol, di-ethylene glycol and other poly-ethylene glycols) get unavoidably produced. Here, water is used as the scrubbing media which scrubs away majority of ethylene oxide along with some amounts of CO2, N2, CH2=CH2, CH4 and aldehydes (introduced by the recycle stream). ; Add a few grams of aluminum oxide to the test tube, but don't submerge it in the ethanol. J. Chem. Ethylene oxide generally acts as its own cathartic; however, if deemed necessary, excretion may be promoted by administering a saline cathartic or sorbitol to conscious and alert victims. [all data], Crog and Hunt, 1942 Volume III, Volumetric Behaviour and Thermodynamic Properties of Ethylene Oxide, Fire suppression is reached only upon dilution with water above 22:1. When ethylene oxide is scrubbed from the recycle gas with an aqueous solution, ethylene glycols (viz. AC - William E. Acree, Jr., James S. Chickos Ethylene oxide readily reacts with aqueous solutions of hydrochloric, hydrobromic and hydroiodic acids to form halohydrins. Am. Then reaction is carried out in a special insulated reactor in an inert atmosphere (nitrogen) to prevent a possible explosion of ethylene oxide. J. [130][131] Ethylene oxide is classified as a class 2 carcinogen by the German MAK commission and as a class A2 carcinogen by the ACGIH. Acta, 1992, 194, 9-46. Part 1. Data Program, but require an annual fee to access. S = A*ln(t) + B*t + C*t2/2 + D*t3/3 Ethylene Oxide - Hazards and Methods of Handling., Press, Tokyo, 1981. Your institution may already be a subscriber. Die photoionenspektren der Isomeren propylen-cyclopropan und acetaldehyd-athylenoxyd, Chao J., [all data], Hess and Tilton, 1950 transition temp Tm 65 C density 1.21 g/mL at 25 C Coles, K.F. mol wt average Mv ~4,000,000 (nominal) contains <1000 ppm BHT as inhibitor 100-1000 ppm BHT as inhibitor viscosity 1,650-5,500 cP, 1 % in H2O (25 C, Brookfield) (lit.) [all data], Giauque and Gordon, 1949, 3 [all data], Moureu and Dode, 1937 The yield of ethylene oxide is about 80% of the theoretical value; for 1 tonne (0.98 long tons; 1.1 short tons) of ethylene oxide, about 200kg (440lb) of ethylene dichloride is produced. Proton affinities photoelectron spectra of three-membered-ring J. Heterocycl. It is miscible with water, alcohol, and most organic solvents and soluble in acetone. McDonald, R.A.; Shrader, S.A.; Stull, D.R., Ref. Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Dorofeeva O.V., Similarly proceed the reactions with primary and secondary amines: Dialkylamino ethanols can further react with ethylene oxide, forming amino polyethylene glycols:[19], Trimethylamine reacts with ethylene oxide in the presence of water, forming choline:[36]. [137], Because the odor threshold for ethylene oxide varies between 250 and 700 ppm, the gas is already at toxic concentrations when it can be smelled. Phys., 1969, 51, 52. Ramasamy R., [65] This more efficient routine accounted for about half of ethylene oxide production in the 1950s in the US, and after 1975 it completely replaced the previous methods. View plot K. See also. The chlorohydrin process was unattractive for several reasons, including low efficiency and loss of valuable chlorine into calcium chloride. Am. [all data], Bieri, Asbrink, et al., 1982 Data from animal studies indicate two possible pathways for the metabolism of ethylene oxide: hydrolysis to ethylene glycol and glutathione conjugation to form mercapturic acid and meththio-metabolites. Ethylene oxide is a colourless gas at standard room temperature and pressure. A general reaction search In 2009, demand is estimated to have declined to about 5.2Mt (5.7million short tons). [all data], Domalski and Hearing, 1996 IUPAC Standard InChI: IUPAC Standard InChIKey:IAYPIBMASNFSPL-UHFFFAOYSA-N. CAS Registry Number: Chemical structure: This structure is also available as a 2d Mol file 3d SD file The 3d structure may be viewed using. I. Refraction & dispersion of hydrocarbon aldehydes, ketones, acids & esters with i pair of conjug. [all data], Aue, Webb, et al., 1975 Phys. Vapor pressure. J. Chem. also available. [109], Ethylene oxide is used as a fungicide and as an accelerator of maturation of tobacco leaves. J. Chim. Ethylene