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フタル酸

Phthalic Acid

HCID 1017
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
88-99-3
標準SMILES
O=C(O)c1ccccc1C(=O)O
InChIKey
XNGIFLGASWRNHJ-UHFFFAOYSA-N
分子式
C8H6O4
平均分子量
166.13 g/mol
単同位体質量
166.02660867

概要

Phthalic acid appears as white crystals or fine white powder. (NTP, 1992)

名称と識別子

優先名称
Phthalic Acid
IUPAC
phthalic acid
現地名
フタル酸
英語名
Phthalic acid
分子式
C8H6O4
分子量
166.13

名称と別名

phthalic acid88-99-31,2-benzenedicarboxylic acido-phthalic acidbenzene-1,2-dicarboxylic acido-dicarboxybenzeneo-benzenedicarboxylic acidAcide phtaliqueKyselina ftalovaortho-phthalic acidDTXSID80214846O7F7IX66E
名称をさらに表示
フタル酸ベンゼン-1,2-ジカルボン酸オルトフタル酸オルソフタル酸o-フタル酸ベンゼン-o-ジカルボン酸1,2-ベンゼンジカルボン酸オルソフタール酸フタル酸(O-フタル酸)o-ベンゼンジカルボン酸Phthalic acid,99%1,2-dicarboxybenzeneFluorescein EP Impurity BNSC 5348PhthalsureSunftal 20
hydron;phthalateNSC-5348DTXCID901484CHEBI:29069RefChem:6136201-873-2Pathalic acidPHTHALICACID

データベース識別子

CAS
88-99-3
PubChem CID
1017
DTXSID
DTXSID8021484
ChEMBL
CHEMBL1045
ChEBI
CHEBI:29069
UNII
6O7F7IX66E
EC Number
201-873-2
Nikkaji
J3.547E

物性

構造計算による物性

XLogP
0.7
極性表面積
74.6 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
2
重原子数
12
形式電荷
0
複雑度
177

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Organic Acids

Phthalate

DrugsPharmaceuticals -> Listed in ZINC15
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP · 4 件

log Kow = 0.73

0.73

0.73

0.87

Density · 6 件

1.593 at 68 °F (NTP, 1992) - Denser than water; will sink

1.593 g/cu cm at 15 °C

Density/specific gravity: 9.4864 kmol/cu m @ 20 °C

Relative density (water = 1): 1.6

1.593

2.18 @ 191°C

Color/Form · 2 件

Colorless crystals

Plates from water

Solubility · 5 件

less than 1 mg/mL at 68 °F (NTP, 1992)

Soluble in alcohol; sparingly soluble in ether

1 g dissolves in 160 ml water, 10 ml alc, 205 ml ether, 5.3 ml methanol; practically insol in chloroform

In water, 6,965 mg/L at 25 °C

7.01 mg/mL at 25 °C

Flash Point · 4 件

334 °F (NTP, 1992)

334 °F (168 °C) (Closed cup)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H360D ***: May damage the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.1% (3 of 284) of reports.

Danger

H315 (47.5%): Causes skin irritation [Warning Skin corrosion/irritation]

危険有害性情報

Regulatory Information · 4 件

Chemical: 1,2-Benzenedicarboxylic acid

Regulation (EC) No 1107/2009 (amended)

REACH registered substance: Phthalic acid (EC: 201-873-2)

Phthalic acid: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 2 件

This chemical is combustible. (NTP, 1992)

Combustible. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible when heated.
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes, and respiratory passages. In high concentrations, it can cause narcosis.
Hazards Summary · 1 件

A skin, eye, and respiratory tract irritant; [ICSC] Irritating to skin and mucous membranes; No data available on possible toxic effects after ingestion; [HSDB] A skin, eye, mucous membrane, and respiratory tract irritant; Inhalation of high concentrations can cause CNS depression; [CAMEO] Causes somnolence and ataxia in lethal-dose feeding studies of mice; [RTECS] No evidence of teratogenicity in animal studies; No human data; [REPROTOX] An irritant; [MSDSonline]

FDA Requirementso-Phthalic acid is an indirect food additive for use as a component of adhesives.

