Dodecylmethacrylat

Lauryl Methacrylate

HCID 8906CAS 142-90-5

Grundinformationen

Standard-SMILES
C=C(C)C(=O)OCCCCCCCCCCCC
InChIKey
GMSCBRSQMRDRCD-UHFFFAOYSA-N
Summenformel
C16H30O2
Durchschnittliche Molmasse
254,41 g/mol
Monoisotopische Masse
254,2245802

Namen und Bezeichner

Bevorzugter Name
Lauryl Methacrylate
IUPAC
dodecyl 2-methylprop-2-enoate
Lokaler Name
Dodecylmethacrylat
Englischer Name
Dodecyl Methacrylate
Summenformel
C16H30O2
Molmasse
254.41

Namen und Synonyme

Dodecyl methacrylate142-90-5LAURYL METHACRYLATEDodecyl 2-methylacrylateN-Dodecyl methacrylateMetazene2-Propenoic acid, 2-methyl-, dodecyl esterDodecyl 2-methyl-2-propenoateSipomer LMAMethacrylic acid, dodecyl esterLAMAAgeflex FM 246
Weitere Namen anzeigen
Acrylic Monomer LMAN-LAURYL METHACRYLATEauryLLMA-C12
Methacrylic acid, lauryl esterGE 410 (methacrylate)Caswell No. 521Laurylester kyseliny methakryloveSR 313DTXSID4027103Acrylic acid, 2-methyl-, dodecyl esterAI3-08765

Datenbank-Bezeichner

CAS
142-90-5
PubChem CID
8906
DTXSID
DTXSID4027103
ChEMBL
CHEMBL1903701
UNII
B6L83074BZ
EC Number
205-570-6
Nikkaji
J78.373K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,2
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
13
Schwere Atome
18

Experimentelle und physikochemische Eigenschaften

LogPlog Kow = 6.45
Density · 5 Einträge

0.868 at 77 °F (USCG, 1999) - Less dense than water; will float

0.87 at 77 °F (approx) (USCG, 1999) - Less dense than water; will float

0.868 @ 20 °C

The commercial material is a mixture containing both lower and higher fatty derivatives; boiling range: 272-344 °C; bulk density: 0.868 g/ml

0.868 @ 20°C

SolubilityInsol in water
Flash Point · 3 Einträge

greater than 230 °F (USCG, 1999)

132 °C (Cleveland open cup)

126 °C (closed cup)

Boiling Point142 °C @ 4 mm Hg
DecompositionWhen heated to decomp it emits acrid smoke and fumes.

Physikochemische Eigenschaften

Schmelzpunkt
-7 °C · -7 °C (lit.)
Siedepunkt
142 °C/4 · 142 °C/4 mmHg (lit.)
Dichte
0.868 g/mL · 0.868 g/mL at 25 °C (lit.)
Dampfdruck
0.06 Pa · 0.06Pa at 20℃
Brechungsindex
20 · n20/D 1.445(lit.)
Flammpunkt
230 °F · >230 °F

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P271, P304+P340, P319, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 5% (66 of 1322) of reports.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 2-Propenoic acid, 2-methyl-, dodecyl ester

2-Propenoic acid, 2-methyl-, dodecyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, dodecyl ester 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: 13-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14902

Dodecyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 2 Einträge

Behavior in Fire: Heat can induce polymerization with rapid release of energy. Sealed containers may rupture explosively. (USCG, 1999)

Behavior in Fire: Heat can induce polymerization with rapid release of energy. Sealed contawiners may rupture explosively. (USCG, 1999)

Fire PotentialCombustible
Health Hazards · 2 Einträge

Inhalation temporarily reduces blood pressure from 5 to 25%, increases respiratory rate, decreases heart rate, and causes some EKG changes. Liquid may cause irritation of eyes and skin. May be harmful if swallowed. (USCG, 1999)

Inhalation temporarily reduces blood pressure from 5 to 25%, increases respiratory rate, decreases heart rate, and causes some EKG changes. Liquid may cause irritation of eyes and skin. May be harmful if swallowed. (USCG, 1999)

Hazards Summary · 1 Eintrag

A mild skin and eye irritant in rabbits; [HSDB] May polymerize; May irritate skin and eyes; [CAMEO] A skin and eye irritant; [eChemPortal: ERMA] A skin, eye, and respiratory tract irritant; [eChemPortal: ESIS] An irritant; [MSDSonline] See ACRYLIC RESINS (MONOMERS).

Reactive Group · 2 Einträge

Acrylates and Acrylic Acids;Polymerizable Compounds

Acrylates and Acrylic Acids;Polymerizable Compounds

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents: Foam, CO2 or dry chemical (USCG, 1999)

Fire Extinguishing Agents: Foam, CO2, or dry chemical (USCG, 1999)

First Aid · 2 Einträge

INHALATION: Move victim to fresh air. If breathing has stopped, give artificial respiration. If breathing is difficult, give oxygen.;EYES OR SKIN: Flush with running water for at least 15 min; hold eyelids open if neccessary. Wash skin with soap and water.;INGESTION: If victim is conscious, have victim drink milk or water and induce vomiting. If victim is unconscious or having convulsions, do nothing except keep victim warm. (USCG, 1999)

INHALATION: Move victim to fresh air. If breathing has stopped, give artificial respiration. If breathing is difficult, give oxygen.;EYES OR SKIN: Flush with running water for at least 15 minutes; hold eyelids open if necessary. Wash skin with soap and water.;INGESTION: If victim is conscious, have victim drink water or milk and induce vomiting. If victim is unconscious or having convulsions, do nothing except keep victim warm. (USCG, 1999)

Storage Conditions · 3 Einträge

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/

To avoid photoinitiation of polymerization, all methacrylates should be stored with minimal exposure to light.

