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TRICHLORO ACETIC ACID


EC / List no.: 200-927-2
CAS no.: 76-03-9
Mol. formula: C2HCl3O2

Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. 
Salts and esters of trichloroacetic acid are called trichloroacetates.

Synthesis
Trichloroacetic acid is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst such as red phosphorus. This reaction is Hell–Volhard–Zelinsky halogenation.

CH3COOH + 3 Cl2 → CCl3COOH + 3 HCl
Another route to trichloroacetic acid is the oxidation of trichloroacetaldehyde.

History
The discovery of trichloroacetic acid by Jean-Baptiste Dumas in 1839 delivered a striking example to the slowly evolving theory of organic radicals and valences.
The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.


Trichloroacetic acid is used in the following products: laboratory chemicals, pharmaceuticals, pH regulators and water treatment products and cosmetics and personal care products.
Trichloroacetic acid is used in the following areas: health services and scientific research and development.
Other release to the environment of Trichloroacetic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).

Trichloroacetic acid is used in the following products: laboratory chemicals, coating products, non-metal-surface treatment products, washing & cleaning products and pharmaceuticals.
Release to the environment of Trichloroacetic acid can occur from industrial use: formulation of mixtures.

Trichloroacetic acid is used in the following products: laboratory chemicals, pH regulators and water treatment products, pharmaceuticals, metal surface treatment products and non-metal-surface treatment products.
Trichloroacetic acid is used in the following areas: health services, scientific research and development and formulation of mixtures and/or re-packaging.
Trichloroacetic acid is used for the manufacture of: chemicals, machinery and vehicles and fabricated metal products.
Release to the environment of Trichloroacetic acid can occur from industrial use: of substances in closed systems with minimal release, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and as processing aid.


General Description    
Trichloroacetic acid is briefly referred to as TCA. 
Trichloroacetic acid appears as colorless or white orthorhombic crystal with strong deliquescence. 
Trichloroacetic acid has slight special irritating smell with strong corrosiveness. 
The aqueous solution of TCA is strongly acidic, and the aqueous solution of 0.1 mol of solution having a pH of 1.2. 
TCA with concentration of 30% or less is difficult to be stored for a long period of time since it is gradually decomposed into chloroform, hydrogen chloride, carbon dioxide, carbon monoxide and the like. In dilute alkali, it will be hydrolyzed into chloroform and carbon dioxide. 
Formic acid is formed in concentrated alkali. 
Trichloroacetic acid is a strong corrosion products with a oral LD50 being 3320mg / kg.
Trichloroacetic acid is a strong organic acid with a dissociation constant K = 3 × 10-2. 
Trichloroacetic acid has lively chemical properties. 
Trichloroacetic acids sodium salt is easily subject to decarboxylation into chloroform. 
Trichloroacetic acid will be reduced to alcohol upon coming across LiAlH4. 
Trichloroacetic acid can have halogen replacement reaction with KBr.

Application    
Trichloroacetic acid can be used as pharmaceutical raw materials, herbicides (potassium trichloroacetate and sodium trichloroacetate, etc.), textile dyeing auxiliaries, metal surface treatment agent and acid chloride, anhydride, amide, polyester, organometallic salt, water salicylaldehyde, chlorocarboxylic acid and the raw materials of other organic synthesis. 
In addition, in medicine, it can also be used as etherifying agents and keratolytics, bile pigment reagents and protein precipitation reagents. 
In the field of biochemistry, it can be used for separation analysis of biological phosphate compounds and reagents for determination of fluoride and lipid as well as microscopic fixative, decalcification, chromatography reagents.
The product is warts agent and astringent in pharmaceutical field, mainly used as biochemical drug extractant for the extraction of many highly efficient drugs such as adenosine triphosphate, cytochrome C and placental polysaccharides.
In addition, trichloroacetic acid, together with alkaline phenol, can be used for salicylaldehyde compound synthesis by ReimerTiemann reaction. 
Trichloroacetic acid can also react with monoolefine compounds for synthesizing chlorocarboxylic acid [CCl3 (CH2CH2) nCOOH] .