化学と産業

薬理情報

Mechanism of Action · 2 件

Although it is well established that high dose administration of di(2-ethylhexyl)phthalate and its monoester metabolite induces severe testicular atrophy in rats the mechanisms of this testicular injury Is not clear. The present experiment was undertaken to examine the effects of di(2-ethylhexyl) phthalate and mono(2-ethylhexyl)phthalate on mitochondrial functions of rat testis. Di(2-ethylhexyl)phthalate and di-n-octyl phthalate, a di(2-ethylhexyl) phthalate isomer which causes less severe testicular injury did not inhibit the state 3 oxygen consumption up to 0.65 umol/mL in vitro. On the other hand, mono(2-ethylhexyl)phthalate and mono-n-octyl phthalate a metabolite of di-n-octyl phthalate inhibited the state 3 oxygen-consumption down to a concentration of 0.065 amble/mL. Testicular mitochondrial respiratory functions of rats administered 2 g/kg di(2-ethylhexyl) phthalate were lower than those of control or di-n-octyl phthalate treated rats. These differences were verified by characteristics of pharmacokinetic parameters and testicular concentrations of mono(2-ethylhexyl)phthalate and mono-n-octyl phthalate. It nay be suggested that a possible mechanism of testicular atrophy induced by di(2-ethylhexyl) phthalate may be due to direct inhibition by mono(2-ethylhexyl)phthalate (and partially di(2-ethylhexyl)phthalate) of the respiratory functions of Sertoli cell mitochondria in rat testis.

... phthalic acid and nonylphenol stimulated PXR-mediated transcription at concentrations comparable to those at which they activate estrogen receptor-mediated transcription using a transient reporter gene expression assay in COS-7 cells.

Metabolism/Metabolites · 5 件

Yields 4,5-dihydroxyphthalic acid in Pseudomonas. /FROM TABLE/

Dose effects of di(2-ethylhexyl)phthalate distribution, excretion, and binding to macromolecules were studied in rodents. The urinary di(2-ethylhexyl)phthalate metabolite profile was similar for all doses, except that free phthalic acid was 6 times greater on days 3 and 10 at the highest compared to the lowest dose.

The metabolism of di-(5-hexenyl)phthalate and di-(9-decenyl)phthalate was investigated in rats. Male CD rats received two oral doses of 3 to 12 uM/kg radiolabeled or unlabeled di-(5-hexenyl)phthalate and di-(decenyl)phthalate in cottonseed oil 24 hr apart. One third of the radioactivity was found in the urine. The metabolites were identified as mono-5-hexenyl-phthalate. Mono-5-hexenyl-phthalate comprised 21% of the total urinary phthalates while 5-hexenyl-phthalate glucuronide amounted to 13.2% and free 5-hexenyl-phthalate to 7.8%. In contrast no metabolites of di-(9-decenyl)phthalate were excreted as glucuronide conjugates and only a trace of free phthalic acid was detected although 40 to 50% of the compound was recovered in the urine. The distribution of the metabolic phthalates indicated a different metabolic pathway for di-(9-decenyl)phthalate and di-(5-hexenyl)phthalate. /It was/ concluded that the chemically reactive epoxide metabolite of phthalate with unsaturated side chains may play a role in the acute toxicity of di-(5-hexenyl)phthalate and di-(9-decenyl)phthalate.

関連反応

112 件
反応記録を作成
HRID 6112 の反応式
HRID 6112反応物としてuspto-grants-1993_09
HRID 39440 の反応式
HRID 39440生成物としてuspto-grants-2013_09
HRID 45758 の反応式
HRID 45758反応物としてuspto-grants-2013_09
HRID 47308 の反応式
HRID 47308反応物としてuspto-grants-2004_03
HRID 47310 の反応式
HRID 47310反応物としてuspto-grants-2004_03
HRID 72071 の反応式
HRID 72071反応物としてuspto-grants-2014_09
HRID 90073 の反応式
HRID 90073反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 180588 の反応式
HRID 180588反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
1 / 14 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す

168 °C c.c.

