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Not to be confused with malic acid or maleic acid.
Malonic acid
Skeletal formula of malonic acid
Ball-and-stick model of the malonic acid molecule
Names
IUPAC name
propanedioic acid
Other names
methanedicarboxylic acid
Identifiers
141-82-2 YesY
ChEBI CHEBI:30794 YesY
ChEMBL ChEMBL7942 YesY
ChemSpider 844 YesY
DrugBank DB02175 YesY
Jmol-3D images Image
Image
PubChem 867
Properties
C3H4O4
Molar mass 104.06 g·mol−1
Density 1.619 g/cm3
Melting point 135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
Boiling point decomposes
Miscible
Acidity (pKa) pKa1 = 2.83[1]
pKa2 = 5.69[1]
Related compounds
Other anions
malonate
acetic acid
oxalic acid
propionic acid
tartronic acid
acrylic acid
butyric acid
succinic acid
fumaric acid
Related compounds
propanone
propionaldehyde
propanedial
dimethyl malonate
Hazards
Safety data sheet External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
Infobox references

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 μᾶλον (malon) meaning 'apple'.

Biochemistry[edit]

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[2] (complex II) in the respiratory electron transport chain.

Preparation[edit]

A classical preparation of malonic acid starts from chloroacetic acid:[3]

Preparation of malonic acid from chloroacetic acid.

Sodium carbonate generates the sodium salt, which is then reacted with sodium cyanide to provide the cyano acetic acid salt via a nucleophilic substitution. The nitrile group can be hydrolyzed with sodium hydroxide to sodium malonate, and acidification affords malonic acid.

Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes (1800-1885) via the oxidation of malic acid.[4]

More recently, malonic acid has been produced through fermentation of glucose from renewable feedstock and purification of raw bio-based malonic acid. This higher yielding route could offer environmental benefits via elimination of cyanide and chloroacetic acid use in addition to carbon sequestration.[5]

Organic reactions[edit]

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.

Additionally, the coenzyme A derivative of malonate, malonyl-CoA, is an important precursor in fatty acid biosynthesis along with acetyl CoA. Malonyl CoA is formed from acetyl CoA by the action of acetyl-CoA carboxylase, and the malonate is transferred to an acyl carrier protein to be added to a fatty acid chain.

Malonic acid is also known to be a competitive inhibitor of succinic dehydrogenase, the enzyme responsible for the dehydrogenation of succinate within Krebs cycle.

Applications[edit]

Malonic acid is a precursor to specialty polyesters. It can be converted into 1,3 propanediol for use in polyesters and polymers and a projected market size of $621.2 million by 2021. It 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 malonic 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. [6] 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. [7]

It 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. Global production of malonic acid and its malonate ester derivatives is estimated at 16,000 to 20,000 metric tons per year. Potential growth of these markets could result from advances in industrial biotechnology that seeks to displace petroleum-based chemicals in industrial applications. Malonic acid was listed as one of the top 30 chemicals to be produced from biomass by the US Department of Energy.[8] 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.

Malonic acid is used as a building block chemical to produce numerous valuable compounds.[9]

Most recently, malonic acid has been used to produce an enhanced starch-based resin, which is environmentally-benign, uses water-based processing without toxic catalysts.[10]

Eastman Kodak company and others use malonic acid and derivatives as a surgical adhesive.[11]

References[edit]

  1. ^ a b pKa Data Compiled by R. Williams (pdf; 77 kB)
  2. ^ Pardee, Arthur B.; Potter, Van R. (26 October 1948). "Malonate Inhibition of Oxidations in the Krebs Tricarboxylic Acid Cycle" (PDF). Journal of Biological Chemistry (178): 241–250. Retrieved 5 June 2015. 
  3. ^ Nathan Weiner. "Malonic acid". Org. Synth. ; Coll. Vol. 2, p. 376 
  4. ^ See:
  5. ^ See:
    • Recombinant host cells for the production of malonate. PCT/US2013/029441 2012.
  6. ^ Fäcke, T., Subramanian R., Dvorchak, M., Feng, S. Diethylmalonate Blocked Isocyanates As Crosslinkers For Low Temperature Cure Powder Coatings. 2004 International Waterborne, High-Solids, and Powder Coatings Symposium.
  7. ^ James, S. Global Automotive Coatings Market. 2015 Grand View Research Market Report
  8. ^ Werpy, T., Petersen, G. Top Value Added Chemicals from Biomass. 2004 US Department of Energy.
  9. ^ Hildbrand, S.; Pollak, P. Malonic Acid & Derivatives. March 15, 2001. Ullmann's Encyclopedia of Industrial Chemistry
  10. ^ Netravali, A., Dastidar, T. Crosslinked native and waxy starch resin compositions and processes for their manufacture. 2013 US. Appl No. 14/418,940.
  11. ^ Hawkins, G., Fassett, D. Surgical Adhesive Compositions. 1971 US Patent No. 3,591,676.

