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Home > Encyclopedia > Didecyl phthalate

Didecyl phthalate

Didecyl phthalate structure

Didecyl phthalate 

structure
  • CAS No:

    84-77-5

  • Formula:

    C28H46O4

  • Chemical Name:

    Didecyl phthalate

  • Synonyms:

    1,2-Benzenedicarboxylic acid,1,2-didecyl ester;Phthalic acid,didecyl ester;1,2-Benzenedicarboxylic acid,didecyl ester;Didecyl phthalate;Di-n-decyl phthalate;Decyl phthalate;Vinycizer 105;Bis(n-decyl)phthalate;NSC 15319;DDP;Dicapryl phthalate

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

clear light yellow viscous liquid


Di-n-decyl phthalate is a phthalate ester and a diester.

Didecyl phthalate Basic Attributes

446.66

446.66

201-561-6

FI5FBN947Z

15319

DTXSID3026512

Light-colored liquid|Viscous liquid|COLORLESS

2917349000

Characteristics

52.6

11.2

clear light yellow viscous liquid

0.9675 g/cm3 @ Temp: 20 °C

<25 °C

261 °C @ Press: 5 Torr

243.7±9.3 °C

1.488

0.33mg/L(24 ºC)

7.89X10-9 mm Hg at 25 deg C (est)

PRACTICALLY ODORLESS

Henry's Law constant = 2.81X10-5 cu cm/molec-sec at 25 °C (est)

VP: 0.3 mm Hg at 200 °C. Bulk density: 8.05 lb/gal|Most phthalate esters have a relatively high calculated log octanol/water partition coefficient > 2.12 indicating that they are lipophilic. /Phthalate esters/|Phthalate esters would be expected to have UV maxima in the 230 nm and 270 nm regions. /Phthalate esters/|... Resistance to migration from polymers, low temperature flexibility ... compatibility with polar polymers and additives over a wide range of compositions. /Phthalate esters/|Hydroxyl radical reaction rate constant = 2.62X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

1

S24/25

TI0900000

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.

...Can react with oxidizing materials.

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)|EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from the Database Query page at: http://www.epa.gov/hpv/pubs/hpvrstp.htm on Phthalate Esters Category: 1,2-Benzenedicarboxylic acid, didecyl ester (84-77-5), 23 pp. (2006) as of April 22, 2008.

Combustible

To fight fire, use foam, carbon dioxide, dry chemical.

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.

INDOOR AIR: Didecyl phthalate was detected in association with airborne particulates collected at telephone office sites at a representative concn of 20.0 ng/cu m(1).

Toxicity

LD50 Rabbit dermal 17000 mg/kg

/AQUATIC SPECIES/ The extensive database of acute and chronic aquatic toxicity data for 18 phthalate esters was reviewed and summarized for freshwater and saltwater aquatic microorganisms, algae, invertebrates, and fish. Phthalate esters have been tested with six species of microorganisms, including bacteria and protozoans. Fifteen algal species have been tested, including green and bluegreen algae in both freshwater and saltwater. Nineteen freshwater and saltwater invertebrate species inhabiting surface waters and sediments and 21 freshwater and saltwater fish inhabiting cold and warm water bodies have been tested. The results of most studies indicate that acute and chronic toxicity to microorganisms, algae, aquatic invertebrates, and fish are limited to the lower molecular weight phthalate esters (i.e., dimethyl-, diethyl-, diallyl-, dipropyl-, dibutyl-, diisobutyl-, and butylbenzylphthalate). In contrast, higher molecular weight phthalate esters are not acutely or chronically toxic to aquatic organisms. Although conflicting data on chronic effects for high molecular weight phthalate esters have been reported for daphnids, these inconsistencies are attributed to physical effects imposed on daphnids when exposed to test concentrations in excess of true water solubilities. Altogether, nearly 400 test results covering more than 60 species of microorganisms, algae, invertebrates, and fish are reported for both freshwater and saltwater aquatic species. While most investigators used several common species and standard protocols to assay conventional endpoints, many nontraditional species and toxicological endpoints were also used. This has created a toxicological database of both sufficient depth to compare many similar tests and sufficient breadth to encompass virtually al important types of aquatic habitats and classes of aquatic species.