334 °F

Boiling Point · 4 件

Decomposes (NTP, 1992)

Decomposes

Boiling point = 598.00 K (Based on predicted value for phthalic acid by Meissner's method with a suitable adjustment for isomerism based on similar compound relationships.)

decomposes

Decomposition · 2 件

When heated to decomposition it emits acrid smoke and irritating fumes.

191 °C

Melting Point · 5 件

410 to 412 °F (decomposes) (NTP, 1992)

Decomposes at 230 °C

Melting point: ca. 210 °C, converted into phthalic anhydride with the elimination of water.

Triple point temperature and pressure = 464.15 K (estimated to be equal to the melting point), 7.8183X10+3 Pa

Melting point = 464.15 K (determined in a sealed tube)

Vapor Density · 2 件

5.73 (AIR= 1)

Relative vapor density (air = 1): 5.7

物理化学的性質

融点
210 · 210-211 °C (dec.) (lit.)
沸点
214.32 °C · 214.32°C (rough estimate)
比重(密度)
1.59 g/cm3 · 1.59 g/cm3 at 15 °C
蒸気圧
7.8 hPa · 7.8 hPa (191 °C)
屈折率
1.51 · 1.5100 (estimate)
闪点
168 °C · 168 °C
貯蔵温度
30 °C · Store below +30°C.
溶解性
0.1 g/mL、透明 · メタノール: 0.1 g/mL、透明
酸解離定数(Pka)
2.89 · 2.89(at 25℃)
外見
粉
色
白い
PH
3.2 · 3.2(1 mM solution);2.55(10 mM solution);2(100 mM solution);
水溶解度
7 g/L · 7g/L(25℃)
比熱容量
1.13 J/ · Cp(crystal): 1.13 J/(g·K), at 25℃
Merck
14 · 14,7371
BRN
608199 · 608199
Henry's Law Constant
4.9 · 4.9×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant
5.1 · 5.1(Ambient)
安定性
安定。可燃性。強力な酸化剤とは相容れない。
InChI
1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
InChIKey
XNGIFLGASWRNHJ-UHFFFAOYSA-N
SMILES
OC(C1=C(C(O)=O)C=CC=C1)=O
LogP
0.73 at · 0.73 at 20℃
CAS データベース
88 · 88-99-3(CAS DataBase Reference)
NISTの化学物質情報
1 · 1,2-Benzenedicarboxylic acid(88-99-3)
EPAの化学物質情報
Phthalic acid (88-99-3)
化学的性質 · 3 件

化学的特性フタル酸は有機化合物の一種で化学式はC8H6O4または具体的にはC6H4COOH2で表されますこの物質は工業的には主にプラスチックの製造に使用される重要な化学品です特にフタル酸は柔軟なプラスチック製品を作るためのフタル酸エステルの製造に欠かせません

化学的特性PHTHALIC ACID,C6H4(COOH)2, mp 208 °C (ortho), 330 °C (meta and iso), the ortho form sublimes and the meta and iso forms decompose with heat, sp gr 1.593 (ortho). Phthalic acid is very slightly soluble in H2O, soluble in alcohol, and slightly soluble in ether. The solid form is colorless, crystalline

化学性质フタル酸は無色の結晶性固体ですが加熱すると融けやすく水にはあまり溶けませんが有機溶剤にはよく溶ける性質を持っていますまたこの物質は二塩基性酸として知られ弱酸ですが2つのカルボキシル基COOHが特徴的です

Reactive GroupAcids, Carboxylic
Reactivity ProfilePHTHALIC ACID is a carboxylic acid. This chemical is sensitive to exposure to extreme heat. This compound reacts violently with nitric acid. It is incompatible with sodium nitrite. It is also incompatible with oxidizers. (NTP, 1992).
Chemical DangersThe solution in water is a weak acid.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Air and Water ReactionsInsoluble in water.
NFPA Hazard Classification · 3 件

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

安全と保護具

Fire Fighting · 2 件

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest.

Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth.

