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Ditridecyl phthalate

pharmaceutical raw materials
Ditridecyl phthalate structure

Ditridecyl phthalate 

structure
  • CAS No:

    119-06-2

  • Formula:

    C34H58O4

  • Chemical Name:

    Ditridecyl phthalate

  • Synonyms:

    1,2-Benzenedicarboxylic acid,1,2-ditridecyl ester;Phthalic acid,ditridecyl ester;1,2-Benzenedicarboxylic acid,ditridecyl ester;1-Tridecanol,phthalate (2:1);Ditridecyl phthalate;Polycizer 962BPA;Staflex DTDP;Truflex DTDP;Bis(tridecyl) phthalate;Hexaplas DTDP;Jayflex DTDP;Di-n-tridecyl phthalate;Hatcol 2922

  • Categories:

    Analytical Chemistry  >  Standard

Description

Liquid


Nearly colorless oily liquid. Floats on water. (USCG, 1999)|Liquid


Nearly colorless oily liquid. Floats on water. (USCG, 1999)

Ditridecyl phthalate Basic Attributes

530.82

530.82

204-294-3

I7417R3544

DTXSID2025214|DTXSID1047027

Liquid

2917349000

Characteristics

52.60000

14.39

Nearly colorless oily liquid. Floats on water. (USCG, 1999)

0.951 g/cm3 @ Temp: 20 °C

-36.9°C

>285 °C @ Press: 5 Torr

274.2±10.7 °C

1.485

In water, 1.48X10-9 mg/L at 25 deg C (est)

2.51X10-11 mm Hg at 25 deg C (est)

Henry's Law constant = 2.23X10-4 atm-cu m/mol at 25 °C (est)

Pour point -37 °C|... Resistance to migration from polymers, low temperature flexibility ... compatibility with polar polymers and additives over a wide range of compositions. /Phthalate esters/|Phthalate esters would be expected to have UV maxima in the 230 nm and 270 nm regions. /Phthalate esters/|Hydroxyl radical reaction rate constant = 3.47X10-11 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

DITRIDECYL 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 [Handling Chemicals Safely, 1980. p. 250].

Safety Information

NONH for all modes of transport

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.

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, Ditridecyl phthalate (119-06-2), 20 pp. (2007) as of April 29, 2008.

Special Hazards of Combustion Products: Irritating vapor when heated. (USCG, 1999)

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P260, P261, P272, P280, P302+P352, P314, P321, P333+P313, P363, and P501

SMALL SPILLS AND LEAKAGE: If you spill this chemical, 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 alcohol followed by washing with a strong 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. STORAGE PRECAUTIONS: You should store this chemical in a refrigerator. (NTP, 1992)

Self-contained breathing apparatus and full turn out gear (Fire resistant helmet with full neck and face covers, self-contained breathing apparatus, flame resistant coat and pants, pair of boots). (USCG, 1999)

COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME.

To fight fire use dry chemical, carbon dioxide.|Water or foam may cause frothing.

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.

| 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.

Toxicity

LD50 Rat (Sprague-Dawley) oral >2000 mg/kg bw

/AQUATIC SPECIES/ Chronic toxicity studies were performed with commercial phthalate esters and Daphnia magna (14 phthalates) and rainbow trout (Oncorhynchus mykiss) (six phthalates). For the lower-molecular-weight phthalate esters - dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), and butylbenzyl phthalate (BBP) - the results of the studies indicated a general trend in which toxicity for both species increased as water solubility decreased. The geometric mean maximum acceptable toxicant concentration (GM-MATC) for D. magna ranged from 0.63 to 34.7 mg/L. For the higher-molecular-weight phthalate esters - dihexyl phthalate (DHP), butyl 2-ethylhexyl phthalate (BOP), di-(n-hexyl, n-octyl, n-decyl) phthalate (610P), di-(2-ethylhexyl) phthalate (DEHP), diisooctyl phthalate (DIOP), diisononyl phthalate (DINP), di-(heptyl, nonyl, undecyl) phthalate (711P), diisodecyl phthalate (DIOP), diundecyl phthalate (DUP), and ditridecyl phthalate (DTDP) - the GM-MATC values ranged from 0.042 to 0.15 mg/L. Survival was equally sensitive and sometimes more sensitive than reproduction. The observed toxicity to daphnids with most of the higher-molecular-weight phthalate esters appeared to be due to surface entrapment or a mode of toxicity that is not due to exposure to dissolved aqueous-phase chemical. Early life-stage toxicity studies with rainbow trout indicated that survival (DMP) and growth (DBP) were affected at 24 and 0.19 mg/L, respectively.

