2,4-Pentanedione
2,4-Pentanedione
CAS: 123-54-6
Molecular Formula: C5H8O2
2,4-Pentanedione - Names and Identifiers
| Name | 2,4-Pentanedione |
| Synonyms | acetyl Pentanedione acetyl-aceton Acetylacetone CH3COCH2COCH3 Acetyl Acetone pentan-2,4-dione 2,4-Pentanedione acetyl2-propanone pentane-2,4-dione acetyl-2-propanon pentane-2,3-dione Acetyl 2-propanone (3E)-4-hydroxypent-3-en-2-one (3Z)-4-hydroxypent-3-en-2-one |
| CAS | 123-54-6 |
| EINECS | 204-634-0 |
| InChI | InChI=1/C5H8O2/c1-4(6)3-5(2)7/h3,6H,1-2H3/b4-3- |
| InChIKey | YRKCREAYFQTBPV-UHFFFAOYSA-N |
2,4-Pentanedione - Physico-chemical Properties
| Molecular Formula | C5H8O2 |
| Molar Mass | 100.12 |
| Density | 0.975 g/mL at 25 °C (lit.) |
| Melting Point | -23 °C (lit.) |
| Boling Point | 140.4 °C (lit.) |
| Flash Point | 66°F |
| Water Solubility | 16 g/100 mL (20 ºC) |
| Solubility | H2O: soluble1 in 8 parts |
| Vapor Presure | 6 mm Hg ( 20 °C) |
| Vapor Density | 3.5 (vs air) |
| Appearance | Liquid |
| Color | very deep green-yellow |
| Odor | pleasant odor |
| Exposure Limit | No exposure limit has been set. |
| Merck | 14,81 |
| BRN | 741937 |
| pKa | 8.9(at 25℃) |
| PH | 6 (200g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Explosive Limit | 2.4-11.4%(V) |
| Refractive Index | n20/D 1.452(lit.) |
| Physical and Chemical Properties | A colorless or yellowish, flowable, transparent liquid with the odor of an ester that condenses into shiny crystals on cooling. Upon exposure to light, it is converted into a brown liquid and a resin is formed. Melting Point -23 ℃, boiling point 140.5 ℃,139 ℃(94.5kPa), relative density 0.9753, refractive index 1.4494, flash point 40.56 ℃, soluble in water, ethanol, ether, chloroform, acetone, benzene, glacial acetic acid. Industrial products have an unpleasant odor and are easily hydrolyzed to acetic acid and acetone. |
| Use | Used as raw materials and pharmaceutical organic intermediates, can also be used as solvents |
2,4-Pentanedione - Risk and Safety
| Risk Codes | R11 - Highly Flammable R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed R10 - Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R2017/10/22 - |
| Safety Description | S21 - When using do not smoke. S23 - Do not breathe vapour. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2310 3/PG 3 |
| WGK Germany | 1 |
| RTECS | SA1925000 |
| FLUKA BRAND F CODES | 9-23 |
| TSCA | Yes |
| HS Code | 2914 19 90 |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | LC50 (4 hrs) in rats: 1000 ppm (Carpenter) |
2,4-Pentanedione - Upstream Downstream Industry
| Raw Materials | Acetone Acetic acid |
| Downstream Products | 2,4-Dimethyl-5-acetylthiazole 2,4-Pentanedione Sulfamethazine Base Aluminum acetylacetonate |
2,4-Pentanedione - Nature
Open Data Verified Data
a colorless, flowable liquid with the odour of an ester condenses into shiny crystals on cooling. Upon exposure to light, it is converted into a brown liquid and a resin is formed. Relative density 0.9753. Boiling point 140.5 °c. Melting Point -23 °c. Flash point 40. 56 °c. Refractive index 4494. Soluble in water, ethanol, chloroform, ether, benzene, acetone and acetic acid.
Last Update：2024-01-02 23:10:35
2,4-Pentanedione - Preparation Method
Open Data Verified Data
- acetone and acetic anhydride condensation method: the process is simple, mature and high yield. However, boron trifluoride is a dangerous gas, which is inconvenient to use and difficult to treat waste liquid.
- ethyl acetate acetone method: This method is a classical synthesis method. This process requires the use of metal sodium, which brings a certain degree of danger to the industrial production.
- ethyl acetoacetate acetic anhydride method: the process is simple, convenient, equipment investment is small, but its technical and economic indicators are not ideal, the cost of raw materials is equivalent to the price of imported products.