Preparation    
Use acetic acid or monochloroacetic acid as raw material; gradually warm in the 100~ 150℃ in the presence of the light or catalyst (ferric chloride) for chlorination to obtain it.
Use hydrated chloral hydrate as raw material; apply oxidation reaction using concentrated nitric acid to obtain it.


Chemical Properties    
Trichloroacetic acid is a colorless crystalline solid which is used in liquid solutions.
Trichloroacetic acid, is a colorless crystalline solid. 
Trichloroacetic acid absorbs moisture from air and forms a syrup. 
Trichloroacetic acid is soluble in water with release of heat. 
Trichloroacetic acid is corrosive to metals and tissue.


Purification Methods    
Purify the acid by fractional crystallisation from its melt, then crystallise it repeatedly from dry *benzene and store it over conc H2SO4 in a vacuum desiccator. 
Trichloroacetic acid can also be crystallised from CHCl3 or cyclohexane, and dried over P2O5 or Mg(ClO4)2 in a vacuum desiccator. Trichloroacetic acid can be fractionally distilled under reduced pressure from MgSO4. 
Layne, Jaffé and Zimmer [J Am Chem Soc 85 435 1963] dried trichloroacetic acid in *benzene by distilling off the *benzene-water azeotrope, then crystallised the acid from the remaining *benzene solution. 
Manipulations should be carried out under N2. 


Trichloroacetic acid, solid is a colorless crystalline solid. 
Trichloroacetic acid absorbs moisture from air and forms a syrup. 
Trichloroacetic acid is soluble in water with release of heat. 
Trichloroacetic acid is corrosive to metals and tissue.

Trichloroacetic acid is a monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine. 
Trichloroacetic acid has a role as a metabolite, a carcinogenic agent and a mouse metabolite. 
Trichloroacetic acid is a monocarboxylic acid and an organochlorine compound. 
Trichloroacetic acid derives from an acetic acid. 
Trichloroacetic acid is a conjugate acid of a trichloroacetate.

Trichloroacetic acid, solution appears as clear colorless crystals dissolved in water. 
Corrosive to metals and tissue.

Physical Description
Trichloroacetic acid, solid is a colorless crystalline solid. 
Trichloroacetic acid absorbs moisture from air and forms a syrup. 
Trichloroacetic acid is soluble in water with release of heat. 
Trichloroacetic acid is corrosive to metals and tissue.


Uses    
Traditionally used to precipitate protein. Has been used to determine protein concentration by quantitative precipitation. Used as decalcifier and fixative, as a laboratory reagent, a herbicide, in medicine, and in microscopy.    
Trichloroacetate (TCA) is used primarily for the selective control of annual and perennial grass weeds in cropland and noncropland. 
TCA is acidic in nature and are not strongly sorbed by soils. 
Trichloroacetic acid is reported to be rapidly degraded in both soil and water by microbial processes. 
However, the breakdown of TCA occurs very slowly when incubated at 14–15 °C in acidic soils. 
timing not only accelerates this degradation but also increases the numbers of TCA-degrading bacteria.

As a reagent for albumin detection; in making herbicides. 
Trichloroacetic acid is found as a by-product after chlorination of water containing humic materials.

Trichloroacetic acid is widely used in biochemistry for the precipitation of macromolecules, such as proteins, DNA, and RNA. 
TCA and DCA are both used in cosmetic treatments (such as chemical peels and tattoo removal) and as topical medication for chemoablation of warts, including genital warts. 
Trichloroacetic acid can kill normal cells as well. 
Trichloroacetic acid is considered safe for use for this purpose during pregnancy.
The sodium salt (sodium trichloroacetate) was used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.


Modifier used for chemical, when chemical is used in a laboratory    
Byproducts of disinfection processes    
Contaminants or byproducts in drinking water, such as drugs, pesticides, and radionuclides    
Substances used for preventing, destroying or mitigating pests    
Residues found in food, typically from drugs or pesticides    
Chemicals prohibited from use (i.e. completely banned) in the ASEAN countries (Association of Southeast Asian Nations)    
Chemicals prohibited from use (i.e. completely banned) in Canada    

Methods of Manufacturing
Trichloroacetic acid is manufactured in the United States via exhaustive chlorination of acetic acid hydrolytic oxidation of tetrachloroethene, and hydrogen peroxide oxidation of chloral.

