Erucamide Property

Melting point:

75-85 °C 79-81 °C (lit.)

Boiling point:

473.86°C (rough estimate)

Density 

0.9417 (rough estimate)

vapor pressure 

0-0Pa at 25℃

refractive index 

1.5614 (estimate)

Flash point:

230 °C

storage temp. 

-20°C

solubility 

Soluble in DMSO (up to at lease 40 mg/ml) or in Water (up to at least 25 mg/ml with warming)

form 

solid

pka

16.61±0.40(Predicted)

color 

Off-white

Water Solubility 

PRACTICALLY INSOLUBLE

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

UAUDZVJPLUQNMU-KTKRTIGZSA-N

LogP

8

CAS DataBase Reference

112-84-5(CAS DataBase Reference)

NIST Chemistry Reference

13-Docosenamide, (z)-(112-84-5)

EPA Substance Registry System

13-Docosenamide, (13Z)- (112-84-5)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

1

HS Code 

29241990

Hazardous Substances Data

112-84-5(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Erucamide Chemical Properties,Usage,Production

Description

Erucamide is also known as 13-Docosenamide or Erucylamide. It is in the form of white flakes or beads. It is soluble in isopropanol, slightly soluble in alcohol and acetone.¹ In industry, cis-13-docosenoamide is used in the formulations of anti-adhesive agents, lubricants, and lubricant additives to reduce their friction coefficient and to make films easier to handle.² It is used as a standard to determine fatty acid amides in polyethylene packaging film by GC/MS.³

Chemical Properties

Erucamide is a fatty acid amide derived from erucic acid, which is found in vegetable oil. It is a odorless waxy solid that can dissolve in isopropanol and has low solubility in alcohol and acetone. It is also combustible. Its molecular structure consists of a long unsaturated C22 chain and a polar amine group, which gives it strong surface polarity, a high melting point, and good thermal stability. Because of these properties, it finds extensive applications in industries such as plastics, rubber, printing, and machinery.

Uses

Erucamide is primarily used as a polymer additive, with plastic additive 21 is a plasticizer; used in preparation of natural mineral modified degradable polymer flame-retardant composite material.

Definition

Erucamide is a primary fatty amide resulting from the formal condensation of the carboxy group of erucic acid with ammonia. It is commonly used as a slip additive in the plastic manufacturing industry. It has a role as a human metabolite, a rat metabolite, a mammalian metabolite, a plant metabolite and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is functionally related to an erucic acid.

Preparation

Erucamide is prepared by reaction of erucic acid with anhydrous ammonia. The reaction of erucic acid with anhydrous ammonia is as follows: C22H42O2 + NH3 → C22H43NO2.

General Description

Erucamide is a migratory additive that is commonly placed in polyolefin films to reduce their coefficient of friction (COF), a good attribute for high speed packaging operations.

Biological Activity

13-Docosenamide is the amide of docosenoic acid. It was first identified in the cerebrospinal fluid of sleep-deprived cats. It has also been detected in the cerebrospinal fluid of rats and humans. 13-Docosenamide causes reduced mobility and slightly lessened awareness in rats, whereas 9-octadecenamide induces physiological sleep.

References

[1] MIAO-MIAO LI . Antidepressant and anxiolytic-like behavioral effects of erucamide, a bioactive fatty acid amide, involving the hypothalamus–pituitary–adrenal axis in mice[J]. Neuroscience Letters, 2017, 640: Pages 6-12. DOI:10.1016/j.neulet.2016.12.072.
[2] LIEROP B V, CASTLE L, FEIGENBAUM A, et al. Spectra for the Identification of Additives in Food Packaging[C]. 1998: 0. DOI:10.1007/978-94-011-5222-8.
[3] https://pubchem.ncbi.nlm.nih.gov/compound/Erucylamide#section=Use-and-Manufacturing
[4] https://www.sigmaaldrich.com/catalog/product/aldrich/280577?lang=de&region=DE
[5] I. QUIJADA-GARRIDO. Desorption of Erucamide Vapor in Vacuum from Erucamide/Isotactic Polypropylene Films 1[J]. Macromolecules, 1996, 29 27: 8791-8797. DOI:10.1021/ma961065i.