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.

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.

Definition

ChEBI: 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.

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.