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Home > Encyclopedia > Erucamide

Erucamide

Erucamide structure

Erucamide 

structure
  • CAS No:

    112-84-5

  • Formula:

    C22H43NO

  • Chemical Name:

    Erucamide

  • Synonyms:

    13-Docosenamide,(13Z)-;Erucamide;13-Docosenamide,(Z)-;(13Z)-13-Docosenamide;cis-13-Docosenamide;Erucic acid amide;Erucyl amide;Diamid L 200;Kemamide E;Adogen 58;Erucic amide;Armid E;Alflow P 10;Armoslip EPX;Crodamide ER;Loxamid E;Crodamide E;Armoslip E;Erucoyl amide;Kemamide E Ultra;Neutron S;Unislip 1753;Armoslip EXP;Alflow 10;Amide E;E 10;E 10 (amide);NewS;Fatty Amide E;Atmer SA 1753;Struktol TR 131;TEP BP-SL 1;RX 4515;Ampacet 10090;Chemstat HTSA 22;Proaid AC 18E;Atmer SA 1753FD;SA 1753FD;Lutamide ER;PEX-SLT 01;Atmer 1753;Chemstat HTSA 22-20M;WK 1890;Pinnacle 2530;Finawax ER;Kemamide E Ultrabead;MB-S 1519;Finawax E;L 300;L 300 (amide);CESA PPA 0050079;Loxiol E SPEZ P;TR 131;P 10;HC 102BF;E 828262;Kao Fatty Amide E;SL 05068PP;Crodamide ER-CH-BE;Chamide SEA;SHHY-A 003;CHMP E 50;SCC 88953;Innoslip E;Crodamide ER-CH-MB-SI;JT 1;JT 1 (amide);KT 0340;80399-99-1;93050-58-9;116749-29-2;2418524-10-2

  • Categories:

    Cosmetic Ingredient  >  Viscosity Controlling

Description

DryPowder; DryPowder, PelletsLargeCrystals; OtherSolid; PelletsLargeCrystals


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 derives from an erucic acid.

Erucamide Basic Attributes

337.58300

337.58

204-009-2

0V89VY25BN

DTXSID4026929

SOLID

2924199090

Characteristics

43.09000

8.8

DryPowder; DryPowder, PelletsLargeCrystals; OtherSolid; PelletsLargeCrystals

0.874 g/cm3

75-80 °C

474.2ºC at 760 mmHg

240.6ºC

1.469

SOL IN ISOPROPANOL; SLIGHTLY SOL IN ALCOHOL, ACETONE

0-6ºC

Safety Information

NONH for all modes of transport

1

R36/37/38

26-36-37/39

Xi

Stable. Incompatible with strong oxidizing agents.

P261-P305 + P351 + P338

H315-H319-H335

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

|Warning|H315 (99.62%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 689 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Since 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).

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).

Amides are generally susceptible to chemical hydrolysis, but most amides without electronegative substituent on carbon or nitrogen hydrolyze extremely slowly(2). Erucamide contains chromophoric group amenable to absorption of light at wavelengths greater than 290 nm(1). Therefore, photolysis of erucamide by sunlight may be important, but rates of photolysis are unknown. The rate constant for the reaction of vapor phase erucamide with hydroxyl radicals has been estimated to be 1.03X10-10 cu-cm/molecule-sec for the cis-isomer by an estimation method(3,SRC). Assuming the daily average concn of hydroxyl radicals in the atmosphere of 5X10+5/cu-cm(4), the half-life for this reaction has been estimated to be 3.7 hrs. The rate constants for the reaction of vapor phase erucamide with atmospheric ozone have been estimated to be 13.0X10-17 cu-cm/molecule-sec(5,SRC). Assuming the daily average atmospheric concn of ozone to be 7X10+11 molecules/cu-cm(5), the half-life has been estimated to be 2.1 hrs(SRC).

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).

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).

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).

Workers using erucamide during use as a foam stabilizer, solvent for fats and waxes, and antiblock agent for plastics are the most likely people for exposure to this compound(1,SRC). NIOSH (NOES Survey 1981-1983) has statistically estimated that 34,861 workers are potentially exposed to erucamide in the USA(2).

Drug Information

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

13-docosenamide

Erucamide Use and Manufacturing

Methods of Manufacturing

REACTION OF ERUCIC ACID WITH ANHYDROUS AMMONIA

Uses

Used for various polyethylene and polypropylene film packaging bags such as food and clothing as opening agent, various plastic product lubricants, release agents and stabilizers for PP production; used for synthetic use of photosensitive materials as an acid-sensitive arm Poly(p-phenoxyethylene), as a new type of carrier, has a wide range of applications in solid-phase peptide synthesis. Mainly used as an excellent lubricant for polyvinyl chloride, polyethylene and polypropylene extruded films. Adding about 0.1% erucamide to the resin can speed up the extrusion speed, and the product will be slippery after molding, which can effectively prevent the adhesion of the elements between the films and facilitate the operation. At the same time, the plastic has antistatic properties. This product is also used as a dispersant for metal protective films, pigments and dyes, additives for printing inks, fiber finishes, release agents, rubber compounding agents, etc. Because it is non-toxic, it is allowed to be used in food packaging materials.


Adhesives and sealant chemicals


Building/construction materials not covered elsewhere

Production

10,000,000 - 50,000,000 lb|(1979) 2.44X10+9 GRAMS|(1980) 2.27X10+9 GRAMS

Adhesive manufacturing|13-Docosenamide, (13Z)-: ACTIVE

Fatty Acyls [FA] -> Fatty amides [FA08] -> Primary amides [FA0801]|Cosmetics -> Opacifying; Viscosity controlling

Computed Properties

Molecular Weight:337.6
XLogP3:8.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:19
Exact Mass:337.334464995
Monoisotopic Mass:337.334464995
Topological Polar Surface Area:43.1
Heavy Atom Count:24
Complexity:286
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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