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디옥틸 프탈레이트

di-N-Octyl Phthalate

HCID 8346
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
117-84-0
표준 SMILES
CCCCCCCCOC(=O)c1ccccc1C(=O)OCCCCCCCC
InChIKey
MQIUGAXCHLFZKX-UHFFFAOYSA-N
분자식
C24H38O4
평균 분자량
390.6 g/mol
단동위원소 질량
390.27700969

개요

Di-n-octylphthalate is a colorless, odorless, oily liquid that doesn't evaporate easily. It is a man-made substance used to keep plastics soft or more flexible. This type of plastic can be used for medical tubing and blood storage bags, wire and cables, carpetback coating, floor tile, and adhesives. It is also used in cosmetics and pesticides.

이름 및 식별자

우선 이름
di-N-Octyl Phthalate
IUPAC
dioctyl benzene-1,2-dicarboxylate
현지명
디옥틸 프탈레이트
영어명
Dioctyl phthalate
분자식
C24H38O4
분자량
390.56

이름 및 동의어

Dioctyl phthalateDI-N-OCTYL PHTHALATE117-84-0Dinopol NOPDNOPVinicizer 85n-Octyl phthalateCelluflex DOPPhthalic acid, dioctyl esterBis(n-octyl) phthalateDioctyl 1,2-benzenedicarboxylatePx-138
이름 더 보기
디옥틸프탈레이트다이옥틸프탈레이트디옥틸프탈레이트다이-N-옥틸 프탈레이트1,2-벤젠디카르복시산, 디옥틸 에스터N-옥틸 프탈레이트o-벤젠디카르복시산, 디옥틸 에스터다이옥틸 프탈레이트디-N-옥틸 프탈레이트디노폴디옥틸 o-프탈레이트비니시저 85옥틸 프탈산프탈산, 디옥틸 에스터디-n-옥틸프탈레이트DOPOctyl phthalateDICAPRYL PHTHALATEdi-n-octyldi-1-octylphthalateDI OCTYLE PHTHALATE
Dioctyl o-benzenedicarboxylate1,2-Benzenedicarboxylic acid, dioctyl esterN-Dioctyl phthalateDioktylester kyseliny ftaloveDTXSID1021956o-Benzenedicarboxylic acid, dioctyl ester1,2-Benzenedicarbonic acid, dioctyl esterAI3-15071 (USDA)

물성

구조 계산 물성

XLogP
9.1
극성 표면적
52.6 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
18
무거운 원자 수
28
형식 전하
0
복잡도
369

실험 및 물리화학적 성질

Chemical Classes · 2건

Phthalate

Semi-Volatile Organic Compound (SVOC)

PolymersPlastics & Rubber -> Phthalate Esters
LogP · 2건

log Kow = 8.10

5.22

Density · 4건

0.98 at 77 °F (USCG, 1999) - Less dense than water; will float

Specific gravity: 0.978 at 20 °C

0.98

.978 @ 20°C

Viscosity39 mPa.s at 20 °C
Color/Form · 2건

Clear, oily liquid

Liquid at room temperature

Solubility · 2건

less than 1 mg/mL at 66 °F (NTP, 1992)

In water, 0.022 mg/L at 25 °C

Flash Point · 3건

219 °F (NTP, 1992)

420 °F (215 °C) (Open cup)

219 °F

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 3건

428 °F at 760 mmHg (NTP, 1992)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 57.1% (36 of 63) of all reports.

Warning

H361 (41.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

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

Aggregated GHS information provided per 63 reports by companies from 7 notifications to the ECHA C&L Inventory.

