Aluminium triacetate, formally named aluminium acetate,
is a
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with composition . Under
standard conditions
Standard temperature and pressure (STP) are standard sets of conditions for experimental measurements to be established to allow comparisons to be made between different sets of data. The most used standards are those of the International Union ...
it appears as a white,
water
Water (chemical formula ) is an Inorganic compound, inorganic, transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living ...
-soluble solid
that decomposes on heating at around 200 °C.
The triacetate
hydrolyses
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysis ...
to a mixture of basic hydroxide /
acetate salts
In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...
,
and multiple species co-exist in
chemical equilibrium
In a chemical reaction, chemical equilibrium is the state in which both the Reagent, reactants and Product (chemistry), products are present in concentrations which have no further tendency to change with time, so that there is no observable chan ...
, particularly in aqueous solutions of the acetate ion; the name aluminium acetate is commonly used for this mixed system.
It has therapeutic applications for its anti-itching,
astringent
An astringent (sometimes called adstringent) is a chemical that shrinks or constricts body tissues. The word derives from the Latin ''adstringere'', which means "to bind fast". Calamine lotion, witch hazel, and yerba mansa, a Californian pla ...
, and
antiseptic
An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...
properties,
and, as an
over-the-counter preparation like
Burow's solution
Burow's solution is an aqueous solution of aluminium triacetate. It is available in the U.S. as an over-the-counter drug for topical administration, with brand names including Domeboro (Moberg Pharma), Domeboro Otic (ear drops), Star-Otic, and Bor ...
,
it is used to treat
ear infections
Otitis is a general term for inflammation or infection, inner ear infection, middle ear infection of the ear, in both humans and other animals. When infection is present, it may be viral or bacterial. When inflammation is present due to fluid bui ...
.
Burow's solution preparations have been diluted and modified with
amino acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha a ...
s to make them more
palatable Palatability (or palatableness) is the hedonic reward (i.e., pleasure) provided by foods or fluids that are agreeable to the "palate", which often varies relative to the homeostatic satisfaction of nutritional, water, or energy needs. The palatabi ...
for use as
gargle
Gargling is the act of bubbling liquid in the mouth. It is also the washing of one's mouth and throat with a liquid, such as mouthwash, that is kept in motion by breathing through it with a gurgling sound.
A traditional home remedy of gargling ...
s for conditions like
aphthous ulcer
Aphthous stomatitis, or recurrent aphthous stomatitis (RAS), is a common condition characterized by the repeated formation of benign and non-contagious mouth ulcers (aphthae) in otherwise healthy individuals. The informal term ''canker sore'' i ...
s of the mouth.
In
veterinary medicine
Veterinary medicine is the branch of medicine that deals with the prevention, management, diagnosis, and treatment of disease, disorder, and injury in animals. Along with this, it deals with animal rearing, husbandry, breeding, research on nutri ...
, aluminium triacetate's astringency property is used for treating
Mortellaro disease
Digital dermatitis is a disease that causes lameness in cattle. It was first discovered in Italy in 1974 by Cheli and Mortellaro. This disease is caused by a mixture of different bacteria. Anaerobic bacteria, including spirochetes of the genus ...
in hoofed animals such as cattle.
Aluminium triacetate is used as a
mordant
A mordant or dye fixative is a substance used to set (i.e. bind) dyes on fabrics by forming a coordination complex with the dye, which then attaches to the fabric (or tissue). It may be used for dyeing fabrics or for intensifying stains in ...
agent with dyes like
alizarin
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Historic ...
,
both alone and in combination. Together with
aluminium diacetate
Aluminium diacetate, also known as basic aluminium acetate, is a white powder with the chemical formula C4H7AlO5. It is one of a number of aluminium acetates and can be prepared in a reaction of sodium aluminate (NaAlO2) with acetic acid.
Medici ...
or with
aluminium sulfacetate
Aluminium sulfacetate is a mixture of aluminium salts dissolved in water with formula .
Uses
It is an evenly balanced mixture of aluminium sulfate and aluminium acetate. It can be used as a mordant, which is a substance used to set dyes on fabri ...
it is used with
cotton
Cotton is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure cellulose, and can contain minor pe ...
