84-75-3CCCCCCOC(=O)c1ccccc1C(=O)OCCCCCCKCXZNSGUUQJJTR-UHFFFAOYSA-NDi-n-hexyl Phthalate (DnHP) can cause female reproductive toxicity and male reproductive toxicity according to The National Toxicology Program's Center for the Evaluation of Risks to Human Reproduction.
log Kow = 6.82
5.8
0.995 at 68 °F (NTP, 1992) - Less dense than water; will float
1.010-1.016 at 20 °C/20 °C
0.995
0.995
Insoluble (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/
In water, 0.05 mg/L at 25 °C
350 °F (NTP, 1992)
381 °F; 193 °C /(method not specified)/
350 °F
350 °F
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Danger
H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 6.2% (3 of 48) of reports.
Danger
H360 (91.7%): May damage fertility or the unborn child [Danger Reproductive toxicity]
Chemical: 1,2-Benzenedicarboxylic acid, dihexyl ester
Hazard Traits - Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Immunotoxicity; Reproductive Toxicity; Respiratory Toxicity
Substance: Dihexyl phthalate
1,2-Benzenedicarboxylic acid, dihexyl 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.
May cause skin and eye irritation; [CAMEO] Like dioctyl phthalate, it may cause CNS depression and mild liver toxicity after ingestion of large amounts; [HSDB] An irritant; Effects in high-dose animal studies include fatty liver degeneration and hepatitis; [MSDSonline] See PHTHALATE ESTERS.
n-Hexanol is a metabolite of DnHP. Hexanol is oxidized to the fatty acid and metabolized by the fatty acid oxidation pathway.
Strains of Mycobacterium and Nocardia isolated because of their ability to use di(2-ethylhexyl) phthalate (DEHP) as sole carbon source also grew on diethyl, diisooctyl, and butyl benzyl phtalates. As the two bacteria grew on di(2-ethylhexyl) phthalate , they excreted products that increased the solubility of di(2-ethylhexyl) phthalate and diisoctyl, dihexyl, and diisodecyl but not butyl benzyl or di-n-butyl phthalates. The solubilizer was produced by Mycobacterium sp even when grown on a water soluble substrate such as acetate. Addition of the solubilizer to culture media enhanced the degradation of di(2-ethylhexyl) phthalate and diisooctyl phthalate by Mycobacterium sp and Nocardia sp but not butyl benzyl phthalate. The extent of di(2-ethylhexyl) phthalate degradation by Mycobacterium sp in media amended with the solubilizer was reduced and the initiation of degradation was delayed if the solubilizer was first treated with protease. The effect of protease was not a result of its toxicity to Mycobacterium or use of the enzyme preparation for growth of the organism. The results thus show that microbial products increase the solubility of certain phthalates and enhance their degradation.
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)
No accumulation of dihexyl phthalate (25 or 250 ppm in the diet) occurred in starlings fed DHP for 30 days.
This study examined the extent of dermal absorption of a series of phthalate diesters in the rat. Those tested were dimethyl, diethyl, dibutyl, diisobutyl, dihexyl, di(2-ethylhexyl), diisodecyl, and benzyl butyl phthalate. Hair from a skin area (1.3 cm in diameter) on the back of male F344 rats was clipped, the 14(C)phthalate diester was applied in a dose of 157 mumol/kg, and the area of application was covered with a perforated cap. The rat was restrained and housed for 7 days in a metabolic cage that allowed separate collection of urine and feces. Urine and feces were collected every 24 hr, and the amount of (14)C excreted was taken as an index of the percutaneous absorption. At 24 hr, diethyl phthalate showed the greatest excretion (26%). As the length of the alkyl side chain increased, the amount of (14)C excreted in the first 24 hr decreased signficantly. The cumulative percentage dose excreted in 7 days was greatest for diethyl, dibutyl, and diisobutyl phthalate, about 50-60% of the applied (14)C; and intermediate (20-40%) for dimethyl, benzyl butyl, and dihexyl phthalate. Urine was the major route of excretion of all phthalate diesters except for diisodecyl phthalate. This compound was poorly absorbed and showed almost no urinary excretion. After 7 days, the percentage dose for each phthalate that remained in the body was minimal showed no specific tissue distribution. Most of the unexcreted dose remained in the area of application. These data show that the structure of the phthalate diester determines the degree of dermal absorption. Absorption maximized with diethyl phthalate and then decreased significantly as the alkyl side chain length increased.
