Nitration ka toluene: Reaction kwesibalo

Ake sixoxe indlela nitration ka toluene. Njengoba yenziwe ngendlela efanayo ngo-ukusabela lenqwaba imikhiqizo semifinished asetshenziswe ekukhiqizeni lokubanjwa neziqhumane, imithi.

Ukubaluleka nitration

Benzene nemikhiqizo njengoba elimnandi nitro compounds ziyatholakala ku yesimanje amakhemikhali umkhakha. Nitrobenzene e aniline umkhiqizo Lesisemkhatsini, amakha, ukukhiqizwa ezithaka imithi. He is an kuphela esihle kakhulu compounds eziningi organic, kuhlanganise i-cellulose kanti nitrite ukwakha mass gelatinous naye. Esikhathini umkhakha petroleum isetshenziswa njengendlela purifier for lubricating amafutha. Lapho nitration ka toluene kuyinto benzidine lelungiselelwe, aniline, aminosalicylic acid, phenylenediamine.

Izimpawu nitration

Nitration libhekene itheku NO2 iqembu engqamuzaneni we kwakwakhe organic. Kuye indaba kokuqala, le nqubo wabe nge olukhulu, nucleophilic, indlela electrophilic. I izinhlayiya asebenzayo ukwenza njenge nitronium cations, ion futhi ezizivelelayo NO2. Toluene nitration ukuphendula libhekisela esikhundleni. Ukuze uthole ezinye izinto eziphilayo zingase esikhundleni nitration, kanye kwalokho isibopho double.

Nitration ka toluene e-molecule ye-hydrocarbon elimnandi Kwenziwa usebenzisa nitrating acid (sulfuric futhi acid nitric). I kulethe liveza izindawo sulfuric acid ukukhonza njengoba inqubo isho vodotnimayuschego.

inqubo kwesibalo

Nitration ka toluene kuhilela esikhundleni esisodwa hydrogen atom ngu nitro. Kanjani icebo inqubo eqhubekayo?

Ukuze ukuchaza nitration ka toluene, ezothando yokusabela kungenziwa elabekwa kanje:

ArH + HONO2 + = Ar-NO2 + H2 O

It ikuvumela ukuba bahlulelwe kuphela Yiqiniso jikelele nokuxhumana, kodwa alisho zonke izici le nqubo. Empeleni kukhona ukusabela phakathi hydrocarbon enamakha imikhiqizo nitric acid.

Njengoba sazi ukuthi umkhiqizo has a molecule amanzi, ngoba kunciphisa lokuhlushwa nitric acid, nitration ka toluene ke siyehla. Ukuze ugweme le nkinga, inqubo yenziwa ngaphansi kwamazinga okushisa aphansi usebenzisa nitric acid in imali ngokweqile.

Ukwengezwa sulfuric acid ziyizinto dehydrating esetshenziswa , anhydride acetic, polyphosphoric acid, boron trifluoride. Zenza snizat ukusetshenziswa nitric acid, ukwandisa nekusebenta nokuxhumana.

Ezicashile inqubo

I nitration ka toluene achazwa ngasekupheleni kwekhulu nesishiyagalolunye V Markovnikov. Wakwazi ukusungula ukuxhumana phakathi khona e ingxube yokusabela bagxila sulfuric acid futhi inqubo ukugeleza rate. asetshenziswa zesimanje zokukhiqiza nitrotoluene anhydrous nitric acid, ezithathwe ngokweqile okuncane.

Ngaphezu kwalokho, sulfonation futhi nitration ka toluene Kuhilela ukusebenzisa etholakalayo dehydrating boron ingxenye-fluoride. yethula kunqubo ukuphendula kwenza ukunciphisa izindleko umkhiqizo etholwe, okwenza kutholakale nitration ka toluene. Isibalo egeleza inqubo ngokuvamile zazimi kanje:

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

Ngemva kokuphothulwa amanzi ukuphendula yethulwa, lapho monohydrate boron fluoride dihydrate amafomu. It isuswe vacuo, bese ufaka i-calcium one-fluoride, kubuyela kwakwakhe owaqalwa.

