| HS Code | 800215 |
| Chemical Name | Ethyl acetoacetate |
| Chemical Formula | C6H10O3 |
| Molecular Weight | 130.14 g/mol |
| Cas Number | 141-97-9 |
| Appearance | Colorless to pale yellow liquid |
| Odor | Fruity, pleasant odor |
| Density | 1.021 g/cm3 at 25 °C |
| Melting Point | -45 °C |
| Boiling Point | 180.8 °C |
| Flash Point | 70 °C (closed cup) |
| Solubility | Slightly soluble in water; miscible with most organic solvents |
| Refractive Index | 1.4194 at 20 °C |
As an accredited Ethyl acetoacetate EAA factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Ethyl acetoacetate (EAA) is packaged in 200 kg sealed steel drums, protected from moisture and light. |
| Container Loading (20′ FCL) | 20′ FCL: Ethyl acetoacetate loaded in steel drums on wooden pallets, secured, labeled, with ventilation and spill containment. |
| Shipping | Ethyl Acetoacetate (EAA) is a clear, combustible liquid with a mild fruity odor. For shipping, it is not classified as dangerous goods under prevailing regulations when packaged correctly. Transport in sealed drums or IBCs, kept away from strong oxidizers and ignition sources. Protect from moisture and excessive heat. Avoid skin/eye contact. |
| Storage | Store ethyl acetoacetate in a tightly sealed container in a cool, dry, well-ventilated area away from heat, open flames, and direct sunlight. Keep it separate from strong oxidizers, acids, and bases. Ensure the container is clearly labeled and regularly checked for leaks to prevent vapors accumulating. |
| Shelf Life | Shelf life approximately 2-3 years when stored tightly sealed in a cool, dry, dark place away from moisture and heat. |
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Ethyl acetoacetate EAA (CAS 141-97-9; EINECS 205-516-1; molecular formula C6H10O3; molar mass 130.14 g/mol) is supplied as a clear, low-viscosity liquid with a boiling point of 180.8°C at 101.3 kPa, a density of 1.028–1.032 g/cm³ at 20°C, and a flash point of 65–70°C by ASTM D56-22. The product is designated by purity grade rather than model number: technical-grade EAA has an assay specification of ≥99.0% by GC-FID, while refined-grade EAA is specified at ≥99.5%. The keto-enol equilibrium in the neat liquid contains 7–8% enol at 20°C, giving an active methylene pKa of 10.68 in water at 25°C. The compound is transported in 200 L HDPE drums or stainless-steel ISO containers and is stored under nitrogen blanketing to maintain water content below 0.10 wt%.
| Parameter | Technical grade | Refined grade | Test method |
|---|---|---|---|
| Appearance | Clear, free of suspended matter | Clear, free of suspended matter | Visual inspection |
| Assay as ethyl acetoacetate | ≥99.0% | ≥99.5% | GC-FID, internal standard |
| Water content | ≤0.10 wt% | ≤0.05 wt% | ASTM E203-16 |
| Acidity as acetic acid | ≤0.10 wt% | ≤0.05 wt% | ASTM D1613-17 |
| Color | ≤15 Pt-Co | ≤10 Pt-Co | ASTM D1209-05(2019) |
| Density at 20°C | 1.028–1.032 g/cm³ | 1.028–1.032 g/cm³ | ASTM D4052-22 |
| Refractive index nD20 | 1.4180–1.4200 | 1.4180–1.4200 | ISO 5661:2018 |
| Boiling range | 178–182°C | 180–181°C | ASTM D1078-11(2019) |
| Flash point, closed cup | 65–70°C | 65–70°C | ASTM D56-22 |
Because EAA hydrolyzes slowly in the presence of water and acids, the ≤0.10 wt% water limit is used to suppress acid value drift during storage at 25°C. Published data for this specific configuration is limited, but supplier certificates for refined grade typically specify iron below 1 mg/kg because dissolved iron accelerates yellowing. Rectification for refined grade is conducted in batch columns with 316L stainless steel structured packing equivalent to 20 theoretical stages at a reflux ratio of 2:1 to 3:1; this equipment configuration reduces residual ethanol below 0.05 wt%. Carbon steel transfer lines are not used for color-sensitive material because iron contamination can shift the liquid color above 10 Pt-Co during extended storage.
In pharmaceutical intermediate synthesis, EAA is employed as a 1,3-dicarbonyl building block for pyrazole, coumarin, pyrimidine, and dihydropyridine ring construction. The Knorr pyrazole condensation with hydrazine hydrate is controlled by adding the hydrazine at 0–5°C to a solution of EAA in ethanol, then raising the batch to 70–75°C for 2 h; the molar charge is 1.00 mol EAA to 1.05 mol hydrazine. The Biginelli reaction with urea and a substituted benzaldehyde is run in ethanol at 78°C with 0.10 molar equivalents of hydrochloric acid; moisture above 0.20 wt% in the EAA feed is avoided because it shifts the acid-catalyzed equilibrium toward hydrolysis. Transesterification to methyl acetoacetate for lower-boiling downstream processing is performed with titanium(IV) isopropoxide at 65°C and methanol, with continuous removal of ethanol by distillation. The enolate is generated with sodium ethoxide in tetrahydrofuran at 0–5°C; the addition is exothermic, and the batch temperature is held below 5°C because the reaction mass darkens if local temperature exceeds 20°C.
