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65-85-0 Usage

description

Benzoic acid is the simplest member of the aromatic carboxylic acid family. It is a weak acid that is a precursor for the synthesis of many important organic compounds. More than 90 percent of commercial benzoic acid is converted directly to phenol and caprolactam. Its use in the production of glycol benzoates for the application of plasticizer in adhesive formulations is increasing. The organic compound is also used in the manufacture of alkyd resins and drilling mud additive for crude oil recovery applications. It is also used as a rubber polymerization activator, retardant, resins, alkyd paint, plasticizers, dyestuffs, and fibers. Benzoic acid and its esters occur in apricots, cranberries, mushrooms and jasmine plants. The history of benzoic acid dates back to sixteenth century. In the year of 1875 Salkowski a prominent scientist discovered its antifungal abilities. In medicine, benzoic acid is the principal component of benzoin resin, and is a constituent of Whitfield’s ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete’s foot.

Chemical Properties

Different sources of media describe the Chemical Properties of 65-85-0 differently. You can refer to the following data:
1. Scaly or needle like crystals. With the smell of formaldehyde or benzene. Slightly soluble in water, soluble in ethanol, methanol, diethyl ether, chloroform, benzene, toluene, CS2, CCl4 and turpentine.
2. Benzoic acid,C6H5COOH, also known as benzene carboxylic acid and phenyl formic acid,is a colorless, monoclinic crystalline solid that has a melting point of 122.4"C and sublimes readily at 100·C. It is an aromatic carboxylic acid that is slightly soluble in water and moderately soluble in alcohol and ether. It is used as a preservative and its derivatives are valuable in medicine, commerce, and industry.

history

Benzoic acid was found in the 16th century. In 1556, Nostradamus first described carbonization effect of benzoin; After the Alexius Pedemontanus and Brian blessed decipher were discovered in 1560 and 1596. In 1875, the salkowski discovered the antifungal potency of benzoic acid, so benzoic acid is used for long term preservation cloudberry.

food preservatives

Benzoic acid and sodium benzoate are commonly used food preservative. In acidic conditions, it has inhibitory effect on yeast and mold. When pH value is 3 antibacterial strength, when pH was 6 for a lot of mould effect is very poor, so the inhibition the optimum pH value is 2.5-4.0. In the food industry with plastic barrels concentrated fruit and vegetable juice, the maximum usage shall not exceed 2.0g/kg; in the jam (not including canned), fruit juice (taste) drinks, soy sauce, vinegar in the maximum amount is 1.0g/kg; in Wine, candy, wine in the maximum amount of 0.8g/kg in the low salt; pickles, sauces, candied fruit, use the largest 0.5g/kg in carbonate; use the largest beverage 0.2g/kg. because of solubility of benzoic acid, when used will be stirring, or dissolved in a small amount of hot water or ethanol. The use of concentrated fruit juice in the soft drink used for benzoic acid easily volatile with steam, it is commonly used in the sodium salt. Benzoic acid in food industry is a common preservative in dairy products, but not allowed to be added. In general, benzoic acid is considered to be safe. But for some special populations, including infants, long-term intake of benzoic acid may lead to asthma, urticaria, metabolic acidosis and other adverse reactions. Paul deodorant benzoic acid is also used as a beverage. As the cream sweet perfume fragrance. Can also be used for chocolate, lemon, orange, sub berries, nuts, candied fruit and other edible flavor type. Tobacco flavor also commonly used. In addition of benzoic acid is also used as a pesticide, medicine, dye, mordant and plasticizer agent for the production of raw materials, polyamide resin and alkyd resin modifying agent and steel equipment anti rust agent.

Uses

Different sources of media describe the Uses of 65-85-0 differently. You can refer to the following data:
1. 1. Used as a chemical reagent and preservative. 2. Benzoic acid is important type food preservative. Under acidic conditions, It has inhibitory effects to mold, yeast and bacteria , but the effect is weak acid producing bacteria. The most appropriate antimicrobial pH values is ranging from 2.5 to 4, generally lower, the pH value is appropriate from 4.5 to 5. In the food industry with plastic barrels concentrated fruit and vegetable juice, the maximum use amount shall not be over 2.0g/kg; in jam (excluding canned), (taste) juice drink, soy sauce, vinegar in the maximum dose of 1.0g/kg; in soft candy, wine, wine in the maximum dose of 0.8 g/kg separately; in the low salt pickled vegetables, the sauce, candied fruit, maximum dose is 0.5 g/kg; in carbonated drinks in the largest amount of use is 0.2g/kg. due to benzoic acid, slightly soluble in water, its use can be a small amount of ethanol enable dissolved. 3.Preservative; anti microbial agents. Due to the low solubility of benzoic acid and use shall be stirring, or dissolved in a small amount of hot water or ethanol. When used in the soft drink with fruit juice concentrate, for benzoic acid easy volatile with the water vapor, so often used in the sodium salt, besides the above sodium equivalent to benzoic acid 0.847g. 4.Often used as a fixative agent or preservative. Also used as a fruit juice aroma conservation agents. As a perfume with perfume fragrance. Can also be used for chocolate, lemon, orange, berries, nuts, candied fruit type edible essence. Tobacco flavor is also commonly used. 5.Benzoic acid and its sodium salt are food preservatives. Under acidic conditions, it has inhibition of yeasts and molds. When pH 3, antibacterial strength and when pH 6, many fungi effect is very poor, so the antibacterial optimum pH is 2.5-4.0. Benzoic acid is mainly used for the production of sodium benzoate preservatives, dyes intermediates, pesticides, plasticizers, mordant, medicine, spice and also can be used as alkyd resin and polyamide resin modifier for the production of polyester, terephthalic acid and used equipment, iron and steel anti rust agent. 6.Mainly used for antifungal and antiseptic. 7.Used in medicine, dye carriers, plasticizer, spices and food preservatives such as production, and can also be used to paint of alkyd resin performance improvement; used as pharmaceutical and dye intermediates, used for the preparation of plasticizer and spices etc., as well as equipment, iron and steel anti rust agent.
2. Sodium benzoate is an important benzoic acid derivative produced industrially by neutralization of benzoic acid using sodium hydroxide or sodium bicarbonate solution. Calcium benzoate, potassium benzoate, and other benzoate salts are also produced. Benzoic acid and sodium benzoate (C6H5COONa) are used as food preservatives and added to foods, juices, and beverages that are acidic.
3. Calorimetry Benzoic acid is the most commonly used chemical standard to determine the heat of capacity of a bomb calorimeter. Feed stock Benzoic acid is used to make a large number of chemicals, important examples of which are : 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 in artificial flavours and insect repellents. Food preservative Benzoic acid and its salts are used as a food preservatives, represented by the E-numbers E210 , E211 , E212 , and E213 . Benzoic acid inhibits the growth of mold, yeast and some bacteria. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. The mechanism starts with the absorption of benzoic acid in to the cell. Medicinal Benzoic acid is a constituent of Whitfiel's ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot. As the principal component of benzoin resin, benzoic acid is also a major ingredient in both tincture of benzoin and Fria's balsam. Such products have a long history of use as topical antiseptics and inhalant decongestants. Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.