- ethyl acetoacetate-ketene method: but this method has mild reaction conditions and high yield. But the process is long, the price of raw materials is high, and the investment is large.
- ketene-acetone condensation conversion method.
- acetone-ethyl acetate method.
Last Update：2022-01-01 10:17:10
2,4-Pentanedione - Use
Open Data Verified Data
organic synthesis of intermediates, with the formation of guanidine amino 4,6-methyl Pyrimidine as important pharmaceutical raw materials. It can be used as solvent of cellulose acetate, additive of gasoline and lubricant, desiccant of paint and varnish, bactericide, insecticide, etc. Acetylacetone can also be used as a catalyst for petroleum cracking, hydrogenation reaction and carbonylation reaction, oxidation promoter of oxygen, etc.
Last Update：2022-01-01 10:17:11
2,4-Pentanedione - Safety
Open Data Verified Data
- moderate toxicity. Can stimulate the skin, mucous membranes, when the human body in (150~300)× 10-6 under a long stay can suffer, appear Head Pain, Nausea, Vomit, dizziness and sensory retardation and other symptoms, but at a concentration of 75 x 10-6, there is no danger. Production should use vacuum sealing device. The operation site should be strengthened ventilation, minimize run, run, drop, leakage. If poisoning occurs, you should leave the scene as soon as possible and breathe fresh air. Operators should wear protective month equipment, and regular occupational disease inspection.
- packed with an iron drum lined with a plastic bag or plastic drum; 250kg per barrel. Fire, moisture, storage in the dangerous goods warehouse. Hazardous chemicals shall be stored and transported according to regulations.
Last Update：2022-01-01 10:17:11
2,4-Pentanedione - Reference Information
| relative polarity | 0.571 |
| LogP | 0.68 at 20℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| acetone derivatives | acetylacetone, also known as diacetyl methane, pentanedione, is a derivative of acetone, molecular formula ch3och2och3, colorless to light yellow transparent liquid. It is usually a mixture of two tautomers, the enol and the ketone, which are in dynamic equilibrium, and the enol isomers form hydrogen bonds in the molecule. In the mixture, the ketone is about 18%, enol accounted for 82%. When the petroleum ether solution of the mixture was cooled to -78 °c, the enol form was precipitated as a solid and the two were separated; When the enol form returned to room temperature, it was again automatically in the above-mentioned equilibrium state. acetylacetone has a pleasant odor. Flammable. Relative molecular mass 100.13. Relative density 0.9721(25 degrees C). Melting Point -23.5 °c. Boiling point 140.5 C, 139 C (99.458 X 103Pa). Flash point 41. Refractive index 1.4494. The vapor pressure was 0.800 × 103Pa(20 ° C.). Soluble in water (20 ° C 16.9, 80 ° C 34), ethanol, benzene, chloroform, ether, acetone, ethyl acetate and acetic acid. It is easily hydrolyzed to acetic acid and acetone by water. The molecular structure of acetylacetone is a saturated diketone in which two hydroxyl groups are linked together by a methylene group. This form is commonly referred to as a beta diketone. Acetylacetone is also the simplest saturated β-diketone, a derivative of acetone. Its chemical activity, and ferric chloride aqueous solution, a deep red. This product can react with almost all metal hydroxide, carbonate or acetate to form a complex. The general formula of the complex is:(C5H7O2)· M, where M is a metal, and n is a compound of the metal. Most of these compounds are stable and many are soluble in organic solvents. This product can react with chlorine under light, and only the hydrogen in the methyl group at both ends can be replaced by chlorine. This product reacts with sodium, can release hydrogen, and generate sodium acetylacetone. Acetylacetone has anesthetic effect, stimulate the skin and mucous membranes, in high concentrations (100 x 10-6 above), easy to produce Nausea, Head Pain, dizziness and other symptoms of poisoning. Rat oral LD50970mg/kg. |
| organic synthesis intermediate | acetylacetone is an important organic synthesis intermediate, widely used in pharmaceuticals, spices, pesticides and other industries. acetylacetone is an important raw material in the pharmaceutical industry, such as the synthesis of 4, 6-dimethylpyrimidine derivatives. It is also used as a solvent for cellulose acetate, a desiccant for paints and varnishes, and is also an important analytical reagent. due to the presence of the enol type, acetylacetone can be associated with metal cobalt (II), cobalt (III), beryllium, aluminum, chromium, iron (II), copper, nickel, palladium, zinc, indium, tin, zirconium, magnesium, manganese, scandium and thorium and other metal ions to form chelates, can be used as fuel