, other
cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell w ...
fibres,
and
silk
Silk is a natural protein fiber, some forms of which can be woven into textiles. The protein fiber of silk is composed mainly of fibroin and is produced by certain insect larvae to form cocoons. The best-known silk is obtained from the ...
.
It has also been combined with
ferrous acetate
Iron(II) acetate is a coordination complex with formula Fe(O2CCH3)2. It is a white solid, although impure samples can be slightly colored. A light green tetrahydrate is also known, which is highly soluble in water.
Preparation and structure
Ir ...
to produce different colours.
Nomenclature
According to the
formal rules for naming inorganic compounds, the name for is aluminium acetate,
though more formal names like aluminium(III) acetate and aluminium ethanoate are acceptable.
The use of the "tri" multiplying prefix in the name aluminium triacetate, while not technically required, is regularly used to avoid potential confusion with related compounds with
hydroxo ligands. Basic
aluminium diacetate
Aluminium diacetate, also known as basic aluminium acetate, is a white powder with the chemical formula C4H7AlO5. It is one of a number of aluminium acetates and can be prepared in a reaction of sodium aluminate (NaAlO2) with acetic acid.
Medici ...
, formally hydroxyaluminium diacetate (
CAS RN
A CAS Registry Number (also referred to as CAS RN or informally CAS Number) is a unique identifier, unique identification number assigned by the Chemical Abstracts Service (CAS), US to every chemical substance described in the open scientific li ...
142-03-0),
has composition with one hydroxo ligand in place of an acetate ligand, and dibasic
aluminium monoacetate
Aluminium monoacetate, also known as dibasic aluminium acetate, and formally named dihydroxy aluminium acetate, is a salt of aluminium with acetic acid. It has the formula Al(OH)2(CH3COO), with aluminium in an oxidation state of +3, and appears ...
, formally dihydroxyaluminium acetate (CAS RN 7360-44-3), has composition with only one acetate ligand. These three compounds are distinct in the solid phase but are usually treated as a group and described collectively as aluminium acetate in solution, due to the triacetate
hydrolyzing
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysis ...
to a mixture which includes the other two forms.
The abbreviation as AlAc, along with variants like and , are sometimes used in the discipline of
geochemistry
Geochemistry is the science that uses the tools and principles of chemistry to explain the mechanisms behind major geological systems such as the Earth's crust and its oceans. The realm of geochemistry extends beyond the Earth, encompassing the ...
, though these are inconsistent with standard practice in mainstream
chemistry.
Structure
The formula indicates the presence of aluminium metal centres in the +3
oxidation state
In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to different atoms were fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. C ...
and
acetate groups in a ratio of 1:3. Images used to represent this substance, such as those shown at left, represent two highly oversimplified approximations of the solid-state structure: the first is as a purely
ionic salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...
with a single aluminium(III)
cation (Al
3+) surrounded by and associated
electrostatically
Electrostatics is a branch of physics that studies electric charges at rest (static electricity).
Since classical times, it has been known that some materials, such as amber, attract lightweight particles after rubbing. The Greek word for amber ...
with three acetate anions (), but this should not be taken to convey information about the
crystal structure
In crystallography, crystal structure is a description of the ordered arrangement of atoms, ions or molecules in a crystalline material. Ordered structures occur from the intrinsic nature of the constituent particles to form symmetric patterns ...
. For example, sodium chloride (NaCl) has a cation-to-anion
stoichiometry of 1:1, but it has a
cubic structure
In crystallography, the cubic (or isometric) crystal system is a crystal system where the unit cell is in the shape of a cube. This is one of the most common and simplest shapes found in crystals and minerals.
There are three main varieties of ...
with each ion surrounded
octahedrally by six ions of the opposite charge.