Didecyl phthalate's production and use as a plasticizer, especially for vinyl resins(1), may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.0X10+6(SRC), determined from a log Kow of 9.05(2) and a regression-derived equation(3), indicates that didecyl phthalate is expected to be immobile in soil(SRC). Volatilization of didecyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Didecyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.9X10-9 mm Hg(SRC), determined from a fragment constant method(5). Using an inoculum obtained from soil and sewage sludge, didecyl phthalate, as a mixture with dioctyl and dihexyl phthalate, underwent greater than 99% primary biodegradation under aerobic conditions in 28 days(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.0X10+6(SRC), determined from a log Kow of 9.05(2) and a regression-derived equation(3), indicates that didecyl phthalate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.8X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.0 and 28 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 600 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Estimated hydrolysis half-lives of 7.7 years and 280 days at pHs 7 and 8, respectively, suggest that hydrolysis is not expected to be an important process(8). Didecyl phthalate, present at 1 ug/L, had a half-life of 1.4 days in a river die-away test(9). Didecyl phthalate underwent 1% biodegradation after 15 days using a settled domestic wastewater inoculum, and approximately 10% biodegradation in 15 days after the inoculum was acclimated to this compound(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), didecyl phthalate, which has an estimated vapor pressure of 7.9X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase didecyl phthalate may be removed from the air by wet or dry deposition(SRC). Didecyl phthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of didecyl phthalate with photochemically-produced hydroxyl radicals has been estimated as 2.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.029 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 7.7 years and 280 days at pH values of 7 and 8, respectively(2). Didecyl phthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for didecyl phthalate(SRC), using an estimated log Kow of 9.05(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).

The Koc of didecyl phthalate is estimated as 2.0X10+6(SRC), using a log Kow of 9.05(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that didecyl phthalate is expected to be immobile in soil.

The Henry's Law constant for didecyl phthalate is estimated as 2.8X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that didecyl phthalate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3.0 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 28 days(SRC). However, adsorption to soil is expected to attenuate volatilization(SRC). The volatilization half-life from a model pond is about 600 years when adsorption is considered(3). Didecyl phthalate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Didecyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.9X10-9 mm Hg(SRC), determined from a fragment constant method(4).

DRINKING WATER: Didecyl phthalate was qualitatively identified in British drinking water derived from lowland river water and groundwater sources, and in a lowland river in Germany(1).

Occupational exposure to didecyl phthalate may occur through inhalation and dermal contact with this compound at workplaces where didecyl phthalate is produced or used. Use data indicate that the general population may be exposed to didecyl phthalate via inhalation of particulates and dermal contact with consumer products containing didecyl phthalate. (SRC)

Drug Information

/OTHER TOXICITY INFORMATION/ To compare changes in platelets stored in the new di-n-decyl phthalate (DnDP)-plasticized polyvinyl chloride (PVC) bag with those in a di-(2-ethylhexyl)phthalate (DEHP)-plasticized PVC bag, a single-donor apheresis platelet concentrates (PCs), 133 +/- 11 x 10(7) platelets per mL (n=7), were stored with 94 +/- 3 mL of plasma in a new 1-liter bag with a surface area of 44 +/- 7.1 sq cm per 10(10) platelets. Oxygen and carbon dioxide gas diffusion properties of PVC-DnDP films were respectively, 1.6 and 2 times those of standard PVC-di-(2-ethylhexyl)phthalate films. The amounts of DnDP leaked into the plasma of PCs were low at 0.58 +/- 0.06 mg per bag after 5-day storage, which is about 1/80 the amount of di-(2-ethylhexyl)phthalate leaked. The pH of PCs in PVC-DnDP bags amounted to 6.99 +/- 0.03 after 5-day storage, with glycolysis accelerated somewhat in the new bags. However, the platelet oxygen consumption was no different from that in the PVC-di-(2-ethylhexyl)phthalate bags. Platelet aggregation and response to hypotonic shock were significantly better in the new bags at the end of storage. Shape changes of platelets into spherical forms with dendrites were more frequently observed in PVC-DnDP bags than in PVC-di-(2-ethylhexyl)phthalate bags. The study indicated that platelets stored in the new DnDP-plasticized PVC bags have retained aggregation and response to hypotonic shock more than platelets in the PVC-di-(2-ethylhexyl)phthalate bags, but spherical forms and anaerobic metabolism increased in the new bags.

