Methyl methacrylate 80-62-6
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Methyl methacrylate is an organic compound with the chemical formula CH 2 =C(CH 3 )COOCH 3. This colorless liquid, methyl methacrylate (MAA) is a mass-produced monomer used in the production of polymethyl methacrylate (PMMA).
| describe | Methyl methacrylate is an organic compound with the chemical formula CH 2 =C(CH 3 )COOCH 3 . This colorless liquid, methyl methacrylate (MAA) is a mass-produced monomer used in the production of polymethyl methacrylate (PMMA). |
| chemical properties | Methyl methacrylate is a colorless liquid. It has a spicy, fruity smell. Odor threshold is 0.05 0.083 ppm |
| chemical properties | Methyl methacrylate is the methyl ester of methacrylic acid. It is a colorless, volatile liquid with a spicy, fruity odour. It has a relatively high vapor pressure (4 kPa at 20°C), moderate water solubility (15.8 g/L), and a low log octanol/water partition coefficient (Kow = 1.38). Methyl methacrylate is typically 99.9% pure and contains small amounts of inhibitors to retard polymerization. |
| chemical properties | Methyl 2-methyl-2-acrylate has a pungent, pungent odor. Another report says the compound has a strong fruity taste |
| physical properties | Transparent, colorless liquid with a penetrating fruity aroma. An experimentally determined odor threshold concentration of 210 ppb v was reported by Leonardos et al. (1969). The experimentally determined threshold concentrations for detection and identification of odorants are 200 μg/m 3 (49 ppb v ) and 1.4 mg/m 3 (340 ppb v ) respectively (Hellman and Small, 1974). |
| use | The main application that consumes approximately 80% of MMA is the manufacture of polymethylmethacrylate acrylic plastic (PMMA). Methyl methacrylate is also used in the production of methyl methacrylate-butadiene-styrene copolymer (MBS), which is used as a modifier for PVC. Another application is as cement used in total hip replacements and total knee replacements. Orthopedic surgeons use it as a "grout" to secure the bone insert into the bone, and it greatly reduces post-operative pain from the insert, but it has a limited lifespan. Typically, methyl methacrylate has a useful life of 20 years as a bone cement before revision surgery is required. Cemented implants are generally reserved for older adults who require immediate, short-term replacement. In younger populations, cementless implants are used because of their considerable longevity. Also used for fracture repair in small exotic animal species using internal fixation. |
| use | Methyl methacrylate is used in acrylic bone cements used in orthopedic surgery; in the production of acrylic polymers, polymethyl methacrylate and copolymers for acrylic surface coatings; in the manufacture of emulsion polymers; Modification of saturated polyester resins; for the production of advanced methacrylates, acrylic fibers, acrylic films, inks, impregnants for radiation polymerization of wood, and solvent-based adhesives and adhesives; as an impact modifier for PVC; In pharmaceutical spray adhesives; in non-irritating solvents for bandages; in dental technology as ceramic fillers or cements; coating corneal contact lenses; in intraocular lenses, artificial nails and hearing aids; as polymethacrylates Resin monomer; in concrete impregnation, etc. |
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| production method | Methyl methacrylate (MMA) is the most important methacrylate. It can be homopolymerized and copolymerized to produce acrylic resin with good strength, transparency and excellent weather resistance. The first commercial process for manufacturing MMA (1930s), the acetone cyanohydrin route, remains the dominant process today. In the acetone cyanohydrin route, acetone cyanohydrin reacts with sulfuric acid at low temperature to form the sulfuric acid monoester of 2-hydroxy-2-methyl-propionamide, which is exposed to higher temperatures (100° - 140°C) After the formation of sulfuric acid methacrylamide. The liquid phase was maintained by using an excess of 0.2-0.7 molar excess of 100% sulfuric acid. The first step of the reaction is strongly exothermic, while the rearrangement of the sulfate ester is endothermic. During the synthesis of methacrylamide, part of acetone cyanohydrin decomposes into carbon monoxide in the first part of the reaction. In addition, due to the strength and high temperature of the acid in the second step, other by-products are formed and react. About 92 - 94% of the acetone cyanohydrin is converted to useful products and 6 - 8% is consumed in the formation of organic by-products (acetone, acetone sulfonate, oligomers, polymers, etc.). Esterification of methacrylamide sulfate with a mixture of water and methanol to form MMA and an aqueous solution of ammonium bisulfate, sulfuric acid and organic by-products. Ammonium bisulfate is an unavoidable by-product of this reaction. |