Not Classified

유해성 정보

Regulatory Information · 6건

Chemical: 1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester

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

Regulation (EC) No 178/2002 (amended)

1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Restricted substance: Di-n-octyl phthalate (DNOP)

1,2-Benzenedicarboxylic acid, dioctyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Phthalate esters: Environment tier II assessment
DOT LabelClass 9
Fire HazardsSpecial Hazards of Combustion Products: None (USCG, 1999)
Fire PotentialCombustible.
Health HazardsProduces no ill effects at normal temperatures but may give off irritating vapor at high temperature. (USCG, 1999)

화학 및 산업

약리 정보

Biological Half-LifeThe biological half-life in the blood was 3.3 hr in rats following administration of 2000 mg/kg n-dioctyl phthalate by gavage.
Metabolism/Metabolites · 6건

... Di-n-octyl phthalate (DnOP) is metabolized to its hydrolytic monoester, mono-n-octyl phthalate (MnOP), and other oxidative products. The urinary levels of one of these oxidative metabolites, mono-(3-carboxypropyl) phthalate (MCPP), were about 560-fold higher than MnOP in Sprague-Dawley rats dosed with DnOP by gavage. Furthermore, MCPP was also found in the urine of rats dosed with di-isooctyl phthalate (DiOP), di-isononyl phthalate (DiNP), di-isodecyl phthalate (DiDP), di-(2-ethylhexyl) phthalate, and di-n-butyl phthalate (DBP), although at concentrations considerably lower than in rats given similar concentrations of DnOP. The comparatively much higher urinary concentrations of MCPP than of the hydrolytic monoesters of the high-molecular-weight phthalates DiOP, DiNP, and DiDP in the exposed rats suggest that these monoesters may be poor biomarkers of exposure to their precursor phthalates and may explain the relatively low frequency of detection of these monoester metabolites in human populations. MCPP and MnOP were also measured in 267 human urine samples. The frequent detection and higher urinary concentrations of MCPP than MnOP suggest that exposure to DnOP might be higher than previously thought based on the measurements of MnOP alone. However, because MCPP is also a minor metabolite of DBP and other phthalates in rats, and the metabolism of phthalates in rodents and humans may differ, additional data on the absorption, distribution, metabolism, and elimination of MCPP are needed to completely understand the extent of human exposure to DnOP from the urinary concentrations of MCPP.

The metabolism of di-n-octyl phthalate (DnOP) results in the hydrolysis of one ester linkage to produce mono-n-octyl phthalate (MnOP), which subsequently metabolizes to form oxidative metabolites. ... The toxicokinetics of DnOP in adult female Sprague-Dawley rats /was investigated/ by monitoring the excretion of DnOP metabolites in urine after oral administration of DnOP (300 mg/kg). By using authentic standards, the presence of urinary phthalic acid (PA), MnOP, and the major DnOP metabolite, mono-(3-carboxypropyl) phthalate (MCPP) was clearly established. Furthermore, ... five additional urinary DnOP oxidative metabolites /were identified/ based on their chromatographic behavior and mass spectrometric fragmentation pattern. These DnOP oxidative metabolites, are postulated to be mono-carboxymethyl phthalate (MCMP), mono-(5-carboxy-n-pentyl) phthalate (MCPeP), mono-(7-carboxy-n-heptyl) phthalate (MCHpP), and isomers of mono-hydroxy-n-octyl phthalate (MHOP) (e.g., mono-(7-hydroxy-n-octyl) phthalate) and of mono-oxo-n-octyl phthalate (MOOP) (e.g., mono-(7-oxo-n-octyl) phthalate). The urinary excretion of DnOP metabolites followed a biphasic excretion pattern. The metabolite levels decreased significantly after the first day of DnOP administration although MCPP, MCHpP, MHOP, and MOOP were detectable after 4 days. We also studied the in vitro metabolism of DnOP and MnOP by rat liver microsomes. DnOP produced MnOP, MHOP, and PA in vitro whereas, MnOP produced MHOP and PA in vitro at detectable levels.

