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1,2-Benzendioic acid = Phthalic acid
CAS Number : 88-99-3
EC Number: 201-873-2
Phthalic acid is an aromatic dicarboxylic acid with the formula C6H4(CO2H)2.
Phthalic acid is an isomer of isophthalic acid and terephthalic acid.
Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commercial chemical produced on a large scale.
Phthalic acid is one of the three isomers of benzenedicarboxylic acid, the others being isophthalic acid and terephthalic acid.
Producing
Phthalic acid is produced by the direct catalytic oxidation of naphthalene or ortho-xylene to phthalic anhydride followed by hydrolysis of the anhydride.
Phthalic acid was first obtained by the French chemist Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride.
Believing that the resulting substance was a derivative of naphthalene, he named it "naphthalic acid".
After Swiss chemist Jean Charles Galissard de Marignac determined the correct formula, Laurent gave it its current name.
Production methods in the nineteenth century included the oxidation of naphthalene tetrachloride with nitric acid, or better, the oxidation of the hydrocarbon with fuming sulfuric acid using mercury or mercury(II) sulfate as a catalyst.
synthesis
Naphthalene yields phthalic acid in oxidation with potassium permanganate or potassium dichromate[citation needed].
Reactions and uses
phthalic acid crystals
Phthalic acid is a dibasic acid with pKas of 2.89 and 5.51.
Phthalic acid monopotassium salt, potassium hydrogen phthalate, is a standard acid in analytical chemistry.
Typically, phthalate esters are prepared from widely available phthalic anhydride.
Reduction of phthalic acid with sodium amalgam in the presence of water gives the 1,3-cyclohexadiene derivative.
Safety
The toxicity of phthalic acid to phthalic acid is moderate with an LD50 (mouse) of 550 mg/kg.
biodegradation
Phthalic acid bacteria Pseudomonas sp. P1 degrades phthalic acid.
Names
Preferred IUPAC name
Benzene-1,2-dicarboxylic acid
other names
1,2-Benzendioic acid
phthalic acid
Benzene-1,2-dioic acid
ortho-phthalic acid
identifiers
CAS Number : 88-99-3
chebi chebi:29069
Chemical Spider : 992
ECHA Information Card :100.001.703
EC Number: 201-873-2
PubChem Client ID: 1017
UNII : 6O7F7IX66E
CompTox Control Panel (EPA) : DTXSID8021484
Features
Chemical formula: C8H6O4
Molar mass :166.132 g/mol
Appearance : white solid
Density :1.593 g/cm3, solid
Melting point : 207 °C (405 °F; 480 K)[3]
Solubility in water :0.6 g / 100 mL [1]
Acidity (pKa) : 2.89, 5.51[2]
Magnetic susceptibility (χ): -83.61·10−6 cm3/mol
General description
Phthalic acid (PA) is the final metabolite of phthalic acid esters (PAEs).
The interaction between phthalic acid and well-ordered MgO(100) (magnesium oxide) thin films was investigated.
Phthalic acid activity of activated carbon suspended in aqueous medium was analyzed for PA adsorption.
Phthalic acid degradation of PA by oxidation by electro-Fenton (EF) and solar photoelectro-Fenton (SPEF) has been reported.
Application
Phthalic acid can be used as an additive to the mobile phase to increase the detection sensitivity of amino acids (AAs) by hydrophilic interaction liquid chromatography (HILIC) coupled with electrospray ionization tandem mass spectrometry (ESI-MS/MS).
Packaging
100 g in poly bottle
1 kg in poly bottle
Catalog Number 822298
Synonyms Benzene-1,2-dicarboxylic acid
Description Phthalic acid
Product information
CAS number 88-99-3
EC number 201-873-2
Peak Formula C₈H₆O₄
Chemical formula C₆H₄(COOH)₂
Molar Mass 166.13 g/mol
HS Code 2917 39 95
Boiling point 289 °C (1013 hPa) (decomposition)
Density 1.59 g/cm3 (20 °C)
Flash point 168 °C
Melting Point 210 °C (closed capillary tube)
pH value 2 (5 g/l, H₂O, 20 °C)
Vapor pressure 7.8 hPa (191 °C)
Bulk density 960 kg/m3
Resolution 5.74 g/l
Synonyms: 1,2-Benzenedicarboxylic acid
Linear Formula:C6H4-1,2-(CO2H)2
CAS Number:88-99-3
Molecular Weight: 166.13
Beilstein:608199
EC Number: 201-873-2
MDL number:MFCD00002467
PubChem Item ID: 24898471
NAKRIS:NA.21
Phthalates are widely used in many personal care products, cosmetics and plastics (softening products made from these materials, especially vinyl plastics), paper coating, paints and adhesives.