The other image is a
molecular form with the three acetate groups
covalently bonded
A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...
to the metal centre in a
trigonal planar geometry and
intermolecular interactions
An intermolecular force (IMF) (or secondary force) is the force that mediates interaction between molecules, including the electromagnetic forces of attraction
or repulsion which act between atoms and other types of neighbouring particles, e.g. a ...
holding the molecules together with each other in the crystal structure. It is highly likely that the solid state structure is more complicated and includes both covalent and ionic characteristics and it is possible that multiple aluminium centres and / or
bridging acetate groups might be present – both of these have been reported in aluminium acetate
solution
Solution may refer to:
* Solution (chemistry), a mixture where one substance is dissolved in another
* Solution (equation), in mathematics
** Numerical solution, in numerical analysis, approximate solutions within specified error bounds
* Soluti ...
and
aluminium chloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contam ...
is known to exist as a
dimer
Dimer may refer to:
* Dimer (chemistry), a chemical structure formed from two similar sub-units
** Protein dimer, a protein quaternary structure
** d-dimer
* Dimer model, an item in statistical mechanics, based on ''domino tiling''
* Julius Dimer ...
.
NMR
Nuclear magnetic resonance (NMR) is a physical phenomenon in which nuclei in a strong constant magnetic field are perturbed by a weak oscillating magnetic field (in the near field) and respond by producing an electromagnetic signal with ...
investigations of the aqueous aluminium(III) / acetate system show the presence of aluminium as a hexaaqua
complex
Complex commonly refers to:
* Complexity, the behaviour of a system whose components interact in multiple ways so possible interactions are difficult to describe
** Complex system, a system composed of many components which may interact with each ...
, , as well as mononuclear species with different substitutions. In addition, the investigations demonstrate that a significant solution-phase species is an
tridecamer, a
moiety
Moiety may refer to:
Chemistry
* Moiety (chemistry), a part or functional group of a molecule
** Moiety conservation, conservation of a subgroup in a chemical species
Anthropology
* Moiety (kinship), either of two groups into which a society is ...
reported in conflicting mechanisms of hydrolysis and
polymerisation
In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many for ...
aluminium solutions. Other trivalent metal cations are known to form polynuclear species:
iron(III) acetate
Ferric acetate is the acetate salt of the coordination complex e3O(OAc)6(H2O)3 (OAc− is CH3CO2−). Commonly the salt is known as "basic iron acetate". The formation of the red-brown complex was once used as a test for ferric ions.
Struct ...
, for example, forms a trinuclear structure with a triply-bridged oxo centre
with the cation The compound
chromium acetate hydroxide
Chromium acetate hydroxide is the coordination complex with the formula r2(OH)3(OAc)3sub>4. A dark violet solid, it crystallizes as the triacontatetrahydrate (34 molecules of water of crystallization). It is water soluble.
Structure
The complex ...
, Cr
3(OH)
2(OAc)
7, has also been described as isostructural.
Analogous
Analogy (from Greek ''analogia'', "proportion", from ''ana-'' "upon, according to" lso "against", "anew"+ ''logos'' "ratio" lso "word, speech, reckoning" is a cognitive process of transferring information or meaning from a particular subject ...
ruthenium(III), vanadium(III), rhodium(III), and iridium(III) compounds with trinuclear structures are known.
Copper(II) acetate
Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu(OAc)2 where AcO− is acetate (). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is availab ...
and
chromium(II) acetate
Chromium(II) acetate hydrate, also known as chromous acetate, is the coordination compound with the formula Cr2(CH3CO2)4(H2O)2. This formula is commonly abbreviated Cr2(OAc)4(H2O)2. This red-coloured compound features a quadruple bond. The prepara ...
both have dinuclear dihydrate structures, M
2(OAc)
4(H
2O)
2,
as does
rhodium(II) acetate
Rhodium(II) acetate is the coordination compound with the formula Rh2(AcO)4, where AcO− is the acetate ion (). This dark green powder is slightly soluble in polar solvents, including water. It is used as a catalyst for cyclopropanation of a ...
;
each shows significant metal-metal bonding interactions.
Chemistry
Preparation
According to the ''CRC Handbook of Inorganic Compounds,'' aluminium triacetate is a white, water-soluble solid and is usually prepared from
aluminium chloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contam ...
or directly from
aluminium
Aluminium (aluminum in American and Canadian English) is a chemical element with the symbol Al and atomic number 13. Aluminium has a density lower than those of other common metals, at approximately one third that of steel. I ...
by heating in an
acetic acid solution with
acetic anhydride.
