Basic information Flavorants Toxicity Application limitation Chemical Properties Uses Production method Safety Related Supplier
Benzalacetone Chemical Properties
- Melting point:39-42 °C(lit.)
- Boiling point:260-262 °C(lit.)
- Density 1.038
- vapor pressure 0.01 mm Hg ( 25 °C)
- refractive index 1.5836
- FEMA 2881 | 4-PHENYL-3-BUTEN-2-ONE
- Flash point:150 °F
- storage temp. Store at <= 20°C.
- solubility Soluble in alcohol, chloroform, diethyl ether.
- form Low Melting Solid
- color Pale yellow to yellow
- Water Solubility 1.398g/L(25 ºC)
- Sensitive Light Sensitive
- Merck 14,1137
- JECFA Number820
- BRN 742046
- CAS DataBase Reference122-57-6(CAS DataBase Reference)
- NIST Chemistry Reference3-Buten-2-one, 4-phenyl-(122-57-6)
- EPA Substance Registry SystemBenzylideneacetone (122-57-6)
Benzalacetone Usage And Synthesis
- FlavorantsOur 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.
- ToxicityIt can be safely used in food (FDA, §172.515,2000).
- Application limitationFEMA (mg/kg): Soft drinks 0.82 ; cold drinks 0.84; confectionery 3.7; bakery 4.5;jelly and pudding 2.1 ; shortening 0.20.
- Chemical PropertiesIt is colorless crystals. It has a coumarin odor. It is soluble in alcohol, ether, benzene and chloroform, slightly soluble in water and petroleum ether.
- Uses1. 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 methodUsing 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 PropertiesYellow Solid
- Chemical Properties4-Phenyl-3-buten-2-one has a sweet, floral, creamy, pungent odor reminiscent of coumarin and rhubarb with a sweet, pungent flavor. It is not very stable.
- OccurrenceReported found in hydrolyzed soy protein, soybeans and Virginia tobacco.
- Usesbrightener in acid zinc electroplating,also used as an organic synthesis intermediate in flavor and fragrance, pharmaceutical industries
- UsesIn perfumery, organic syntheses.
- DefinitionChEBI: An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ket ne, only the trans-isomer is observed.
- PreparationBy condensing benzaldehyde and acetone in the presence of an alkaline condensing agent.
- Aroma threshold valuesAroma characteristics at 1.0%: sweet, fruity and jamy cherry-like, aldehydic cinnamon spicy, herbal, anisic, balsamic, toasted almond nutty and woody with slight powdery vanilla nuances.
- Taste threshold valuesTaste characteristics at 5 to 10 ppm: aldehydic, coumarinic and balsamic, slightly nutty, floral and fruity with woody nuances.
- Synthesis Reference(s)The Journal of Organic Chemistry, 58, p. 5595, 1993 DOI: 10.1021/jo00073a011
Tetrahedron Letters, 28, p. 913, 1987 DOI: 10.1016/S0040-4039(00)95872-6
- Safety ProfilePoison by intravenous route. Moderately toxic by intraperitoneal route. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.
- Purification MethodsCrystallise it from pet ether (b 40-60o), or distil it (b 137-142o /16mm). [Beilstein 7 IV 1003.]
Benzalacetone Preparation Products And Raw materials
- 4,4'-(Disulfanediyl)bis(2,6-di-tert-butylphenol) (S)-8-Hydroxy Warfarin 6-HYDROXYWARFARIN 4-Hydroxycoumarin (R)-8-HYDROXY WARFARIN (R)-6-Hydroxy Warfarin 3-(o-Hydroxyphenyl)-5-phenyl-2-cyclohexen-1-one 3-[α-(2-Hydroxypropyl)benzyl]-4-hydroxycouMarin (R)-7-Hydroxy Warfarin 7-HYDROXYWARFARIN (S)-6-Hydroxy Warfarin Warfarin Impurity 1 8-HYDROXYWARFARIN 2,6-Di-tert-butyl-4-mercaptophenol 7-HYDROXYWARFARIN Warfarin Impurity 3 Warfarin Impurity 4 Warfarin Impurity 5
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