ethyl (2R)-2-hydroxypropanoate
ethyl lactate
CAS: 97-64-3
Molecular Formula: C5H10O3
ethyl (2R)-2-hydroxypropanoate - Names and Identifiers
| Name | ethyl lactate |
| Synonyms | Purasolv ELS ethyl lactate Dl-Ethyl Lactate Lactic acid ethyl Ethyl rac-lactate Lactic acid ethyl ester ethyl 2-hydroxypropanoate ETHYL LACTATE NATURAL FCC Ethyl α-hydroxypropanoate ETHYL LACTATE SOLVENT GRADE 2-Hydroxypropionic acid ethyl ethyl (2R)-2-hydroxypropanoate Propanoic acid, 2-hydroxy-, ethyl ester |
| CAS | 97-64-3 |
| EINECS | 202-598-0 |
| InChI | InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3/t4-/m1/s1 |
| InChIKey | LZCLXQDLBQLTDK-UHFFFAOYSA-N |
ethyl (2R)-2-hydroxypropanoate - Physico-chemical Properties
| Molecular Formula | C5H10O3 |
| Molar Mass | 118.13 |
| Density | 1.031 g/mL at 25 °C (lit.) |
| Melting Point | -26°C |
| Boling Point | 154 °C (lit.) |
| Specific Rotation(α) | D14 -10° |
| Flash Point | 54.6±6.4 °C |
| JECFA Number | 931 |
| Water Solubility | 100g/L at 20℃ |
| Solubility | Miscible with water (with partial decomposition),ethanol (95%), ether, chloroform, ketones, esters, and hydrocarbons. |
| Vapor Presure | 81hPa at 20℃ |
| Appearance | clear liquid |
| Color | Colorless |
| Odor | Mild characteristic. |
| Merck | 14,3817 |
| pKa | 13.21±0.20(Predicted) |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.4124 |
| Physical and Chemical Properties | Colorless transparent liquid, with a strong odor of wine. |
| Use | Used as a solvent for nitrocellulose and cellulose acetate, also used in the fragrance industry |
ethyl (2R)-2-hydroxypropanoate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R10 - Flammable R37 - Irritating to the respiratory system R41 - Risk of serious damage to eyes |
| Safety Description | S24 - Avoid contact with skin. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. |
| UN IDs | 1192 |
| WGK Germany | 1 |
| RTECS | OD5075000 |
| HS Code | 29181100 |
| Hazard Class | 3.2 |
| Packing Group | III |
ethyl (2R)-2-hydroxypropanoate - Nature
Open Data Verified Data
A colorless to yellowish transparent liquid with an aroma of rum, fruit, and cream. Soluble in ethanol, acetone, ether, esters and other organic solvents, and water miscible with partial hydrolysis.
Last Update：2024-01-02 23:10:35
ethyl (2R)-2-hydroxypropanoate - Preparation Method
Open Data Verified Data
obtained by esterification of lactic acid with excess ethanol in the presence of a catalyst and purification.
Last Update：2022-01-01 10:07:14
ethyl (2R)-2-hydroxypropanoate - Use
Open Data Verified Data
It is mainly used for the preparation of apple, pineapple, caramel, frankincense and other food essences, and also used in rum, liquor and other wine flavors. Ethyl lactate is the food flavor allowed in our country. Generally, lOOOmg/kg in alcoholic beverages; 580 ~ 3100mg/kg in chewing gum; 71mg/kg in baked food; 28mg/kg in candy; 17mg/kg in cold drinks.
