Methyl 3-methyl-2-butenoate
methyl 3,3-dimethylacrylate
CAS: 924-50-5
Molecular Formula: C6H10O2
Methyl 3-methyl-2-butenoate - Names and Identifiers
Methyl 3-methyl-2-butenoate - Physico-chemical Properties
| Molecular Formula | C6H10O2 |
| Molar Mass | 114.14 |
| Density | 0.935g/mLat 20°C |
| Melting Point | -41°C |
| Boling Point | 70-75°C60mm Hg(lit.) |
| Flash Point | 99°F |
| Water Solubility | Soluble in chloroform. Insoluble in water, |
| Vapor Presure | 7.36mmHg at 25°C |
| Appearance | clear liquid |
| Color | Colorless to Almost colorless |
| Maximum wavelength(λmax) | ['216nm(CH3CN)(lit.)'] |
| BRN | 1741592 |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Sensitive | Light Sensitive |
| Refractive Index | n20/D 1.4364(lit.) |
| Physical and Chemical Properties | This product is colorless liquid, B. p.70 ~ 75 ℃/8 kpa,n20D 1.4364, relative density 0.873,f.p.99 ℉(37 ℃), insoluble in water, soluble in chloroform, carbon tetrachloride and other organic solvents. |
Methyl 3-methyl-2-butenoate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 10 - Flammable |
| Safety Description | S16 - Keep away from sources of ignition. S29 - Do not empty into drains. S33 - Take precautionary measures against static discharges. |
| UN IDs | UN 3272 3/PG 3 |
| WGK Germany | 1 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 29161900 |
| Hazard Note | Irritant |
| Hazard Class | 3 |
| Packing Group | III |
Methyl 3-methyl-2-butenoate - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Use | methyl methacrylate is an important intermediate in the preparation of chrysanthemum acid by Martel method. |
| production method | the preparation method is to use diacetone (1mol) and sodium hypochlorite solution (500mL) in the reaction bottle, the reaction is exothermic, and the temperature is raised to 50 °c, and sodium hypochlorite (150mL, total amount is 5mol) is added dropwise. The dropping acceleration is controlled, and the reaction temperature is maintained at 55~60 °c, raise the temperature to about 65 ℃, and then continue to stir under natural cooling for 3~4H, add a small amount of Na2SO3 to reduce excess sodium hypochlorite, and then stand to separate, separate chloroform, acidified with dilute H2SO4 at 20 °c, extracted with chloroform, washed with water, dried, distilled solvent chloroform, and the residue cooled to give a yellow solid, isopentenoic acid (CAS[541-47-9]), m. P. 60-65 °c (literature value m. P. 68.5-69.5 °c), B. P. 194-195 °c. After mixing 1mol of the above-prepared isopentenoic acid with 4.4mol of methanol, adding a little concentrated sulfuric acid as a catalyst, stirring and reacting at 60-70 ° C. For 5H, cooling, diluting with water to separate the organic layer, and extracting the aqueous layer with chloroform, the mixture was combined with the organic layer, washed with dilute Na2CO3 solution, washed with water and dried. The chloroform was distilled off, and the 130-140 ° C. Fraction was collected as methyl methacrylate. The reaction equation is as shown in the figure: In addition, isobutylene and carbon tetrachloride are used in the polycondensation reaction under pressure in the presence of copper catalyst, and then sulfuric acid is hydrolyzed to obtain isopentenic acid, and the yield of the two steps can reach more than 84%, further esterification with an alcohol yields the isopentenyl ester. The reaction equation is as shown in the figure: trialkyl phosphite can also be used to react with ethyl chloroacetate to generate ethyl acetate dialkyl phosphite, and then in polar solvent, in strong base (such as sodium hydride, sodium amino acid, sodium alkoxide) reaction with acetone in the presence of China-E (Wadsovorth-Emmons), that is, to obtain isopentenoic acid ester (the first step yield is 90%, The yield for the second step was 84.5%). |
Last Update：2024-04-09 21:32:09
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