관련 반응

8건
반응 기록 만들기
HRID 884314 반응식
HRID 884314반응물로uspto-grants-2012_08
HRID 884315 반응식
HRID 884315반응물로uspto-grants-2012_08
HRID 884316 반응식
HRID 884316반응물로uspto-grants-2012_08
HRID 884317 반응식
HRID 884317반응물로uspto-grants-2012_08
HRID 884318 반응식
HRID 884318반응물로uspto-grants-2012_08
HRID 1486432 반응식
HRID 1486432용매로uspto-grants-2016_08
HRID 2232208 반응식
HRID 2232208생성물로uspto-grants-1988_11
HRID 2260793 반응식
HRID 2260793용매로uspto-grants-1995_12

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데이터베이스 식별자

CAS
117-84-0、8031-29-6
PubChem CID
8346
DTXSID
DTXSID1021956
ChEMBL
CHEMBL1409747
ChEBI
CHEBI:34679
UNII
8X3RJ0527W
EC Number
204-214-7、617-053-6
Nikkaji
J2.474K

BP: 220 °C at 2 mm Hg

428 °F

DecompositionWhen heated to decomp it emits acrid smoke and irritating fumes.
Melting Point · 4건

-13 °F (NTP, 1992)

25 °C

-13 °F

25 °C

물리화학적 성질

녹는점
-25 ℃ · -25℃
끓는 점
380 °C · 380 °C
밀도
0.98 g/mL · 0.980 g/mL at 20 °C(lit.)
증기압
5 · 5(x 10-8 mmHg) at 82 °C, 500 at 132 °C (Gross and Colony, 1973)
굴절률
20 · n20/D 1.485
인화점
219 °C · 219 °C
저장 조건
2 · 2-8°C
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
기름진 액체
색상
무색
Specific Gravity
0.98 · 0.98
수용성
물에 불용성.
Merck
14 · 14,2864
BRN
1915994 · 1915994
Henry's Law Constant
1.41 · 1.41(x 10-12 atmm3/mol) at 25 °C (approximate - calculated from water solubility and vapor pressure)
Dielectric constant
5.1 · 5.1(24℃)
주요 응용
청소용품화장품음식 및 음료개인 위생 관리
InChI
1S/C24H38O4/c1-3-5-7-9-11-15-19-27-23(25)21-17-13-14-18-22(21)24(26)28-20-16-12-10-8-6-4-2/h13-14,17-18H,3-12,15-16,19-20H2,1-2H3
InChIKey
MQIUGAXCHLFZKX-UHFFFAOYSA-N
SMILES
CCCCCCCCOC(=O)c1ccccc1C(=O)OCCCCCCCC
NIST
Di-n-octyl phthalate(117-84-0)
EPA
Di-n-octyl phthalate (117-84-0)

화학적 성질

Colorless liquid

Hazards Summary · 2건

Di-n-octylphthalate is a colorless, odorless, oily liquid that doesn't evaporate easily. It is a man-made substance used to keep plastics soft or more flexible. This type of plastic can be used for medical tubing and blood storage bags, wire and cables, carpetback coating, floor tile, and adhesives. It is also used in cosmetics and pesticides.

There is confusion in the naming of the dioctyl phthalate (DOP) esters: Di-n-octyl phthalate, Di-sec-octyl phthalate, and Diisooctyl phthalate. [CHEMINFO] A mucous membrane irritant; Like dioctyl phthalate, it may cause CNS depression and mild liver toxicity after ingestion of large amounts; [HSDB] Causes some liver injury in high-dose feeding studies of rats, but no evidence of significant reproductive effects; [ATSDR ToxProfiles] An irritant; [MSDSonline] See PHTHALATE ESTERS.

FDA RequirementsDioctylphthalate is an indirect food additive for use only as a component of adhesives.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special Reports · 5건

NTP/CERHR; Monograph on the Potential Human Reproductive and Developmental Effects of Di-n-Octyl Phthalate (DnHP), NIH Publication No. 03-4488 (May 2003). DnOP is one of 7 phthalate chemicals evaluated by the NTP CERHR Phthalates Expert Panel. These phthalates were selected for evaluation because of high production volume, extent of human exposures, use in children's products, and/or published evidence of reproductive or developmental toxicity. NTP-CERHR monographs are transmitted to federal and state agencies, interested parties, and the public and are available in electronic PDF format on the CERHR web site and in printed text or CD-ROM from the CERHR.[Available from, as of March 17, 2015: http://ntp.niehs.nih.gov/ntp/ohat/phthalates/dnop/dnop_monograph_final.pdf]