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불러오는 중…
84-75-3DTXSID6025068CHEMBL3181956CHEBI:34678662 °F at 735 mmHg (NTP, 1992)
210 °C at 5 mm Hg
662 °F at 735 mmHg
662 °F at 735 mmHg
-72 °F (NTP, 1992)
-58 °C
-72 °F
-72 °F
It is a clear, oily liquid, with a melting point of -58°C and a boiling point of 340–350°C.
NTP/CERHR; Monograph on the Potential Human Reproductive and Developmental Effects of Di-n-Heptyl Phthalate (DnHP), 129 pp. (2003) NIH Publication No. 03-4489 includes: 1) the NTP Brief, 2) the Expert Panel Report on the Reproductive and Developmental Toxicity of DnHP, and 3) public comments received on the Expert Panel Report. As stated in the NTP Brief, ... the scientific evidence was insufficient to reach a conclusion regarding the potential for DnHP to adversely affect human development or reproduction. 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 (National Institute of Environmental Health Sciences, P.O. Box 12233, MD EC-32, Research Triangle Park, NC; fax: 919-316-4511).
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, Dihexyl phthalate (84-75-3), 27 pp. (2007) as of April 29, 2008.
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, dihexyl ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.
A testing consent order is in effect for di-n-hexyl phthalate for environmental effects and chemical fate testing. FR citation: 1/9/89.
DI-N-HEXYL 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. This compound can react with oxidizing materials and strong alkaline materials. (NTP, 1992)
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.
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.
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.
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.
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)
The effects of phthalate esters of branched chain alcohols, typified by di-(2-ethylhexyl)phthalate (DEHP) differ from those of esters of straight chain alcohols typified by di-n-hexyl phthalate (DnHP). The former induce liver enlargement and proliferation of hepatic peroxisomes, while the latter cause no peroxisome proliferation but cause fat accumulation in the liver. Both classes of phthalate esters are hypolipidaemic and cause thyroid changes associated with an increased rate of thyroglobulin turnover. As phthalate esters are used as mixtures, ... the effect of mixtures of the compounds /were examined/. Groups of five male Wistar albino rats were administered either control diet or diets containing either 10,000 ppm of DEHP, 10,000 ppm of DnHP or 10,000 ppm DEHP plus 10,000 ppm DnHP for 14 days. Rats receiving diets containing DEHP showed the expected increase in relative liver weight, in "peroxisomal" fatty acid oxidation and in CYP4A1. Serum triglyceride and serum cholesterol were also reduced, and the thyroid showed the histological changes mentioned above. Rats consuming diets containing DnHP showed no increase in relative liver weight and no induction of peroxisomal fatty acid oxidation or CYP4A1. However, there was a marked accumulation of fat in the liver. The fall in serum cholesterol was similar to that in rats treated with DEHP, but the fall of serum triglyceride was more pronounced. Thyroidal changes were again observed. In general, changes in rats treated with a mixture of DEHP and DnHP were very similar to those found with rats treated with DEHP alone. The liver was enlarged, and peroxisomal fatty acid oxidation and CYP4A1 were both induced. The amount of fat in the liver was much less than in rats receiving DnHP alone. Thyroid changes were similar to those in rats receiving the individual compounds. The effect on serum cholesterol seemed additive, but the levels of serum triglyceride were intermediate between the groups receiving the single compounds.
