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Benzaldehyde

description Synthesis reactions Toxicity Uses

CAS No. 100-52-7
Chemical Name: Benzaldehyde
Synonyms: BALD;NA 1989;FEMA 2127;NCI-C56133;Benaldehyde;Benzaldehyd;BENZALDEHYDE;Benzyaldehyde;Benzoylhydride;phenylmethanal
CBNumber: CB6852588
Molecular Formula: C7H6O
Formula Weight: 106.12
MOL File: 100-52-7.mol
Benzaldehyde Property
Melting point : -26 °C
Boiling point : 179 °C
density : 1.044 g/cm 3 at 20 °C(lit.)
vapor density : 3.7 (vs air)
vapor pressure : 4 mm Hg ( 45 °C)
FEMA : 2127
refractive index : n20/D 1.545(lit.)
Fp : 145 °F
storage temp. : room temp
solubility : H2O: soluble100mg/mL
pka: 14.90(at 25℃)
PH: 5.9 (1g/l, H2O)
explosive limit: 1.4-8.5%(V)
Water Solubility : <0.01 g/100 mL at 19.5 ºC
FreezingPoint : -56℃
Sensitive : Air Sensitive
Merck : 14,1058
BRN : 471223
Stability:: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, reducing agents, steam. Air, light and moisture-sensitive.
CAS DataBase Reference: 100-52-7(CAS DataBase Reference)
NIST Chemistry Reference: Benzaldehyde(100-52-7)
EPA Substance Registry System: Benzaldehyde(100-52-7)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes : Xn
Risk Statements : 22
Safety Statements : 24
RIDADR : UN 1990 9/PG 3
WGK Germany : 1
RTECS : CU4375000
F : 8
TSCA : Yes
HazardClass : 9
PackingGroup : III
Hazardous Substances Data: 100-52-7(Hazardous Substances Data)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H227 Combustible liquid Flammable liquids Category 4 Warning P210, P280, P370+P378, P403+P235,P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H320 Causes eye irritation Serious eye damage/eye irritation Category 2B Warning P264, P305+P351+P338,P337+P313
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H336 May cause drowsiness or dizziness Specific target organ toxicity,single exposure; Narcotic effects Category 3 Warning P261, P271, P304+P340, P312,P403+P233, P405, P501
H341 Suspected of causing genetic defects Germ cell mutagenicity Category 2 Warning P201,P202, P281, P308+P313, P405,P501
H371 May cause damage to organs Specific target organ toxicity, single exposure Category 2 Warning P260, P264, P270, P309+P311, P405,P501
H401 Toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 2 P273, P501
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P262 Do not get in eyes, on skin, or on clothing.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P271 Use only outdoors or in a well-ventilated area.
P272 Contaminated work clothing should not be allowed out of the workplace.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P370+P378 In case of fire: Use … for extinction.
P405 Store locked up.
P403+P233 Store in a well-ventilated place. Keep container tightly closed.
P501 Dispose of contents/container to..…

Benzaldehyde Chemical Properties,Usage,Production

description
Benzaldehyde is an organic compound, and is synthetized by the way that the hydrogen of benzene is substituted by aldehyde. It is the most simple, and also the most commonly used industrial aromatic aldehyde. It is a colorless liquid at room temperature and has a special almond odor. Benzaldehyde is a compound that aldehyde is directly linked to the phenyl group, because it has a similar bitter almond flavor. Benzaldehyde widely exists in plant, especially in the Rosaceae plants. It is mainly in the form of glycosides in plant stem bark, leaves or seeds, such as amygdalin, bitter almond, cherry, laurel, peach. Benzaldehyde is naturally in bitter almond oil, patchouli oil, hyacinth oil, cananga oil. The compound is also in the nutlets and nuts, and exists in the form of Amygdalin, which is combination of glycosides. The chemical properties of Benzaldehyde is similar to that of aliphatic aldehydes, but It is also different. Benzaldehyde cannot reduce fehling reagent. When the reducing fat is used to reduce the benzaldehyde, the main products are benzene methanol, four substituted for the ortho-glycol and two-phenyl ethylene glycol. In the presence of potassium cyanide, two molecules of benzaldehyde form benzoin by acceptance the hydrogen atom. The substitution reaction in aromatic nucleus of benzaldehyde is mainly the meta-position product. For example, the main product is the m-nitrobenzaldehyde , when benzaldehyde is nitrated.
