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Dimethoxyethyl phthalate

HCID 8344
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Basic information

CAS
117-82-8
Standard SMILES
COCCOC(=O)c1ccccc1C(=O)OCCOC
InChIKey
HSUIVCLOAAJSRE-UHFFFAOYSA-N
Molecular formula
C14H18O6
Average molar mass
282.29 g/mol
Monoisotopic mass
282.11033829

Overview

bis(2-methoxyethyl) phthalate has been reported in Lonicera japonica with data available.

Names & identifiers

Preferred name
Dimethoxyethyl phthalate
IUPAC
bis(2-methoxyethyl) benzene-1,2-dicarboxylate
English name
Bis(2-methoxyethyl) phthalate
Molecular formula
C14H18O6
Molecular weight
282.29

Names & synonyms

Dimethoxyethyl phthalateDi(2-methoxyethyl)phthalateRefChem:568783BIS(2-METHOXYETHYL) PHTHALATE117-82-8Kesscoflex MCPDimethylglycol phthalate2-Methoxyethyl phthalateDi(2-methoxyethyl) phthalateMethyl glycol phthalateBis(methoxyethyl) phthalateKodaflex DMEP
Show more names
phthalatemethoxBis PhthalatedimethoxyethylphthalateReomol P
Dimethoxy ethyl phthalatebis(methoxyethyl)phthalatebis(2-methoxyethyl) benzene-1,2-dicarboxylateBis(methylglycol) phthalateNSC 2147Bis(2-methoxyethyl)phthalatePhthalic acid, di(methoxyethyl) esterDTXSID8025094

Database identifiers

CAS
117-82-8
PubChem CID
8344
DTXSID
DTXSID8025094
ChEMBL
CHEMBL1302251
UNII
68W8XUO221
EC Number
204-212-6
Nikkaji
J3.615C

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
71.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
10
Heavy atoms
20
Formal charge
0
Complexity
274

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Phthalate Esters
SpringerMaterials PropertiesViscosity
Odor · 2 items

VERY SLIGHT

Mild odor

Density1.1596 g/cu cm at 20 °C
Viscosity32 cP
Color/Form · 2 items

Oily liquid

PRACTICALLY COLORLESS, OILY LIQ

Solubility · 5 items

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

SLIGHTLY SOL IN WATER (0.8%) @ 20 °C

MISCIBLE WITH ABSOLUTE ALC

INSOL IN MINERAL OILS

In water, 8500 mg/L, temperature not specified

Flash Point410 °F (210 °C) (Open cup)
Endocrine DisruptorsPotential endocrine disrupting compound

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

H360Df: May damage the unborn child; Suspected of damaging fertility [Danger Reproductive toxicity]

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

Danger

H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]

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

Hazard information

Regulatory Information · 4 items

Chemical: 1,2-Benzenedicarboxylic acid, bis(2-methoxyethyl) ester

Hazard Traits - Reproductive Toxicity

Regulation (EC) No 178/2002 (amended)

Substance: Bis(2-methoxyethyl) phthalate

Other Safety InformationIMAP assessments - C4-6 side chain transitional phthalates: Human health tier II assessment
Fire PotentialCombustible
Hazards SummaryA mild irritant; [MSDSonline] Like dibutyl phthalate, it may cause CNS depression, mild liver toxicity, and possibly teratogenic effects after ingestion of large amounts; [HSDB] See PHTHALATE ESTERS.
Special Reports · 5 items

USEPA; Health and Environmental Effects Profile for Phthalate Esters; (1980) ECAO-CIN-146

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

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

Woodward KN (ed); Phthalate Esters: Toxicity and Metabolism (1988)

For more Special Reports (Complete) data for BIS(2-METHOXYETHYL) PHTHALATE (6 total), please visit the HSDB record page.

Chemistry & industry

Uses & manufacturing

Uses · 5 items

Used as a plasticizer (especially for cellulose acetate), a solvent, and in molding compositions, adhesives, laminating cements, and flash bulb lacquers; [HSDB]

Working with Glues and Adhesives [Category: Other]

... Plasticizer for cellulosic resins and some vinyl ester resins.

Plasticizer, especially for cellulose acetate; solvent

Molding compositions, adhesives, laminating cements, and flash bulb lacquers

U.S. Production · 3 items

(1977) PROBABLY GREATER THAN 2.27X10+6 G

(1979) PROBABLY GREATER THAN 2.27X10+6 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5017]

Methods of ManufacturingEthylene glycol monomethyl ether + phthalic anhydride (esterification)
Formulations/PreparationsKodaflex DMEP, 99.0% min assay (ester content)
General Manufacturing Information · 5 items

1,2-Benzenedicarboxylic acid, 1,2-bis(2-methoxyethyl) ester: ACTIVE

IN ITALY DIMETHOXYETHYL PHTHALATE IS LISTED AS BEING PERMITTED FOR USE WITH FOOD.

