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Benzaldehyde

 

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Benzaldehyde



 
 
Benzaldehyde (C6H5CHO) is a chemical compound consisting of a benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 ring with an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds. At room temperature it is a colorless liquid with a characteristic and pleasant almond
Almond

The Almond is a species of tree of the genus Prunus, belonging to the subfamily Prunoideae of the family Rosaceae and native to the Middle East....
-like odor
Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
: benzaldehyde is an important component of the scent of almonds, hence its typical odor.






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Encyclopedia


Benzaldehyde (C6H5CHO) is a chemical compound consisting of a benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 ring with an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds. At room temperature it is a colorless liquid with a characteristic and pleasant almond
Almond

The Almond is a species of tree of the genus Prunus, belonging to the subfamily Prunoideae of the family Rosaceae and native to the Middle East....
-like odor
Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
: benzaldehyde is an important component of the scent of almonds, hence its typical odor. It is the primary component of bitter almond oil extract, and can be extracted from a number of other natural sources in which it occurs, such as apricot
Apricot

The Apricot is a species of Prunus, classified with the plum in the subgenus Prunus. The native range is somewhat uncertain due to its extensive prehistoric cultivation, but most likely in northern and western China and Central Asia, possibly also Korea and Japan....
, cherry
Cherry

The word cherry refers to a fleshy fruit that contains a single stony seed. The cherry belongs to the family Rosaceae, genus Prunus, along with almonds, peaches, plums, apricots and bird cherry ....
, and laurel
Bay Laurel

The Bay Laurel , also known as True Laurel, Sweet Bay, Grecian Laurel, Laurel, or Bay Tree, is an aromatic evergreen tree or large shrub reaching 10?18 m tall, native to the Mediterranean region....
 leaves
Leaf

In botany, a leaf is an above-ground plant Organ specialized for photosynthesis. For this purpose, a leaf is typically flat and thin, to expose the cells containing chloroplast to light over a broad area, and to allow light to penetrate fully into the tissues....
, peach
Peach

The peach is known as a species of Prunus native to China that bears an edible juicy fruit also called a peach. It is a deciduous tree growing to 5?10 m tall, belonging to the subfamily Prunoideae of the family Rosaceae....
 seed
Seed

A seed is a small Plant embryogenesis plant enclosed in a covering called the seed coat, usually with some Food storage. It is the product of the ripened ovule of gymnosperm and angiosperm plants which occurs after fertilization and some growth within the mother plant....
s and, in a glycoside
Glycoside

In chemistry, glycosides are certain molecules in which a sugar part is bound to some other part. Glycosides play numerous important roles in living organisms....
 combined form (amygdalin
Amygdalin

Amygdalin , C20H27NO11, is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet...
), in certain nut
Nut (fruit)

Nut is a general term for the large, dry, oily seed or fruit of some plant. While a wide variety of dried seeds and fruits are called nuts, only a certain number of them are considered by biologists to be true nuts....
s and kernel
Seed

A seed is a small Plant embryogenesis plant enclosed in a covering called the seed coat, usually with some Food storage. It is the product of the ripened ovule of gymnosperm and angiosperm plants which occurs after fertilization and some growth within the mother plant....
s. Currently benzaldehyde is primarily made from toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
 by a number of different processes.

Production


Benzaldehyde can be obtained by many processes. Currently liquid phase chlorination
Halogenation

Halogenation is a chemical reaction that incorporates a halogen atom into a molecule. More specific descriptions exist that specify the type of halogen: fluorination, chlorination, bromination, and iodination....
 or oxidation
Redox

Redox describes all chemical reactions in which atoms have their oxidation number changed.This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide or the reduction of carbon by hydrogen to yield methane , or it can be a complex process such as the oxidation of sugar in the human body through a ser...
 of toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
 are among the most used processes. There are also a number of discontinued applications such as partial oxidation of benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
, alkali
Alkali

In chemistry, an alkali is a Base , Ionic compound salt of an alkali metal or alkaline earth metal Chemical element. Alkalis are best known for being Base s that dissolve in water....
 treating of benzal chloride
Benzal chloride

Benzal chloride is an organic compound with the chemical formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis....
 and reaction between benzene and carbon monoxide
Carbon monoxide

Carbon monoxide, with the chemical formula CO, is a colorless and odorless, tasteless, yet highly toxic gas. Its molecules consist of one carbon atom covalent bond to one oxygen atom....
.

Reactions


On oxidation, benzaldehyde is converted into the odorless benzoic acid
Benzoic acid

Benzoic acid, C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid....
. Benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
 can be formed from benzaldehyde by means of hydrogenation
Hydrogenation

Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
 or by treating the compound with alcoholic potassium hydroxide
Potassium hydroxide

Potassium hydroxide is the inorganic compound with the formula potassiumhydroxide. Along with sodium hydroxide, this colourless solid is a prototypical "strong base"....
 thus undergoing a simultaneous oxidation and reduction
Redox

Redox describes all chemical reactions in which atoms have their oxidation number changed.This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide or the reduction of carbon by hydrogen to yield methane , or it can be a complex process such as the oxidation of sugar in the human body through a ser...
 which result in the production of potassium benzoate
Potassium benzoate

