Benzoic acid, C₇H₆O₂ (or C₆H₅COOH), 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. This weak acid and its salts are used as a food preservative. Benzoic acid is an important precursor for the synthesis of many other organic substances. The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Basic schematic of a mass spectrometer Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -(C=O)-OH, usually written as -COOH. In general, the salts and anions... Phenylacetic acid (synonyms: α-Toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid) is an organic compound containing a phenyl moiety and an acetic acid moiety. ... Hippuric acid (Gr. ... Salicylic acid is the chemical compound with the formula C6H4(OH)CO2H, where the OH group is adjacent to the carboxylic acid group. ... Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ... This page may meet Wikipedias criteria for speedy deletion. ... Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C6H5COCl, with an irritating odour. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... The term aromatic compound may also refer to: any organic compound possessing a strong olfactory aroma aromatic hydrocarbons (originally named as a subset of the above; however, aromatic hydrocarbons do not necessarily possess any smell whatsoever) ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -(C=O)-OH, usually written as -COOH. In general, the salts and anions... Commonly called benzoin, it is called benzoin resin here to distinguish it from the crystalline compound benzoin. ...

[edit] History

Benzoic acid was discovered in the 16th century. The dry distillation of gum benzoin was first described by Nostradamus (1556), and subsequently by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).^[1] Dry distillation is the heating of solid materials to produce liquid or gaseous products (which may condense into solids). ... Commonly called benzoin, it is called benzoin resin here to distinguish it from the crystalline compound benzoin. ... Nostradamus original portrait by his son Cesar Nostradamus (December 14, 1503 – July 2, 1566), Latinised name of Michel de Nostredame, was one of the worlds most famous publishers of prophecies. ... Events January 16 - Abdication of Emperor Charles V. His son, Philip II becomes King of Spain, while his brother Ferdinand becomes Holy Roman Emperor January 23 - The Shaanxi earthquake, the deadliest earthquake in history, occurs with its epicenter in Shaanxi province, China. ... Girolamo Ruscelli (Viterbo 1500 — Venice 1566), using the pseudonym Alessio Piemontese and better known under his latinized name of Alexius Pedemontanus, was an 14th century Italian physician, alchemist and cartographer. ... Events February 27 - The Treaty of Berwick, which would expel the French from Scotland, is signed by England and the Congregation of Scotland The first tulip bulb was brought from Turkey to the Netherlands. ... Blaise de Vigenère (April 5, 1523 - 1596) was a French diplomat and cryptographer. ... Events February 5 - 26 catholics crucified in Nagasaki, Japan. ...

Justus von Liebig and Friedrich Wöhler determined the structure of benzoic acid in 1832.^[2] They also investigated how hippuric acid is related to benzoic acid. Freiherr Justus von Liebig (May 12, 1803 in Darmstadt, Germany – April 18, 1873 in Munich, Germany) was a German chemist who made major contributions to agricultural and biological chemistry, and worked on the organization of organic chemistry. ... Friedrich Wöhler (July 31, 1800 - September 23, 1882) was a German chemist, best-known for his synthesis of urea, but also the first to isolate several of the elements. ... 1832 was a leap year starting on Sunday (see link for calendar). ... Hippuric acid (Gr. ...

In 1875 Salkowski discovered the antifungal abilities of benzoic acid, which were used for a long time in the preservation of benzoate containing fruits.^[3] 1875 (MDCCCLXXV) was a common year starting on Friday (see link for calendar). ... Something antifungal kills or inhibits the growth of fungus. ... Binomial name Rubus chamaemorus L. The Cloudberry (Rubus chamaemorus) is a slow-growing species of Rubus, producing edible fruit. ...

[edit] Production

[edit] Industrial preparations

Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. The process is catalyzed by cobalt or manganese naphthenates. The process uses cheap raw materials, proceeds in high yield, and is considered environmentally attractive. Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, reminiscent of the sweet smell of the related compound benzene. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... This article or section does not cite its references or sources. ... General Name, Symbol, Number manganese, Mn, 25 Chemical series transition metals Group, Period, Block 7, 4, d Appearance silvery metallic Atomic mass 54. ...

Image File history File links Benzoic_acid-chemical-synthesis-1. ...

