Mellitic acid
Encyclopedia
Mellitic acid, also called graphitic acid or benzenehexacarboxylic acid, is an acid
first discovered in 1799 by M. H. Klaproth
in the mineral
mellite
(honeystone), which is the aluminium
salt
of the acid.
with ammonium carbonate
, boiling off the excess of the ammonium
salt and adding ammonia
to the solution. The precipitated alumina is filtered off, the filtrate evaporated and the ammonium salt of the acid purified by recrystallization
. The ammonium salt is then converted into the lead
salt by precipitation with lead acetate
and the lead salt decomposed by hydrogen sulfide
. The acid may also be prepared by the oxidation of pure carbon
, or of hexamethyl benzene
, in the cold, by alkaline potassium permanganate
, or by hot concentrated nitric acid
.
and alcohol
. It is a very stable compound, chlorine
, concentrated nitric acid
and hydriodic acid having no action upon it. It is decomposed, on dry distillation, into carbon dioxide
and pyromellitic acid, C10H6O8; when distilled with lime
it gives carbon dioxide and benzene
. Long digestion of the acid with excess of phosphorus pentachloride results in the formation of the acid chloride, which crystallizes in needles, melting at 190 °C. By heating the ammonium salt of the acid to 150–160 °C so long as ammonia is evolved, a mixture of paramide (mellimide), C6(CONHCO)3, and ammonium euchroate is obtained. The mixture may be separated by dissolving out the ammonium euchroate with water. Paramide is a white amorphous powder, insoluble in water and alcohol.
The high stability of mellitic acid salts and that they are the endproduct of the oxidation of polycyclic aromatic hydrocarbon
s, which are present in the solar system, made them a possible organic substance in Martian
soil.
Mellitates (and salts of other benzene polycarboxylic acids) of iron
and cobalt
have interesting magnetic properties.
Acid
An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...
first discovered in 1799 by M. H. Klaproth
Martin Heinrich Klaproth
Martin Heinrich Klaproth was a German chemist.Klaproth was born in Wernigerode. During a large portion of his life he followed the profession of an apothecary...
in the mineral
Mineral
A mineral is a naturally occurring solid chemical substance formed through biogeochemical processes, having characteristic chemical composition, highly ordered atomic structure, and specific physical properties. By comparison, a rock is an aggregate of minerals and/or mineraloids and does not...
mellite
Mellite
Mellite, also called honeystone, is an unusual mineral being also an organic chemical. Chemically identified as an aluminium salt of mellitic acid; that is, aluminium benzene hexacarboxylate hydrate, with the chemical formula Al2C66·16H2O....
(honeystone), which is the aluminium
Aluminium
Aluminium or aluminum is a silvery white member of the boron group of chemical elements. It has the symbol Al, and its atomic number is 13. It is not soluble in water under normal circumstances....
salt
Salt
In chemistry, salts are ionic compounds that result from the neutralization reaction of an acid and a base. They are composed of cations and anions so that the product is electrically neutral...
of the acid.
Preparation
Mellitic acid may be prepared by warming melliteMellite
Mellite, also called honeystone, is an unusual mineral being also an organic chemical. Chemically identified as an aluminium salt of mellitic acid; that is, aluminium benzene hexacarboxylate hydrate, with the chemical formula Al2C66·16H2O....
with ammonium carbonate
Ammonium carbonate
Ammonium carbonate is a commercial salt with the chemical formula 2CO3. It is used when crushed as a smelling salt. It can be crushed when needed in order to revive someone who has fainted...
, boiling off the excess of the ammonium
Ammonium
The ammonium cation is a positively charged polyatomic cation with the chemical formula NH. It is formed by the protonation of ammonia...
salt and adding ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
to the solution. The precipitated alumina is filtered off, the filtrate evaporated and the ammonium salt of the acid purified by recrystallization
Recrystallization (chemistry)
-Chemistry:In chemistry, recrystallization is a procedure for purifying compounds. The most typical situation is that a desired "compound A" is contaminated by a small amount of "impurity B". There are various methods of purification that may be attempted , which includes recrystallization...
. The ammonium salt is then converted into the lead
Lead
Lead is a main-group element in the carbon group with the symbol Pb and atomic number 82. Lead is a soft, malleable poor metal. It is also counted as one of the heavy metals. Metallic lead has a bluish-white color after being freshly cut, but it soon tarnishes to a dull grayish color when exposed...
salt by precipitation with lead acetate
Lead acetate
Lead acetate can refer to:* Lead acetate , Pb4* Lead acetate , Pb2...
and the lead salt decomposed by hydrogen sulfide
Hydrogen sulfide
Hydrogen sulfide is the chemical compound with the formula . It is a colorless, very poisonous, flammable gas with the characteristic foul odor of expired eggs perceptible at concentrations as low as 0.00047 parts per million...
. The acid may also be prepared by the oxidation of pure carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
, or of hexamethyl benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
, in the cold, by alkaline potassium permanganate
Potassium permanganate
Potassium permanganate is an inorganic chemical compound with the formula KMnO4. It is a salt consisting of K+ and MnO4− ions. Formerly known as permanganate of potash or Condy's crystals, it is a strong oxidizing agent. It dissolves in water to give intensely purple solutions, the...
, or by hot concentrated nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
.
Reactions
It crystallizes in fine silky needles and is soluble in waterWater
Water is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...
and alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
. It is a very stable compound, chlorine
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...
, concentrated nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
and hydriodic acid having no action upon it. It is decomposed, on dry distillation, into carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...
and pyromellitic acid, C10H6O8; when distilled with lime
Lime (mineral)
Lime is a general term for calcium-containing inorganic materials, in which carbonates, oxides and hydroxides predominate. Strictly speaking, lime is calcium oxide or calcium hydroxide. It is also the name for a single mineral of the CaO composition, occurring very rarely...
it gives carbon dioxide and benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
. Long digestion of the acid with excess of phosphorus pentachloride results in the formation of the acid chloride, which crystallizes in needles, melting at 190 °C. By heating the ammonium salt of the acid to 150–160 °C so long as ammonia is evolved, a mixture of paramide (mellimide), C6(CONHCO)3, and ammonium euchroate is obtained. The mixture may be separated by dissolving out the ammonium euchroate with water. Paramide is a white amorphous powder, insoluble in water and alcohol.
The high stability of mellitic acid salts and that they are the endproduct of the oxidation of polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbons , also known as poly-aromatic hydrocarbons or polynuclear aromatic hydrocarbons, are potent atmospheric pollutants that consist of fused aromatic rings and do not contain heteroatoms or carry substituents. Naphthalene is the simplest example of a PAH...
s, which are present in the solar system, made them a possible organic substance in Martian
Mars
Mars is the fourth planet from the Sun in the Solar System. The planet is named after the Roman god of war, Mars. It is often described as the "Red Planet", as the iron oxide prevalent on its surface gives it a reddish appearance...
soil.
Mellitates (and salts of other benzene polycarboxylic acids) of iron
Iron
Iron is a chemical element with the symbol Fe and atomic number 26. It is a metal in the first transition series. It is the most common element forming the planet Earth as a whole, forming much of Earth's outer and inner core. It is the fourth most common element in the Earth's crust...
and cobalt
Cobalt
Cobalt is a chemical element with symbol Co and atomic number 27. It is found naturally only in chemically combined form. The free element, produced by reductive smelting, is a hard, lustrous, silver-gray metal....
have interesting magnetic properties.