Ethyl acetoacetate
Ethyl acetoacetate
CAS: 141-97-9
Molecular Formula: C6H10O3
Ethyl acetoacetate - Names and Identifiers
| Name | Ethyl acetoacetate |
| Synonyms | EAA Acetoacetic ester Ethyl acetoacetate Ethyl acetylacetate Ethyl 3-oxobutanoate Acetoacetic acid ethyl 2-ethyl-3-oxobutanoate Ethyl beta-ketobutyrate Ethyl acetoacetate, extra pure Ethyl acetoacetate, synthesis grade Ethyl acetoacetate,Acetoacetic ester |
| CAS | 141-97-9 |
| EINECS | 205-516-1 |
| InChI | InChI=1/C6H10O3/c1-3-5(4(2)7)6(8)9/h5H,3H2,1-2H3,(H,8,9)/p-1 |
| InChIKey | XYIBRDXRRQCHLP-UHFFFAOYSA-N |
Ethyl acetoacetate - Physico-chemical Properties
| Molecular Formula | C6H10O3 |
| Molar Mass | 130.14 |
| Density | 1.029g/mLat 20°C(lit.) |
| Melting Point | −43°C(lit.) |
| Boling Point | 181°C(lit.) |
| Flash Point | 185°F |
| JECFA Number | 595 |
| Water Solubility | 116 g/L (20 ºC) |
| Solubility | 116 g/L (20°C) |
| Vapor Presure | 1 mm Hg ( 28.5 °C) |
| Vapor Density | 4.48 (vs air) |
| Appearance | Transparent liquid |
| Specific Gravity | 1.027～1.035 (20/4℃) |
| Color | APHA: ≤15 |
| Odor | Agreeable, fruity. |
| Merck | 14,3758 |
| BRN | 385838 |
| pKa | 11(at 25℃) |
| PH | 4.0 (110g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible. |
| Sensitive | Easily absorbing moisture |
| Explosive Limit | 1.0-54%(V) |
| Refractive Index | n20/D 1.419 |
| MDL | MFCD00009199 |
| Physical and Chemical Properties | Colorless liquid with pleasant fruit aroma. melting point <-45 ℃ boiling point 181 ℃ relative density 1.0282 refractive index 1.4194 flash point 84.4 ℃ solubility miscibility with common organic solvents, soluble in water. |
| Use | For organic synthesis, fragrances, dyes and pharmaceutical industries |
Ethyl acetoacetate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36 - Irritating to the eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN 1993 |
| WGK Germany | 1 |
| RTECS | AK5250000 |
| TSCA | Yes |
| HS Code | 29183000 |
| Hazard Class | 3.2 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 3.98 g/kg (Smyth) |
Ethyl acetoacetate - Upstream Downstream Industry
| Raw Materials | diketene Ethyl Alcohol |
| Downstream Products | Ethyl 2-methylacetoacetate 2-Acetylbutyrolactone N-Phenylglycine potassium salt Chrysin Pirimiphos-ethyl Pirimiphos-methyl Nitrendipine |
Ethyl acetoacetate - Nature
Open Data Verified Data
colorless liquid with pleasant fruit aroma. The relative density was 1. 0282. Melting point <-45 °c. Boiling point 181 °c. Flash point (closed cup) 84.4 °c. Refractive index 4194. Vapor pressure (200C) 106. Miscible with general organic solvents, soluble in water.
Last Update：2024-01-02 23:10:35
Ethyl acetoacetate - Preparation Method
Open Data Verified Data
- diketene and ethanol esterification method diketene and anhydrous ethanol were esterified under the catalysis of concentrated sulfuric acid to obtain crude ethyl acetoacetate. Then, the product was obtained by distillation under reduced pressure.
- The ethyl acetate self-condensation method is obtained by self-condensation of two molecules of ethyl acetate in the presence of metallic sodium.
Last Update：2022-01-01 10:33:32
Ethyl acetoacetate - Introduction
There is a fruit aroma of water. It is purple when encountering ferric chloride. Soluble in general organic solvents such as ether, benzene, ethanol, ethyl acetate, chloroform and acetone, and soluble in about 35 parts of water. Low toxicity, median lethal dose (rat, oral) 3.98G/kG. It's irritating. Water soluble 116g/L (20 ℃).
Last Update：2022-10-16 17:13:54
Ethyl acetoacetate - Use
Open Data Verified Data
It can be used to synthesize heterocyclic compounds such as pyridine, pyrrole, pyrazolone, pyrimidine, purine and cyclic lactone. It also has important applications in pesticides, spices, photochemicals, polymerization catalysts, etc. It can also be used as a food flavoring agent. Also used as a solvent, also a reagent for the detection of thallium, calcium oxide, calcium hydroxide and copper.
Last Update：2022-01-01 10:33:32
Ethyl acetoacetate - Safety
Open Data Verified Data
- This product is less toxic, rat oral LD50 3.98g/kg. But with a moderate degree of irritation and anesthesia, production equipment should be sealed, good ventilation. The operator shall be provided with protective equipment.
