BENZALDEHYDE (BENZALDEHT)
BENZALDEHYDE (BENZALDEHT)
CAS No.: 100-52-7
EC No.: 202-860-4
Synonyms:
BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BALD; NA 1989; FEMA 2127; NCI-C56133; Benaldehyde; Benzaldehyd; BENZALDEHYDE; Benzyaldehyde; BENZALADEHYDE; Benzaldehydee; Bitter almond; AKOS BBS-00003184; ARTIFICIAL ESSENTIAL OIL OF ALMOND; BALD; BENZALDEHYDE; BENZENECARBONAL; BENZOIC ALDEHYDE; BENZYL ALDEHYDE; BITTER ALMOND OIL; FEMA 2127; LABOTEST-BB LT00939687; OIL OF BITTER ALMOND; phenylmethanal; Almond artificial essential oil; almondartificialessentialoil; Artifical essential oil of almond; Artificial Almond Oil; Artificial bitter almond oil; artificialalmondoil; Benzaldehyde FFC; benzaldehydeffc; benzaldehyde; 100-52-7; Benzoic aldehyde; Phenylmethanal; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; Benzenecarbonal; Benzenecarboxaldehyde; Artificial almond oil; Benzenemethylal; Benzaldehyde FFC; Benzene carbaldehyde; Oil Of bitter almond; Benzene carboxaldehyde; Almond artificial essential oil; benzanoaldehyde; Benzylaldehyde; Benzoyl hydride; Caswell No. 076; Synthetic oil of bitter almond; Artificial essential oil of almond; NCI-C56133; benzaldehyd; Benzaldehyde (natural); Benzadehyde; Benzyaldehyde; FEMA No. 2127; Phenylformaldehyde; NSC 7917; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; Artificial bitter almond oil; UNII-TA269SD04T; Bitter almond oil, synthetic; Benzaldehyde [NF]; Ethereal oil of bitter almonds; Benzoic acid aldehyde; CCRIS 2376; HSDB 388; EINECS 202-860-4; UN1990; EPA Pesticide Chemical Code 008601; CHEMBL15972; AI3-09931; TA269SD04T; CHEBI:17169; Phenylmethanal benzenecarboxaldehyde; Benzaldehyde (NF); NCGC00091819-01; NCGC00091819-02; DSSTox_CID_134; DSSTox_RID_79432; DSSTox_GSID_39241; Benzaldhyde; BDBM50139371; CAS-100-52-7; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; Benzaldehyde [USAN]; benzaidehyde; benzaldehvde; benzaldehye; benzaldeyde; Bitter almond; phenyl-methanone; Benzene methylal; Aromatic aldehyde; Ben zoyl hydride; Benzoylwasserstoff; (phenyl)methanone; Benzaldehyde,(S); PhCHO; Benzaldehyde Natural; Natural Benzaldehyde; 10383-90-1; Benzene carboxaldehyde; 2vj1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; WLN: VHR; SCHEMBL573; bitter almond oil synthetic; EC 202-860-4; ACMC-1C91Y; ghl.PD_Mitscher_leg0.170; KSC176K2J; Benzaldehyde, AR, >=99%; Benzaldehyde, LR, >=99%; BIDD:ER0249; DTXSID8039241; BDBM60953; Benzaldehyde, analytical standard; CTK0H6524; KS-00000WWW; Artifical essential oil of almond; NSC7917; Ald3-H_000012; LS-27; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; ZINC895145; Benzaldehyde, >=98%, FG, FCC; NSC-7917; Ald3.1-H_000160; Ald3.1-H_000479; Ald3.1-H_000798; Tox21_113069; Tox21_113244; Tox21_200634; ANW-14310; MFCD00003299; s5574; STL194067; Benzaldehyde [UN1990] [Class 9]; Benzaldehyde, for synthesis, 95.0%; AKOS000119172; Benzaldehyde [UN1990] [Class 9]; CCG-266041; LS41490; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; MCULE-7744113682; NA 1989; Benzaldehyde, purum, >=98.0% (GC); Benzaldehyde, ReagentPlus(R), >=99%; NCGC00091819-03; NCGC00258188-01; PS-11959; SC-19173; Benzaldehyde, natural, >=98%, FCC, FG; NATURAL RSTD CASSIA OIL DIST FLAVOR; DB-023673; B2379; Benzaldehyde, SAJ special grade, >=98.0%; FT-0622622; FT-0622626; NS00008510; Benzaldehyde, Vetec(TM) reagent grade, 98%; 5044-EP2269979A1; 5044-EP2269990A1; 5044-EP2272491A1; 5044-EP2272827A1; 5044-EP2275404A1; 5044-EP2275411A2; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2275412A1; 5044-EP2277858A1; 5044-EP2277865A1; 5044-EP2277878A1; 5044-EP2281818A1; 5044-EP2284157A1; 5044-EP2286915A2; 5044-EP2287152A2; 5044-EP2287159A1; 5044-EP2289868A1; 5044-EP2292593A2; 5044-EP2295402A2; 5044-EP2295410A1; 5044-EP2295441A2; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2298767A1; 5044-EP2298776A1; 5044-EP2301534A1; 5044-EP2301536A1; 5044-EP2301538A1; 5044-EP2305625A1; 5044-EP2305629A1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2305662A1; 5044-EP2305679A1; 5044-EP2305687A1; 5044-EP2305769A2; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2305808A1; 5044-EP2308562A2; 5044-EP2311451A1; 5044-EP2311455A1; 5044-EP2311806A2; 5044-EP2311840A1; 5044-EP2314295A1; 5044-EP2314586A1; 5044-EP2314587A1; 5044-EP2314593A1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2316450A1; 5044-EP2316832A1; 5044-EP2316833A1; 5044-EP2371831A1; 5044-EP2374454A1; 5044-EP2374783A1; 5044-EP2377841A1; 5044-EP2380871A1; Benzaldehyde 1000 microg/mL in Dichloromethane; Benzaldehyde, puriss. p.a., >=99.0% (GC); C00193; C00261; D02314; 53585-EP2305651A1; 53585-EP2308854A1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 125826-EP2287158A1; 125826-EP2295422A2; A800226; Q372524; SR-01000944375; Benzaldehyde, purified by redistillation, >=99.5%; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; SR-01000944375-1; F1294-0144; Benzaldehyde, European Pharmacopoeia (EP) Reference Standard; Benzaldehyde, United States Pharmacopeia (USP) Reference Standard; Benzaldehyde, Pharmaceutical Secondary Standard; Certified Reference Material; 55279-75-9; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BALD; NA 1989; FEMA 2127; NCI-C56133; Benaldehyde; Benzaldehyd; BENZALDEHYDE; Benzyaldehyde; BENZALADEHYDE; Benzaldehydee; Bitter almond; AKOS BBS-00003184; ARTIFICIAL ESSENTIAL OIL OF ALMOND; BALD; BENZALDEHYDE; BENZENECARBONAL; BENZOIC ALDEHYDE; BENZYL ALDEHYDE; BITTER ALMOND OIL; FEMA 2127; LABOTEST-BB LT00939687; OIL OF BITTER ALMOND; phenylmethanal; Almond artificial essential oil; almondartificialessentialoil; Artifical essential oil of almond; Artificial Almond Oil; Artificial bitter almond oil; artificialalmondoil; Benzaldehyde FFC; benzaldehydeffc; benzaldehyde; 100-52-7; Benzoic aldehyde; Phenylmethanal; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; Benzenecarbonal; Benzenecarboxaldehyde; Artificial almond oil; Benzenemethylal; Benzaldehyde FFC; Benzene carbaldehyde; Oil Of bitter almond; Benzene carboxaldehyde; Almond artificial essential oil; benzanoaldehyde; Benzylaldehyde; Benzoyl hydride; Caswell No. 076; Synthetic oil of bitter almond; Artificial essential oil of almond; NCI-C56133; benzaldehyd; Benzaldehyde (natural); Benzadehyde; Benzyaldehyde; FEMA No. 2127; Phenylformaldehyde; NSC 7917; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; Artificial bitter almond oil; UNII-TA269SD04T; Bitter almond oil, synthetic; Benzaldehyde [NF]; Ethereal oil of bitter almonds; Benzoic acid aldehyde; CCRIS 2376; HSDB 388; EINECS 202-860-4; UN1990; EPA Pesticide Chemical Code 008601; CHEMBL15972; AI3-09931; TA269SD04T; CHEBI:17169; Phenylmethanal benzenecarboxaldehyde; Benzaldehyde (NF); NCGC00091819-01; NCGC00091819-02; DSSTox_CID_134; DSSTox_RID_79432; DSSTox_GSID_39241; Benzaldhyde; BDBM50139371; CAS-100-52-7; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; Benzaldehyde [USAN]; benzaidehyde; benzaldehvde; benzaldehye; benzaldeyde; Bitter almond; phenyl-methanone; Benzene methylal; Aromatic aldehyde; Ben zoyl hydride; Benzoylwasserstoff; (phenyl)methanone; Benzaldehyde,(S); PhCHO; Benzaldehyde Natural; Natural Benzaldehyde; 10383-90-1; Benzene carboxaldehyde; 2vj1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; WLN: VHR; SCHEMBL573; bitter almond oil synthetic; EC 202-860-4; ACMC-1C91Y; ghl.PD_Mitscher_leg0.170; KSC176K2J; Benzaldehyde, AR, >=99%; Benzaldehyde, LR, >=99%; BIDD:ER0249; DTXSID8039241; BDBM60953; Benzaldehyde, analytical standard; CTK0H6524; KS-00000WWW; Artifical essential oil of almond; NSC7917; Ald3-H_000012; LS-27; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; ZINC895145; Benzaldehyde, >=98%, FG, FCC; NSC-7917; Ald3.1-H_000160; Ald3.1-H_000479; Ald3.1-H_000798; Tox21_113069; Tox21_113244; Tox21_200634; ANW-14310; MFCD00003299; s5574; STL194067; Benzaldehyde [UN1990] [Class 9]; Benzaldehyde, for synthesis, 95.0%; AKOS000119172; Benzaldehyde [UN1990] [Class 9]; CCG-266041; LS41490; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; MCULE-7744113682; NA 