I.

Gii thiu

1. Gii thiu v Sudan

Hnh 1. Dye Sudan I Sudan (Sudan dyes) l cht mu ha tan trong cht bo tng hp, thuc nhm azo lin hp c nhm N=N trong phn t, n c s dng to mu cho cc loi dung mi, cc loi du, sp, du kh, nh bng giy v sn nh. Cht nhum sudan 1, sudan 2, sudan 3, sudan 4 c cc mu , cam, sm v m. Chng l cc cht hu c c chit ra t nha than , c tm ra cch y 150 nm [4]. Cc cht ny ch c php s dng trong cc loi nu trn, cm s dng chng trong thc phm v thc ung. Cng thc cu to ca 4 loi sudan sau:

OH

N N

Sudan I (C16H12N2O)

HO

Sudan II (C18H16N2O)

HO

Sudan III (C22H16N4O)

HO

Sudan IV ( C24H20N4O)

Sudan cn l mt loi phm mu tng hp cha cc hp cht azo, naphtols v cc gc methyl di ng. Thng thng phm mu c p dng thng xuyn trong thc phm l sudan I, c cng thc tng qut l C16H12N2O

Ngoi ra cn c sudan II mu cam, sudan III mu ceresin (mu m), v sudan IV cn c tn l dung mi 24

Sudan I l mt trong nhng cht thuc nhm cc Azo nhng cng c nhiu tn gi khc nhau nh 1-(Phenylazo)-2-naphthalenol 1-(Phenylazo)-2-naphthol 1-[(E)-Phenyldiazenyl]-2-naphthol 2-Hydroxy-1-phenylazonaphthalene 2-Hydroxynaphthyl-1-azobenzene 2-Naphtholazobenzene Cc nh khoa hc khng nh rng sudan c kh nng gy ung th, Cc nh khoa hc lm th nghim trn ng vt vo nm 1949 cho thy, sudan lm tn hi gan ca cc loi gm nhm, lm pht trin khi u trong gan v gy ung th gan. Cc khi u cng pht trin trong bng quang, thn... cng nh gy khi u trong

tuyn gip trng ca loi B. Nhng nghin cu gn y cho thy, sudan gy tc dng ph v cu trc AND v nhim sc th khi a vo mi trng nui cy t bo. Sudan khi i vo c th theo n v thc ung hoc qua da - sau khi nh mu trong cc m m, n s b phn on do phn ng azo kh cho ra aniline v aminonaphtol l hai cht c i vi con ngi. Mu sc m phm cng , cng lu phai th hm lng sudan cng cao. T cc nghin cu ny dn n vic cm s dng sudan trong ch bin thc phm v m phm vo nm 2003 Anh v Chu u. 2. Gii thiu v 2- naphthol 2- naphthol hay -naphthol l mt tinh th rn khng mu c cng thc phn t l C10H7OH. N l mt ng phn ca 1-naphthol, ch khc v tr ca nhm OH.

Hnh 2. Cu trc 2-naphthol

II.

Tin trnh th nghim

1. Dng c v ha cht

Dng c
Cc 100ml ng ong 5ml ng ong 100ml Bnh nn 125ml Phu thy tinh 3 3 1 2 1 2-naphthol NaOH 3M Aniline NaNO2 Nc ct

Ha cht

Giy ch th KI Axit HCl

2. Tin trnh Chun b dung dch mui Natri 2- naphthol. Cn 79mg mui 2- naphthol cho vo dung dch 3M NaOH ( pha ri) trong cc 100ml. Ngm hn hp ny trong nc lm lnh cc 1 Chun b Mui benzene diazonium: Cn 51mg aniline b vo cc 100ml, sau thm 0,25ml HCl m c (12M) v 0.5ml nc ct.