HHS/ATSDR; Toxicological Profile for Di-n-Octylphthalate PB/98/101033/AS (September 1997). The ATSDR toxicological profile succinctly characterizes the toxicologic and adverse health effects information for the hazardous substance described here. Each peer-reviewed profile identifies and reviews the key literature that describes a hazardous substance's toxicologic properties. Other pertinent literature is also presented, but is described in less detail than the key studies.[Available from, as of March 17, 2015: http://www.atsdr.cdc.gov/toxprofiles/index.asp]

Nat'l Research Council Canada; Effects of Phthalate Esters in the Canadian Environ (1976) NRCC No.17583

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

For more Special Reports (Complete) data for DI-N-OCTYL PHTHALATE (8 total), please visit the HSDB record page.

RCRA Requirements · 1건

U107; As stipulated in 40 CFR 261.33, when 1,2-benzenedicarboxylic acid, dioctyl ester, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenedicarboxylic acid, dioctyl ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.

안전 및 보호

Fire FightingExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
First Aid · 1건

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 HazardsCarbon oxides
Fire Fighting Procedures · 3건

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Water or foam may cause frothing.

Wear self contained breathing apparatus for fire fighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Cleanup Methods · 3건

Environmental precautions: Do not let product enter drains.

/ACCIDENTAL RELEASE MEASURES/ Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.

Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Disposal Methods · 4건

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U107, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

The following wastewater treatment technologies have been investigated for di-n-octyl phthalate: Biological treatment, solvent extraction.

A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.

Preventive Measures · 4건

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Normal measures for preventive fire protection.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of work day.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Threshold Limit Values (TLV)8 hr Time Weighted Avg (TWA): 5 mg/cu m.
Protective Action Criteria (PAC) · 3건

5.0 [mg/m3]

1600 [mg/m3]

9300 [mg/m3]

독성 정보

Toxicological Information · 2건

ATSDR Toxicological Profile for Di-n-octylphthalate (DNOP) - Succinctly characterizes the toxicologic and adverse health effects information.

Ranking: 153 (total points: 1006.96)

Body Burden · 1건

Di-n-octyl phthalate was detected in human adipose tissue collected throughout the US during the 1982 National Human Adipose Tissue Survey(1). Di-n-octyl phthalate was found in the serum of 1 of 41 young (17-47 months) Puerto Rican girls with premature breast development at a concentration of 438 ug/L(2). The degradation product di-n-octyl phthalate, mono-n-octyl phthalate was detected in the serum of 12 of 501 female and 15 of 502 male seniors from Uppsala, Sweden at a maximum of 5.55 and 10.7 mg/mL, respectively(3).

Interactions · 3건

Male rats, initiated with a single intraperitoneal dose of the carcinogen diethylnitrosamine and then partially hepatectomized, did not experience any liver weight gain after 10 weeks of dietary exposure to 500 mg/kg/day of di-n-octylphthalate ... When exposure was extended to 26 weeks, small increases in absolute liver weight that were not significant (p < 0.05) were observed at di-n-octylphthalate doses of 250 mg/kg/day (2% increase) and 500 mg/kg/day (8% increase). However, when combined with diminished body weight gains, relative liver weight gains were increased by 5-16% when compared with control values.

Male Sprague-Dawley rats were subjected to two-thirds partial hepatectomy which was followed 18 hr later by an intraperitoneal injection of diethylnitrosamine (DEN) at a dose of 30 mg/kg. Di(2-ethylhexyl)phthalate (DEHP) was added to the diet at 0.5%. Mono(2-ethylhexyl)phthalate (MEHP) and 2-ethylhexanol (2-EH) were added at equimolar levels with di(2-ethylhexyl)phthalate. Di-n-octyl-phthalate (DOP) was added to 1%. The development of gamma-glutamyl-transpeptidase positive (GGT+) foci was strongly induced by di-n-octyl-phthalate in the livers of rats that had received a subcarcinogenic dose of diethylnitrosamine. None of the other compounds showed any tumor promoting activity. The development of gamma-glutamyl-transpeptidase positive preneoplastic foci in livers of rats was neither enhanced nor suppressed when rats were fed a dose equimolar to 0.5% di(2-ethylhexyl)phthalate. An elevated carnitine acetyltransferase (CAT) level was found following treatment with mono(2-ethylhexyl)phthalate or di(2-ethylhexyl)phthalate. Mono(2-ethylhexyl)phthalate significantly decreased liver gamma-glutamyl-transpeptiase activity. In addition mono(2-ethylhexyl) phthalate lowered the mean number of foci/square centimeter below that of the 2-ethylhexanol treated group. /It was found/ that di-n-octyl-phthalate can act as a tumor promoter, and this activity seems to be unrelated to liver peroxisome proliferation (as measure by carnitine acetyltransferase).