First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Firefighting HazardsEvaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.
Fire Fighting ProceduresPowder, water spray, foam, carbon dioxide.
Cleanup MethodsSweep spilled substance into containers; if appropriate, moisten first to prevent dusting (extra personal protection: P1 filter respirator for inert particles).
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.

Preventive Measures · 3 件

Good local & general ventilation are required where phthalic acid is handled.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

NO open flames ... Prevent deposition of dust; closed system, dust explosion-proof electrical equipment and lighting ... PREVENT DISPERSION OF DUST ... Do not eat, drink, or smoke during work.

Eye PreventionWear safety spectacles.
Fire PreventionNO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

毒性情報

Toxicological InformationRanking: 546 (total points: 251.74)
Ecotoxicity Values · 5 件

LC50; Species: Bufo bufo japonicus (Toad); Conditions: freshwater; static; Concentration: 36000 ug/L for 24 hr at 25 °C, pH 5.0 /formulated product/

LC50; Species: Bufo bufo japonicus (Toad); Conditions: freshwater; static; Concentration: >40000 ug/L for 24 hr at 25 °C, pH 6.0 /formulated product/

LC50; Species: Bufo bufo japonicus (Toad); Conditions: freshwater; static; Concentration: >40000 ug/L for 24 hr at 25 °C, pH 7.0 /formulated product/

LC50; Species: Bufo bufo japonicus (Toad); Conditions: freshwater; static; Concentration: >40000 ug/L for 24 hr at 25 °C, pH 8.0 /formulated product/

For more Ecotoxicity Values (Complete) data for PHTHALIC ACID (10 total), please visit the HSDB record page.

Environmental Fate · 4 件

TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values of 2 to 31(2), indicate that phthalic acid is expected to have very high mobility in soil(SRC). Volatilization of phthalic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2X10-11 atm-cu derived from its vapor pressure, 6.36X10-7 mm Hg(3), and water solubility, 6965 mg/L(4). Phthalic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Phthalic acid rapidly degraded in Chalmers soil (1.96% organic carbon, pH 6.0); 100% decomposition was obtained after 53 days(5).

TERRESTRIAL FATE: 14C-Phthalic acid (0.6-600 ppm) was added to the upper 15 cm of Norfolk sandy loam soil in 21 cm high pots and planted with wheat/corn or soybeans/fescue in greenhouse studies(1). The average half-life of phthalic acid (assuming a linear decay) was 37 days for all plantings and application rates. A balance sheet indicated that an average of 5.7% of the originally applied 14C was recovered from soil and plants at the end of the experiment (80 days); most of the phthalic acid was lost through volatilization or decomposition(1). A study was conducted at a plant site where an industrial waste from a terphthalic acid manufacturing facility was injected into the subsurface (259-305 m)(2). While phthalic acid was present at an avg concn of 76 mg/L in the injected waste, phthalic acid was not present in 3 monitoring wells, 2-4 years post injection(2). When phthalic acid was applied at 448,144 kg/ha to field plots in Muskegon City, MI and tilled to 6 inches within 5 days, the 3 plot average in the 0-6 inch layer was 557 ug/kg after 5 days, 424 ug/kg after 122 days and 0 ug/kg after 241 days(3). No phthalic acid was detected in the 9-15 inch core at any of the sampling times(3). No phthalic acid was present in the soil prior to application(3).

AQUATIC FATE: Based on a classification scheme(1), experimental Koc values of 2 and 31(2), indicate that phthalic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 6.36X10-7 mm Hg(4), and water solubility, 6965 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Phthalic acid completely disappeared from Mississippi River water in 2.5 to 5 wk at concns of 12.5 and 50 mg/L, respectively(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phthalic acid, which has a vapor pressure of 6.36X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phthalic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 days(SRC), calculated from its rate constant of 1.24X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase phthalic acid may be removed from the air by wet or dry deposition(SRC). Due to its high water solubility and polar nature, phthalic acid is associated with water droplets(4) in the atmosphere and effectively scavenged by rain(5). Experiments suggest that diacids, which mostly exist as particles (aerosols) in the atmosphere, are removed more efficiently during wet precipitation than most water soluble compounds(5).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Plant ConcentrationsBefore the widespread use of phthalate esters, phthalic acid was detected, but not quantified, in raspberries and poppies and the concn in tobacco leaf was 0.02% dry wt(1).
Signs and Symptoms · 4 件

Cough. Sore throat.