Dng a thy tinh khuy cho n khi hn hp ha tan hon ton, sau em hn hp ny ngm trong nc nhit trong khong 0-5oC cc 2 Cn 40mg NaNO2 cho vo cc 100ml , sau thm 0.5ml nc ct cc 3 - Cho tng git dung dch NaNO2 vo cc cha hn hp aniline ( Khi thm NaNO2 vo, hn hp aniline vn phi c lm lnh.) kim tra lng d HNO2, ta dng giy tm KI lm ch th. Ly vi git dung dch mui benzene diazonium nh ln giy ch th, quan st mu trn giy. Nu c s xut hin mu ta th ta thm ure cho n khi kim tra khng thy mu ta xut hin na. Thc hin phn ng gia mui benzene diazonium v Natri 2-naphtholate - Nh tng git mui benzene diazonium chloride vo dung dch Natri 2naptholate , khi 2 hn hp vn c gi nhit 0-5 Khuy hn hp cho 2 hn hp c trn u. Quan st thy hn hp c mu m v chuyn sang cam khi thm vi git HCl Sau ngm hn hp trong nc khong 15 pht th em lc bng phu thy tinh. - Sau khi lc ta em sy sn phm thu c v cn sn phm 3.C ch tng hp Sudan
Giai on 1:

u tin sodium nitrite phn ng vi acid HCl th chng phn ng to thnh acid nitrous. trong mi trng c tnh acid th acid nitrous b proton ha v acid nitrous b mt nc v to thnh ion nitrosonium.

Giai on 2:

Giai on 3: Nitrosoamine chuyn ha proton (tautomerism) v dng nitro bn hn dng axinitro

Giai on 4: Di iu kin acid, nhm OH b proton ha v v th tch nc ra to thnh mui diazonium

Mui diazonium

T mui diazoni to thnh dye Giai on 5: Phn ng ngng t - Th no l mt pn ng ngng t: Phn ng ngng t l phn ng gia mui diazonium vi mt amin thm hay phenol to thnh phm mu azoic. Qu trnh ny i theo c ch ghp i mui diazoni vi 2-naphthol trong mi trng kim. - Trc ht, 2-naphthol c ha tan trong kim to thnh mui natri 2naphthalate.
-

Tip theo l phn ng ngng t ca mui diazoni v C10H7O-

2-naphthol tch dng vi sodium hydroxide to thnh naphthalene-2-olate

Giai on 6: Ion Benzendiazonium tn cng vo 2-naphthalene-2-olate hnh thnh 1phenylazo-2-napphthol hay Sudan I.

1 2 3

III. Nguyn tc trong tng hp Sudan I

Mui diazoni c hnh thnh trong phn ng c nhng c im nh sau: - L dng bt t tan trong nc - L hp cht khng bn, nhit cao c th b phn hy thnh phenol theo phn ng sau:

C H N + Cl + H O > C H OH + N + 6 5 2 2 6 5 2
trnh cho mui hnh thnh b phn hy thnh phenol.

HCl

V th trong khi tng hp cn tin hnh trong iu kin nhit khong 0-50C, Qu trnh diazo ha c mt ngha rt quan trng v vi vic diazo ha c th dn

n mt nhm hp cht c kh nng phn ng cao v t nhng hp cht ny c th iu ch ra nhiu dn xut mi. Diazo ha l phn ng ch yu dung trong cng nghip sn xut cc phm mu azoic. y l phng php n gin, r tin. Tuy nhin qu trinh diazo ha chu nh hng bi yu t nhit Nhit cng tng th tc phn ng cng tng nhng km theo n l kh nng tng phn hy ca hp cht diazoni. Thng thng phn ng phi tin hnh trong khong 0-50C . nhit thp, kh nng to ra kh HNO2 to ra ha tan tt hn v trong mi trng axit mnh kh nng to ra kh NO nh, duy ch c mt bt li nh l nhit thp, kh nng ha tan ca hn hp chm dn n tc phn ng chm. IV. Ti liu tham kho PSG.TSKH. Phan nh Chu-Cc qu trnh c bn tng hp -hu cNXB KH_KT. http://www.scrib.com http://www.synthesis.com