Although the Campaign for Safe Cosmetics reveals the presence of phthalates in nail polish as an ingredient only, phthalates can be detected in many of the products evaluated, even products that do not contain phthalates on their labels.
Shampoo, body deodorant, body wash, hair spray and hair gel are examples.
Although phthalate levels in bottled waters have been found to be low, overconsumption of such waters raises concerns.
It is recommended to pay special attention to the storage conditions of phthalic acid in bottles.
Surprisingly, nutritional supplements for enteric-coated pharmaceutical tablets and viscosity control agents also contain phthalates.
DEHP is commonly applied in medical devices, including cardiac catheters, endotracheal tubes, and some implanted devices, while DINP is commonly found in wires, cables, hoses, and plastic toys.
Unfortunately, plastic containers such as food trucks are the main source of DEHP, where phthalates are physically dissolved in the plastic and not by chemical bonding.
It is claimed that phthalic acid, phthalates, was never used in the marketing of plastic food packaging in the United States.
According to the literature in the Pediatric Environmental Health Specialty Units program, some recommendations should be kept in mind to prevent the release of phthalates from plastic containers: Food/beverage and plastic clean packaging should not be heated in the microwave in plastic containers, nor should plastics be stored. placed in the dishwasher.
Safe alternatives such as glass or polyethylene plastics and phthalate-free labels are highly recommended.
Phthalic acid is an aromatic dicarboxylic acid with the formula C6H4(COOH)2.
Phthalic acid is mainly used in its anhydride form to produce other chemicals such as dyes, perfumes, saccharin, phthalates and many other useful products.
Phthalic acid results from exposure to these phthalate products when present in tissues or biological fluids.
Phthalate is an environmental chemical of high public concern, as reports of potential risks to male reproductive health (PMID 16804814) are significantly associated with the reduction of sperm concentration in male urine to pesticide concentration (PMID 16804812).
Within the reproductive tract, the male is extremely sensitive to the effects of anti-androgens during development, as it depends on the synthesis and action of androgens for masculinization of the male reproductive tract.
The ability of phthalates to suppress androgen synthesis during development and to induce testicular dysgenesis with cryptorchidism and hypospadias has raised significant concern.
Phthalic acid is an aromatic dicarboxylic acid with the formula C6H4(CO2H)2. It is an isomer of isophthalic acid and terephthalic acid.
Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commercial chemical produced on a large scale.
Phthalic acid is one of the three isomers of benzenedicarboxylic acid, the others being isophthalic acid and terephthalic acid.
Phthalic acid, also called 1,2-benzenedicarboxylic Acid, is a colorless, crystalline organic compound usually produced and sold in the form of its anhydride.
Phthalic acid annual production of phthalic anhydride exceeded 1,000,000 metric tons in the late 20th century; Most were used as a component of polyesters, including alkyd resins (tools for paints and enamels) and simple esters used as plasticizers for polyvinyl chloride and other polymers.
Smaller amounts were consumed in the production of anthraquinone (a dye intermediate), phenolphthalein (a laxative and acid-base indicator), and phthalocyanine pigments.
Personal protection: respirator with particulate filter adapted to the airborne concentration of the substance.
Sweep up spilled material into closed containers. If appropriate, moisten first to prevent dusting.
Wash off the remainder with plenty of water.
Formula: C8H6O4 / C6H4(COOH)2
Molecular mass: 166.1
decomposes at 191°C
Relative density (water = 1): 1.6
Solubility in water, g/100ml at 25°C: 0.625 (poor)
Relative vapor density (air = 1): 5.7
Flash point: 168°C cc
Octanol/water partition coefficient in log Pow: 0.73
Phthalic acid is a simple dicarboxylic acid organic compound, a benzoic acid derivative with an additional ortho-carboxylic acid.
