Basic information Dibasic acid Chemical Properties Uses Preparation Safety Supplier Related
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Malonic acid

Basic information Dibasic acid Chemical Properties Uses Preparation Safety Supplier Related

Malonic acid Basic information

Product Name:
Malonic acid
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%
CAS:
141-82-2
MF:
C3H4O4
MW:
104.06
EINECS:
205-503-0
Product Categories:
  • Acids
  • Electronic Chemicals
  • Materials Science
  • Micro &amp
  • Micro/NanoElectronics
  • Nanoelectronics
  • Intermediates
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • alpha,omega-Alkanedicarboxylic Acids
  • alpha,omega-Bifunctional Alkanes
  • Monofunctional & alpha,omega-Bifunctional Alkanes
  • New Products for Materials Research and Engineering
  • 141-82-2
Mol File:
141-82-2.mol
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Malonic 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
Flash point:
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
Malonic acid(141-82-2)
EPA Substance Registry System
Propanedioic acid (141-82-2)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
20/22-41-36/37/38-22
Safety Statements 
26-36/39-37/39-36
RIDADR 
3261
WGK Germany 
1
RTECS 
OO0175000
TSCA 
Yes
PackingGroup 
III
HS Code 
29171910
Hazardous Substances Data
141-82-2(Hazardous Substances Data)

MSDS

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Malonic acid Usage And Synthesis

Dibasic acid

Malonic acid is a dibasic acid. It have three kinds of crystal forms, of which two are triclinic, and one is monoclinic. That crystallized from ethanol is white triclinic crystals. Its relative molecular mass is 104.06. The relative density is 1.631 (15 ℃). Melting point is 135.6℃. It decomposes to acetic acid and carbon dioxide at 140℃. It does not decompose at 1.067×103~1.333×103Pa vacuum, but directly sublimates. It is not soluble in benzene. It is soluble in water, and the solubility is respectively 61.1 (0 ℃), 73.5 (20 ℃), 92.6 (50 ℃) in water, and 57 (20 ℃)in ethanol, 5.7 (20 ℃) in diethyl ether. It is slightly soluble in pyridine. It can decompose to formic acid and carbon dioxide in case of potassium permanganate.
Since that malonic acid generates carbon dioxide and water after heated without pollution problems, it can be directly used as aluminum surface treatment agent; it is also the raw material in the production of pesticides fungicides Fujione, herbicides Alloxydim; malonic acid is used to prepare diuretic sulfinpyrazone medicine, anti-inflammatory drug phenylbutazone paraben, sedatives bromomethyl Jacinto goods in pharmaceutical industries. In addition, malonic acid and its esters are widely used as pharmaceutical intermediates, such as preparing barbiturates, vitamins B1 and B6, etc. Esters of malonic acid are commonly used in organic synthesis. It also can be used as binding agent, perfum, resin additive, electroplating polishing agent, welding flux and so on.
The above information is edited by the chemicalbook of Ge Qian.

Chemical Properties

White crystals. It dissolves easily in water. And it is soluble in alcohol, ether and pyridine.

Uses

Malonic acid is used in a diverse group of industries. It is used as a precursor in specialty polyesters and polymers, as it can be converted to 1,3 propanediol.Malonic acid is also a component in alkyd resins. These are utilized in different coating applications to protect against UV light, oxidation, and corrosion damage. Malonic acid also has applications as a more high value, specialty chemical in some industries. These include the electronic, flavors and fragrance, specialty solvents, polymer crosslinking, and pharmaceutical industries. Specifically, in food and drugs, malonic acid is used to control acidity by either acting as an excipient in pharmaceutical drug formulations or as a natural preservative additive for foods. It is used to synthesize gamma-nonalactone and cinnamic acid in the flavor and fragrance industry and valproate in the pharmaceutical industry.

Preparation

The preparation method of malonic acid: Chloroacetic acid is used as raw material in Laboratories. It is neutralized by NaOH or Na2CO3 to generate chloroacetic acid sodium salt. The sodium salt reacts with KCN (or NaCN) to yield α-cyano sodium acetate. And then malonic acid can be prepared after alkaline hydrolysis, calcium replacement and acidification. Chemical reaction equation is as follows:

Description

Malonic acid (IUPAC systematic name: propanedioic 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 malonic acid's diethyl ester. The name originates from the Greek word (malon) meaning 'apple'.

Chemical Properties

Malonic acid is a diprotic acid. It is a white crystalline solid with a decomposition point of ≈135 °C. It is highly soluble in water and oxygenated solvents. It is a stronger acid than acetic acid(pK=4.75). The pKa for the loss of the first proton is 2.83; the pKa for the loss of the second proton is 5.69.

Uses

Malonic acid is used as an intermediate in the manufacture of barbiturates and other pharmaceuticals. It is a component used as a stabilizer in many high-end cosmetic and pharmaceutical products. Malonic acid is also used as building block in chemical synthesis, specifically to introduce the molecular group -CH2-COOH. It is used for the introduction of an acetic acid moiety under mild conditions by Knoevenagel condensation and subsequent decarboxylation.

Application

Malonic acid is acts as a building block in organic synthesis. It 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. It acts as a cross linker in the coating industry and surgical adhesive. It finds application in the production of specialty chemicals, flavors and fragrances, polymer cross linkers and pharmaceuticals.

Definition

ChEBI: Malonic acid is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group. It has a role as a human metabolite. It is a conjugate acid of a malonate(1-).

Preparation

Malonic 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, malonic 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 malonic acid through these processes is extremely costly and environmentally hazardous.

Reactions

In a well - known reaction, malonic acid condenses with urea to form barbituric acid. Malonic acid is also frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum's acid. The esters of malonic acid are also used as a - CH2COOH synthon in the malonic ester synthesis.

Biological Functions

Malonic acid is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.It 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.

General Description

White crystals or crystalline powder. Sublimes in vacuum.

Air & Water Reactions

Water soluble.

Reactivity Profile

Malonic 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 Malonic 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. Malonic acid is also incompatible with bases and reducing agents.

Hazard

Strong irritant.

Fire Hazard

Flash point data for Malonic acid are not available; however, Malonic acid is probably combustible.

Flammability and Explosibility

Notclassified

Biotechnological Applications

The calcium salt of malonic acid occurs in high concentrations in beetroot. It exists in its normal state as white crystals. Malonic acid is the classic example of a competitive inhibitor: It acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.

Purification Methods

Crystallise malonic acid from *benzene/diethyl ether (1:1) containing 5% of pet ether (b 60-80o), wash with diethyl ether, then recrystallise it from H2O or acetone. Dry it under vacuum over conc H2SO4. [Beilstein 2 IV 1874.]

Malonic acidSupplier

Beijing Yangcun Chemical Co. Ltd Gold
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