oil additives and lubricating oil additives. by its chelation with metal, it can be used as a cleaning agent for metal in micropores; Used as catalyst, resin crosslinking agent, resin curing accelerator; Resin, rubber additive; Used for hydroxylation reaction, hydrogenation reaction, isomerization reaction, synthesis of low molecular unsaturated ketone and polymerization and copolymerization of light olefins; Used as organic solvent for cellulose acetate, ink, pigment; Paint desiccant; Preparation of insecticidal, bactericide raw materials, livestock antidiarrheal and feed additives; Infrared reflective glass, transparent conductive film (indium salt), superconducting film (Indium salt) forming agent; Acetylacetone metal complex has a special color (copper salt Green, iron salt red, chromium salt purple) and insoluble in water; Used as a pharmaceutical raw material; Organic synthesis raw material. |
| preparation method | 1, ethyl acetate and acetone are condensed under the action of metal sodium, and the reacted ethyl acetate is recovered, the residue was neutralized with acetic acid, and then copper acetate solution was added. Due to the chelating effect of acetylacetone, a green precipitate of copper acetylacetonate chelate was generated, after the ether is recovered, the residue is separated by distillation to obtain crude acetylacetone. The crude acetylacetone is extracted and refined with benzene (or ethanol) to obtain refined acetylacetone. 2. Acetylacetone can be obtained by reacting acetyl chloride with acetone in an inert solvent under the action of aluminum trichloride. 3, with acetone and ketene as raw materials, in the presence of sulfuric acid, reaction at 60~70 ℃, After purification, at high temperature (560~570 deg C) to gasification, through molecular rearrangement, can be obtained acetylacetone. In this process, the following equilibrium may occur: in order to obtain more acetylacetone, the formation of enol should be minimized, and the temperature should not be too high. After the crude acetylacetone was obtained, it was refined by distillation under reduced pressure. 4, ketene can be directly obtained by heating acetone at 700 ℃; Acetone is converted to allyl alcohol; Ketene and allyl alcohol react to form isoallyl acetate, the ester is converted into acetylacetone at 480~520 ℃ and refined by rectification to obtain a refined product. The biggest advantage of this process is only one kind of raw material of acetone. 2.55t of raw material is required per 1t of product. |
| Use | pentanedione, also known as acetylacetone, is an intermediate of the fungicide, methylamine, pyrimidine and the herbicide sulfuron-methyl. used as pharmaceutical raw materials and organic intermediates, can also be used as solvent used as analytical reagents and extraction agent of aluminum in tungsten and molybdenum acetylacetone is an intermediate in organic synthesis, with guanidine to produce amino -4, 6-dimethylpyrimidine, is an important pharmaceutical raw materials. It can be used as solvent of cellulose acetate, additive of gasoline and lubricant, desiccant of paint and varnish, bactericide, insecticide, etc. Acetylacetone can also be used as a catalyst for petroleum cracking, hydrogenation reaction and carbonylation reaction, oxidation promoter of oxygen, etc. It can be used to remove metal oxides from porous solids and to treat Polypropylene Catalysts. In Europe and the United States more than 50% for anti-diarrheal livestock and feed additives. In addition to the typical properties of alcohols and ketones, it also shows a deep red color with ferric chloride and forms chelates with many metal salts. It is prepared by the condensation of acetic anhydride or acetyl chloride with acetone, or by the reaction of acetone with ketene. It is used as a metal extractant to separate trivalent and tetravalent ions, paint and ink desiccant, pesticide Insecticide, Fungicide, Polymer solvent, reagent for determination of thallium, iron, fluorine and organic synthesis intermediates. Transition metal chelator. Colorimetric Determination of iron and fluorine, determination of thallium in the presence of carbon disulfide. Fe(III) Complexometric titration indicator; For guanidino (such as Arg) and amino group modification in protein used as transition metal chelator; For Colorimetric Determination of iron and fluorine, determination of thallium in the presence of carbon disulfide An indicator for iron (III) Complexometric titration. Used to modify guanidyl groups in proteins and amino groups in proteins. |
