The Essential Chemical Industry - online Cig search te ei ® Epoxyethane (Ethylene oxide) Epoxyethane (ethylene oxide, EO) is a colourless gas at room temperature. The bonds inthe ring are easily broken so °. epoxyethane is very reactive. Ths, together with it being made directly from ethene (ethylene), a readily available feedstock, makes it an extremely important intermediate in the manufacture of many useful chemicals, \ Hc’—cH, Uses of epoxyethane (ethylene oxide) ‘The principal use of epoxyetrane isn the procucton of ethane-t,2-do, the principal consttuent of engine coolants, and in other dos the {1/CO}), which are used to make polyesters. These and other chemicals made ftom epoxyethane are dlscussed below. BZ eovervone anes 2 ‘Figure 4 Uses ofepoxythane a om may sore mn lb Prati, 216; Marketa Raa Conn. 206 Figur 1 shows th wore aes of epoxyetane By proportion. Butheve vary county by coun. For xampl ch a, by operon is Used nthe US to make the dl (41%) and mor is sed to make gyal ehars(10%).ethoxyaes (15%), thanclamines (18%) and povetiyene aoa (12% Annual production of epoxyethane (ethylene oxide) [wen [2+ miton tonnes? [asia_| 0.4 milion tonnes? Us, | 25 nition tonne Dao Matern ac Contin 218, Rage fr 202 2: psd rach 6 nr by 3018 Manufacture of epoxyethane (ethylene oxide)Ethene is mixed with airor oxygen and passed over a catalyst ely divided siver on an inert support such as alumina) at 620-550 K and under 16.20 atmospheres pressure (Figure 2). Two reactions, paral and complete oxidation, take place s:nukaneously at the catalyst surface, A small ‘amount of 12-dehloroethane is added tothe reaction mixture which decreases the unwanted side reaction to carbon dioxide and steam. Residence tein he reactors 1-4 seconds. ‘SWveris unique as a catalyst‘or this reacton but he mechanism isnot clear. The selectivity now being achieved is over 90%. As the catalyst ages, seleciy decreases. The Hetme of catalyst isin the range of -5 years 1402 9, H.C —'cH, hcxon, B® = 1007 kd me ‘rene 32. 200, +2H,0 BH? = 1300 4 met! ‘Figure 2 Two competing reactions forthe oxidation of ethane. (The entlpy values ar 523K and 45 atm) Reactions of epoxyethane (ethylene oxide) Production and uses of ethylene glycols Epoxyetnane is eactd wih walerunder neal or ace ondtons, to frm stepwise a range of products: ° nH;e —ch, + H,0 e n=? HO—CH,CH,0—H (wanseror ope) HO-CH,CH,O-CH,CH,0—H etme ao! HO—CH,CH,0—CH,CH,0—CH,CH,0—H nampene ae HO-(CH,CH,0),-H ayron gyeoPEG) Figure 3 Production of ethylene pico. When n= 1, the productis ethane-1,2-ol chemicalsethane-12diol.him) often known as monoethylene glycol) HOCH;CH,OH, used in engine coolants in heat ransfer fis, and for production of polyesters such as PET {/palymersipolyesters. him) (polyethylene terephthalate), When n= 2, the product is HOCH,CH,OCH,CH,OH, usualy krown as diatylane glycol tis used principally ta mab (ipolymersipolyurethane.him) and polyesters (pelymersipalyestersnim). Whon n= 3, the products used as a plaster (polymersipolymers-an-overviow.himbtilor polyurethanes Figure 4 Ebene. Uehemicateetrane 2am) and detyene glyco, Both ‘made rom epoxyetrane 2s wll «8 propanedl, are used ode Jee arr prior to takeoff in old conatons. I this phot, (he wings of an Air Cansce ‘Alrbus A320 are bong dolce. hd emus of eon (Pm Common When n =4 or more, the productis a poly(epoxyethane), known usually as polyethylene glycol (PEG). These are classified by relative molecular ‘mass, PEG200, PEG400, PEGEOO, alc and are used as nonionic surfactants (materals-and-applcationsisufacians.himlénonionic), syntetc ‘ubreants and soWents for pals, They are also in cosmetics and are used as plastelsers in adhesWes and prtng inks.Production and uses of glycol ethers and polyols Ciyeol eters and polyols ae made fom epoxyethane by eacting wih alcohols: Q nic —‘CHy + ROH —* HO~(CH2CH.0})-R Giycolethers produced wih n= 1 oF 2 and lower relatve molecular mass alechok are used as soWvents, Tivalnames are usually used for these ebiers Ethylone glycol monomethy| ether (methanol + 1 EO) and diethylene glycol monomethyl ether (metnanol-+ 2 EO) ae used as anteng addivos Injettuets \Where Ris fom a longer chain alcohol ang nis 3 or more, he products are known as ethoxylates. Alcohol ethoxyates, produced by reacting a rq Cys leone! with n=3 -10 molecules of EO, are widely used as nonionic surfactants (Imaterias-and-appleations/sutactans.himbinonionc) in allmanner of cloning applications. Ris rom a aol oro, the resulting polyals are used to make polyurethanes (/polmersipolyurthane.him). Production and uses of ethanolamines Ethanolamines are produced trom epoxyethane by reacton wih ammonia 2. a neni, nH, —cH, + NH <——» "MN ae t venen ctenen ‘They are used in textle fishing, cosmetics, soaps, detergents, gas purifcation (as bases, they react wih, and remove, hydrogen sulfide, carbon Gioxie and sulur dioxide) and corosion inhibitors. Diethanolamine is used in a new greener method of manufacturing the herbciée, ayphosale (materal-and-applcationsierop-protaction- choricas ntmitglyohosale) sol, or example, as "Roundup Date last amended: 6h November 2016 Uhre Aninvitation We invite you to wite tous fyou have any specific comments about this ste, fr example ‘errors that you have found, suggestions for new topice or for adding to the existing unis, suggestions for Inks to other ses and addons or alleratves to our examples. Please send these comments to: eci@essentatchemicalindusty.org(mailo:oci@essentalchemicalindusty org) ‘This web site is produced by the Centre for Industry Education Collaboration non-profit organization and an integral pat ofthe Department of Chemistry, University of York UK. Copyright © 2016 Universit f York Cente for Industry Education Collaboration, York, UK. All Rights Reserve,