Di 2-ethylhexyl phthalate

Di(2-ethylhexyl)phthalate (DEHP) has been reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals (12). A detailed report is available (13). 

Historically, di(2-ethylhexyl) phthalate has constituted approximately 50% of all the phthalate ester plasticizers used. However, in recent years, the use of di(2-ethylhexyl) phthalate has diminished because of health concerns. It is no longer used in plastic food packaging or baby teethers and rattles. Many toy manufacturers have discontinued its use in toys, and it is being replaced by linear phthalates and other plasticizers (12). 

The primary routes of potential human exposure to di(2-ethylhex-yl) phthalate are inhalation, ingestion, dermal contact, and through medical procedures. A substantial fraction of the U.S. population is exposed to measurable levels of di(2-ethylhexyl) phthalate because of its widespread use in consumer products. A high-risk segment of the population consists of individuals receiving dialysis treatments or blood transfusions from sources that have contacted di(2-ethyl-hexyl) phthalate-containing tubing or containers. 

Workers in printing and painting occupations may also be exposed. Inhalation of aerosols or mists is the primary occupational exposure route. 

Di(2-ethylhexyl) phthalate is widely distributed in the environment and has been detected in soil samples, animal and human tissues, and various forms of fish and marine life. Disposal of plastic products containing di(2-ethylhexyl) phthalate is a major source of environmental concern. 

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See also Di(2-ethylhexyl) phthalate.) [PHTHALIC ACID AND OTTiERBENZENEPOLYCARBOXYLIC ACIDS] (Vol 18) Dioctyl sodium sulfosuccinate... 

Aldehydes fiad the most widespread use as chemical iatermediates. The production of acetaldehyde, propionaldehyde, and butyraldehyde as precursors of the corresponding alcohols and acids are examples. The aldehydes of low molecular weight are also condensed in an aldol reaction to form derivatives which are important intermediates for the plasticizer industry (see Plasticizers). As mentioned earlier, 2-ethylhexanol, produced from butyraldehyde, is used in the manufacture of di(2-ethylhexyl) phthalate [117-87-7]. Aldehydes are also used as intermediates for the manufacture of solvents (alcohols and ethers), resins, and dyes. Isobutyraldehyde is used as an intermediate for production of primary solvents and mbber antioxidants (see Antioxidaisits). Fatty aldehydes Cg—used in nearly all perfume types and aromas (see Perfumes). Polymers and copolymers of aldehydes exist and are of commercial significance. 

In the calendering method, a PVC compound which contains plasticizers (qv) (60—120 phr), pigments (qv) (0—10 phr), fillers (qv) (20—60 phr), stabilizers (10—30 phr), and other additives, is kneaded with calender roUs at 150—200°C, followed by extmsion between clearance-adjusted roUs for bonding onto the substrate. This method is employed for products with thick PVC layers, ie, of 0.05—0.75 mm thickness. The main plasticizer used is di-2-ethylhexyl phthalate (DOP). For filler to reduce cost, calcium carbonate is mainly used. A woven or knit fabric made of cotton, rayon, nylon, polyester, and their blend fiber is used as substrate. For foamed vinyl-coated fabrics, the bonded materials are heated in an oven to decompose the foam-blowing... 

Uses. Phthabc anhydride is used mainly in plasticizers, unsaturated polyesters, and alkyd resins (qv). PhthaUc plasticizers consume 54% of the phthahc anhydride in the United States (33). The plasticizers (qv) are used mainly with poly(vinyl chloride) to produce flexible sheet such as wallpaper and upholstery fabric from normally rigid polymers. The plasticizers are of two types diesters of the same monohydric alcohol such as dibutyl phthalate, or mixed esters of two monohydric alcohols. The largest-volume plasticizer is di(2-ethylhexyl) phthalate [117-81-7] which is known commercially as dioctyl phthalate (DOP) and is the base to which other plasticizers are compared. The important phthahc acid esters and thek physical properties are Hsted in Table 12. The demand for phthahc acid in plasticizers is naturally tied to the growth of the flexible poly(vinyl chloride) market which is large and has been growing steadily. 

Di-2-EthylhexylPhthalate. In Western Europe, di-2-ethylhexyl phthalate [117-81-7] (DEHP), also known as dioctyl phthalate (DOP), accounts for about 50% of all plasticizer usage and as such is generally considered as the industry standard. The reason for this is that it is in the mid-range of plasticizer properties. DEHP (or DOP) is the phthalate ester of 2-ethyIhexanol, which is normally manufactured by the dimerization of butyraldehyde (eq. 2), the butyraldehyde itself being synthesized from propylene (see Butyraldehydes). 

Numerous toxicological studies have been conducted on a variety of plasticizers. However, because di-(2-ethylhexyl) phthalate (DEHP) is the most widely used plasticizer and is a well-defined single substance, it is the plasticizer that has been most thoroughly investigated in terms of its toxicology and has often been considered as a model for the other phthalates (36). 

The majority (92% in 1988) of the butyraldehyde produced in the United States is converted into 1-butanol and 2-ethyIhexanol (2-EH). 2-EH is most widely used as the di(2-ethylhexyl) phthalate [117-81-7] ester for the plasticisation of flexible PVC. Other uses for 2-EH include production of intermediates for acryflc surface coatings, diesel fuel, and lube oil additives (24). 

The polarity of the polyethers makes them incompatible with hydrocarbon-type plasticizers, which tend to bleed. Effective plasticizers are ethers such as di(butoxyethoxyethyl)formal [143-29-3] (Thiokors TP-90B), esters such as di(2-ethylhexyl) phthalate [117-81-7] dioctyl phthalate (DOP), polyesters such as Paraplex G50 (Rohm and Haas), and ether—esters such as di(butoxyethoxyethyl) adipate [114-17-3] (Thiokol s TP-95). The lower mol wt plasticizers, DOP, TP-90B, and TP-95 improve vulcanizate low temperature performance. The polymeric plasticizers maintain higher temperature and long-term aging properties. Epoxidized plasticizers should be avoided because they interfere with vulcanization. 