1989; Benzaldehyde, purum, >=98.0% (GC); Benzaldehyde, ReagentPlus(R), >=99%; NCGC00091819-03; NCGC00258188-01; PS-11959; SC-19173; Benzaldehyde, natural, >=98%, FCC, FG; NATURAL RSTD CASSIA OIL DIST FLAVOR; DB-023673; B2379; Benzaldehyde, SAJ special grade, >=98.0%; FT-0622622; FT-0622626; NS00008510; Benzaldehyde, Vetec(TM) reagent grade, 98%; 5044-EP2269979A1; 5044-EP2269990A1; 5044-EP2272491A1; 5044-EP2272827A1; 5044-EP2275404A1; 5044-EP2275411A2; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2275412A1; 5044-EP2277858A1; 5044-EP2277865A1; 5044-EP2277878A1; 5044-EP2281818A1; 5044-EP2284157A1; 5044-EP2286915A2; 5044-EP2287152A2; 5044-EP2287159A1; 5044-EP2289868A1; 5044-EP2292593A2; 5044-EP2295402A2; 5044-EP2295410A1; 5044-EP2295441A2; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2298767A1; 5044-EP2298776A1; 5044-EP2301534A1; 5044-EP2301536A1; 5044-EP2301538A1; 5044-EP2305625A1; 5044-EP2305629A1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2305662A1; 5044-EP2305679A1; 5044-EP2305687A1; 5044-EP2305769A2; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2305808A1; 5044-EP2308562A2; 5044-EP2311451A1; 5044-EP2311455A1; 5044-EP2311806A2; 5044-EP2311840A1; 5044-EP2314295A1; 5044-EP2314586A1; 5044-EP2314587A1; 5044-EP2314593A1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 5044-EP2316450A1; 5044-EP2316832A1; 5044-EP2316833A1; 5044-EP2371831A1; 5044-EP2374454A1; 5044-EP2374783A1; 5044-EP2377841A1; 5044-EP2380871A1; Benzaldehyde 1000 microg/mL in Dichloromethane; Benzaldehyde, puriss. p.a., >=99.0% (GC); C00193; C00261; D02314; 53585-EP2305651A1; 53585-EP2308854A1; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; 125826-EP2287158A1; 125826-EP2295422A2; A800226; Q372524; SR-01000944375; Benzaldehyde, purified by redistillation, >=99.5%; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde; SR-01000944375-1; F1294-0144; Benzaldehyde, European Pharmacopoeia (EP) Reference Standard; Benzaldehyde, United States Pharmacopeia (USP) Reference Standard; Benzaldehyde, Pharmaceutical Secondary Standard; Certified Reference Material; 55279-75-9; BENZALDEHYDE; BENZALDEHT; Benzaldehit; Benzaldehyde
BENZALDEHYDE
Benzaldehyde
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Benzaldehyde
Skeletal (structural) formula
Ball-and-stick model
Names
Preferred IUPAC name
Benzaldehyde[1]
Systematic IUPAC name
Benzenecarbaldehyde
Other names
Benzenecarboxaldehyde
Phenylmethanal
Benzoic aldehyde
Identifiers
CAS Number
100-52-7 check
3D model (JSmol)
Interactive image
Interactive image
ChEBI
CHEBI:17169 check
ChEMBL
ChEMBL15972 check
ChemSpider
235 check
ECHA InfoCard 100.002.601 Edit this at Wikidata
EC Number
202-860-4
KEGG
D02314 check
PubChem CID
240
RTECS number
CU437500
UNII
TA269SD04T check
UN number 1990
CompTox Dashboard (EPA)
DTXSID8039241 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula C7H6O
Molar mass 106.124 g·mol−1
Appearance colorless liquid
strongly refractive
Odor almond-like
Density 1.044 g/mL, liquid
Melting point −57.12[2] °C (−70.82 °F; 216.03 K)
Boiling point 178.1 °C (352.6 °F; 451.2 K)
Solubility in water 6.95 g/L (25 °C)[3]
log P 1.64[4]
Magnetic susceptibility (χ) -60.78·10−6 cm3/mol
Refractive index (nD) 1.5456
Viscosity 1.321 cP (25 °C)
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298) −36.8 kJ/mol
Std enthalpy of
combustion (ΔcH⦵298) −3525.1 kJ/mol
Hazards
Safety data sheet J. T. Baker
GHS pictograms GHS07: Harmful
GHS Signal word Warning
GHS hazard statements H302
GHS precautionary statements P264, P270, P301+312, P330, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
220
Flash point 64 °C (147 °F; 337 K)
Autoignition
temperature 192 °C (378 °F; 465 K)
Explosive limits 1.4–8.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1300 mg/kg (rat, oral)
Related compounds
Related compounds Benzyl alcohol
Benzoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.
It is a colorless liquid with a characteristic almond-like odor. The primary component of bitter almond oil, benzaldehyde can be extracted from a number of other natural sources.[5] Synthetic benzaldehyde is the flavoring agent in imitation almond extract, which is used to flavor cakes and other baked goods.[6]
Contents
1 History
2 Production
3 Occurrence
4 Reactions
5 Uses
5.1 Niche uses
6 Safety
7 References
8 External links
History
Benzaldehyde was first extracted in 1803 by the French pharmacist Martrès. His experiments focused on elucidating the nature of amygdalin, the poisonous material found in bitter almonds, the fruit of Prunus dulcis.[7] Further work on the oil by Pierre Robiquet and Antoine Boutron-Charlard, two French chemists, produced benzaldehyde.[8] In 1832, Friedrich Wöhler and Justus von Liebig first synthesized benzaldehyde.[9]
Production
As of 1999, 7000 tonnes of synthetic and 100 tonnes of natural benzaldehyde were produced annually.[10] Liquid phase chlorination and oxidation of toluene are the main routes. Numerous other methods have been developed, such as the partial oxidation of benzyl alcohol, alkali hydrolysis of benzal chloride, and the carbonylation of benzene.[11]
A significant quantity of natural benzaldehyde is produced from cinnamaldehyde obtained from cassia oil by the retro-aldol reaction:[10] the cinnamaldehyde is heated in an aqueous/alcoholic solution between 90 °C and 150 °C with a base (most commonly sodium carbonate or bicarbonate) for 5 to 80 hours,[12] followed by distillation of the formed benzaldehyde. This reaction also yields acetaldehyde. The natural status of benzaldehyde obtained in this way is controversial.[10]
“Site-specific nuclear magnetic resonance spectroscopy”, which evaluates 1H/2H isotope ratios, has been used to differentiate between naturally occurring and synthetic benzaldehyde.[13]
Occurrence
Benzaldehyde and similar chemicals occur naturally in many foods. Most of the benzaldehyde that people eat is from natural plant foods, such as almonds.[14]
Almonds, apricots, apples, and cherry kernels contain significant amounts of amygdalin. This glycoside breaks up under enzyme catalysis into benzaldehyde, hydrogen cyanide and two equivalents of glucose.
Amygdalin
Amygdalin structure.svg
2 H
2O
HCN
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
benzaldehyde
Benzaldehyde.png
2 × glucose
2 × Alpha-D-glucose-2D-skeletal-hexagon.png
Benzaldehyde contributes to the scent of oyster mushrooms (Pleurotus ostreatus).[15]
Reactions
Benzaldehyde can be oxidized to benzoic acid; in fact “[B]enzaldehyde readily undergoes autoxidation to form benzoic acid on exposure to air at room temperature”[16] causing a common impurity in laboratory samples. Since the boiling point of benzoic acid is much higher than that of benzaldehyde, it may be purified by distillation. Benzyl alcohol can be formed from benzaldehyde by means of hydrogenation. Reaction of benzaldehyde with anhydrous sodium acetate and acetic anhydride yields cinnamic acid, while alcoholic potassium cyanide can be used to catalyze the condensation of benzaldehyde to benzoin. Benzaldehyde undergoes disproportionation upon treatment with concentrated alkali (Cannizzaro reaction): one molecule of the aldehyde is reduced to the benzyl alcohol and another molecule is simultaneously oxidized to benzoic acid.
Cannizzaro reaction
With diols, including many sugars, benzaldehyde condenses to form benzylidene acetals.
Uses
Benzaldehyde is commonly employed to confer almond flavor to foods and scented products. It is sometimes used in cosmetics products.[17]
In industrial settings, benzaldehyde is used chiefly as a precursor to other organic compounds, ranging from pharmaceuticals to plastic additives. The aniline dye malachite green is prepared from benzaldehyde and dimethylaniline. Benzaldehyde is also a precursor to certain acridine dyes. Via aldol condensations, benzaldehyde is converted into derivatives of cinnamaldehyde and styrene. The synthesis of mandelic acid starts with the addition of hydrocyanic acid to benzaldehyde:
mandelic acid synthesis
The resulting cyanohydrin is hydrolysed to mandelic acid. (The scheme above depicts only one of the two formed enantiomers).