- This product is packaged in an aluminum barrel. The lid is better sealed and stored in a cool and ventilated place for fire prevention. According to the provisions of flammable and toxic chemicals storage and transportation.
Last Update：2022-01-01 10:33:33
Ethyl acetoacetate - Reference Information
| FEMA | 2415 | ETHYL ACETOACETATE |
| relative polarity | 0.577 |
| LogP | 0.8 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| content analysis | method 1 accurately weigh about 0.8g of sample, and method 2 in pendulum aldehyde and ketone content determination method (OT-7). The maintenance time was 15min. The equivalent factor (e) in the calculation is 65.07. Method 2: Take 50ml of newly distilled pyridine, put it into a 250ml conical flask, and add about 450mg of accurately weighed sample. Cover the hanging, swirl until completely dissolved. Several drops of thymol test solution (TS-248) were titrated with 0.1mol/L sodium methoxide pyridine solution until the blue end point began to appear. When dropping, nitrogen flow through a 6mm glass tube into bottle A, the glass tube should be installed near the lower end of the burette. The blank test is carried out with the above. 0.1mol/L sodium methoxide pyridine liquid phase blue in ethyl acetoacetate (C6H10O3)13.01mg per Ml. Method 3 was determined by non-polar column method in GT-10-4. |
| toxicity | LD503.98g/kg (rat, oral). |
| usage limit | FEMA(mg/kg): soft drink 17; Cold drink 24; Candy 110; Baked food 120; Pudding 93; Gum candy 530. Moderate limit (FDA § 172.515,2000). |
| Uses | It is used in medicine to synthesize aminopyrine, vitamin B, etc., also used in the preparation of azo yellow dyes, and also used to mix apple flavors and other fruit flavors Used as a gas chromatography stationary solution, analytical reagent and complexation indicator for the determination of high iron Ethyl acetoacetate is an important organic synthesis raw material, in the production of pesticides, it is used to synthesize the intermediate α-ethyl chloroacetoacetate of the organophosphorus insecticide fly phosphorus, the intermediate 2-methoxy-4-methyl-6-hydroxypyrimidine of pyrimidine phosphorus, the intermediate of diazinon 2-isopropyl-4-methyl-6-hydroxypyrimidine and the carbamate insecticide antiaphidocarb, the fungicide hymapropin, the herbicide flavazole acetonicotinic acid, the rodenticide, the rodenticide, the rodenticide, the rom, it is also an intermediate of the new fungicides sulimidine (cyprodinil), sulfuramine (difulmetorim), furpiramide (furammetpyr) and the plant growth regulator (cintofen). In addition, ethyl acetoacetate is also widely used in medicine, plastics, dyes, spices, varnishes and additives industries. I am occasionally used in cosmetics such as gardenia, which can give the wine fruit aroma or elegant non-floral aroma. It can give ethanol a sense of roundness in washing water or water. Widely used in edible flavors, can be used in many fruit or wine flavors, such as apples, apricots, peaches, cherries, berries and rice wine, brandy, white wine, whiskey, rum and other edible flavors and wine flavors. GB 2760-96 specifies edible spices that are allowed to be used. Widely used to prepare strawberry, apple, apricot, cherry, peach and other fruit type and wine type (rum, whisky, etc.) flavor. Ethyl acetoacetate is widely used in organic synthesis. For example, it can be used to synthesize heterocyclic compounds such as pyridine, pyrrole, pyrazolone, pyrimidine, purine and cyclic lactone. It is also widely used in drug synthesis. For example, ethyl acetoacetate is cyclized with resorcinol to obtain 4-methyl-7-hydroxycoumarin, which is an anti-allergic drug scale intermediate. The condensation of ethyl acetoacetate with chlorobenzyl gives ethyl α-acetylphenylpropanate, which is an intermediate of the cough medicine cough ketone. Ethyl acetoacetate is condensed with benzoyl chloride to obtain ethyl benzoyl acetate, which is an intermediate of the central excitatory medicine lobeline hydrochloride. Ethyl acetate is cyclized with thiourea to prepare the antithyroid drug methionopyrimidine (an intermediate of the coronary dilator dipyridamole). The particularity of EAA structure determines that it has both the properties of ketones and the reaction characteristics of enols, and its chemical properties are very active. It is widely used in medicine, dyes, pesticides and other fields, as well as in food additives and flavors. The biggest use of EAA in my country is to synthesize medicine and its intermediates, mainly to synthesize γ-acetylbutyrolactone (an important intermediate of vitamin B), 4-methyl-7-hydroxycoumarin (an anti-sensitive drug Intermediate), etc.; also used to prepare acetylo-chloroaniline (synthesis 1,3, 5-Pyrazolone and Hansa Yellow Lake intermediates), acetylacetyl o-methylaniline (used to synthesize organic yellow dyes and packaging synergistic pigment yellow) and other dye intermediates; in addition, EAA is also used to produce pesticides such as Methyl pyridine phosphorus, pyridine phosphorus, etc. In foreign countries, it is also used in unsaturated polyester co-accelerators and synthetic fragrances such as the preparation of linalool, ionone and macrocyclic fragrances. Ethyl acetoacetate is also