Redness.

Redness.

Sore throat.

Acute Toxicity LinkChemical: PHTHALIC ACID
Effluent Concentrations · 2 件

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, phthalic acid was identified in discharges of the following industrial categories (positive occurrences, median concn in ppb): leather tanning (3; 8.8), nonferrous metals (5; 5.0), paint and ink (6; 69.8), printing and publishing (1; 126.2), organics and plastics (5; 269.5), textile mills (3; 46.1), plastics and synthetics (6; 78.3), auto and other laundries (3; 22.9), pesticides manufacture (2; 2986.4), explosives (18; 29.5), foundries (7; 11.8), aluminum (3; 7.4), electronics (6; 60.6), organic chemicals (19; 32.3), mechanical products (2; 11.3), publicly owned treatment works (4; 3.3)(1). The highest effluent concns, and the only ones >1 ppm were 5969 ppb and 4761 ppb in the pesticides manufacture and organics and plastics industries(1). Effluent samples from the Kimberly-Clark Terrace Bay Mill in 1981 contained 0.16 and 0.56 mg/L of phthalic acid(2). Phthalic acid was found in effluent from advanced wastewater treatment plants in Lake Tahoe CA, Orange County CA, Dallas TX, and Washington DC (Blue Plains plant)(3). Phthalic acid was found at concns of 566.9 ug/L of fuel burned from motor vehicle traffic in a Los Angeles roadway tunnel(4). Phthalic acid was found in automobile exhaust: 1982 Toyota Corolla 15 nmol/cu m; 1971 Mercedes Benz 214 nmol/cu m(5).

/detected/ in primary sewage plant effluent: 2 mg/L

Soil Adsorption/Mobility · 1 件

The Koc values were determined for an acidic forest soil (Podzol, 4.85% organic carbon, pH 2.8), an agricultural soil (Alfisol, 1.25% organic carbon, pH 6.7) and a sublimnic soil (sediment from Lake Constance, Germany, 1.58% organic carbon, pH 7.1) as 31, 2 and 2, respectively(1). According to a classification scheme(2), these Koc values suggest that phthalic acid is expected to have very high mobility in soil. Phthalic acid adsorbs strongly to aluminum and iron oxides via a surface ligand exchange reaction(3). Adsorptivity is sensitive to pH; for aluminum oxide the fraction absorbed is >0.8 below pH 6 and falls below 0.1 above pH 7.5(3).

Natural Pollution Sources · 1 件

Phthalic acid in soil may originate from lignin-type organic matter (phenols) which may be converted to aromatic diacids by microbial action(1). Phthalic acid has been found in Russian shale, bacteria, fungus, and Lily of the Valley oil (trace)(2).

Atmospheric Concentrations · 5 件

URBAN/SUBURBAN: The ambient annual average concn of phthalic acid in fine particle organic compounds at four sites on a west to east trajectory, West Los Angeles, downtown Los Angeles, Pasadena, and Rubidouc for 1982 were 60.6, 60.0, 55.7 and 53.5 ng/cu m, respectively(1). 24-Hr samples were collected at 6 day intervals over the year(1). Concns were lowest from Sept to January and highest in February(1). The concn of phthalic acid at a background site on San Nicolas Island, west of Los Angeles, averaged <0.03 ng/cu m from July to December(1). In a study of long-term transport of photochemical air pollution from coastal areas in Japan with large emission sources to inland mountains, the resulting mean concns of phthalic acid in airborne aerosols in a plume at Takasaki (July 26-31, 1986) and Karuizawa (July 29-31, 1986) were 22.1 and 19.5 ng/cu m, respectively(2). Phthalic acid was identified in airborne particulate matter from a suburban area 60 km northeast of Tokyo, Japan in April 1985(3). The concn range of phthalic acid in aerosol samples (n=21) collected from the spring of 1988 to the winter of 1989 in Tokyo, Japan was 4.9-30 ng/cu m(4).

