Their method is rather flexible with regard to the specific requirements of specific industries; it is characterized by high selectivity with respect to the ethylene oxide product and long lifetime of the catalyst (3 years). The reaction is catalyzed by acidic or basic catalysts. Molecular weight calculation: 12.0107*2 + … Kieran O’Donnell, Adrian Boyd, Brian J. Meenan, Controlling Fluid Diffusion and Release through Mixed-Molecular-Weight Poly(ethylene) Glycol Diacrylate (PEGDA) Hydrogels, Materials, 10.3390/ma12203381, 12, 20, (3381), (2019). The production of polyethylene glycol was first reported in 1859. The main advantage of the process is relative simplicity, using fewer stages and less equipment. Although not yet in commercial production, many groups around the globe are engaged in research on solid polymer electrolytes involving PEG, with the aim of improving their properties, and in permitting their use in batteries, electro-chromic display systems, and other products in the future. By-products include acetaldehyde (due to isomerization). In the United States, the operation of EtO sterilization is overseen by the EPA through the National Emission Standard for Hazardous Air Pollutants. The produced ethylene oxide is purified by rectification. Molecular Weight: 146.23. UNII-9O691KKR2A. Poly(ethylene glycol) analogs grafted with low molecular weight poly(ethylene imine) as non-viral gene vectors 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). Polyethylene oxide, or high-molecular weight polyethylene glycol, is synthesized by suspension polymerization. [clarification needed] Peripheral neuropathy, impaired hand-eye coordination and memory loss have been reported in more recent case studies of chronically-exposed workers at estimated average exposure levels as low as 3 ppm (with possible short-term peaks as high as 700 ppm). 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 160 °C (320 °F) and pressurizing to 3 MPa (440 psi) and adding an acid or alkali catalyst. [72], Whereas oxidation by air is still being used, oxygen (> 95% purity) is preferred for several reasons, such as higher molar yield of ethylene oxide (75–82% for oxygen vs. 63–75% for air), higher reaction rate (no gas dilution) and no need of separating nitrogen in the reaction products.[17][73]. A 2003 study of 7,576 women exposed while at work in commercial sterilization facilities in the US suggests ethylene oxide is associated with breast cancer incidence. The reaction is catalyzed by magnesium-, aluminium-, or calcium-organoelement compounds. 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. The reduction catalysts include mixtures of zinc dust and acetic acid, of lithium aluminium hydride with titanium trichloride (the reducing agent is actually titanium dichloride, formed by the reaction between LiAlH4 and TiCl3) and of iron(III) chloride with butyllithium in tetrahydrofuran.[46]. [68], Older factories typically use air for oxidation whereas newer plants and processes, such as METEOR and Japan Catalytic, favor oxygen.[70]. Empirical Formula (Hill Notation): C18H20N2O12. It is coupled to hydrophobic molecules to produce non-ionic surfactants. ethylene glycol bis(3-mercaptopropionate) ... Molecular Weight: 238.3 g/mol. Formally, the direct oxidation process is expressed by the following equation: However, significant yield of carbon dioxide and water is observed in practice, which can be explained by the complete oxidation of ethylene or ethylene oxide: The process of heterogeneous catalytic oxidation of ethylene was studied by P. A. Kilty and W. M. H. Sachtler, who suggested the following mechanism:[71]. PEGs and methoxypolyethylene glycols are manufactured by Dow Chemical under the trade name Carbowax for industrial use, and Carbowax Sentry for food and pharmaceutical use. [131] A 2004 follow up study analyzing 18,235 men and women workers exposed to ethylene oxide from 1987 to 1998 concluded "There was little evidence of any excess cancer mortality for the cohort as a whole, with the exception of bone cancer based on small numbers. [66], Next, aqueous solution of ethylene chlorohydrin enters the second column, where it reacts with a 30% solution of calcium hydroxide at 100 °C (212 °F):[66]. [109], Gas chromatography is the principal method for analysis and detection of ethylene oxide.[77]. Even then, the odor of ethylene oxide is sweet, aromatic, and can easily be mistaken for the pleasant aroma of diethyl ether, a common laboratory solvent of very low toxicity. Headache, nausea, and vomiting have been reported. PEGs are liquids or low-melting solids, depending on their molecular weights. [24] Ethylene oxide is readily soluble in water, ethanol, diethyl ether and many organic solvents. Modern plants producing ethoxylates are usually based on the BUSS LOOP reactors technology,[95] which is based on a three-stage continuous process. Uses advised against Not for food, drug, pesticide or biocidal product use Details of the supplier of the safety data sheet For a cleaner product, the reaction is conducted in the gas phase or in an organic solvent. [99], The direct use of ethylene oxide accounts for only 0.05% (2004 data) of its global production. [41], Reaction of ethylene oxide with sulfur dioxide in the presence of caesium salts leads to the formation of an 11-membered heterocyclic compound which has the