Trichloroacetic acid is produced on an industrial scale by chlorination of acetic acid or chloroacetic acid mother-liquors at 140 - 160 °C. 
If necessary, calcium hypochlorite is added as a chlorination accelerator. 
There are conflicting views concerning adding heavy metal salts as chlorination catalysts. 
Examples of catalysts that have been used are iron and copper compounds, which are precipitated with sulfuric acid or phosphoric acid if decomposition of the reaction mixture occurs; 2% phosphoric acid; and catalysts and UV light. 
Trichloroacetic acid has also been produced without catalysts. 
The crude product, containing about 95% trichloroacetic acid, is best isolated by crystallizing the melt, removing the mother-liquor with most of its impurities, and increasing the purity by centrifugation or recrystallization.

Application
Trichloroacetic acid has been used for the precipitation of sLRP (soluble circulating low density lipoprotein receptor-related protein-1) isolated from plasma.
Trichloroacetic acid has been used for the extraction of ascorbic acid from plant samples. 
Trichloroacetic acid has also been used for the preparation of ascorbate standards for ascorbate assay.
Trichloroacetic acid has been used for the precipitation of IMAC (immobilized metal ion affinity chromatography)-isolated phosphoproteins.
Traditionally used to precipitate protein. Has been used to determine protein concentration by quantitative precipitation. Used as decalcifier and fixative in microscopy.


Trichloroacetate, or trichloroacetic acid, is a strong acid prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst. 
In clinical chemistry and biochemistry, it is used as a precipitant of macromolecules including proteins, DNA and RNA. 
Trichloroacetate is also found in cosmetic treatments and topical formulations as a cauterant, which removes condyloma or warts on the skin.

Trichloroacetic Acid (TCA) is a much stronger acid than Acetic Acid, from a chemical ionization standpoint, because the electronegative Chlorine atoms draw electron density away from the carboxyl end of the molecule, creating a partial positive charge on the carboxyl group, and allowing easier removal of the positively charged Hydrogen ion, H+. 
A 0.03 Molar solution of TCA is almost 90% ionized, while a comparable strength of Acetic Acid is less than 3% ionized. 
The strong electron pull of the Chlorine atoms also gives TCA the undesirable tendency to cleave, producing Chloroform (CHCl3) and Carbon Dioxide (CO2).

Trichloroacetic acid (TCA) is a treatment for genital and anal warts caused by human papillomavirus (HPV). 
Trichloroacetic acid is a powerful chemical that kills warts by destroying the proteins in the cells. 
After repeated application, it will cause the warts to shrink and eventually disappear.


What is Trichloroacetic acid?
Trichloroacetic acid is an is an analogue of acetic acid where the three hydrogen (H) atoms of the methyl (-CH3) group are replaced by chlorine (Cl) atoms.

Trichloroacetic acid is also called Trichloroethanoic acid or Aceto-caustin. Esters and salts of trichloroacetic acid are termed as trichloroacetates. The chemical formula of Trichloroacetic acid is C2HCl3O2.

Trichloroacetic acid was discovered by Jean-Baptiste Dumas in the year 1839. Aceto-caustin in its solid form, is a crystalline solid without colour. 
Trichloroacetic acid forms a syrup by absorbing the moisture from the air. 
Trichloroacetic acid dissolves in water by liberating heat. Trichloroacetic acid is corrosive. 
Trichloroacetic acid is a powerful acid which is widely used in clinical chemistry as a protein precipitant. 
Also, it has a wide application in removing warts.


Uses of Trichloroacetic acid (C2HCl3O2)
Trichloroacetic acid is used in biochemistry to precipitate macromolecules such as DNA, RNA, and proteins.
Trichloroacetic acid is used in microscopy as a fixative and decalcifier.
Used as a reagent in organic synthesis to detect albumin, medicine, and herbicides.
Used in the chemoablation of warts.
DCA and TCA are used in cosmetic treatments.
Preparation of Trichloroacetic acid
Trichloroacetic acid is synthesized by reacting chlorine (Cl) with acetic acid (CH3COOH ) in the presence of a catalyst.

CH3COOH + 3Cl2 → CCl3COOH +3HCl

Trichloroacetic acid can also be produced by oxidation of trichloroacetaldehyde.

