The Essential Chemical Industry - online search Propene (Propylene) hy Propane (often known as propylene), like ethene, is a very Important bulding block for a large number of chemicals, including the addition polymer, poly(propene). However, unlike ethene, propene Undergoes substitution reactions, which lead to @ wide range of important chemicals, adiy yy, CHS HCH Uses of propene (propylene) soaps Crna, Figure The use of propane 1 afr 205,18 aie he Papin Qa Ari Chm Say 216 16 princpal uses of propene are to produce + polypropene) /polymers/oclyropene.ntmi polypropylene) + propenalfpelymersipolypropenoi-acid himltpropenal (acrolein) whichis oxdlzed to propence acid (acre acid) whieh, in turns used to make cele polymers + propenonitrie ipelymers/polypropencnitile emlfpropencnitil) (acrylate) which s the monomer for pelipropencnitile) cumene (chemicals/phencLhemlscumene} -methylethybenzene or iseprepylbenzene) which is then used to make phencl {ehemicasiphenok htm) and propanone (enemicalsfpropanene him (acetone + epaxypropane (propylene oxide) which Is used to make dials for che manufacture of palyurethanes (ipelymersipalyurethane.heml) and solvent ‘+ butanal eutrylaldenyde) and hence butancl, used asa solvent for surface coatings ‘The data given in Figure 1 are fr global production. However the dala vary ftom county to county. For example, the proportion used to make poy(propene) varios from only 88% in North America and 7% in Europe to 80% in te Mile East, The global proporion used to make ‘epoxypropane (/chemicalsipropene.himi#epoxypropane} (propene oxie) is 7% but 18% of te propene in Europe is usec to make the epoxide? 2 208, Prchemi ere Annual production of propene (propylene) [wors | 4 milon tonnes”Europe | 15 millon tonnes? us 3 milion tonnes 1 aor 205,15 Po Te rp Oana: me Manufacture of propene (propylene) Formany years, te overuhelming proporon of propene has Been manutd by we processes + steam cracking Uprocesses/crackng-somerisation-ang-reforming.tml#steam cracking) of naphtha + ctaltc cracking Uprocesses/racking-isomerisation-ane-refoeming.nimiWcat racking) of 835 ol Both processes also produce many other products, for example, ethene in large amounts. Howeve: amountof propene needed compared wit hat of elhene has increased and mulch research and development has concentaled con finding methogs of producing propene without elnene, These are known as OPP processes (On-purpose propane). There are now twee being used in significant amounts (0 Catalytic eracking Vprocessesieracking-somerisation-and-reforming himfeat_cracking) of propane Increasingly, propane s being catalytically cracked to form propene, using the same cat cracker (iprocessesieracking isomerisaton-and- reforming hmifcat_cracking) as that used fo crack gas ol Coy + CMe He Propane is being obiained in increasingly large amounts in the US ftom shale gas extracted by tacking Uprocessesiextacting-o-and-natural g9s-Facking himltracking), (i) The MTO (Methanol To Glens) Process (/materals-and-applcationsbiorefneries.NimlMTP._process) ‘Another process that has been developed is va methanol (eracuced fam biomass va synthesis gas), the MTP (Mathanol To Propane) process hich is an example of he MTO (Methanol Ta Olens) process. (Olotinis the older name forthe homologous sors, alkenes). Methanol can be converted into high purty ethene and propene via dimethyl ether. Methanol vapour is passed over alumina at ea 600 K. An equilibrium mixture of ‘methanel, dimethyl ether and stoam is produced, contaking about 25% methanol: 2CH,OH(g) = HxC—O-CHy(a) + 016) This moture of gases le then passed over a bed ofa zeoKke (iprocessesicataysis-h-ndusty nmHzeoKe) in aform that encourages high selectivity towards alkenes with numbers of eabon atoms Hom 2 108. However, by using @ Zeole treated with acid almost athe akene produced s propene, The propene is purtid by cooling ta @ liquid and then subjecting the Iqud to factional dstllaton, ‘This 2 similar process to that used to make hydrocarbons used in gasaline, the MTG (Methanolto Gasoline) process (ehemicalsimethanotntmi#NtTG), (i) Me reaction botwoon othone and butones ‘Another promising method is one fom etnene and butene: CH=CH + CH;CH=CHCHs —> 2CH:CH=CH» Boo-based ethene can be oblained by dehydration of