The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temp must be kept low to minimize formation of peroxides and other products. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/

Disposal Methods · 1 Eintrag

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 3 Einträge

... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Protective Action Criteria (PAC) · 3 Einträge

72 [mg/m3]

790 [mg/m3]

4800 [mg/m3]

Toxikologische Informationen

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Toxicity Summary · 2 Einträge

Based on available data, the CIR Expert Panel concluded that ... Lauryl Methacrylate is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.

Safe for use in cosmetics, with qualifications

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Acute Exposure/ Methacrylate ester monomer and methacrylic acid decreased the heart rate and force of contraction of the isolated, perfused rabbit heart when added to the perfusing liquid at concentrations of 1:1000, 1:10,000 or 1:100,000 (vol/vol), and most of the cmpd decreased the coronary flow rate. Methacrylic acid, methyl methacrylate, ethyl methacrylate, and dimethylaminoethyl methacrylate produced an irreversible effect on the isolated heart at all 3 concentrations, while 1,3-butylene dimethacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, and lauryl methacrylate produced only a reversible effect at all 3 concentrations.

/LABORATORY ANIMALS: Acute Exposure/ Methacrylic acid administration iv increased respiratory rate, decreased heart rate, and produced electrocardiogram changes in anesthetized dogs. Methacrylic acid, methyl, n-propyl, n-butyl, isobutyl, and hydroxyethyl methacrylates produced a biphasic response, an abrupt fall in blood pressure followed by a secondary rise. 2-ethylhexyl, isodecyl, lauryl, and tert-butylaminoethyl methacrylates produced only a hypotensive effect. Dimethylaminoethylmethacrylate produced only a hypertensive effect.

/LABORATORY ANIMALS: Acute Exposure/ ...To determine the effect of side-chain length on sensitizing potential, we examined 11 derivatives with linear side chains from C1 to C18 in an experimental sensitization test in guinea pigs. The results showed an increase in the sensitizing potential with increasing length of the alkyl side chain from C1 to C12. The C12 derivative, lauryl methacrylate, showed the strongest sensitizing potential.

/LABORATORY ANIMALS: Acute Exposure/ A 500 mg dose over a 24 hr period caused mild irritation to skin and eyes of rabbits. /from table/

For more Non-Human Toxicity Excerpts (Complete) data for N-DODECYL METHACRYLATE (6 total), please visit the HSDB record page.

Antidote and Emergency Treatment · 2 Einträge

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

Non-Human Toxicity Values · 5 Einträge

LD50 Rat oral >5.0 g/kg

LD50 Rabbit percutaneous >3.0 g/kg

LD50 Rat ip 21.6 g/kg

LD50 Mouse oral >87,250 mg/kg

For more Non-Human Toxicity Values (Complete) data for N-DODECYL METHACRYLATE (6 total), please visit the HSDB record page.

Regulatorische Informationen

Regulatory Information · 4 Einträge

Chemical: 2-Propenoic acid, 2-methyl-, dodecyl ester

2-Propenoic acid, 2-methyl-, dodecyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, dodecyl ester 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: 13-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14902

Dodecyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 3082 9/PG 3
hs_code
29161490
RTECS-Nr.
OZ4300000
risk_code
36/37/38-50/53

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme A derivative, which then enters the normal lipid metabolism. /Methacrylates/

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity. /Methacrylates/

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Lauryl Methacrylate

Used as monomer (plastics, molding powders, solvent coatings, adhesives, oil additives, viscosity index improvers, and pour-point depressants for distillate fuels), softener for lacquers, and industrial deodorant for methyl sulfide odors; Used in emulsions (textile, leather, and paper finishing) and insecticides (delay volatilization); [HSDB]

Pulp and Paper Processing [Category: Industry];Painting (Pigments, Binders, and Biocides) [Category: Paint];Farming (Pesticides) [Category: Industry];Plastic Composites Manufacturing [Category: Industry];Leather Tanning and Processing [Category: Industry];Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

For N-dodecyl methacrylate (USEPA/OPP Pesticide Code: 053101) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Polymerizable monomer for plastics, molding powders, solvent coatings, adhesives, oil additives; emulsions for textile, leather, and paper finishing.

As a deodorant to mask methyl sulfide odors in industry.

U.S. Production2023: 10,000,000 - <50,000,000 lb;2022: 10,000,000 - <50,000,000 lb;2021: 25,000,000 - <40,000,000 lb;2020: 10,000,000 - <50,000,000 lb
Consumer UsesMonomers;Hydraulic fluids
Industry UsesHydraulic fluids;Not Known or Reasonably Ascertainable;Photosensitive chemicals;Viscosity modifiers;Adhesion/cohesion promoter;Intermediate;Monomers
Methods of Manufacturing · 2 Einträge

The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/

... Manufactured by direct esterification of methacrylic acid or transesterification of methyl methacrylate.

Formulations/PreparationsThe commercial material is a mixture, containing also lower and higher fatty derivatives.
Anwendungen · 1 Eintrag

VerwendenMiniemulsion polymerization of laurel methacrylate has been reported. Atom transfer radical polymerization and consecutive block copolymerization with methyl methacrylate has been investigated. Preparation of LMA based monolithic columns for CEC has been reported. LMA is used as a co-stabilizer to retard Ostwald ripening effect.

Vor- und nachgelagerte Produkte

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