URBAN/SUBURBAN: Monitoring of phthalic acid in Los Angeles, CA in 1984: West Los Angeles (n=8) 0.12-1.76 nmol/cu m; downtown (n=2) 1.38-1.95 nmol/cu m; greenhouse (n=2) 0.15-0.55 nmol/cu m(1). Atmospheric concns of phthalic acid were measured in the southeastern United States from April 1999 to January 2000; North Birmingham, Al 5.88 ng/cu m, Jefferson Street, Atlanta, GA 5.98 ng/cu m, Gulfport, MS 2.32 ng/cu m, Pensacola, FL 2.87 ng/cu m and OLF#8, FL 2.07 ng/cu m(3). Tokyo aerosol concns: Feb 1992 (n=2): 130 ng/cu m, 85 ng/cu m; July 1992: (n=2) 135 ng/cu m, 157 ng/cu m(2). Phthalic acid was the third most abundant diacid in Tokyo, Japan aerosols(2). A study of water-soluble organic compounds in urban atmospheric particles from Kobe City, Japan found that phthalic acid was detected in the 0.43-1.1 um size fraction with concentrations of <2.80 ng/cu m from Aug 3-14, 1998, 3.03 ng/cu m from Oct 7-19, 1998, 4.20 ng/cu m from Mar 1-26, 1999 and 3.64 ng/cu m from Apr 27- May 17, 1999(4).

URBAN/SUBURBAN: Wintertime atmospheric concentrations of phthalic acid were measured in Fresno, CA as 9.16 ng/cu m for the sampling period Dec 26-28, 1995 and 9.09 ng/cu m for the sampling period of Jan 4-6, 1996(1). Wintertime concentrations were also measured in Bakersfield, CA as 6.78 ng/cu m for the sampling period Dec 26-28, 1995 and 13.1 ng/cu m for the sampling period of Jan 4-6, 1996(9). Five urban sites were analyzed for phthalic acid in southern California in 1995; Long Beach 3.51 ng/cu m, Mira Loma 3.19 ng/cu m, Riverside 4.51 ng/cu m, San Dimas 4.54 ng/cu m and Upland 4.07 ng/cu m(2). Continental background aerosol levels of phthalic acid were measured in Tokyo, Japan, Vienna, Austria and Los Angeles, CA at 135 ng/cu m, 18 ng/cu m and 60 ng/cu m, respectively(3). Samples taken from four sites in the Los Angeles, CA area September 8-9, 1993 found an average of 80.2 ng/cu m of phthalic acid in atmospheric fine particulates(4).

Human Toxicity Excerpts · 5 件

/SIGNS AND SYMPTOMS/ There have been reports of conjunctivitis, bloody nasal excreta, atrophy of nasal mucosa, hoarseness, cough and bronchitis in workers employed on the production of phthalic acid and anhydride.

/SIGNS AND SYMPTOMS/ ACUTE ... SYMPTOMS: Inhalation--cough, sore throat. Skin--redness. Eyes--redness, pain.

/CASE REPORTS/ ... A factory worker has been in contact with raw tributyl tin phthalate on one leg. Soon after taking a hot-water bath, he developed severely painful erythema on this leg. Patch tests and chemical analysis revealed that hot water hydrolyzed tributyl tin phthalate and produced concentrated phthalic acid.

/EPIDEMIOLOGY STUDIES/ A large population based case control study evaluated occupational exposures in 1,098 Danish males diagnosed with multiple myeloma from 1970 to 1984 and in 4,169 age and gender matched controls alive at the time of case diagnosis. Associations with phthalates persisted, but were inconsistent with duration and probability of exposure. /Phthalates/

/OTHER TOXICITY INFORMATION/ The rapid proliferation of complex plastic polymers and resins has led to a marked incr of work induced asthma due to low molecular weight agents. Phthalates are frequently used in the manufacture of epoxy resins, plasticizers, adhesives and a wide variety of other materials. They have recently been identified as an important irritant and immunogen of at least four occupational respiratory syndromes, ie, asthma/rhinitis, late respiratory systemic syndrome,pulmonary disease-anemia syndrome, and an irritant reaction. /Phthalates/

法規制情報

FDA Requirementso-Phthalic acid is an indirect food additive for use as a component of adhesives.

