Bis(2-ethylhexyl) phthalate

Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, DEHP; dioctyl phthalate, DOP) is an organic compound with the formula C6H4(CO2C8H17)2. DEHP is the most common member of the class of phthalates, which are used as plasticizers. It is the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colorless viscous liquid is soluble in oil, but not in water. Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, DEHP; dioctyl phthalate, DOP) is an organic compound with the formula C6H4(CO2C8H17)2. DEHP is the most common member of the class of phthalates, which are used as plasticizers. It is the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colorless viscous liquid is soluble in oil, but not in water. Due to its suitable properties and the low cost, DEHP is widely used as a plasticizer in manufacturing of articles made of PVC. Plastics may contain 1% to 40% of DEHP. It is also used as a hydraulic fluid and as a dielectric fluid in capacitors. DEHP also finds use as a solvent in glowsticks. Approximately three billion kilograms are produced annually worldwide. Industrial production entails the reaction of phthalic anhydride with 2-ethylhexanol: 2-Ethylhexanol is chiral, and the resultant DEHP consists of a mixture of (R,R)-, (S,S)-, and (R,S)-isomers (left). Manufacturers of flexible PVC articles can choose among several alternative plasticizers offering similar technical properties as DEHP. These alternatives include other phthalates such as diisononyl phthalate (DINP), di-2-propyl heptyl phthalate (DPHP), diisodecyl phthalate (DIDP), and non-phthalates such as 1,2-cyclohexane dicarboxylic acid diisononyl ester (DINCH), dioctyl terephthalate (DOTP), and citrate esters. DEHP is a component of many household items, including tablecloths, floor tiles, shower curtains, garden hoses, rainwear, dolls, toys, shoes, medical tubing, furniture upholstery, and swimming pool liners. DEHP is an indoor air pollutant in homes and schools. Common exposures come from the use of DEHP as a fragrance carrier in cosmetics, personal care products, laundry detergents, colognes, scented candles, and air fresheners.The most common exposure to DEHP comes through food with an average consumption of 0.25 milligrams per day. It can also leach into a liquid that comes in contact with the plastic; it extracts faster into nonpolar solvents (e.g. oils and fats in foods packed in PVC). Fatty foods that are packaged in plastics that contain DEHP are more likely to have higher concentrations such as milk products, fish or seafood, and oils. Food and Drug Administration (FDA) therefore permits use of DEHP-containing packaging only for foods that primarily contain water. DEHP can leach into drinking water from discharges from rubber and chemical factories; The US EPA limits for DEHP in drinking water is 6 ppb. It is also commonly found in bottled water, but unlike tap water, the EPA does not regulate levels in bottled water. DEHP levels in some European samples of milk, were found at 2000 times higher than the EPA Safe Drinking Water limits (12,000 ppb). Levels of DEHP in some European cheeses and creams were even higher, up to 200,000 ppb, in 1994. Additionally, workers in factories that utilize DEHP in production experience greater exposure. The U.S. agency OSHA's limit for occupational exposure is 5 mg/m3 of air. DEHP is the most common phthalate plasticizer in medical devices such as intravenous tubing and bags, IV catheters, nasogastric tubes, dialysis bags and tubing, blood bags and transfusion tubing, and air tubes. DEHP makes these plastics softer and more flexible and was first introduced in the 1940s in blood bags. For this reason, concern has been expressed about leachates of DEHP transported into the patient, especially for those requiring extensive infusions or those who are at the highest risk of developmental abnormalities, e.g. newborns in intensive care nursery settings, hemophiliacs, kidney dialysis patients, neonates, premature babies, lactating, and pregnant women. According to the European Commission Scientific Committee on Health and Environmental Risks (SCHER), exposure to DEHP may exceed the tolerable daily intake in some specific population groups, namely people exposed through medical procedures such as kidney dialysis. The American Academy of Pediatrics has advocated not to use medical devices that can leach DEHP into patients and, instead, to resort to DEHP-free alternatives. In July 2002, the U.S. FDA issued a Public Health Notification on DEHP, stating in part, 'We recommend considering such alternatives when these high-risk procedures are to be performed on male neonates, pregnant women who are carrying male fetuses, and peripubertal males' noting that the alternatives were to look for non-DEHP exposure solutions; they mention a database of alternatives. The CBC documentary The Disappearing Male raised concerns about sexual development in male fetal development, miscarriage), and as a cause of dramatically lower sperm counts in men. A review article in 2010 in the Journal of Transfusion Medicine showed a consensus that the benefits of a lifesaving treatments with these devices far outweigh the risks of DEHP leaching out of these devices. Although more research is needed to develop alternatives to DEHP that gives the same benefits of being soft and flexible which are required for most medical procedures. If a procedure requires one of these devices and if patient is at high risk to suffer from DEHP then a DEHP alternative should be considered if medically safe.