:3 + → + 3 HCl
:6 + 2 Al → 2 + 3
Theoretically all of the aluminium / acetate / hydroxide
salts
In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...
can be prepared from
aluminium hydroxide
Aluminium hydroxide, Al(OH)3, is found in nature as the mineral gibbsite (also known as hydrargillite) and its three much rarer polymorphs: bayerite, doyleite, and nordstrandite. Aluminium hydroxide is amphoteric, i.e., it has both basic an ...
or
sodium aluminate
Sodium aluminate is an inorganic chemical that is used as an effective source of aluminium hydroxide for many industrial and technical applications. Pure sodium aluminate (anhydrous) is a white crystalline solid having a formula variously given as ...
and acetic acid, but formation of the triacetate only occurs in the absence of water.
In solutions, the diacetate is the major product formed, and is also produced when aluminium chloride is treated with a
sodium acetate
Sodium acetate, CH3COONa, also abbreviated Na O Ac, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.
Applications
Biotechnological
Sodium acetate is used as the carbon source for culturing bacteria ...
solution in basic conditions.
The equations for these processes are:
:2 + → + 2 NaOH
:2 + + NaOH → + 3 NaCl
:2 + + 2 → + 3 NaOH
An improved process using a combination of
aluminium chloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contam ...
and sodium aluminate with sodium acetate prepared ''
in situ
''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premises", or "in place" to describe where an event takes place and is used in ...
'' has been
patent
A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an enabling disclosure of the invention."A ...
ed:
:29 + 10 NaOH + 84 + 13 → 42 + 39 NaCl + 26
The
mordant
A mordant or dye fixative is a substance used to set (i.e. bind) dyes on fabrics by forming a coordination complex with the dye, which then attaches to the fabric (or tissue). It may be used for dyeing fabrics or for intensifying stains in ...
s aluminium triacetate and
aluminium sulfacetate
Aluminium sulfacetate is a mixture of aluminium salts dissolved in water with formula .
Uses
It is an evenly balanced mixture of aluminium sulfate and aluminium acetate. It can be used as a mordant, which is a substance used to set dyes on fabri ...
can be prepared from
aluminium sulfate, the product formed being determined by the amount of
lead(II) acetate
Lead(II) acetate (Pb(CH3COO)2), also known as lead acetate, lead diacetate, plumbous acetate, sugar of lead, lead sugar, salt of Saturn, or Goulard's powder, is a white crystalline chemical compound with a slightly sweet taste. Like many other l ...
used:
: + 3 → 2 + 3
: + 2 → + 2
Decomposition
On heating, aluminium triacetate decomposes above 200 °C in a process similar to that of
aluminium formate
Aluminium formate is the aluminium salt (chemistry), salt of formic acid, with the chemical formula Al(HCOO)3. It can be produced via the reaction of aluminium soaps and formic acid. Reaction between formic acid and aluminium hydroxide yields Al(H ...
.
The process begins with loss of acetic anhydride () between 120 and 140 °C
to form the a mixture of the basic oxide acetates such as and ,
which are ultimately transformed to (
alumina), first as an
amorphous anhydrous solid and then through other solid
phases (γ-, δ-, and θ-
crystal forms) to ultimately become
polymorphic α-:
:2 → + → + 3
:2 → + 2 +
Hydrolysis
Aluminium triacetate hydrolyses to produce both the mono- and di-basic hydroxide acetates in solution or by
hygroscopy
Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption or adsorption from the surrounding environment, which is usually at normal or room temperature. If water molecules become suspended among the substance' ...
:
: + → +
: + 2 → + 2
Uses
According to the
National Cancer Institute
The National Cancer Institute (NCI) coordinates the United States National Cancer Program and is part of the National Institutes of Health (NIH), which is one of eleven agencies that are part of the U.S. Department of Health and Human Services. ...
, the aluminium acetates are used
topically
A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes ...
in humans as
antiseptic agent
An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living biological tissue, tissue/skin to reduce the possibility of infection ...
s, which also cause
body tissues to shrink.
Its astringency property is also used for treating
Mortellaro disease
Digital dermatitis is a disease that causes lameness in cattle. It was first discovered in Italy in 1974 by Cheli and Mortellaro. This disease is caused by a mixture of different bacteria. Anaerobic bacteria, including spirochetes of the genus ...
in hoofed animals such as cattle.
