TRNG I HC CNG NGHIP TP HCM

KHOA CNG NGH HA HC

BI 9: IU CH 2 NAPHTYL METYL ETE

GVHD: TS.MAI HNG THANH TNG
Nhm TH: Nhm 5
Tn thnh vin

MSSV

Hunh Ngc Dip

14131271

Nguyn Tn t

14123771

Lng c

14127431

NI DUNG
1. Mc ch th nghim
2. C s l thuyt
2.1 nh ngha
2.2 Phn loi
2.3 C ch phn ng
2.4 Cc yu t nh hng n qu trnh alkyl ha
3. Cch tin hnh
3.1 Dng c v ha cht
3.2Tng quan v sn phm cn iu ch
3.3 Tnh ton nguyn liu
3.4 Quy trnh
3.5 Kt tinh li sn phm
4. Tr li cu hi

1. Mc ch th nghim:
Sau khi hc xong bi ny ngi hc iu ch v xc nh nhit
nng chy ca 2 naphthyl methyl ether.

2. C s l thuyt:
2.1.
nh ngha:
Phn ng alkyl ho l phn ng thay th mt hoc nhiu nguyn t H hot ng
ca phn t hu c bng mt hoc nhiu nhm alkyl.
2.2.

Phn loi:

Da trn gc Alkyl gn vo C, O, N hoc S m ta c c loi alkyl ha sau:

C alkyl ha: Th nguyn t H gn vi C bng nhm alkyl
O alkyl ha: Phn ng to thnh lin kt gia nhm alkyl v nguyn t O
N alkyl ha: Th nguyn t H trong ammoniac hoc trong amin bng nhm alkyl
S alkyl ha: Phn ng to thnh lin kt gia nhm alkyl v nguyn t S

2. C s l thuyt:
2.1.

nh ngha:

2.2.

Phn loi:

2.3.

C ch phn ng:
OH

+ CH3OH

O
CH3

H2SO4 98%

+ H2 O

2 naphthyl methyl ether

Loi phn ng: O alkyl ha, di s c mt ca acid H 2SO4

v un hi lu nhit cao.
Phn ng theo c ch: Phn ng th Nucleophile (SN2).

2. C s l thuyt:
2.1.

nh ngha:

2.2.

Phn loi:

2.3.

C ch phn ng:

2.4.

Cc yu t nh hng n qu trnh alkyl ha:

Nhit : nhit cng tng th tc phn ng cng tng theo

Nng : Khi tng nng ca tc cht alkyl ha lm tng hiu sut ca
qu trnh alkyl ha
Tc nhn alkyl ha: Trong bi ny chng ta lu n tc nhn alkyl ha l
Ru, khi tc nhn alkyl ha l ru th phn ng c thc hin trong
iu kin nhit cao (30 200 oC), p sut cao (37 40 atm)

3. Cch tin hnh:

3.1.

Dng c v ha cht:

1 bnh cu nhm 250 mL

H2SO4 c

1 ng sinh hn

1 b lc p sut km

1 a thy tinh

1 ng ong

4 t giy lc

2 becher 100 mL

1 bp in

My sy tc

2 naphtol

Ru metilic tinh khit

NaOH 10%

Cn cng nghip
bt

3. Cch tin hnh:

3.2.

Tng quan v sn phm cn iu ch:

Tnh cht vt l:
Tn IUPAC: 2 methoxynaphthalene
Tn thng thng: methyl napthyl ether hay naphthyl methyl ether
Mu sc: Tinh th mu trng
im chy: 73 75oC
im si: 274oC
Khng tan trong dung mi nc, tan trong dung mi hu c nh: ru,
benzene, chloroform, ether.
ng dng:
Metoxy naphtalen l tn gi khc ca 2 Metyl naphtyl ete, c s dng
nh cht trung gian cho tng hp ca thuc khng co git steroid
Thnh phn trong nc hoa v m phm, ch yu l hng liu
Lm cht n nh trong x phng.

3. Cch tin hnh:

3.3.

Tnh ton nguyn liu:

OH

+ CH3OH
1 mol
m2

CH3

H2SO4 98%

8 mol

1 mol acid

V1

V2

+ H2 O
1 mol
m1 = 3 g

Tnh m1 = khi lng NaOH cn ly iu ch 250g dung dch NaOH 10%,

NaOH c M = 40, p = 96%

Tnh m2 = khi lng 2 naphtol cn ly tin hnh phn ng, M = 144,17 g/mol
V t l mol l 1:1 nn ta s dng quy tc tam sut tm khi lng m2
2 naphtyl methyl ether
2 - naphtol
M = 158,9 g/mol
m1 = 3g

M = 144, 17 g/mol

3. Cch tin hnh:

3.3.

