carbonochloridicacid,1-methylpropylester
sec-butyl chloroformate
CAS: 17462-58-7
Molecular Formula: C5H9ClO2
carbonochloridicacid,1-methylpropylester - Names and Identifiers
| Name | sec-butyl chloroformate |
| Synonyms | SBCF 241-475-6 s-ButylChloroformate sec-butyl chloroformate SEC-BUTYL CHLOROFORMATE sec-Butyl chlorocarbonate sec-Butyl carbonochloridate Butan-2-yl carbonochloridate butan-2-yl carbonochloridate Chloroformic acid sec-butyl este Chloridocarbonic acid sec-butyl ester carbonochloridicacid,1-methylpropylester |
| CAS | 17462-58-7 |
| EINECS | 241-475-6 |
| InChI | InChI=1/C5H9ClO2/c1-3-4(2)8-5(6)7/h4H,3H2,1-2H3 |
carbonochloridicacid,1-methylpropylester - Physico-chemical Properties
| Molecular Formula | C5H9ClO2 |
| Molar Mass | 136.58 |
| Density | 1.081±0.06 g/cm3(Predicted) |
| Boling Point | 126 °C |
| Flash Point | 35.842°C |
| Vapor Presure | 8.236mmHg at 25°C |
| Refractive Index | 1.417 |
carbonochloridicacid,1-methylpropylester - Risk and Safety
| UN IDs | UN 2742 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
carbonochloridicacid,1-methylpropylester - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| synthesis | SEC-butyl chloroformate SEC-butyl chloroformate was produced from the reaction of triphosgene with SEC-butyl alcohol in a yield of about 74%. |
| Use | SEC-butyl chloroformate is an organic chemical raw material used in the synthesis of compounds with certain uses. 1. S-butyl chloroformate for the synthesis of the insecticide hydroxyperoxides: comprising the following steps: 1) preparation of 2-ethanolpiperidine: 2-ethanolpyridine is dissolved in the amount of polar solvent is 1-5 times its weight, in the amount of 2-ethanolpyridine is 0.1 ~ 10% by weight under the action of high efficiency hydrogenation catalyst, under the conditions of 1~10MPa hydrogen pressure and 50~120 ℃ temperature, the reaction time is 6~12 hours, the content of 2-ethanolpyridine is less than 0.5% of the total amount, the reaction solution was filtered to remove the catalyst, and the solvent was recovered under reduced pressure. The residue was 2-ethanolpiperidine: the 2-ethanolpiperidine is dissolved in a nonpolar solvent with a dosage of 1-5 times its weight, and the reaction temperature is controlled at 40-80 ℃, at the same time, SEC-butyl chloroformate and alkali solution with concentration of 1 ~ 20% were added dropwise, and the molar ratio was Alkali: SEC-butyl chloroformate: 2-ethanolpiperidine = 1~1.5: 1~1.3: 1, control the dropwise addition time within 1~6 hours, continue to stir until the end of the reaction, separate the aqueous layer, organic phase concentration of 1 ~ 10%, the amount of 2-ethanolpiperidine 1~3 times the weight of dilute acid washing two times, and then washed twice, The solvent was recovered under reduced pressure, and the residue was the crude product of the hydroxypiperonyl ester; 3) purification of the hydroxypiperonyl ester: the amount of antioxidant added in the crude product is 1 ~ 3% by weight, under the high vacuum of less than 5mmHg, 140~150 ℃ high temperature distillation to obtain more than 98% of the content of the finished products; 2. SEC-butyl chloroformate is an insect repellent. The preparation method includes the following steps: 1) preparation of 2-hydroxyethyl pyridine, the paraformaldehyde and the catalyst are added into the reaction flask, heated and stirred for reaction, distilled under reduced pressure, and the fraction of 130~150 ℃/10~20mmHg is collected to obtain the product 2-hydroxyethyl pyridine; the mass ratio of-picoline to paraformaldehyde is 1 ∶(0.2~0.4), and the mass percentage of added catalyst is 2%~ 5% of 2-picoline; the reaction temperature is 60~100 deg C; Stirring reaction time is 15~20H; The catalyst is sodium carbonate or potassium carbonate. 2) preparation of 2-hydroxyethyl piperidine: 2-hydroxyethyl pyridine was dissolved in solvent, Catalyst was added, and hydrogen was added to heat the reaction, gas chromatography analysis showed that the reaction was stopped when the content of 2-hydroxyethyl pyridine was less than 1% of the total, the reaction solution was filtered to remove the catalyst, and the solvent was recovered by distillation, and the residue was 2-hydroxyethyl piperidine; the mass ratio of 2-hydroxyethyl pyridine to solvent is 1: (2~2) ~ 5); The amount of the catalyst added is 1% to 5% of 2-hydroxyethyl pyridine by mass; The pressure of the hydrogen gas is 2 to 4MPa; the reaction temperature was 60-80 °c and the reaction time was 4-8H. The solvent is one of toluene, ethyl acetate, tetrahydrofuran or ethanol; The catalyst is Raney nickel (SC-4100) or 10% Palladium carbon. 3) preparation of ecaredine: put 2-hydroxyethylpiperidine in the reaction flask, add 20% concentration of alkali solution, stir the mixture, add SEC-butyl chloroformate Dropwise to the mixture, continue stirring for 2H until the reaction is finished, remove the aqueous layer, wash the organic phase with 10% acid solution three times, and then wash with water twice, dry with anhydrous sodium sulfate, and remove the drying agent by filtration, to obtain the product ecaredin finished product. Wherein the molar ratio of 2-hydroxyethylpiperidine to base to SEC-butyl chloroformate is 1 :( 1.5~2.0) :( 0.95~1.0); The time for dropwise addition of SEC-butyl chloroformate was 60-100min, and the temperature for continued stirring reaction was 30-50 °c. The base is one of sodium carbonate, sodium hydroxide or sodium bicarbonate. The acid solution is one of hydrochloric acid solution, sulfuric acid solution or acetic acid solution, and the dosage is 3 times of the mass of 2-hydroxyethyl piperidine. |
| category | toxic substances |
| flammability hazard characteristics | open flame flammable; Toxic chloride smoke emitted by heat or water vapor |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; Moisture-proof; Separate storage and transportation from food and oxidant |
| fire extinguishing agent | foam, dry powder, carbon dioxide |
Last Update：2024-04-09 02:00:04
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