Aluminium acetate promotes healing of
infected skin Skin and skin structure infections (SSSIs), also referred to as skin and soft tissue infections (SSTIs), or acute bacterial skin and skin structure infections (ABSSSIs), are infections of skin and associated soft tissues (such as loose connective ti ...
and also assists with
inflammation
Inflammation (from la, inflammatio) is part of the complex biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants, and is a protective response involving immune cells, blood vessels, and molec ...
,
itching
Itch (also known as pruritus) is a Wikt:sensation, sensation that causes the desire or reflex to scratch. Itch has resisted many attempts to be classified as any one type of Sensory system, sensory experience. Itch has many similarities to pain, ...
, and stinging.
The
Food and Drug Administration
The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
has approved it for use for "temporary relief of minor skin irritations due to ... '
poison ivy,' 'poison oak,' '
poison sumac
''Toxicodendron vernix'', commonly known as poison sumac, or swamp-sumach, is a woody shrub or small tree growing to 9 metres (30 feet) tall. It was previously known as ''Rhus vernix''. This plant is also known as thunderwood, particul ...
,' 'insect bites,' '
athlete's foot
Athlete's foot, known medically as ''tinea pedis'', is a common skin infection of the feet caused by a fungus. Signs and symptoms often include itching, scaling, cracking and redness. In rare cases the skin may blister. Athlete's foot fungus ...
,' or 'rashes caused by soaps, detergents, cosmetics, or jewelry.'" For these applications,
over-the-counter preparations such as
Burow's solution
Burow's solution is an aqueous solution of aluminium triacetate. It is available in the U.S. as an over-the-counter drug for topical administration, with brand names including Domeboro (Moberg Pharma), Domeboro Otic (ear drops), Star-Otic, and Bor ...
are typically used,
while diluted forms are used as
gargle
Gargling is the act of bubbling liquid in the mouth. It is also the washing of one's mouth and throat with a liquid, such as mouthwash, that is kept in motion by breathing through it with a gurgling sound.
A traditional home remedy of gargling ...
s for conditions like
aphthous ulcer
Aphthous stomatitis, or recurrent aphthous stomatitis (RAS), is a common condition characterized by the repeated formation of benign and non-contagious mouth ulcers (aphthae) in otherwise healthy individuals. The informal term ''canker sore'' i ...
s of the mouth, including with
amino acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha a ...
additives to improve
palatability and
taste
The gustatory system or sense of taste is the sensory system that is partially responsible for the perception of taste (flavor). Taste is the perception produced or stimulated when a substance in the mouth reacts chemically with taste receptor ...
.
The most common use of Burow's solution is in treating
ear infections
Otitis is a general term for inflammation or infection, inner ear infection, middle ear infection of the ear, in both humans and other animals. When infection is present, it may be viral or bacterial. When inflammation is present due to fluid bui ...
including
otomycosis
Otomycosis is a fungal ear infection, a superficial mycotic infection of the outer ear canal. It is more common in tropical countries. The infection may be either subacute or acute and is characterized by malodorous discharge, inflammation ...
, though it is generally not as effective as
clotrimazole
Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock i ...
in these fungal infections.
Topical astringent powder Domeboro contains
aluminium sulfate tetradecahydrate, , and
calcium acetate monohydrate
Calcium acetate is a chemical compound which is a calcium salt of acetic acid. It has the formula Ca(C2H3O2)2. Its standard name is calcium acetate, while calcium ethanoate is the systematic name. An older name is acetate of lime. The anhydrous ...
, , and forms an aluminium acetate solution similar to Burow's solution when dissolved.
Domeboro solutions in warm water can be used in cases of
ingrown toenail
An ingrown nail, also known as onychocryptosis from el, ὄνυξ () 'nail' and () 'hidden', is a common form of nail disease. It is an often painful condition in which the nail grows so that it cuts into one or both sides of the paronychium ...
s,
to reduce irritation and contain any infection which might be present.