Tnh ton nguyn liu:

Tnh V1 = th tch ru metilic cn ly tin hnh phn ng, d = 0,78 g/mL

2 naphthyl methyl ether

Ru metilic

Khi
Khi lng
lng phn
phn t
t
T
T l
l mol
mol

M
M=
= 158,9
158,9 g/mol
g/mol
11 mol
mol

M
M=
= 32
32 g/mol
g/mol
88 mol
mol

Khi lng ti 1 mol

Khi lng ti 1 mol

158,9 g
158,9 g

32.8 = 256 g
32.8 = 256 g

3g
3g

S dng quy tc tam sut:

Khi lng ti

Khi
Khi lng
lng ring
ring ca
ca ru
ru dd =
= 0,78
0,78 g/mL
g/mL

Trong 1 mL dung dch c 0,78 g nguyn cht ru

metylic.
S dng quy tc tam sut, trong nguyn cht ta s tnh
c s mL ru cn ly:

3. Cch tin hnh:

3.3.

Tnh ton nguyn liu:

Tnh V2 = th tch acid sulfuric 98% cn ly tin hnh phn ng, d = 1,98 g/mL
2 naphthyl methyl ether

H2SO4

Khi lng phn t

T
T l
l mol
mol

M = 158,9 g/mol
11 mol
mol

M = 98 g/mol
11 mol
mol

Khi
Khi lng
lng ti
ti 11 mol
mol

158,9
158,9 gg

98
98 gg

3
3 gg

S dng quy tc tam sut:

Khi lng ti

Nng phn trm acid sulfuric C% = 98%

Khi lng ring ca ru d = 1,98 g/mL

Trong 100 g dd H2SO4 c 98 gam H2SO4 nguyn cht

S dng quy tc tam sut, trong nguyn cht ta cn ly

Trong 1 mL dung dch c 1,98 g nguyn cht ru metylic

S dng quy tc tam sut, trong nguyn cht ta s tnh c s mL acid
cn ly:

3. Cch tin hnh:

3.4. Quy trnh:
Kim tra dng c.
Cn 3g 2 naphtol cho vo bnh cu 1 c nhm.
Ly bng pipet 6 mL ru metilic.
H2O ra

Dng pipet ly 1,0 mL H2SO4 m c cho vo bnh cu,

thm tip 2 3 vin bt. Lc u hn hp phn ng.
Lp t h thng un gm bp in vi sinh hn hi lu,

Van H2O vo

kim tra h thng nc tun hon m bo lnh.

Cm in vo bp cch thy.
un hon lu bnh cu trn cch thy, thi gian 90 pht
(tnh thi gian t lc nc bt u t nhit khong
90oC).

3. Cch tin hnh:

3.4.

Quy trnh:
Ngng un ngui n khi ngng
si, rt ngay hn hp lng trong
bnh cu cn nng vo becher c
cha sn 50 mL nc lnh.

Becher 100 mL

Becher
sn
phm
th,
a vo phu
lc
Phu
lc
xp

Khuy u hn hp
trong becher 100 mL
bng a thy tinh
Becher: nc,
sn phm phn
ng

Lc sn phm trn b
lc p sut km.
Ra li nhiu ln bng
nc lnh loi sch
acid d.

Bm
chn
khng

3. Cch tin hnh:

3.5.

Kt tinh li sn phm:

Ly bng pipet
20 ml dd NaOH
10% cho vo
mt
becher
100mL.
Cho sn phm
th vo becher
khuy u.

un si v khuy
u cho cht rn tan
hon ton.

Lm lnh becher
trong thau nc
c mt t mui
NaCl, tinh th 2naphtyl metyl ete
xut hin

Lc sn phm trn
phu lng p sut thp
Ra nhiu ln sn
phm cho n khi ht
baz
Sy sn phm 1000C
Cn sn phm, cho vo
chai thu hi

3. Cch tin hnh:

3.5.

Kt tinh li sn phm:

Xc nh nhit nng chy ca cht rn:

a mt t cht rn 2- naphtyl metyl ete va
Becher
sn
phm
th,
a vo phu
lc

iu ch c ln giy lc.
Tn nh cht rn.
Hn knh mt u ng mao qun c ng
knh 1mm.

