HERMIN HARDYANTI UTAMI (111 304 0202)

CHEMISTRY DEPARTMENT

MATHEMATIC AND SCIENCE FACULTY

STATE UNIVERSITY OF MAKASSAR

2012

RATIFICATION PAGE

The complete report of Organic Chemistry II with the title of “Preparation

of Acetinilide” which made by :

Name : Hermin Hardyanti Utami

ID : 111 304 0202

Group : VII

Class : ICP B

Have been checked by assistant and assistant coordinator. So, this report is accepted.

Makkassar, December 2012

Assistant Coordinator

Fandi Ahmad, S.Pd.

Assistant

Burhanuddin, S.Pd

Known By,

Responsibility Lecturer

Dra. Hj. Ramdani, M.Si.

A. Title of Experiment

Preparation of Acetanilide

B. Purpose of Experiment

1. Skilled to set and use equipment ansyntesis of organic substance

2. Explain the rise refining techniques

3. Explain principle of chemistry amine the derivative compound

C. Backround

Amine is organic compound that contain nitrogen atom trivalen that bond

with one or two or three carbon atomic. If in structure formula, amina is derivate

from ammonia that one, two, or three hydrogen atomic changed by alkil or aril

group. Therefore, uf changer group hydrogen atomic in ammonia like aril group

(R), then structure of aliphatic amine that maybe happen is RNH2, R2NH or R3N.

if changer group us aril (Ar) will see same formula (Rasyid, 2009:187).

Classification and namecleature of amina. Amina can grouped as primery,

secondary, and tersiery, according subtituen of alkil or aril that bonded wuth

nitrogent.

1C bond 2C bond 3C bond

CH3NH2 -NH-CH3 (CH3CH2)3N

Alkylamine primery arilalkilamine secondary trialkilamine tertier

A nitrogen amine can have four group or atomic that bond in this way,

nitrogen is the part of positive ionic. This compound devide two parts. If one or

more that bond is H then this compound called amine salt. If forth the group is

aril or alkyl (not H in N), then compound called cuartener

Ammonium salt:

Amine salt

(CH3)2NH2+

Cl

Dimethyl ammonium chloride N-methylpiperidium bromida

Salt from secondary amine salt from tersier amine

Cuartener ammonium salt

(CH3)4N+Cl CH3CO2CH2CCH2N

+(CH3)3Cl

Tetramethyl ammonium chloride acetilcoline chloride

(Fessenden, 1976: 122-123)

Acetanilide is converted to a phenolic metabolite in human body which

gives it an analgesic effect, but some is converted to aniline (aminobenzene)

which is toxic. It was found that for a single dose of 10 mg/kg of acetanilide. The

half life in blood plasma was 191,5 +27,5 min of in 25 dose of 10mg/kg of

acetanilide the half life in blood plasma was 191,5+27,8 min of in 25 subject

(human) and the metabolic clearance rate was 14,1+2,8 liter/h of the structure

formula is

(Oecd sid,2004:10)

Benzothiazoles and N-Subtututed-o-chloro acetanilides have emerged as

structurally novel anti oxidant activity. Therefore hydrazine benzothiazoles and

acetanilide derivates on important class of medicinal compound. The search for

antioxidant compounds with more selective and lower toxicity continues to be area

of investigation in medical chemistry compounds containing a hydrazine benzothia

zole, hydrazine benzothiazine and substituted chloro acetanilide component have

shown a broad spectrum of chemotherapeutic properties including antimicrobial,

antiviral anthelmentic, analgesics, until inflammatory and antycytotoxic activies of

substituted acetanilides (Suresh, dkk. 2011: 409).

R-NH2-R-C R-C-N+H2R R-C-NH-R+ x

-

x= -OH, -OCOR or –Cl

acetilation uses glacial acetalec acid that more cheap, although use long

time. Because in last process there is equilibrium

R-NH2+ CH3COOH R-NH-C-CH3 + H2O

Then to get high result, equilibrium need to moved to right with lost the air

and produced by distillation. (Tim dosen, 2012: 5-6).

There are few simple of anilyn structure phenoylamate is qually call aniline

aniline

Heterocyclic compound the nitrogen part of aring compound used as

different heterocyclic ring like parent hame

Pyridine perin

(Mc Murry,2007:373).

D. Apparatus and Chemicals

1. Apparatus

a. Distillating flask 1 peace

b. Reflux condenser 1 peace

c. Thermometer 240oC 1 peace

d. Volumetric glass 25 ml 2 pieces

e. Buchner funnel and funnel 1 piece

f. Wash bottle 1 piece

g. Erlenmeyer 1 piece

h. Beaker glass 100 ml 1 piece

i. Stir bar 2 pieces

j. Store and boiling stone 1 piece

k. Rough and smooth cloth 1 piece

l. Dropping pipette

2. Chemicals

a. Aniline (C6H5NH2)

b. Glasial acetic acid (CH3COOH)

