Université 08 aout 1955

-Skikda –
Département of chimie
Chimie Analytique

Acide acétique
ACETIC ACIDE

Dr Naili | informatique pour la chimie | 04-11-2024

Group : 04

University year : 2024/2025

Team names :
_BENYOUCEF HADJER
_BOUBELLI RAYANE
_BOUDAB MOHAMED NOUR EL ISLEM
_GUERNANE ABDESSAMED

_DJEROURI BADIS
_BOUCHAMA HACHEM
_BOUROUINE YASSAMINE
_BRAHIMI KARIMA
_FOUDIL MAROUA
_GRID MALAK

PAGE 1
 Introduction :
Acetic acid (CH3COOH), the most important of the carboxylic acids. A dilute
(approximately 5 percent by volume) solution of acetic acid produced
by fermentation and oxidation of natural carbohydrates is called vinegar;
a salt, ester, or acylal of acetic acid is called acetate. Industrially, acetic acid is used
in the preparation of metal acetates, used in some printing processes; vinyl acetate,
employed in the production of plastics; cellulose acetate, used in making
photographic films and textiles; and volatile organic esters (such as ethyl and butyl
acetates), widely used as solvents for resins, paints, and lacquers. Biologically, acetic
acid is an important metabolic intermediate, and it occurs naturally in body fluids
and in plant juices. Acetic acid has been prepared on an industrial scale by air
oxidation of acetaldehyde, by oxidation of ethanol (ethyl alcohol), and by oxidation
of butane and butene. Today acetic acid is manufactured by a process developed by
the chemical company Monsanto in the 1960s; it involves a rhodium-iodine
catalyzed carbonylation of methanol (methyl alcohol).

Pure acetic acid, often called glacial acetic acid, is a corrosive,

colourless liquid (boiling point 117.9 °C [244.2 °F]; melting point 16.6 °C [61.9 °F])
that is completely miscible with water.

Definition :

 Molecular FormulaC2H4O2
 Average mass60.052 Da
 Monoisotopic mass60.021130 Da
 ChemSpider ID171

Names and synonyms:

acetico [Italian]
cide acétique [French] [ACD/IUPAC Name]
Acido

PAGE 2
AcOH [Formula]
ättiksyra [Swedish]
azido azetikoa [Basque]
azijnzuur [Dutch]
Essigsäure [German] [ACD/IUPAC Name]
Ethanoic acid
etikkahappo [Finnish]

Experimental Physico-chemical Properties :

1/_Melting Point :
16.6 °C Alfa Aesar

16.7 °C OU Chemical Safety Data (No longer updated) More details

16.6 °C Alfa Aesar 35566, 35567, 35569, 35572, 38739, 38740, 10994, 33252, 39745, 36289

16.2 °C Oakwood

16 °C Oakwood

16.7 °C FooDB FDB008299

16.2 °C Parchem – fine & specialty chemicals 30201

16.5-16.7 °C Wikidata Q47512

16.6 °C Wikidata Q47512

14-20 °C Wikidata Q47512

61-63 °F (16.1111-17.2222 °C) Wikidata Q47512

62 °F (16.6667 °C) Wikidata Q47512

2/_Boiling Point :
118.1 °C Alfa Aesar

244 °F (117.7778 °C) NIOSH AF1225000

PAGE 3
 118 °C Food and Agriculture Organization of the United Nations Acetic acid

118 °C OU Chemical Safety Data (No longer updated) More details

118.1 °C Alfa Aesar 35566, 35567, 35569, 35572, 38739, 38740, 10994, 33252, 39745, 36289