| production method | The compound can be produced by a variety of methods, one of the main ones being the acetone cyanide (ACH) route, which uses acetone and hydrogen cyanide as raw materials. The intermediate cyanohydrin is converted into the sulfate ester of methacrylamide with sulfuric acid, and its methanolysis is decomposed to obtain ammonium bisulfate and MMA. Although the ACH route is widely used, it also produces large amounts of ammonium sulfate. Some producers start with isobutene or the equivalent tert-butanol, first sequentially oxidized to methacrolein, then to methacrylic acid, and then esterified with methanol. Propylene can be carbonylated to isobutyric acid in the presence of acid, followed by dehydrogenation. The combined technology can provide production of more than 3 billion kilograms per year. |
| definition | ChEBI: Methyl methacrylate is an acrylic acid ester containing methacrylic acid as the carboxylic acid component and methanol as the alcohol component. It acts as an allergen and polymerizes monomers. It is acrylate and methyl ester. It is functionally related to methacrylic acid. |
| Prepare | It is derived from the esterification of methacrylamide sulfate and methanol. |
| aroma threshold | Detection concentration is 0.024 to 0.058 ppm (water); identification concentration is 0.7 to 1.4 mg/m3 (air); detection concentration is 0.2 to 0.62 mg/m3. |
| synthetic references | Journal of the American Chemical Society, 70, p. 1153, 1948 DOI: 10.1021/ja01183a082 Journal of Organic Chemistry, 33, p. 2525, 1968 DOI: 10.1021/jo01270a082 |
| general instructions | Colorless transparent liquid. Slightly soluble in water, floating on water. Vapor is heavier than air. Vapor is irritating to eyes and respiratory system. Containers must be strictly insulated or refrigerated for transport. Inhibitors such as hydroquinone, hydroquinone methyl ester, and dimethyl tert-butylphenol are added to prevent chemicals from initiating polymerization. This chemical may undergo exothermic polymerization if heated or contaminated with strong acids or bases. If polymerization occurs within a container, the container may rupture violently. Used to make plastics. |
| air and water reaction | Highly flammable. Very slightly soluble in water. |
| reactive profile | Methyl methacrylate may polymerize if contaminated or exposed to heat. If polymerization occurs in a container, the container will burst violently. It is easily oxidized in air to form unstable peroxide, which may self-destruct [Bretherick 1979. p.151-154, 164]. Peroxides may also initiate exothermic polymerization of the bulk material [Bretherick 1979. p. 17]. 160]. Weigh the benzoyl peroxide into a beaker that has been previously rinsed with methyl methacrylate. The peroxide catalyzes the polymerization of methyl methacrylate, and the accumulation of heat ignites the remaining peroxide [MCA Case History 996.1964]. |
| adventure | Flammable and fire hazard, explosion limit in air is 2.1-12.5%. Irritation to eyes and upper respiratory tract, effects on weight, and pulmonary edema. Suspected carcinogen. |
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| fire hazard | Behavior in Fire: Vapors are heavier than air and may travel considerable distances to the source of fire and backfire. Containers may explode due to polymerization in fire or when heated. |
| Flammability and explosiveness | Flammable |
| Industrial applications | Initiators for the polymerization of methyl methacrylate include AIBN, dilauroyl peroxide (LPO) and 2,2'-azobis[2-(2-imidazolin-2-yl)propane]. |
| Security overview | Inhalation and intraperitoneal routes are moderately toxic. Mildly toxic if swallowed. Systemic effects of inhalation: sleep effects, agitation, anorexia and decrease in blood pressure. Experimental teratogenic and reproductive effects. Report mutation data. Irritating to skin and eyes. Suspected carcinogen with experimental tumorigenic data. A common air pollutant. Very dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. Explodes in vapor form when exposed to heat or flame. Monomers can undergo spontaneous explosive polymerization. Reacts in air to form thermally sensitive explosive products (evaporative explosion at 6OOC). May burn on contact with benzoyl peroxide. With polymerization initiator azoisobutyronitrile, dibenzoyl peroxide, di-tert-butyl peroxide, propionaldehyde. When extinguishing fire, use foam, carbon dioxide, dry chemical. When heated and decomposed, acrid and irritating fumes are released. |