di-n-decyl phthalate

Didecyl phthalate Use and Manufacturing

Methods of Manufacturing

Add 2.0g to 50mL DMF solventPhthalic acid (0.012 mol) and 4.8 g potassium hydrogencarbonate (0.048 mol), Stir at room temperature to form a potassium salt.6.64 g of n-bromodecane (0.03 mol) was added to the mixed solution, The reaction was stirred at 90 C for 12 hours.Stop the reaction and allow the solution to cool to room temperature.It was poured into 300 mL of water and extracted with ethyl acetate.Dry over anhydrous sodium sulfate, filter and spin dry solvent.The crude product was subjected to column chromatography using petroleum ether/ethyl acetate (24/1) as eluent.

Uses

Didecyl Phthalate is a primary plasticizer for vinyl resins and also shown to be compatible with polystyrene and cellulosics.

Production

1,2-Benzenedicarboxylic acid, didecyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5316]

1,2-Benzenedicarboxylic acid, 1,2-didecyl ester: ACTIVE|The first step, alcoholysis of phthalic anhydride (PA) to give the monoester, is rapid and goes to completion. The reaction generally starts at elevated temperatures and proceeds exothermically. The second step is the conversion of the monoester to a diester with the formation of water. This is a reversible reaction and proceeds more slowly than the first, thus determining the overall rate of reaction. To shift the equilibrium towards the diester, the water of reaction is removed by distillation. The rate of reaction can be influenced by the choice of catalyst and the reaction temperature. For fast conversion rates, high reaction temperatures are generally used. However, these are influenced by the boiling point of the alcohol and/or the type of catalyst. ... Currently, nearly all major phthalate producers use amphoteric catalysts for the esterification of high boiling alcohols. ... The reaction temperatures for the amphoteric catalysts are about 200 °C. At this temperature side reactions are minimized, and the alcohol can be recycled without purification. By using this type of catalyst, over 99.5 % conversion to diester can be achieved. /Phthalates/|IT IS COMPATIBLE WITH CHLORINATED RUBBER, GOVERNMENT RUBBER STYRENE (GRS), NITROCELLULOSE, ETHYL CELLULOSE, POLYVINYL CHLORIDE, & ACETATE COPOLYMERS.|... IN MANUFACTURE OF ELECTRIC CABLES BECAUSE OF ITS LOW VOLATILITY, GOOD DIELECTRIC PROPERTIES, & COLD RESISTANCE. ... ALSO USED FOR MAKING PLASTISOLS, GIVING PARTICULARLY FLUID PASTES, & HAVING LONG SHELF LIFE WITHOUT INCREASE IN VISCOSITY.|IT IS PRIMARY PLASTICIZER FOR POLYVINYL CHLORIDE. ... MARKEDLY LESS VOLATILE THAN OTHER PLASTICIZERS & MAKES POSSIBLE MFR OF ARTICLES RESISTANT TO HIGH TEMP. IT IS HYDROPHOBIC & EXHIBITS GOOD RESISTANCE TO EXTRACTION BY DETERGENTS.

DIDECYL PHTHALATE WAS EXTRACTED FROM WATER WITH PETROLEUM ETHER ALONE OR WITH ETHANOL, PURIFIED ON FLORISIL AND DETERMINED BY GAS CHROMATOGRAPHY/ELECTRON CAPTURE DETECTION. THE SENSITIVITY FOR PHTHALATES WAS 1-10 NG.

Computed Properties

Molecular Weight:446.7
XLogP3:11.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:22
Exact Mass:446.33960994
Monoisotopic Mass:446.33960994
Topological Polar Surface Area:52.6
Heavy Atom Count:32
Complexity:420
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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