1,2,3,4-Butanetetracarboxylic acid

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1,2,3,4-Butanetetracarboxylic acid
ButanetetracarboxylicAcid.svg
Names
Other names
Butane-1,2,3,4-tetracarboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 216-938-0
PubChem CID
  • InChI=1S/C8H10O8/c9-5(10)1-3(7(13)14)4(8(15)16)2-6(11)12/h3-4H,1-2H2,(H,9,10)(H,11,12)(H,13,14)(H,15,16)
    Key: GGAUUQHSCNMCAU-UHFFFAOYSA-N
  • C(C(C(CC(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
C8H10O8
Molar mass 234.160 g·mol−1
AppearanceWhite solid
Melting point 236 °C (457 °F; 509 K)
246 ºC for meso
227-230 ºC for (R,R)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,2,3,4-Butanetetracarboxylic acid is an organic compound with the formula HO2CCH2CH(CO2H)CH(CO2H)CH2CO2H. It is one of the simplest stable tetracarboxylic acids. The compound exists as two diastereomers, meso and the (R,R)/(S,S) pair. All are white solids. The compound is produced by oxidation of tetrahydrophthalic anhydride. [1]

Uses and reactions

Among the several possible uses, it has been repeatedly investigated in the textile industry, [2] e.g., for permanent press clothing. [3] As expected for a polycarboxylate, it binds zinc to afford coordination polymers. [4]

It forms a dianhydride (RN 4534-73-0), which consists of two succinic anhydride-like rings. [1]

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

<span class="mw-page-title-main">Copper(II) nitrate</span> Chemical compound

Copper(II) nitrate describes any member of the family of inorganic compounds with the formula Cu(NO3)2(H2O)x. The hydrates are hygroscopic blue solids. Anhydrous copper nitrate forms blue-green crystals and sublimes in a vacuum at 150-200 °C. Common hydrates are the hemipentahydrate and trihydrate.

<span class="mw-page-title-main">Malonic acid</span> Carboxylic acid with chemical formula CH2(COOH)2

Malonic 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'.

<span class="mw-page-title-main">Zinc chloride</span> Chemical compound

Zinc chloride is an inorganic chemical compound with the formula ZnCl2·nH2O, with n ranging from 0 to 4.5, forming hydrates. Zinc chloride, anhydrous and its hydrates, are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride.

<span class="mw-page-title-main">Polyimide</span> Class of polymers

Polyimide is a polymer containing imide groups belonging to the class of high-performance plastics. With their high heat-resistance, polyimides enjoy diverse applications in roles demanding rugged organic materials, such as high temperature fuel cells, displays, and various military roles. A classic polyimide is Kapton, which is produced by condensation of pyromellitic dianhydride and 4,4'-oxydianiline.

<span class="mw-page-title-main">Organic acid anhydride</span> Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride.Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

<span class="mw-page-title-main">Zinc acetate</span> Chemical compound

Zinc acetate is a salt with the formula Zn(CH3CO2)2, which commonly occurs as the dihydrate Zn(CH3CO2)2·2H2O. Both the hydrate and the anhydrous forms are colorless solids that are used as dietary supplements. When used as a food additive, it has the E number E650.

<span class="mw-page-title-main">Maleic anhydride</span> Chemical compound

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<span class="mw-page-title-main">Vanadium compounds</span>

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<span class="mw-page-title-main">Aconitic acid</span> Chemical compound

Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase.

<span class="mw-page-title-main">Oxocarbon</span> Chemical compounds made of only carbon and oxygen

In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide. Many other stable or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide and mellitic anhydride.

Zinc compounds are chemical compounds containing the element zinc which is a member of the group 12 of the periodic table. The oxidation state of zinc in most compounds is the group oxidation state of +2. Zinc may be classified as a post-transition main group element with zinc(II). Zinc compounds are noteworthy for their nondescript appearance and behavior: they are generally colorless, do not readily engage in redox reactions, and generally adopt symmetrical structures.

<span class="mw-page-title-main">Cadmium acetate</span> Chemical compound

Cadmium acetate is the chemical compound with the formula Cd(O2CCH3)2(H2O)2. The compound is marketed both as the anhydrous form and as a dihydrate, both of which are white or colorless. Only the dihydrate has been verified by X-ray crystallography.

Naphthalenetetracarboxylic dianhydride (NTDA) is an organic compound related to naphthalene. The compound is a beige solid. NTDA is most commonly used as a precursor to naphthalenediimides (NDIs), a family of compounds with many uses.

<span class="mw-page-title-main">Pyromellitic dianhydride</span> Chemical compound

Pyromellitic dianhydride (PMDA) is an organic compound with the formula C6H2(C2O3)2. It is the double carboxylic acid anhydride that is used in the preparation of polyimide polymers such as Kapton. It is a white, hygroscopic solid. It forms a hydrate.

<span class="mw-page-title-main">Perylenetetracarboxylic dianhydride</span> Chemical compound

Perylenetetracarboxylic dianhydride (PTCDA) is an organic dye molecule and an organic semiconductor. It is used as a precursor to a class of molecules known as Rylene dyes, which are useful as pigments and dyes. It is a dark red solid with low solubility in aromatic solvents. The compound has attracted much interest as an organic semiconductor.

Tetrahydrophthalic anhydride is an organic compound with the formula C6H8C2O3. The compound exists as two isomers, this article being focused on the more common cis isomer. It is a white solid that is soluble in organic solvents.

<span class="mw-page-title-main">Transition metal carboxylate complex</span> Class of chemical compounds

Transition metal carboxylate complexes are coordination complexes with carboxylate (RCO2) ligands. Reflecting the diversity of carboxylic acids, the inventory of metal carboxylates is large. Many are useful commercially, and many have attracted intense scholarly scrutiny. Carboxylates exhibit a variety of coordination modes, most common are κ1- (O-monodentate), κ2 (O,O-bidentate), and bridging.

Sulfidogermanates or thiogermanates are chemical compounds containing anions with sulfur atoms bound to germanium. They are in the class of chalcogenidotetrelates. Related compounds include thiosilicates, thiostannates, selenidogermanates, telluridogermanates and selenidostannates.

References

  1. 1 2 Nagao, R.; Marumo, F.; Saito, Y.; Asahara, T. (1971). "The Crystal Structure of Butane-1,2,3,4-tetracarboxylic Dianhydride". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 27 (3): 569–572. Bibcode:1971AcCrB..27..569N. doi:10.1107/s0567740871002577.
  2. Eltahlawy, K.; Elbendary, M.; Elhendawy, A.; Hudson, S. (2005). "The Antimicrobial Activity of Cotton Fabrics Treated with Different Crosslinking Agents and Chitosan". Carbohydrate Polymers. 60 (4): 421–430. doi:10.1016/j.carbpol.2005.02.019.
  3. Welch, Clark M. (1988). "Tetracarboxylic Acids as Formaldehyde-Free Durable Press Finishing Agents". Textile Research Journal. 58 (8): 480–486. doi:10.1177/004051758805800809.
  4. Wei, Guo-Hua; Yang, Jin; Ma, Jian-Fang; Liu, Ying-Ying; Li, Shun-Li; Zhang, Lai-Ping (2008). "Syntheses, Structures and Luminescent Properties of Zinc(II) and Cadmium(II) Coordination Complexes Based on New Bis(imidazolyl)ether and Different Carboxylate Ligands". Dalton Transactions (23): 3080–3092. doi:10.1039/b716657e. PMID   18521450.