An in vivo assay using Salmonella typhimurium TA 98 showed that di-n-octylphthalate enhanced the mutagenicity of two tryptophan pyrolysis products, which is suggestive of increased mutagenic activity in high-temperature cooking if di-n-octylphthalate is present ... .

Target OrgansHepatic (Liver)
Health Effects · 1건

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)

Ecotoxicity Values · 5건

LC50; Species: Micropterus salmoides (Large mouth bass); Concentration: 32,900 ug/L for 7-8 days /Conditions of bioassay not specified/ /From table/

LC50; Species: Ictalurus punctatus (Channel catfish); Concentration: 690 ug/L for 7 days /Conditions of bioassay not specified/ /From table/

LC50; Species: Phasianus colchicus (ring-necked pheasant) age 10 days; oral >5000 ppm for 5 days

LC50; Species: Eisenia fetida (earthworm) adult, weight 300-500 mg; dermal 3140 (2270-4330) ug/sq cm for 48 hr

LC50; Species: Americamysis bahia (Opossum shrimp); Conditions: saltwater, flow through, 24.8 °C, pH 7.9-8.1, salinity 20-22 ppt, dissolved oxygen 6.6-7.0 mg/L; Concentration: 125000 ug/L for 28 days /98% purity/

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), log Koc values of 4.38-6.3(2-3), indicate that di-n-octyl phthalate is expected to be immobile in soil(SRC). Volatilization of di-n-octyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 1.0X10-7 mm Hg(3), and water solubility, 0.022 mg/L(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Di-n-octyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Di-n-octyl phthalate, present at 100 mg/L, reached 67% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(5). In a model terrestrial-aquatic ecosystem, di-n-octyl phthalate was rapidly degraded by organisms in the system, having a half-life of 5 days(6). Respirometric measurements of soil amended with di-n-octyl phthalate shows that when acclimated, there is some microbial utilization, although this is marginal at 4 and 10 °C(7).

AQUATIC FATE: Based on a classification scheme(1), log Koc values of 4.38-6.3(2-3), indicate that di-n-octyl phthalate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 2.6X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 1.0X10-7 mm Hg(3), and water solubility, 0.022 mg/L(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 31 and 230 days, respectively(SRC). Hydrolysis half-lives of 7.7 years and 280 days at pH values of 7 and 8, respectively, were estimated(6). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). Volatilization of di-n-octyl phthalate from model waste stabilization ponds was not observed(7). According to a classification scheme(8), BCFs of 1.16-9400 in mosquito fish(9), suggest the potential for bioconcentration in aquatic organisms is low to very high(SRC), this range may indicate the ability of aquatic organisms to readily metabolize this class of compounds(3). Di-n-octyl phthalate was biodegraded 85% after 10 days incubation in Rhine river water at 20 °C; at 4 °C, biodegradation was negligible(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), di-n-octyl phthalate, which has a vapor pressure of 1.0X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase di-n-octyl 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 19 hours(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase di-n-octyl phthalate may be removed from the air by wet and dry deposition(SRC). Di-n-octyl phthalate has a strong UV absorption band at 274.5 nm which extends beyond 290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1건

Di-n-octyl phthalate was detected in one sample of 80 proof vodka at a concentration of 131 ppb and one sample of 100 proof vodka at 57 ppb(1). It was also detected in two samples of flavored 80 proof vodka at 75 and 123 ppb(1). Di-n-octyl phthalate was not detected (detection limit 20 ng/g dry weight) in food samples collected over four days from a university restaurant, Paris, France; food samples tested were fish terrine, mixed salad, corn salad, radishes, lasagne, roast beef, chicken leg, mixed steak, basmati rice, fried vegetables, fried potatoes, plain yogurt, Gruyere cheese, Camembert cheese, granny apple, black grapes, stewed apples and fruit salad(2).