Niche uses
Benzaldehyde is used as a bee repellent.[18] A small amount of benzaldehyde solution is placed on a fume board near the honeycombs. The bees then move away from the honey combs to avoid the fumes.[19] The beekeeper can then remove the honey frames from the bee hive with less risk to both bees and beekeeper.
Additionally, benzaldehyde is also used as a flavour chemical in JUUL e-cigarette pods, particularly the “Cool Mint”, “Cool Cucumber”, and “Fruit Medley” varieties. The concentration is relatively low, at ~1 μg/mL.[20]
Safety
As used in food, cosmetics, pharmaceuticals, and soap, benzaldehyde is “generally regarded as safe” (GRAS) by the US FDA[21] and FEMA.[14] This status was reaffirmed after a review in 2005.[14] It is accepted in the European Union as a flavoring agent.[17] Toxicology studies indicate that it is safe and non-carcinogenic in the concentrations used for foods and cosmetics,[17] and may even have anti-carcinogenic (anti-cancer) properties.[17]
For a 70 kg human, the lethal dose is estimated at 50 mL.[11] An acceptable daily intake of 15 mg/day has been identified for benzaldehyde by the United States Environmental Protection Agency.[22] Benzaldehyde does not accumulate in human tissues.[17] It is metabolized and then excreted in urine.[17]
Benzaldehyde Chemical Properties,Uses,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.
benzaldehyde structure
benzaldehyde structure
Chemical Properties
Benzaldehyde is the main, characteristic component of bitter almond oil. It occurs in many other essential oils and is a colorless liquid with a bitter almond odor. In the absence of inhibitors, benzaldehyde undergoes autoxidation to perbenzoic acid, which reacts with a second molecule of benzaldehyde to yield benzoic acid. Hydrogenation of benzaldehyde yields benzyl alcohol, and condensation with aliphatic aldehydes leads to additional fragrance substances or their unsaturated intermediates.Unsaturated araliphatic acids are obtained through the Perkin reaction, for example, the reaction with acetic anhydride to give cinnamic acid.
Benzaldehyde is used in aroma compositions for its bitter almond odor. It is the starting material for a large number of araliphatic fragrance and flavor materials.
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.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.
Production
Benzaldehyde can be prepared by a variety of ways.
Obtained from natural essential oils by fractionation.
Ozone oxidation and thiourea reduction reaction of natural cinnamon oil (containing cinnamaldehyde constituent 80% or more)
Catalytic oxidation of Toluene
Hydrolyze dichloromethane under alkaline conditions.
reactions
Benzaldehyde can be slowly oxidized to benzoic acid in air, so a small amount of hydroquinone is often added to prevent its oxidation.
There is no α-H atom in the benzaldehyde molecule. Disproportionation reaction(Cannizarro reaction) may occur under the action of concentrated alkali:
Heating benzaldehyde in the presence of catalyst of cyanide ion, it will occur bimolecular condensation:
Chemical Properties
Benzaldehyde is a colorless to yellow, oily liquid with an odor of bitter almonds. Benzaldehyde is commercially available in two grades: (i) pure benzaldehyde and (ii) and double-distilled benzaldehyde. The latter has applications in the pharmaceutical, perfume, and fl avor industries. Benzaldehyde may contain trace amounts of chlorine, water, benzoic acid, benzyl chloride, benzyl alcohol, and/or nitrobenzene. Benzaldehyde is ignited relatively easily on contact with hot surfaces. This has been attributed to the property of very low auto-ignition temperature. Benzaldehyde also undergoes autoxidation in air and is liable to self-heat. Benzaldehyde exists in nature, occurring in combined and uncombined forms in many plants. Benzaldehyde is also the main constituent of the essential oils obtained by pressing the kernels of peaches, cherries, apricots, and other fruits. Benzaldehyde is released into the environment in emissions from combustion processes, such as gasoline and diesel engines, incinerators, and wood burning. It is formed in the atmosphere through photochemical oxidation of toluene and other aromatic hydrocarbons. Benzaldehyde is corrosive to gray and ductile cast iron (10% solution), and all concentrations of lead. However, pure benzaldehyde is not corrosive to cast iron. Benzaldehyde does not attack most of the common metals, like stainless steels, aluminum, aluminum bronze, nickel and nickel-base alloys, bronze, naval brass, tantalum, titanium, and zirconium. On decomposition, benzaldehyde releases peroxybenzoic acid and benzoic acidBenzaldehyde is used in perfumes, soaps, foods, drinks, and other products; as a solvent for oils, resins, some cellulose ethers, cellulose acetate, and cellulose nitrate. The uses of benzaldehyde in industries are extensive. For instance, in the production of derivatives that are employed in the perfume and fl avor industries, like cinnamaldehyde, cinnamyl alcohol, cinnamic acid, benzylacetone, and benzyl benzoate, in the production of triphenylmethane dyes and the acridine dye, benzofl avin; as an intermediate in the pharmaceutical industry, for instance, to make chloramphenicol, ephedrin, and ampicillin, as an intermediate to make benzoin, benzylamine, benzyl alcohol, mandelic acid, and 4-phenyl-3-buten-2-one (benzylideneacetone), in photochemistry, as a corrosion inhibitor and dyeing auxiliary, in the electroplating industry, and in the production of agricultural chemicals
Occurrence
Present as cyanuric glucoside (amygdalin) in bitter almond, peach, apricot kernel and other Prunus species; amygdalin is also present in various parts of the following plants: Sambucus nigra, Chrysophyllum arlen, Anacyclus officinarnm, Anacyclus pedunculatus, Davallia brasiliensis, Lacuma deliciosa, Lacuma multiflora and others; free benzaldehyde has been reported found in several essential oils: hyacinth, citronella, orris, cinnamon, sassafras, labdanum and patchouli. Reported found in strawberry jam, leek (raw) (Allium porrum L.), crispbread, Camembert, Gruyere de Comte, provolone cheeses, black tea, salted and pickled plum, cooked trassi, Bantu beer, red sage (Texas sage) (S. coccinea Juss. Ex Murr.), arrack, scallop, hog plum (Spondias mombins L.), chekur (Alpinia sessilis Kon. = Kaemferia galanga) and other natural sources.
Uses
Benzaldehyde is used as an intermediatein the production of flavoring chemicals,such as cinnamaldehyde, cinnamalalcohol,and amyl- and hexylcinnamaldehyde for perfume,soap, and food flavor; synthetic penicillin,ampicillin, and ephedrine; and as araw material for the herbicide Avenge. Itoccurs in nature in the seeds of almonds,apricots, cherries, and peaches. It occurs intrace amounts in corn oil.
Uses
Manufacture of dyes, perfumery, cinnamic and mandelic acids, as solvent; in flavors.
Uses
Benzaldehyde is a flavoring agent which is liquid and colorless, and has an almond-like odor. it has a hot (burning) taste. it is oxidized to benzoic acid when exposed to air and deteriorates under light. it is miscible in volatile oils, fixed oils, ether, and alcohol; it is spar- ingly soluble in water. it is obtained by chemical synthesis and by natural occurrence in oils of bitter almond, peach, and apricot kernel. it is also termed benzoic aldehyde.
Definition
A yellow organic oil with a distinct almondlike odor. Benzenecarbaldehyde undergoes the reactions characteristic of aldehydes and may be synthesized in the laboratory by the usual methods of aldehyde synthesis. It is used as a food flavoring and in the manufacture of dyes and antibiotics, and can be readily manufactured by the chlorination of methylbenzene and the subsequent hydrolysis of (dichloromethyl) benzene: C6H5CH3 + Cl2 →C6H5CHCl2 C6H5CHCl2 + 2H2O →C6H5CH(OH)2+ 2HCl C6H5CH(OH)2 →C6H5CHO + H2O.
Preparation
Benzaldehyde is prepared by hydrolysis of benzal chloride, for example, in acidic media in the presence of a catalyst such as ferric chloride or in alkaline media with aqueous sodium carbonate. Part of the commercially available benzaldehyde originates from a technical process for phenol. In this process, benzaldehyde is a by-product in the oxidation, in air, of toluene to benzoic acid.
Reactions
Benzaldehyde reacts with many chemicals in a marked manner: (1) with ammonio-silver nitrate (“Tollen’s solution”) to form metallic silver, either as a black precipitate or as an adherent mirror film on glass (but does not reduce alkaline cupric solution, “Fehling’s solution”); (2) with rosaniline (fuchsine, magenta) that has been decolorized by sulfurous acid (“Schiff’s solution”), restoring the pink color of rosaniline; (3) with NaOH solution, yielding benzyl alcohol and sodium benzoate; (4) with NH4OH, yielding tribenzaldeamine (hydrobenzamide, (C6H5CH)3N2), white solid, mp 101 °C, (5) with aniline, yielding benzylideneaniline (“Schiff’s base” C6H5CH:NC6H5); (6) with sodium cyanide in alcohol, yielding benzoin C6H5·CHOHCOC6H5, white solid, mp 133 °C; (7) with hydroxylamine hydrochloride, yielding benzaldoximes C6H5CH:NOH, white solids, antioxime, mp 35 °C, syn-oxime, mp 130 °C; (8) with phenylhydrazine, yields benzaldehyde phenylhydrazone C6H5CH:NNHC6H5, pink solid, mp 156 °C; (9) with concentrated HNO3, yields metanitrobenzaldehyde NO2·C6H4CHO, white solid, mp 58 °C; (10) with concentrated H2SO4 yields metabenzaldehyde sulfonic acid C6H4CHO (SO3H)2, (11) with anhydrous sodium acetate and acetic anhydride at 180 °C, yielding sodium benzoate C6H5CHOONa (12) with sodium hydrogen sulfite, forming benzaldehyde sodium bisulfite C6H5CHOHSO3Na, a white solid, from which benzaldehyde is readily recoverable by treatment with sodium carbonate solution; (13) with acetaldehyde made slightly alkaline with NaOH, yielding cinnamic aldehyde C6H5CH:CHCHO, (14) with phosphorus pentachloride, yielding benzylidine chloride C6H5CHCl2.