CCl3COOH. 
A haloacetic acid (organic). 
A colourless to white, crystalline solid with a sharp, pungent odor and very soluble in water. 
Trichloroacetic acid is an irritant and corrosive. 
Inhalation of trichloroacetic acid vapour may lead to a sore throat and cause fluid to fill the lungs (pulmonary oedema). 
Trichloroacetic acid can burn the skin and eyes. 
Blurred vision and permanent eye damage can occur. 
Long term exposures may lead to a chronic cough and bronchial pneumonia may also occur. 
Teeth may erode. 
Trichloroacetic acid is also corrosive on ingestion.

Trichloroacetic acid is used as a laboratory reagent but its main use is in the production of its sodium salt, which is used in many industries, for example, as a herbicide, etching agent and antiseptic. 
In the environment, very small quantities of trichloroacetic acid are found in chlorinated drinking water as a disinfection by product as a consequence of the reaction of chlorine with natural organic matter and bromide ions in the raw water supply (from lake, reservoirs, rivers, etc.).

What is a TCA ?
TCA is the abbreviation for trichloroacetic acid, a chemical commonly used in a wide range of chemical peels. 
TCA use a type of acid that can be customized to a variety of applications and strengths, from a quick lunch-break treatment to a complete restart for your skin.

Among the conditions that can be treated with TCA are melasma, sun damage, actinic keratoses, lentigos, texture, and rhytides.

“The strength of TCA depends on what condition is being treated,” says Dr. Klein. Medium and deep peels, including those that involve TCA, usually require a week or two of downtime as the old skin peels off.

What are TCA peels used for?
Brown spots and age spots
Sun damaged skin
Hyperpigmentation
Melasma
Acne and acne scars

How does a TCA  work?
TCA acts on keratin, a common protein found in the skin, hair, and nails. The chemical denatures the keratin proteins — in other words, removes their outer structures — which causes them to stop functioning correctly, lightening the skin and making the top layers peel off.

Chemical Background
TCA occurs naturally as a colorless crystal and is easily formulated by mixture with distilledwater. 
TCA is stable under normal conditionswith a melting point of 54 deg Celsius. 
Trichloroacetic acid is notlight sensitive; however, it is hygroscopic so the crystals should be stored in a closed container to limit its absorption of water. 
Once mixed, TCA has a shelf life of at least 2 years.


Chemical Formulations
TCA concentrations are correctly formulated using a weight-in-volume (W/V) method. Simply stated a 30% TCA solution is made by adding 30 g of TCA with enough water to make100 ml solution. 
This should not be mistaken by adding 30 g to 100 ml of water thus yielding a weaker concentration. 
Other methods including a weight in weight formulation, used in topical ointments and creams, is not accurate.
Also, dilution of existing TCA with water should not be employed as the resulting concentration is higher than one would expect. 
TCA is readily obtained in a number of concentrations from suppliers such as Delasco who specialize in its production.
Recently there have been a variety of suppliers with chemical peel kits claiming ease of use and increased efficacy. 
These proprietary kits vary from the vehicle used in delivering the TCA to having color indicators to inform the physician of a peel’s completion. 
Caution should be used when using such kits as many times the physician loses the ability to easily assess the degree of frosting and in turn the depth and safety of the chemical peel.

Trichloracetic acid is used in protein concentration determination by quantitative precipitation and as a decalcifier and fixative in microscopy. 
Trichloracetic acid, the solution is primarily used with the Fouchet-Van Gieson kit. 
Trichloracetic acid is used for simultaneous visualization of bilirubin and collagen in histological samples. 
Bilirubin is a yellow-brown pigment created as a result of haemoglobin degradation. 
Haemoglobin degradation occurs in the bone marrow, spleen, and liver. 
In the case of patients that suffer from hepatitis, bilirubin builds up in the form of a thrombus in bile ducts and in the form of granules in hepatocytes and in the cytoplasm of Kupffer cells. 
The pigment is insoluble in water and in water fixatives. However, in case of prolonged exposure to formalin fixatives, it may turn green. 
The colour that is created during staining using the Trichloracetic acid is due to the strong redox reaction of the complex and subsequent conversion to biliverdin (green). 