c. Actirated carbon/ norite

d. Capiler pipe

e. Alluminium foil

f. Aquadest

g. Alcohol

h. Filtering paper

i. Whatmann paper

j. Ice cubes

E. Work Procedure

1. Put into a round flask 25 ml acetic acid and 20 ml amine

2. Put same boiling stones into round flask and refluxed with temperature (104-

105oC) to 13,5 ml

3. After refluxed, then mixed into the ice tube in the residue (acetanilide) and

stired to form a solid crystal alkine form

4. Heated to boiling and then diluted with alcohol and water then added norit

5. Filterated the solution with a Buchner filtered and conducted dirty acetanilide

crystal solids

6. Solids acetanilide products of the synthesis was dissolved in again with

alcohol and heated to boiling and then added norit to it

7. The solution filtered again with Buchner and then result put into beaker and

filtered called used ice tube to obtain crystals acetanilide

8. Mixed a crystal is then filtered with filter paper

9. Dried of crystal more obtained from filtration ands measured weight and

melting point

F. Observation Result

No Observation Result

1

Measured aniline in volumetric

glass

12,5 ml with red solution

2

3

4

5

6

7

8

9

10

11

12

13

14

Measured acetic acid in volumetric

glass

Aniline + acetic acid + boiling

stone into round flask

Distillated mixture until

temperature 104oC

Filled the residue unto cool water

Filtered the brown chunks

Dissolved the residue with ethanol

+ H2O

Added mixture with norite and

heated

Filtered dark brown solution with

funnel

Filled the filtrate into cold water

Filtered the crystal with using

funnel

Put the crystal into the oven

Balanced the dry crystal

Determine melting point of

acetanilide crystal

10,00 ml transparanmt solution

Red mixture solution

Separated: 1) residue (acetanilide)

2) dustllate + H2O (yellow solution)

Brown chunks + solvent

Separated -> transparent (filtrate)

Residue (brown chunks)

20:20 ml ethanol and H2O

Dark brown solution

Separated -) turbid (filtrate)

Dark brown chunks

Until formed with crystal + solvent

Filtered, residue (crystal)

Filtrate (solvent)

Dry crystal (acetanilide)

Pure acetanilide (1,5g)

113-116oC

G. Data Analysis

Known = - V C6H5NH2 = 12,5 ml

- V CH3COOH = 10 ml

- Mr C6H5NH2 93 g/mol

-Mr CH3COOH = 60 g/mol

- Mr C6H5NHCOOCH3 = 135 g/mol

- p aniline = 1,022 g/ml

- p CH3COOH = 1,049 g/ml

Ask = rendemen?

Mass of aniline = (p x v) aniline

= 1,022 g/ml . 12,5 ml

= 12,775 g

Mass of CH3COOH = (p x v) CH3COOH

= 1,049 g/ml . 10 ml

= 10,49 g

Mol of aniline =

=

= 0,137 mol

Mol of CH3COOH =

=

= 0,17 mol

C6H5NH2 + CH3COOH CH3CONHC6H5 + H2O

M 0,137 mol 0,17 mol

B 0,137 mol 0,137 mol 0,137 mol 0,137 mol

S - 0,033 mol 0,137 mol 0,137 mol

Theory mass of acetanilide

= (mol x Mr) CH3CONHC6H5

= 0,137 mol . 135 g/mol

= 18,459 g

Rendement =

x 100%

= 0,081 x 100 %

= 8,1 %

H. Explanation

In this experiment, acetanilide was made with react aniline as base material

with glatial acetat acid solution. The aniline prepare a amine group therefore glatial

acetat acid or pure acetat acid without other mixing. It function as preparer asetil

group or reactant (nucleofil) that will be substitute by amine group and group which

can move the other atom. This structure can move or release from its structure. Then

this mixing was destilated in temperature 104-105oC to separate acetanilide with

reaction side result which formed namely water. The temperature was kept in order

not more or less from 104-105oC in order the acetanilide which formed not broken

and the water can be out because boiling point of water is 100oC. Before done

distillation was entered boiling stone in the mixing prevent occur the explotion in

heating. The distillate which be gotten in kept and the residue which be there is the

cycle flask cold in cold water to fast formed of crystal. So it filtered with Buchner

and result brown residue. Then added ethanol 1% and water. The adding of water 20

ml with purpose to dilute the sediment or crystal therefore ethanol purpose to dilute

the crystal which yet diluted when adding of water, beside of that the ethanol also

purpose to recrystallization and lost the dirty substances. Recrystallization purpose

to get the acetanilide that be purer. Then added norit and heated, the function of norit

to adsorb color. So, heated and filtered in heat condition. It thing in order to avoid

formed the crystal when the solution was cold. After filtered, get the white crystal,

then the crystal entered in the oven because the crystal still contain water. After dry

the color of crystal is white, it suitable with theory that the crystal of acetanilide is

white. The mass of acetanilide is 1,5 gr with rendement 8,1 %. After that done the

test of melting point , got melting point of acetanilide is 113-116oC. It suitable with

theory that melting point of acetanilide is 113,7oC

The reaction is

NH

H

+

O

OH

CH 3

NH

H

+ C+

OH

CH 3

O-

NH

H

+ C+

OH

CH3

O-

CH3

O-

OH

N+

H

H

CH3

O-

OH

N

H

+ H+ + H

+

+ OH-

CH3

O-

N

H

CH3

O-

N

H

+ H+

+ OH-

CH3N

H O

+ OH2

Acetanilide water

I. Closing

1. Conclusion

a. In this experiment rendement is 8,1% and the mass of acetanilide is 1,5 g.

b. The preparation of acetanilide in acetalase process us a reaction between

aniline with acetate acid product in the form of crystal purified by

crystallization.

2. Suggestion

a. Apperantice must be carefully to keep the temperature when distillation

process.

b. Apperantices must be carefully when filtering

CH3

O-

OH

N+

H

HCH3

O-

OH

N

H

+ H+

BIBLIOGRAPHY

Fussenden. 1976. Kimia Organik Edisi Ketiga Jilid 2. Jakarta: Erlangga.

Mc Murry. 2007. Fundamental of Organic Chemistry. London: Thomson Red

Camprk.

Decsids. 2004. Acetanilide. UNEP publications.

Rasyid. 2009. Kimia Organik 1. Makassar: UNM.

Suresh. 2011. Synthesis of 2-Hydrazinobenhotalzoles-2-aminos(4substiturted)-

acetanilides for antyoxidant Activity. India International Journal of

Pharmacy and Biologycal Science.

Tim Dosen. 2012. Penuntun Kimia Organik II. Makassar: UNM.