External links[edit]


Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Malonic_acid — Please support Wikipedia.
This page uses Creative Commons Licensed content from Wikipedia. A portion of the proceeds from advertising on Digplanet goes to supporting Wikipedia.
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Malonic Ester Synthesis

This video describes the malonic ester synthesis. This is a companion video to the acetoacetic ester synthesis video. Please watch the acetoacetic ester ...

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The decarboxylation (loss of carbon dioxide) of malonic acid and a beta-keto acid More free lessons at: http://www.khanacademy.org/video?v=8G0RkfeKfBg.

Malonic Ester Synthesis

Describes the use in organic synthesis and reaction mechanism of the malonic ester synthesis to make carboxylic acids.

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3D model of Malonic acid.

Enols & Enolates: Acetoacetic and Malonic Ester Synthesis

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34 news items

Biomass Magazine

Biomass Magazine
Tue, 10 Mar 2015 15:52:30 -0700

Lygos Inc., an industrial biotechnology company, recently announced that it has successfully achieved pilot-scale production of malonic acid from sugar. Malonic acid is a high-value specialty chemical useful for production of a variety of ...
 
Mondaq News Alerts (registration)
Fri, 21 Aug 2015 03:41:15 -0700

There was also a striking contrast between the specificity of pemetrexed disodium and the general terms used in the claim for the methyl malonic acid lowering agent and folic acid compounds, which had been referred to as any 'pharmaceutical derivative ...

Chemicals Technology

Chemicals Technology
Thu, 05 Mar 2015 04:00:00 -0800

Lygos has completed the pilot-scale production of malonic acid using renewable resources at Lawrence Berkeley National Laboratory's advanced bio-fuels process demonstration unit (ABPDU). The new manufacturing technology is said to replace the ...
 
Biobased Digest
Sun, 08 Mar 2015 22:14:52 -0700

In California, Lygos has successfully achieved pilot scale production of malonic acid from sugar. A versatile compound, malonic acid was identified by the U.S. Department of Energy as one of the “Top 30 Value Added Chemicals” to be produced from ...
 
Pollution Online (press release)
Sun, 08 Mar 2015 22:37:30 -0700

Lygos, Inc. (http://www.lygos.com) announced today that it has successfully achieved pilot scale production of malonic acid from sugar. Lygos' novel manufacturing technology decreases CO2 emissions, eliminates toxic inputs and could replace the ...
 
Business Wire (press release)
Tue, 26 Aug 2014 09:07:30 -0700

Global Market Report of Malonic acid (CAS 141-82-2) aims at providing comprehensive data on Malonic acid globally and regionally (Europe, Asia, North America, Latin America etc.). It captures Malonic acid market trends, pays close attention to Malonic ...
 
Biomass Magazine
Tue, 28 Oct 2014 16:03:45 -0700

Biomass Magazine reported in 2012 that the company could not disclose specifically which molecules they were targeting, but now the company is speaking publically about their first product, malonic acid. “That grant is really focused on how you get ...

Biobased Digest

Biobased Digest
Tue, 23 Jun 2015 19:37:30 -0700

But that technology has pathways to a collection of target molecules, which include acrylonitrile, as well as butanol, BDO, 3-HP, acetyl-CoA, malonyl-CoA, malonate semialdehyde, 3-HP, acrylic acid, PDO, malonic acid, ethyl 3-HP, propiolactone ...
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