Soap&SoaplessDetergents

Soapismadeinachemicalreactionbetweenafatandanalkali.Thisreactionis
calledsaponification.Theproductsareglycerolandsoap:

Nameslikesodiumtallowateandsodiumpalmitatearesoapsmadeinthis
reaction.Glycerinisthesoapmakersnameforglycerol.Thenameofthesoap
comesfromthefat.FatmoleculescanbedrawninashapelikealetterE.The
backboneoftheEismadefromthreecarbonatoms.ThethreesticksoftheEare
longchainsofcarbonandhydrogenatoms.Thebackboneandsticksarejoined
togetherwithanoxygenatomlikethis:

Thesticksdonotalwayshavethesamenumbersofcarbonatoms.Incoconutoil,
oftenusedtomakesoap,thestickscanbesixdifferentlengths8,10,12,14,16or
18carbonatoms.Eachhasadifferentname:
No.ofcarbonatoms

Name

Caprylic

10

Capric

12

Lauric

14

Myristic

16

Palmitic

18

Stearic

Thesenamesarenotthesystematicnamesthatchemistsuse.Theseare:
No.ofcarbonatoms

Name

octan

10

decan

12

dodecan

14

tetradecan

16

hexadecan

18

octadecan

Thealkali
Thealkaliissodiumhydroxide,formulaNaOH.Therearemillionsofsodiumand
hydroxideparticlesinonesmallgranuleofsolidsodiumhydroxidealwaysina1:1
ratio.Theseparticlesarepositivelyandnegativelychargedandarecalledions.The
sodiumhydroxidestructureisformedbecausetheoppositelychargedparticles
attracteachother.Thesodiumandhydroxideparticlesseparatewhenaddedto
water,makingasolution.Sodiumhydroxideisalsocalledlye,meaninglatheror
batheinLatin.Itisalsocalledcausticsoda.

Thesaponificationreaction
Inthereaction,thefatmoleculebreaksup.Thehydroxideparticlesmakenew
bondswiththebackbone,formingglycerol.Thesodiumparticlesmakenew
bondswiththecarbon/hydrogenchains,makingsoaps,likethis:

Thereactionisstartedwithsomeheat,usedtobreakthefirstbondsinthefat
molecules.Energyisreleasedwhenthenewbondsaremade.Thereactionis
exothermicbecausetheenergyrequiredtobreakthebondsislessthatthanthe
energyreleasedwhenthenewbondsform.Fatmoleculesarelargeanddonot
moveveryquickly,ormixeasilywithwater,soittakestimeforthereactantstomeet.
Thisiswhystirringandtimeisneededtomakesoap.Thereactiongoesonafterthe
soapispouredintomoulds.Givingittimetostopiscalledcuring.Thismakessure
thereisnosodiumhydroxideleftoverwhichcoulddamageskin.
Soaplessdetergents
Whenasoapisusedinhardwater,asolidsubstancewecallscumforms.Thisis
becausechargedcalciumandmagnesiumparticles(calledions)presentinthe
waterreactwithsoaptoformaninsolublesubstance.Scumbuildsuponclothes,
bathsandsinks.Detergentsdonotformscum.Theyaremadefrompropene
(formulaCH3CH=CH2)acompoundfromdistillingcrudeoil.Acomplicatedseriesof
reactionsturnspropeneintoadetergent.Likesoap,detergentmoleculeshavealong

chainofcarbonandhydrogenatoms,butattheendofthemoleculethereisthis
group:
SO3Na+insteadoftheCOONa+grouppresentinsoap.
Thisdifferencestopsscumforming.Whenscumforms,sodiumisreplacedwitha
calciumormagnesiumparticle.Thenewsubstance,scum,doesnotdissolvein
water.Whenacalciumormagnesiumparticlereactswithadetergentmolecule,the
newsubstancedoesdissolveinwater,sothereisnoscum.
Problemswithsoaplessdetergents
Whenasoapsolutioniswashedaway,thesoapmoleculesbreakupintosmaller
moleculescontainingcarbon,hydrogenandoxygenatoms.Thesegobackintothe
soilandaretakenupbyplantsandmicroorganisms.Detergentsbreakdownina
similarway,buttakemuchlonger.Thisiswhyfoamissometimesseenonriversand
streamsthedetergentmoleculeskeeptheirpropertiesmuchlongerthansoap.
Althoughdetergentsaregoodatremovinggreaseanddirt,theycanalsoirritateand
dryouttheskin.Somepeoplearesensitivetodetergentsandmayhaveskin
reactionswhenusingproductswhichcontainthem.

Soaps
Soapsarewatersolublesodiumorpotassiumsaltsoffattyacids.Soapsaremade
fromfatsandoils,ortheirfattyacids,bytreatingthemchemicallywithastrongalkali.
HowSoapsareMade
Saponificationoffatsandoilsisthemostwidelyusedsoapmakingprocess.This
methodinvolvesheatingfatsandoilsandreactingthemwithaliquidalkalito
producesoapandwater(neatsoap)plusglycerine.


Theothermajorsoapmakingprocessistheneutralizationoffattyacidswithanalkali.
Fatsandoilsarehydrolyzed(split)withahighpressuresteamtoyieldcrudefatty
acidsandglycerine.Thefattyacidsarethenpurifiedbydistillationandneutralized
withanalkalitoproducesoapandwater(neatsoap).

Whenthealkaliissodiumhydroxide,asodiumsoapisformed.Sodiumsoapsare
"hard"soaps.Whenthealkaliispotassiumhydroxide,apotassiumsoapisformed.
Potassiumsoapsaresofterandarefoundinsomeliquidhandsoapsandshaving
creams.
Thecarboxylateendofthesoapmoleculeisattractedtowater.Itiscalledthe

hydrophilic(waterloving)

end.Thehydrocarbonchainisattractedtooilandgreaseandrepelledbywater.Itis
knownasthehydrophobic(waterhating)end.
HowWaterHardnessAffectsCleaningAction
Althoughsoapisagoodcleaningagent,itseffectivenessisreducedwhenusedin
hardwater.Hardnessinwateriscausedbythepresenceofmineralsaltsmostly
thoseofcalcium(Ca)andmagnesium(Mg),butsometimesalsoiron(Fe)and
manganese(Mn).Themineralsaltsreactwithsoaptoformaninsolubleprecipitate
knownassoapfilmorscum.
Soapfilmdoesnotrinseawayeasily.Ittendstoremainbehindandproducesvisible
depositsonclothingandmakesfabricsfeelstiff.Italsoattachestotheinsidesof
bathtubs,sinksandwashingmachines.
Somesoapisusedupbyreactingwithhardwatermineralstoformthefilm.This
reducestheamountofsoapavailableforcleaning.Evenwhenclothesarewashedin
softwater,somehardnessmineralsareintroducedbythesoilonclothes.Soap
moleculesarenotveryversatileandcannotbeadaptedtotoday'svarietyoffibers,
washingtemperaturesandwaterconditions.