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)
EC50; Species: Daphnia magna (Water flea, age < or = 24 hr); Conditions: freshwater, static, 20 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: 180 ug/L for 48 hr; Effect: intoxication, immobilization /> or = 95% purity/
EC50; Species: Paratanytarsus parthenogeneticus (Midge, larvae 2-3 instar); Conditions: freshwater, static, 20 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: >130 ug/L for 96 hr; Effect: mortality /> or = 95% purity/
EC50; Species: Anodonta cygnea (Swan mussel, 2-3 instar); Conditions: freshwater, static, 22-24 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: 330 ug/L for 48 hr; Effect: decreased population abundance /> or = 95% purity/
LC50; Species: Cyprinodon variegatus (Sheepshead minnow, juvenile, length 6-17 mm); Conditions: freshwater, static, 22 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: 780 ug/L for 96 hr /> or = 95% purity/
For more Ecotoxicity Values (Complete) data for DIHEXYL PHTHALATE (8 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), an average Koc value of 5.26X10+5(2), indicates that dihexyl phthalate is expected to be immobile in soil(SRC). Volatilization of dihexyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-5 atm-cu m/mole(SRC) based upon its vapor pressure, 1.4X10-5 mm Hg(3), and water solubility, 0.05 mg/L(4). Dihexyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Biodegradation in soil may be important(SRC) based on a study using an acclimated inoculum of soil, sewage and activated sludge; >99% of dihexyl phthalate was lost and 77% of theoretical carbon dioxide was evolved after 28 days(5).
AQUATIC FATE: Based on a classification scheme(1), an average Koc value of 5.26X10+5(2), indicates that dihexyl 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 2.6X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 1.4X10-5 mm Hg(4), and water solubility, 0.05 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.8 and 26 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 15 years if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 1,100(SRC), from a log Kow of 6.82(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is very high(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(10). 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(11). In a river die-away test, it took 1 day to achieve 90% degradation(12). An initial concn of dihexyl phthalate of 25 mg/L was degraded 30 to 95% in fresh water after a 14 day incubation(10).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dihexyl phthalate, which has a vapor pressure of 1.4X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dihexyl 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 26 hours(SRC), calculated from its rate constant of 1.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dihexyl phthalate may be removed from the air by wet or dry deposition(SRC). Dihexyl phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
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)
/BIRDS and MAMMALS/ The effects of dihexyl phthalate (DHP) on weight and food consumption in captive starlings (Sturnus vulgaris) were studied. All phthalate fed starlings had greater lipid means in the carcass homogenates than controls ... Differences in food consumption existed only in groups fed 250 ppm (other groups given 25 ppm).
/AQUATIC SPECIES/ Tests were performed with the freshwater invertebrates Hyalella azteca, Chironomus tentans, and Lumbriculus variegatus to determine the acute toxicity of six phthalate esters, including dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), butylbenzyl phthalate (BBP), di-n-hexyl phthalate (DHP), and di-2-ethylhexyl phthalate (DEHP). It was possible to derive 10-d LC50 (lethal concentration for 50% of the population) values only for the four lower molecular weight esters (DMP, DEP, DBP, and BBP), for which toxicity increased with increasing octanol-water partition coefficient (Kow) and decreasing water solubility. ... No significant survival reductions were observed when the three species were exposed to either DHP or DEHP at concentrations approximating their water solubilities.
/AQUATIC SPECIES/ Seven phthalate esters /including di-n-hexyl phthalate (DHP) were evaluated for their 10-d toxicity to the freshwater invertebrates Hyalella azteca and Chironomus tentans in sediment. ... All seven esters were tested in a sediment containing 4.80% total organic carbon (TOC) ... The five higher molecular weight phthalate esters /including DHP which was tested/ .... and found to be nontoxic in water-only tests ... were tested at single concentrations between 2,100 and 3,200 mg/kg dry weight. Preliminary spiking studies were performed to assess phthalate ester stability under test conditions. The five higher molecular weight phthalate esters in sediment had no effect on survival or growth of either C. tentans or H. azteca, consistent with predictions based on water-only tests and EqP theory. ...