| production method | Different process routes can be used: acetone is reacted with ketene or acetic anhydride is condensed with acetone or acetone is condensed with ethyl acetate. Acetone and ketene reaction process, in fact, acetone as raw material, by ketene, isopropene acetate, and then through the conversion of acetylacetone; Process is as follows: the acetone containing 1/1000 carbon disulfide is gasified and then introduced into a cracking furnace at 780-800 ° C. To generate ketene (or glacial acetic acid is gasified by the presence of triethyl phosphate catalyst, ammonia is used as a stabilizer, cracking furnace at 700 ° C to ketene), ketene with acetone absorption, in the presence of sulfuric acid or acetyl sulfonyl, at 61-71 ° C to react with acetic acid to form isopropenyl acetate, after fractionation and purification, the purity of isopropyl acetate can reach more than 93-95%. Then, the isopropenyl acetate is gasified and introduced into a reformer preheated to 560-570 ° C. To generate acetylacetone through molecular rearrangement, which is condensed, fractionated and purified to obtain a finished product. Approximately 2700kg of acetone was consumed per ton of product. The condensation of acetone with ethyl acetate is carried out in the presence of metallic sodium. Working example 1 a cooled beaker was charged with 120ml of purified ethyl acetate and 32ml of ammonia gas. After completion of the addition of sodium amino acid, it was left overnight at room temperature after shaking in ice water for 24 hours. The next day, 100g of ice was added, followed by the same amount of ice water, and the aqueous layer was taken and made acidic by adding dilute sulfuric acid. To this solution was added a saturated solution of copper acetate (obtained by dissolving 40g of powdered copper acetate plus a certain amount of hot water). The copper salt was precipitated from acetylacetone. If the reaction solution is alkaline, a small amount of acetic acid may be added. After 2-3H, the gray acetylacetone was suction filtered, washed twice with water, transferred directly into a separatory funnel, and decomposed by adding 50ml of 4n sulfuric acid while shaking with diethyl ether. The diethyl ether solution was taken and the acetylacetone in the acid layer was extracted with diethyl ether. The diethyl ether solutions were combined twice and dried with calcium chloride. The residue was distilled off from the ether and the distillation was continued and the 125-140 °c fraction was collected. Then concentrate at 135-140 ℃, about 15-20g. Boiling point 139 °c. Working example 2 in a 1500ml round bottom flask, 25g of sodium metal and 20ml of diethyl ether were added, followed by 225ml of ethyl acetate cooled with a coolant. 73ml of acetone was added with cooling and constant stirring. At room temperature for 4H, 400ml of water were added, the ethyl acetate on the water layer was separated, the aqueous layer was neutralized with acetic acid, and then a copper acetate solution (125g of copper acetate in 1500ml of water) was added to form the Green acetylacetone chelate. After 2-3H, the precipitation was complete and filtered. The precipitate was suspended in ether, shaken with 50ml of 40% dilute sulfuric acid and the ether layer was dried over calcium chloride. The ether was distilled off and the residual oil was fractionated. The 124-140 °c fraction was collected and fractionated to collect the 139-140 °c fraction. The condensation reaction of acetic anhydride and acetone was carried out under the catalysis of boron trifluoride. Acetylacetone refining method: about 20ml acetylacetone crude dissolved in 80ml benzene, This was then shaken for 3H with an equal volume of distilled water. Acetic acid, which is readily soluble in water, partitions into the aqueous phase, while acetylacetone is readily soluble in benzene. The acetylacetone in the benzene phase can be applied directly or the benzene can be distilled off. Raw material consumption quota: acetone (industrial products, water content <0.5%)2553kg/t, fuming sulfuric acid (based on H2SO4) 12kg/t, acetic anhydride (95%)19kg/t, carbon disulfide (chemical pure) 6kg/t. The preparation method is that the acetophenone produced by the cleavage of acetic acid is absorbed with acetone, and isopropenyl acetate is formed in the presence of sulfuric acid or acetylsulfonyl acetic acid at 67~71 ℃, after separation and purification, at 500~600 deg C through molecular rearrangement to form Acetyl acetone, and finally fractionated purified to obtain the finished product. |
| category | flammable liquid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 55 mg/kg; Oral-mouse LD50: 951 mg/kg |
| stimulation data | Skin-rabbit 488 mg mild; Eye-rabbit 20 mg mild |
| 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 |
| spontaneous combustion temperature | 662 ° F. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:04
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Raw Materials for 2,4-Pentanedione
Downstream Products for 2,4-Pentanedione