Hazard

Different sources of media describe the Hazard of 65-85-0 differently. You can refer to the following data:
1. Benzoic acid accumulation is less, low toxicity in the body involved and metabolism. If the excessive consumption of benzoic acid, the body's liver and kidney will be jeopardized. Maximum safety of carbonated drinks of benzoic acid usage is 5mg/kg of body weight, then calculated according to the weight of 60kg, daily limit is 300mg, benzoic acid for carbonated drinks, the maximum amount of use is 0.2g/kg, then drank 1.5kg of beverage is safe. It has strong toxic effects on microorganisms, but the toxicity of the sodium salt is very low. A daily dose of 0.5g, has no toxicity to the body , even in an amount of not more than 4g of health also has no harm. In human and animal tissues it can bind with protein components of the glycine and detoxification, formed hippuric acid excreted in the urine. Benzoic acid crystallites or dust on the skin, eyes, nose, and throat has stimulating effect. Even if its sodium salt, if you take a lot, also can damage to the stomach. The operator should wear protective equipment. Need to be stored in a dry and ventilated place moisture, heat, away from the fire source.
2. Moderately toxic by ingestion. Use restricted to 0.1% in foods.

Preparation

Different sources of media describe the Preparation of 65-85-0 differently. You can refer to the following data:
1. Industrial preparation method The industrial benzoic acid is mainly by toluene liquid phase air oxidation preparation. The process was with cobalt naphthenate as catalyst, in response to temperature is 140-160 ℃ and operating pressure is 0.2-0.3MPa and response generation benzoic acid. Reaction after steaming to toluene, and vacuum distillation and recrystallization to obtain the product. The process uses cheap raw materials, high yield. Therefore, it is industrial uses mainly the method. Laboratory preparation method of the main reaction: 1.C6H5CH3+ KMnO4+H2O-C6H5 COOK+KOH+MnO2+H2O(water in fron of the manganese dioxide is supplied with water reaction environment) 2.C6H5 COOK+HCl--C6H5 COOH Drug and dosage: Toluene 1.5g (1.7ml, 0.016mol), potassium permanganate 5g (0.032mol), CTAB(cetyl trimethyl ammonium bromide) 0.1g. Experimental operation: With 100 ml round bottom flask. Install a refluxing device. add 5g potassium permanganate, 0.1g of hexadecyl trimethyl ammonium bromide, 1.7 ml of toluene and 50 ml of water to the reaction flask, stir heated boiling (vigorous stirring, violent boiling), keep the reactant solution stable boiling. When large amounts of brown precipitate, potassium permanganate purple shallow or disappeared, the toluene layer disappeared, reaction has basically ended. Filter out of manganese dioxide precipitation, landfill leachate by concentrated hydrochloric acid, precipitation of benzoic acid precipitation, filtering to the crude product. The crude product water recrystallization. In a boiling water bath for drying, weighing, measuring the melting point.
2. By oxidation of toluene with nitric acid or sodium bichromate or from benzonitrile.

Description

Benzoic acid is a colorless, crystalline solid also known as benzenecarboxylic acid. It is the simplest aromatic carboxylic acid, with a carboxyl group (-COOH) bonded directly to the benzene ring. It is found naturally in the benzoin resin of a number of plants.

Physical properties

Colorless to white needles, scales, or powder with a faint benzoin or benzaldehyde-like odor. Shaw et al. (1970) reported a taste threshold in water of 85 ppm.

Occurrence

Reported found in fresh apple, apricot (Prunus armeniaca L.), strawberry fruit, cherry (Prunus cerasus L.), butter, boiled and cooked beef, pork fat, white wine, black tea, green tea, fresh plum, mushroom, Bourbon vanilla (Vanilla planifolia Andrews), and other natural sources. Reported as being a constituent of various oils, resins and flower absolutes; hyacinth, tuberose, neroli bigarade, Chinese cinnamon, cinnamon leaves, anise, vertiver, ylang-ylang, Tolu balsam and clove; it is contained in fairly sizable amounts in gum benzoin, from which benzoic acid is extracted by sublimation.

History

Benzoic acid was first isolated from the dry distillation of benzoin by Blaise de Vigenère (1523–1596) in the 16th century. Friedrich W?hler (1800–1882) and Justus von Liebig (1803–1873) prepared benzoic acid from oxidizing bitter almond oil (benzaldehyde) in 1832 and determined the formula for each of these compounds. They proposed that bitter almond oil, C7H6O, and benzoic acid were derivatives from the benzoyl radical, C7H5O; the radical theory was a major early theory in the development of organic chemistry.

Production Methods

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 green. Laboratory synthesis Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a common undergraduate preparation. For all syntheses, benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. The avoidance of organic solvents for the recrystallization makes this experiment particularly safe. Other possible recrystallization solvents include acetic acid (anhydrous or aqueous), benzene, acetone, petroleum ether, and a mixture of ethanol and water. The solubility of benzoic acid in over 40 solvents with references to original sources can be found as part of the Open Notebook Science Challenge.

Definition

ChEBI: A compound comprising a benzene ring core carrying a carboxylic acid substituent.

Reactions

Reactions of benzoic acid can occur at either the aromatic ring or the carboxyl group : Aromatic ring Electrophilic aromatic substitution reaction will take place mainly in 3- position due to the electron-withdrawing carboxylic group; i.e. benzoic acid is meta directing. The second substitution reaction (on the right) is slower because the first nitro group is deactivating. Conversely, if an activating group (electron - donating) was introduced (e.g., alkyl), a second substitution reaction would occur more readily than the first and the disubstituted product might accumulate to a significant extent. Carboxyl group All the reactions mentioned for carboxylic acids are also possible for benzoic acid. 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. Ortho esters 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 , Li Al H4 or sodium boro hydride. The copper catalyzed decarboxylation of benzoate to benzene may be effected by heating in quinoline. Also, Hunsdiecker decarboxylation can be achieved by forming the silver salt and heating. Benzoic acid can also be decarboxylated by heating with an alkali hydroxide or calcium hydroxide.

Biotechnological Production

Benzoic acid is exclusively chemically synthesized on an industrial scale. Toluene from petrochemical routes is oxidized in the presence of the catalyst potassium permanganate to benzoic acid . However, a recent study described for the first time a benzoic acid production process by fermentation using Streptomyces maritimus. The production of benzoic acid during cultivation on glucose, starch, and cellobiose has been investigated. The best results have been achieved with product concentrations of 460 mg.L-1 in 6 days using starch as substrate. Additionally, a genetically modified S. maritimus optimized for endo-glucanasesecretion has been tested on phosphoric acid swollen cellulose. A final product concentration of 125 mg.L-1 was observed after 4 days of cultivation.

Aroma threshold values

85 ppm.

Synthesis Reference(s)

Canadian Journal of Chemistry, 50, p. 3741, 1972 DOI: 10.1139/v72-592Chemistry Letters, 5, p. 147, 1976Tetrahedron Letters, 23, p. 2347, 1982 DOI: 10.1016/S0040-4039(00)87338-4

General Description

Boric acid,H3B03, also known as boracic acid, orthoboric acid, and sassolite, is a white solid composed of triclinic crystals.It is a derivative of barium oxide and is soluble in water. A white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses.

Air & Water Reactions

Vapor from molten Benzoic acid may form explosive mixture with air. The finely powdered dry acid is a significant dust explosion hazard [Bretherick, 5th ed., 1995, p. 884]. In air very rapid combustion occurs [Wilson, L.Y. et al., J. Chem. Ed., 1985, 62(10), p. 902]. Slightly soluble in water.

Reactivity Profile

At high temperature Benzoic acid can react with oxidizing reagents.