Aroma threshold values
Detection: 100 ppb to 4.6 ppm; Recognition: 330 ppb to 4.1 ppm.
Taste threshold values
Taste characteristics at 50 ppm: sweet, oily, almond, cherry, nutty and woody
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 12, p. 403, 1964
The Journal of Organic Chemistry, 58, p. 4732, 1993 DOI: 10.1021/jo00069a043
Synthetic Communications, 16, p. 43, 1986 DOI: 10.1080/00397918608057686
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.
Hazard
Highly toxic.
Health Hazard
Benzaldehyde exhibited low to moderate toxicityin test animals, the poisoning effectdepending on dosage. Ingestion of 50–60 mLmay be fatal to humans. Oral intake of a largedose can cause tremor, gastrointestinal pain,and kidney damage. Animal experimentsindicated that ingestion of this compoundby guinea pigs caused tremor, bleeding fromsmall intestine, and an increase in urine volume;in rats, ingestion resulted in somnolenceand coma.
LD50 value, oral (guinea pigs): 1000 mg/kg
LD50 value, oral (rats): 1300 mg/kg
A 500-mg amount for a 24-hour periodresulted in moderate skin irritation in rabbits.Because of its low toxicity, high boilingpoint, and low vapor pressure, the healthhazard to humans from exposure to benzaldehydeis very low.
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.
Chemical Reactivity
Reactivity with Water: No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Pharmacology
Benzaldehyde significantly inhibited peptic activity in artificial gastric juice in vitro (20-45% inhibition) and in vivo to the extent of 87% in normal healthy persons and ulcer patients (Kleeberg, 1959). As a freshly prepared 1:500 solution, it exerted a marked antispasmodic effect, relaxing the tonus and inhibiting contractions of various isolated smooth muscles of dog, cat, rat, rabbit, mouse, guinea-pig, pig and frog and of a few human tissues. Injected into rabbits and other animals it produced a marked relaxation of the intestines and urinary bladder and marked vasodilation of the splanchnic vessel. Injection of 4 ml of a 5% solution iv into a cat caused a fall in blood pressure and slowing of respiration. In dogs, 1 ml injected iv or sc or 2 ml/kg given orally produced only a slight slowing of respiration. Injection of larger doses iv produced only a drop in blood pressure, slight slowing of respiration and inhibition of intestinal contractions, with vasodilation of the splanchnic vessel. In rabbits, iv injection of 20 ml of a 0-2% solution did not produce dangerous results. Large injected doses of benzaldehyde exert their mosjt important toxic effects on the medulla, with slowing or paralysis of respiration. In the intact animal, the heart is very little affected; but benzaldehyde acts as a muscular depressant on isolated frog heart (Macht, 1922). Treatment of isolated rat striated muscle for 1-5 min with 30 mM-benzaldehyde increased the rate of propagation of contractures and the rate of structural breakdown of injured striated muscle fibres. After more prolonged application (for 30 min), the rapid propagation of contracture continued but the structural breakdown was inhibited (Busing, 1972).
Benzaldehyde possessed definite local anaesthetic properties in the sciatic nerves of cats, dogs and frogs, in the eyes of rabbits and dogs (accompanied by irritation) and in the skin of frogs, but was considered unsuitable for practical use because of its rapid oxidation to benzoic acid (Macht, 1922).
In a study of the toxic effects of cherry laurel water on mice and on isolated rat intestine, benzaldehyde was found to aid in the detoxication of HCN by the formation of C6H5?CH(OH)?CN (Lanza & Conte, 1964).
Benzaldehyde did not act as a cross-linking (tanning) agent for corium and aorta, since in a 015 M solution it did not increase the observed in vitro hydrothermal shrinkage temperatures of goat skin and human, bovine and canine aortae (Milch, 1965).
The intestinal absorption-rate coefficients of benzaldehyde and related compounds were determined by perfusion of aqueous solutions through the small intestines of anaesthetized rats (Nogami, Hanano & Yamada, 1968).
No changes in gastric motor patterns, including gastric motility, were observed in rats after inhalation of “toxic levels” (not specified) of benzaldehyde from a liquid sample placed in a test chamber using recirculated air, or from a saturated paper applied to the trachea (Roth & Tansy, 1972).
Benzaldehyde in a concentration of 0-1 mmol/litre caused a 16% depression of the frequency of electric-organ discharge in the mormyrid electric fish Gnathonemus moori (Walsh & Schopp, 1966).
Safety Profile
Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. An allergen. Acts as a feeble local anesthetic. Local contact may cause contact dermatitis. Causes central nervous system depression in small doses and convulsions in larger doses. A skin irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible liquid. To fight fire, use water (may be used as a blanket), alcohol, foam, dry chemical. A strong reducing agent. Reacts violently with peroxyformic acid and other oxidizers. See also ALDEHYDES.
Chemical Synthesis
Natural benzaldehyde is obtained by extraction and subsequent fractional distillation from botanical sources; synthetically, from benzyl chloride and lime or by oxidation of toluene
Potential Exposure
In manufacture of perfumes, dyes, and cinnamic acid; as solvent; in flavors.
Metabolism
Benzaldehyde was among 300 volatile constituents detected in the urine of ten adults . It is commonly converted to hippuric acid in vivo. In the rabbit and dog, hippuric acid appears to be the only metabolite there being practically no formation of benzoyl glucuronide. The conversion of benzaldehyde to benzoic acid in the rabbit follows first-order reaction kinetics
storage
Benzaldehyde should be kept stored in a tightly closed container and protected against physical damage. Storage of the chemical substance outside or in a detached area is preferred, whereas inside storage should be in a standard flammable liquids storage room or cabinet. Benzaldehyde should be kept separated from oxidizing materials. Also, storage and use areas should be no smoking areas. Containers of this material may be hazardous when empty since they retain product residues (vapors, liquid); observe all warnings and precautions listed for the product
Shipping
UN1990 Benzaldehyde, Hazard class: 9; Labels: 9—Miscellaneous hazardous material.
Purification Methods
To diminish its rate of oxidation, benzaldehyde usually contains additives such as hydroquinone or catechol. It can be purified via its bisulfite addition compound but usually distillation (under nitrogen at reduced pressure) is sufficient. Prior to distillation it is washed with NaOH or 10% Na2CO3 (until no more CO2 is evolved), then with saturated Na2SO3 and H2O, followed by drying with CaSO4, MgSO4 or CaCl2. [Beilstein 7 IV 505.]
Incompatibilities
The substance reacts with air, forming explosive peroxides. Reacts violently with performic acid, oxidants, aluminum, iron, bases, and phenol, causing fire and explosion hazard. May self-ignite if absorbed in combustible material with large surface area, or otherwise dispersed over large areas. Reacts with rust, amines, alkalies, strong bases, reducing agents such as hydrideds and active metals.
Waste Disposal
Incineration; add combustible solvent and spray into incinerator with afterburner.
Precautions
Workers should be careful when using benzaldehyde because there is a risk of spontaneous combustion. It may ignite spontaneously if it is absorbed onto rags, cleaning cloths, clothing, sawdust, diatomaceous earth (kieselguhr), activated charcoal, or other materials with large surface areas in workplaces. Workers should avoid handling the chemical substance and should not cut, puncture, or weld on or near the container. Exposure of benzaldehyde to air, light, heat, hot surfaces such as hot pipes, sparks, open flames, and other ignition sources should be avoided. Workers should wear proper personal protective clothing and equipment
Benzaldehyde Preparation Products And Raw materials
BENZALDEHT
Benzaldehit
Gezinti ksmna atlaArama ksmna atla
Bu madde hiçbir kaynak içermemektedir. Lütfen güvenilir kaynaklar ekleyerek madde içeriinin gelitirilmesine yardmc olun. Kaynaksz içerik itiraz konusu olabilir ve kaldrlabilir.
Kaynak ara: “Benzaldehit” – haber · gazete · kitap · akademik · JSTOR (Eylül 2020) (Bu ablonun nasl ve ne zaman kaldrlmas gerektiini örenin)
Benzaldehit’in formülü
Benzaldehit, aromatik aldehitlerin en basit üyesi. C6H5CHO formülünde olup, renksiz, uçucu bir likittir. 179 °C’de kaynar, ac badem kokusundadr. Ac bademden ve sentetik olarak benzal klörünün hidrolizi ile elde edilir:
C6H5CHCl2 + H2O → C6H5CHO + 2HCl
Dier bir metot da toluenin uygun ortamda oksidasyonundan elde edilir.
Benzaldehit trifenil metan ve akridin boyalar üretiminde bir ara ürün olarak önemli bir materyaldir. Birçok organik bileiin sentezinde, parfümeri ve fotorafçlk kimyasnda kullanlr.
Taslak simgesi Organik kimya ile ilgili bu madde taslak seviyesindedir. Madde içeriini genileterek Vikipedi’ye katk salayabilirsiniz.