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)
Milk ConcentrationsDi-n-octyl phthalate was detected, not quantified in one sample of dried milk(1). The contamination was believed to be a result of contact with plastic(1).
Toxicity Summary · 2건

IDENTIFICATION AND USE: Di-n-octylphthalate (DNOP) is a clear, oily liquid. It is used as a plasticizer; DNOP can represent 5-60% of the total weight of the plastics and resins. It is found in cosmetics and colorants. DNOP also serves as a carrier for catalysts or initiators and as a substitute for electrical capacitor fluid. HUMAN EXPOSURE AND TOXICITY: In 173 subjects with suspected dermatoses to plastic or glue allergens, two subjects (1.2% of the group) experienced irritation after patch testing with 2.0% DNOP. None of the patients had allergic reactions. There is a case study of a worker with continuous exposure to DNOP during the manufacture of imitation leather, who developed an asthmatic reaction to the substance. Women with endometriosis showed significantly higher concentrations of DNOP in their blood in a study of 49 infertile women with endometriosis (study group), and 38 age-matched women without endometriosis (control group I) but with infertility related to tubal defects, fibroids, polycystic ovaries, idiopathic infertility and pelvic inflammatory diseases diagnosed by laparoscopy and a further group of 21 age-matched women (control group II). An increase in toxic polyneuritis has been reported in workers exposed primarily to dibutyl phthalates. Lesser levels of exposure to dioctyl, diisooctyl, benzylbutyl phthalates, and tricresyl phosphate were also noted. ANIMAL STUDIES: DNOP was reported to be a slight skin irritant when applied to the depilated skin of guinea pigs. However, DNOP was not a skin sensitizer in guinea pigs. Ocular administration of DNOP resulted in slight conjunctival irritation and no corneal damage. The results of several acute- and intermediate-duration oral studies in rodents indicate that the potential of DNOP to cause adverse reproductive and developmental effects is low. Unlike other phthalate esters such as DEHP, DNOP does not appear to affect testicular function or morphology. Observed hepatic effects in intermediate duration studies consisted of a statistically significant increase in hepatic ethoxyresorufin-0-deethylase activity and histological changes in hepatic architecture. Thyroid toxicity was also noted at this concentration. Rats treated with 100, 300, or 600 mg/kg DNOP by ip injection for up to 90 day were evaluated for immunological responses. The high dose resulted in early loss of distinction between the cortex and medulla of the thyroid, reduced numbers of follicles in the lymph nodes, and loss of morphology in the adrenal glands. However, there was no effect on immune response. Results of studies in Salmonella typhimurium strains TA98, TA100, TA1535, and TA1537 (with and without S-9 metabolic activation systems) indicated that DNOP is not mutagenic. ECOTOXICITY STUDIES: The toxicity of DNOP was assessed by measuring the effect of exposure to these compounds on the fecundity of Daphnia magna and on the hatching and survival of the early life stages of the fathead minnow Pimephales promelas. For Daphnia magna, exposure to 1.0 mg/L DNOP caused a significant reduction in reproduction. Exposure to DNOP did not affect survival of either early embryos or larvae of the fathead minnow at doses up to 10 mg/L (the highest dose tested). Hatching of the embryos was significantly decreased at 10 mg/L, but not at 3.2 mg/L DNOP.

