Ethyl L(-)-lactate
Ethyl L(-)-lactate
CAS: 687-47-8
Molecular Formula: C5H10O3
Ethyl L(-)-lactate - Names and Identifiers
| Name | Ethyl L(-)-lactate |
| Synonyms | L-Ethyl Lactate Ethyl L(-)-lactate (−)-Ethyl L-lactate Ethyl L(-)-lactate, pract., Propanoic acid, 2-hydroxy-, ethyl ester, (2S)- Propanoic acid, 2-hydroxy-, ethyl ester, (2S)- (9CI) |
| CAS | 687-47-8 |
| EINECS | 211-694-1 |
| InChI | InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3 |
Ethyl L(-)-lactate - Physico-chemical Properties
| Molecular Formula | C5H10O3 |
| Molar Mass | 118.131 |
| Density | 1.05g/cm3 |
| Melting Point | -26℃ |
| Boling Point | 154.5°C at 760 mmHg |
| Flash Point | 54.6°C |
| Water Solubility | SOLUBLE |
| Vapor Presure | 1.16mmHg at 25°C |
| Refractive Index | 1.42 |
| Physical and Chemical Properties | Characteristics of colorless transparent liquid, with a strong odor of wine. melting point -25 ℃ boiling point 154.2 ℃ relative density 1.0302 refractive index 1.4124 flash point 96 ℃ soluble in ethanol and ether. Miscible with water. |
| Use | Used as food flavoring agent, alcohol flavoring agent, pharmaceutical intermediates |
Ethyl L(-)-lactate - 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 | UN 1192 |
Ethyl L(-)-lactate - Upstream Downstream Industry
Ethyl L(-)-lactate - Security information
| dangerous goods mark | Xi,F |
| hazard category code | 10-37-41 |
| safety instructions | 24-26-39 |
| dangerous goods transport number | UN 1192 3/PG 3 |
| WGK Germany | 1 |
| RTECS number | OD5075000 |
| auto-ignition temperature | 752 °F |
| Hazard Note | Irritant/Flammable |
| TSCA | Yes |
| HazardClass | 3 |
| PackingGroup | III |
| customs code | 29181100 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
Last Update：2024-04-10 22:29:15
Ethyl L(-)-lactate - Nature
| melting point | −26 °C(lit.) |
| specific rotation | -10 ° (neat) |
| boiling point | 154 °C(lit.) |
| density | 1.034 g/mL at 20 °C(lit.) |
| vapor density | 4.1 (vs air) |
| Vapor pressure | 2mm Hg ( 20 °C) |
| refractive index | n20/D 1.4130(lit.) |
| FEMA | 2440 | ETHYL LACTATE |
| flash point | 54.6±6.4 °C |
| storage conditions | Store below +30°C. |
| acidity coefficient (pKa) | 13.21±0.20(Predicted) |
| morphology | Liquid |
| color | Clear colorless to pale yellow |
| PH value | 4 (50g/l, H2O, 20℃) |
| optical activity (optical activity) | [α]20/D 10.5±1°, neat |
| explosion limit value (explosive limit) | 1.5-16.4%(V) |
| water solubility | SOLUBLE |
| Merck | 14,3817 |
| BRN | 1720839 |
| NIST chemical information | Propanoic acid, 2-hydroxy-, ethyl ester, (S)-(687-47-8) |
Last Update：2024-04-09 21:11:58
Ethyl L(-)-lactate - Uses and synthesis methods
chemical properties
colorless transparent liquid with strong smell of wine. Soluble in ethanol and ether. Miscible with water.
use
1. Used as food flavoring agent, wine flavoring agent, pharmaceutical intermediate
2. ethyl lactate is a edible spice allowed in our country. it is often used to make fruit flavor, frankincense flavor and wine flavor. According to the normal production requirements, the dosage is generally 1000 mg/kg in alcoholic beverages. 580~3100 mg/kg in chewing gum; 7lmg/kg in baked food; 28 mg/kg in candy; 17 mg/kg in cold drinks.
3. this product is a solvent for nitrocellulose and acetic acid fiber, and is also a high-grade solvent for artificial pearls. Ethyl lactate has a bouquet-like aroma. Used for the preparation of wine flavors and edible flavors.
4. Used as a solvent for nitrocellulose and acetic acid fiber, also used in the perfume industry
production method
lactic acid and excess ethanol are heated and refluxed for several hours in the presence of sulfuric acid to produce this product.
Production method Metal halide catalytic method
metal halide was used instead of concentrated sulfuric acid to catalyze the synthesis of ethyl lactate with a yield of 65% ~ 71%.
Rare earth compound catalytic method
0.22~0.33mol of ethanol, 0.1lmol of lactic acid, 25mL of water-carrying agent and rare earth compound (molar ratio to acid is 1:100) were added to the flask, and the reflux reaction was 2.5~3h. The reaction liquid was distilled after evaporating the amount of ethanol, water-carrying agent and unreacted lactic acid, and then the product was collected under reduced pressure, with a yield of 74% ~ 79%.
Sulfuric acid catalysis
ethyl lactate is obtained by esterification of lactic acid and excess ethanol under sulfuric acid catalysis; It can also be heated and refluxed in carbon tetrachloride for 24 hours, and the excess ethanol is recovered by atmospheric distillation, and then the finished product is distilled under reduced pressure.
CH3CH(OH)COOH+C2H5OH[H2SO4]→CH3CH(OH)COOC2H5+H2O
Solid acid catalysis
NaY molecular sieve is washed, dried and burned at high temperature, then stirred and heated with a certain concentration of NH4C1 solution for ion exchange, NH4Y is filtered, washed and dried, and activated at high temperature at 550 ℃ to obtain solid acid HY.
then lactic acid, ethanol, benzene and HY were added to the reaction flask, HY/lactic acid = 25/100 (mass), lactic acid/ethanol (mole) = 1/3. The esterification rate was over 60% at 100~160 ℃ for 8~10h.
distillation esterification
225g of 80% lactic acid, 475mI. (380g)95% ethanol, 100mL benzene, 2mL concentrated sulfuric acid and a little zeolite were added to the flask (1000mL) of the water separation distillation unit. The reaction liquid is heated to boiling, the steam (ethanol, benzene and water) enters the condenser after passing through the distillation column, divides the water layer and reflows to the distillation column, and the top temperature of the column is stable at 64.9 ℃. When 240g of water layer (including 119g of ethanol, 99g of water and 22g of benzene) is separated out, it is basically separated out without water. When the top temperature of the column rises to 68 ℃, esterification ends. After the reaction solution is cooled, 6g of anhydrous sodium acetate is added to neutralize sulfuric acid, and distillation is carried out under reduced pressure. First, total reflux was carried out for 1h, then under the vacuum degree of 2.45kPa, the reflux ratio was controlled to be not less than 5, the top temperature of the column was 58 ℃, and 226g of colorless and clear ethyl lactate was distilled with 96% yield.
Last Update：2024-04-09 21:01:54
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Raw Materials for Ethyl L(-)-lactate
Downstream Products for Ethyl L(-)-lactate