... /DIMETHYLGLYCOL PHTHALATE/ IMPARTS EXCELLENT LIGHT-RESISTANCE TO PLASTICS & IS EXCELLENT GELLING AGENT FOR NITROCELLULOSE, CELLULOSE ACETATE, POLYVINYL ACETATE, POLYVINYL CHLORIDE, & POLYVINYLIDENE CHLORIDE, & ALSO FOR VINYL CHLORIDE-VINYL ACETATE COPOLYMERS.

... /DIMETHYLGLYCOL PHTHALATE/ IS ONE OF THE BEST PLASTICIZERS FOR CELLULOSE ACETATE & HAS ADVANTAGE OF NOT BLEEDING, WHATEVER GRADE OF CELLULOSE ACETATE USED.

Compatible with nitrocellulose, cellulose acetate butyrate, ethyl cellulose, chlorinated rubber, polyvinyl resins and methyl methacrylate

Applications · 3 items

UsesPlasticizer; solvent

UsesIt finds it application in cosmetic industry. It is also used as a plasticizer for toys, including inflatable water products, hoppers, play and exercise balls.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Boiling Point · 2 items

340 °C

BP: 230 deg at 10 mm Hg

DecompositionWhen heated to decomp it emits acrid smoke and irritating fumes.
Melting PointFreezing point: -45 °C

Physicochemical properties

Melting point
-42.4 °C · -42.4°C
Boiling point
230 °C10 · 230 °C10 mm Hg(lit.)
Density
1.173 g/mL · 1.173 g/mL at 20 °C(lit.)
refractive index
20 · n20/D 1.503
Flash point
230 °C/10mm · 230°C/10mm
storage temp.
Refrigerator
solubility
Chloroform (Slightly), Ethyl Acetate (Slightly)
form
Liquid
Specific Gravity
1.17 · 1.17
color
Colorless
Water Solubility
8500 mg/L · Soluble in water 8500 mg/L at 25°C.
BRN
2056929 · 2056929
Henry's Law Constant
2.3 · 2.3×101 mol/(m3Pa) at 25℃, Fishbein and Albro (1972)
Major Application
cleaning productscosmeticsenvironmentalfood and beveragespersonal care
InChI
1S/C14H18O6/c1-17-7-9-19-13(15)11-5-3-4-6-12(11)14(16)20-10-8-18-2/h3-6H,7-10H2,1-2H3
InChIKey
HSUIVCLOAAJSRE-UHFFFAOYSA-N
SMILES
COCCOC(=O)c1ccccc1C(=O)OCCOC
Substances of Very High Concern (SVHC) Candidate List
Bis(2-methoxyethyl) phthalate (117-82-8)
CAS DataBase Reference
117 · 117-82-8(CAS DataBase Reference)
FDA UNII
68 W8XUO221 · 68W8XUO221
NIST Chemistry Reference
Phthalic acid, di(2-methoxyethyl)ester(117-82-8)
EPA Substance Registry System
Bis(2-methoxyethyl) phthalate (117-82-8)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
360 · H360
Precautionary statements
201 · P201-P202-P280-P308+P313-P405-P501
PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
T
Risk Statements
61 · 61-62
Safety Statements
53 · 53-45
WGK Germany
3 · 3
RTECS
1400000 · TI1400000
TSCA
TSCA listed
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 B · Repr. 1B
Hazardous Substances Data
117 · 117-82-8(Hazardous Substances Data)
Flammable Limits
Lower flammable limit: 0.7% by volume at 440 °F (227 °C)
NFPA Hazard Classification · 3 items

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

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.

Peroxide Forming Chemical · 3 items

Bis(2-methoxyethyl) phthalate

D: Other compounds that may form peroxides

Kelly

Hazard Classes and Categories · 4 items

Repr. 1B (100%)

Reproductive toxicity - category 1B

Reproductive toxicity - Category 1B

Repr. 1B

Hazardous Reactivities and Incompatibilities... Can react with oxidizing materials.

Safety & protection

Fire Fighting ProceduresAlcohol foam. Water or foam may cause frothing.
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.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 38(SRC), determined from a water solubility of 8500 mg/L(2) and a regression-derived equation(3), indicates that bis(2-methoxyethyl) phthalate is expected to have very high mobility in soil(SRC). Volatilization of bis(2-methoxyethyl) phthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Bis(2-methoxyethyl) phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-4 mm Hg(SRC), determined from a fragment constant method(5). Bis(2-methoxyethyl) phthalate was biodegraded 19.3% using an enzyme extracted from N. erythropolis(6), suggesting that bis(2-methoxyethyl) phthalate is susceptible to biodegradation(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 38(SRC), determined from a water solubility of 8500 mg/L(2}and a regression-derived equation(3), indicates that bis(2-methoxyethyl) phthalate 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 2.8X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1.4(SRC), from an estimated log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 1.3 years and 49 days at pHs 7 and 8, respectively(8). Bis(2-methoxyethyl) phthalate was biodegraded 19.3% using an enzyme extracted from Nocardia erythropolis(9), suggesting that bis(2-methoxyethyl) phthalate may be susceptible to biodegradation(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-methoxyethyl) phthalate, which has an estimated vapor pressure of 2.3X10-4 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 bis(2-methoxyethyl) 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 20 hours(SRC), calculated from its rate constant of 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Bis(2-methoxyethyl) 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.
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=117-82-8][Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=117-82-8]

Soil Adsorption/Mobility · 1 item

The Koc of bis(2-methoxyethyl) phthalate is estimated as 38(SRC), using a water solubility of 8500(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bis(2-methoxyethyl) phthalate is expected to have very high mobility in soil.