규제 정보

FDA RequirementsDioctylphthalate is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 1건

U107; As stipulated in 40 CFR 261.33, when 1,2-benzenedicarboxylic acid, dioctyl ester, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenedicarboxylic acid, dioctyl ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

State Drinking Water Guidelines(FL) FLORIDA 140 ug/L

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
TI1925000
ridadr
2810
독성
Acute oral LD50 for mice 6,513 mg/kg (quoted, RTECS, 1985):rats 13,000 mg/kg (Dogra et al., 1989):mice 1,250-1,954 mg/kg (Etnier, 1987).
HS 번호
29173200
risk_code
60-61
safety_code
23-24/25
기존화학 물질
KE-02283
Hazard Classifications
Aquatic Chronic 4
스토리지 클래스
10 - Combustible liquids
유해 물질 데이터
117-84-0(Hazardous Substances Data)

Hepatic prepn from rat, baboon & ferret hydrolyzed the phthalate diester of di-n-octyl to corresponding monoester derivatives. /in addition,/ intestinal prepn from the 3 animal species & from man also catalyzed the monohydrolysis of phthalate diesters.

n-Octanol is a metabolite of DnOP. Octanol is oxidized to the fatty acid and metabolized by the fatty acid oxidation pathway.

For more Metabolism/Metabolites (Complete) data for DI-N-OCTYL PHTHALATE (6 total), please visit the HSDB record page.

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)

Absorption, Distribution and Excretion · 4건

Di-n-octyl phthalate (DnOP) is found as a component of mixed C6-C10 linear-chain phthalates used as plasticizers in various polyvinyl chloride applications, including flooring and carpet tiles. Following exposure and absorption, DnOP is metabolized to its hydrolytic monoester, mono-n-octyl phthalate (MnOP), and other oxidative products. The urinary levels of one of these oxidative metabolites, mono-(3-carboxypropyl) phthalate (MCPP), were about 560-fold higher than MnOP in Sprague-Dawley rats dosed with DnOP by gavage. Furthermore, MCPP was also found in the urine of rats dosed with di-isooctyl phthalate (DiOP), di-isononyl phthalate (DiNP), di-isodecyl phthalate (DiDP), di-(2-ethylhexyl) phthalate, and di-n-butyl phthalate (DBP), although at concentrations considerably lower than in rats given similar concentrations of DnOP. The comparatively much higher urinary concentrations of MCPP than of the hydrolytic monoesters of the high-molecular-weight phthalates DiOP, DiNP, and DiDP in the exposed rats suggest that these monoesters may be poor biomarkers of exposure to their precursor phthalates and may explain the relatively low frequency of detection of these monoester metabolites in human populations. MCPP and MnOP were also measured in 267 human urine samples. The frequent detection and higher urinary concentrations of MCPP than MnOP suggest that exposure to DnOP might be higher than previously thought based on the measurements of MnOP alone. However, because MCPP is also a minor metabolite of DBP and other phthalates in rats, and the metabolism of phthalates in rodents and humans may differ, additional data on the absorption, distribution, metabolism, and elimination of MCPP are needed to completely understand the extent of human exposure to DnOP from the urinary concentrations of MCPP.

Sprague-Dawley rats were administered ... 5,000 parts per million (ppm) di-n-octyl phthalate (DNOP) in their diet for 13 weeks. Similar control groups received either 4% corn oil or 5000 ppm of di(2-ethylhexyl) phthalate (DEHP). ... Trace quantities (3-5 ppm) of DEHP and DNOP were detected in the liver, and 15-31 ppm were found in adipose tissue ... .

... Male CD rats /were dosed/ by gavage with 0.2 mL DnOP and collected urine for analysis of metabolites. They recovered 31% of the dose in the urine by 48 hours. The monoester and some free phthalic acid were detected, but no parent DnOP was observed. Blood levels of the monoester, mono-octylphthalate, were measured in rats following administration of 2,000 mg/kg of DnOP by gavage. The biological halflife in the blood was 3.3 hours with an area under the curve (AUC) of 1,066 ug/hr/mL. Peak blood levels were observed at 3 hours following administration.

Following an oral dose of 2,000 mg/kg DnOP to rats, mono-octylphthalate was found in blood and testes in 3-6 hours.