Potassium benzoate , the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacterium. It works best in low-pH products, below 4.5, where it exists as benzoic acid....
 and benzyl alcohol. Reaction of benzaldehyde with anhydrous sodium acetate
Sodium acetate

Sodium acetate, is the sodium Salt of acetic acid. It is an inexpensive chemical produced in industrial quantities for a wide range of uses....
 and acetic anhydride
Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
 yields cinnamic acid
Cinnamic acid

Cinnamic acid has the formula C6H5CHCHCOOH and is a white crystalline acid, which is slightly soluble in water. It has a melting point of 133?C and a boiling point of 300?C....
, while alcoholic potassium cyanide
Potassium cyanide

Potassium cyanide is an inorganic compound with the chemical formula KCN. This colorless crystalline compound, similar in appearance to sugar, is highly soluble in water....
 can be used to catalyze
Catalysis

Catalysis is the process in which the reaction rate of a chemical reaction is either increased or decreased by means of a chemical substance known as a catalyst....
 the condensation of benzaldehyde to benzoin
Benzoin

Benzoin or 2-Hydroxy-2-phenylacetophenone or 2-Hydroxy-1,2-Diphenylethanone or desyl alcohol or bitter almond oil camphor is an organic compound consisting of an ethylene bridge flanked by phenyl groups and with a hydroxyl and a ketone functional group....
.

Benzaldehyd Chemical Annizzaro
Benzaldehyde can also undergo disproportionation
Disproportionation

Disproportionation or dismutation is used to describe two particular types of chemical reaction:* A chemical reaction of the type: 2A ? A' + A" where A, A' and A" are different chemical species....
 in concentrated alkali (Cannizzaro's reaction
Cannizzaro reaction

The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base -induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position....
): one molecule of the aldehyde is reduced to the corresponding alcohol and another molecule is simultaneously oxidized to the salt of a carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
. The speed of this reaction depends on the substituents present in the aromatic ring.

Uses


While it is commonly employed as a commercial food flavor
Flavor

Flavor or flavour is the sensory impression of a food or other chemical substance, and is determined mainly by the chemical senses of taste and olfaction....
ant (almond
Almond

The Almond is a species of tree of the genus Prunus, belonging to the subfamily Prunoideae of the family Rosaceae and native to the Middle East....
 flavor) or industrial solvent
Solvent

A solvent is a liquid or gas that dissolves a solid, liquid, or gaseous solute, resulting in a solution.The most common solvent in everyday life is water....
, benzaldehyde is used chiefly in the synthesis of other organic compounds, ranging from pharmaceuticals to plastic additives. It is also an important intermediate for the processing of perfume and flavoring compounds and in the preparation of certain aniline
Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
 dye
Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
s.

The synthesis of mandelic acid
Mandelic acid

Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents....
 starts from benzaldehyde:

Benzaldehyde Chemical Mandelicacid
First hydrocyanic acid is added to benzaldehyde and the resulting mandelic acid nitrile
Nitrile

A nitrile is any organic compound which has a -Carbon=Nitrogen functional group. The -C=N functional group is called a nitrile group....
 is subsequently hydrolysed
Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
 to a racemic mixture of mandelic acid
Mandelic acid

Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents....
. (The scheme above depicts only one of the two formed enantiomer
Enantiomer

In chemistry, an enantiomer is one of two stereoisomers that are Superpose complete mirror images of each other, much as one's left and right Chirality are "the same" but opposite....
s).

Glaciologists LaChapelle and Stillman reported in 1966 that benzaldehyde and N-heptaldehyde inhibit the recrystallization of snow and therefore the formation of depth hoar
Depth hoar

Depth hoares are large crystals occurring at the base of a snowpack that form from when uprising water vapor freezing onto existing snow crystal....
. This treatment may prevent avalanches caused by unstable depth hoar layers. However, the chemicals are not in widespread use because they damage vegetation and contaminate water supplies.

Biology


Benzaldehyde Chemical Amygdalin
Almond
Almond

The Almond is a species of tree of the genus Prunus, belonging to the subfamily Prunoideae of the family Rosaceae and native to the Middle East....
s, apricot
Apricot

The Apricot is a species of Prunus, classified with the plum in the subgenus Prunus. The native range is somewhat uncertain due to its extensive prehistoric cultivation, but most likely in northern and western China and Central Asia, possibly also Korea and Japan....
s, apple
APPLE

This article is about the satellite APPLE. For the fruit apple, see Apple. For other uses see Apple .The Ariane Passenger PayLoad Experiment , was an experimental communication satellite with a C-Band transponder launched by Indian Space Research Organisation satellite on June 19, 1981 by Ariane 1, a launch vehicle of the European Spac...
s and cherry
Cherry

The word cherry refers to a fleshy fruit that contains a single stony seed. The cherry belongs to the family Rosaceae, genus Prunus, along with almonds, peaches, plums, apricots and bird cherry ....
 kernels, contain significant amounts of amygdalin
Amygdalin

Amygdalin , C20H27NO11, is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet...
. This glycoside
Glycoside

In chemistry, glycosides are certain molecules in which a sugar part is bound to some other part. Glycosides play numerous important roles in living organisms....
 breaks up under enzyme catalysis into benzaldehyde, hydrocyanic acid and two molecules of glucose
Glucose

Glucose , a monosaccharide also known as grape sugar, blood sugar, or corn sugar, is a very important carbohydrate in biology....
.

External links

 
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