All Topics  
Dicarboxylic acid

 

 
   Email Print
   Bookmark   Link
 

 

Dicarboxylic acid
 
 
  Topics Dicarboxylic acid Topic Home

Dicarboxylic acids are organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s that are substituted with two carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
s. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkyl
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
, alkenyl
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
, or akynyl
Alkyne

Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
 group. Dicarboxylic acids can be used to prepare copolymers such as nylon
Nylon

Nylon is a generic designation for a family of synthetic polymers known generically as polyamides and first produced on February 28, 1935 by Wallace Carothers at DuPont....
 and polyethylene terephthalate
Polyethylene terephthalate

Polyethylene tephthalate , commonly abbreviated PET, PETE, or the obsolete PETP or PET-P), is a thermoplastic polymer resin of the polyester family and is used in synthetic fibers; beverage, food and other liquid Packaging; thermoforming applications; and engineering resins often in combination with glass fiber....
.

In general, dicarboxylic acids show the same chemical behaviour and reactivity as monocarboxylic acids. The ionization of the second carboxyl group occurs less readily than the first one.






Discussion
Ask a question about 'Dicarboxylic acid'
Start a new discussion about 'Dicarboxylic acid'
Answer questions from other users
Full Discussion Forum



Encyclopedia


Dicarboxylic acids are organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s that are substituted with two carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
s. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkyl
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
, alkenyl
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
, or akynyl
Alkyne

Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
 group. Dicarboxylic acids can be used to prepare copolymers such as nylon
Nylon

Nylon is a generic designation for a family of synthetic polymers known generically as polyamides and first produced on February 28, 1935 by Wallace Carothers at DuPont....
 and polyethylene terephthalate
Polyethylene terephthalate

Polyethylene tephthalate , commonly abbreviated PET, PETE, or the obsolete PETP or PET-P), is a thermoplastic polymer resin of the polyester family and is used in synthetic fibers; beverage, food and other liquid Packaging; thermoforming applications; and engineering resins often in combination with glass fiber....
.

In general, dicarboxylic acids show the same chemical behaviour and reactivity as monocarboxylic acids. The ionization of the second carboxyl group occurs less readily than the first one. This is because more energy is required to separate a positive hydrogen ion from the doubly charged anion than from the single charged anion.

A mnemonic
Mnemonic

A mnemonic device is a memory aid. Commonly met mnemonics are often verbal, something such as a very short poem or a special word used to help a person remember something, particularly lists, but may be visual, kinesthetic or auditory....
 to aid in remembering the order of the common nomenclature for the first six dicarboxylic acids is "Oh my, such great apple pie!" (oxalic, malonic, succinic, glutaric, adipic, pimelic). A variant for the first nine adds "Sweet as sugar!" (suberic, azelaic, sebacic) to the end of the mnemonic.

When one of the carboxy groups is replaced with an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 group, the resulting structure is called a "aldehydic acid".

Examples

Elementary dicarboxylic acids
Common name IUPAC name Chemical formula Structural formula
Oxalic acid
Oxalic acid

Oxalic acid is the chemical compound with the chemical formula H2C2O4. This dicarboxylic acid is better described with the formula HOOCCOOH....
 ethanedioic acid HOOC-COOH
Oxalic Acid
Malonic acid
Malonic acid

Malonic acid is a dicarboxylic acid with structure carbonhydrogen22. The ionised form of malonic acid, as well as its esters and salts, are known as malonates....
 propanedioic acid HOOC-(CH2)-COOH
Succinic acid
Succinic acid

Succinic acid is a dicarboxylic acid. Succinate plays a biochemical role in the citric acid cycle....
 butanedioic acid HOOC-(CH2)2-COOH
Succinic Acid
Glutaric acid
Glutaric acid

Glutaric acid is the organic compound with the chemical formula HO2C3CO2H. Although the related "linear" dicarboxylic acids adipic acid and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50%....
 pentanedioic acid HOOC-(CH2)3-COOH
Glutaric Acid
Adipic acid
Adipic acid

Adipic acid is the organic compound with the chemical formula 42. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon....
 hexanedioic acid HOOC-(CH2)4-COOH
Adipic Acid Structure
Pimelic acid
Pimelic acid

Pimelic acid is the organic compound with the chemical formula HO2C5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine....
 heptanedioic acid HOOC-(CH2)5-COOH
Pimelic Acid
Suberic acid
Suberic acid

Suberic acid, also octanedioic acid, is a dicarboxylic acid, with formula C6H122.References...
 octanedioic acid HOOC-(CH2)6-COOH
Suberic Acid
Azelaic acid
Azelaic acid

Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur , a yeast that lives on normal skin....
 nonanedioic acid HOOC-(CH2)7-COOH
Sebacic acid
Sebacic acid

Sebacic acid is a dicarboxylic acid with structure 8, and is naturally occurring.In its pure state it is a white flake or powdered crystal....
 decanedioic acid HOOC-(CH2)8-COOH
Sebacic Acid
Phthalic acid
Phthalic acid

Phthalic acid is an aromatic dicarboxylic acid, with formula C6H42. It is an isomer of isophthalic acid and terephthalic acid....
 benzene-1,2-dicarboxylic acid
o-phthalic acid		 C6H4(COOH)2
Isophthalic acid
Isophthalic acid

Isophthalic acid is an organic compound with the chemical formula C6H42. This colourless solid is an isomer of phthalic acid and terephthalic acid....
 benzene-1,3-dicarboxylic acid
m-phthalic acid		 C6H4(COOH)2
Terephthalic acid
Terephthalic acid

Terephthalic acid is the organic compound and one of three isomeric phthalic acids, all with chemical formula C6H42....
 benzene-1,4-dicarboxylic acid
p-phthalic acid		 C6H4(COOH)2


See also


Category:Dicarboxylic acids
  • Tricarboxylic acid
    Tricarboxylic acid

    A tricarboxylic acid is an organic chemistry carboxylic acid whose chemical structure contains three carboxyl group functional groups . The best-known example of a tricarboxylic acid is citric acid....