Erucamide

HCID 5365371

Grundinformationen

CAS
112-84-5
Standard-SMILES
CCCCCCCC/C=C\CCCCCCCCCCCC(N)=O
InChIKey
UAUDZVJPLUQNMU-KTKRTIGZSA-N
Summenformel
C22H43NO
Durchschnittliche Molmasse
337,6 g/mol
Monoisotopische Masse
337,334465

Überblick

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 an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a mammalian metabolite, a plant metabolite, a human metabolite and a rat metabolite. It is functionally related to an erucic acid.

Namen und Bezeichner

Bevorzugter Name
Erucamide
IUPAC
(Z)-docos-13-enamide
Englischer Name
Erucamide
Summenformel
C22H43NO
Molmasse
337.58

Namen und Synonyme

ERUCAMIDE(Z)-Docos-13-enamide112-84-5ErucylamideErucic acid amideErucyl amidecis-13-Docosenamide13-Docosenamide, (13Z)-13-Docosenamide, (Z)-(Z)-13-Docosenamideplastic additive 13erucilamide
Weitere Namen anzeigen
13-DOCOSENAMIDE13Z-DOCOSENAMIDEERUCIC AMIDECIS-13-DOCOSENOAMIDE
Adogen 58(13Z)-13-Docosenamide0V89VY25BNDTXSID4026929CHEBI:142245204-009-2RefChem:5800DTXCID606929

Datenbank-Bezeichner

CAS
112-84-5
PubChem CID
5365371
DTXSID
DTXSID4026929
ChEMBL
CHEMBL1232565
ChEBI
CHEBI:142245
UNII
0V89VY25BN
EC Number
204-009-2
Nikkaji
J36.612I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
8,8
Polarare Oberfläche (TPSA)
43,1 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
19
Schwere Atome
24

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Amides, Other

Industrial compound

LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> Primary amides [FA0801]
Polymers · 2 Einträge

Plastics -> Polyolefin-I; Polyolefin-II

Plastics -> Other functions -> Slip promoter

CosmeticsOpacifying; Viscosity controlling
Color/FormSOLID
SolubilitySOL IN ISOPROPANOL; SLIGHTLY SOL IN ALCOHOL, ACETONE

Physikochemische Eigenschaften

Schmelzpunkt
75 · 75-85 °C 79-81 °C (lit.)
Siedepunkt
473.86 °C · 473.86°C (rough estimate)
Dichte
0.9417 · 0.9417 (rough estimate)
Dampfdruck
0 · 0-0Pa at 25℃
Brechungsindex
1.5614 · 1.5614 (estimate)
Flammpunkt
230 °C · 230 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 67.1% (429 of 639) of all reports.

Warning

H315 (32.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 639 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 13-Docosenamide, (Z)-

13-Docosenamide, (13Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 13-Docosenamide, (13Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 23-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14899

13-Docosenamide, (13Z)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 13-Docosenamide, (Z)-: Human health tier I assessment
Hazards SummaryMay cause irritation; [MSDSonline]
FDA RequirementsErucamide is an indirect food additive for use only as a component of adhesives.
Hazard Classes and CategoriesSkin Irrit. 2 (32.7%)

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on expected slow hydrolysis(1-2) of erucamide in water, hydrolysis should be unimportant in soil The presence of chromophoric groups in erucamide that are capable of absorbing sunlight(1) suggests that photolysis may be important on soil surfaces. The fact that the erucamide is degradable by fungi(3) indicates that it has the potential to biodegrade in soil, but its rate of biodegradation is unknown. The estimated log Koc of 4.02(1) indicates that erucamide should be immobile in soil(4). The vapor pressure 1.28X10-6 mm Hg at 25 °C estimated from its melting point of 77.5 °C(5) and an estimation method(6,SRC) suggests volatilization from soil should not be important(SRC).

AQUATIC FATE: Hydrolysis of erucamide should not be important in environmental waters(1-2). Based on the available chromophoric group, direct photolysis of erucamide may be important in clear surface water(1). Biodegradation of erucamide may be important in soil(3), but degradation rate data are unknown. The volatilization half-life of erucamide from a model river has been estimated to be 23 days(1-5). Therefore, volatilization from water should not be important(SRC). The estimated log Koc of 4.02(1) indicates that erucamide may strongly adsorb to suspended solid and sediment in water(4). The estimated bioconcentration factor of 6310(1) suggests that bioconcentration of erucamide in aquatic organisms should be important(SRC).

