Grundinformationen
- Standard-SMILES
C=C(C)C(=O)OCCCCCCCC(C)C- InChIKey
COCLLEMEIJQBAG-UHFFFAOYSA-N- Summenformel
- C14H26O2
- Durchschnittliche Molmasse
- 226,35 g/mol
- Monoisotopische Masse
- 226,19328007
Überblick
Isodecyl methacrylate is a clear liquid. (NTP, 1992)
Namen und Bezeichner
- Bevorzugter Name
- Isodecyl methacrylate
- IUPAC
- 8-methylnonyl 2-methylprop-2-enoate
- Lokaler Name
- Isodecylmethacrylat
- Englischer Name
- ISO-DECYL METHACRYLATE
- Summenformel
- C14H26O2
- Molmasse
- 226.36
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
142600-07-5、29964-84-9- PubChem CID
- 34763
- DTXSID
DTXSID60881155- ChEMBL
CHEMBL3187369- UNII
- 7G47103FGX
- EC Number
- 249-978-2
- Nikkaji
- J48.652C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,8
- Polarare Oberfläche (TPSA)
- 26,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 16
- Formalladung
- 0
- Komplexität
- 207
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 5.62 /Estimated/
4.92
Density
0.878 at 68 °F (NTP, 1992) - Less dense than water; will float
0.878 g/cu cm @ 25 °C/5 °C
Flash Point
249.8 °F (NTP, 1992)
121 °C (Cleveland open cup)
Boiling Point
259 °F at 10 mmHg (NTP, 1992)
120 °C @ 0.4 kPa (3 mm Hg)
Polymerization
Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. None the less, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/
Polymerization may be initiated by contamination with peroxides, azo compounds, heavy metal ions, tert amines, /sulfur/ compounds. Polymerization is also induced by light. Atmospheric oxygen saturation in the monomer is necessary for stability.
Vapor Pressure
0.01 [mmHg]
0.012 mm Hg @ 25 °C /Estimated/
Physical Description
Isodecyl methacrylate is a clear liquid. (NTP, 1992)
Liquid
Clear liquid; [CAMEO]
Physikochemische Eigenschaften
- Schmelzpunkt
- -22 °C · -22°C
- Siedepunkt
- 126 °C10 · 126 °C10 mm Hg(lit.)
- Dichte
- 0.878 g/mL · 0.878 g/mL at 25 °C(lit.)
- Dampfdruck
- 1.56 Pa · 1.56Pa at 25℃
- Brechungsindex
- 20 · n20/D 1.443(lit.)
- Flammpunkt
- 230 °F · >230 °F
- Aggregatzustand
- Liquid
- Wasserlöslichkeit
- 199 μg/L · 199μg/L at 20℃
- InChI
- 1S/C14H26O2/c1-12(2)10-8-6-5-7-9-11-16-14(15)13(3)4/h12H,3,5-11H2,1-2,4H3
- InChIKey
- COCLLEMEIJQBAG-UHFFFAOYSA-N
- SMILES
- CC(C)CCCCCCCOC(=O)C(C)=C
- EPA chemische Informationen
- Isodecyl methacrylate (29964-84-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 67.7% (441 of 651) of all reports.
Warning
H315 (23.5%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 651 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: 2-Propenoic acid, 2-methyl-, isodecyl ester
2-Propenoic acid, 2-methyl-, isodecyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, isodecyl 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: 04-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14316
Isodecyl methacrylate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Reactivity Profile
ISODECYL METHACRYLATE may react vigorously with oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, can undergo very exothermic addition polymerization reactions. May undergo autoxidation upon exposure to the air to form explosive peroxides.
Sicherheit und Schutzausrüstung
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Storage Conditions
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/
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Disposal Methods
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
Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed.
When designing a safe plant, among other important considerations, it is necessary to be aware of the considerable exothermic heat generated in some reactions. Thus, high pressure and temperatures may develop. Dangerous exposures can be avoided with careful design such as completely enclosing those processes where toxic chemicals or intermediates occur.
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.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Suitable protective clothing and self-contained respiratory protective apparatus should be available for use of those who may have to rescue persons overcome by fumes. /acrylic acid and derivatives/
Toxikologische Informationen
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ Methacrylic acid administration iv increased respiratory rate, decreased heart rate, & 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: Developmental or Reproductive Toxicity/ ... Six types of methacrylate esters /were admin/ to pregnant rats on days 5, 10 and 15 of gestation in doses up to one-third the acute intraperitoneal LD50. The maximum doses used were 0.44, 0.40, 0.78, 0.46 and 0.82 ml/kg for the methyl, ethyl, n-butyl, isobutyl, isodecyl methacrylate respectively. Hemangiomas were increased at the highest doses as were resorptions. The fetal wt was reduced by treatment. Acrylic acid was injected in volume of up to 0.0075 ml/kg and this was associated with resorptions and hemangiomas. Fetal mortality and an incidence of up to 16% malformations were reported ... .
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... Embryofetal toxicity and teratogenic effects of a group of methacrylic esters in rats /were studied/. The esters studied included methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, and isodecyl methacrylate. Esters were administration at 1/10, 1/5 and 1/3 LD50 dose on 5th, 10th, 15th days of gestation. ... Each ester produced some or all of the following effects: resorptions, gross and skeletal malformations, fetal death or decreased size. Since the chemical was admin ip, it is possible that the toxic effects were due directly to the chemical's passing into the embryo, rather than through systemic absorption.
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Animal studies using rats revealed that some acrylates and methacrylates are embryotoxic. The doses of monomers used in the animal studies, however, were much higher than concentrations likely encountered by workers. /Acrylates and Methacrylates/
For more Non-Human Toxicity Excerpts (Complete) data for ISODECYL METHACRYLATE (6 total), please visit the HSDB record page.
Antidote and Emergency Treatment
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
LD50 Mouse ip 3688 mg/kg
LD50 Rat ip 2467 mg/kg
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 3082 9 / PGIII
- RTECS-Nr.
- OZ5000000
- risk_code
- 36/37/38-43-50/53
- hazard_code
- Xi,N
- safety_code
- 26-36-61-60
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 29964-84-9(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme 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
Used as monomer for acrylic polymers; May find uses in waterproofing concrete, such as highway bridge decks; [HSDB]
Plastic Composites Manufacturing [Category: Industry]
MONOMER FOR ACRYLIC POLYMERS.
Concrete can also be made water-repellent by the polymerization of vinyl monomers on the surface. A treatment that may be practical for highway bridge decks is the application of methyl methacrylate, isodecyl methacrylate, or isobutyl methacrylate.
Methods of Manufacturing
ACID CATALYZED ESTERFICATION OF METHACRYLIC ACID WITH ISODECANOL; TRANSESTERIFICATION OF METHYL METHACRYLATE WITH ISODECANOL IN PRESENCE OF CATALYST
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/
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
2-Propenoic acid, 2-methyl-, isodecyl ester: ACTIVE
METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/
Anwendungen
VerwendenIsodecyl Methacrylate is a reagent used in the preparation of Janus particles which act as solid surfactants.
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