Quick Search
Carboxyacetic acid, also known as propanedioic acid, is a dicarboxylic acid with structure CH2(COOH)2.
Carboxyacetic acid have three kinds of crystal forms, of which two are triclinic, and one is monoclinic.
That crystallized from ethanol is white triclinic crystals.
CAS: 141-82-2
MF: C3H4O4
MW: 104.06
EINECS: 205-503-0
Synonyms
MALONIC ACID, 99%MALONIC ACID, 99%MALONIC ACID, 99%MALONIC ACID, 99%;Valproic Acid Impurity 2 (Malonic Acid);Malonic acid 141-82-2;141-82-2 Malonic acid 1,3-Propanedioic acid;Sodium Valproate Impurity 24;Malonic acid, AR,99.5%;Malonate, AR,99.5%;Malonic acid anhydrous, ;free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%;malonic acid;propanedioic acid;141-82-2;Dicarboxymethane;Carboxyacetic acid;Methanedicarboxylic acid;malonate;Kyselina malonova;USAF EK-695;1,3-Propanedioic acid;Kyselina malonova [Czech];NSC 8124;MFCD00002707;UNII-9KX7ZMG0MK;9KX7ZMG0MK;AI3-15375;H2malo;EINECS 205-503-0;BRN 1751370;Methanedicarbonic acid;CHEBI:30794;Thallium malonate;HOOC-CH2-COOH;NSC8124;Propane-1,3-dioic acid;Malonicacid;alpha,omega-Dicarboxylic acid;DTXSID7021659;HSDB 8437;NSC8124;4-02-00-01874 (Beilstein Handbook Reference);1,3-Propanoic acid,Malonic acid-13C3;PROPANEDIOLIC ACID;2fah;MLI;Malonic acid, 99%;Malonic acid (8CI);1o4m;63524-05-0;Malonate dicarboxylic acid;Malonic acid, 99.5%;Propanedioic acid (9CI);SCHEMBL336;WLN: QV1VQ;MALONIC ACID [MI];CH2(COOH)2;CHEMBL7942;DTXCID401659;SCHEMBL1471092;BDBM14673;Propanedioic acid dithallium salt;Malonic acid, analytical standard;BCP05571;STR00614;Tox21_200534;AC8295;LMFA01170041;s3029;STL194278;Malonic acid, ReagentPlus(R), 99%;AKOS000119034;CS-W019962;DB02175;FM32432;PROPANEDIOIC ACID MALONIC ACID;NCGC00248681-01;NCGC00258088-01;BP-11453;CAS-141-82-2;SY001875;DB-081008;DB-088240;Malonic acid, SAJ first grade, >=99.0%;M0028;NS00013842;EN300-18457;Malonic acid, Vetec(TM) reagent grade, 98%;C00383;C02028;C04025;Q421972;Z57965450;F1908-0177;Malonic acid, certified reference material, TraceCERT(R);592A9849-68C3-4635-AA3D-CBC44965EA3A;Malonic acid, sublimed grade, >=99.95% trace metals basis;DICARBOXYLIC ACID C3; PROPANEDIOLIC ACID; METHANEDICARBOXYLIC ACID;InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7;Malonic acid, anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%;205-503-0;87205-08-1;LML
Carboxyacetic acid decomposes to acetic acid and carbon dioxide at 140℃.
Carboxyacetic acid does not decompose at 1.067×103~1.333×103Pa vacuum, but directly sublimates.
The ionised form of Carboxyacetic acidd, as well as its esters and salts, are known as malonates.
For example, diethyl malonate is malonic acid's ethyl ester.
The name originates from Latin malum, meaning apple.
Carboxyacetic acid is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.
Carboxyacetic acid has a role as a human metabolite.
Carboxyacetic acid is a conjugate acid of a malonate(1-).
Carboxyacetic acid is a potent inducer of biocompatible polymers and sodium salts.
Carboxyacetic acid is an acidic chemical compound that belongs to the group of malonates.
Carboxyacetic acid has been shown to induce neuronal death in model systems, but also has a protective effect on human serum fibroblasts.
The reaction solution containing malonic acid and sodium bicarbonate generates malonate, which can be used as a precursor for energy metabolism and cell signaling.
Carboxyacetic acid is a dicarboxylic acid with structure CH2(COOH)2.
The ionized form of malonic acid, as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Carboxyacetic acid's diethyl ester.