ATMOSPHERIC FATE: Based on the estimated vapor pressure of 1.28X10-6 mm of Hg, erucamide should be found in the atmosphere both in particulate and vapor phase(3). In the atmosphere, vapor phase erucamide should react quickly with photochemically produced hydroxyl radicals and ozone present in the ambient air. Based on an estimation method(1), the rate constant for the reaction of erucamide with hydroxyl radicals has been estimated to be 1.03X10-10 cu-cm/molecule-sec(1). Assuming the daily average concn of hydroxyl radicals in the atmosphere as 5X10+5/cu-cm(2), the half-life for this reaction has been estimated to be 3.7 hrs. Based on an estimation method(4), the rate constant for the reaction of erucamide with atmospheric ozone has been estimated to be 13.0X10-17 cu m/molecule-sec. Assuming the average concn of atmospheric ozone to be 7X10+11 molecules/cu cm(2), the half-lives for these reactions have been estimated to be 2.1 hrs. Particulate erucamide may be removed from the atmosphere by dry deposition(SRC).

Soil Adsorption/Mobility · 1 Eintrag

Based on an estimated water solubility of 0.2 mg/L and a regression equation, a log Koc value of 4.02 has been estimated for erucamide(1). This value indicates that erucamide should be immobile in soil(2) and should remain strongly adsorbed to suspended solids and sediments in water(SRC).

Artificial Pollution SourcesSince erucamide is used as a foam stabilizer, solvent for waxes and resins, and antiblock agent for some plastics(1), the release of erucamide to the environment may occur during production of erucamide and its use(SRC).
Environmental Biodegradation · 1 Eintrag

In a standard ASTM test to assess the biodegradation potential of chemicals, erucamide was found to be readily assimilated by fungi(1). Therefore, biodegradation of erucamide in water and soil may be important, although no rate data for biodegradation under environmental conditions are available(SRC).

Environmental Bioconcentration · 1 Eintrag

The vapor pressure of erucamide has been estimated to be 1.28X10-6 mm Hg at 25 °C from its melting point of 77.5 °C(1) and an estimation method(3). The Henry's Law constant for erucamide has been estimated to be 2.844X10-6 atm-cu m/mole by an estimation method(4). From the ratio of estimated vapor pressure and estimated Henry's Law constant, the water solubility of erucamide has been estimated to be 0.2 mg/L(2). Since erucamide is a long chain aliphatic amide, it is likely to have low water solubility. The low water solubility of erucamide suggests that bioconcentration of the compound in aquatic organisms may be important(2,SRC).

Volatilization from Water/Soil · 1 Eintrag

A Henry's Law constant of 2.844X10-6 atm-cu m/mole has been estimated for erucamide by the bond contribution method(1). Based on this value, the volatilization of erucamide from a model river of depth 1 m, flowing at 1 m/sec and a wind speed of 3 m/sec has been estimated to be 23 days(2). Therefore, volatilization should not be important in water(SRC).

Regulatorische Informationen

FDA RequirementsErucamide is an indirect food additive for use only as a component of adhesives.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
hs_code
29241990
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-37/39

Chemie und Industrie

Pharmakologische Informationen

Mechanism of ActionERUCIC ACID WAS INCORPORATED INTO DIPHOSPHATIDYLGLYCEROL & SPHINGOMYELIN IN HEART & LIVER OF MALE RATS FED ERUCIC ACID FOR 20 DAYS. /EURACIC ACID/

Verwendung und Herstellung

Uses · 4 Einträge

Used as foam stabilizer, adherent, antiblock agent for polyethylenes, and solvent for waxes and resins; [HSDB]

FOAM STABILIZER; SOLVENT FOR WAXES & RESINS; EMULSIONS; ANTIBLOCK AGENT FOR POLYETHYLENE

Used as adherent

Plastics -> Typical concentration range in plastic materials -> 0.1%

U.S. Production · 3 Einträge

2023: 10,000,000 - <25,000,000 lb

(1979) 2.44X10+9 GRAMS

(1980) 2.27X10+9 GRAMS

Consumer UsesFlux agent
Industry UsesLubricating agent
Methods of ManufacturingREACTION OF ERUCIC ACID WITH ANHYDROUS AMMONIA
Use Classification · 3 Einträge

Cosmetics -> Opacifying; Viscosity controlling

Plastics -> Polymer Type -> Polyolefin-I; Polyolefin-II

Plastics -> Other functions -> Slip promoter

Anwendungen · 2 Einträge

BeschreibungErucamide 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

VerwendenErucamide 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.

Darstellung

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

Anbieter100 Anbieter

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