Phthalic acid is most commonly discussed in relation to its ester derivatives or Phthalic anhydride (sc-203189), both of which are used as industrial plasticizers in the manufacture of polyvinylchlorides and other plastics.
Phthalic acid esters are thought to function as endocrine disruptors with detrimental effects on development in animals.
The phthalic acid ester derivative di(2-ethylhexyl)phthalate has been specifically shown to interfere with the conversion of tryptophan to endogenous niacin in rats.
The monopotassium salt of phthalic acid (KHP, sc-203363) is useful as a primary acid standard in analysis and in the preparation of volumetric solutions.
Phthalates are dialkyl or alkyl aryl ester derivatives of 1,2-benzenedicarboxylic acid.
They are often used as plasticizers to improve the flexibility and durability of polyvinyl chloride (PVC)-based plastics, and less important phthalate applications include ink components, adhesive materials, lacquers, sealants and packaging materials, as well as additives in other types of cosmetics. .
Phthalates are not chemically bound to plastic, so it is suspected that most of the phthalates in the environment come from phthalate-containing products and the adsorption performance of dimethyl phthalate (DMP).
Phthalates can migrate from a plastic material to the environment with which they are in contact.
Various factors such as polymer properties, amount of plasticizer, plasticization process, temperature and contact area can affect their migration.
As a type of endocrine disrupting chemical, phthalic acid esters (PAEs) exhibit estrogenic effects and various biological toxicities.
Research has shown that PAEs can reduce fertility and pregnancy rates and increase miscarriages and other pregnancy complications in humans and animal models.
Some PAEs and their metabolites produce reproductive and developmental toxicities in laboratory animals.
Toxicological evaluation of phthalic acid of these chemicals has shown that low molecular weight phthalates such as diethyl phthalate (DEP) can cause eye, nose and throat irritation.
However, several larger phthalate molecules, such as Bis(2-ethylhexyl) phthalate (DEHP), Benzyl butyl phthalate (BBP), Diisononyl Phthalate (DINP), and Diisodecyl phthalate (DIDP), are suspected to be cancer-causing agents in humans. it can harm the development of the liver and kidneys, reproductive organs, and inhibit development by acting as a mimic of the sex hormone estrogen.
Phthalic acid PAEs have become one of the major pollutants in wastewater, and increased awareness of phthalate ester toxicity has raised concerns about the fate of such pollutants and their removal from the environment.
The phthalic acid properties, toxicity and removal methods of PAEs have been reviewed by various authors.
Phthalic acid is the main degradation product of phthalic acid anhydride and various phthalate esters and exists in solution as neutral acid or negatively charged anions, hydrogen phthalate (H-PA−) and phthalate (PA2−), depending on pH. The value of H2-PA is 2.9 and 5.4.
The main objective of this study was to remove phthalic acid (also known as orthophthalic acid, OPA) and isophthalic acid (IPA) in aqueous solution using a strong basic anion exchange resin.
The effects of various factors such as resin dosage, initial solution pH and reaction temperature on OPA and IPA removal were systematically investigated.
Next, uptake kinetics were studied to understand the resin uptake process and analyze the rate control step.
In addition, the desorption performance of the resin was evaluated.
Phthalic acid esters (PAEs) are common plasticizers added to polymeric materials to improve their flexibility and processability.
PAEs are widely used in cosmetics, food packaging, building materials, medical supplies, home furnishings, etc., due to their characteristic properties such as good insulation, high strength, excellent corrosion resistance, low cost. It is widely used in many consumer products, including and ease of manufacture.
The current global production of PAE for phthalic acid is estimated at 300 million tonnes and is expected to reach 500 million tonnes by 2050, mostly disposable products.
In addition, China has become the world's largest producer, consumer and importer of plasticizers, accounting for approximately 42% of world consumption in 2017.
Di(2-ethylhexyl) phthalate, one of the most abundantly produced phthalates, accounts for one-third and 80% of phthalates produced in the European Union and China, respectively. With such extensive application of phthalate-containing products, PAEs have received increasing attention as environmental and biomedical pollutants that can invisibly enter the human body through airborne contamination, skin contact, and the food chain, posing potential health and ecological system threats.
In fact, a number of studies have been conducted to investigate the toxicity of PAEs to humans and/or animals.
