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Soap&SoaplessDetergents

Soapismadeinachemicalreactionbetweenafatandanalkali.Thisreactionis

calledsaponification.Theproductsareglycerolandsoap:

calledsaponification.Theproductsareglycerolandsoap:

Nameslike‘sodiumtallowate’and‘sodiumpalmitate’aresoapsmadeinthis

reaction.‘Glycerin’isthesoap­maker’snameforglycerol.Thenameofthesoap

comesfromthefat.Fatmoleculescanbedrawninashapelikealetter‘E’.The

backboneoftheEismadefromthreecarbonatoms.Thethree‘sticks’oftheEare

longchainsofcarbonandhydrogenatoms.Thebackboneandsticksarejoined

togetherwithanoxygenatomlikethis:

togetherwithanoxygenatomlikethis:

The‘sticks’donotalwayshavethesamenumbersofcarbonatoms.Incoconutoil,

oftenusedtomakesoap,the‘sticks’canbesixdifferentlengths­8,10,12,14,16or

18carbonatoms.Eachhasadifferentname:

No.ofcarbonatoms

Name

8

Caprylic

10

Capric

12

Lauric

14

Myristic

16

Palmitic

18

Stearic

Thesenamesarenotthesystematicnamesthatchemistsuse.Theseare:

No.ofcarbonatoms

Name

8

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

bondswiththe‘backbone’,formingglycerol.Thesodiumparticlesmakenew

bondswiththecarbon/hydrogenchains,makingsoaps,likethis:

Thereactionisstartedwithsomeheat,usedtobreakthefirstbondsinthefat

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

(formulaCH3 ­CH=CH2 )acompoundfromdistillingcrudeoil.Acomplicatedseriesof

reactionsturnspropeneintoadetergent.Likesoap,detergentmoleculeshavealong

chainofcarbonandhydrogenatoms,butattheendofthemoleculethereisthis

group:

­SO3 ­ Na+ insteadofthe­COO­ Na+ 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.

Theothermajorsoapmakingprocessistheneutralizationoffattyacidswithanalkali.

Fatsandoilsarehydrolyzed(split)withahigh­pressuresteamtoyieldcrudefatty

acidsandglycerine.Thefattyacidsarethenpurifiedbydistillationandneutralized

withanalkalitoproducesoapandwater(neatsoap).

withanalkalitoproducesoapandwater(neatsoap).

Whenthealkaliissodiumhydroxide,asodiumsoapisformed.Sodiumsoapsare

"hard"soaps.Whenthealkaliispotassiumhydroxide,apotassiumsoapisformed.

Potassiumsoapsaresofterandarefoundinsomeliquidhandsoapsandshaving

creams.

Thecarboxylateendofthesoapmoleculeisattractedtowater.Itiscalledthe

hydrophilic(water­loving)

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.