Benzaldehit
Gezintiye atlaArama yapmak için atla
Benzaldehit
skelet (yapsal) formül
Top ve sopa modeli
simler
Tercih edilen IUPAC ad
Benzaldehit [1]
Sistematik IUPAC ad
Benzenekarbaldehit
Dier isimler
Benzenkarboksaldehit
Fenilmetanal
Benzoik aldehit
Tanmlayclar
CAS numaras
100-52-7 çek
3B model (JSmol)
Etkileimli görüntü
Etkileimli görüntü
ChEBI
CHEBI: 17169 çek
ChEMBL
ChEMBL15972 kontrolü
ChemSpider
235 çek
ECHA InfoCard 100.002.601 Bunu Vikiveri’de düzenleyin
EC Numaras
202-860-4
KEGG
D02314 kontrol
PubChem Müteri Kimlii
240
RTECS numaras
CU437500
UNII
TA269SD04T kontrolü
BM numaras 1990
CompTox Kontrol Paneli (EPA)
DTXSID8039241 Bunu Vikiveri’de düzenleyin
InChI [gösteri]
SMILES [gösteri]
Özellikleri
Kimyasal formül C7H6O
Molar kütle 106,124 g · mol − 1
Görünüm renksiz sv
kuvvetli krlma
Badem gibi koku
Younluk 1.044 g / mL, sv
Erime noktas −57.12 [2] ° C (−70.82 ° F; 216.03 K)
Kaynama noktas 178.1 ° C (352.6 ° F; 451.2 K)
Suda çözünürlük 6,95 g / L (25 ° C) [3]
günlük P 1.64 [4]
Manyetik duyarllk (χ) -60,78 · 10−6 cm3 / mol
Krlma indisi (nD) 1.5456
Viskozite 1.321 cP (25 ° C)
Termokimya
Std entalpisi
oluumu (ΔfH⦵298) −36.8 kJ / mol
Std entalpisi
yanma (ΔcH⦵298) −3525.1 kJ / mol
Tehlikeler
Güvenlik veri sayfas J. T. Baker
GHS piktogramlar GHS07: Zararl
GHS Sinyal kelimesi Uyar
GHS tehlike beyanlar H302
GHS önlem beyanlar P264, P270, P301 + 312, P330, P501
NFPA 704 (ate elmas)
NFPA 704 dört renkli elmas
220
Parlama noktas 64 ° C (147 ° F; 337 K)
Kendiliinden tutuma
scaklk 192 ° C (378 ° F; 465 K)
Patlama snrlar% 1,4–8,5
Ölümcül doz veya konsantrasyon (LD, LC):
LD50 (medyan doz) 1300 mg / kg (sçan, oral)
Bantl bileikler
lgili bileikler Benzil alkol
Benzoik asit
Aksi belirtilmedii sürece, veriler standart hallerinde (25 ° C [77 ° F], 100 kPa) malzemeler için verilmitir.
kontrol et dorulayn (kontrol nedir?)
Bilgi kutusu referanslar
Benzaldehit (C6H5CHO), bir formil ikame edicisine sahip bir benzen halkasndan oluan organik bir bileiktir. En basit aromatik aldehittir ve endüstriyel olarak en kullanl olanlardan biridir.
Badem gibi karakteristik kokusu olan renksiz bir svdr. Ac badem yann birincil bileeni olan benzaldehit, baka birçok doal kaynaktan çkarlabilir. [5] Sentetik benzaldehit, kekleri ve dier unlu mamulleri tatlandrmak için kullanlan taklit badem özündeki aroma maddesidir. [6]
çindekiler
1 Geçmi
2 Üretim
3 Oluum
4 Reaksiyonlar
5 Kullanmlar
5.1 Ni kullanmlar
6 Güvenlik
7 Referanslar
8 D balantlar
Tarih
Benzaldehit ilk olarak 1803’te Fransz eczac Martrès tarafndan çkarld. Deneyleri, Prunus dulcis’in meyvesi olan ac bademlerde bulunan zehirli madde olan amigdalinin doasn aydnlatmaya odakland. [7] ki Fransz kimyager olan Pierre Robiquet ve Antoine Boutron-Charlard tarafndan ya üzerinde yaplan dier çalmalar benzaldehit üretti. [8] 1832’de Friedrich Wöhler ve Justus von Liebig ilk olarak benzaldehidi sentezlediler. [9]
Üretim
1999 yl itibar ile ylda 7000 ton sentetik ve 100 ton doal benzaldehit üretilmektedir. [10] Sv fazda klorlama ve toluenin oksidasyonu ana yollardr. Benzil alkolün ksmi oksidasyonu, benzal klorürün alkali hidrolizi ve benzenin karbonilasyonu gibi çok sayda baka yöntem gelitirilmitir. [11]
Retro-aldol reaksiyonu ile cassia yandan elde edilen sinnamaldehitten önemli miktarda doal benzaldehit üretilir: [10] sinnamaldehit sulu / alkollü bir çözelti içinde 90 ° C ile 150 ° C arasnda bir bazla (en yaygn olarak sodyum karbonat) stlr. veya bikarbonat) 5 ila 80 saat [12], ardndan oluan benzaldehit damtlr. Bu reaksiyon ayn zamanda asetaldehit verir. Bu ekilde elde edilen benzaldehitin doal durumu tartmaldr. [10]
1H / 2H izotop oranlarn deerlendiren “sahaya özgü nükleer manyetik rezonans spektroskopisi”, doal olarak oluan ve sentetik benzaldehidi ayrt etmek için kullanlmtr. [13]
Oluum
Benzaldehit ve benzeri kimyasallar birçok gdada doal olarak bulunur. nsanlarn yedii benzaldehitin çou badem gibi doal bitkisel gdalardandr. [14]
Badem, kays, elma ve kiraz çekirdekleri önemli miktarda amigdalin içerir. Bu glikozit, enzim katalizi altnda benzaldehit, hidrojen siyanür ve iki edeer glikoza parçalanr.
Amygdalin
Amygdalin yaps.svg
2 saat
2O
HCN
Sol üstten küçük alt tabakalar ve küçük ürünleri sa üste doru olan saa doru reaksiyon oku
benzaldehit
Benzaldehyde.png
2 × glikoz
2 × Alpha-D-glucose-2D-skeletal-hexagon.png
Benzaldehit, istiridye mantarnn (Pleurotus ostreatus) kokusuna katkda bulunur. [15]
Tepkiler
Benzaldehit, benzoik aside oksitlenebilir; aslnda “[B] enzaldehit, oda scaklnda havaya maruz kaldnda benzoik asit oluturmak için kolayca otoksidasyona urar” [16], laboratuvar örneklerinde yaygn bir kirlilie neden olur. Benzoik asidin kaynama noktas benzaldehitinkinden çok daha yüksek olduu için damtma ile saflatrlabilir. Benzil alkol, benzaldeh’den oluturulabilir
yde hidrojenasyon yoluyla. Benzaldehidin susuz sodyum asetat ve asetik anhidrit ile reaksiyonu sinnamik asit verirken, alkollü potasyum siyanür benzaldehidin benzoine younlamasn katalize etmek için kullanlabilir. Benzaldehit, konsantre alkali ile muameleye tabi tutulduktan sonra orantszlamaya urar (Cannizzaro reaksiyonu): aldehitin bir molekülü benzil alkole indirgenir ve baka bir molekül ayn anda benzoik aside oksitlenir.
Cannizzaro reaksiyonu
Pek çok eker içeren diollerle benzaldehit, benziliden asetalleri oluturmak için younlar.
Kullanmlar
Benzaldehit, genellikle yiyeceklere ve kokulu ürünlere badem aromas vermek için kullanlr. Bazen kozmetik ürünlerinde kullanlmaktadr. [17]
Endüstriyel ortamlarda, benzaldehit esas olarak farmasötiklerden plastik katk maddelerine kadar dier organik bileiklerin öncüsü olarak kullanlr. Anilin boya malakit yeili, benzaldehit ve dimetilanilinden hazrlanr. Benzaldehit ayrca belirli akridin boyalarnn öncüsüdür. Aldol younlamalar yoluyla benzaldehit, sinnamaldehit ve stiren türevlerine dönütürülür. Mandelik asit sentezi, hidrosiyanik asidin benzaldehite eklenmesiyle balar:
mandelik asit sentezi
Elde edilen siyanohidrin, mandelik aside hidrolize edilir. (Yukardaki ema, oluturulmu iki enantiyomerden yalnzca birini göstermektedir).
Ni kullanmlar
Benzaldehit, ar kovucu olarak kullanlr. [18] Peteklerin yaknndaki bir duman panosuna az miktarda benzaldehit çözeltisi yerletirilir. Arlar daha sonra duman önlemek için bal peteklerinden uzaklar. [19] Arc, hem arlar hem de arclar için daha az riskle bal çerçevelerini ar kovanndan çkarabilir.