U.S. production capacity is estimated to be 126000 tonnes per year, much of which is consumed domestically to prepare other industrial chemicals. A tonne or metric ton (symbol t), sometimes referred to as a metric tonne, is a measurement of mass equal to 1,000 kilograms. ...

[edit] Historical preparations

The first industrial process involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using iron or iron salts as catalyst. The resulting calcium benzoate is converted to benzoic acid with hydrochloric acid. The product contains significant amounts of chlorinated benzoic acid derivatives. For this reason, benzoic acid for human consumption was obtained by dry distillation of gum benzoin. Even after the discovery of other synthesis methods, it was forbidden to use benzoic acid of other source than gum benzoin.^{[citation needed]} Calcium hydroxide is a chemical compound with the chemical formula Ca(OH)2. ... General Name, Symbol, Number iron, Fe, 26 Chemical series transition metals Group, Period, Block 8, 4, d Appearance lustrous metallic with a grayish tinge Atomic mass 55. ... Iron(III) chloride, generically called ferric chloride, is an iron-based salt of chemical formula FeCl3. ... It has been suggested that this article or section be merged into Catalysis. ... Calcium benzoate is the calcium salt of benzoic acid. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride (HCl). ...

Alkyl substituted benzene derivatives give benzoic acid with the stoichiometric oxidants potassium permanganate, chromium trioxide, nitric acid. An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... Potassium permanganate is the chemical compound KMnO4. ... In chemistry, chromic acid (or Jones reagent) is a chromium (Cr) compound, yet to be isolated, that would have the formula H2CrO4. ... The chemical compound nitric acid (HNO3), otherwise known as aqua fortis or spirit of nitre, is an aqueous solution of hydrogen nitrate (anhydrous nitric acid). ...

[edit] Uses

[edit] Food preservative

Benzoic acid and its salts are used as a food preservative, represented by the E-numbers E210, E211, E212, and E213. Benzoic acid inhibits the growth of mold, yeast^[4] and some bacteria. It is either added directly or it is created from reactions with its sodium, potassium or calcium salt. The mechanism starts with the absorption of benzoic acid in to the cell. If the intracellular pH changes to 5 or lower the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%. The effectivity of benzoic acid and benzoate is thus dependent on the pH of the food.^[5] Acidic food and beverage like fruit juice (citric acid), sparkling drinks (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) or other acidified food are preserved with benzoic acid and benzoates. A preservative is a natural or synthetic chemical that is added to products such as foods, pharmaceuticals, paints, biological samples, etc. ... For the mathematical constant see: E (mathematical constant). ... Structural formula Benzoic acid, C6H5C(O)OH, is an aromatic carboxylic acid. ... Sodium benzoate (E211), also called benzoate of soda, has chemical formula C6H5COONa. ... Potassium benzoate, the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacteria. ... Calcium benzoate is the calcium salt of benzoic acid. ... Microscopic photo of the hyphae and spores of Aspergillus fumigatus Moldy bread Moldy nectarines Molds (or moulds) are microscopic multinucleated multicellular fungi made up of hyphae (tube-like structures) which are usually separated from each other by divisions called septa. ... Typical divisions Ascomycota Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota Basidiomycotina (club fungi) Urediniomycetes Sporidiales Yeasts are unicellular, eukaryotic microorganisms classified in the kingdom Fungi. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Atomic mass 22. ... General Name, Symbol, Number potassium, K, 19 Chemical series alkali metals Group, Period, Block 1, 4, s Appearance silvery white Atomic mass 39. ... General Name, Symbol, Number calcium, Ca, 20 Chemical series alkaline earth metals Group, Period, Block 2, 4, s Appearance silvery white Atomic mass 40. ... . The initial letter is shown capitalized due to technical restrictions. ... It has been suggested that this article or section be merged with Anaerobic respiration. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... Phosphofructokinase (PFK) is the most important regulatory enzyme (EC 2. ... Juice is the liquid naturally contained in plants. ... Citric acid is a weak organic acid found in citrus fruits. ... Carbon dioxide is a chemical compound composed of one carbon and two oxygen atoms. ... A soft drink is a drink that contains no alcohol. ... Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is an inorganic mineral acid having the chemical formula H3PO4. ... It has been suggested that Leuconostoc mesenteroides be merged into this article or section. ... Vinegar is often infused with spices or herbs—as here, with oregano. ...