Epidemiological studies have found that early phthalate exposure can cause significant neurodevelopmental damage.
Some PAEs have proven to have reproductive and developmental toxicities in animals and are suspected of causing endocrine disrupting effects in humans.
PAEs were also harmful to aquatic organisms. Di-n-butyl, diethyl phthalate and their mixtures were found to effectively activate the antioxidant system of zebrafish embryos, resulting in immunotoxicity and neurotoxicity.
Zhao et al. (2014) reported that di-n-butyl and di(2-ethylhexyl) phthalate disrupted the antioxidant system of carp, while co-exposure to these two compounds exacerbated this change.
Much of the literature published so far has focused on the detection methods, contamination distribution and toxicological hazards of PAEs. However, the natural sources of various PAEs are rarely studied.
The first report of phthalic acid as a natural substance was by Schmid and Karrer (1945) and since then more than 50 different PAE derivatives have been reported from different taxonomic groups including bacteria, actinomycetes, fungi, fern, higher plants. , and even animals.
However, in many cases it is rather complicated to determine whether these compounds come from synthesized materials that subsequently cause pollution of the air, water or soil, or whether they can be produced by plants and microorganisms themselves. .
The purpose of this review is to summarize the plant and microorganism origin of PAEs to better understand their possible sources: synthesized chemicals or naturally occurring secondary metabolites?
2. Physicochemical Properties and Applications of PAEs
Phthalic acid esters (1,2-benzenedicarboxylic acid dialkyl or alkyl aryl esters), often called PAEs, phthalate esters or simply phthalates, are an important group of phthalic acid derivatives synthesized by Fischer esterification from phthalic anhydride and specific alcohols.
PAEs based on hydrogen bonding and van der Waals force interconnection are hydrophobic compounds with log Kow values ranging from 1.6 to 12.
Most phthalate esters are colorless liquids with low volatility, high boiling point, and poor solubility in water, but are soluble in organic solvents and oils.
The overall chemical structure of these esters consists of a solid planar aromatic ring and two malleable nonlinear fatty side chains.
Phthalic acid two side chain groups may or may not be the same and there are about 30 different types of side chains ranging from dimethyl phthalate to tridecyl ester.
Due to the prevalence of phthalate esters in the biosphere and potential hazards to ecosystem functioning and public health, six PAEs, including dimethyl phthalate, diethyl phthalate, dimethyl, have been listed as priority pollutants by the United States Environmental Protection Agency and the European Union. n-butyl phthalate, butyl benzyl phthalate, di(2-ethylhexyl) phthalate and di-n-octyl phthalate.
The physicochemical properties and common applications of phthalic acid phthalate esters are summarized in Table 1 and Figure 1.
Toxins 13 00495 g001 550Figure 1.
Phthalic acid application of six PAEs listed as priority pollutants.
PAEs are a class of lipophilic chemicals commonly used as plasticizers and additives in the plastics manufacturing industries to improve the mechanical extensibility and flexibility of various products such as plastics, dyes, and synthetic fibers.
Lower molecular weight phthalates such as dimethyl phthalate, diethyl phthalate, and di-n-butyl phthalate are widely used in cosmetic and personal care products; dimethyl phthalate and diethyl phthalate allow perfume fragrances to evaporate more slowly, making the fragrance lasting longer, and a small amount of di-n-butyl phthalate can make nail polish resistant to breakage.
Di-n-butyl phthalate is also used in cellulose esters, printing inks, latex adhesives and insect repellents.
Higher phthalate molecules such as di(2-ethylhexyl) phthalate, diisononyl phthalate and butyl benzyl phthalate have a wide application in the polymer industry as plasticizers to improve flexibility, processability and general use properties, and about 80% PAEs are used for this purpose. .
The phthalic acid stability, fluidity and low volatility of these compounds make them well suited for the production of PVC and other resins such as polyvinyl acetates and polyurethanes.
One of the most common phthalate plasticizers, di(2-ethylhexyl) phthalate has many useful applications in numerous consumer products, merchandise, and building materials.
Diisononyl phthalate is commonly used in garden hoses, pool linings, floor tiles, linoleum and toys. In addition, as a component of materials, butyl benzyl phthalate is widely used in vinyl flooring, synthetic leather, inks and adhesives.
