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Dipentyl phthalate

HCID 8561
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
131-18-0
Standard SMILES
CCCCCOC(=O)c1ccccc1C(=O)OCCCCC
InChIKey
IPKKHRVROFYTEK-UHFFFAOYSA-N
Molecular formula
C18H26O4
Average molar mass
306.4 g/mol
Monoisotopic mass
306.18310931

Overview

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

Names & identifiers

Preferred name
Dipentyl phthalate
IUPAC
dipentyl benzene-1,2-dicarboxylate
English name
DI-N-PENTYL PHTHALATE-D4
Molecular formula
C18H26O4
Molecular weight
306.4

Names & synonyms

Dipentyl phthalate131-18-0DIAMYL PHTHALATEDi-n-pentyl phthalateAmyl phthalateAmoildipentyl benzene-1,2-dicarboxylatedi-n-Amyl phthalateDi-n-pentylphthalatePhthalic acid, dipentyl esterdiamylphthalatePhthalic Acid Diamyl Ester
Show more names
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

Database identifiers

CAS
131-18-0
PubChem CID
8561
DTXSID
DTXSID5031131
ChEMBL
CHEMBL1503330
ChEBI
CHEBI:34680

Properties

Computed structural properties

XLogP
5.8
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
12
Heavy atoms
22
Formal charge
0
Complexity
295

Experimental & physicochemical properties

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

log Kow = 5.62

4.85

OdorNearly odorless
Density · 2 items

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

1.022 at 20 °C

Color/FormColorless, oily liquid
Solubility · 4 items

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 items

357 °F (NTP, 1992)

357 °F; 180 °C (Closed cup)

245 dec F (118 °C) (Closed cup)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 4 items

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.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

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)

Uses & manufacturing

Uses · 3 items

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
Applications · 3 items

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
5DC92K224X
EC Number
205-017-9
Nikkaji
J46.841J
Endocrine Disruptors
Potential endocrine disrupting compound
Boiling Point · 2 items

648 °F at 760 mmHg (NTP, 1992)

342 °C

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

less than -67 °F (NTP, 1992)

FP: less than -55 °C

Physicochemical properties

Melting point
-55 °C · -55 °C
Boiling point
342 °C · 342 °C
Density
1.025 g/mL · 1.025 g/mL at 20 °C(lit.)
refractive index
20 · n20/D 1.490
Flash point
110 °C · >110°C
storage temp.
room temp
solubility
Chloroform (Slightly), Ethyl Acetate (Slightly)
form
Liquid
color
Clear colorless to slightly yellow
Odor
Mild, pleasant.
Water Solubility
Not miscible or difficult to mix in water.
BRN
1987323 · 1987323
Henry's Law Constant
1.1 · 1.1×101 mol/(m3Pa) at 25℃, HSDB (2015)
Major Application
environmental
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
Substances of Very High Concern (SVHC) Candidate List
Dipentyl phthalate (DPP) (131-18-0)
CAS DataBase Reference
131 · 131-18-0(CAS DataBase Reference)
FDA UNII
5 DC92K224X · 5DC92K224X
EPA Substance Registry System
Dipentyl phthalate (131-18-0)
UNSPSC Code
41116107 · 41116107
NACRES
61 · NB.61
Symbol(GHS)
8 · GHS08,GHS09
Signal word
Danger
Hazard statements
360 · H360-H400
Precautionary statements
201 · P201-P273-P308+P313
Hazard Codes
T,N
Risk Statements
60 · 60-61-50
Safety Statements
53 · 53-45-61
RIDADR
3082 · UN 3082 9/PG 3
WGK Germany
3 · 3
RTECS
1930000 · TI1930000
TSCA
TSCA listed
HazardClass
9 · 9
PackingGroup
III
HS Code
29173490 · 29173490
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
1 Repr · Aquatic Acute 1Repr. 1B
Hazardous Substances Data
131 · 131-18-0(Hazardous Substances Data)
Reactive Group
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special Reports · 3 items

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 item

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 items

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 items

Repr. 1B (99.3%)

Reproductive toxicity - category 1B

Reproductive toxicity - Category 1B

Repr. 1B

Safety & protection

Fire FightingFire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.
First Aid · 1 item

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 item

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 item

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 item

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 item

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)

Toxicology

Health Effects · 1 item

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 items

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 item

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 item

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 item

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 item

/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 item

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).

Safety data

wgk
3
tsca
TSCA listed
rtecs
TI1930000
ridadr
UN 3082 9/PG 3
hs_code
29173490
risk_code
60-61-50
Signal word
Danger
Symbol(GHS)
GHS08,GHS09
hazard_code
T,N
safety_code
53-45-61
hazard_class
9
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H360-H400
Hazard Classifications
Aquatic Acute 1Repr. 1B
Precautionary statements
P201-P273-P308+P313
Hazardous Substances Data
131-18-0(Hazardous Substances Data)

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

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

General DescriptionClear colorless to light yellow liquid. Practically odorless. Floats on water.

Upstream & downstream products

Upstream raw materials

Ferric sulfate1-PentanolPhthalic anhydride

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes

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