Health Hazard

Dust may be irritating to nose and eyes. At elevated temperatures, fumes may cause irritation of eyes, respiratory system, and skin.

Fire Hazard

Behavior in Fire: Vapor from molten Benzoic acid may form explosive mixture with air. Concentrated dust may form explosive mixture.

Agricultural Uses

Fungicide, Insecticide: Used in the manufacture of benzoates; plasticizers, benzoyl chloride, alkyd resins, in the manufacture of food preservatives, in use as a dye binder in calico printing; in curing of tobacco, flavors, perfumes, dentifrices, standard in analytical chemistry. Not currently registered for use in the U.S. Benzoic acid is currently used in about a dozen European countries.

Pharmaceutical Applications

Benzoic acid is widely used in cosmetics, foods, and pharmaceuticals, as an antimicrobial preservative. Greatest activity is seen at pH values between 2.5–4.5. Benzoic acid also has a long history of use as an antifungal agent in topical therapeutic preparations such as Whitfield’s ointment (benzoic acid 6% and salicylic acid 3%).

Trade name

RETARDER BA?; MICROL? Preservative; TENN-PLAS?; RETARDEX?; SALVO LIQUID?; SALVO POWDER?; TULSA?

Clinical Use

Benzoic acid is a metabolite of benzyl alcohol and sodium benzoate is the sodium salt of benzoic acid. These three related compounds are used as preservatives in a variety of products, such as cosmetics, toothpastes, hair products, medication preparations, and emollients, and in foods. They are well-recognized to cause nonimmunological CoU and reactions are concentration-dependent.Both oral intake and cutaneous contact of benzyl alcohol, benzoic acid, or sodium benzoate can cause immediate reactions; however, there is a lack of correlation between the two and skin tests should not be used to predict sensitivity to oral intake of these preservatives. Immediate reactions to the oral ingestion of these preservatives are rare. Nettis et al. investigated 47 patients with a history of urticaria after the ingestion of meals or products containing sodium benzoate, and only one patient had a generalized urticarial reaction to an oral challenge test of 50 mg of sodium benzoate.

Side effects

Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05 %). Ripe fruits of several Vaccinium species (e.g., cranberry, V. vitis idaea; bilberry, V. macrocarpon) contain as much as 0.03 – 0.13 % free benzoic acid. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena. Among animals, benzoic acid has been identified primarily in omnivorous or phytophageous species, e.g., in viscera and muscles of the Rock Ptarmigan (Lagopus muta) as well as in gland secretions of male muskoxen (Ovibos moschatus) or Asian bull elephants (Elephas maximus). Gum benzoin contains up to 20 % of benzoic acid and 40% benzoic acid esters.

Toxicology

Four-generation reproductive and developmental toxicities of benzoic acid were examined using diets containing 0, 0.5, and 1% of benzoic acid fed to male and female rats housed together for eight weeks. The second generation was observed through its entire life cycle and the third and fourth generations were examined by autopsy. No changes in normal patterns of growth, reproduction, or lactation during life were recorded and no morphological abnormalities were observed from the autopsies.Degradation pathways for benzoic acid also have been studied in detail and the results have supported the harmlessness of this substance. The total dose of benzoic acid is excreted within 10 to 14 hours and 75 to 80% is excreted within 6 hours. After conjugation with glycine, 90% of benzoic acid appears in the urine as hippuric acid. The rest forms a glucuronide,1-benzoylglucuronic acid. The lower aliphatic esters of benzoic acid are first hydrolyzed by esterase, which abounds in the intestinal wall and liver. The resulting benzoic acid subsequently is degraded in the usual manner.

Safety

Ingested benzoic acid is conjugated with glycine in the liver to yield hippuric acid, which is then excreted in the urine; care should be taken when administering benzoic acid to patients with chronic liver disease. Benzoic acid is a gastric irritant, and a mild irritant to the skin. It is also a mild irritant to the eyes and mucous membranes. Allergic reactions to benzoic acid have been reported, although a controlled study indicated that the incidence of urticaria in patients given benzoic acid is no greater than in those given a lactose placebo. It has been reported that asthmatics may become adversely affected by benzoic acid contained in some antiasthma drugs. The WHO acceptable daily intake of benzoic acid and other benzoates, calculated as benzoic acid, has been set at up to 5 mg/kg body-weight. The minimum lethal human oral dose of benzoic acid is 500 mg/kg body-weight. LD50 (cat, oral): 2 g/kg LD50 (dog, oral): 2 g/kg LD50 (mouse, IP): 1.46 g/kg LD50 (mouse, oral): 1.94 g/kg LD50 (rat, oral): 1.7 g/kg

Potential Exposure

Benzoic acid is used in production of plasticizers, benzoyl chloride, sodium benzoate and alkyl resins; in the manufacture of benzoates; in the manufacture of food preservatives; as a dye binder in calico printing; in curing of tobacco, flavors, perfumes, dentifrices; standard in analytical chemistry; antifungal agent.

Carcinogenicity

Benzoic acid was not genotoxic in bacterial assays or in in vitro mammalian assays.

Source

Naturally occurs in cranberries, ligonberries (1,360 ppm), peppermint leaves (20–200 ppb), tea leaves, cassia bark, carob, blessed thistle, purple foxglove, jasmine, hyacinth, apples, tobacco leaves, daffodils, autumn crocus, prunes, anise seeds, ripe cloves, and wild black cherry tree bark (Duke, 1992; quoted, Verschueren, 1983). Schauer et al. (1999) reported benzoic acid in diesel fuel at a concentration of 1,260 μg/g. Identified as an oxidative degradation product in the headspace of a used engine oil (10–30W) after 4,080 miles (Levermore et al., 2001). The gas-phase tailpipe emission rate from California Phase II reformulated gasoline-powered automobile equipped with a catalytic converter was 124 μg/km (Schauer et al., 2002). Benzoic acid is a by-product of benzoyl peroxide used in the bleaching of freshly milled wheat flour. A maximum benzoic acid concentration of 16 ppm was reported after 12 h of bleaching. The concentration decreased to 6 ppm after 3 months (Saiz et al., 2001). A liquid swine manure sample collected from a waste storage basin contained benzoic acid at a concentration of 4.0 mg/L (Zahn et al., 1997).

Environmental fate

Biological. Benzoic acid may degrade to catechol if it is the central metabolite whereas, if protocatechuic acid (3,4-dihydroxybenzoic acid) is the central metabolite, the precursor is 3- hydroxybenzoic acid (Chapman, 1972). Other compounds identified following degradation of benzoic acid to catechol include cis,cis-muconic acid, (+)-muconolactone, 3-oxoadipate enol lactone, and 3-oxoadipate (quoted, Verschueren, 1983). Pure microbial cultures hydroxylated benzoic acid to 3,4-dihydroxybenzoic acid, 2- and 4-hydroxybenzoic acid (Smith and Rosazza, 1974). In activated sludge, 65.5% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ = 365 nm) converted benzoic acid to carbon dioxide at a significant rate (Matthews, 1986). An aqueous solution containing chlorine and irradiated with UV light (λ = 350 nm) converted benzoic acid to salicylaldehyde and unidentified chlorinated compounds (Oliver and Carey, 1977). A carbon dioxide yield of 10.2% was achieved when benzoic acid adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Brubaker and Hites (1998) measured the OH radical rate constant for benzoic acid between 333 and 363 K. The rate constants (x 1012 cm3/sec) were 0.42 and 0.66 at 333 K (two determinations), 0.84 at 343 K, and 0.72 at 363 K. In water, benzoic acid reacted with OH radicals at a rate of 1.2 x 1013/M·h at 25 °C (Armbrust, 2000). Chemical/Physical. At an influent concentration of 1.0 g/L, treatment with GAC resulted in an effluent concentration of 89 mg/L. The adsorbability of the carbon used was 183 mg/g carbon (Guisti et al., 1974). Ward and Getzen (1970) investigated the adsorption of aromatic acids on activated carbon under acidic, neutral, and alkaline conditions. The amount of benzoic acid (10-4 M) adsorbed by carbon at pH values of 3.0, 7.0, and 11.0 were 49.7, 11.2, and 2.5%, respectively. Similarly, at influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the respective GAC adsorption capacities were 130, 51, 19, and 7.3 mg/g at pH 3.0 and 54, 0.76, 0.01, and 0.002 mg/g at pH 7.0 At pH 9.0 and influent concentrations of 10 and 1.0 mg/L, the GAC adsorption capacities were 21 and 0.008, respectively (Dobbs and Cohen, 1980).

