582-25-2 Usage
Description
Potassium benzoate is the potassium salt of benzoate. It is mostly used for food preservation for inhibiting the growth of mold, yeast and bacteria since it can create low pH condition after entering into the cells to suppress the anaerobic fermentation of glucose. It can also be used in the whistle in many fireworks. In analytic chemistry, it can be used as eluents for ion chromatography to increase the detector response.
Chemical Properties
Different sources of media describe the Chemical Properties of 582-25-2 differently. You can refer to the following data:
1. Potassium benzoate occurs as a slightly hygroscopic, white, odorless
or nearly odorless crystalline powder or granules. Aqueous
solutions are slightly alkaline and have a sweetish astringent taste.
2. Potassium benzoate ( E212 ) , the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacteria. It works best in low-pH products, below 4.5, where it exists as benzoic acid. Acidic foods and beverages such as fruit juice (citric acid), sparkling drinks (carbonic acid), soft drinks (phosphoric acid), and pickles (vinegar) may be preserved with potassium benzoate. It is approved for use in most countries including Canada, the U.S., and the EU, where it is designated by the E number E212. In the EU, it is not recommended for consumption by children.
Uses
Different sources of media describe the Uses of 582-25-2 differently. You can refer to the following data:
1. Potassium Benzoate is manufactured primarily for food and beverage use. It is a chemical preservative, which in very low concentrations inhibits the activity of the microorganisms. It is used in carbonated beverages. The shelf life of un-pasteurized cider can be greatly extended by adding potassium benzoate. It is also used as the whistle in many fireworks.
2. Pharmaceutic aid (preservative).
Production Methods
Potassium benzoate is prepared from the acid–base reaction
between benzoic acid and potassium hydroxide.
Flammability and Explosibility
Notclassified
Pharmaceutical Applications
Potassium benzoate is predominantly used as an antimicrobial
preservative in a wide range of beverages, foods and some
pharmaceutical formulations. Preservative efficacy increases with
decreasing pH; it is most effective at pH 4.5 or below. However, at
low pH undissociated benzoic acid may produce a slight though
discernible taste in food products.
Increasingly, potassium benzoate is used as an alternative to
sodium benzoate in applications where a low sodium content is
desirable.
Therapeutically, potassium benzoate has also been used in the
management of hypokalemia.
Safety Profile
Combustible when
exposed to heat or flame. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Safety
Different sources of media describe the Safety of 582-25-2 differently. You can refer to the following data:
1. Potassium benzoate was recently described by the Food Commission, who campaign for 'safer, healthier food in the UK', as "mildly irritant to the skin, eyes and mucous membranes". Cats have a significantly lower tolerance to benzoic acid and its salts than rats and mice.
2. Potassium benzoate is widely used in food products and is generally
regarded as a nontoxic and nonirritant material. However, people
with a history of allergies may show allergic reactions when exposed
to potassium benzoate. Ingestion is inadvisable for asthmatics.
Higher concentrations of potassium benzoate have been reported to
cause irritation to mucous membranes.
The WHO acceptable daily intake of total benzoates including
potassium benzoate, calculated as benzoic acid, has been estimated
at up to 5 mg/kg of body-weight.
Synthesis
One very common way to make potassium benzoate is by oxidizing toluene. Another way to synthesize potassium benzoate in the lab setting is by reacting methyl benzoate with potassium thio acetate.
storage
Potassium benzoate is stable at room temperature under normal
storage conditions. Since it is slightly hygroscopic, potassium
benzoate should be stored in sealed containers. Exposure to
conditions of high humidity and elevated temperatures should be
avoided.
Purification Methods
Potassium benzoate [582-25-2] M 160.2. Crystallise it from water (1mL/g) between 100o and 0o. [Beilstein 9 III 375, 9 IV 279.]
Mechanism of food preservation
The mechanism of food preservation begins with the absorption of benzoic acid into the cell. If the intracellular pH changes to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95 %.
Spectra
Carbon 13 NMR The carbon NMR shows 5 unique peaks. There are four peaks between 130 - 140 ppm from the carbons in the benzene ring. There is an additional carbon peak around 178 ppm representing the carbon from the carbonyl. Infrared spectrum The following are the main peaks in the IR spectrum. 1610: C=O from carbonyl 1580: C=C from benzene ring.
Incompatibilities
Potassium benzoate is incompatible with strong acids and strong
oxidizing agents.
Regulatory Status
GRAS listed. Accepted as a food additive in Europe. Included in the
Canadian List of Acceptable Non-medicinal Ingredients.
References
Gjerde, Douglas T., and J. S. Fritz. "Sodium and potassium benzoate and benzoic acid as eluents for ion chromatography." Analytical Chemistry 53.14(1981):2324-2327.
Zengin, N., et al. "The evaluation of the genotoxicity of two food preservatives: Sodium benzoate and potassium benzoate." Food & Chemical Toxicology An International Journal Published for the British Industrial Biological Research Association 49.4(2011):763-9.
Zeb, Alam, et al. "Grape juice preservation with benzoate and sorbate. " Advances in Food Sciences (2009).
Marietta, Michael S. "Fireworks artillery shell." US, US6912958. 2005.