The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
Carboxyacetic acid, also known as Propanedioic Acid, is a dicarboxylic acid that plays important roles in biochemical processes.
In pharmaceutical manufacturing, Carboxyacetic acid serves as an intermediate in the biosynthesis of compounds such as barbiturates.
In addition, Carboxyacetic acid is used for peptization in obtaining highly dispersed system, it is used in the manufacturing of various pharmaceuticals too.
Carboxyacetic acid appears as a white crystalline powder.
Carboxyacetic acid is a dicarboxylic acid with structure CH2(COOH)2.
The ionized form of Carboxyacetic acid, as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Carboxyacetic acid's diethyl ester.
The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
Carboxyacetic acid appears as white crystals or crystalline powder.
Sublimes in vacuum.
Carboxyacetic acid appears as white crystals or crystalline powder.
Carboxyacetic acid is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.
Carboxyacetic acid has a role as a human metabolite.
Carboxyacetic acid is an alpha,omega-dicarboxylic acid and a lipid.
Carboxyacetic acid is a conjugate acid of a malonate(1-).
History
Carboxyacetic acid is a naturally occurring substance found in many fruits and vegetables.
There is a suggestion that citrus fruits produced in organic farming contain higher levels of Carboxyacetic acid than fruits produced in conventional agriculture.
Carboxyacetic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid.
Hermann Kolbe and Hugo Müller independently discovered how to synthesize malonic acid from propionic acid, and decided to publish their results back-to-back in the Chemical Society journal in 1864.
This led to priority dispute with Hans Hübner and Maxwell Simpson who had independently published preliminary results on related reactions.
Reactions
Carboxyacetic acid reacts as a typical carboxylic acid forming amide, ester, and chloride derivatives.
Carboxyacetic acid can be used as an intermediate to mono-ester or amide derivatives, while malonyl chloride is most useful to obtain diesters or diamides.
In a well-known reaction, malonic acid condenses with urea to form barbituric acid.
Malonic acid may also be condensed with acetone to form Meldrum's acid, a versatile intermediate in further transformations.
The esters of malonic acid are also used as a −CH2COOH synthon in the malonic ester synthesis.
Carboxyacetic acid is a precursor to specialty polyesters.
Carboxyacetic acid can be converted into 1,3-propanediol for use in polyesters and polymers (whose usefulness is unclear though).
Carboxyacetic acid can also be a component in alkyd resins, which are used in a number of coatings applications for protecting against damage caused by UV light, oxidation, and corrosion.
One application of Carboxyacetic acid is in the coatings industry as a crosslinker for low-temperature cure powder coatings, which are becoming increasingly valuable for heat sensitive substrates and a desire to speed up the coatings process.
The global coatings market for automobiles was estimated to be $18.59 billion in 2014 with projected combined annual growth rate of 5.1% through 2022.
Carboxyacetic acid is used in a number of manufacturing processes as a high value specialty chemical including the electronics industry, flavors and fragrances industry, specialty solvents, polymer crosslinking, and pharmaceutical industry.
In 2004, annual global production of malonic acid and related diesters was over 20,000 metric tons.
Potential growth of these markets could result from advances in industrial biotechnology that seeks to displace petroleum-based chemicals in industrial applications.
In 2004, malonic acid was listed by the US Department of Energy as one of the top 30 chemicals to be produced from biomass.
In food and drug applications, malonic acid can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.
Carboxyacetic acid is used as a building block chemical to produce numerous valuable compounds, including the flavor and fragrance compounds gamma-nonalactone, cinnamic acid, and the pharmaceutical compound valproate.
Carboxyacetic acid has been used to cross-link corn and potato starches to produce a biodegradable thermoplastic; the process is performed in water using non-toxic catalysts.
Starch-based polymers comprised 38% of the global biodegradable polymers market in 2014 with food packaging, foam packaging, and compost bags as the largest end-use segments.
Eastman Kodak company and others use malonic acid and derivatives as a surgical adhesive.
Carboxyacetic acid Chemical Properties
Melting point: 132-135 °C (dec.) (lit.)