At 20°C, EAA has a lower enol content than acetylacetone by approximately 69 percentage points and a boiling point 11°C higher than methyl acetoacetate. These differences alter solvent recovery and reactivity rather than product identity in many condensation routes. The higher boiling point reduces evaporative loss during reflux at 170–180°C, but increases energy demand in atmospheric distillation; vacuum rectification at 50–80 mbar is used to keep reboiler temperature below 120°C and suppress thermal discoloration. Compared with acetylacetone, EAA forms weaker chelates with transition-metal catalysts, which can be advantageous when residual metal removal is required by ion-exchange adsorption. Published data for this specific chelation comparison is limited, and metal-binding strength must be verified by potentiometric titration under the actual solvent system.
| Property | Ethyl acetoacetate EAA | Methyl acetoacetate | Acetylacetone | Diethyl malonate |
|---|---|---|---|---|
| CAS number | 141-97-9 | 105-45-3 | 123-54-6 | 105-53-3 |
| Molar mass | 130.14 g/mol | 116.12 g/mol | 100.12 g/mol | 160.17 g/mol |
| Boiling point | 180.8°C | 169–170°C | 140.4°C | 199.3°C |
| Density at 20°C | 1.028 g/cm³ | 1.076 g/cm³ | 0.975 g/cm³ | 1.055 g/cm³ |
| Flash point, closed cup | 65–70°C | 70°C | 34°C | 93°C |
| Enol content | 7–8% | 7% | 76–80% | <1% |
Replacement of methyl acetoacetate with EAA in transesterification-driven processes shifts the equilibrium because ethanol is released instead of methanol. This requires a higher reaction temperature or more efficient distillative removal of ethanol at 78°C as an azeotrope with toluene in batch reactors equipped with Dean-Stark traps. Compared with diethyl malonate, EAA is a ketoester rather than a diester; the active methylene is flanked by one ester and one ketone, which directs alkylation and acylation to the substituted carbon and permits subsequent ketonic cleavage. Differences in flash point are significant for process safety: acetylacetone at 34°C closed cup is classified as a more volatile flammable liquid than EAA at 65–70°C, which places EAA in a less volatile handling regime under closed-system transfer.
Residual ethanol concentration is controlled below 0.10 wt% in agrochemical intermediate synthesis because ethanol competes in transesterification and can generate mixed esters that carry through to the final active ingredient. Chloride content is specified below 10 mg/kg by suppressed ion chromatography when EAA is used in routes that involve palladium-catalyzed coupling, because chloride poisons supported palladium catalysts at loadings above 0.5 mol%. The ketonic hydrolysis behavior of EAA is exploited to generate acetone, ethanol, and carbon dioxide under controlled acidic conditions; this route is used to remove the acetoacetate moiety after condensation. In glass-lined batch reactors, the exotherm from hydrolysis is managed by gradual addition of aqueous acid at 10–15°C and by limiting acid concentration to 1–2 mol/L to avoid uncontrolled carbon dioxide release.
In two-component coating systems, ethyl acetoacetate is added at 1.5–3.0 wt% of total resin solids as a diluent and viscosity reducer. Mixing is performed with a high-shear disperser at 800–1,200 rpm for 15–20 min; homogeneity is checked by measuring viscosity according to ISO 2884-1:2024 or ASTM D2196-20. EAA reacts with primary and secondary amines at ambient temperature to form enamines, so amine-functional hardeners are incompatible unless the EAA is first protected as the enol ether. Moisture sensitivity in polyurethane systems is managed by using molecular sieves 3A to hold water content below 0.05 wt% prior to addition. In solvent-based gravure inks, EAA serves as a slow-evaporating oxygenated solvent; the boiling point of 180.8°C at 101.3 kPa places it between propylene glycol methyl ether acetate and diethylene glycol monoethyl ether in volatility.
Storage of EAA in unlined mild steel is incompatible with low color specifications because iron contamination accelerates oxidative discoloration; 316L stainless steel or HDPE is used for long-term storage. The material is not listed as a peroxide-forming substance, but exposure to strong bases in the presence of air generates resinous condensates that can foul transfer lines. Avoid combination with amine-based additives unless enamine formation is part of the intended process. Drums should be sealed under nitrogen after each withdrawal and stored at 5–30°C. At relative humidity above 60%, open transfers are replaced by closed nitrogen-padded loading to prevent water uptake above specification. The transport classification is flammable liquid, Class 3, Packing Group III under UN 1993; containers are grounded and bonded during transfer.