Ayrca benzaldehit, JUUL e-sigara kapsüllerinde, özellikle “Souk Nane”, “Souk Salatalk” ve “Meyve Kark” çeitlerinde aroma kimyasal olarak da kullanlmaktadr. Konsantrasyon ~ 1 μg / mL’de nispeten düüktür. [20]
Emniyet
Gda, kozmetik, ilaç ve sabunda kullanld gibi, benzaldehit ABD FDA [21] ve FEMA [14] tarafndan “genellikle güvenli olarak kabul edilmektedir” (GRAS). Bu durum, 2005 ylnda yaplan bir incelemeden sonra yeniden teyit edildi. [14] Avrupa Birlii’nde tatlandrc olarak kabul edilmektedir. [17] Toksikoloji çalmalar, gdalar ve kozmetikler için kullanlan konsantrasyonlarda güvenli ve kanserojen olmadn [17] ve hatta anti-kanserojen (anti-kanser) özelliklere sahip olabileceini göstermektedir. [17]
70 kg’lk bir insan için, ölümcül dozun 50 mL olduu tahmin edilmektedir. [11] Amerika Birleik Devletleri Çevre Koruma Ajans tarafndan benzaldehit için kabul edilebilir bir günlük 15 mg / gün alm miktar tespit edilmitir. [22] Benzaldehit insan dokularnda birikmez. [17] Metabolize edilir ve daha sonra idrarla atlr. [17]
Benzaldehitin Kimyasal Özellikleri, Kullanm Alanlar, Üretimi
açklama
Benzaldehit organik bir bileiktir ve benzen hidrojeninin aldehit ile ikame edilmesi yoluyla sentezlenir. En basit ve ayn zamanda en yaygn kullanlan endüstriyel aromatik aldehittir. Oda scaklnda renksiz bir svdr ve özel badem kokusuna sahiptir. Benzaldehit, benzer ac badem aromasna sahip olduu için aldehitin dorudan fenil grubuna bal olduu bir bileiktir. Benzaldehit, bitkilerde, özellikle Rosaceae bitkilerinde yaygn olarak bulunur. Esas olarak amigdalin, ac badem, kiraz, defne, eftali gibi bitki sap kabuu, yapraklar veya tohumlarnda glikozitler formundadr. Benzaldehit, doal olarak ac badem ya, paçuli ya, sümbül ya, kananga ya içerisindedir. Bileik ayrca yemilerde ve kuruyemilerde bulunur ve glikozitlerin kombinasyonu olan Amygdalin formunda bulunur. Benzaldehit’in kimyasal özellikleri, alifatik aldehitlerinkine benzer, ancak ayn zamanda farkldr. Benzaldehit fehling reaktifini azaltamaz. ndirgeyici ya benzaldehitin indirgenmesi için kullanldnda, ana ürünler benzen metanoldür, dört tanesi orto-glikol ve iki-fenil etilen glikol yerine geçer. Potasyum siyanür varlnda, iki benzaldehit molekülü, hidrojen atomunu kabul ederek benzoin oluturur. Benzaldehitin aromatik çekirdeindeki ikame reaksiyonu esas olarak meta konum ürünüdür. Örnein, benzaldehit nitratlandnda ana ürün m-nitrobenzaldehittir.
benzaldehit yaps
benzaldehit yaps
Kimyasal özellikler
Benzaldehit, ac badem yann ana ve karakteristik bileenidir. Dier birçok uçucu yada bulunur ve ac badem kokusuna sahip renksiz bir svdr. nhibitörlerin yokluunda, benzaldehit, benzoik asit vermek üzere ikinci bir benzaldehit molekülü ile reaksiyona giren perbenzoik aside otoksidasyona urar. Benzaldehitin hidrojenlenmesi benzil alkol verir ve alifatik aldehitlerle younlama, ilave koku maddelerine veya bunlarn doymam ara maddelerine yol açar. Perkin reaksiyonu yoluyla doymam aralifatik asitler, örnein sinnamik asit vermek için asetik anhidrit ile reaksiyon yoluyla elde edilir.
Benzaldehit, ac badem kokusundan dolay aroma bileimlerinde kullanlr. Çok sayda aralifatik fragmann balangç materyalidir.
ance ve aroma malzemeleri.
Kullanmlar
1. Benzaldehit, ilaç, boya, parfüm ve reçine endüstrisi için önemli bir hammaddedir. Solvent, plastikletirici ve düük scaklkta yalayc olarak da kullanlabilir. Özünde, esas olarak gda aromasnn yaylmas için kullanlr. Tütünün tad ve aromasnda günlük olarak az miktarda benzaldehit kullanlr. Yaygn olarak ticari gda çenisi ve endüstriyel çözücüler olarak kullanlmasna ramen, benzil alkolün ana kullanm, farmasötiklerden plastik katk maddelerine kadar çeitli dier bileikleri sentezlemek için hala kullanlmaktadr. Benzil alkol, parfüm, baharat ve baz anilin boyalarnn üretiminde önemli bir ara üründür.
Mandelik asit, balangç reaktifi olarak benzaldehit tarafndan sentezlendi: lk hidrosiyanik asit, benzaldehit ile reaksiyona girdiinde, daha sonra mandelonitril, Rasemik mandelik aside hidrolize edildi. Buzulcu LaChepelle ve Stillman, buzun kristallemesinin 1966’da benzaldehit ve aldehit buzlar tarafndan engellendiini, böylece kaln don oluumunu (Derinlik Hoar) önlediini bildirdi. Bu ilem, kar örtüsünün dengesizliinin neden olduu kar kaymasn önleyebilir. Ancak, bitki örtüsünün tahrip olmas ve kirli su kaynaklarnn bozulmas nedeniyle bu bileik yaygn olarak kullanlmamtr.
2. Arlkl olarak badem, kiraz, eftali, kuruyemi vb. Tatlarn hazrlanmasnda kullanlr, miktar% 40’a kadardr. Aromatize edici ajan olarak konserve kiraz urubu ilave miktar eker 3mL / kg’dr.
3. laç, boyarmadde, baharat ara ürünleri. Oksijen bazl benzen formaldehit, laurik asit, laurik aldehit, malakit, benzil benzoat, benzil anilin ve benziliden aseton vb. Üretimi için. Sabun aromasn, yenilebilir özü vb. Ayarlamak için kullanlr.
4. Özel aromann ba ksm olarak leylak, beyaz, meneke, yasemin, akasya, ayçiçei, tatl erik, portakal çiçei, soya peyniri gibi kokular için iz formülü kullanlr. Ayrca sabun yapmnda kullanlr. Ayrca badem, hindistancevizi kremas, çilek, kiraz, kays, eftali, erik, ceviz ve vanilya fasulyesi, baharatl tad için yenilebilir baharat olarak kullanlabilir. Rom, brendi vb. Aromal araplar
5. Benzaldehit, herbisit direnci, bitki büyüme düzenleyicisi ve anti-aminin bir ara ürünüdür.
6. Ozon, fenol, alkaloid ve metilen tayini için reaktif olarak kullanlr. Baharatlarn hazrlanmasnda kullanlr.
Üretim
Benzaldehit, çeitli yollarla hazrlanabilir.
Doal uçucu yalardan fraksiyonlama ile elde edilir.
Doal tarçn yann ozon oksidasyonu ve tiyoüre indirgeme reaksiyonu (% 80 veya daha fazla tarçn bileeni içeren)
Toluenin katalitik oksidasyonu
Alkali koullar altnda diklorometan hidrolize edin.
tepkiler
Benzaldehit havada yava yava benzoik aside oksitlenebilir, bu nedenle oksidasyonunu önlemek için genellikle az miktarda hidrokinon eklenir.
Benzaldehit molekülünde α-H atomu yoktur. Orantszlk reaksiyonu (Cannizarro reaksiyonu) konsantre alkalinin etkisi altnda meydana gelebilir:
Benzaldehitin siyanür iyonu katalizörü varlnda stlmas, bimoleküler younlama meydana gelecektir:
Kimyasal özellikler
Benzaldehit, renksiz ila sar renkli, ac badem kokulu yal bir svdr. Benzaldehit ticari olarak iki snfta mevcuttur: (i) saf benzaldehit ve (ii) ve çift damtlm benzaldehit. kincisi, ilaç, parfüm ve tat endüstrilerinde uygulamalara sahiptir. Benzaldehit eser miktarda klor, su, benzoik asit, benzil klorür, benzil alkol ve / veya nitrobenzen içerebilir. Benzaldehit, scak yüzeylerle temas halinde nispeten kolay tutuur. Bu, çok düük kendiliinden tutuma scakl özelliine atfedilmitir. Benzaldehit ayrca havada otoksidasyona urar ve kendi kendine snmaya yatkndr. Benzaldehit doada bulunur ve birçok bitkide birleik ve birlememi formlarda bulunur. Benzaldehit ayrca eftali, kiraz, kays ve dier meyvelerin çekirdeklerinin preslenmesiyle elde edilen uçucu yalarn temel bileenidir. Benzaldehit, benzinli ve dizel motorlar, yakma frnlar ve odun yakma gibi yanma ilemlerinden kaynaklanan emisyonlarda çevreye salnr. Atmosferde toluen ve dier aromatik hidrokarbonlarn fotokimyasal oksidasyonu yoluyla oluur. Benzaldehit gri ve sfero döküm demiri (% 10 çözelti) ve tüm kurun konsantrasyonlarn andrr. Bununla birlikte, saf benzaldehit, dökme demiri andrmaz. Benzaldehit, paslanmaz çelikler, alüminyum, alüminyum bronz, nikel ve nikel bazl alamlar, bronz, deniz pirinci, tantal, titanyum ve zirkonyum gibi yaygn metallerin çouna saldrmaz. Ayrmada benzaldehit peroksibenzoik asit salglar ve benzoik asit Benzaldehit parfümlerde, sabunlarda, yiyeceklerde, içeceklerde ve dier ürünlerde kullanlr; yalar, reçineler, baz selüloz eterler, selüloz asetat ve selüloz nitrat için bir çözücü olarak. Benzaldehidin endüstrilerde kullanm çok genitir. Örnein, cinnamaldehyde, cinnamyl al gibi parfüm ve flavor endüstrilerinde kullanlan türevlerin üretiminde trifenilmetan boyalarn ve akridin boyann üretiminde, benzofl avin üretiminde kolol, sinnamik asit, benzilaseton ve benzil benzoat; Farmasötik endüstrisinde bir ara ürün olarak, örnein kloramfenikol, efedrin ve ampisilin yapmak için, benzoin, benzilamin, benzil alkol, mandelik asit ve 4-fenil-3-büten-2-on (benzilidenaseton) yapmak için bir ara ürün olarak , fotokimyada, korozyon önleyici ve boyama yardmc maddesi olarak, elektro kaplama endüstrisinde ve tarmsal kimyasallarn üretiminde
Oluum
Ac badem, eftali, kays çekirdei ve dier Prunus türlerinde siyanürik glukozit (amigdalin) olarak bulunur; amigdalin ayrca aadaki bitkilerin çeitli ksmlarnda mevcuttur: Sambucus nigra, Chrysophyllum arlen, Anacyclus officinarnm, Anacyclus pedunculatus, Davallia brasiliensis, Lacuma deliciosa, Lacuma multiflora ve dierleri; birkaç uçucu yada serbest benzaldehit bulunduu bildirilmitir: sümbül, sitronella, orris, tarçn, sassafras, labdanum ve paçuli. Çilek reçeli, prasa (çi) (Allium porrum L.), gevrek ekmek, Camembert, Gruyere de Comte, provolone peynirleri, siyah çay, tuzlanm ve salamura erik, pimi trassi, Bantu biras, krmz adaçay (Texas adaçay) (S . coccinea Juss. Ex Murr.), arak, tarak, domuz erii (Spondias mombins L.), chekur (Alpinia sessilis Kon. = Kaemferia galanga) ve dier doal kaynaklar.
