基本情報
- 標準SMILES
C=C(C)C(=O)OCCCCCCCCCCCC- InChIKey
GMSCBRSQMRDRCD-UHFFFAOYSA-N- 分子式
- C16H30O2
- 平均分子量
- 254.41 g/mol
- 単同位体質量
- 254.2245802
名称と識別子
- 優先名称
- Lauryl Methacrylate
- IUPAC
- dodecyl 2-methylprop-2-enoate
- 現地名
- メタクリル酸ドデシル
- 英語名
- Dodecyl Methacrylate
- 分子式
- C16H30O2
- 分子量
- 254.41
名称と別名
名称をさらに表示
データベース識別子
- CAS
142-90-5- PubChem CID
- 8906
- DTXSID
DTXSID4027103- ChEMBL
CHEMBL1903701- UNII
- B6L83074BZ
- EC Number
- 205-570-6
- Nikkaji
- J78.373K
物性
構造計算による物性
- XLogP
- 7.2
- 極性表面積
- 26.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 13
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 221
実験および物理化学的性質
Density
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
Flash Point
greater than 230 °F (USCG, 1999)
132 °C (Cleveland open cup)
126 °C (closed cup)
Melting Point
-8 °F (USCG, 1999)
-20 °C
Molecular weight: 262; melting point: -22 °C; /Made from a mixture of higher alcohols, predominately C-12/
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/
Vapor Pressure
0.00118 [mmHg]
0.0012 mm Hg @ 25 °C /Estimated/
0.0012 [mm Hg] @20 °C
Physical Description
Dodecyl methacrylate is a liquid. Floats on water. (USCG, 1999)
Dodecyl/pentadecyl methacrylate is a colorless liquid. Less dense than water and insoluble in water. A mixture of esters of methacrylic acid. (USCG, 1999)
Liquid
Liquid; [CAMEO] Clear colorless liquid; [MSDSonline]
物理化学的性質
- 融点
- -7 °C · -7 °C (lit.)
- 沸点
- 142 °C/4 · 142 °C/4 mmHg (lit.)
- 比重(密度)
- 0.868 g/mL · 0.868 g/mL at 25 °C (lit.)
- 蒸気圧
- 0.06 Pa · 0.06Pa at 20℃
- 屈折率
- 20 · n20/D 1.445(lit.)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- 2 · Inert atmosphere,2-8°C
- 溶解性
- Chloroform (Slightly), Methanol (Slightly)
- 外見
- 液体
- 色
- クリアライトイエロー
- 水溶解度
- 不溶性
- BRN
- 1708160 · 1708160
- 化粧品成分の機能
- 粘度制御
- InChI
- 1S/C16H30O2/c1-4-5-6-7-8-9-10-11-12-13-14-18-16(17)15(2)3/h2,4-14H2,1,3H3
- InChIKey
- GMSCBRSQMRDRCD-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCCCCOC(=O)C(C)=C
- LogP
- 6.68 at · 6.68 at 20℃
- CAS データベース
- 142 · 142-90-5(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · 2-Propenoic acid, 2-methyl-, dodecyl ester(142-90-5)
- EPAの化学物質情報
- Lauryl methacrylate (142-90-5)
化学的性質
化学的特性clear colorless to yellowish liquid
安全と法規制
GHS分類
GHS Classification
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.
危険有害性情報
Regulatory Information
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
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)
Health Hazards
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
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
Acrylates and Acrylic Acids;Polymerizable Compounds
Acrylates and Acrylic Acids;Polymerizable Compounds
Reactivity Alerts
Polymerizable
Polymerizable
Reactivity Profile
DODECYL METHACRYLATE is an acrylate ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Tends to polymerize. Oxidizing and reducing agents may initiate polymerization. Reaction may also occur when heated (USCG, 1999).
DODECYL/PENTADECYL METHACRYLATE reacts with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. Tends to polymerize. Oxidizing and reducing agents may initiate polymerization. Polymerization may also occur when heated (USCG, 1999).
