Nitration of toluene: Reaction equation

Makhe sithethe ngendlela nitration of toluene. Izimasekile okufanayo ngokuhlanganisa inani elikhulu iimveliso semifinished ezisetyenziswayo xa kwenziwa imveliso neziqhushumbisi, namayeza afanelekileyo.

Ukubaluleka nitration

Benzene ahlobene njengoko iikhompawundi nitro enuka ziyafumaneka kwishishini kwemichiza mihla. Nitrobenzene in aniline yinto eliphakathi, iziqholo, imveliso amayeza. Yena i isinyibilikisi kakhulu iikhompawundi ezininzi organic, kuquka neselulosi kunye nayitrayithi ukwenza ubunzima gelatinous kunye naye. Xa neshishini le- petroleum oko isetyenziswa ocwenga yokuqaba-oyile. Xa nitration of toluene na benzidine uzilungiselele, aniline, aminosalicylic acid, phenylenediamine.

Iimpawu ze nitration

Nitration sachaza iqela NO2 eceleni kungena molecule organic ezimbaxa. Kuxhomekeka kumbandela eqala, le nqubo wabe nge impela, nucleophilic, indlela electrophilic. Amasuntswana esebenzayo benza njengoko ukuse- nitronium, ion kunye radicals NO2. Toluene nitration asabela libhekisela ilalela. Kuba kwezinye izinto eziphilayo ukuze kufakwe nitration, yaye kongezwe iqhina kabini.

Nitration of toluene kwindawo molecule ezizizembiwa enuka yenziwa usebenzisa nitrating acid (sulphuric acids nitric). Lo kuvala ebonisa izinto sulphuric acid ukukhonza njengoko inkqubo kuthetha vodotnimayuschego.

inkqubo equation

Nitration of toluene ibandakanya kufakwe elinye hydrogen atom yi nitro. njani icebo inkqubo eqhubekayo?

Ukuze ukuchaza nitration of toluene, lenxaki yokusabela kumelwa ngolu hlobo lulandelayo:

ArH + HONO2 + = Ar-NO2 + H2 O

It ikuvumela ukuba bagwetywe kuphela indlela jikelele ukuhlangana, kodwa angaxeli zonke iinkalo zale nkqubo. Enyanisweni kukho yokusabela phakathi hydrocarbon ibhedolaki imveliso nitric acid.

Njengoko imveliso unalo zinemoletyhule yamanzi, lunciphisa ndzo ka-nitric acid, nitration of toluene ke kusihla. Ukwenzela ukuphepha le ngxaki, le nkqubo yenziwa kumaqondo obushushu asezantsi usebenzisa nitric acid imali kwemfuneko.

Ukudityaniswa kwe-sulphuric acid njengoko arhente dehydrating esetyenzisiweyo , acetic acetic, polyphosphoric acid, boron trifluoride. Zenza snizat ukusetyenziswa kwe-nitric acid, ukwandisa ukusebenza yentsebenziswano.

Le bokuqonda inkqubo

Le nitration of toluene kuchazwa ekupheleni kwenkulungwane elinethoba V. Markovnikov. Wakwazi ukuseka unxibelelwano phakathi ubukho kwi umxube basabela becala sulphuric acid kunye nenkqubo bomyinge wamanzi. In mihla imveliso nitrotoluene anhydrous nitric acid ziyasetyenziswa, zithathwe in excess okungephi.

Ngaphezu koko, sulfonation kunye nitration of toluene kubandakanya ukusebenzisa ezikhoyo dehydrating boron ingxenye fluoride. intshayelelo yayo kwinkqubo indlela yenza ukunciphisa indleko imveliso efunyenweyo, nto leyo eyenza ikhona nitration of toluene. Inkqubo elibaleka equation ngokubanzi ngolu hlobo lulandelayo:

ArH + HNO3 + BF3 = Ar-NO2 + BF3 · H2 O

Emva kokugqitywa amanzi reaction yaziswa, apho monohydrate boron iifom fluoride dihydrate. Kuye isuswe vacuo, uze udibanise isi calcium fluoride, babuyele ifom compound yokuqala.