The phthalate esters are one of the most widely used classes of organic esters, and fortunately they exhibit low toxicity (82). Because of the ubiquitous nature of phthalates, many iavestigations have been conducted to determine their toxicides to marine life as well as ia mammals (83—85). Generally, phthalates are not absorbed through the skin and are not very potent when inhaled. The phthalates become less toxic as the alcohol group increases in molecular weight. For example, dimethyl phthalate has an oral LD q (mouse) of 7.2 g/kg, whereas di(2-ethylhexyl) phthalate shows an oral LD q (rat) of greater than 26 g/kg. 

Di-(2-ethylhexyl)phthalate ( di-iso-octyl phthalate) [117-81-7] M 390.6, b 384°, 256-257°/lmni, d 0.9803, n 1.4863. Washed with Na2C03 soln, then shaken with water. After the resulting emulsion had been broken by adding ether, the ethereal soln was washed twice with water, dried (CaCl2), and evaporated. The residual liquid was distd several times under reduced pressure, then stored in a vacuum desiccator over P2O5 [French and Singer J Chem Soc 1424 1956]... 

Diethylene triamine Diethyl ether, see Ethyl ether Di(2-ethylhexyl)phthalate, see Di-sec-octyl phthalate Diethyl ketone Diethyl phthalate Diethyl sulphate Difluorodibromomethane Diglycidyl ether (DGE)... 

Chemical Designations - Synonyms. Bis(2-ethylhexyl) Phthalate Di(2-ethylhexyl) Phthalate DOP Octoil Phthalic Acid, Bis(2-ethylhexyl) Ester Chemical Formula-. o-C,jH4[COOCH2CH-(QHjXCHJ CHJj. 

Di(2-ethylhexyl) phthalate zero 0.006 Liver problems increased risk of cancer Discharge from rubber and chemical factories... 

Diethyl aniline, 54 Diethylcarbaniazine citrate, 54 Diethyl carbamyl chloride, 54 Diethyl chlorophosphate, 54 Diethylene triamine, 54 Diethyl ether, 54 Di(2-ethylhexyl) phthalate, 54 Diethyl ketone, 54 Diethyl-p-phenylenediamine, 54 Diethyl phthalate, 54 Diethylstilbestrol, 55 Diethyl sulfate, 55 Diethyl zinc, 55 Difluoromethane chloride, 55 Digitoxin, 55 Diglycidyl ether, 55 Digoxin, 55 Diisobutyl ketone, 55 Diisopropylamine, 55 Diisopropyl ether, 55 DIKAMIN , 2,4-D, 55 DIKONIRT , 2,4-D, 55 Dimefox, 55 Dimethoate, 55 3,3 -Dimethoxybenzidine, 55 n,n-Dimethylacetamide, 56 Dimethylamine, 56 4-Dimethylaminoazobenzene, 56 Dimethylaminoethanol, 56 n,n-Dimethyl aniline, 56 7,12-Dimethylbenz[a]anthracene, 56 3,3 -Dimethylbenzidine, 56... 

Ethyl-1-hexanol, used in the synthesis of di(2-ethylhexyl) phthalate plasticizer, is made commercially from bulanal. Show the likely synthesis route. 

Masses 149, 167, and 279 suggest dioctyl phthalate or di(2-ethylhexyl) phthalate. 

PVC closure seals for jars Di-(2-ethylhexyl) phthalate Di-iso-decyl phthalate Di-iso-octyl phthalate... 

Peakall, D.B. (1974). Effects of di-normal-butyl and di-2-ethylhexyl phthalate on eggs of ring doves. Bulletin of Environmental Contamination and Toxicology 12, 698-702. 

Narotsky MG, Weller EA, Chinchilli VM, et al. 1995. Nonadditive developmental toxicity in mixtures of trichloroethylene, di(2-ethylhexyl) phthalate, and heptachlor in a 5 x 5 x 5 design. Fund Appl Toxicol 27 203-216. 

Lake, B.G., Kozlen, S.L., Evans, J.G., Gray, T.J.B., Young, P.J. and Gangolli, S.D. (1987). Effect of prolonged administration of clofibric acid and di-(2-ethylhexyl)phthalate on hepatic enzyme activities and lipid peroxidation in the rat. Toxicology 44, 213-228. 

CaSt Calcium stearate DEHP Di(2-ethylhexyl)phthalate... 

DBP, di-n-butylphthalate DCHP, Dicyclohexylphthalate TCB, 1,2,4, trichlorobenzene DEHP, di-(2-ethylhexyl) phthalate... 

The following example is based on a risk assessment of di(2-ethylhexyl) phthalate (DEHP) performed by Arthur D. Little. The experimental dose-response data upon which the extrapolation is based are presented in Table II. DEHP was shown to produce a statistically significant increase in hepatocellular carcinoma when added to the diet of laboratory mice (14). Equivalent human doses were calculated using the methods described earlier, and the response was then extrapolated downward using each of the three models selected. The results of this extrapolation are shown in Table III for a range of human exposure levels from ten micrograms to one hundred milligrams per day. The risk is expressed as the number of excess lifetime cancers expected per million exposed population. 

National Toxicology Program. "Carcinogenesis Bioassay of di(2-ethylhexyl)-phthalate." (Draft Report) U.S. Dept, of Health and Human Services, DHAS Pub. No. 81-1773, 1980. 

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