ACETANILIDE

C6H5NHCOCH3

From Aniline and Acetic Acid

Reactor Filter Crystallizer Centrifuge Dryer

Aniline
Acetic Acid
Acetanilide

Waste

Reaction :
C6H5NH2 (l) + CH3COOH (l) → C6H5NHCOCH3 (s) + H2O (l)
90% yield

Material Requirements
Aniline 1500 lb
Acetic Acid (glacial) 1200 lb
Process
Acetanilide is made by reacting anline with acetic acid. The resulting crystalline product is
purified by crystallization.
Aniline and acetic acid are charged to a jacketed, enameled-steel reaction vessel and
refluxed for 6-14 hr until no free aniline remains. If dilute acetic acid is used the reaction is carried
out at 150 to 160 0C. When the reaction is completed the product is filtered hot, then cooled,
crystallized, centrifuged, washed, and dried. If a USP grade is required, the wet centrifuged product
may be purified by recrystallization. In either case the mother liquor may be re-used in future
batches until it adversely affects product quality.
In one process variation, aniline is first charged to a reactor and heated to boiling. Acetic
acid anhydride is added slowly to the boiling aniline. In this way, raction takes places under
nonoxidizing conditions over a 6-hr period at 110-120 0C.
 When acetic anhydride is used, the reaction is carried out in a benzene solution. The
anhydride is used in about 150 percent access.
Use Pattern
Medical
Dyes and dye intermediates
Rubber accelerator
Peroxide stabilizer
Lacquers
Miscellaneous
Properties White or cream flakes or powder
Mol wt. 135,16 M.P.
Sp. gr. 1,21 40C/4 B.P.
Soluble in alcohol, eter, and benzene. Slightly soluble in water (6,1 g/1 kg at
0
80 C)
Grades. Technical (95 to 99 percent; setting point, 1120C min), USP (mp, 1140C min).
Containers and regulations. Boxes (25 lb), bags, drums of various size, and barrels.

Economic Aspects
The chief uss of acetanilide are as a dye intermediate and as a medicinal. The first-
mentioned use may be generally classified as a noncompetitive one. In the medicinal field,
however, this is not so. Acetanilide, known pharmaceutically as “antifebrine” has been widely used
for years as an analgesic (pain reliever) and an antipyretic (fever reducer). Accordingly, it is a
common constituent of proprietary headache remedies. In this field it competes with aspirin and
the other salicylates.
The particular process used in manufacture would appear to depand both on the patent
situation and the economics of dilute acid vs glacial acid and acetic anhydride at a given
manufacturer’s location. All of the current producers are either manufacturers of aniline or a broad
line of intermediates. Usually the acetanlide plant can be used alternately for the manufacture of
other intermediates.
Rangkuman proses menurut buku Faith, Keyes, 1975 :
Asetanilida dibuat dengan mereaksikan anline dengan asam asetat. Produk kristal yang
dihasilkan dimurnikan dengan kristalisasi. Anilin dan asam asetat dibebankan ke reaktor alir tangki
berpengaduk selama 6-14 jam. Jika asam asetat digunakan, reaksi dilakukan pada 150 sampai 160
0
C. Ketika reaksi selesai, produk disaring, kemudian didinginkan, dikristalisasi, disentrifugasi,
dicuci, dan dikeringkan. Dalam kasus tersebut, mother liquor dapat digunakan kembali dalam
batch berikutnya sampai mempengaruhi kualitas produk.
 Dalam satu variasi proses, anilin pertama-tama diisi ke reaktor dan dipanaskan sampai
mendidih. Asam asetat anhidrida ditambahkan perlahan ke anilin mendidih. Dengan cara ini, raksi
terjadi dalam kondisi tidak teroksidasi selama periode 6 jam pada 110-120 0C. Ketika anhidrida
asetat digunakan, reaksi dilakukan dalam larutan benzena. Anhidrida digunakan dalam akses
sekitar 150 persen.
Perbedaan :
Dalam perancangan pabrik Asetanilida yang dirancang, keluaran reaktor yang seharusnya
di filter dengan menggunakan panas / titik didih terlebih dahulu tidak dilakukan, tetapi di lakukan
setelah keluaran centrifuge dengan alat menara distilasi.

Spesifikasi Produk :
Sifat fisis menurut Yaws, 2006; MSDS, 2018; dan HMDB, 2018; Faith 1975

Rumus molekul : C6H5NHCOCH3

Fase : Padat
Berat molekul : 135,17 g/mol
Densitas : 1,22 g/cm³
Temperature kritis : 551.85 oC
Tekanan kritis : 36.8 atm
Tekanan Uap : Not applicable
Kelarutan : 6.39 mg/mL pada 25 °C
Titik beku (1 atm) : 114 oC
Titik didih (1 atm) : 303.8 oC
Bentuk : Serpihan atau bubuk putih atau krem
Wadah : Kotak (25 lb), tas, drum dengan berbagai ukuran, dan tong.
Kadar : Asetanilida teknis memiliki kadar 95 hingga 99 persen
Titik kristalisasi : 60 – 110 0C
Larut dalam alkohol, eter, dan benzena. Sedikit larut dalam air (6,1 g / 1 kg pada suhu 800C)