Synthesis
Benzaldehyde can be prepared by a variety of ways. In industry, it is mainly contained by the way toluene in the catalyst (five of two vanadium, tungsten oxide and molybdenum oxide) carry on gas phase oxidation under the action of the air or oxygen. Or in the light, toluene is chlorinated into benzyl chloride, and then hydrolysis, oxidation, also be chlorinated into two chlorine methyl benzene chloride. The industry also has benzene as raw materials, preparation of reaction with carbon monoxide and hydrogen chloride, under the action of the pressure and aluminum chloride. In the laboratory, benzaldehyde is preparated by catalytic and reducing of benzoyl chloride. At present, the main preparation is the liquid chlorination or oxidation of toluene. The preparation methods have been eliminated, including Incomplete oxidation of benzene methanol, the alkali solution of benzoyl chloride, addition reaction of benzene and carbon monoxide.
reactions
Benzaldehyde can be oxidized to benzoic acid solid with white, unpleasant smell, and crystallized on the inner wall of the vessel. Benzyl alcohol can be gotten by hydrogenation of benzaldehyde, and also obtained by the self-oxidation-reduction of benzaldehyde in alcohol solution of potassium hydroxide in (product of potassium benzoate and benzyl alcohol). The reaction of benzaldehyde with anhydrous sodium acetate and acetic anhydride can produce cinnamic acid. The alcohol solution of potassium cyanide can be used for catalytic condensation of benzaldehyde, benzoin.
The disproportionation reaction of benzaldehyde in concentrated alkali solution (Cannizzaro reaction, Cannizarro reaction): a molecular aldehydes were reduced to the corresponding alcohol, another molecule of aldehyde was oxidized to carboxylic acid salt at the same time. The rate of this reaction is based on the substituted aromatic ring.
Toxicity
1.This product has a certain effect on the eyes and respiratory tract mucous membrane. Because of its low volatility, its stimulating effect is not enough to cause serious damage.
2.ADI 0~5mg/kg(FAO/WHO-1994)。
3.LD501.3g/kg(Rat, oral)。
4.GRAS(FDA,§182.60,2000)。
Emergency treatment
Skin contact: remove contaminated clothing, wash with the flow of water.
Eye contact: To lift the eyelids, wash with the flow of water or saline rinse. Medical treatment.
Inhalation: from the scene to the fresh air. If the breathing is difficult, you should be given oxygen. Medical treatment.
Food intake: drink enough warm water, reminders. should be fully discharged in closed operation.
Respiratory system protection: when the air concentration exceeds the standard, you must wear a self-absorption filter type gas mask (half mask). Emergency rescue or evacuation, should wear air breathing apparatus.
Eye protection: wear chemical safety goggles.
Body protection: wear anti poison penetration work clothes.
Hand protection: wear rubber gloves.
Other protection: smoking is prohibited in the workplace. Work completely, shower and change clothes. Take regular physical examination
Uses
1. Benzaldehyde is an important raw material for medicine, dyestuff, perfume and resin industry. It also can be used as solvent, plasticizer and low temperature lubricant. In essence, it is mainly used for the deployment of food flavor. A small amount of benzaldehyde is daily use in flavor and flavor of tobacco. In spite of being widely used as commercial food condiment and industrial solvents, the main use of benzyl alcohol is still used to synthesize a variety of other compounds from pharmaceuticals to plastic additives. Benzyl alcohol is an important intermediate product in the production of perfumes, spices, and some aniline dyes.
Mandelic acid was synthesized by benzaldehyde as the starting reagent: With the first hydrocyanic acid reacts with benzaldehyde, then mandelonitrile hydrolyzed to Racemic mandelic acid. Glacialist LaChepelle and Stillman reported Ice crystallization is inhibited by benzaldehyde and aldehydes ice in 1966, so as to prevent the thick frost formation (Depth Hoar). This process can prevent snowslide caused by the instability of the snow cover. However, this compound has not been used extensively, because of the destruction of vegetation and polluted water sources.
2. GB2760--1996 provides for the temporary use of edible spices. It is mainly used for the preparation of flavors, such as almond, cherry, peach, nuts, etc., the amount is up to 40%. As aromatizing agent canned cherry syrup, adding amount is sugar 3mL/kg.