TSCA Test Submissions · 1 item

The effects of acute oral exposure to bis(methoxyethyl) phthalate (MEP) by gavage in male Wistar rats (20 in control group (water), 5/treated group, number of treated groups not reported) were determined. MEP (1000, 1500 or 2000 mg/kg) was administered in a single dose and the rats were necropsied on the 11th day following dosing. There were differences between treated and control animals in the following: decreased testes weights (all treated groups), increased sperm head count (high-dose level), and a highly significant increase in the percentage of abnormal sperm heads, including straight heads (i.e. no hook), excessive curvature of heads, folded, coiled, thin or amorphous heads (high- and mid-dose groups). There were no significant differences between treated and control animals in the following: clinical observations, and histopathology of the testes.

Artificial Pollution SourcesBis(2-methoxyethyl) phthalate's production and use as a plasticizer, especially for cellulose acetate, and as a solvent(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 item

AEROBIC: Bis(2-methoxyethyl) phthalate was biodegraded 19.3% using an enzyme extracted from Nocardia erythropolis(1). When present at 3,000 ppm, the compound was not degradaded after 40 days incubation at 30 °C using the soil microbe Pseudomonas acidovorans 256-1(2).

Environmental Bioconcentration · 1 item

An estimated BCF of 1.4 was calculated in fish for bis(2-methoxyethyl) phthalate(SRC), using an estimated log Kow of 1.11(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for bis(2-methoxyethyl) phthalate is estimated as 2.8X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bis(2-methoxyethyl) phthalate is expected to be essentially nonvolatile from water surfaces(2). Bis(2-methoxyethyl) phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 items

/LABORATORY ANIMALS: Acute Exposure/ Tests were carried out on adult Wistar rats, weighing 300-350 g. The dimethoxyethyl phthalate was mixed with a very small amt of absolute alc ... to dilute it & assist absorption. Ingesting 2 g/kg body wt did not cause death of 6 rats which received the dose. At 2.5 g/kg, 3 rats out of 12 died /within/ 36 hr after ingestion, & others survived. At 2.75 g/kg, 5 rats out of 10 died between 25 & 36 hr after ingestion.

/LABORATORY ANIMALS: Acute Exposure/ Application to rabbit and guinea pig skin causes slight irritation. Instillation of 100 mg into rabbit eyes causes mild irritation.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In rats inhaling dimethoxyethyl phthalate 6 hr/d for 62 days, a no-effect level of 145 ppm was observed.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of rats were treated with 0, 100, or 1000 mg/kg by oral intubation for 2 wk. Body weight and food consumption was reduced at 1000 mg/kg. Hemoglobin and hematocrit values were reduced at 100 and 1000 mg/kg; erythrocyte and leukocyte counts were reduced at 1000 mg/kg. Absolute liver, kidney, thymus, and testes weights were decreased at 1000 mg/kg, as were relative thymus and testes weights. Thymic and testicular atrophy were observed as was a decrease in spermatogonia.

For more Non-Human Toxicity Excerpts (Complete) data for BIS(2-METHOXYETHYL) PHTHALATE (23 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of bis(2-methoxyethyl) phthalate with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.16 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 1.3 years and 49 days at pH values of 7 and 8, respectively(2). Bis(2-methoxyethyl) phthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1 item

NIOSH (NOES Survey 1981-1983) has statistically estimated that 68 workers (0 of these were female) were potentially exposed to bis(2-methoxyethyl) phthalate in the US(1). Occupational exposure to bis(2-methoxyethyl) phthalate may occur through dermal contact with this compound at workplaces where bis(2-methoxyethyl) phthalate is produced or used(SRC). Use data indicate that the general population may be exposed via inhalation and dermal contact with consumer products containing this compound(SRC).

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
TI1400000
hs_code
29173490
risk_code
61-62
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
T
safety_code
53-45
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements
H360
Hazard Classifications
Repr. 1B
Precautionary statements
P201-P202-P280-P308+P313-P405-P501
Hazardous Substances Data
117-82-8(Hazardous Substances Data)

UsesBis(2-methoxyethyl) Phthalate is a phthalate derivative found in cosmetic products.

Upstream & downstream products

Upstream raw materials

2-Methoxyethanol