安全データ

wgk
1
tsca
TSCA listed
rtecs
TH9625000
毒性
LD50 orally in rats: 7.9 g/kg (Shaffer)
hs_code
29173980
risk_code
36/37/38
化審法
(3)-1337
hazard_code
Xi
safety_code
26-36-37/39
Hazard Classifications
Eye Dam. 1
ストレージクラス
11 - Combustible Solids
有毒物質データの
88-99-3(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
人的[青]=0 火災[赤]=1

毒性と防護

毒性LD50 7.9 g/kg(ラット,経口).

Phthalate grown cells readily oxidized dibutylphthalate, phthalate, 3,4-dihydroxyphthalate and protocatechuate. Phthalate-3,4-dioxygenase (and possibly the dihydrodiol dehydrogenase) was induced by phthalate or a metabolite and subsequent enzymes were inducible by protocatechuate or a subsequent metabolic product. During growth at 37 °C, strain 12B gave clones at high frequency that had lost the ability to grow with phthalate esters.

For more Metabolism/Metabolites (Complete) data for PHTHALIC ACID (6 total), please visit the HSDB record page.

Absorption, Distribution and ExcretionProbably excreted as phthalic acid. /From table/
Tissue LocationsLiver

用途と製造

Uses · 3 件

Used as an analytical and laboratory reagent and to make medicines, dyes, phenolphthalein, phthalimide, anthranilic acid, and synthetic perfumes; [HSDB]

... Medicine ... Organic synthesis. Analytical reagent.

Dyes, phenolphthalein, phthalimide, anthranilic acid, synthetic perfumes, laboratory reagent.

U.S. Production · 4 件

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3110]

Methods of Manufacturing · 2 件

Vapor-phase oxidation of naphthalene, catalyzed by vanadium and molybdenum oxides, followed by hydrolysis

Manufactured by catalytic oxidation of o-toluic acid and oxidation of xylene: Taylor, Dean, US 3064046 (1962 to I.C.I.); Cier, US 3088974 (1963 to Esso Res. & Eng.). Isolation from the fungus, Gibbererella fujikuroi.

Formulations/Preparations · 2 件

Grade: Technical, reagent.

Typical assay (by titration) 99.5%/from sole US bulk producer/

Use Classification · 3 件

Transformation products

Environmental transformation -> Pesticide transformation products (metabolite, successor)

METABOLITES

General Manufacturing Information · 5 件

1,2-Benzenedicarboxylic acid: ACTIVE

o-Phthalic acid is seldom employed, since its anhydride is easier to use.

Phthalic anhydride is the principal commercial form of phthalic acid and it is presently manufactured by catalytic air oxidation of o-xylene or naphthalene.

Formed as a byproduct in the manufacture of phthalic anhydride.

Industrially unimportant.

応用分野 · 6 件

解説フタル酸,針状晶.融点191 ℃(封管中).密度1.593 g cm-3.pK1 2.95,pK2 5.41.大気中で加熱すると脱水されて無水フタル酸となって昇華する.エタノール,熱水に易溶,水,エーテルに難溶.フタル酸と高級アルコールのエステルは可塑剤として,ジエチルエステルは溶剤として多量に用いられる.また,ポリエステル樹脂,とくにアルキド樹脂の縮合成分として用いられる.フタル酸のカリウム塩は,加熱により転位してテレフタル酸となる.フタル酸は,青色のフタロシアニン色素の原料として用いられる.そのほか,染料,医薬品などの中間物として種々の用途がある.分析試薬としてジルコニウムの分離·定量にも用いられる.森北出版「化学辞典(第2版)

用途遊離酸型のフタル酸類は一般的に、昇華性を有する無色固体で水にも有機溶媒にも溶けにくく、極性の高い有機溶媒に溶けやすいといった性質を示す。 フタル酸類は合成樹脂のモノマーとして利用されたり、特にエステル体の一部は、熱可塑性樹脂の可塑剤として30%?70%w/wほど添加される。

用途ジルコニウムの沈殿剤、有機合成原料、フタル酸塩製造原料。。

説明Phthalic acid is an aromatic dicarboxylic acid, with 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 commodity chemical produced on a large scale.

