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Date/Time:  10/10/19 6:42 GMT
 

Cinnamonitrile

Linear Formula C6H5CH=CHCN
Molecular Weight 129.16
Purity: ≥98%
Beilstein Registry Number 1209546
EC Number 217-552-5

Appearance: Colorless to yellowish liquid, the aroma is very similar to natural
cinnamon, with strong spicy fragrance.
Melting point: 18-20°C(lit.)
Boiling point: 254-255 °C(lit.)
Density : 1.028 g/mL at 25 °C(lit.)
Flash Point(C): 113°C
refractive index : n20/D 1.601(lit.)

Preparation
The aqueous solution of hydroxylamine hydrochloride and sodium carbonate was
prepared by mixing anhydrous sodium carbonate, hydroxylamine hydrochloride and
water. Then the aqueous solution of hydroxylamine hydrochloride and sodium
carbonate was added to the solution of cinnamaldehyde and ethanol or methanol,
stirred and set it well. Then the reaction mixture was poured into the ice water
until the white precipitate was precipitated, the white precipitate was filtered
out and washed with water, then the cinnamaldehyde oxime was obtained after
drying. Acetic anhydride of 2o 2.5 times (mole ratio) was dripped into
cinnamaldehyde oxime, stirred for dehydration and cooled, then vacuum distillation
was used to recover acetic anhydride and acetic acid produced by the reaction, and
then vacuum distillation was carried out. Cinnamonitrile was obtained by
collecting stable fractions at 130C / 2064pa or 151.0 ℃ / 5330pa. The method has
the advantages of simple operation, low raw material, no pollution and high yield.

Rapid Synthesis of Trans-cinnamonitrile
Acetonitrile, potassium hydroxide and benzaldehyde were used as raw materials in
acetonitrile solvent, stirred and refluxed (10 min), hydrolyzed by crushed ice,
heated under normal pressure and distilled under reduced pressure to rapidly
synthesize trans-cinnamonitrile. The yield was 48%-54%. The application of organic
carbon anion nucleophilic addition reaction mechanism in organic synthesis was
studied. The structure of the product was characterized by UV-Vis, FTIR and HNMR,
and it was confirmed that the product was the target product. The results showed
that trans cinnamonitrile could be synthesized rapidly under mild conditions using
potassium hydroxide benzaldehyde and acetonitrile as raw materials according to
the mechanism of nucleophilic addition of organic carbon anion.

Usage:
The performance is stable under alkaline condition. No toxic side effects to human
body, no irritation to the skin, no allergic reaction. Cinnamonitrile is an ideal
substitute for cinnamon oil and cinnamaldehyde. Widely used in cosmetics, spice,
laundry powder and other daily necessities and soap spices. It has good inhibition
effect on mold, wide inhibition spectrum and insect repellent effect. At the same
time, it is also used in medicine, fine chemical products. It's a good synthetic
product.

Authoritative research:
the Institute of Aquatic Biology of the Chinese Academy of Sciences has isolated
cinnamonitrile against phytopathic and dermatophilic bacteria and 18 of the most
common grains. The inhibitory effects of 4 kinds of fruit isobaric fungi on human
superficial filamentous bacteria were studied. The results showed that
cinnamonitrile had high bactericidal activity and was a broad spectrum
bactericidal compound.
Cinnamonitrile
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