storage

Aqueous solutions of benzoic acid may be sterilized by autoclaving or by filtration. A 0.1% w/v aqueous solution of benzoic acid has been reported to be stable for at least 8 weeks when stored in polyvinyl chloride bottles, at room temperature. When added to a suspension, benzoic acid dissociates, with the benzoate anion adsorbing onto the suspended drug particles. This adsorption alters the charge at the surface of the particles, which may in turn affect the physical stability of the suspension. The addition of sodium azide has been shown to increase the stability of benzoic acid in skin permeation experiments. The bulk material should be stored in a well-closed container in a cool, dry place.

Purification Methods

For use as a volumetric standard, analytical reagent grade benzoic acid should be carefully fused to ca 130o (to dry it) in a platinum crucible, and then powdered in an agate mortar. Benzoic acid has been crystallised from boiling water (charcoal), aqueous acetic acid, glacial acetic acid, *C6H6, aqueous EtOH, pet ether (b 60-80o), and from EtOH solution by adding water. It is readily purified by fractional crystallisation from its melt and by sublimation in a vacuum at 80o. The S-benzylisothiuronium salt has m 167o (from EtOH/H2O). [Beilstein 9 IV 273.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, caustics, ammonia, amines, isocyanates. Dust forms an explosive mixture with air.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Regulatory Status

GRAS listed. Accepted as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM and IV injections, irrigation solutions, oral solutions, suspensions, syrups and tablets, rectal, topical, and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Check Digit Verification of cas no

The CAS Registry Mumber 65-85-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 5 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 65-85:
(4*6)+(3*5)+(2*8)+(1*5)=60
60 % 10 = 0
So 65-85-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)/p-1

65-85-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B2635)  Benzoic Acid  >99.0%(GC)

  • 65-85-0

  • 25g

  • 100.00CNY

  • Detail
  • TCI America

  • (B2635)  Benzoic Acid  >99.0%(GC)

  • 65-85-0

  • 500g

  • 170.00CNY

  • Detail
  • Alfa Aesar

  • (A14062)  Benzoic acid, 99%   

  • 65-85-0

  • 250g

  • 175.0CNY

  • Detail
  • Alfa Aesar

  • (A14062)  Benzoic acid, 99%   

  • 65-85-0

  • 1000g

  • 377.0CNY

  • Detail
  • Alfa Aesar

  • (A14062)  Benzoic acid, 99%   

  • 65-85-0

  • 5000g

  • 875.0CNY

  • Detail
  • Alfa Aesar

  • (36230)  Benzoic acid, ACS, 99.5% min   

  • 65-85-0

  • 25g

  • 181.0CNY

  • Detail
  • Alfa Aesar

  • (36230)  Benzoic acid, ACS, 99.5% min   

  • 65-85-0

  • 100g

  • 360.0CNY

  • Detail
  • Alfa Aesar

  • (36230)  Benzoic acid, ACS, 99.5% min   

  • 65-85-0

  • 500g

  • 741.0CNY

  • Detail
  • Supelco

  • (47849)  Benzoicacid  analytical standard

  • 65-85-0

  • 000000000000047849

  • 368.55CNY

  • Detail
  • Supelco

  • (8S61336)  BenzoicAcid  2000 μg/mL in methylene chloride, analytical standard

  • 65-85-0

  • 8S61336

  • 306.54CNY

  • Detail
  • Sigma-Aldrich

  • (06185)  Benzoicacid  Standard for quantitative NMR, TraceCERT®

  • 65-85-0

  • 06185-1G

  • 1,731.60CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1050)  Benzoicacid  pharmaceutical secondary standard; traceable to USP

  • 65-85-0

  • PHR1050-1G

  • 732.19CNY

  • Detail

65-85-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name benzoic acid

1.2 Other means of identification

Product number -
Other names Benzoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Preservatives and Antioxidants
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:65-85-0 SDS

65-85-0Synthetic route

benzaldehyde
100-52-7

benzaldehyde

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With 2,2,2-trichloroethylperoxycarbonic acid; dihydrogen peroxide In dichloromethane Ambient temperature;100%
With potassium hydroxide; oxygen In 1,2-dimethoxyethane at 20℃; for 3.5h;100%
With [Cu2C6H4(CHNCH2CH2N(CH2C5H4N)2)2](2+)*2ClO4(1-)=C36H38Cu2N8(ClO4)2; oxygen In acetone at -90.16℃;100%
benzonitrile
100-47-0

benzonitrile

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With water at 45℃; pH=7.2; Microbiological reaction; aq. buffer;100%
With potassium tert-butylate; water In isopropyl alcohol at 25℃; Inert atmosphere;100%
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.25h; microwave irradiation;99%
benzyl alcohol
100-51-6

benzyl alcohol

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With barium permanganate In acetonitrile for 4h; Heating;100%
With iodosylbenzene In water at 20℃; for 30h; Oxidation;100%
With iodosylbenzene In water for 30h; sonication;100%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With sodium hydroxide at 166 - 168℃; under 5250.4 Torr; for 0.0166667h; Irradiation;100%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution;100%
With potassium hydroxide; Aliquat 336 at 200℃; for 0.0833333h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; microwave irradiation;98%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With barium permanganate In acetonitrile for 0.5h; Heating;100%
With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; under 760.051 Torr; Sealed tube;98%
With sodium periodate; manganese(II) 5,10,15,20-tetrakis(N-ethylpyridinium-4-yl)porphyrin In water at 60℃; for 4h;96%
phenacyl benzoate
33868-50-7

phenacyl benzoate

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2h; Irradiation;100%
With sodium hydrogen telluride In N,N-dimethyl-formamide for 0.333333h; Product distribution; Ambient temperature;1.11 g
With tetrabutyl ammonium fluoride; phenylmethanethiol In tetrahydrofuran Product distribution; various concentrations, other solvent, other thiols; other educts; selective removal of phenacyl ester group in the presence of benzyl and 4-nitrobenzyl ester groups;
benzoic acid tert-butyl ester
774-65-2

benzoic acid tert-butyl ester

A

benzoic acid
65-85-0

benzoic acid

B

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
With aluminum oxide; potassium hydroxide In diethyl ether for 21h; Product distribution; Ambient temperature; other solvent;A 100%
B 80%
vinyl benzoate
583-04-0