Mordant
![Alizarin-Aluminium-Komplex](https://upload.wikimedia.org/wikipedia/commons/4/45/Alizarin-Aluminium-Komplex.svg)
A mordant is a substance used to set
dyes on fabrics or tissue sections by forming a
coordination complex
A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as '' ligands'' or complexing agents. ...
with the dye, which subsequently attaches to the fabric or tissue. A mordant often contains a
polyvalent metal ion, commonly aluminium or iron, as is the case with mixtures of aluminium triacetate with aluminium sulfacetate
or with basic aluminium diacetate.
Aluminium triacetate mordants have been used with
cotton
Cotton is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure cellulose, and can contain minor pe ...
, other
cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell w ...
-based fibres,
and
silk
Silk is a natural protein fiber, some forms of which can be woven into textiles. The protein fiber of silk is composed mainly of fibroin and is produced by certain insect larvae to form cocoons. The best-known silk is obtained from the ...
.
They have also been combined with
ferrous acetate
Iron(II) acetate is a coordination complex with formula Fe(O2CCH3)2. It is a white solid, although impure samples can be slightly colored. A light green tetrahydrate is also known, which is highly soluble in water.
Preparation and structure
Ir ...
to produce different colours.
![Alizarin CaAl Komplex](https://upload.wikimedia.org/wikipedia/commons/a/a3/Alizarin_CaAl_Komplex.svg)
In the case of the dye
alizarin
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Historic ...
(1,2-dihydroxy
anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoan ...
, ), mordanting was hypothesised to involve the formation of a dianion of alizarin. This would form a five-coordinate aluminium complex, , which can take up water to form a hydrate with a six-coordinate aluminium-centred dianion, . The proposal was based on
infrared spectroscopic data, and was subsequently challenged by work suggesting a structure with two bridging hydroxyl ligands connecting a dinuclear core, , with two alizarin
moieties each
chelating
Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...
to each aluminium centre.
The structure was proposed by Soubayrol ''et al.'' based on
27Al NMR spectroscopy and
electrospray ionisation
Electrospray ionization (ESI) is a technique used in mass spectrometry to produce ions using an electrospray in which a high voltage is applied to a liquid to create an aerosol. It is especially useful in producing ions from macromolecules bec ...
mass spectrometry evidence.
They reported that the degree of hydration was dependent on the identity of the counter-ion, with the sodium salt being a stable tetrahydrate with a monohydrate being formed from
potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash.
Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...
. These were distinguishable based on their
chemical shift
In nuclear magnetic resonance (NMR) spectroscopy, the chemical shift is the resonant frequency of an atomic nucleus relative to a standard in a magnetic field. Often the position and number of chemical shifts are diagnostic of the structure o ...
s, suggesting the waters are associating with the aluminium centres or the alizarin moieties, and not behaving as is typical for
waters of crystallisation.
A related structure with calcium ions was reported in 1994, and in it the alizarins chelate to the calcium ions to form AzCaAz bridges between the aluminium centres (which are also bridged by hydroxo groups) and the aluminium centres subsequently bind to the deprotonated
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...
residues of the dye;
in the Soubayrol model, each alizarin is associated with a single aluminium cation.
As with the structure of aluminium acetate itself, the forms it takes in applications has not been resolved.
Notes
This "Ac" is not referring to the element
actinium
Actinium is a chemical element with the symbol Ac and atomic number 89. It was first isolated by Friedrich Oskar Giesel in 1902, who gave it the name ''emanium''; the element got its name by being wrongly identified with a substance An ...
. Used in this way, the convention in
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, ...
is for Ac to refer to the
acetyl group, the
radical form of which is , and OAc or AcO would be used for the
acetate radical, ,
sometimes also called "acetoxy." The acetate ion would then be AcO
−, , and acetic acid would be AcOH or HOAc. Under this convention, aluminium triacetate would be Al(OAc)
3. Publications in
geochemistry
Geochemistry is the science that uses the tools and principles of chemistry to explain the mechanisms behind major geological systems such as the Earth's crust and its oceans. The realm of geochemistry extends beyond the Earth, encompassing the ...
, however, are using Ac to refer to acetate rather than acetyl and thus in geochemistry would be written under more usual chemistry conventions as or .
References
{{Otologicals
Aluminium compounds
Acetates
Dermatologic drugs