Check Digit Verification of cas no
The CAS Registry Mumber 582-25-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 2 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 582-25:
(5*5)+(4*8)+(3*2)+(2*2)+(1*5)=72
72 % 10 = 2
So 582-25-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2.K/c8-7(9)6-4-2-1-3-5-6;/h1-5H,(H,8,9);/q;+1/p-1
582-25-2Relevant articles and documents
Significant effect of base on the improvement of selectivity in the hydrogenation of benzoic acid over NiZrB amorphous alloy supported on γ-Al2O3
Wen, Xin,Cao, Yingying,Qiao, Xianliang,Niu, Libo,Huo, Li,Bai, Guoyi
, p. 3281 - 3287 (2015)
This study presents a facile way to improve the selectivity for cyclohexanecarboxylic acid by adding a base in the hydrogenation of benzoic acid over a non-noble metal NiZrB amorphous alloy supported on γ-Al2O3. It is found that alkali metal carbonates exhibit an excellent selectivity improvement from 50.3% to a range of 93.5-95.7%, with the conversion of benzoic acid higher than 92.3%. Even a very small amount of K2CO3 (1 mol% benzoic acid) was efficient for improving the selectivity for cyclohexanecarboxylic acid. In addition, a lower reaction temperature was beneficial to the improvement of selectivity. Based on the results of temperature programmed desorption of NH3 and inductively coupled plasma analysis, the improvement of selectivity in the presence of a base was attributed to the neutralization of the acidic sites on the surface of the catalyst by the in situ generated potassium benzoate, inhibiting the hydrodeoxygenation of carbonyl and resulting in a high selectivity for cyclohexanecarboxylic acid.
An Anionic, Chelating C(sp3)/NHC ligand from the Combination of an N-heterobicyclic Carbene and Barbituric Heterocycle
Benaissa, Idir,Gajda, Katarzyna,Vendier, Laure,Lugan, No?l,Kajetanowicz, Anna,Grela, Karol,Michelet, Véronique,César, Vincent,Bastin, Stéphanie
, p. 3223 - 3234 (2021/09/30)
The coordination chemistry of the anionic NHC1-based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) platform substituted at the C5 position by an anionic barbituric heterocycle was studied with d6(Ru(II), Mn(I)) and d8(Pd(II), Rh(I), Ir(I), Au(III)) transition-metal centers. While the anionic barbituric heterocycle is planar in the zwitterionic NHC precursor 1·H, NMR spectroscopic analyses supplemented by X-ray diffraction studies evidenced the chelating behavior of ligand 1-through the carbenic and the malonic carbon atoms in all of the complexes, resulting from a deformation of the lateral barbituric heterocycle. The complexes were obtained by reaction of the free carbene with the appropriate metal precursor, except for the Au(III) complex 10, which was obtained by oxidation of the antecedent gold(I) complex [AuCl(1)]?with PhICl2as an external oxidant. During the course of the process, the kinetic gold(I) intermediate 9 resulting from the oxidation of the malonic carbon of the barbituric moiety was isolated upon crystallization from the reaction mixture. The νCOstretching frequencies recorded for complex [Rh(1)(CO)2] (5) demonstrated the strong donating character of the malonate-C(sp3)/NHC ligand 1-. The ruthenium complex [Ru(1)Cl(p-cymene)] (11) was implemented as a precatalyst in the dehydrogenative synthesis of carboxylic acid derivatives from primary alcohols and exhibited high activities at low catalyst loadings (25-250 ppm) and a large tolerance toward functional groups.
A Diaminopropane Diolefin Ru(0) Complex Catalyzes Hydrogenation and Dehydrogenation Reactions
Casas, Fernando,Trincado, Monica,Rodriguez-Lugo, Rafael,Baneerje, Dipshikha,Grützmacher, Hansj?rg
, p. 5241 - 5251 (2019/11/16)
New ruthenium (0) complexes with a cooperative diolefin diaminopropane (DAP) or the dehydrogenated iminopropenamide ligand (IPA) were synthesized for comparison with their diaminoethane (DAE)/ diazadiene (DAD) ruthenium analogues. These DAP/IPA complexes are efficient catalysts in dehydrogenation reactions of alkaline aqueous methanol which proceeds under mild conditions (T=70 °C) and of higher alcohols, forming the corresponding carbonate and carboxylates, respectively. The scope of the reaction includes an example of a 1,2-diol as model for biomass derived alcohols. Their catalytic applications are extended to the atom-efficient dehydrogenative coupling of alcohols and amines to amides. The reaction proceeds without any additives and is applicable to the synthesis of formamides from methanol. Moreover, DAP/IPA complexes catalyze the hydrogenation of a series of esters, lactone, ketone, activated olefin, aldehyde and imine substrates. The diaminopropane Ru catalyst exhibits higher activity compared to the dehydrogenated β-ketiminate (IPA) and previously studied DAD/DAE based catalysts. We present studies on their stoichiometric reactivity with relevance to their possible catalytic mechanisms and the isolation and full characterization of key reaction intermediates.
Mechanistic investigation of imine formation in ruthenium-catalyzed N-alkylation of amines with alcohols
Yu, Xiaojun,Li, Yaqiu,Fu, Haiyan,Zheng, Xueli,Chen, Hua,Li, Ruixiang
, (2018/02/09)
Imines are observed frequently in ruthenium-catalyzed N-alkylation of amines with alcohols. Herein, nitrogen–phosphine functionalized carbene ligands were developed and used in ruthenium-catalyzed N-alkylation to explore the mechanism of imine formation. The results showed that strongly electron-donating ligands were beneficial for imine formation and alcohol dehydrogenation to generate acid. In addition, with an increase of electron density of nitrogen atom in substituted amines, the yield of imines in N-alkylation was improved. At the same time, with electron-rich imines as substrates, the transfer hydrogenation of imines became difficult. It is suggested that strongly electron-donating ligands and substrates caused an increase of electron density on the ruthenium center, which resulted in the elimination of hydrogen atoms in active species [LRuH2] as hydrogen gas rather than transfer onto the imine coordinated with the ruthenium center.