vinyl benzoate

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In benzene at 65 - 70℃; for 3h;100%
With Fe3O4@SiO2-[(4-(5-O3Si-pentylcarbamoyl)-2-pyridinecarboxylato)CpRu(η3-C3H5)]PF6 In methanol at 30℃; for 1h; Inert atmosphere; chemoselective reaction;99%
[(cyclopentadienyl)bis(acetonitrile)(triphenylphosphine)ruthenium(II)] hexafluorophosphate In methanol at 25℃; for 6h; Product distribution; Further Variations:; Solvents; Temperatures;98%
benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogen In methanol at 25℃; for 24h; Reagent/catalyst; Solvent; Temperature; chemoselective reaction;100%
With hydrogen; palladium diacetate; pyrographite In tetrahydrofuran; methanol at 25℃; under 760.051 Torr; for 12h;99%
With hydrogen; palladium diacetate; pyrographite In isopropyl alcohol at 25℃; under 760.051 Torr; for 14h;99%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With NH-pyrazole; air; sodium hydride In tetrahydrofuran for 5h; Ambient temperature;100%
With iodopentafluorobenzene bis(trifluoroacetate) In water; benzene Mechanism;94%
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 48h;94%
benzaldehyde
100-52-7

benzaldehyde

Lithium; (Z)-2-chloro-1-trimethylsilanyl-hex-1-en-1-olate

Lithium; (Z)-2-chloro-1-trimethylsilanyl-hex-1-en-1-olate

A

(Z)-α-butylcinnamaldehyde
128649-19-4

(Z)-α-butylcinnamaldehyde

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
at -78℃; for 3h;A 97%
B 100%
at -78℃; for 3h; Mechanism; further α-chloroacyltrimethylsilanes, further aldehydes;A 97%
B 100%
Conditions
ConditionsYield
With sodium perborate In acetic acid for 1.5h; steam bath;100%
With (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)); oxygen; pivalaldehyde In acetonitrile for 6h; Ambient temperature;98%
With Oxone; 3,3'-diiodo-2,2',6,6'-tetramethoxy-4,4'-biphenyldicarboxylic acid In nitromethane; water at 30 - 35℃; for 14h;98%
para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
Stage #1: para-chlorobenzoic acid With palladium/alumina; hydrogen; potassium carbonate In water at 60℃;
Stage #2: With hydrogenchloride In water
100%
With hydrogen; triethylamine; palladium on activated charcoal In methanol at 20℃; for 6h;99%
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogen; triethylamine; palladium on activated charcoal In methanol at 20℃; for 3h;100%
With borane-ammonia complex In water; isopropyl alcohol at 40℃; for 3h; Sealed tube;97%
With 1H-imidazole; copper ammonium sulphate hexahydrate; lithium tert-butoxide In N,N-dimethyl-formamide; isopropyl alcohol for 72h; Irradiation;87%
1-benzoylimidazole
10364-94-0

1-benzoylimidazole

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With morpholine; water at 20℃; for 0.333333h;100%
With 1H-imidazole; potassium chloride In water; acetonitrile at 25 - 50℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.);
3-methyl-2-butenyl benzoate
5205-11-8

3-methyl-2-butenyl benzoate

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With methoxybenzene In toluene for 6h; Heating;100%
With Montmorillonite K-10 clay; toluene for 0.333333h; Dealkylation; Microwave irradiation;98%
With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 5h;95%
(1R,9R)-9-Phenyl-10,11,12-trioxa-tricyclo[7.2.1.02,7]dodeca-2,4,6-triene

(1R,9R)-9-Phenyl-10,11,12-trioxa-tricyclo[7.2.1.02,7]dodeca-2,4,6-triene

A

1,2-bis(3-formyl-4-phenyl)ethane
138771-02-5

1,2-bis(3-formyl-4-phenyl)ethane

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With iron(II) sulfate In tetrahydrofuran; water at 20℃; for 16h;A 100%
B 95%
Perbenzoic acid
93-59-4

Perbenzoic acid

bis-benzenesulfenyl-amine
24364-84-9

bis-benzenesulfenyl-amine

A

benzoic acid phenyl ester
93-99-2

benzoic acid phenyl ester

B

biphenyl
92-52-4

biphenyl

C

benzoic acid
65-85-0

benzoic acid

D

diphenyldisulfane
882-33-7

diphenyldisulfane

E

N2, tar

N2, tar

Conditions
ConditionsYield
In benzene Kinetics; Product distribution; Mechanism; isotopic effect, effect of benzoic acid and styrene on the reaction;A 1.4%
B 0.2%
C 100%
D 50%
E n/a
benzoic acid methoxymethyl ester
54354-04-0

benzoic acid methoxymethyl ester

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h;100%
With bismuth(III) chloride; water In acetonitrile at 50℃; for 2h;89%
(1-nosyl-5-nitroindol-3-yl)methyl benzoate

(1-nosyl-5-nitroindol-3-yl)methyl benzoate

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
Stage #1: (1-nosyl-5-nitroindol-3-yl)methyl benzoate With 2-(N,N-dimethylamino)ethylthiol hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.25h; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether; water; acetonitrile Inert atmosphere;
100%
[(6-Ph2TPA)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

[(6-Ph2TPA)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

A

[(6-Ph2TPA)Ni(O2CPh)]ClO4
932703-85-0

[(6-Ph2TPA)Ni(O2CPh)]ClO4

B

phenacyl benzoate
33868-50-7

phenacyl benzoate

C

carbon monoxide
201230-82-2

carbon monoxide

D

benzil
134-81-6

benzil

E

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With oxygenA 100%
B n/a
C n/a
D n/a
E n/a
[(bnpapa)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

[(bnpapa)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

A

phenacyl benzoate
33868-50-7

phenacyl benzoate

B

carbon monoxide
201230-82-2

carbon monoxide

C

[(bnpapa)Ni(O2CPh)]ClO4

[(bnpapa)Ni(O2CPh)]ClO4

D

benzil
134-81-6

benzil

E

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With oxygen In acetonitrile at 20℃;A n/a
B n/a
C 100%
D 12%
E 11 mg
Ca(2-ap)(4-nba)2

Ca(2-ap)(4-nba)2

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogenchloride In water100%
Benzaldoxime
932-90-1

Benzaldoxime

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; vanadia In water at 100℃; for 24h;100%
With 2,2'-azinobis(3-ethylbenzthiazolinesulfonate); Trametes versicolor laccase In acetonitrile at 20℃; pH=5; Green chemistry; Enzymatic reaction;20%
1,2-diphenyl-2-oxoethyl benzoate
1459-20-7