용도 및 제조

Uses · 6건

Used as a plasticizer and dye carrier for film, wire, cables, and adhesives; [HSDB] Used as a plasticizer in carpet backing, packaging films, medical tubing, blood storage bags, floor tile, wire, cables, and adhesives; Also used in cosmetics and pesticides; [ATSDR ToxProfiles]

Working with Glues and Adhesives [Category: Other]

There are no known commercial uses for pure DnOP. However, DnOP constitutes approximately 20% of C6-10 phthalate substance. ... C6-10 phthalate substance is used in PVC utilized in the manufacture of flooring and carpet tile, canvas tarps, swimming pool liners, notebook covers, traffic cones, toys, vinyl gloves, garden hoses, weather stripping, flea collars, and shoes. DnOP-containing phthalate substances are also used in PVC intended for food applications such as seam cements, bottle cap liners, and conveyor belts.

Di-n-octylphthalate is principally used as a plasticizer in the production of plastics and PVC resins. When used as a plasticizer, di-n-octylphthalate can represent 5-60% of the total weight of the plastics and resins. It increases flexibility and enhances or alters the properties of the material. It is also used for cellulose ester and polystyrene resins, as a dye carrier in plastic production (primarily PVC), and as a chemical intermediate in the manufacture of adhesives, plastisols, and nitrocellulose lacquer coatings. ... Di-n-octylphthalate also serves as a carrier for catalysts or initiators and as a substitute for electrical capacitor fluid.

Monomeric plasticizer for vinyl and cellulosic resins.

PLASTICIZER FOR POLYSTYRENE RESINS

U.S. Exports(1987) 3.18X10+7 LB /DIOCTYL PHTHALATES/
U.S. Production · 6건

2023: <75,000 lb

(1978) GREATER THAN 2.27X10+6 G

(1982) GREATER THAN 2.27X10+6 G

(1985) 2.75X10+8 lb /DIOCTYL PHTHALATE/

(1986) 2.90X10+8 LB /DIOCTYL PHTHALATE/

For more U.S. Production (Complete) data for DI-N-OCTYL PHTHALATE (10 total), please visit the HSDB record page.

Consumption PatternsESSENTIALLY 100% AS A PLASTICIZER
Consumer UsesAdhesion/cohesion promoter
Industry UsesAdhesion/cohesion promoter
Methods of Manufacturing · 2건

Di-n-octylphthalate is produced commercially as a component of mixed phthalate esters, including straight- chain C6, C8, and Cl0 phthalates. Di-n-octylphthalate is produced at atmospheric pressure or in a vacuum by heating an excess of n-octanol with phthalic anhydride in the presence of an esterification catalyst such as sulfuric acid or p-toluenesulfonic acid. The process may be either continuous or discontinuous. Di-n-octylphthalate can also be produced by the reaction of n-octylbromide with phthalic anhydride.

n-Dioctyl phthalate is formed via the esterification of n-octanol with phthalic anhydride in the presence of a catalyst (sulfuric acid or p-toluenesulfonic acid) or noncatalytically at high temperature.

Formulations/PreparationsDinopol NOD
Use ClassificationChemical Classes -> Phthalates
General Manufacturing Information · 3건

Adhesive Manufacturing

1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester: ACTIVE

Di-n-octyl phthalate is sometimes mistakenly reported as its isomer, bis(2-ethyl-hexyl) phthalate, in the literature.

응용 분야 · 2건

용도Di-n-octyl phthalate is used as a plasticizer for many resins and elastomers. It acts as an additive. It is also used for medical tubing and blood storage bags, wire and cables, carpet back coating, floor tile and in cosmetics.

일반 설명A clear liquid with a mild odor. Slightly less dense than water and insoluble in water. Hence floats on water. Flash point 430°F. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. As a liquid, can easily penetrate the soil and contaminate groundwater and nearby streams. Eye contact may produce severe irritation and direct skin contact may produce mild irritation. Used in the manufacture of a variety of plastics and coating products.

상·하류 제품 정보

상류 원료

2-에틸-1-핵산올1-옥타놀프탈 산무수프탈산황산탄산나트륨(경회)

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)