Trichloroacetic acid is mixed from absolutely fresh TCA crystals, using proper weight/volume calculations, for standardization of potency. Locally-made TCA is subject to variation.

Trichloroacetic acid is often made from old crystals that have lost some of their potency, or by using incorrect formulas, such as weight/weight or other non-standard calculations.

Trichloroacetic Acid, Crystal, Reagent, ACS, also known as TCA, is used in biochemistry to help the precipitation of macromolecules. 
Trichloroacetic acid is also used in the cosmetic industry as a chemical peel and also as a wart remover. 
As an ACS grade Reagent, Spectrum Chemical manufactured trichloroacetic acid is used as the quality standard against which other substances are graded and has met the toughest regulatory standards for quality and pureness.

Trichloroacetic acid (also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Trichloroacetic acid is a strong acid, comparable to sulfuric acid.

Trichloroacetic acid is widely used in biochemistry for the precipitation of macromolecules such as proteins, DNA and RNA. Trichloroacetic acids sodium salt is used as a weedkiller.

Solutions containing trichloroacetic acid as an ingredient are used for tattoo removal and the treatment of warts, including genital warts, but it is not recommended for self usage. 
Trichloroacetic acid can kill normal cells as well. 
Trichloroacetic acid is considered safe for use for this purpose during pregnancy

Formal Chemical Name (IUPAC)
2,2,2-trichloroacetic acid

Trichloroacetic acid is an acetic acid analogue commonly used to precipitate proteins, DNA and RNA. 
In the presence of SDS (sc-24950) Trichloroacetic acid will precipitate proteins which can then be quantified by the Lowry method. 
The compound has also found uses as a decalcifier and fixative in microscopy, in protein sequencing, detecting albumin and organic synthesis. 


IUPAC NAMES
2,2,2-trichloroacetate
2,2,2-Trichloroacetic acid
2,2,2-trichloroacetic acid
Acido tricoloacetico
TCA
TCA (ISO)
Trichloressigsäure
Trichloroacetic Acid
Trichloroacetic acid
trichloroacetic acid
Trichloroacetic acid
trichloroacetic-acid-
Tricloacetic acid

SYNONYMS 
Deblock trichloroacetic acid solution
TRICHLOROACETIC ACID extrapure
RARECHEM AL BO 0072
Aceticacid,trichloro-
Aceto-Caustin
Acide trichloracetique
acidetrichloracetique
acidetrichloracetique(french)
acidetrichloracetique(solide)
acidetrichloracetique(solutions)
Acido tricloroacetico
acidotricloroacetico
Amchem Grass Killer
amchemgrasskiller
CCl3COOH
Farmon TCA
Konesta
Kyselina trichloroctova
kyselinatrichloroctova
NA TA
nata
natal
sodiumtcasolution
tecane
TKhU
TKhUK
Trichloorazijnzuur
Trichloracetic acid
trichloraceticacid
Trichloressigsaeure
trichlorethanoicacid
trichloro-aceticaci
trichloroaceticacid(non-specificname)
trichloroaceticacid,solution
trichloroaceticacidsolid
trichloroaceticacidsolutions
Trichloroethanoic acid
trichloroethanoicacid
trichloromethanecarboxylicacid
Varitox
Trichloroacetic acid, 99%, flakes, extra pure
Trichloroacetic acid, 99+%, for analysis ACS
Trichloroacetic acid, for analysis ACS
TkhV
TkhVk
TRICHLOROACETIC ACIDANALYTICAL GRADE
Trichloroacetic acid solution,TCA
Trichloroacetic acid, extra pure, USP, BP
Trichloroacetic acid, reagent grade, ACS
Trichloroacetic acid, solution 3% w/v, extra pure
Trichloroacetic acid, solution 20% w/v, extra pure
TCA (Trichloroacetic acid)
Trichloroacetic acid,99%,extra pure,flakes
Deblock, trichloroac
Deblock, trichloroacetic acid in dichloromethane
Trichloroacetic acid, 99%, extra pure
Trichloroacetic acid, flakes, extra pure, 99% 1KG
Trichloroacetic acid, flakes, extra pure, 99% 500GR
 

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