The phthalates are not covalently bound to the polymer matrix, but rather generally remain present as a freely movable and leachable phase; therefore, they may disappear from the soft plastic over time and be released into the environment during production and manufacturing.
It is not surprising that phthalates are often found in freshwater lakes and oceans, urban and suburban soil, the atmosphere and sediments.
This et al. (2020) summarized six representative phthalate concentrations from papers published over the past two decades (2000-2019) to analyze the pollution properties of phthalates worldwide and found that their mean concentrations in precipitated dust were 500.02 μg/g, 580.12 in North America. In µg/g Europe and 945.45 µg/g Asia, DEHP is the predominant phthalate with mean and median values of 615.78 µg/g and 394.03 µg/g, respectively; The mean concentration of six representative phthalates in indoor air was 598.14 ng/m3 in North America, 823.98 ng/m3 in Europe and 1710.26 ng/m3 in Asia.
Phthalic acid Properties
Melting point:210-211 °C (dec.) (lit.)
Boiling point:214.32°C (rough estimate)
Density :1.59 g/cm3 at 15 °C
vapor pressure: 7.8 hPa (191 °C)
refractive index: 1.5100 (estimated)
Flash point:168 °C
retention degree. : Store below +30°C.
Solubility: methanol: 0.1 g/mL, clear
form: Powder
pka:2.89(at 25 ℃ )
White color
PH2: (5g/l, H2O, 20 ℃ )
Solubility in Water: 7 g/L (25 ºC)
Price: 14,7371
BRN:608199
Stability: Stable. flammable. Incompatible with strong oxidizing agents.
InChIKeyXNGIFLGASWRNHJ-UHFFFAOYSA-N
Indirect Additives Used in Food Contact Materials: O-PHTALIC ACID
CAS Database Reference : 88-99-3(CAS Database Reference)
FDA 21 CFR: 175.105
Phthalic acid is an organic compound derived from benzene and used in the manufacture of dyes, perfumes, medicines and synthetic fibers.
Phthalic acid has the chemical formula C6H4(CO2H)2 and contains a six-carbon benzene ring with two carboxylic acid groups (-COOH) attached.
Phthalic acid IUPAC name is 1,2-,benzenedicarboxylic acid.
Phthalic acid is a colorless, crystalline organic compound often produced and marketed as anhydride.
In the late twentieth century, annual production of phthalic anhydride exceeded 1,000,000 metric tons; the majority was used as a component of polyesters such as alkyd resins.
Smaller amounts have been used in the manufacture of anthraquinone (a dye intermediate), phenolphthalein (a laxative and acid-base indicator), and phthalocyanine pigments.
Phthalic Acid is the main chemical compound applied as anhydride to create chemicals such as dyes, phthalates, saccharin, perfumes and many other useful products.
The boiling point of phthalic acid is 289 °C (1013 hPa) (decomposition).
Phthalic Acid Structure
The structure of phthalic acid is very similar to that of aromatic carboxylic acid and is therefore known as one of the simplest acids of this family.
Since phthalic acid is chemically known as benzene-1,2-dicarboxylic acid, it is clear from its name that it consists of a benzene ring linked by two carboxyl groups at position 1 and 2 of the phthalic acid structure, or in other words, an additional benzene ring. carboxyl group attached to benzoic acid in the ortho position.
Therefore, the chemical formula of phthalic acid or phthalic acid formula is C6H4(CO2H)2; this means that it is a six-carbon ring with a double bond alternating to one of its carbon atoms with a carboxyl group (-COOH), making it aromatic in nature. aromatic benzene ring and other carboxyl group (-COOH) in the ortho position.
This acid is very stable by nature and is considered a weak acid, but reacts strongly with strong bases. Phthalic acid The structure of phthalic acid is shown below.
Phthalic Acid Production
Phthalic acid is produced following the direct catalytic oxidation of naphthalene or ortho-xylene to phthalic anhydride and hydrolysis of anhydride.
French chemist Auguste Laurent developed phthalic acid by oxidizing naphthalene tetrachloride in 1836.
He named the resulting product "naphthalic acid" because he thought it was a naphthalene derivative.