Air and Water Reactions
No rapid reaction with air. No rapid reaction with water.
Insoluble in water.
Hazard Classes and Categories
Skin Irrit. 2 (87.6%);Eye Irrit. 2 (87.6%);STOT SE 3 (95%);Aquatic Acute 1 (83.3%);Aquatic Chronic 1 (84.3%)
Specific target organ toxicity (single exposure) - category 3
Serious eye damage/eye irritation - Category 2B
STOT SE 3
安全と保護具
Fire Fighting
Fire Extinguishing Agents: Foam, CO2 or dry chemical (USCG, 1999)
Fire Extinguishing Agents: Foam, CO2, or dry chemical (USCG, 1999)
First Aid
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
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
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
... 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)
72 [mg/m3]
790 [mg/m3]
4800 [mg/m3]
Personal Protective Equipment (PPE)
Wear self-contained positive pressure breathing apparatus and full protective clothing. (USCG, 1999)
Wear self-contained positive pressure breathing apparatus and full protective clothing. (USCG, 1999)
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/
毒性情報
Toxicity Summary
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
/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
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 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.
法規制情報
Regulatory Information
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
安全データ
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- OZ4300000
- ridadr
- UN 3082 9/PG 3
- hs_code
- 29161490
- risk_code
- 36/37/38-50/53
- 化審法
- (2)-1039
- 消防法
- 危-4-3-III
- hazard_code
- Xi,N
- safety_code
- 26-28-60-61-28B
- hazard_class
- 9
- packing_group
- III
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 10 - Combustible liquids
- 有毒物質データの
- 142-90-5(Hazardous Substances Data)
化学と産業
薬理情報
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 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/
用途と製造
Uses
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.
Methods of Manufacturing
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.
Use Classification
Fragrance Ingredients
Cosmetics -> Viscosity controlling
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing;Other (requires additional information);Paint and Coating Manufacturing;Plastics Material and Resin Manufacturing;All Other Chemical Product and Preparation Manufacturing;Adhesive Manufacturing;Petroleum Lubricating Oil and Grease Manufacturing;Printing and Related Support Activities
2-Propenoic acid, 2-methyl-, dodecyl 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/
応用分野
用途潤滑油添加剤,繊維処理剤,塗料?接着剤原料,紙コーティング剤
用途合成樹脂原料。
使用Miniemulsion 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.
一般的な説明Liquid. Floats on water.
調製方法
Putting the main ingredients of dodecanol and methacrylic acid into an esterification reaction vessel, adding a solvent (toluene or xylene), adding a catalyst (phosphoric acid or p-toluenesulfonic acid), adding an inhibitor A (copper chloride), stirring the reaction, and obtaining a reaction material. The esterification reaction vessel is evacuated, the pressure in the esterification reaction vessel is controlled to be -0.04~-0.08Mpa, the temperature in the esterification reaction vessel is increased until reflux liquid flows out, and the temperature is kept until no reflux liquid flows out or until the acid value in the reaction solution is detected to be 30~50mgKOH/g. Then the temperature is lowered to room temperature. The reaction material is transferred to a water washing container, an alkali solution is added, the pH value of the reaction material is controlled to be 7~8, and the reaction material is allowed to stand. After the reaction material is layered, the wastewater in the lower layer is discharged. The reaction material without wastewater is transferred to a distillation container, the inhibitor B (2-tert-butyl-4-methylphenol) is added, the distillation container is evacuated, and toluene is removed by distillation to obtain the product.
純化方法Purify the ester by fractional distillation in a high vacuum. Add 0.05% of hydroquinone monomethyl ether as stabilizer. [Rehberg & Fischer Ind Eng Chem 40 1430 1948, Beilstein 2 III 1290, 2 IV 1528.]
上流・下流製品情報
上流原料
サプライヤー50 社
補足説明
定義本品は、メタクリル酸とラウリルアルコール(*)のエステルであり、次の化学式で表される。参照表示名称:ラウリルアルコール
関連反応
関連ノート
読み込み中…