1,2-diphenyl-2-oxoethyl benzoate

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 1h; Reagent/catalyst; Irradiation;100%
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 90℃; for 12h; chemoselective reaction;99%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With poly((divinylbenzene)-0.5 mol-styrenesulfonic acid) In water; toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere;100%
With 10% Pt/activated carbon; oxygen; sodium hydroxide In water at 80℃; for 24h; Green chemistry; chemoselective reaction;82%
cyclohexanone
108-94-1

cyclohexanone

benzaldehyde
100-52-7

benzaldehyde

A

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With oxygen In 1,2-dichloro-ethane at 50℃; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Time;A 100%
B 100%
aniline
62-53-3

aniline

benzoic acid
65-85-0

benzoic acid

N-phenyl benzoyl amide
93-98-1

N-phenyl benzoyl amide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 4h;100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)pyridinium trifluoromethanesulfonate; triethylamine In dichloromethane at 20℃; for 4h;100%
With TEA; 1,2-benzisoxazol-3-yl diphenyl phosphate In various solvent(s) for 2h; Ambient temperature;99%
methanol
67-56-1

methanol

benzoic acid
65-85-0

benzoic acid

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Heating;100%
With sulfuric acid Fischer-Speier esterification method; Reflux;100%
With tetrachloromethane at 20℃; for 72h; UV-irradiation;99%
triethylsilane
617-86-7

triethylsilane

benzoic acid
65-85-0

benzoic acid

triethylsilyl benzoate
1018-20-8

triethylsilyl benzoate

Conditions
ConditionsYield
With indium(III) bromide In dichloromethane-d2 at 20℃;100%
With palladium diacetate In benzene-d6 for 4h; dehydrocoupling reaction; Heating;95%
With zinc(II) chloride In N,N-dimethyl-formamide at 120℃; for 25h;85%
octanol
111-87-5

octanol

benzoic acid
65-85-0

benzoic acid

n-octyl benzoate
94-50-8

n-octyl benzoate

Conditions
ConditionsYield
With bis(5-norbornenyl-2-methyl) azodicarboxylate; polystyrene-supported PPh3 In tetrahydrofuran Esterification; Mitsunobu reaction;100%
With toluene-4-sulfonic acid for 0.05h; Irradiation;97%
With 1-(tert-butyl)-2-(chlorobenzyl) azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 4h; Reagent/catalyst; Mitsunobu Displacement;97.9%
ethanol
64-17-5

ethanol

benzoic acid
65-85-0

benzoic acid

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

Conditions
ConditionsYield
zirconium(IV) oxide at 200℃; var.: 77 deg C, 5 h in liquid-phase;100%
With tetrachloromethane at 20℃; for 72h; UV-irradiation;99%
With alumina methanesulfonic acid at 80℃; for 0.133333h; Microwave irradiation;98%
benzoic acid
65-85-0

benzoic acid

β-naphthol
135-19-3

β-naphthol

2-naphthyl benzoate
93-44-7

2-naphthyl benzoate

Conditions
ConditionsYield
With TiO(acac)2 In xylene for 36h; Heating;100%
Stage #1: benzoic acid With trifluoroacetic anhydride; indium(III) chloride at 20℃;
Stage #2: β-naphthol at 20℃; for 0.166667h;
98%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane for 1h; Ambient temperature;91%
benzoic acid
65-85-0

benzoic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

Conditions
ConditionsYield
With cyanomethylenetributyl-phosphorane In benzene at 100℃; for 24h;100%
With TiO(acac)2 In xylene for 15h; Heating;100%
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h;99%
benzoic acid
65-85-0

benzoic acid

benzoyl chloride
98-88-4

benzoyl chloride

Conditions
ConditionsYield
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Substitution;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Reflux;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 35℃; for 1h;100%
benzoic acid
65-85-0

benzoic acid

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
ConditionsYield
With potassium Sodium; polyethylene oxide In tetrahydrofuran at 0℃; 12 ethylene oxide units/M(+);100%
With hydrogen In water at 100℃; under 15001.5 Torr; for 2h;100%
With C33H49ClNRh; hydrogen In 2,2,2-trifluoroethanol at 20℃; under 51005.1 Torr; for 24h; Autoclave; Molecular sieve;99%
thiophenol
108-98-5

thiophenol

benzoic acid
65-85-0

benzoic acid

phenyl thiobenzoate
884-09-3

phenyl thiobenzoate

Conditions
ConditionsYield
With PPE for 15h; Ambient temperature;100%
With TEA; diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate In various solvent(s) for 2h; Ambient temperature;99%
With dmap; picryl fluoride In acetonitrile for 3h; Ambient temperature;98%
1-amino-2-propene
107-11-9

1-amino-2-propene

benzoic acid
65-85-0

benzoic acid

N-allylbenzamide
10283-95-1

N-allylbenzamide

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 60℃; Inert atmosphere;100%
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;83%
Stage #1: benzoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 1-amino-2-propene In dichloromethane Inert atmosphere;
78%
2-phenylethanol
60-12-8

2-phenylethanol

benzoic acid
65-85-0

benzoic acid

2-Phenylethyl benzoate
94-47-3

2-Phenylethyl benzoate

Conditions
ConditionsYield
With TiO(acac)2 In xylene for 15h; Heating;100%
With iron(III)-acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene for 15h; Inert atmosphere; Reflux;97%
With 4-nitro-diphenylammonium triflate In toluene at 80℃; for 30h;95%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

benzoic acid
65-85-0

benzoic acid

benzoic acid N-hydroxysuccinimide ester
23405-15-4

benzoic acid N-hydroxysuccinimide ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h;97%
With 3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1,-dioxide; triethylamine In dichloromethane -10 deg C -> r.t., overnight;93%
allyl bromide
106-95-6

allyl bromide

benzoic acid
65-85-0

benzoic acid

vinyl benzoate
583-04-0

vinyl benzoate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 0.5h; Heating;100%
With cesium fluoride In acetonitrile for 1.5h; Heating;99%
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 3h;99%
α-bromoacetophenone
70-11-1

α-bromoacetophenone

benzoic acid
65-85-0

benzoic acid

phenacyl benzoate
33868-50-7

phenacyl benzoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile room temperature, 20 min -> reflux, 50 min;100%
With N-ethyl-N,N-diisopropylamine In acetone100%
With potassium carbonate; 1,4-dimethyl-1,2,4-triazolium iodide In acetonitrile at 40℃; for 3h; Schlenk technique;99%
Cholestanol
80-97-7

Cholestanol

benzoic acid
65-85-0

benzoic acid

5α-cholestan-3α-yl benzoate
6030-70-2

5α-cholestan-3α-yl benzoate

Conditions
ConditionsYield
With tributylphosphine; diamide In benzene at 60℃; for 24h; Product distribution; comparison with Mitsunobu reagent; further secondary alcohols and acids;100%
With tributylphosphine; diamide In benzene at 60℃; for 24h;100%
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 60℃; for 24h;81%
With 4-nitro-phenol; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 14h; Ambient temperature;69%
With triphenylphosphine; diethylazodicarboxylate
Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate

Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate

benzoic acid
65-85-0

benzoic acid

α,α-dimethylallyl benzoate
31398-79-5

α,α-dimethylallyl benzoate

Conditions
ConditionsYield
With potassium carbonate; tetrakis(acetonitrile)copper(I)tetrafluoroborate In dichloromethane at 20℃; for 17h;100%
With potassium carbonate; copper(I) bromide In dichloromethane at 20℃;92%

65-85-0Relevant articles and documents

Redox Cascades and Making of a C-C Bond: 1,2-Benzodiazinyl Radicals and a Copper Complex of a Benzodiazine

Mondal, Sandip,Bera, Sachinath,Ghosh, Prasanta

, (2019)

Two 1,2-benzodiazinyl radicals, cinnolinyl radicals by name, were successfully isolated by cascade routes using 1,4-naphthoquinone as a precursor. Reaction of 1,4-naphthoquinone with hydrazine hydrate promotes a (5e + 5H+) redox cascade affording benzo[g]naphtho[1,2-c]cinnolinyl-7,12,14-trione (Cn·) in 69% yields, while the similar reaction with 2-hydrazinopyridine is a (7e + 7H+) oxidative cascade and furnishes N-pyridinecinnolinyl radical (PyCn·). The cascades are composed of C-N and C-C bond making reactions. The neutral even alternate arenes are always diamagnetic; thus, the isolation of Cn· and PyCn· is a breakthrough. The Cn·/Cn- and PyCn·/PyCn- redox couples are reversible, and the reaction of Cn· with [CuI(PPh3)3Cl] in the presence of hydrazine hydrate and Et3N affords a Cn- complex of copper(I), [(Cn-)CuI(PPh3)2] (1). Similar to phenalenyl radical, PyCn· exists in three redox states, PyCn+PyCn·, and PyCn-, in a smaller potential range (-0.30 V to -0.60 V vs Fc+/Fc couple) and can be used as an oxidant as well as a reductant. PyCn· acts as a catalyst for the oxidative cleavages of benzil to benzoic and 2,2′-pyridil to picolinic acids in methanol in the presence of air. The molecular and electronic structures of Cn·PyCn·, and 1·1/2MeOH were confirmed by single crystal X-ray crystallography, EPR spectroscopy, and DFT calculations.