Laurent gave it its current name after Swiss chemist Jean Charles Galissard de Marignac determined its correct formula. The oxidation of naphthalene tetrachloride with nitric acid, or better still, the oxidation of the hydrocarbon with fumed sulfuric acid using mercury or mercury(II) sulfate as a catalyst was a popular manufacturing process in the nineteenth century.
Phthalic Acid Reactions
It is a dibasic acid with pKas of 2.89 and 5.51. In analytical chemistry, potassium hydrogen phthalate, a monopotassium salt, is a regular acid.
Typically, phthalate esters are made from readily available phthalic anhydride.
The 1,3-cyclohexadiene derivative is produced by reduction of phthalic acid with sodium amalgam in the presence of water.
Phthalic Acid Formula
Phthalic acid is a benzene dicarboxylic acid with two carboxy groups in the ortho places.
Phthalic acid acts as a xenobiotic metabolite in humans. It is phthalate(1-) and phthalate conjugate acid.
The phthalic acid structure is shown in the diagram below.
Phthalic Acid Uses
There are several uses of phthalic acid:
Phthalic acid is mainly used in its anhydride form to produce other chemicals such as dyes, perfumes, saccharin, phthalates and many other useful products.
Plasticizers such as phthalic acid esters (phthalates) are used in a wide variety of consumer goods, commodities and building materials.
As a result, phthalates can be present in high concentrations in both the air and dust of people's homes and workplaces.
Phthalates are also commonly found pollutants in food and the environment.
Can Phthalic Acid Be Dangerous?
Irritation of the skin, eyes, mucous membranes and respiratory tract may occur after exposure to this compound.
Phthalic acid can cause narcosis in high concentrations.
Phthalic acid is a carboxylic acid.
Extreme heat has a negative effect on this chemical.
Anhydrite Phthalic: Meaning, Uses and Formula
The organic compound is phthalic anhydride, formula - C8H4O3.
Phthalic acid is the anhydride of phthalic acid.
The most common commercial form of phthalic acid is phthalic anhydride.
Phthalic acid was the first commercially available dicarboxylic acid anhydride.
Phthalic anhydride is a colorless to white shiny solid that comes in the form of a needle and has a faint odour.
Irritating to skin and moderately harmful if inhaled or swallowed.
The oxidation of naphthalene in concentrated sulfuric acid in the presence of mercury sulfate was the first step in the production of phthalic anhydride.
The off-gases are cooled before passing to switch condensers, where the phthalic anhydride solidifies on the walls and is recovered by sublimation.
Anhydrite phthalic is used in a wide variety of applications worldwide, from the plastics industry to resin synthesis, agricultural fungicides and amines.
Phthalic acid is currently made by oxidizing o-xylene and naphthalene in the steam process.
This is the structure of phthalic anhydride:
Phthalic Anhydride Reactions
The reaction of phthalic anhydride, or acid, with alcohol, produces phthalic acid esters, which are used in diffusion pumps and to replace mercury in manometers.
Diethyl and dihexyl esters are widely used in this application. Insect repellents such as dimethyl phthalate are effective.
Phthalic anhydride is widely used in the production of what are called alkyd resins. Polyesters of acids with two carboxyl groups and polyhydric alcohols form these resins.
The acidic imino hydrogen atom of phthalic acid between the two carbonyl groups causes the phthalimide to form metallic salts.
Phthalimide phthalic acid potassium salt, as you may remember, is used in Gabriel's amine and amino acid synthesis.
As mentioned earlier, the Hofmann degradation of phthalimide provides a convenient method for obtaining anthranilic acid.
When phthalic anhydride is cold treated with alkaline hydrogen peroxide, acidified monoperphthalic acid is formed.
What Does Phthalic Acid Mean?
Phthalic acid (PA) is a chemical substance, an aromatic dicarboxylic acid with the chemical formula C6H4(COOH)2.
Phthalic acid is primarily used to make corrosion inhibitors applied to metal substrate surfaces.
Corrosionpedia Explains Phthalic Acid
Phthalic acid is produced in end-stage metabolites of phthalic acid esters.
Phthalic acid interacts with magnesium oxide films to form the following inhibitory mechanisms on a substrate metal to be protected:
Absorption by chemical adsorption process, which together with metallic ions forms a protective film
Increased resistance of a metal to environmental factors by self-leveling of individual protective oxides
Reaction with a potentially corrosive substance in the presence of water
Care should be taken when using phthalic acid as it is very corrosive and can cause irritation to human skin, eyes and respiratory tract.