used to synthesize 4-hydroxycoumarin, and then produce new anticoagulants. Ethyl acetoacetate cyclized with 1, 3-bromochloropropane to obtain 2-methyl-3-ethoxycarbonyl-5, 6-dihydropyran. This is an intermediate of the vasodilator pentoxifylline. Ethyl acetoacetate is also used in the synthesis of diclofenazole penicillin sodium, amoxicillin, the selective coronary dilator Yantongxin and azopyrimidine. Ethyl acetoacetate is condensed with aniline to obtain 4-hydroxyquinaldine. It is used for the production of sterilizing and antiseptic drugs. An intermediate of pyrazolone derivatives and dyes formed by condensation of ethyl acetoacetate with phenylhydrazine. It also has important applications in pesticides, fragrances, photochemicals, polymerization catalysts, etc. Ethyl acetoacetate is also used as a food fragrance. Ethyl acetoacetate is also used as a solvent, and it is also a reagent for detecting thallium, calcium oxide, calcium hydroxide and copper. Used in organic synthesis, spices, dyes and pharmaceutical industries The pharmaceutical industry is used to manufacture aminopyrine, vitamin B, etc. Dye workers are used as raw materials for synthetic dyes and for dyeing film substrates. The coating industry is used to make clear. Organic industry is used as solvent and material for synthesizing organic compounds solvent. Organic synthesis. Verification of thallium. Determination of calcium oxide, calcium hydroxide and copper. Determination of complexation indicator for high iron. Gas chromatography stationary liquid (the highest degree of mixing 50 ℃, the solvent is acetone), separation and analysis of lower hydrocarbon isomers, separation of normal, iso-1-butene and cis, trans-2-butene. Used for the determination of thallium and calcium oxide, calcium hydroxide and copper; used as a complexing indicator for the determination of high iron; used as a gas chromatography stationary liquid (the maximum mixing degree is 50 ℃, the solvent is acetone), separation and analysis of lower hydrocarbon isomers, separation of normal, iso-1-butene and cis, trans-2-butene |
| production method | 1. esterification of diketene and ethanol diketene and absolute ethanol are esterified under concentrated sulfuric acid catalysis to obtain crude ethyl acetoacetate. The finished product is then rectified under reduced pressure. 2. Ethyl acetate self-condensation method is obtained by self-condensation of two molecules of ethyl acetate in the presence of metallic sodium. It is obtained by condensation and distillation of ethyl acetate in the presence of sodium ethoxide. It is obtained by esterification of diketene and absolute ethanol under concentrated sulfuric acid catalysis and then distillation under reduced pressure. the preparation method commonly used in industry is that diketene and anhydrous ethanol are esterified under the catalysis of concentrated sulfuric acid to obtain crude ethyl acetoacetate, and then the finished product is rectified under reduced pressure. Ethanol and sulfuric acid are added into the esterification pot according to the ratio, stirred and heated. When the temperature rises to 82 ℃, diketene is added dropwise, and the esterification temperature shall not exceed 130 ℃. Continue to reflux until the reaction temperature no longer changes and the esterification solution does not have diketene to end the reaction. The temperature of the feed liquid is reduced to less than 120 ℃, and the low boiling substance is removed under the condition of controlling the reflux ratio of 1:1. When the low boiling substance is no longer distillated, the vacuum degree is increased to 86.6kPa, and the low boiling substance is continued to be removed. When the top temperature of the tower rises above 100 ℃, the vacuum degree is increased to 97.3 kPa, and the finished product is distilled with a content greater than 97%. Self-condensation reaction of ethyl acetate can also be used. 2CH3COOC3H5[Na]→ CH3COCH2COOC2H5 250g of sodium metal is added to 4240mL of ethyl acetate, and the reaction starts very slowly. It needs to be warmed in a water bath. Once the reaction starts, it is very violent and needs to be cooled. Ethyl acetate was recovered by distillation after reflux reaction. Add 1375mL 56% acetic acid solution, stir and reflux, add 250g of salt, separate the oil, extract with ether, recover ether from the extract, and wash with 10% sodium bicarbonate solution until acidic. After drying with calcium chloride, distillation under reduced pressure, 76~78 ℃/2.4kPa fraction is collected as the finished product, and the yield is close to 30%. |
| category | flammable liquid |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 3980 mg/kg; Oral-mouse LD50: 5105 mg/kg |
| stimulation data | skin-rabbit 510 mg mild; Eye-rabbit 100 mg severe |
| flammability hazard characteristics | combustible in case of open flame, high temperature and strong oxidant; Combustion emission stimulates smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | foam, dry powder, carbon dioxide |
| auto-ignition temperature | 580 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:06
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Raw Materials for Ethyl acetoacetate
Downstream Products for Ethyl acetoacetate