3. Pharmaceutical, dyestuff, spice intermediates. For the production of oxygen based benzene formaldehyde, lauric acid, lauric aldehyde, malachite, benzyl benzoate, benzyl aniline and benzylidene acetone etc.. Used to tune the soap flavor, edible essence, etc.
4. As the head of the special aroma, it is used trace formula for fragrance, such as lilac, white, violet, jasmine, acacia, sunflower, sweet plum, orange flower, Tofu pudding etc.. Also it is used in soap. Also it can be used as edible spices for almond, coconut cream, berries, cherries, apricots, peaches, plums, walnuts, and vanilla bean, spicy flavor. Wine with flavors such as rum, brandy, etc.
5. Benzaldehyde is an intermediate of herbicide resistance, plant growth regulator, and anti-amine.
6. Used as a reagent for the determination of ozone, phenol, alkaloid and methylene. Used in the preparation of spices.
Chemical Properties
Colorless to light yellow liquid
Definition
ChEBI: An arenecarbaldehyde that consists of benzene bearing a single formyl substituent; the simplest aromatic aldehyde and parent of the class of benzaldehydes.
General Description
A clear colorless to yellow liquid with a bitter almond odor. Flash point near 145°F. More denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. The primary hazard is to the environment. Immediate steps should be taken to limit spread to the environment. Easily penetrates the soil to contaminate groundwater and nearby waterways. Used in flavoring and perfume making.
Air & Water Reactions
Oxidizes in air to form benzoic acid, which is moderately toxic by ingestion. Insoluble in water.
Reactivity Profile
A nontoxic, combustible liquid, reacts with oxidizing reagents. Benzaldehyde must be blanketed with an inert gas at all times since Benzaldehyde is oxidized readily by air to benzoic acid [Kirk-Othmer, 3rd ed., Vol. 3, 1978, p. 736]. In contact with strong acids or bases Benzaldehyde will undergo an exothermic condensation reaction [Sax, 9th ed., 1996, p. 327]. A violent reaction was observed on contact with peroxyacids (peroxyformic acid) [DiAns, J. et al., Ber., 1915, 48, p. 1136]. An explosion occurred when pyrrolidine, Benzaldehyde, and propionic acid were heated to form porphyrins.
Health Hazard
Inhalation of concentrated vapor may irritate eyes, nose and throat. Liquid is irritating to the eyes. Prolonged contact with the skin may cause irritation.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Benzaldehyde Preparation Products And Raw materials
Raw materials
CARBON MONOXIDE Benzyl chloride Benzyl alcohol Zinc oxide Toluene Chlorine Palladium Molybdenum trioxide Zinc phosphate Ozone Amygdalin trans-Cinnamaldehyde Aluminium chloride hexahydrate Cinnamon oil Sodium carbonate
Preparation Products
DL-Mandelic acid FLAVANONE 2-amino-5-chloro-diphenyl methanol 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one hydrochloride TRANS-2-PHENYL-1-CYCLOPROPANECARBOXYLIC ACID whitener WG for wool Benzenemethanol, ar-methyl-, acetate BENZYLHYDRAZINE DIHYDROCHLORIDE alpha-Hexylcinnamaldehyde Diaveridine Acid Blue 90 2,4,5-TRIPHENYLIMIDAZOLE L-Phenylglycine 3,4-Dichlorobenzylamine Magentagreencrystals Reactive Blue BRF Benzalacetone 5,5-Diphenylhydantoin 1-AMINO-4-METHYLPIPERAZINE DIHYDROCHLORIDE MONOHYDRATE 2-(Acetylamino)-3-phenyl-2-propenoic acid Methyl 1H-indole-2-carboxylate Acid Blue 9 2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide N,N'-Dibenzyl ethylenediamine diacetate Bis(dibenzylideneacetone)palladium ASTRAZON BRILLIANT RED 4G Reactive Blue 104 Nifedipine Epalrestat 4-Hydroxybenzylideneacetone 2-PHENYL-1.3-DIOXOLANE-4-METHANOL 3,5-DIPHENYLPYRAZOLE 2-((E)-2-Hydroxy-3-phenylacryloyl)benzoic acid ,97% (R)-(+)-N-Benzyl-1-phenylethylamine N,N'-BISBENZYLIDENEBENZIDINE Nitrotetrazolium blue chloride L-Arginine hydrochloride (E)-3-Benzylidene-3H-isochromene-1,4-dione ,97% 2,3,5-Triphenyltetrazolium chloride Tris(dibenzylideneacetone)dipalladium
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