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フタル酸ジアミル

Dipentyl phthalate

HCID 8561
ノート反応
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
部分構造検索類似構造を探す

基本情報

CAS
131-18-0
標準SMILES
CCCCCOC(=O)c1ccccc1C(=O)OCCCCC
InChIKey
IPKKHRVROFYTEK-UHFFFAOYSA-N
分子式
C18H26O4
平均分子量
306.4 g/mol
単同位体質量
306.18310931

概要

Di-n-pentyl phthalate is a clear colorless to light yellow liquid. Practically odorless. Floats on water. (NTP, 1992)

名称と識別子

優先名称
Dipentyl phthalate
IUPAC
dipentyl benzene-1,2-dicarboxylate
現地名
フタル酸ジアミル
英語名
DI-N-PENTYL PHTHALATE-D4
分子式
C18H26O4
分子量
306.4

名称と別名

Dipentyl phthalate131-18-0DIAMYL PHTHALATEDi-n-pentyl phthalateAmyl phthalateAmoildipentyl benzene-1,2-dicarboxylatedi-n-Amyl phthalateDi-n-pentylphthalatePhthalic acid, dipentyl esterdiamylphthalatePhthalic Acid Diamyl Ester
名称をさらに表示
フタル酸ジアミルフタル酸ジペンチルジアミルフタラートアモイルジアミル=フタラートフタル酸ジ-N-ペンチルフタル酸ジ-N-ペンチル標準品フタル酸ジnペンチルフタル酸ジフェニルフタル酸ジペンチル、ジペンタン-1-イル=フタラートフタル酸ジ‐N‐ペンチルフタル酸ジ‐N‐ペンチル標準品フタル酸ジペンチル標準品フタル酸ジ-n-ペンチル, 98%フタル酸ジアミル, 100 µg/mL in MeOH1,2-ジペンチル ベンゼン-1,2-ジカルボキシラートフタル酸ジベンチルDPPDAP/Dipentyl phthalateDI-N-PENTYL PHTHALATE-3,4,5,6-D4PHTHALIC ACID, BIS-N-PENTYL ESTER3-(4-(((tert-butoxycarbonyl)amino)methyl)phenyl)-2,2-dimethylpropanoic acid
DTXSID5031131Phthalic acid, diamyl esterDPNPDipentyl 1,2-benzenedicarboxylateAI3-00363 (USDA)1,2-dipentyl benzene-1,2-dicarboxylateCHEBI:346805DC92K224X

物性

構造計算による物性

XLogP
5.8
極性表面積
52.6 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
12
重原子数
22
形式電荷
0
複雑度
295

実験および物理化学的性質

PolymersPlastics & Rubber -> Phthalate Esters
SpringerMaterials PropertiesBoiling point
LogP · 2 件

log Kow = 5.62

4.85

OdorNearly odorless
Density · 2 件

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

1.022 at 20 °C

Color/FormColorless, oily liquid
Solubility · 4 件

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

Phthalate esters are soluble to various extents in many common organic solvents and oils, but have a relatively low solubility in water. /Phthalate esters/

Soluble in carbon tetrachloride, carbon disulfide

In water, 0.8 mg/L at 25 °C

Flash Point · 3 件

357 °F (NTP, 1992)

357 °F; 180 °C (Closed cup)

245 dec F (118 °C) (Closed cup)

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 2 件

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

H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Danger

H360 (99.3%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 4 件

Hazard Traits - Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Immunotoxicity; Reproductive Toxicity; Respiratory Toxicity

S - indicates a substance that is identified in a final Significant New Use Rule.

Substance: Dipentyl phthalate (DPP)

1,2-Benzenedicarboxylic acid, dipentyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

DOT LabelClass 9
Fire HazardsThis chemical is combustible. (NTP, 1992)
Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME; IT CAN REACT WITH OXIDIZING MATERIALS.
Health HazardsInhalation of vapors from very hot material may cause headache, drowsiness, and convulsions. Hot vapors may irritate eyes. (USCG, 1999)
Hazards SummaryLike dioctyl phthalate, it may cause CNS depression and mild liver toxicity after ingestion of large amounts; [HSDB] An irritant; [MSDSonline] See PHTHALATE ESTERS.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

Diamyl phthalate was metabolized in vivo to its corresponding monoester by nonspecific esterases in the intestinal mucosa and other tissues.

Phthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (A2884)

用途と製造

Uses · 3 件

Used as plasticizer; [Hawley]

Plasticizer

Phthalate esters are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are used in a variety of household applications such as shower curtains, vinyl upholstery, adhesives, floor tiles, food containers and wrappers, and cleaning materials. Personal care items containing phthalates include perfume, eye shadow, moisturizer, nail polish, liquid soap, and hair spray. (L1903)

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#997]
Methods of ManufacturingBy esterification of the phthalic anhydride with amyl alcohol in the presence of approximately 1% concentrated sulfuric acid as catalyst.
General Manufacturing Information1,2-Benzenedicarboxylic acid, 1,2-dipentyl ester: ACTIVE
応用分野 · 4 件

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

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

データベース識別子

CAS
131-18-0
PubChem CID
8561
DTXSID
DTXSID5031131
ChEMBL
CHEMBL1503330
ChEBI
CHEBI:34680
UNII
5DC92K224X
EC Number
205-017-9
Nikkaji
J46.841J

648 °F at 760 mmHg (NTP, 1992)

342 °C

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point · 2 件

less than -67 °F (NTP, 1992)

FP: less than -55 °C

物理化学的性質

融点
-55 °C · -55 °C
沸点
342 °C · 342 °C
比重(密度)
1.025 g/mL · 1.025 g/mL at 20 °C(lit.)
屈折率
20 · n20/D 1.490
闪点
110 °C · >110°C
貯蔵温度
room temp
溶解性
Chloroform (Slightly), Ethyl Acetate (Slightly)
外見
液体
色
無色透明~微黄色透明
臭い (Odor)
マイルドで心地よい。
水溶解度
混和しないか、水に混ざりにくい。
BRN
1987323 · 1987323
Henry's Law Constant
1.1 · 1.1×101 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途
環境
InChI
1S/C18H26O4/c1-3-5-9-13-21-17(19)15-11-7-8-12-16(15)18(20)22-14-10-6-4-2/h7-8,11-12H,3-6,9-10,13-14H2,1-2H3
InChIKey
IPKKHRVROFYTEK-UHFFFAOYSA-N
SMILES
CCCCCOC(=O)c1ccccc1C(=O)OCCCCC
CAS データベース
131 · 131-18-0(CAS DataBase Reference)
EPAの化学物質情報
Dipentyl phthalate (131-18-0)

化学的性質

化学的特性clear colorless viscous liquid

Special Reports · 3 件

Nat'l Research Council Canada; Phthalate Esters in the Aquatic Environment (1980) NRCC No. 17583

USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067

USEPA/ECAO; Atlas Document for: Phthalate Esters (1980)

Reactivity Profile · 1 件

DI-N-PENTYL PHTHALATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Can generate electrostatic charges.

Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water. Insoluble 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.

Hazard Classes and Categories · 4 件

Repr. 1B (99.3%)

Reproductive toxicity - category 1B

Reproductive toxicity - Category 1B

Repr. 1B

安全と保護具

Fire FightingFire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.
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.

Fire Fighting ProceduresWater or foam may cause frothing.
Cleanup Methods... DIAMYL PHTHALATE ... WAS REMOVED FROM AIR BY AN ELECTROFILTER, ... . REMOVAL EFFICIENCY IS 82-93%.
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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.

Preventive Measures · 1 件

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Personal Protective Equipment (PPE) · 1 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

毒性情報

Health Effects · 1 件

Phthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called 'phthalate syndrome’. (A2883)

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 27,000(SRC), determined from a log Kow values of 5.62(2), and a regression-derived equation(3), indicate that diamyl phthalate is expected to be immobile in soil(SRC). Volatilization of diamyl phthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Diamyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.0X10-4 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation studies using pure cultures indicate that diamyl phthalate may biodegrade under aerobic conditions yielding phthalic acid and amyl alcohol(6). Although biodegradation data on diamyl phthalate are limited, biodegradation studies on a series of phthalate esters have demonstrated that, in general, phthalate esters are readily biodegraded(7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 27,000(SRC), determined from a log Kow values of 5.62(2), and a regression-derived equation(3), indicate that diamyl phthalate is 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 8.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 420(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(7). Estimated hydrolysis half-lives of 3.4 years and 130 days at pHs 7 and 8, respectively, suggest that hydrolysis is not expected to be an important process(8). Biodegradation studies using pure cultures indicate that diamyl phthalate may biodegrade under aerobic conditions yielding phthalic acid and amyl alcohol(9). Although biodegradation data on diamyl phthalate are limited, biodegradation studies on a series of phthalate esters have demonstrated that, in general, phthalate esters are readily biodegraded(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diamyl phthalate, which has an estimated vapor pressure of 2.0X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diamyl phthalate 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 32 hours(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diamyl phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesOral (L1903) ; inhalation (L1903) ; dermal (L1903)
Toxicity Summary · 1 件

Phthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (A2883)

Signs and SymptomsPhthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (A2883)
Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=131-18-0][Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=131-18-0]

Effluent ConcentrationsDiamyl phthalate was not found in 4 domestic sewages; 6 domestic sewages with storm runoff and small industrial effluent; 2 domestic sewage with storm runoff and large industrial effluent with a detection limit of 0.3 ug/L(1).
Soil Adsorption/Mobility · 1 件

The Koc of diamyl phthalate is estimated as 27,000(SRC), using a log Kow of 5.62(1), and 5.66(2), respectively, and a regression-derived equation(2). According to a classification scheme(4), this Koc value suggests that diamyl phthalate is expected to be immobile in soil.

Human Toxicity Excerpts · 1 件

/ALTERNATIVE and IN VITRO TESTS/ /It was/ previously found that some phthalates have nongenomic effects, exerting inhibitory effects on the functional activities of nicotinic acetylcholine receptors (nAChRs) in bovine chromaffin cells. ... This study ... investigated the effects of eight phthalates on the calcium signaling of human nAChR by using human neuroblastoma SH-SY5Y cells. All eight phthalates, with different potency, have inhibitory roles on the calcium signaling coupled with human nAChR, but not muscarinic acetylcholine receptors (mAChRs). For inhibition of human nAChR, the strongest to weakest potencies were observed as di-n-pentyl phthalate (DPP) --> butyl benzyl phthalate (BBP) --> di-n-butyl phthalate (DBP) --> dicyclohexyl phthalate (DCHP) --> di-n-hexyl phthalate (DHP) --> di-(2-ethyl hexyl) phthalate (DEHP) --> di-n-propyl phthalate (DPrP) --> diethyl phthalate (DEP). The potencies of phthalates were associated with their structures such that the most effective ones had dialkyl group carbon numbers of C4 or C5, with shorter or longer numbers resulting in decreased potency. At as low as 0.1 uM, DPP, DBP, BBP, DCHP and DHP significantly inhibited the calcium signaling of human nAChR. The IC50 of phthalates on human nAChR, ranging from 0.32 to 7.96 uM, were 10-50 lower than those for bovine nAChR.

Artificial Pollution SourcesDiamyl phthalate's production and use as a plasticizer(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

AEROBIC: When diamyl phthalate was incubated with pure cultures of Pseudomonas acidovorans under aerobic conditions, the initial products from this reaction were phthalic acid and amyl alcohol(1). Although the biodegradation of diamyl phthalate has not been studied, biodegradation studies on a series of phthalate esters have demonstrated that in general phthalate esters are readily biodegraded(2).

安全データ

wgk
3
tsca
TSCA listed
rtecs
TI1930000
ridadr
UN 3082 9/PG 3
hs_code
29173490
risk_code
60-61-50
消防法
危険物第4類第三石油類(水溶性)
hazard_code
T,N
safety_code
53-45-61
hazard_class
9
packing_group
III
Hazard Classifications
Aquatic Acute 1Repr. 1B
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
131-18-0(Hazardous Substances Data)

用途環境試料中のフタル酸エステルの分析(HPLC)用標準品、GC-MS分析標準品。

説明Di-n-pentyl phthalate is a colorless oily liquid. Sp.Gr. 1.02. B.P. approximately 350℃. Insoluble in water.

使用Di-n-pentyl phthalate is a plasticizer for PVC membrane electrodes.

一般的な説明Clear colorless to light yellow liquid. Practically odorless. Floats on water.

調製方法

純化方法Wash the ester with aqueous Na2CO3, then distilled water. Dry it with CaCl2 and distil it in a vaccum. Store it in a vacuum desiccator over P2O5. [Beilstein 9 IV 3178.]

上流・下流製品情報

上流原料

スルファート/鉄,(3:2)1-ペンタノールフタル酸無水物

サプライヤー100 社

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補足説明

定義ChEBI: A phthalate ester that is the dipentyl ester of benzene-1,2-dicarboxylic acid.