Concern has been expressed that benzoic acid and its salts may react with ascorbic acid (vitamin C) in some soft drinks, forming small quantities of benzene.^[6][7] This article deals with the molecular aspects of ascorbic acid. ... Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ...

See also Benzene in soft drinks. // Background Benzene is a carcinogen. ...

[edit] Synthesis

Benzoic acid is used to make a large number of chemicals, important examples:

• Benzoyl chloride, C₆H₅C(O)Cl, is obtained by treatment of benzoic with thionyl chloride, phosgene or one of the chlorides of phosphorus. C₆H₅C(O)Cl is an important starting material for several benzoic acid derivates like benzyl benzoate, which is used as artificial flavours and insect repellents.
• Benzoyl peroxide, [C₆H₅C(O)O]₂, is obtained by treatment with peroxide.^[8] The peroxide is a radical starter in polymerization reactions and also a component in cosmetic products.
• Benzoate plasticizers, such as the glycol-, diethylengylcol-, and triethyleneglycol esters are obtained by transesterification of methyl benzoate with the corresponding diol. Alternatively these species arise by treatment of benzoylchloride with the dool. These plasticizers are used similarly to those derived from terephthalic acid ester.
• Phenol, C₆H₅OH, is obtained by oxidative decarboxylation at 300-400°C. The temperature required can be lowered to 200°C by the addition of catalytic amounts of copper(II) salts. The phenol can be converted to cyclohexanol, which is than starting material for nylon synthesis.

Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C6H5COCl, with an irritating odour. ... R-phrases , , , S-phrases , , , Flash point non flammable Supplementary data page Structure and properties n, εr, etc. ... Phosgene (also known as carbonyl chloride, COCl2) is a highly toxic gas or refrigerated liquid that was used as a chemical weapon in World War I. It has no color, but is detectable in air by its odor, which resembles moldy hay. ... Phosphorus trichloride Phosphorus pentachloride (gas phase structure) Phosphorus oxychloride[1] Several phosphorus chlorides are known. ... This page may meet Wikipedias criteria for speedy deletion. ... Flavouring (CwE) or flavoring (AmE) is a product which is added to food in order to change or augment its taste. ... Commercial insect repellents. ... R-phrases , , S-phrases , , , Autoignition temperature 80°C RTECS number DM8575000 Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Tube of Basiron, a water-based 5% benzoyl peroxide preparation for the treatment of acne. ... Peroxide has three distinct meanings: // Main article: hydrogen peroxide In common usage, peroxide is an aqueous solution of hydrogen peroxide (HOOH or H2O2) sold for use as a disinfectant or mild bleach. ... Another meaning of initiator is SCSI initiator. ... This is the article about the process. ... Plasticizers are additives that soften the materials (usually a plastic or a concrete mix) they are added to. ... In organic chemistry, transesterification is the process of exchanging the alkoxy group of an ester compound by another alcohol. ... Methyl benzoate is an ester with the chemical formula C6H5COOCH3. ... A diol is a chemical compound containing two hydroxyl groups (-OH groups). ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... For other uses, see Copper (disambiguation). ... Cyclohexanol is a secondary alcohol, formula C6H12O, consisting of a cyclohexane ring with one hydrogen substituent replaced by a hydroxyl group. ... Nylon represents a family of synthetic polymers, a thermoplastic material, first produced on February 28, 1935 by Gerard J. Berchet of Wallace Carothers research group at DuPont. ...

[edit] Biology and health effects

Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters.^[9] Commonly called benzoin, it is called benzoin resin here to distinguish it from the crystalline compound benzoin. ...

Benzoic acid is present as part of hippuric acid (N-Benzoylglycine) in urine of mammals, especially herbivores (Gr. hippos = horse; ouron = urine). Humans produce about 0.44 g/L hippuric acid per day in their urine, and if the person is exposed to toluene or benzoic acid it can rise above that level.^[10] Hippuric acid (Gr. ... This article or section is in need of attention from an expert on the subject. ... Orders Subclass Monotremata Monotremata Subclass Marsupialia Didelphimorphia Paucituberculata Microbiotheria Dasyuromorphia Peramelemorphia Notoryctemorphia Diprotodontia Subclass Placentalia Xenarthra Dermoptera Desmostylia Scandentia Primates Rodentia Lagomorpha Insectivora Chiroptera Pholidota Carnivora Perissodactyla Artiodactyla Cetacea Afrosoricida Macroscelidea Tubulidentata Hyracoidea Proboscidea Sirenia The mammals are the class of vertebrate animals primarily characterized by the presence of mammary... In zoology, an herbivore is an animal that is adapted to eat primarily plants (rather than meat). ... Hippuric acid (Gr. ... Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, reminiscent of the sweet smell of the related compound benzene. ...