使用It is a dibasic acid, with pKa's of 2.89 and 5.51. The mono potassium salt, potassium hydrogen phthalate is a standard acid in analytical chemistry. Typically phthalate esters are prepared from the widely available phthalic anhydride. Reduction of phthalic acid with sodium amalgam in the presence of water gives the 1,3- cyclohexadiene derivative.

一般的な説明White crystals or fine white powder.

調製方法 · 2 件

Phthalic acid is produced by the catalytic oxidation of naphthalene directly to phthalic anhydride and a subsequent hydrolysis of the anhydride. Phthalic acid was first obtained by French chemist Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic acid". After the Swiss chemist Jean Charles Galissard de Marignac determined its correct formula, Laurent gave it its present name. Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst.

純化方法Crystallise phthalic acid from water. [Beilstein 9 IV 3167.]

上流・下流製品情報

上流原料

アンモニア水フタル酸無水物硝酸

下流製品

フタロニトリルcomplex polystyrene high efficiency anticorrosion paintオキセンドロンマーキュロクロム(S)-2-メチル-3-アリル-4-オキソ-2-シクロペンテン-1-オールホスメットフタル酸ジ-n-オクチル安息香酸フタル酸ビス(2-エチルヘキシル)cis-1,2-シクロヘキサンジアミンテトラメトリンフタル酸ジメチル4-アミノピリジン2-ブロモ安息香酸メチルフタル酸ジアリルフタル酸ジアミル2',7'-ジクロロフルオレセインC.I. Sulphur Brown 2 (8CI)
補足説明 · 1 件

定義phthalic acid: colourlesscrystalline dicarboxylic acid,C6H4(COOH)2; r.d. 1.6; m.p. 207°C.The two –COOH groups are substitutedon adjacent carbon atoms ofthe ring, the technical name beingbenzene-1,2-dicarboxylic acid. Theacid is made from phthalic anhydride(benzene-1,2-dicarboxylic anhydride,C8H4O3), which is made by the catalyticoxidation of naphthalene. Theanhydride is used in making plasticizersand polyester resins.

INDOOR AIR: Phthalic acid was identified in particulate matter in air in Chinese homes burning smokeless coal(1).

RURAL/REMOTE: Atmospheric concentrations of phthalic acid were measured in the southeastern United States from April 1999 to January 2000; Centreville, AL 5.94 ng/cu m, Yorkville, GA 3.59 ng/cu m and Oak Grove, MS 2.54 ng/cu m(1). Wintertime atmospheric concentrations of phthalic acid were measured in Kern Wildlife Refuge, CA as 4.71 ng/cu m for the sampling period Dec 26-28, 1995 and 5.43 ng/cu m for the sampling period of Jan 4-6, 1996(2). Four rural sites were analyzed for phthalic acid in southern California in 1995; Atascadere 4.13 ng/cu m, Lake Elsinore 3.01 ng/cu m, Lompoc 1.39 ng/cu m and Santa Maria 1.97 ng/cu m(3). Two mountain sites and one desert site were also analyzed; Alpine 4.6 ng/cu m, Lake Arrowhead 8.17 ng/cu m and Lancaster 2.99 ng/cu m(3). Continental background aerosol levels of phthalic acid were measured in South Africa, Salzburg, Austria and Antarctica at 3.3 ng/cu m, 3.3 ng/cu m and 1.7 ng/cu m, respectively(4). Concentrations of phthalic acid were measured in arctic aerosols from July of 1987 to June of 1988 ranging from <0.005 ng/cu m to 5.8 ng/cu m(5).