Kullanmlar
Benzaldehit, parfüm, sabun ve gda aromas için sinnamaldehit, sinamalkol ve amil- ve heksilsinnamaldehit gibi tatlandrc kimyasallarn üretiminde bir ara ürün olarak kullanlr; sentetik penisilin, ampisilin ve efedrin; ve herbisit ntikam için araw malzemesi olarak. Doada badem, kays, kiraz ve eftali tohumlarnda bulunur. Msr yanda intrasik miktarlarda oluur.
Kullanmlar
Çözücü olarak boya, parfümeri, sinamik ve mandelik asit üretimi; tatlarda.
Kullanmlar
Benzaldehit, sv ve renksiz, badem benzeri bir kokuya sahip bir tatlandrcdr. scak (yakc) bir tad vardr. havaya maruz kaldnda benzoik aside oksitlenir ve k altnda bozulur. uçucu yalar, sabit yalar, eter ve alkolle karabilir; suda az çözünür. ac badem, eftali ve kays çekirdei yalarnda kimyasal sentez ve doal olarak meydana gelmesiyle elde edilir. ayn zamanda benzoik aldehit olarak da adlandrlr.
Tanm
Belirgin badem kokusuna sahip sar organik bir ya. Benzenekarbaldehit, aldehitlerin karakteristik reaksiyonlarna maruz kalr ve aldehit sentezinin olaan yöntemleriyle laboratuvarda sentezlenebilir. Bir gda aromas olarak ve boya ve antibiyotik üretiminde kullanlr ve metilbenzenin klorlanmas ve ardndan (diklorometil) benzenin hidrolizi ile kolayca üretilebilir: C6H5CH3 + Cl2 → C6H5CHCl2 C6H5CHCl2 + 2H2O → C6H5CH (OH) 2 + 2HCl C6H5CH (OH) 2 → C6H5CHO + H20.
Hazrlk
Benzaldehit, benzal klorürün, örnein demir klorür gibi bir katalizör varlnda asidik ortamda veya sulu sodyum karbonat ile alkali ortamda hidrolizi ile hazrlanr. Ticari olarak temin edilebilen benzaldehitin bir ksm, fenol için teknik bir ilemden kaynaklanr. Bu süreçte benzaldehit, toluenin havadaki benzoik aside oksidasyonunda bir yan üründür.
Tepkiler
Benzaldehit birçok kimyasal ile belirgin bir ekilde reaksiyona girer: (1) amonyo-gümü nitratla (“Tollen çözeltisi”) metalik gümü oluturmak için, ya siyah bir çökelti olarak veya cam üzerinde yapkan bir ayna filmi olarak (ancak alkali bakr çözeltisini azaltmaz) , “Fehling’in çözümü”); (2) kükürtlü asit (“Schiff solüsyonu”) ile rengi giderilmi, rosanilinin pembe rengini geri kazandran rosanilin (fuksin, macenta) ile; (3) NaOH çözeltisi ile benzil alkol ve sodyum benzoat verir; (4) NH4OH ile, tribenzaldeamin (hidrobenzamid, (C6H5CH) 3N2), beyaz kat, en 101 ° C, (5) anilin ile, benzilidenanilin (“Schiff baz” C6H5CH: NC6H5) verir; (6) alkol içinde sodyum siyanür ile, sonuçta benzoin C6H5 · CHOHCOC6H5, beyaz kat, en 133 ° C; (7) hidroksilamin hidroklorür ile, benzaldoksimes C6H5CH: NOH, beyaz katlar, antioksim, en 35 ° C, syn-oxime, mp 130 ° C; (8) fenilhidrazin ile benzaldehit fenilhidrazon verir C6H5CH: NNHC6H5, pembe kat, erime noktas 156 ° C; (9) konsantre HNO3 ile metanitrobenzaldehit NO2-C6H4CHO verir, beyaz kat, erime noktas 58 ° C; (10) konsantre H2SO4 ile 180 ° C’de susuz sodyum asetat ve asetik anhidrit ile metabenzaldehit sülfonik asit C6H4CHO (SO3H) 2, (11) verir, sodyum hidrojen sülfit ile sodyum benzoat C6H5CHOONa (12) verir, benzaldehit sodyum bisülfit C6H5CHO benzaldehitin sodyum karbonat çözeltisi ile ilemden geçirilerek kolayca geri kazanlabildii beyaz kat; (13) asetaldehit ile NaOH ile hafifçe alkali hale getirilerek, fosfor pentaklorür ile sinamik aldehit C6H5CH: CHCHO, (14), benzilidin klorür C6H5CHCl2 verdi.
Aroma eik deerleri
Alglama: 100 ppb ila 4,6 ppm; Tanma: 330 ppb ila 4,1 ppm.
Taste eik deerleri
50 ppm’de tat özellikleri: tatl, yal, badem, kiraz, cevizimsi ve odunsu
Sentez Referanslar
Kimya ve laç Bülteni, 12, s. 403, 1964
Organik Kimya Dergisi, 58, s. 4732, 1993 DOI: 10.1021 / jo00069a043
Sentetik letiim, 16, s. 43, 1986 DOI: 10.1080 / 00397918608057686
Genel açklama
Ac badem kokusu ile berrak renksiz ila sar bir sv. 145 ° F’ye yakn parlama noktas. Sudan daha youn ve suda çözünmez. Dolaysyla suda batar. Buharlar havadan ardr. Birincil tehlike çevreye yöneliktir. Çevreye yaylmay snrlandrmak için acil admlar atlmaldr. Yeralt sularn ve yakndaki su yollarn kirletmek için topraa kolayca nüfuz eder. Aroma ve parfüm yapmnda kullanlr.
Hava ve Su Reaksiyonlar
Yutulduunda orta derecede toksik olan benzoik asit oluturmak için havada oksitlenir. Suda çözünmez.
Reaktivite Profili
Zehirli olmayan, yanc bir sv, oksitleyici reaktiflerle reaksiyona girer. Benzaldehit, havayla kolayca benzoik aside oksitlendii için, benzaldehit her zaman bir inert gazla örtülmelidir [Kirk-Othmer, 3. bask, Cilt. 3, 1978, s. 736]. Güçlü asitler veya bazlarla temas halinde Benzaldehit, bir ekzotermik younlama reaksiyonuna girecektir [Sax, 9th ed., 1996, s. 327]. Peroksiasitler (peroksiformik asit) ile temas üzerine iddetli bir reaksiyon gözlemlendi [DiAns, J. ve dierleri, Ber., 1915, 48, s. 1136]. Pirolidin, Benzaldehit ve propiyonik asit porfirin oluturmak için stldnda bir patlama meydana geldi.
Tehlike
Oldukça zehirlidir.
Salk tehlikesi
Benzaldehit, test hayvanlarnda düük ila orta derecede toksisite sergilemitir, zehirlenme etkisi doza baldr. 50-60 mL yutulmas insanlar için ölümcül olabilir. Azdan büyük doz alm titreme, gastrointestinal ar ve böbrek hasarna neden olabilir. Hayvan deneyleri, bu bileiin kobaylar tarafndan yutulmasnn titremeye, küçük barsaktan kanamaya ve idrar hacminde arta neden olduunu; sçanlarda yutmann uyku hali ve komaya neden olduunu gösterdi.
LD50 deeri, azdan (kobaylar): 1000 mg / kg
LD50 deeri, azdan (sçanlar): 1300 mg / kg
24 saatlik bir süre için 500 mg’lk bir miktar, tavanlarda orta derecede deri tahriine neden olmutur. Düük toksisitesi, yüksek kaynama noktas ve düük buhar basnc nedeniyle, benzaldehide maruziyetten insanlar için salk tehlikesi çok düüktür.