For humans the IPCS suggests a provisional tolerable intake would be 5 mg/kg body weight per day.^[11][12] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. Lethal dose for cats can be as low as 300 mg/kg body weight, whereas mice die of an intake of 6000 mg/kg body weight.^[13] The LD₅₀ for rats is 1700 mg/kg, and for humans 500 mg/kg.^[11][12] Trinomial name Felis silvestris catus (Linnaeus, 1758) The cat (or domestic cat, house cat) is a small domesticated carnivorous mammal. ... For other meanings of the word salt see table salt or salt (disambiguation). ... This is an article about wild rats; for pet rats, see Fancy rat Species 50 species; see text *Several subfamilies of Muroids include animals called rats. ... Feral mouse A mouse (Plural mice) is a mammal that belongs to one of numerous species of small rodents. ... An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ...

[edit] Chemistry

Reactions of benzoic acid can occur at either the aromatic ring or the carboxylic group: An aromatic hydrocarbon (abbreviated as AH), or arene is a hydrocarbon, the molecular structure of which incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds. ... In chemistry, a carboxyl group is a functional group consisting of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl (-OH) group, typically written as -COOH: where R is a hydrogen or an organic group. ...

[edit] Aromatic ring

Image File history File links Download high resolution version (910x260, 5 KB) Summary I created it with a chemical drawing programm and transformed it into a PNG Licensing File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ...

Electrophilic aromatic substitution reaction will take place mainly in 3-position to the electron-withdrawing carboxylic group. Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, in an aromatic system is replaced by an electrophile. ... In organic chemistry, a deactivating group is a functional group attached to a benzene molecule that removes electron density from the benzene ring, making electrophilic aromatic substitution reactions slower and more difficult than they would be on benzene alone. ... In chemistry, a carboxyl group is a functional group consisting of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl (-OH) group, typically written as -COOH: where R is a hydrogen or an organic group. ...

The second substitution reaction (on the right) is slower because the first nitro group is deactivating.^[14] Conversely, if an activating group (electron-donating) was introduced (eg alkyl), a second substitution reaction would occur more readily than the first and the disubstituted product might not accumulate to a significant extent.

[edit] Carboxylic group

All the reactions mentioned for carboxylic acids are also possible for benzoic acid. Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -(C=O)-OH, usually written as -COOH. In general, the salts and anions...

• Benzoic acid esters are the product of the acid catalysed reaction with alcohols.
• Benzoic acid amides are more easily available by using activated acid derivatives (such as benzoyl chloride) or by coupling reagents used in peptide synthesis like DCC and DMAP.
• The more active benzoic anhydride is formed by dehydration using acetic anhydride or phosphorus pentoxide.
• Highly reactive acid derivatives such as acid halides are easily obtained by mixing with halogenation agents like phosphorus chlorides or thionyl chloride.
• Orthoesters can be obtained by the reaction of alcohols under acidic water free conditions with benzonitrile.
• Reduction to benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH₄ or sodium borohydride.
• The copper catalysed decarboxylation of benzoate to benzene may be effected by heating in quinoline. Alternatively, Hunsdiecker decoarboxylation can be achieved by forming the silver salt and heating.