Phu
lc
xp

Dng mao qun chm u cha hn vo cht

rn sao cho cht rn c nn cht trong ng
c chiu di 6mm.

Bm
chn
khng

3. Cch tin hnh:

3.5.

Kt tinh li sn phm:

Xc nh nhit nng chy ca cht rn:

Buc mao quan vo nhit k bng dy cao su
cho u c tinh th ngang vi thu ngn
trong nhit k.
Cho nhit k c gn ng mao qun vo ng
nghim c ch cong nh hnh v, c cht
truyn nhit l glycerin.
Dng n cn un ch cong ca ng thu
tinh.
Theo di nhit ca nhit k.
c nhit ca nhit k khi cht rn nng
chy trong sut.

Tr li cu hi
1. S tng qut ca qu trnh tng hp sn phm:
Kim tra dng c

3g 2 naphtol
6 mL CH3OH
1 mL H2SO4
2 3 vin bt

Lc sn phm trn b
lc p sut km

Ra li nhiu ln bng
nc lnh loi acid d

Dng a thy tinh

khuy u hn hp
trong becher

Sn phm th

Becher cha 20 mL
NaOH 10%, khuy u

Bnh cu c c nhm

Lc u hn hp
phn ng

Lp sinh hn, kim

tra nc hon lu v
ra sinh hn

dd ht si, rt ngay
hn hp lng nng vo
Becher c cha sn 50
mL nc lnh

Cm in, un hon
lu bnh cu cch thy
khong 90 pht

un si v khuy u
cho rn tan hon ton

Lm lnh trong nc
c t mui NaCl

Sy 100oC, cn sn phm
v cho vo chai thu hi

Ra li nhiu ln bng
nc lnh loi baz d

Lc sn phm trn b
lc p sut thp

Tinh th 2
naphthyl
methyl ether
xut hin

2. Cch tnh hiu sut:

Trong :
- khi lng cht cn iu ch c m th nghim yu cu.
- khi lng cht ta iu ch c sau khi thc hnh.

3. Phn ng iu ch 2 naphthyl methyl ether:

OH

+ CH3OH

O
CH3

H2SO4 98%

+ H2O

2 naphthyl methyl ether

3. C ch phn ng:
Trong mi trng acid:
H

H3C

OH

H+

CH3

CH3+

O+
H

phn t -naphtol s ht electron hai nhn thm i vi oxi cng vi

s ht e ca oxi lm cho nguyn t Hydro rt linh ng.
O

H2 O

3. C ch phn ng:
O

H3C

OH

H2SO4

Chm

CH3

OH

Trng thi chuyn tip

Nhanh

O
CH3

H2 O

H2SO4

3. Cc ng dng ca sn phm tng hp trong bi:

Metoxy naphtalen l tn gi khc ca 2 Metyl naphtyl ete,
c s dng nh cht trung gian cho tng hp ca thuc
khng co git steroid.
Thnh phn trong nc hoa v m phm, ch yu l hng
liu
Lm cht n nh trong x phng.

4. Anh (Ch) hy trnh by: dung mi kt tinh li sn

phm, ti sao phi dng dung dch NaOH cho vo sn
phm, phng php kt tinh li trong bi l phng
php kt tinh g?
Phi dng NaOH cho vo sn phm v:
NaOH trung ha lng 2 naphtol d
Phng php kt tinh li trong bi l phng php:
Kt tinh chn khng

5. Cc mi c trng (A G) hp thu IR ca hp cht:

Hnh 11.1 trang 186 sch gio trnh thc hnh

5. Cc mi c trng (A G) hp thu IR ca hp cht:

K hiu

S sng (cm)

Mi hp thu

Ghi ch

A
B

3090 3095
2950 2970

C H gin
C H gin

C
C

810
810 840
840

Nhm
Nhm th
th -- O
O CH3
CH3

v
v tr
tr ortho
ortho

Cng hp thu mnh

Cng hp thu trung
bnh mnh
Cng
Cng
hp
hp thu
thu rt
rt
mnh
mnh

D
D
E
E

1030 1040
1030 1040
1620 1640
1620 1640

C = C gin
C = C gin

F
F

1430 1440
1430 1440

C = C gin
C = C gin

G
G

1220 1230
1220 1230

Cng hp thu c th
Cng
thay i hp thu c th
thay i
Bng ny c lu tm
Bng
ny c
tm
khi vng
thmlumang
khi
thm
nhmvng
th phn
cc mang
nhm th phn cc