Yangn tehlikesi
SON DERECE YANICIDIR: Is, kvlcm veya alevle kolayca tutuur. Buharlar hava ile patlayc karmlar oluturabilir. Buharlar ateleme kaynana gidebilir ve parlayabilir. Buharlarn çou havadan ardr. Zemin boyunca yaylacaklar ve alçak veya snrl alanlarda (kanalizasyonlar, bodrum katlar, tanklar) toplanacaklar. çeride, darda veya kanalizasyonda buhar patlama tehlikesi. Kanalizasyona aktlmas yangn veya patlama tehlikesi yaratabilir. Kaplar stldnda patlayabilir. Çou sv sudan daha hafiftir.
Kimyasal Reaktivite
Su ile Reaktivite: Reaksiyon yok; Ortak Malzemelerle Reaktivite: Reaksiyon yok; Tama Srasnda Kararllk: Kararl; Asitler ve Kostikler için Nötrletirici Ajanlar: lgili deil; Polimerizasyon: lgili deil; Polimerizasyon nhibitörü: lgili deil.
Farmakoloji
Benzaldehit, yapay mide suyundaki peptik aktiviteyi in vitro (% 20-45 inhibisyon) ve normal salkl kiilerde ve ülser hastalarnda in vivo% 87’ye kadar önemli ölçüde inhibe etti (Kleeberg, 1959). Taze hazrlanm 1: 500’lük bir çözelti olarak, köpek, kedi, sçan, tavan, fare, kobay, domuz ve kurbaa ile birkaç insann çeitli izole düz kaslarnn tonusunu geveterek ve kaslmalarn engelleyerek belirgin bir antispazmodik etki gösterdi. Dokular. Tavanlara ve dier hayvanlara enjekte edildiinde, barsaklarda ve idrar kesesinde belirgin bir geveme ve splanknik damarda belirgin bir vazodilatasyon salad. Bir kediye 4 ml% 5’lik solüsyon iv enjekte edilmesi kan basncnda düüe ve solunumun yavalamasna neden oldu. Köpeklerde, 1 ml iv veya sc veya oral yoldan verilen 2 ml / kg enjekte sadece hafif bir solunum yavalamas oluturdu. Daha büyük doz iv enjeksiyonu, splanknik damarn vazodilatasyonu ile kan basncnda sadece bir düü, solunumda hafif bir yavalama ve barsak kaslmalarnn inhibisyonuna neden oldu. Tavanlarda, 20 ml% 0-2 solüsyonun iv enjeksiyonu tehlikeli sonuçlar vermedi. Enjekte edilen büyük benzaldehit dozlar, solunumun yavalamas veya felce uramas ile medulla üzerinde çok önemli toksik etkiler gösterir. Salam hayvanda kalp çok az etkilenir; ancak benzaldehit izole kurbaa kalbi üzerinde kas depresan olarak görev yapar (Macht, 1922). zole edilmi sçan çizgili kasnn 1-5 dakika süreyle 30 mM-benzaldehit ile tedavisi, kontraktürlerin yaylma orann ve yaral çizgili kas liflerinin yapsal bozulma orann arttrd. Daha uzun süreli uygulamadan sonra (30 dakika boyunca), kontraktür hzl yaylmaya devam etti, ancak yapsal bozulma engellendi (Busing, 1972).
Benzaldehit, kedilerin, köpeklerin ve kurbaalarn siyatik sinirlerinde, tavanlarn ve köpeklerin gözlerinde (tahri ile birlikte) ve kurbaalarn derisinde kesin lokal anestezik özelliklere sahipti, ancak uygun olmad kabul edildi.
veya benzoik aside hzl oksidasyonu nedeniyle pratik kullanm (Macht, 1922).
Kiraz defne suyunun fareler ve izole edilmi sçan barsa üzerindeki toksik etkileri üzerine yaplan bir çalmada, benzaldehitin, C6H5? CH (OH)? CN oluumu yoluyla HCN’nin detoksikasyonuna yardmc olduu bulunmutur (Lanza & Conte, 1964).
Benzaldehit, koryum ve aort için çapraz balama (tabaklama) ajan olarak ilev görmedi, çünkü 015 M’lik bir çözeltide, keçi derisi ve insan, sr ve köpek aortalarnn gözlenen in vitro hidrotermal büzülme scaklklarn artrmad (Milch, 1965) .
Benzaldehit ve ilgili bileiklerin barsakta absorpsiyon hz katsaylar, anestezi uygulanm sçanlarn ince barsaklarndan sulu çözeltilerin perfüzyonuyla belirlendi (Nogami, Hanano & Yamada, 1968).
Sçanlarda, yeniden sirküle edilmi hava kullanlarak bir test odasna yerletirilen sv bir numuneden veya trakeaya uygulanan doymu bir kattan benzaldehidin “toksik seviyelerinin” (belirtilmemi) solunmasndan sonra, mide hareketlilii dahil olmak üzere mide motor modellerinde hiçbir deiiklik gözlenmedi. (Roth ve Tansy, 1972).
0-1 mmol / litre konsantrasyondaki benzaldehit, mormyrid elektrikli balk Gnathonemus moori’de elektrik organ dearj sklnda% 16’lk bir düüe neden oldu (Walsh & Schopp, 1966).
Güvenlik profili
Yutma ve intraperitoneal yollarla zehirlenme. Deri alt yolla orta derecede toksiktir. Bir alerjen. Zayf bir lokal anestezik görevi görür. Yerel temas, kontakt dermatite neden olabilir. Küçük dozlarda merkezi sinir sistemi depresyonuna ve daha yüksek dozlarda konvülsiyonlara neden olur. Cildi tahri eder. Deneysel tümörijenik verilerle üpheli kanserojen. Mutasyon verileri bildirildi. Yanc sv. Yangnla mücadele etmek için su (battaniye olarak kullanlabilir), alkol, köpük, kuru kimyasal kullann. Güçlü bir indirgeme ajan. Peroksiformik asit ve dier oksitleyicilerle iddetli reaksiyona girer. Ayrca bkz. ALDEHDLER.
Kimyasal Sentez
Doal benzaldehit, botanik kaynaklardan ekstraksiyon ve ardndan fraksiyonel damtma yoluyla elde edilir; sentetik olarak, benzil klorür ve kireçten veya toluenin oksidasyonu ile
Potansiyel maruziyet
Parfüm, boya ve sinamik asit üretiminde; çözücü olarak; tatlarda.
Metabolizma
Benzaldehit, on yetikinin idrarnda tespit edilen 300 uçucu bileen arasndayd. Genellikle in vivo olarak hippurik aside dönütürülür. Tavan ve köpekte, hippurik asit, pratikte hiç benzoil glukuronid oluumu olmayan tek metabolit gibi görünmektedir. Tavanda benzaldehidin benzoik aside dönüümü birinci dereceden reaksiyon kinetiini izler
depolama
Benzaldehit, skca kapatlm bir kapta saklanmal ve fiziksel hasara kar korunmaldr. Kimyasal maddenin darda veya müstakil bir alanda depolanmas tercih edilirken, iç depolama standart bir yanc svlar depolama odas veya dolabnda olmaldr. Benzaldehit, oksitleyici maddelerden ayr tutulmaldr. Ayrca depolama ve kullanm alanlarnda sigara içilmemelidir. Bu malzemenin kaplar, ürün kalntlarn (buharlar, sv) tuttuklar için bo olduklarnda tehlikeli olabilir; ürün için listelenen tüm uyarlara ve önlemlere uyun
Nakliye
UN1990 Benzaldehyde, Tehlike snf: 9; Etiketler: 9 — Muhtelif tehlikeli maddeler.
Saflatrma Yöntemleri
Oksidasyon orann azaltmak için benzaldehit genellikle hidrokinon veya katekol gibi katk maddeleri içerir. Bisülfit ilaveli bileii ile saflatrlabilir, ancak genellikle damtma (düük basnçta nitrojen altnda) yeterlidir. Damtmadan önce NaOH veya% 10 Na2CO3 (CO2 aça çkmayana kadar), ardndan doymu Na2SO3 ve H2O ile ykanr ve ardndan CaSO4, MgSO4 veya CaCl2 ile kurutulur. [Beilstein 7 IV 505.]
Uyumsuzluklar
Bu madde hava ile reaksiyona girerek patlayc peroksitler oluturur. Performik asit, oksidanlar, alüminyum, demir, bazlar ve fenol ile iddetli reaksiyonu yangna ve patlamaya neden olur. Geni yüzey alanna sahip yanc malzemede emilirse veya baka ekilde geni alanlara yaylrsa kendiliinden tutuabilir. Pas, aminler, alkaliler, güçlü bazlar, hidridler gibi indirgeyici maddeler ve aktif metallerle reaksiyona girer.
Atk Bertaraf
Yakma; yanc solvent ekleyin ve art yakc ile yakma frnna püskürtün.
Önlemler
çiler benzaldehit kullanrken dikkatli olmaldr çünkü kendiliinden yanma riski vardr. yerlerinde paçavra, temizlik bezleri, giysiler, tala, kizelgur (kizelgur), aktif kömür veya geni yüzeyli dier malzemeler üzerine emilirse kendiliinden tutuabilir. çiler kimyasal maddeyi kullanmaktan kaçnmal ve kap üzerinde veya yaknnda kesmemeli, delmemeli veya kaynak yapmamaldr. Benzaldehitin havaya, a, scaa, scak borular gibi scak yüzeylere, kvlcmlara, açk alevlere ve dier tututurucu kaynaklara maruz kalmasndan kaçnlmaldr. çiler uygun kiisel koruyucu kyafet ve ekipman giymelidir
Benzaldehit Hazrlama Ürünleri ve Hammaddeler