Ingakumbi nitration

Kukho ezinye iinkalo zenkqubo ezinxulumene ezikhethiweyo wezenzi, zeendawana usebenzisa indlela. Khawuqwalasele ezinye iindlela zabo ngaphezulu:

• 60-65 ekhulwini nitric acid xa kumxube 96 ekhulwini sulphuric acid;
• Umxube 98% nitric acid kunye sulphuric acid wamandla sokusabela izinto ezincinane eziphilayo;
• potassium Nitrate okanye I Ammonium ne-sulphuric acid wamandla - yinto ukhetho kakhulu ekuveliseni Polymer of iikhompawundi nitro.

Le kinetics of nitration

hydrocarbon enuka kamnandi, Ngokusebenza umxube sulphuric kunye acids nitric, nitro ionically. V. Markovnikov uyakwazi ukuchaza ingakumbi intsebenziswano. Le nkqubo ithatha kuqhubeka ngokwezigaba eziliqela. Nitrosernaya iasidi kuqala, leyo ivavanywa dissociation kwi isisombululo zolwelo. ion Nitronium ukuba wasabela ngokuba toluene ukwenza njenge nitrotoluene imveliso. Xa sifakwe umxube iimolekyuli zamanzi lwenzeka ngexesha deceleration.

Xa pende nendalo eziphilayo - nitromethane, acetonitrile, sulfolane - kuvumela ukusekwa zesiqinisekiso ukunyusa izinga nitration.

Oku kubangela nitronium zesiqinisekiso iqhotyoshelwe ngumongo enuka of toluene, ngaloo ndlela 'ukusekwa intermediate. Ngaphezu koko kukho umsantsa Proton, nto leyo nitrotoluene ukwakhiwa.

Ukuze ufumane inkcazelo eneenkcukacha yenkqubo eqhubekayo siya kuqwalasela ukuyilwa i "sigma" yaye "pi 'ezintsonkothileyo. Imfundo "kelly" ye zakhiwo linyathelo rate-umda intsebenziswano. Ireyithi asabela inxulumene ngqo wathandwa of nitronium zesiqinisekiso attachment kwi-atom carbon ngaphakathi kwinucleus iikhompawundi enuka kamnandi. Proton ukuqhekeka kude toluene lwenziwa zisonjululwe ngoko nangoko.

Kuphela kwezinye iimeko, kusenokuba kukho ezinye iingxaki kunye ukubuyisela kwindawo ekuyo neyayanyaniswa ephambili isiphumo Isotope entshukumo ezibalulekileyo. Oku kungenxa ekukhawuleziseni inkqubo yerhafu phambi nemiqobo ngeentlobo ezahlukeneyo.

Xa ukhetha kuvala kunye arhente dehydrating kunye kanzulu inkqubo acid sulphuric kukho utshintsho kuvuselele malunga nokusekwa iimveliso yokusabela.

isiphelo

It senziwa nitration of toluene nitrotoluene, nto leyo yimveliso oxabisekileyo lweshishini lemichiza. Yiyo le into yikhompawundi umonakalo, ngoko imfuno xa ugcinwa. Phakathi iingxaki ezinxulumene wokwenziwa mboni, qaphela ukusetyenziswa umyinge obonakalayo kwe-sulphuric acid wamandla.

Ukuhlangabezana nale ngxaki, ekhemisi afuna iindlela zokunciphisa sulphuric inkunkuma acid afunyenwe emva kwenkqubo nitration. Hi xikombiso, le nkqubo yenziwa kumaqondo obushushu asezantsi, lo eliphakathi esetyenziswayo ngokulula regenerable. Sulphuric acid uye iipropati oxidizing ngamandla, nto leyo kakubi ichaphazela umhlwa zesinyithi lwakukhula yingozi eziphilayo. Ukungqinelana yonke imigangatho yokhuseleko kunokwenzeka ukuba ukuhlangabezana nezi ngxaki, ukufumana iikhompawundi nitro kwizinga eliphezulu.