bioethanol using a sicaalumina or alumina catalyst. The bulones (but--one and but2- ‘ene) can be produced by either dehyeraton of biobutanol(materias-and-applcatons/bitveks himibiobutanal or by dimerization of bioathene). The dimerization of evvene to but-t-ene fs cated out by passing heated ethene aver a zeolte impregnated with a ransiton metal complex. A variety of complexes of rhodium, tanium and other metas are used CH=CH, —> CHsCH2CH=CH2 [Amincure of ethene and butone is thon heated and passed over sold catalyst based on organic compounds of molybdenum(IV) and tungston(¥v (the Schrock calalysts) and organo-uthenium (I) compounds (te Grubbs cataysts), ina fxed-bed reactor /processesichemical- reactors htmfixed_bed): (CHa=CHe + CHsCH:CH=CH2 —» 2CHsCH=CHe ‘Smal amounts of coke are dapesitd on the catalyst and are removed from time lo time by passing hi|i 2010, steam cracking accounted for ca 56% and catalye cracking of gs ol for 37% of the global production. Much ofthe rest was made from the production of tom coal and rom the eracking of gas ol processesioracking-samerisation-and.zeforming himifeat_cracking) under vacuum. However, the new processes are being increasingly used and now account for some 15% of he propene produced and, wl is ‘expected, account in 2020 for about 25% of he propene being produced, wih steam cracking accounting for about 42% and racking about 33% 118i Pepe anders hres Cal Sats 216 Daf 205 ‘Another method of producing propens is va syngas and ethanol Synthesis gas (carbon monoxide and hydrogen} is used to convert biosthanol to propan-t-ot CHsCH.OH + CO + 2Hy —> CH:CH:CH:OH + H20 ‘The reaction s catalysed by arathenium-cobak complex sak. Amolybdenum-based catastis also being used as tis more resistant to poisoning by sultu-contaning impurtios i the feedstock, Subsequently, propan-t-olis dehysrated to propene: CHCH;CH:OH —> CHC! He + He Note on the chemistry of ethene (ethylene) and propene (propylene) fen Serta per WN Pomel Ny Al the C-Hbonds in ethene are very sttong and thus the majority of re ‘Smilary,propene has 3 stong C-H bonds and undergoes addon reactons (fer example, polymerization to palyipropene) and propene to ‘epoxypropans) tions invale additon tothe double bond, However, the C-H bonds in the methyl group are much weaker and propene has many reactons in which the double bond is preserved and the ‘methyl group undergoes substution reactions, or example ropononto Manfacture of epoxypropane (propylene oxide) Epoxypropane is manufactured nee main ways (0 By acing propene wi an aqueous soliton ofc fo frm a eur of -coroprpan (2%) and Zclropropert- 10%) poxypropar proven oxi) Yoms on adoro soon afethe sodium hyo orcaum here. For ramp on CHy-CHEGH, + Ch Hj0—» CH, -CH-CHECI + Her ‘OH m i CH, -CH-CH,C1 + OH —» H, —cH-CHs+ H,0+cr (i) By reactng propene wih a hydroperoxide such 1,1-imethylothyhyéroperoxide.Propone is pasted into Kau 1,1-dimethylethy| hydroperoxide Under pressure at about 400 K with a soluble molybdenum salt as catalyst: Hy Hs 0 Zh HyC-G-0-O-H + HyC-CHeCHy —e Hyo-C-0-H + Hoch oHe b dajmtrieoin ze! snmp (i) By acting propene wih nysrogen peroxds. New plants have been bul, agjacentto the plants producing propene, to manufacture large ‘quanties ofhycrogen peroxide (chemicalsIhydrogen-peroxide.htmifpropene). The peroxide reacts diecty with propene: fo} CH, CH=CH, +H,0, —> H,C—CH—CH,+H,0[Ahough hydrogen peroxide is expensive to produce, the large scale ofthe plant, coupled withthe lower costs associated wih the effuent means that this new process is very atractve Manufacture of butanal (butrylaldehyde) and butanol Butanal's produces by passing propene, carbon monoxide and hydrogen over a sold cobalt sa (a process known as the OXO process or hydroformylation} cHsch 2 Hy #CO +H, —e CHrCHyCHyc% H (The isomer of butanal, 2-methy-propana,(CHs),CHCHO, is also formed), Butanalis hydrogenated to butanol Date lat amended: 26th January 2017 (heptane ushitguinntac Aninvitation Wi invite you to wie tous ifyou have any specific comments about this ste, for example ‘errors that you have found, suggestions for new topics orforading ta the existing unis, ‘suggestions for Inks to other ses and addons or alternatives to cur examples. 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