CAS Number: 88-99-3
Other(deleted CASRN): 4401-64-3
ECHA EINECS - REACH Pre-Registration: 201-873-2
FDA UNII: 6O7F7IX66E
Nikkaji Web: J3.547E
Beilstein Number: 0608199
MDL: MFCD00002467
XlogP3: 0.70 (estimated)
Molecular Weight: 164.11668000
Formula: C8 H4 O4
BioActivity Summary: listing
Decarboxylation of phthalic acids Bacillus sp. strain FO, a mixed culture of marine ON-7 and Pseudomonas testosteroni.
Phthalic acid mixed culture ON-7 quantitatively converted phthalic acid to benzoic acid when grown anaerobically on phthalate but incubated aerobically with chloramphenicol.
Substituted phthalic acids were also decarboxylated: from 4,5-dihydroxyphthalic acid to protocatechic acid; from 4-hydroxyphthalic and 4-chlorophthalic acids to 3-hydroxybenzoic and 3-chlorobenzoic acids, respectively; and 3-fluorophthalic acid to 2- and 3-fluorobenzoic acids.
Bacillus sp. The FO strain produced similar results except that 4,5-dihydroxyphthalic acid was not metabolized and both 3- and 4-hydroxybenzoic acids were produced from 4-hydroxyphthalic acid. P. testosteroni decarboxylated 4-hydroxyphthalate (3-hydroxybenzoate) and 4,5-dihydroxyphthalate, but not phthalic acid and halogenated phthalates.
Thus, P. testosteroni and mixed culture ON-7 had 4,5-dihydroxyphthalic acid decarboxylase, which metabolizes 4,5-dihydroxyphthalic acid previously described in P. testosteroni and specifically decarboxylates 4-hydroxyphthalic acid to 3-hydroxybenzoic acid. .
Phthalic acid mixed culture ON-7 and Bacillus sp. The FO strain also contained a novel decarboxylase that metabolizes phthalic acid and halogenated phthalates, but not 4,5-dihydroxyphthalate and randomly decarboxylated 4-hydroxyphthalic acid.
It is recommended that phthalic acid decarboxylation of phthalic acid involves initial reduction to 1,2-dihydrophthalic acid followed by oxidative decarboxylation to benzoic acid.
Phthalic acid (IUPAC systematic name: benzene-1,2-dicarboxylic acid) is an aromatic dicarboxylic acid with the formula C6H4(COOH)2.
Phthalic acid is an isomer of isophthalic acid and terephthalic acid.
uses
Phthalic acid is mainly used in its anhydride form to produce other chemicals such as dyes, perfumes, saccharin, phthalates and others.
History
Phthalic acid was obtained by the French chemist Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride, and he named it naphthalene acid, believing that the resulting substance was a naphthalene derivative.
Swiss chemist Jean Charles Galissard de Marignac determined the formula and showed that Laurent's assumption was wrong, so Laurent gave it its current name.
Production methods in the nineteenth century included the oxidation of naphthalene tetrachloride (prepared from naphthalene, potassium chlorate, and hydrochloric acid) with nitric acid, or better, the oxidation of the hydrocarbon with fuming sulfuric acid using mercury or mercury(II) sulfate as a catalyst. .
Direct catalytic oxidation of naphthalene to phthalic anhydride followed by hydrolysis of anhydride is one of the new production methods.
chemical
Phthalic acid decomposes into water and phthalic anhydride to form white crystals that melt at 210 °C.
Heating with excess lime produces benzene.
Phthalic acid (and anhydride) is largely used in the color industry (see phenolphthalein).
Phthalic acid esters (PAEs) are a very important organic chemical product, mainly used as a plasticizer and softener for polyvinyl chloride (PVC) and other rubber and plastic materials in industry.
However, PAEs are also a common organic pollutant and are commonly found in the atmosphere, water, soil, biology, and food.1
And it enters the human body in various ways and can potentially harm human health or even endanger people's lives.
Therefore, the government should pass the relevant laws and regulations, research the new non-toxic and environmentally friendly plasticizer, take preventive and restorative measures to protect the ecological environment and human health.
Phthalic Acids or Benzene Dicarboxylic Acids, CmH 4 (CO2H) 2.