| potential contact | Virtually all methyl methacrylate monomer produced is used in the production of polymers such as surface coating resins; plastics (plexiglass and plexiglass); ion exchange resins; and plastic dentures. |
| Carcinogenicity | In several lifetime animal studies, there is no evidence that methyl methacrylate is carcinogenic. |
| environmental fate | Chemistry/Physics. Easy to polymerize (Windholz et al., 1983). Methyl methacrylate undergoes nucleophilic attack (hydrolysis) by OH ions in water, resulting in the formation of methacrylic acid and methanol (Kollig, 1993). The hydrolysis rate at 25 °C is 171/M?h (Sharma and Sharma, 1970). No measurable hydrolysis was observed at 85.0 °C (pH 7) and 25 °C (pH 7.07). The hydrolysis half-lives observed at 66.0 °C (pH 9.86) and 25.0 °C (pH 11.3) were 9 and 134 min, respectively (Ellington et al., 1987). |
| storage | Methyl methacrylate is an active chemical that must be stored and handled with care. It is stable under recommended storage conditions. Heat can cause polymerization. Inhibitors are added to methyl methacrylate monomer to prevent polymerization. For the inhibitor to be effective, the oxygen concentration in the vapor space must be at least 5%. Store material in containers made of stainless steel, carbon steel, glass or aluminum. Avoid exposure to acids, bases, oxidizing agents, reducing agents, ultraviolet light (ultraviolet rays found in sunlight), free radical initiators and organic peroxides. |
| Shipping | UN1247 Methyl methacrylate monomer, stable, hazard class: 3; Label: 3 - Flammable liquid. |
| Purification method | The ester was washed twice with 5% aqueous NaOH (to remove inhibitors such as hydroquinone) and then twice with water. Dry with CaCl2, Na2CO3, Na2SO4 or MgSO4, then with CaH2 under nitrogen and reduced pressure. The distillate is stored at low temperatures and redistilled before use. Before distillation, inhibitors such as hydroquinone (0.004%), beta-naphthylamine (0.2%) or di-naphthol are sometimes added. It can also be purified by boiling with an aqueous H3PO4 solution and finally with a saturated NaCl solution. Dry with anhydrous CaSO4 for 24 hours, distill at room temperature with 0.1mm Hg, and store at -30o [Albeck et al. J Chem Soc, Faraday Trans 1 1 1488 1978]. [Berstein 2 II 398, 2 III 1279, 2 IV 1519. ] |
| Toxicity evaluation | Mitochondria are considered the main intracellular target of MMA. Oxygen consumption increases if isolated rat liver mitochondria are incubated with MMA. This is a consequence of the uncoupling of the mitochondrial respiratory chain, as seen from the expected effects on state 4 and state 3 respiration. State 4 Breathing is stimulated. As reported for organic solvents, MMA attacks respiratory chain complex I close to the rotenone binding site. This means that substrates that are oxidized with nicotinamide adenine dinucleotide inhibit electron flow and thus ATP synthesis. Unlike classical uncouplers, MMA stimulates Mg2+-dependent ATPase bound to the inner mitochondrial membrane. The structural changes in the inner membrane of non-ionic detergents were observed by electron microscopy. |
| Incompatibility | Vapors may form explosive mixtures with air. Reacts in air to form heat-sensitive explosive products at 60°C. Incompatible with nitrates, oxidants, peroxides, strong acids; strong bases; oxidants, reducing agents; amines, moisture. Exposure to benzoyl peroxide may cause ignition, fire, and explosion. Polymerization catalysts such as azoisobutyronitrile, dibenzoyl peroxide, may polymerize if exposed to heat; strong oxidizing agents; or ultraviolet light. May contain inhibitors such as hydroquinone. |
| waste disposal | Consult environmental regulatory agencies for guidance on acceptable disposal practices. Producers of waste containing this contaminant (≥100 kg/mo) must comply with EPA regulations for storage, transportation, handling, and waste disposal. Burning may be permitted. |
| Methyl methacrylate upstream and downstream product information |
| raw material | Methanol --> Sulfuric acid -->Sodium cyanide--> Carbon monoxide -- > Isobutylene -->Isobutyraldehyde-->Hydrogen cyanide -->Acetone cyanide --> Methyl isobutyrate --> Ammonium methacrylate bisulfate |
| Preparation products | 聚丙烯酸--> 2,2-二氯-1-甲基环丙胺-->苯乙烯-丙烯酸乳胶-->氯丁橡胶粘合剂--> 4-氯-7-甲基噻吩[3,2-D]嘧啶--> 7-甲基噻吩并[3,2-d]嘧啶-4(3H)-一--> 1-BENZYL-3-METHYL-4-PIPERIDONE -->导电涂料-丙烯酸共聚物与碘化亚铜复合体系--> CC -2SH前牙复合粘合材料-->微分散丙烯酸酯树脂充填乳液--> GD可见光固化复合树脂--> 3-氯-4-甲基-2-噻吩甲酸-->3-氯-4-甲基噻吩-2-羧酸甲酯-->光盘基材改性 PMMA 共聚物-->速克利-->丝网印刷用粘合剂--> 甲基丙烯酸 2,3-二羟丙酯-->聚甲基丙烯酸甲酯-->胸腺嘧啶-->羧基型阳离子交换树脂--> 3-氨基-4-甲基噻吩-2-甲酸甲酯-->压敏胶-->皮革光亮剂-->热塑性丙烯酸树脂-->比卡鲁胺- -> 3-甲基丙烯酰氧基丙基三甲氧基硅烷-->增稠剂 PAE-->二氢胸腺嘧啶 |
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