For the Biblical Ester, see Esther. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... In chemistry, the term amide has several meanings. ... Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C6H5COCl, with an irritating odour. ... It has been suggested that solid phase peptide synthesis be merged into this article or section. ... Dicyclohexylcarbodiimide (DCC) is an organic compound primarily used to couple amino acids during artificial protein synthesis. ... Chemical structure of DMAP 4-Dimethylaminopyridine, abbreviated as DMAP, is an acetylation catalyst with reagents such as Acetyl chloride or Acetic anhydride that is much stronger than pyridine or triethylamine . ... Acid anhydrides are chemical compounds that look like, and sometimes are, the product resulting from dehydration of an acid. ... Acetic anhydride, also known as ethanoic anhydride, is one of the simplest of acid anhydrides. ... Phosphorus pentoxide, perhaps more accurately diphosphorus pentoxide, is so called because of its empirical formula P2O5, as should be expected of any element in oxidation number +5. ... An acyl halide (also known as an acid halide) is an organic compound containing a carbon atom which is double_bonded to an oxygen atom and singly bonded to a chlorine atom. ... In chemistry, halogenation is a chemical reaction that replaces a hydrogen atom with a halogen atom. ... Phosphorus trichloride Phosphorus pentachloride (gas phase structure) Phosphorus oxychloride[1] Several phosphorus chlorides are known. ... R-phrases , , , S-phrases , , , Flash point non flammable Supplementary data page Structure and properties n, εr, etc. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... Benzonitrile, also called cyanobenzene or phenyl cyanide, is an aromatic organic compound with chemical formula C6H5CN and molecular mass 103. ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ... DIBAH (Diisobutylaluminum hydride) is a reducing agent, useful in reducing esters to aldehydes. ... Lithium aluminium hydride (LiAlH4), commonly abbreviated to LAH, is a powerful reducing agent used in organic chemistry. ... Sodium borohydride, also known as sodium tetrahydridoborate, has the chemical formula NaBH4 (CAS 16940-66-2). ... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... The benzoate ion is C6H5COO− (benzoic acid minus one hydrogen ion). ... Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. ... Image File history File links Download high resolution version (1074x694, 13 KB) Summary I created it with a chemical drawing programm and transformed it into a PNG Licensing File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ...

[edit] Laboratory preparations

Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedogical value. It is a common undergraduate preparation and an unusual feature of the compound is that its melting point equals its molecular weight (122). For all syntheses, benzoic acid can be purified by recrystallization from water owing to its high solubility in hot and poor solubility in cold water. The avoidance of organic solvents for the recrystallization makes this experiment particularly safe.

[edit] From benzonitrile

Under alkaline or acidic conditions, benzonitrile undergoes hydrolysis. The reaction proceeds via the intermediacy of the amide or imine, which is subsequently hydrolysed to the acid or salt. Benzonitrile, also called cyanobenzene or phenyl cyanide, is an aromatic organic compound with chemical formula C6H5CN and molecular mass 103. ... Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ... Amide functional group In chemistry, an amide is one of two kinds of compounds: - the organic functional group characterized by a carbonyl group (C=O) linked to a nitrogen atom (N), or a compound that contains this functional group (pictured to the right); or - a particular kind of nitrogen anion. ... An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ...

[edit] From benzamide

Benzamide, C₆H₅CONH₂, may be hydrolysed by aqueous acid (or alkali), producing benzoic acid (or its salt in alkali): Structure of Benzamide Amisulpride - a substituted benzamide Benzamides are a class of chemical compounds derived from Benzamid (R = H), the carbonic acid amide of benzoic acid. ...

C₆H₅CONH₂ → C₆H₅CO₂H + NH₃

[edit] From benzaldehyde

The base-induced disproportionation of benzaldehyde, the Cannizzaro reaction, affords equal amounts of benzoate and benzyl alcohol; the latter can be removed by distillation. Disproportionation is a concept in chemistry and is a redox reaction where a reactant is both oxidised and reduced in the same chemical reaction. ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... The Cannizzaro reaction named after Stanislao Cannizzaro is a chemical reaction that involves the base-induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position. ... Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ... Laboratory distillation set-up using, without a fractionating column 1: Heat source 2: Still pot 3: Still head 4: Thermometer/Boiling point temperature 5: Condenser 6: Cooling water in 7: Cooling water out 8: Distillate/receiving flask 9: Vacuum/gas inlet 10: Still receiver 11: Heat control 12: Stirrer speed...

[edit] From bromobenzene

Bromobenzene in diethyl ether is stirred with magnesium turnings to produce phenylmagnesium bromide (C₆H₅MgBr). This Grignard reagent is slowly added to dry ice (solid carbon dioxide) to give benzoate. Dilute acid is added to form benzoic acid. Bromobenzenes are a group of halobenzenes formed in a substitution reaction between bromine and benzene with a hydrogen bromide biproduct. ... various examples of swarf, including a block of compressed swarf Swarf (or turnings) is the debris or waste resulting from metalworking operations. ... Phenylmagnesium bromide, with the simplified formula C6H5MgBr, is a a magnesium-containing organometallic compound. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ...

