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CAS NO.122-57-6
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| Benzalacetone Basic information |
| Product Name: | Benzalacetone |
| Synonyms: | (3E)-4-Phenyl-3-buten-2-one;1-Buten-3-one-1-phenyl;2-Phenylvinyl methyl ketone;4-phenyl-3-buten-2-on;4-Phenyl-but-3-en-2-one;4-Phenylbut-3-en-2-one;4-Phenylbutenone;Benzalaceton |
| CAS: | 122-57-6 |
| MF: | C10H10O |
| MW: | 146.19 |
| EINECS: | 204-555-1 |
| Product Categories: | Pharmaceutical Intermediates;Aromatic Ketones (substituted);Aromatics;Building Blocks;C10;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks |
| Mol File: | 122-57-6.mol |
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| Benzalacetone Chemical Properties |
| mp | 39-42 °C(lit.) |
| bp | 260-262 °C(lit.) |
| density | 1.038 |
| vapor pressure | 0.01 mm Hg ( 25 °C) |
| FEMA | 2881 |
| refractive index | 1.5836 |
| Fp | 150 °F |
| Sensitive | Light Sensitive |
| Merck | 14,1137 |
| BRN | 742046 |
| CAS DataBase Reference | 122-57-6(CAS DataBase Reference) |
| NIST Chemistry Reference | 3-Buten-2-one, 4-phenyl-(122-57-6) |
| EPA Substance Registry System | 3-Buten-2-one, 4-phenyl-(122-57-6) |
| Safety Information |
| Hazard Codes | Xn,Xi |
| Risk Statements | 36/37/38-43-42/43 |
| Safety Statements | 7-26-36/37/39-45-37/39-24-36/37-22 |
| WGK Germany | 3 |
| RTECS | EN0330050 |
| F | 8 |
| HS Code | 29143900 |
| MSDS Information |
| Provider | Language |
|---|---|
| 4-Phenyl-3-buten-2-one | English |
| ACROS | English |
| SigmaAldrich | English |
| ALFA | English |
| Benzalacetone Usage And Synthesis |
| Flavorants |
Our GB2760-1996 provisions temporarily allow benzalacetone as a food spice, it is used to modulate sweet pea, cocoa, nuts, cherries, fruit flavor aroma, also used as floral flavor variable swap and anti-propellant, because of the stimulating effect on the skin, it is generally not used in cosmetics. Also benzalacetone can also be used as a mordant, fixing agent and preparation galvanized credit agent in dyeing industry. Credit agent is an organic compound capable of producing bright and leveling effect. Usually it contains aromatic aldehydes or ketones and certain heterocyclic aromatic aldehydes, ie coumarin, vanillin, benzalacetone, its molecular structure contains a carbonyl group, just keeps this structure intact, substituting various substituents, it can produce many kinds of compounds having light effects. Among these, benzalacetone displays best effects, domestic commercial additives are mostly based on such benzalacetone predominating brightener. The most commonly used method is based on the preparation of benzaldehyde and acetone as raw materials, to carry out the Claisen reaction, in the presence of a base (sodium hydroxide or sodium carbonate), aldehydes and ketones condensate, after completing the reaction, diluted hydrochloric acid is added and adjusted to pH = 6-7, set still for stratification, the upper yellow oil is separated, in order to maximize the yield, the lower layer is extracted with benzene, the extract is dried after recovery of benzene, and the oil is combined, then washed with water, separate the oil , bleached with activated carbon, filtered, and purified by vacuum steam distillation, cooled and crystallized, to get crude benzalacetone . Benzalacetone is also known as 4-phenyl-3-butene-2-one, dibenzylideneacetone, cinnamyl methyl ketone, benzal acetone, methyl styryl ketone. The product abtained by vacuum distillation system is colorless to pale yellow shiny lamellae. It owns sweet pea fragrance and spicy and pungent flavor, changes to deep color exposed in light, combustible, prolonged heat leading to decomposition. Naturally it presents in hydrolyzed soy protein. The formations include cis and trans. Relative molecular mass is 146.19. The relative density is 1.0076 (47.3 ℃). The freezing point is 39 ℃, the melting point is 42 ℃. The boiling point is 261 ℃, 211 ℃ (26.664 × 103Pa), 187.8 ℃ (13.332 × 103Pa), 161.3 ℃ (5.333 × 103Pa), 143.8 ℃ (2.666 × 103Pa), 127.4 ℃ (1.333 × 103Pa), 112.2 ℃ (0.666 × 103Pa ), 81.7 ℃ (0.133 × 103Pa). The refractive index is 1.5836 (45.9 ℃). It is slightly soluble in water and petroleum ether, slightly soluble in benzene, soluble in ethanol, benzene, ether, chloroform and sulfuric acid. It displays a reddish color while reacting with sulfuric acid, this feature can be used to detect the product. The above information is edited by the Chemicalbook of Tian Ye. |
| Toxicity | It can be safely used in food (FDA, §172.515,2000). |
| Application limitation | FEMA (mg / kg): Soft drinks 0.82 ; cold drinks 0.84; confectionery 3.7; bakery 4.5;jelly and pudding 2.1 ; shortening 0.20. |
| Standards for Use of Food Additives |
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| Chemical Properties | It is colorless crystals. It has a coumarin odor. It is soluble in alcohol, ether, benzene and chloroform, slightly soluble in water and petroleum ether. |
| Uses |
1. It is used for the preparation of spices and galvanized brightener. 2. GB 2760--1996 allows it used as food with spices. Formulated balm, cherries, grapes, berries, anise-based and other flavors for temporary . 3. This product is used as galvanized additives, coating materials to increase the brightness. The dyeing industry uses it as a mordant in dyeing agent to improve the uniformity and firmness, also it can be used for the preparation of spices and flavoring agents. 4. 4-phenyl-butene (3)one-2 is one rodenticide warfarin intermediates. 5. As an aromatic organic substance, it is the most widely superior light additive in acid zinc plating process , in the potassium chloride, ammonium plating process, it can get bright coating in a very wide current density and the temperature range, play a good effect on the coating of the internal stress, anti-corrosion ability. This product is also available anti volatile agent for spices, mordant and fixing agent in dyeing industry, it can also be used to prepare spices flavoring agent. 6. Organic synthesis intermediates. It can be used as a spice anti propellant. In dyeing industry,it is used as mordant , fixing agent, it is used for the preparation of spices or flavoring agents, and preparation for galvanized credit agent. |
| Production method | Using Benzaldehyde for raw materials, and carrying out condensation reaction with acetone . Benzaldehyde and acetone, mixed with water, cooled slowly, added 10% sodium hydroxide solution, the temperature controlled at 25-31°C, After the addition, the stirring was continued for 1h. Then diluted hydrochloric acid was added to pH 6-7, set still for 1h, isolated as a yellow oil. Lower layer was extracted with benzene, the extract and oil were combined, washed twice with water, after the separation the layer of water, recovered benzene, and then dried over calcium chloride, dry decolorizing charcoal was added , filtered and the filtrate vacuum distillation derived products. . Fixed material consumption : benzaldehyde 1700kg / t, acetone 2900kg / t, caustic soda (40%) 500kg / t. |
| Chemical Properties | Yellow Solid |
| Usage | brightener in acid zinc electroplating,also used as an organic synthesis intermediate in flavor and fragrance, pharmaceutical industries |
| Benzalacetone Preparation Products And Raw materials |
| Raw materials | Acetone-->Formaldehyde-->Water-->Benzaldehyde-->Phenylacetone |
| Preparation Products | Cinnamic acid -->3,4-DIBROMO-4-PHENYL-2-BUTANONE |
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