/AQUATIC SPECIES/ A previous in vitro study has indicated that four phthalate esters (PAEs) could damage hemocytes and decreases the cellular immunity of prawns ... . The aim of this study was to investigate the in vivo effect of ... diethyl phthalate (DEP), dihexyl phthalate (DHP), dipropyl phthalate (DPrP) and diphenyl phthalate (DPP) on the defense system of the giant freshwater prawn, M. rosenbergii. PAE dissolved in corn oil was continuously fed to prawns for 8 days and five immune parameters (total hemocyte count, THC; ratio of granulocytes to hyalinocytes, G/H; intrahemocytic total phenoloxidase activity, PO(T); intracellular superoxide anion (O2-) production; transglutaminase (TGase) activity) were separately detected on days 1, 4 and 8. In addition, mortality was determined on days 4 and 8 after challenging the prawns with Lactobacillus garvieae. ... DHP demonstrated the lowest toxicity in that it only influenced the PO activity and O2- production before 4 days after treatment and caused 6.6% mortality on day 8. DEP decreased G/H, PO(T) and TGase activity on day 1 and reduced THC, G/H and PO(T) and caused 16.6% mortality on day 4; however, on day 8, it increased O2- production and caused no mortality. In the DPrP-treated group, a reduction of all the immune reactions apart from TGase activity and 22.2% mortality were detected on day 4. ... DPP ... decreased all the immune parameters apart from THC on days 1 and 4, but caused no mortality on day 4; but on day 8, an increase of O2- production and 17.7% mortality were detected. These results indicated that the immune reactions of prawns were variable due to the different toxic effects of PAEs. In addition, ... on day 8 after treatment, ... DHP, DPrP and DPP increased O2- production and did not influence the other four reactions, but mortality was detected in these groups.
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=84-75-3][Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=84-75-3]
The average Koc of (14)C-dihexyl phthalate using three standard USEPA sediments (supplied and characterized by the EPA) was measured at 5.26X10+5(1). According to a classification scheme(2), this Koc value suggests that dihexyl phthalate is expected to be immobile in soil.
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, dihexyl ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.
A testing consent order is in effect for di-n-hexyl phthalate for environmental effects and chemical fate testing. FR citation: 1/9/89.
Dermally absorbed DnHP was widely distributed throughout the body with no tissue containing >0.6% of the applied dose. There was no evidence for accumulation in any tissue.
Used as plasticizer; Used to make plastisols for automobile parts and dip-molded products; [HSDB]
DnHP is used in the making of plastisols that are subsequently used in the manufacture of automobile parts (air filters, battery covers) and dip-molded products (tool handles, dishwasher baskets). Commercial phthalate substances containing DnHP may be added to the PVC utilized in the manufacture of flooring, canvas tarps, and notebook covers. Substances containing DnHP may also be used in traffic cones, toys, vinyl gloves, weather stripping, flea collars, shoes, and conveyor belts used in food packaging operations.
Plasticizer for cellulose ester and vinyl plastics.
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)
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4947]
This chemical is listed as an Extended High Production Volume (EHPV). Chemicals listed as EHPV were produced in or imported into the U.S. in >1 million pounds according to the 2002 Toxic Substances Control Act (TSCA) Inventory Update. The EHPV program is a voluntary initiative that allows companies to demonstrate that adequate screening data exist for organic HPV chemicals.
1,2-Benzenedicarboxylic acid, 1,2-dihexyl ester: ACTIVE
DnHP is often found as a minor component (less than 1%) of C6-10- phthalate mixtures; it may also be an isomer in mixtures of diisohexyl phthalates (DIHP) (CAS RN 68515-50-4) at levels of 25% or lower.
용도Di-n-hexyl Phthalate is a Phthalate derivative and an organic extract contaminant found in drinking water, which was shown to activate Nrf-2-Mediated Antioxidant response in human cell line.
일반 설명Yellow-brown oily viscous liquid with a slight aromatic odor. Insoluble in water.
생산 방법DnC6P is manufactured by esterifying phthalic anhydride and hexanol in the presence of sulfuric acid.
/AQUATIC SPECIES/ Five phthalate esters, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, and dioctyl phthalate, were tested for the hatching of brine shrimp (Artemia salina) eggs. Dibutyl phthlate ester was the most toxic of the phthalates tested. The toxic order of 3 of the esters was dibutyl phthalate greater than diethyl phthalate greater than dimethyl phthalate. Concentrations were 10, 20, and 50 ppm.