fluorohydrin is obtained differently, by boiling hydrogen fluoride with a 56% solution of ethylene oxide in diethyl ether. [all data], Go To: Top, Gas phase thermochemistry data, References. Part 2. Molecular weight: 44.0526 IUPAC Standard InChI: InChI=1S/C2H4O/c1-2-3-1/h1-2H2 IUPAC Standard InChIKey: IAYPIBMASNFSPL-UHFFFAOYSA-N CAS Registry Number: 75-21-8 Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file The 3d structure may be viewed using Java or Javascript . Uncertainty assigned by TRC = 0.6894 bar; Uncertainty assigned by TRC = 0.7584 bar; Uncertainty assigned by TRC = 0.23 mol/l; Based on data from 239. ; Gordon, J., [92] Dow METEOR (Most Effective Technology for Ethylene Oxide Reactions) is an integrated technology for producing ethylene oxide and its subsequent hydrolysis into ethylene glycol. The gas has a characteristic sweet odor of ether, noticeable when its concentration in air exceeds 500ppm. The catalyst packed in these tubes is in the form of spheres or rings of diameter 3 to 10mm (0.12 to 0.39in). [all data], Timmermans and Hennaut-Roland, 1937 Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. [112] Several industrial accidents have been attributed to ethylene oxide explosion.[113][114][115]. [51] Cationic polymerization of ethylene oxide is assisted by protic acids (HClO4, HCl), Lewis acids (SnCl4, BF3, etc. The use of alkaline catalysts may lead to the formation of polyethylene glycol: Reactions with alcohols proceed similarly yielding ethylene glycol ethers: Reactions with lower alcohols occur less actively than with water and require more severe conditions, such as heating to 160C (320F) and pressurizing to 3MPa (440psi) and adding an acid or alkali catalyst. McDonald, R.A.; Shrader, S.A.; Stull, D.R., In view of these insidious properties, continuous electrochemical monitoring is standard practice, and it is forbidden to use ethylene oxide to fumigate building interiors in the EU and some other jurisdictions.[138]. Chem. Phys., 1940, 8, 618-622. Its excess energy is about 355.6 kJ/mol, which exceeds by 29.3 kJ/mol the binding energy of the C-C bond in acetaldehyde. ; Popper, Felix, [77], According to Merck Life Science UK 2020 Safety Data Sheet provided to the European Chemicals Agency's Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH)a 2006 European Union regulation,[140] ethylene oxide is "presumed to have carcinogenic potential for humans."[8]. Stephenson, Richard M.; Malanowski, Stanislaw, Lowrey, A., III; Watanabe, K., and Informatics, Vibrational and/or electronic energy levels, Computational Chemistry Comparison and Benchmark Database, NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data), p=1 bar. [13] [14] [26] form is Vapor pressure. Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 I. Refraction & dispersion of hydrocarbon aldehydes, ketones, acids & esters with i pair of conjug. Reasons for the sex specificity of this effect are not known. Chem. In addition to the Thermodynamics Research Center Among glycols, ethylene glycol is used as antifreeze, in the production of polyester and polyethylene terephthalate (PET raw material for plastic bottles), liquid coolants and solvents. Also, a small proportion of the gas leaving the ethylene oxide scrubber (0.10.2%) is removed continuously (combusted) to prevent the buildup of inert compounds (N2, Ar, and C2H6), which are introduced as impurities with the reactants. Soc., 1922, 44, 8, 1709-1728, https://doi.org/10.1021/ja01429a013 Spectrochemical studies. Database and to verify that the data contained therein have At steady state, 20-25% of inhaled ethylene oxide reaching the alveolar space is exhaled as unchanged compound and 75-80% is taken up by the body and metabolized. Eng. Eng. Office of Data and Informatics. Wilhoit, R.C. Dehydrochlorination of 2-chloroethanol, developed by Wurtz in 1859, remains a common laboratory route to ethylene oxide: The reaction is carried out at elevated temperature, and beside sodium hydroxide or potassium hydroxide, calcium hydroxide, barium hydroxide, magnesium hydroxide or carbonates of alkali or alkaline earth metals can be used. 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