化工社化工社 化学情報印刷レポート · 研究参考用
メタクリル酸ドデシル
メタクリル酸ドデシル · LAM · メタクリル酸ラウリル · ラウリルメタクリレート · ドデカン-1-イル＝メタクリラート · メタクリル酸ドデシル (stabilised with MEHQ) · ラウリルメタクリラート · n-ドデシルメタクリレート
識別子と物理属性
| CAS No. | 142-90-5 |
|---|---|
| 分子式 | C16H30O2 |
| 平均分子量 | 254.41 g/mol |
| 単同位体質量 | 254.2245802 g/mol |
| SMILES | C=C(C)C(=O)OCCCCCCCCCCCC |
| InChIKey | GMSCBRSQMRDRCD-UHFFFAOYSA-N |
| PubChem CID | 8906 |
| ChEMBL | CHEMBL1903701 |
| EC No. | 205-570-6 |
| DTXSID | DTXSID4027103 |
| 現地名 | メタクリル酸ドデシル |
化学・物理的性質
| XLogP | 7.2 |
|---|---|
| 極性表面積 | 26.3 |
| 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 |
| LogP（分配係数） | log Kow = 6.45 |
| 密度 | 0.868 at 77 °F (USCG, 1999) - Less dense than waterwill float0.87 at 77 °F (approx) (USCG, 1999) - Less dense than water0.868 @ 20 °CThe commercial material is a mixture containing both lower and higher fatty derivativesboiling range: 272-344 °Cbulk density: 0.868 g/ml0.868 @ 20°C0.868 g/mL at 25 °C (lit.) |
| 溶解度 | Insol in waterChloroform (Slightly), Methanol (Slightly)不溶性 |
| 引火点 | greater than 230 °F (USCG, 1999)132 °C (Cleveland open cup)126 °C (closed cup)>230 °F |
| 沸点 | 142 °C @ 4 mm Hg142 °C/4 mmHg (lit.) |
| Decomposition | When heated to decomp it emits acrid smoke and fumes. |
| 融点 | -8 °F (USCG, 1999)-20 °CMolecular weight: 262melting point: -22 °C/Made from a mixture of higher alcohols, predominately C-12/-7 °C (lit.) |
| 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/ |
| 蒸気圧 | 0.00118 [mmHg]0.0012 mm Hg @ 25 °C /Estimated/0.0012 [mm Hg] @20 °C0.06Pa at 20℃ |
| 屈折率 | Index of refraction: 1.444 @ 25 °C/Dn20/D 1.445(lit.) |
| ヘンリー定数 | Henry's Law constant: 3.3X10-3 atm cu m/mol @ 25 °C /Estimated/ |
| 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)[CAMEO] Clear colorless liquid[MSDSonline] |
| 貯蔵条件 | Inert atmosphere,2-8°C |
| 外観・状態 | 液体 |
| 色 | クリアライトイエロー |
| BRN | 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（分配係数） | 6.68 at 20℃ |
| CAS データベース | 142-90-5(CAS DataBase Reference) |
| NISTの化学物質情報 | 2-Propenoic acid, 2-methyl-, dodecyl ester(142-90-5) |
| EPAの化学物質情報 | Lauryl methacrylate (142-90-5) |
化学的特性
clear colorless to yellowish liquid
安全性と法規制
| GHS 分類 | WarningH335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory 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. |
|---|---|
| 規制情報 | Chemical: 2-Propenoic acid, 2-methyl-, dodecyl ester2-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/14902Dodecyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard |
| 火災危険 | 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) |
| 火災の可能性 | Combustible |
| 健康有害性 | 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) |
| 有害性の概要 | A mild skin and eye irritant in rabbits[HSDB] May polymerizeMay 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). |
| 反応性グループ | Acrylates and Acrylic AcidsPolymerizable Compounds |
| Reactivity Alerts | 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 3Serious eye damage/eye irritation - Category 2B |
| 消火 | Fire Extinguishing Agents: Foam, CO2 or dry chemical (USCG, 1999)Fire Extinguishing Agents: Foam, CO2, or dry chemical (USCG, 1999) |
| 応急処置 | 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 minhold 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)EYES OR SKIN: Flush with running water for at least 15 minuteshold 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) |
| 保管条件 | 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/ |
| 処分方法 | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand 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)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/ |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| 毒性の概要 | 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/kgLD50 Rabbit percutaneous >3.0 g/kgLD50 Rat ip 21.6 g/kgLD50 Mouse oral >87,250 mg/kgFor more Non-Human Toxicity Values (Complete) data for N-DODECYL METHACRYLATE (6 total), please visit the HSDB record page. |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | OZ4300000 |
| 輸送番号（UN） | UN 3082 9/PG 3 |
| 税関コード | 29161490 |
| 危険文句（R） | 36/37/38-50/53 |
| 化審法 | (2)-1039 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xi,N |
| 安全措置（S） | 26-28-60-61-28B |
| 危険等級 | 9Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 包装等級 | III |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 142-90-5(Hazardous Substances Data) |
用途
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.
製法・合成法
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.]