Ditridecyl phthalate's production and use as a plasticizer(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an average Koc value of 1.2X10+6(2), indicates that ditridecyl phthalate is expected to be immobile in soil(SRC). Volatilization of ditridecyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Ditridecyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-11 mm Hg(SRC), determined from a fragment constant method(4). Using an inoculum obtained from soil and sewage sludge, ditridecyl phthalate underwent >50% primary biodegradation under aerobic conditions in 28 days, and 37% mineralization to carbon dioxide during the same time period(5).|AQUATIC FATE: Based on a classification scheme(1), an average Koc value of 1.2X10+6(2), indicates that ditridecyl 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 2.2X10-4 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 16 hours and 12 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 volatilization half-life from a model pond is about 5600 years when adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 13.45(7) and a regression-derived equation(8), 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 7.7 years and 280 days at pHs 7 and 8, respectively(9). Ditridecyl phthalate underwent 51.5% biodegradation in a semi-continuous activated sludge test under aerobic conditions in 24 hrs, and complete degradation was observed in 12 days in an activated sludge die-away test under aerobic conditions(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ditridecyl phthalate, which has an estimated vapor pressure of 2.5X10-11 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 ditridecyl phthalate may be removed from the air by wet or dry deposition(SRC). Ditridecyl 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 ditridecyl phthalate with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 2.9X10-2 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). Ditridecyl phthalte 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 ditridecyl phthalate(SRC), using an estimated log Kow of 13.45(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 average Koc of (14)C-ditridecyl phthalate using three standard USEPA sediments (supplied and characterized by the EPA) was measured at 1.2X10+6(1). According to a classification scheme(2), this Koc value suggests that ditridecyl phthalate is expected to be immobile in soil.

The Henry's Law constant for ditridecyl phthalate is estimated as 2.2X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ditridecyl 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 16 hours(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 12 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 5600 years when adsorption is considered(3). Ditridecyl phthalate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Ditridecyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-11 mm Hg(SRC), determined from a fragment constant method(4).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 21,225 workers (555 of these were female) were potentially exposed to ditridecyl phthalate in the US(1). Occupational exposure to ditridecyl phthalate may occur through inhalation of aerosols and dermal contact with this compound at workplaces where ditridecyl phthalate is produced or used(SRC). Use data indicate that the general population may be exposed via inhalation of particulates and dermal contact with consumer products containing this compound(SRC).

Drug Information

Mist or fumes from hot processing may cause irritation, nausea and vomiting. (USCG, 1999)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Ditridecyl phthalate Use and Manufacturing

Uses

Functional fluids (closed systems)


Lubricants and greases

Production

(1972) 1.09X10+10 G|(1975) 7.12X10+9 G|1,2-Benzenedicarboxylic acid, ditridecyl 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#1147]

100% AS A VINYL PLASTICIZER

All other chemical product and preparation manufacturing|1,2-Benzenedicarboxylic acid, 1,2-ditridecyl 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/

Computed Properties

Molecular Weight:530.8
XLogP3:14.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:28
Exact Mass:530.43351033
Monoisotopic Mass:530.43351033
Topological Polar Surface Area:52.6
Heavy Atom Count:38
Complexity:499
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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