Image File history File links Benzoic_acid_synthesis. ...

[edit] From benzyl alcohol

Benzyl alcohol is refluxed with potassium permanganate or other oxidizing reagents in water. The mixture hot filtered to remove manganese oxide and then allowed to cool to afford benzoic acid. Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ...

[edit] References

1. ^ Neumüller O-A (1988). Römpps Chemie-Lexikon, 6, Stuttgart: Frankh'sche Verlagshandlung. ISBN 3-440-04516-1.
2. ^ Liebig J, Wöhler F (1832). "". Liebigs An Chem 3: 249.
3. ^ Salkowski E (1875). "". Berl Klin Wochenschr 12: 297-298.
4. ^ A D Warth (1991). "Mechanism of action of benzoic acid on Zygosaccharomyces bailii: effects on glycolytic metabolite levels, energy production, and intracellular pH.". Appl Environ Microbiol. 1991 December 1: 1.
5. ^ Pastrorova I, de Koster CG, Boom JJ (1997). "Analytic Study of Free and Ester Bound Benzoic and Cinnamic Acids of Gum Benzoin Resins by GC-MS HPLC-frit FAB-MS". Phytochem Anal 8: 63-73. DOI:<63::AID-PCA337>3.0.CO;2-Y 10.1002/(SICI)1099-1565(199703)8:2<63::AID-PCA337>3.0.CO;2-Y.
6. ^ Goldstein, David. "FDA finds benzene in soft drinks", Knight Ridder, 2006-03-03.
7. ^ http://www.bfr.bund.de/cm/245/indications_of_the_possible_formation_of_benzene_from_benzoic_acid_in_foods.pdf BfR article
8. ^ Silbert, L. S.; Siegel, E.; Swern, D. "Peroxybenzoic Acid" Organic Syntheses, Collected Volume 5, p.904 (1973).
9. ^ Tomokuni K, Ogata M (1972). "Direct Colorimetric Determination of Hippuric Acid in Urine". Clin Chem 18: 349-351.
10. ^ Krebs HA, Wiggins D, Stubbs M (1983). "Studies on the mechanism of the antifungal action of benzoate". Biochem J 214: 657-663.
11. ^ ^{a b} Chemical Profiles (updated 2002-04-03)
12. ^ ^{a b} Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE
13. ^ Bedford PG, Clarke EG (1972). "Experimental benzoic acid poisoning in the cat". Vet Rec 90: 53-58. PMID 4672555
14. ^ Brewster, R. Q.; Williams, B.; Phillips, R. (1955). "3,5-Dinitrobenzoic Acid". Organic Syntheses, Collected Volume 3: 337.

Freiherr Justus von Liebig (May 12, 1803 in Darmstadt, Germany – April 18, 1873 in Munich, Germany) was a German chemist who made major contributions to agricultural and biological chemistry, and worked on the organization of organic chemistry. ... Friedrich Wöhler (July 31, 1800 - September 23, 1882) was a German chemist, best-known for his synthesis of urea, but also the first to isolate several of the elements. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Partial list of newspapers The following is a partial list of newspapers owned by Knight Ridder: Contra Costa Times Detroit Free Press Kansas City Star The Miami Herald Philadelphia Inquirer Saint Paul Pioneer Press San Jose Mercury News The State External link Knight Ridder corporate website Categories: Companies traded on... 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... March 3 is the 62nd day of the year in the Gregorian Calendar (63rd in leap years). ... The mild oxidation of primary or secondary alcohols to aldehydes or ketones with a mixture of oxalyl chloride, dimethylsulfoxide and triethylamine is called the Swern oxidation. ... For album titles with the same name, see 2002 (album). ... April 3 is the 93rd day of the year (94th in leap years) in the Gregorian calendar, with 272 days remaining. ...

[edit] Further reading

• Cosmetic Ingredient Review Expert Panel Bindu Nair (2001). "Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate". Int J Tox 20 (Suppl. 3): 23-50.

[edit] External links

• International Chemical Safety Card 0103
• CID 243 from PubChem
• ChemicalLand

• Links to external chemical sources.