Ngokucacile of nitration

Kukhona ezinye izici inqubo ephathelene kukhethwa reagents, substrate usebenzisa ukuphendula. Cabangela ezinye izinketho zabo ngaphezulu:

• amaphesenti 60-65 nitric acid ngengxube ezingamaphesenti angu-96 i-sulfuric acid;
• inhlanganisela 98% nitric acid kanye kanzulu sulfuric acid ngoba kancane ukuphendula izinto eziphilayo;
• potassium nitrate noma ammonium nge kanzulu sulfuric acid - kuyinto choice omuhle ukwenziwa polymer ka nitro compounds.

I kinetics ka nitration

hydrocarbon elimnandi, uxhumana nenye sulfuric futhi acid nitric, nitro ionically. V. Markovnikov bakwazi njani ngokucacile nokuxhumana. Inqubo yenzeka ngezigaba eziningana. Nitrosernaya acid is kuqala kwakhiwa, okuyinto asitholayo dissociation e ikhambi aqueous. Nitronium ion kuthiwa wasithukuthelela toluene ukwakha njengoba nitrotoluene umkhiqizo. Lapho ingezwe ku ingxube amangqamuzana awuketshezi kwenzeka ngesikhathi deceleration.

Ngo kumakhemikhali awuketshezi nemvelo organic - nitromethane, acetonitrile, sulfolane - ivumela ukwakheka seka ukwandisa izinga nitration.

ngaleyo ndlela kwaphumela nitronium seka enamathiselwe nucleus elimnandi of toluene, kwakhiwa Lesisemkhatsini. Ngaphezu kwalokho kukhona igebe proton, okubenze bafinyelela nitrotoluene kumiswa.

Ukuze uthole incazelo eningiliziwe inqubo eqhubekayo singacabangela ekwakhekeni "sigma" futhi "pi" eziyinkimbinkimbi. Imfundo "sigma" eyinkimbinkimbi kuyisinyathelo izinga sinciphisa nokuxhumana. Izinga yokusabela is kuhlobane ngokuqondile rapidity of nitronium seka okunamathiselwe ku-athomu carbon Kuyi-nucleus ezinuka kamnandi. proton eqhekeza off toluene Kwenziwa ngokuphazima kweso.

Kuphela kwezinye izimo, kungase kube izinkinga esikhundleni ehlotshaniswa ne abalulekile eyinhloko kinetic IKhompyuthaYami umphumela. Lokhu kungenxa ukusheshisa inqubo ukubuya ebukhoneni izithiyo ezihlukahlukene.

Uma ukhetha kulethe kanye ejenti dehydrating nge kanzulu sulfuric acid inqubo kukhona shift yakhoibrium maqondana kumiswa imikhiqizo ukuphendula.

isiphetho

It kwakheka nitration ka toluene nitrotoluene, eliwumkhiqizo zenani elikhulu zomuntu umkhakha zamakhemikhali. Kuyinto yalolu ketshezi kuyinto kwakwakhe kuqhume, ngakho izimfuno ukuqhumisa imisebenzi. Phakathi kwezinkinga nezemvelo ezihlobene enza yayo zezimboni, uqaphele ukusetshenziswa okunqala kanzulu sulfuric acid.

Ukuze sibhekane nale nkinga, osokhemisi ufuna izindlela zokunciphisa imfucuza sulfuric acid etholwe emva inqubo nitration. Ngokwesibonelo, inqubo yenziwa at okushisa aphansi, medium esetshenziswa kalula regenerable. Sulfuric acid has eqinile oxidizing izakhiwo, okuyinto omubi kuthinta ukugqwala of izinsimbi luyanda yingozi eziphilayo. Ngokuhambisana zonke izindinganiso zokuphepha angabhekana lezi zinkinga, ukuthola izinga okusezingeni nitro compounds.