Study of a benzoylperoxy radical in the gas phase: Ultraviolet spectrum and C6H5C(O)O2 + HO2 reaction between 295 and 357 K

Roth,Chakir,Ferhati

, p. 10367 - 10379 (2010)

This work reports the ultraviolet absorption spectrum and the kinetic determinations of the reactions 2C6H5C(O)O2 → products (I) and C6H5C(O)O2 + HO 2 → C6H5C(O)O2H + O2 (IIa), → C6H5C(O)OH + O3 (IIb), → C6H5C(O)O + OH + O2 (IIc). Experiments were performed using a laser photolysis technique coupled with UV-visible absorption detection over the pressure range of 80-120 Torr and the temperature range of 293-357 K. The UV spectrum was determined relative to the known cross section of the ethylperoxy radical C2H5O2 at 250 nm. Kinetic data were obtained by simulating the temporal behavior of the UV absorption at 245-260 nm. At room temperature, the rate constant value of reaction I (cm3 . molecule-1 . s-1) was found to be kI ) (1.5 ± 0.6) × 10-11. The Arrhenius expression for reaction II is (cm3 . molecule-1 . s -1) kII(T) ± (1.10 ± 0.20) × 10 -11 exp(364 ± 200/T). The branching ratios βO3 and βOH, respectively, of reactions IIb and IIc are evaluated at different temperatures; βO3 increases from 0.15 ± 0.05 at room temperature to 0.40 ± 0.05 at 357 K, whereas βOH remains constant at 0.20 ± 0.05. To confirm the mechanism of reaction II, a theoretical study was performed at the B3LYP/6-311++G(2d,pd) level of theory followed by CBS-QB3 energy calculations.

Highly efficient activated carbon loaded TiO2 for photo defluoridation of pentafluorobenzoic acid

Ravichandran,Selvam,Swaminathan

, p. 89 - 96 (2010)

The activated carbon loaded TiO2-P25 catalysts were prepared and characterized by diffuse reflectance spectra (DRS), FT-IR, scanning electron micrograph (SEM), X-ray diffraction (XRD) and BET surface area analysis. The photocatalytic efficiency

Effect of pyridine and tribenzylamine on the hydrolysis kinetics of benzoyl chloride in water-dioxane system

Batiha, Mohammad A.,Chizhova, Elena A.,Batiha, Marwan M.,Al-Makhadmeh, Leema A.,Rawadieh, Saleh,Alqasaimeh, Muawia,Marashli, Abdullah

, p. 1888 - 1890 (2017)

The aim of this paper was to study the effect of tribenzylamine and pyridine on the kinetics of the hydrolysis reaction of benzoyl chloride in water-dioxane solution. The benzoyl chloride and water initial concentrations were 0.005 and 1 mol/L, respectively. While, the initial concentrations of pyridine and tribenzylamine varied in the range of 0.005-0.02 mol/L and 0.007-0.014 mol/L, respectively. It was found that the addition of tribenzylamine to benzoyl chloride hydrolysis reaction has no catalytic effect and hence the rate constant can be calculated using a first-order rate equation. In the presence of pyridine, reaction obeyed second-order rate. The relationship between the reaction rate constant and pyridine initial concentration was found to be linear with a rate constant of 0.752 × 10–3 min–1.

COMPONENTS OF THE GALLS ON THE LEAVES OF PONGAMIA GLABRA: STRUCTURES OF PONGAGALLONE-A AND PONGAGALLONE-B

Gandhidasan, Rathinasamy,Neelakantan, Sthanusubramania,Raman, Pathai Venkateswara,Devaraj, Savithri

, p. 281 - 284 (1987)

The chemical examination of the galls present on the infected leaves of the plant Pongamia glabra has yielded, in addition to a number of known compounds, two new prenylated β-diketones, pongagallone-A and pongagallone-B.Evidence for their structures is presented. Key Word Index--Pongamia glabra; Leguminosae; pongagallone-A; pongagallone-B; β-diketones.

Gardner,Hodgson

, p. 1819 (1909)

Biocompatible Ionic Liquid Based on Curcumin as Fluorescence Probe for Detecting Benzoyl Peroxide without the Interference of H2O2

Zhu, Qiu-Hong,Yuan, Wen-Li,Zhang, Lei,Zhang, Guo-Hao,He, Ling,Tao, Guo-Hong

, (2019)

Accurate estimation of the level of benzoyl peroxide (BPO) is of considerable significance because of its threat to humanity and environment. Several research efforts have been devoted to the detection of BPO by fluorescent method with high sensitivity and selectivity. However, it remains challenging to eliminate the interference of H2O2 due to its similar properties to BPO. In this work, the first demonstration of fluorescent and colorimetric probe for specific detection of BPO without the disturbance of H2O2 was achieved by curcumin-based ionic liquid (CIL) that possesses simple fabrication, good biocompatibility, and low cost. The fluorescence quenches and emission peak blue-shifts once the probe selectively interacts with BPO, whereas the other possible interfering agents, including H2O2, do not have this phenomenon. The probe CIL exhibits prominent sensitivity for BPO sensing and enables the detection limit at levels as ultralow as 10 nM. The local detection of BPO in practical samples is realized by visualization using a portable device derived from CIL-based liquid atomizer.

Prenylated benzoylphloroglucinols and xanthones from the leaves of garcinia oblongifolia with antienteroviral activity

Zhang, Hong,Tao, Ling,Fu, Wen-Wei,Liang, Shuang,Yang, Yi-Fu,Yuan, Qing-Hong,Yang, Da-Jian,Lu, Ai-Ping,Xu, Hong-Xi

, p. 1037 - 1046 (2014)

An acetone extract of the leaves of Garcinia oblongifolia showed antiviral activity against enterovirus 71 (EV71) using a cytopathic effect inhibition assay. Bioassay-guided fractionation yielded 12 new prenylated benzoylphloroglucinols, oblongifolins J-U (1-12), and five known compounds. The structures of 1-12 were elucidated by spectroscopic analysis including 1D- and 2D-NMR and mass spectrometry methods. The absolute configurations were determined by a combination of a Mosher ester procedure carried out in NMR tubes and ECD calculations. Compared to ribavirin (IC50 253.1 μM), compounds 1, 4, and 13 exhibited significant anti-EV71 activity in vitro, with IC50 values of 31.1, 16.1, and 12.2 μM, respectively. In addition, the selectivity indices of these compounds were 1.5, 2.4, and 3.0 in African green monkey kidney (Vero) cells, respectively.