There are three isomers:
(1) ortho or phthalic acid;
(2) meta or isophthalic acid;
(3) para or terephthalic acid.
Phthalic acid was obtained by Laurent by the oxidation of naphthalene tetrachloride in 1836, believing it to be a derivative of naphthalene, which he called naphthalene acid; Marignac determined the formula and showed that Laurent's assumption was wrong, and Laurent thereupon gave it its current name.
Phthalic acid is produced by oxidizing naphthalene tetrachloride (prepared from naphthalene, potassium, chlorate and hydrochloric acid) with nitric acid, or better still, by oxidizing the hydrocarbon with smoked sulfuric acid, using mercury or mercury sulfate as a catalyst (German patent 91). , 202).
Phthalic acid also results in the oxidation of ortho xxi. 18 benzene derivatives.
Phthalic acid forms white crystals and dissolves at 213°, decomposing to water and phthalic anhydride; the second forms long white needles that melt at 128° and boil at 284°.
It gives benzene when heated with excess lime; When calcium phthalate is heated to 330°-350° with a molecule of lime, calcium benzoate is formed.
The acid (and anhydride) is largely used in the color industry (see Fluorescein; Phenol Phthalein).
Phthalyl chloride, C6H4(COC1)2 or C6H4(CCl2)(CO)0, formed by heating anhydrite with phosphorus chloride, is an oil that solidifies at 0° and boils at 275°.
Phthalic acid behaves as having the first formula in some reactions and as having the second formula in others.
Phthalene chloride with phosphorus pentachloride gives two phthalene tetrachlorides, one melting at 88° and the other at 47°.
They are not interconvertible and the formulas C 6 H 4 (CC1 3) (COC1) and C6H4(CC12)20 are given.
Phthalimide is formed by heating C6H4(CO)2NH, phthalic anhydride or chloride in ammonia gas or by molecular rearrangement of ortho-cyanbenzoic acid.
Phthalic acid forms N-metallic and alkyl salts.
Bromine and potash give anthranilic acid, C6H4 (NH2) (CO2H). (See Indigo.)
Isoptahhalic acid is obtained by oxidizing meta-xylene with chromic acid or by fusing potassium meta-sulfobenzoate or meta-brombenzoate with potassium formate (terephthalic acid is also formed in the latter case).
Phthalic acid melts above 300°C and dissolves in 7800 parts of cold water and boiling at 460 degrees. Barium salt (+6H 2 0) is very soluble (difference between phthalic and terephthalic acids).
Uvitic acid, 5-methyl isophthalic acid, is obtained by oxidizing mesitylene or by condensing pyroracemic acid with baryta water.
A mixture of terephthalic acid, almost insoluble in water, alcohol and ether, and cumin and cumin, formed by oxidation of benzene's paradiderivatives, or best of all by oxidation of cumin oil; sublimes without melting when heated
Introduction: Phthalic acid is an aromatic dicarboxylic acid with the formula C6H4(CO2H)2.
It is an isomer of isophthalic acid and terephthalic acid.
Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commercial chemical produced on a large scale.
Phthalic acid preparation
Alkyl benzene compounds heated with strong oxidizing agents.
The phthalic acid alkyl group is oxidized to the carboxylic acid group.
When two alkyl groups are oxidized, two carboxylic acid groups are given.
Synonyms :
phthalic acid
88-99-3
1,2-benzenedicarboxylic acid
benzene-1,2-dicarboxylic acid
o-phthalic acid
patalic acid
o-dicarboxybenzene
o-benzenedicarboxylic acid
acid phthalic
phthalic acid
kiselina ftalova
ortho-phthalic acid
orthophthalic acid
UNII-6O7F7IX66E
MFCD00002467
Sunftal 20
CHEMBL1045
6O7F7IX66E
CHEBI:29069
Acide phtalique [French]
Kyselina ftalova [Czech]
CCRIS 1446
HSDB 1339
Benzene-1,2-dicarboxylic Acid (Phthalic Acid)
MGK 5348
EINECS 201-873-2
BRN 0608199
Alizarinate
naphthalenete
phthalinate
alizarinic acid
phthalic acid
pathalc acd
AI3-02409
naphthalenic acid
o-Carboxybenzoate