117-118 °C Oakwood

118 °C FooDB FDB008299

117-118 °C Parchem – fine & specialty chemicals 30201

244 °F / 760 mmHg (117.7778 °C / 760 mmHg) Wikidata Q47512

117.8-118 °C / 760 mmHg Wikidata Q47512

117.7-118.1 C / 101325 mmHg Wikidata Q47512

3/_Lionization Point :
Ev NIOSH AF122500010.66

4/_Vapr Pressure :
11 mmHg NIOSH AF1225000

5/_log P :
-0.17 Egon Willighagen http://dx.doi.org/10.1021/ci050282s

6/_Flash Point :
103 °F (39.4444 °C) NIOSH AF1225000

40 °C OU Chemical Safety Data (No longer updated) More details

104 °F (40 °C) Alfa Aesar 10994, 33252, 39745

40 °C Alfa Aesar 10994, 33252, 39745, 36289

40 °C Oakwood

39 °C Wikidata Q47512

33-45 °C Wikidata Q47512

PAGE 4
 103 °F (39.4444 °C) Wikidata Q47512

102-104 °F (38.8889-40 °C) Wikidata Q47512

7/_Frezzing Point :
62 °F (16.6667 °C) NIOSH AF1225000

8/_Refraction Index :
1.3721 Alfa Aesar 39745, 38740, 38739, 36289, 33252, 10994

1.366-1.377 Food and Agriculture Organization of the United Nations Acetic acid

1.3696 FooDB FDB008299

1.371 Parchem – fine & specialty chemicals 30201

1.371 Sigma-Aldrich SAJ-01-0270

1.3718 Kaye & Laby (No longer updated)

8/_Solubility :
Miscible NIOSH AF1225000

9/_Density :
1.048 g/mL / 20 °C Merck Millipore 818755

1.049 g/mL Alfa Aesar 10994, 33252, 35566, 35567, 35569, 35572, 36289, 38739

1.052 g/mL / 5 °C Merck Millipore 5096

1.049 g/mL Parchem – fine & specialty chemicals 30201

1.0446 g/mL Wikidata Q47512

PAGE 5
Compounds with the same molecular formula :

ID Structure Molecular Formula Molecular Weight

171
C2H4O2 60.052

# of Data Sources:
176
# of References:
16081
# of PubMed:
25018
# of RSC:
50798

7577
C2H4O2 60.052

736
C2H4O2 60.052

PAGE 6
 ID Structure Molecular Formula Molecular Weight

108850
C2H4O2 60.052

2300359
− C2H4O2 60.05196

2300417
− C2H4O2 60.05196

126850
C2H4O2 60.052

91938 C2H4O2 60.052

PAGE 7
 ID Structure Molecular Formula Molecular Weight

394726 C2H4O2 60.052

11226930
− - 0/1 defined C2H4O2 60.052

25934400 C2H4O2 60.052

3018818
− C2H4O2 60.05196

61709519
− - 1/1 defined C2H4O2 60.052

PAGE 8
*compounds with the same skeleton :

171

2006083

2006082

8329490

9357652

PAGE 9
 170

21171080

120608

17339808

17341075

PAGE 10
 144444

21171089

396653

17341230

ARTICULES:
 Tianfang Wang and John H. Bowie. Radical routes to interstellar glycolaldehyde.
The possibility of stereoselectivity in gas-phase polymerization reactions involving
CHO and ˙CHOH, Org. Biomol. Chem., 2010, 8, 4757.

[DOI: 10.1039/c0ob00125b]
 Ágnes Filáry and Attila K. Horváth. Photochemically induced catalysis of iodide ion
and iodine in the tetrathionate–periodate reaction, Phys. Chem. Chem. Phys.,
2010, 12, 6742.

PAGE 11
 [DOI: 10.1039/b921858k]
 Qianfu Luo, Yi Liu, Xin Li and He Tian. Facile synthesis and characterization of
new photochromic trans-dithienylethenes functionalized with pyridines and
fluorenes, Photochem. Photobiol. Sci., 2010, 9, 234.

[DOI: 10.1039/b9pp00088g]
 Nagaprasad Puvvada, Pravas Kumar Panigrahi and Amita Pathak. Room
temperature synthesis of highly hemocompatible hydroxyapatite, study of their
physical properties and spectroscopic correlation of particle size, Nanoscale,
2010, 2, 2631.

[DOI: 10.1039/c0nr00611d]

Reactions :

Chemicals Used

Boric acid (Sigma Aldrich)

Acetic Anhydride (Alfa Aesar)
Acetic Acid (Fisher Scientific)
Toluene (Sigma Aldrich)

Procedure

B(OH)3 (25 g, 0.4 mol), acetic acid (1.25 mL), and toluene (115 mL) were added to a three-necked
round bottom flask equipped with a condenser and a thermometer. The mixture was stirred for
thirty minutes at room temperature before addition of acetic anhydride (116 mL, 1.2 mol). The
reaction temperature was raised to 45 ºC over one hour and then to 60 ºC over one and a half
hours. The mixture was left to stir overnight. When the reaction completed, the cloudy-white
mixture turned clear and the solution was cooled to room temperature. The
precipitated B(OAc)3 was isolated by filtration under dry N2 as white powder (36.95 g, 48 % yield).

Author's Comments

Use freshly opened bottle of acetic anhydride if possible.

PAGE 12
Recently published submissions

One step synthesis of thalidomide.

− Edoardo Bandieri, Emanuel Bruno Savini

Dechlorination followed by hydrolysis of Clobazam

− Heena Beig, Gopala Krishna Rao, Gangadhar Meti, Ramesha
Ramakrishna

Esterification of Monomethyl Fumarate

Bishwajit Chakraborthy, Sayyed Mudassar, Ramesha
Ramakrishna

PAGE 13