Maleic acid: Difference between revisions

Latest revision as of 04:01, 13 February 2025

Maleic Acid[edit]

Maleic acid is an organic compound that is a dicarboxylic acid, with the formula C_H_O_. It is the cis-isomer of butenedioic acid, whereas the trans-isomer is known as fumaric acid. Maleic acid is a colorless or white crystalline solid that is soluble in water and is used in various industrial applications.

Structure and Properties[edit]

Maleic acid is characterized by the presence of two carboxyl groups (-COOH) attached to a carbon-carbon double bond. The cis configuration of the carboxyl groups in maleic acid leads to its distinct chemical properties compared to its trans counterpart, fumaric acid.

The molecular structure of maleic acid allows for intramolecular hydrogen bonding, which affects its solubility and melting point. Maleic acid has a melting point of approximately 135 °C and is more soluble in water than fumaric acid.

Synthesis[edit]

Maleic acid can be synthesized through the catalytic oxidation of benzene or butane. It is also produced as a byproduct in the manufacture of phthalic anhydride.

Applications[edit]

Maleic acid is used in the production of polyesters, alkyd resins, and as a precursor to maleic anhydride. It is also employed in the food industry as an acidulant and in the pharmaceutical industry for the synthesis of various compounds.

Chemical Reactions[edit]

Maleic acid readily undergoes dehydration to form maleic anhydride. It can also participate in Diels-Alder reactions due to its electron-deficient double bond, making it a useful dienophile in organic synthesis.

Health and Safety[edit]

Maleic acid is considered to be an irritant and should be handled with care. It can cause skin and eye irritation upon contact and may be harmful if ingested or inhaled.

Related Pages[edit]

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-'''Maleic acid''' is an [[organic compound]] that is a [[dicarboxylic acid]], a type of acid that contains two [[carboxyl]] groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the cis-isomer of [[butenedioic acid]], whereas [[fumaric acid]] is the trans-isomer. It is mainly used in the manufacture of [[polyester]] resins, coatings, antirust products, and agricultural products.
+{{DISPLAYTITLE:Maleic Acid}}
-== History ==
+== Maleic Acid ==
-Maleic acid was first described by [[Swedish]] chemist [[Carl Wilhelm Scheele]] in 1785. It was isolated from [[apple]] juice by [[hydrolysis]] of maleic anhydride.
+[[File:Maleinsäure.svg|thumb|right|Structural formula of maleic acid]]
-== Properties ==
+'''Maleic acid''' is an organic compound that is a dicarboxylic acid, with the formula C_H_O_. It is the cis-isomer of [[butenedioic acid]], whereas the trans-isomer is known as [[fumaric acid]]. Maleic acid is a colorless or white crystalline solid that is soluble in water and is used in various industrial applications.
-Maleic acid has a molar mass of 116.072 g/mol. It is a white crystalline compound that is soluble in water, ethanol, and acetone. Its melting point is 130-131 °C, and it decomposes before boiling. Maleic acid is a weak diprotic acid. It has a strong, unpleasant odor.
-== Production ==
+== Structure and Properties ==
-Maleic acid is produced by the oxidation of [[benzene]] or [[butane]]. The process involves the reaction of these substances with [[oxygen]] in the presence of a [[vanadium pentoxide]] catalyst.
+Maleic acid is characterized by the presence of two carboxyl groups (-COOH) attached to a carbon-carbon double bond. The cis configuration of the carboxyl groups in maleic acid leads to its distinct chemical properties compared to its trans counterpart, fumaric acid.
-== Uses ==
+The molecular structure of maleic acid allows for intramolecular hydrogen bonding, which affects its solubility and melting point. Maleic acid has a melting point of approximately 135 °C and is more soluble in water than fumaric acid.
-Maleic acid is used in the production of polyester resins and coatings. It is also used in the manufacture of antirust products and agricultural products. In addition, it is used in the synthesis of other chemicals, such as [[fumaric acid]], [[tartaric acid]], and certain [[amino acids]].
-== Health effects ==
+== Synthesis ==
-Exposure to maleic acid can cause irritation to the eyes, skin, and respiratory tract. It can also cause nausea, vomiting, and diarrhea if ingested. Long-term exposure can lead to kidney damage and respiratory problems.
+Maleic acid can be synthesized through the catalytic oxidation of [[benzene]] or [[butane]]. It is also produced as a byproduct in the manufacture of [[phthalic anhydride]].
-== See also ==
+== Applications ==
+Maleic acid is used in the production of [[polyesters]], [[alkyd resins]], and as a precursor to [[maleic anhydride]]. It is also employed in the food industry as an acidulant and in the pharmaceutical industry for the synthesis of various compounds.
+== Chemical Reactions ==
+Maleic acid readily undergoes [[dehydration]] to form maleic anhydride. It can also participate in [[Diels-Alder reactions]] due to its electron-deficient double bond, making it a useful dienophile in organic synthesis.
+== Health and Safety ==
+Maleic acid is considered to be an irritant and should be handled with care. It can cause skin and eye irritation upon contact and may be harmful if ingested or inhaled.
+== Related Pages ==
 * [[Fumaric acid]]
+* [[Butenedioic acid]]
+* [[Maleic anhydride]]
 * [[Dicarboxylic acid]]
-* [[Organic compound]]
-* [[Carboxyl]]
-[[Category:Organic compounds]]
+[[Category:Organic acids]]
 [[Category:Dicarboxylic acids]]
-[[Category:Acids]]
-{{Chem-stub}}