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Fokin,A.V. et al.

, (1975)

-

Kinetics and mechanism of oxidation of benzohydrazide by bromate catalyzed by vanadium(IV) in aqueous acidic medium

Shewale,Phadkule,Gokavi

, p. 151 - 159 (2008)

The reaction between benzohydrazide and potassium bromate catalyzed by vanadium(IV) was studied under pseudo-first-order condition keeping large excess of hydrazide concentration over that of the oxidant. The initiation of the reaction occurs through oxidation of the catalyst vanadium(IV), VO2+, to vanadium(V), VO2+, which then reacts with hydrazide to give N,N′-diacylhydrazine and benzoic acid as the products. The order in [H+] is found to be two, and its effect is due to protonation and hydrolysis of oxidized form of the catalyst to form HVO3. The oxidized form of the catalyst, VO2+, forms a complex with the protonated hydrazide as evidenced by the occurrence of absorption maxima at 390 nm. The rate of the reaction remains unaffected by the increase in the ionic strength. The activation parameters were determined, and data support the mechanism. The detailed mechanism and the rate equation are proposed for the reaction.

ELECTRON-TRANSFER MEDIATED PHOTOOXYGENATION OF BIPHENYL AND ITS DERIVATIVES IN THE PRESENCE OF Mg(ClO4)2

Mizuno, Kazuhiko,Ichinose, Nobuyuki,Tamai, Toshiyuki,Otsuji, Yoshio

, p. 5823 - 5826 (1985)

The 9,10-dicyanoanthracene-sensitized photooxygenation of biphenyl and its derivatives in the presence of Mg(ClO4)2 in acetonitrile brought about the oxidative cleavage of benzene nucleus to give benzoic acid and its derivatives.

-

Briner,Lardon

, p. 1062,1066 (1936)

-

Catalytic and inhibitory effects of β-cyclodextrin on the hydrolysis of benzoic anhydride

Brandao, Tiago A.S.,Dal Magro, Jacir,Chiaradia, Louise D.,Da Graca Nascimento, Maria,Nome, Faruk,Tato, Jose V.,Yunes, Rosendo A.

, p. 370 - 375 (2004)

The hydrolysis of benzoic anhydride (Bz2O) in the presence of β-cyclodextrin (β-CD) was studied in aqueous solution as a function of pH, temperature and ionic strength, at 25°C. The experimental rate constant versus pH profiles show that, in the region of spontaneous water reaction (pH 3.0-6.5), β-CD inhibits the reaction and the isotope effect (k H2O/kD2O = 4.7) indicates that the rate determining step of the reaction corresponds to the water-catalyzed nucleophilic attack of water on the carbonyl group of Bz2O. Conversely, whereas inhibition is observed at pH 6.0, catalysis of the hydroxide ion reaction is observed at pH 8.0 and it is found that the activation entropy is responsible for the catalytic phenomena in the basic hydrolysis of benzoic anhydride. Copyright 2004 John Wiley & Sons, Ltd.

Hydrolysis of several substituted methyl benzoates in the aqueous solution

Steinberg,Lena

, p. 965 - 969 (1995)

The hydrolysis of several ring substituted methyl benzoates was investigated in aqueous solution over a pH range of 3-10. Both the pH dependence (at pH5) and the variation of hydrolysis rates with ring substitution are consistent with a mechanism involving the addition of hydroxide ion to the ester carbonyl group. Extrapolation of the rate data to a pH and temperature that would be consistent with soil and groundwater (pH 8, 10 degrees C) indicate that these esters could have hydrolysis half lives from several months to several years in the environment. (Authors)

Novel oxo-peroxo molybdenum(VI) complexes incorporating 8-quinolinol: Synthesis, structure and catalytic uses in the environmentally benign and cost-effective oxidation method of methyl benzenes: Ar(CH3), (n = 1, 2)

Bandyopadhyay, Ratna,Biswas, Sudeb,Guha, Subhadra,Mukherjee, Alok K.,Bhattacharyya, Ramgopal

, p. 1627 - 1628 (1999)

A hitherto unknown distorted pentagonal bipyramidal complex, [MoO(O2)(QO)2], very efficiently catalyses homogeneous liquid phase oxidation of methylbenzenes, viz. toluene and o- and p-xylenes to benzoic acid, phthalic acid and p-toluic acid respectively, using H2O2 and O2 as oxidants.

-

Ogata et al.

, p. 2707 (1952)

-

-

Williams,Whitaker

, p. 2562,2564 (1968)

-

-

Briner,Biedermann

, p. 213,215 (1933)

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Kharasch, M. S.,May, E. M.,Mayo, F. R.

, p. 175 - 192 (1938)

A DITERPENE FROM EUPHORBIA MADDENI

Sahai, R.,Rastogi, R. P.,Jakupovic, J.,Bohlmann, F.

, p. 1665 - 1668 (1981)

Key Word Index - Euphorbia maddeni; Euphorbiaceae; euphornin; jatrophone diterpene. From the anticancer-active CHCl3 extract of the plant Euphorbia maddeni, a polyacylated diterpene of jatrophone type, euphornin, has been isolated and its structure elucidated by physico-chemical methods.

Heavy-Atom Isotope Effects on the Acid-Catalyzed Hydrolysis of Methyl Benzoate

Marlier, John F.,O'Leary, Marion H.

, p. 2175 - 2177 (1981)

-

-

Briner,Papazian

, p. 497,503 (1940)

-

-

Nystrom et al.,zit. bei Crompton,Woodruff

, p. 44,46 (1950)

-

-

Ross et al.

, p. 1018 (1969)

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Carboxylic acids from methyl aryl ketones by means of a new composite aerobic oxidation process

Bj?rsvik, Hans-René,Liguori, Lucia,Rodríguez González, Raquel,Vedia Merinero, José Angel

, p. 4985 - 4987 (2002)

A new aerobic oxidation method for conversion of methyl aryl ketones to the corresponding benzoic acids is presented. The method is cheap and environmentally friendly, which also makes it suitable for large scale industrial use. The method affords a yield of >75% with an almost 100% selectivity. Experiments have shown that the process operates following two mechanistic pathways, namely by base-catalysed autoxidation and by single electron transfer processes.

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

Niu, Kaikai,Shi, Xiaodi,Ding, Ling,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin

, (2021/12/13)

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.

Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water

Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David

, (2021/11/30)

Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.

Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading

Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui

, (2021/12/13)

Acceptorless dehydrogenative coupling (ADC) of alcohols and water/hydroxides is an emergent and graceful approach to produce carboxylic acids. Therefore, it is of high demand to develop active and practical catalysts/catalytic systems for this attractive transformation. Herein, we designed and fabricated a series of cyclometallated N-heterocyclic carbene-Ru (NHC-Ru) complexes via ligand tuning of [Ru-1], the superior complex in our previous work. Gratifyingly, gram-scale synthesis of carboxylic acids was efficiently enabled at an ultralow Ru loading (62.5 ppm) in open air. Moreover, effects of distinct ancillary NHC ligands and other parameters on this catalytic process were thoroughly studied, while further systematic studies were carried out to provide rationales for the activity trend of [Ru-1]-[Ru-7]. Finally, determination of quantitative green metrics illustrated that the present work exhibited superiority over representative literature reports. Hopefully, this study could provide valuable input for researchers who are engaging in metal-catalyzed ADC reactions.

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