Boiling point: 140℃（decomposition）
Density: 1.619 g/cm3 at 25 °C
Vapor pressure: 0-0.2Pa at 25℃
Refractive index: 1.4780
Fp: 157°C
Storage temp.: Sealed in dry,Room Temperature
Solubility 1 M NaOH: soluble100mg/mL, clear to slightly hazy, colorless to faintly yellow
Form: Liquid
pka: 2.83(at 25℃)
Color: White
PH: 3.17(1 mM solution);2.5(10 mM solution);1.94(100 mM solution)
Water Solubility: 1400 g/L (20 ºC)
Merck: 14,5710
BRN: 1751370
Stability: Stable. Incompatible with oxidizing agents, reducing agents, bases.
InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N
LogP: -0.81
CAS DataBase Reference: 141-82-2(CAS DataBase Reference)
NIST Chemistry Reference: Carboxyacetic acid(141-82-2)
EPA Substance Registry System: Carboxyacetic acid (141-82-2)
Carboxyacetic acid is a white crystalline solid that decomposes at approximately 135°C.
Carboxyacetic acid has high solubility in water and oxygenated solvents and exhibits greater acidity than acetic acid, which has a pK value of 4.75.
The pKa values for the loss of its first and second protons are 2.83 and 5.69, respectively. Carboxyacetic acid is slightly soluble in pyridine.
Carboxyacetic acid can decompose to formic acid and carbon dioxide in case of potassium permanganate.
Since that Carboxyacetic acid generates carbon dioxide and water after heated without pollution problems, Carboxyacetic acid can be directly used as aluminum surface treatment agent.
Uses
Carboxyacetic acid is used as an intermediate in the manufacture of barbiturates and other pharmaceuticals.
Carboxyacetic acid is a component used as a stabilizer in many high-end cosmetic and pharmaceutical products.
Carboxyacetic acid is also used as building block in chemical synthesis, specifically to introduce the molecular group -CH2-COOH.
Carboxyacetic acid is used for the introduction of an acetic acid moiety under mild conditions by Knoevenagel condensation and subsequent decarboxylation.
Malonic acid is acts as a building block in organic synthesis.
Carboxyacetic acid is also useful as a precursor for polyesters and alkyd resins, which is used in coating applications, thereby protecting against UV light, corrosion and oxidation.
Carboxyacetic acid acts as a cross linker in the coating industry and surgical adhesive.
Carboxyacetic acid finds application in the production of specialty chemicals, flavors and fragrances, polymer cross linkers and pharmaceuticals.
Biotechnological Applications
The calcium salt of Carboxyacetic acid occurs in high concentrations in beetroot.
Carboxyacetic acid exists in its normal state as white crystals.
Carboxyacetic acid is the classic example of a competitive inhibitor:
Carboxyacetic acid acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.
Preparation
Carboxyacetic acid is usually produced from chloroacetic acid.
Reaction: The chloroacetic acid is added to the reaction kettle by adding sodium carbonate aqueous solution to generate sodium chloroacetate aqueous solution, and then 30% sodium cyanide solution is slowly added dropwise, and the reaction is carried out at a predetermined temperature to generate sodium cyanoacetate.
After the cyanation reaction is completed, add sodium hydroxide for heating and hydrolysis to generate sodium malonate solution, concentrate, then dropwise add sulfuric acid for acidification to generate malonic acid, filter and dry to obtain the product.
This method often does not produce a pure enough product or the pure product has an extremely low yield.
Industrially, Carboxyacetic acid is also produced by hydrolyzing dimethyl malonate or diethyl malonate.
This manufacturing method is able to bring about a higher yield and purity, but the organic synthesis of Carboxyacetic acid through these processes is extremely costly and environmentally hazardous.
Reactions
In a well - known reaction, Carboxyacetic acid condenses with urea to form barbituric acid.
Carboxyacetic acid is also frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum's acid.
The esters of Carboxyacetic acid are also used as a - CH2COOH synthon in the malonic ester synthesis.
Biological Functions
Carboxyacetic acid is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.
Carboxyacetic acid binds to the active site of the enzyme without reacting, competing with the usual substrate succinate but lacking the CH2CH2 group required for dehydrogenation.
This observation was used to deduce the structure of the active site in succinate dehydrogenase.
Reactivity Profile
Carboxyacetic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them.
They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat.
Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of carboxylic acids is therefore less than 7.0.
Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.
Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Carboxyacetic acid to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids.
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents.
These reactions generate heat.
A wide variety of products is possible.
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions Malonic acid is incompatible with strong oxidizers.
Carboxyacetic acid is also incompatible with bases and reducing agents.