complexing properties of crown ethers:[42], When heated to about 400 °C (750 °F), or to 150–300 °C (300–570 °F) in the presence of a catalyst (Al2O3, H3PO4, etc. 2005-03-27. The catalyst packed in these tubes is in the form of spheres or rings of diameter 3 to 10 mm (0.12 to 0.39 in). Positive exposure-response trends for lymphoid tumors were found for males only. Polyethyleneglycols are used in perfumes, cosmetics, pharmaceuticals, lubricants, paint thinners and plasticizers. [62] More efficient direct oxidation of ethylene by air was invented by Lefort in 1931 and in 1937 Union Carbide opened the first plant using this process. PEG is soluble in water, methanol, ethanol, acetonitrile, benzene, and dichloromethane, and is insoluble in diethyl ether and hexane. Also, a small proportion of the gas leaving the ethylene oxide scrubber (0.1–0.2%) is removed continuously (combusted) to prevent the buildup of inert compounds (N2, Ar, and C2H6), which are introduced as impurities with the reactants. Depending on the catalyst type, the mechanism of polymerization can be cationic or anionic. The autoignition temperature is 429 °C (804 °F), decomposition temperature of 571 °C (1,060 °F) at 101.3 kPa (14.69 psi), minimum inflammable content in the air is 2.7%,[115] and maximum limit is 100%. The main advantage of the process is production of pure ethylene glycol without the need for further purification. (23 April 1935) "Process for the production of ethylene oxide". [98], Addition of hydrocyanic acid to ethylene oxide is carried out in the presence of a catalyst (sodium hydroxide and diethylamine), and dehydration of cyanohydrin occurs in the gas phase upon the catalytic action of aluminium oxide. [121], The company was, until the time of the explosion the only producer of ethylene oxide in Spain with an installed capacity of 140,000 tons/year. Ethylene oxide can further be oxidized, depending on the conditions, to glycolic acid or carbon dioxide: Deep gas-phase reactor oxidation of ethylene oxide at 800–1,000 K (527–727 °C; 980–1,340 °F) and a pressure of 0.1–1 MPa (15–145 psi) yields a complex mixture of products containing O2, H2, CO, CO2, CH4, C2H2, C2H4, C2H6, C3H6, C3H8 and CH3CHO.[47]. [118][119] The accident launched substantial debris over a radius of about two and a half kilometers, one piece penetrating a distant home and killing an occupant. To maintain this temperature, the cooling system of the reactor plays a vital role. ›› Ethylene Glycol molecular weight. [67], Union Carbide (currently a division of Dow Chemical Company) was the first company to develop the direct oxidation process.[68]. Ethylene glycol is 17.93M. Finally, the reaction mixture is neutralized, degassed and purified. Mw and Mn can be measured by mass spectrometry. High concentrations can cause pulmonary edema and damage the cardiovascular system; the damaging effect of ethylene oxide may occur only after 72 hours after exposure. Section 4. Carbowax, GoLYTELY, GlycoLax, Fortrans, TriLyte, Colyte, Halflytely, Except where otherwise noted, data are given for materials in their. 3 Chemical and Physical Properties Expand this section. Lefort, T.E. Poly(ethylene glycol)s with the average molecular weight of 200, 400, 600, 1500, 4600 and 8000 were obtained from Sigma-Aldrich Inc.1-butanol was bought from Tianjin Bodi chemical engineering Co. Ltd. CO 2 and N 2 used for gas permeation test were of research grade ( > 99.9% pure), and they were supplied from Dalian Gas Company. [111] A number of industrial accidents have been attributed to ethylene oxide explosion.[112][113][114]. Macrogol, MiraLax, GoLytely, Colace used as a laxative, is a form of polyethylene glycol. [10][11][108], Ethylene is used in the synthesis in 2-butoxyethanol, which is a solvent used in many products. DTXSID40583948 (~13~C_2_)Ethane-1,2-diol. [75] This places ethylene oxide 14th most produced organic chemical, whereas the most produced one was ethylene with 113 Mt (125 million short tons). [133] The metabolism of ethylene oxide is not completely known. Molecular Weight : 62.07 g/mole . The chlorohydrin process was unattractive for several reasons, including low efficiency and loss of valuable chlorine into calcium chloride. Half of that production was used to manufacture ethylene glycol for PET production. Ethylene oxide is one of the most important raw materials used in large-scale chemical production. All three ethanolamines are produced in the process, while ammonia and part of methylamine are recycled. The final product of the reaction is a primary alcohol: Similar mechanism is valid for other organometallic compounds, such as alkyl lithium: Ethylene oxide easily reacts with hydrogen cyanide forming ethylene cyanohydrin: A slightly chilled (10–20 °C) aqueous solution of calcium cyanide can be used instead of HCN:[36]. Those steps are carried continuously. PEG-2 Dilaurate. [122] The accident will be investigated under EU regulations within the context of the European Agency for Safety and Health at Work, In September 2020, high-level of pesticides were found in 268 tonnes of sesame seeds from India. [106] It relies on the use of a flexible sterilization chamber and an EtO cartridge for small volume sterilization, and where environmental and/or portability considerations dictate the use of a low dose. 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