Last Update：2022-01-01 10:07:15
ethyl (2R)-2-hydroxypropanoate - Reference Information
| FEMA | 2440 | ETHYL LACTATE |
| LogP | 0.7 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| properties | ethyl lactate is a colorless to yellowish transparent liquid, soluble in esters and other organic solvents, partially hydrolyzed when miscible with water. |
| Use | GB 2760-96 specifies the permitted use of flavorants. Carrier solvent. As a spice mainly used in the preparation of rum, milk, cream, grape, fruit wine, coconut flavor. ethyl lactate is a kind of edible flavor allowed by regulations in China, which is commonly used in the preparation of fruit flavor, lactic acid type and wine flavor. Dosage according to the normal production needs, generally in the wine beverage 1000mg/kg, chewing gum 580-3100 mg/kg, baked food 71 mg/kg, Candy 28 mg/kg, 17 mg/kg in cold drinks. GB 2760-96 provides for the permitted use of flavorants. Carrier solvent. As a spice mainly used in the preparation of rum, milk, cream, grape, fruit wine, coconut flavor. as a solvent for nitrocellulose and cellulose acetate, it is also used in perfume industry nitrocellulose and cellulose acetate solvent. Organic Synthesis. Food additives. |
| content analysis | approximately 0.7g of a sample was precisely weighed and then determined according to Method 1 of the ester determination method (OT-18). The equivalence factor (e) in the calculation is taken as 59.07. Or according to GT-10-4 using non-polar column method. |
| toxicity | ADI is not specified (FAO/WHO,1994). GRAS(FEMA). LD50 2500mg/kg (mouse, oral). |
| usage limit | FEMA(mg/kg): Soft drink 5.4; Cold drink 17; Candy 28; Baked goods 71; pudding 8.3; Gum 580~3100; Wine 1000; Syrup 35. Moderate limits (FDA § 172.515,2000). |
| production method | The right-handed body and the left-handed body respectively take the right-handed lactic acid and the left-handed lactic acid as raw materials, in the presence of concentrated sulfuric acid, it is obtained by co-boiling esterification with ethanol in benzene and distillation. Racemates are produced by boiling racemic lactic acid and ethanol in carbon tetrachloride for 24h. Acetaldehyde cyanohydrin is formed by the combination of acetaldehyde and cyanohydric acid, and then esterified with ethanol in the presence of inorganic acid. (1) metal halide catalytic method. Ethyl lactate was synthesized catalytically by using metal halide instead of concentrated sulfuric acid. The yield was 65%-71%. (2) rare earth compound catalytic method. Add 0.22-0.33mol of ethanol, 0.11mol of lactic acid, 25ml of water-carrying agent and rare earth compound (molar ratio of 1:100 with acid) to the flask, reflux and react for 2.5-3H, the reaction solution was distilled under reduced pressure after the amount of ethanol, the water-carrying agent and the unreacted lactic acid were distilled, and the product was collected, and the yield was 74%-79%. (3) sulfuric acid catalytic method. Under the catalysis of sulfuric acid, lactic acid is esterified with excess ethanol to obtain ethyl lactate; It can also be heated in carbon tetrachloride to flow dehydration for 24h, and the excess ethanol is recovered by atmospheric distillation, and then the finished product is distilled under reduced pressure. (4) solid acid catalysis. NaY molecular sieve is washed with water, dried and burned at high temperature, then stirred and impregnated with a certain concentration of NH4Cl solution for ion exchange, and NH4Y is filtered, washed and dried, and activated at 550 ℃ at high temperature to obtain solid acid HY. Lactic acid, ethanol, benzene, HY were then added to the reaction flask, HY/lactic acid (mass ratio) = 100/1 and lactic acid/ethanol (molar ratio) = 1/3. The esterification rate was more than 60% at 100-160 ℃ for 8-10H. (5) distillation esterification method. 225g of 80% lactic acid, 95% mL (1000g) of ethanol, mL of benzene, 2 mL of concentrated sulfuric acid, and a little zeolite were charged to a flask (mL) of a water separating distillation apparatus. The reaction liquid was added to the boiling point, and the steam (ethanol, benzene and water) was passed through the distillation column and then entered the condenser. The water layer was separated and refluxed to the distillation column, and the temperature at the top of the column was stabilized at 64.9 °c. When 240g of the aqueous layer (containing 119g of ethanol, 99g of water and 22g of benzene) was separated, the separation was almost anhydrous, and the esterification was completed when the temperature of the column top rose to 68 °c. After cooling the reaction solution, 6g of anhydrous sodium acetate was added to neutralize sulfuric acid, and distillation was performed under reduced pressure. First total reflux for 1H, and then under the vacuum of 2.45Kpa, the reflux ratio is controlled to be not less than 5, the column top temperature is 58 ° C., 226g of colorless clear ethyl lactate is distilled, and the yield is 96%. |
| category | flammable liquid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 5000 mg/kg; Oral-mouse LD50:2500 mg/kg |
| explosive hazard characteristics | explosive when mixed with air |
| flammability hazard characteristics | flammable in case of open flame, high temperature and oxidant; combustion-induced smoke |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from the oxidant |
| extinguishing agent | dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:11:58
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