Quick Search
Dioctyl phthalate has good heat stability, plasticized capacity, resistance to freeze, electrical properties and good UV filtering properties.
Dioctyl phthalate is not soluble in water but is soluble in oil and finds use as a solvent in glow sticks.
Dioctyl Phthalate is an organic compound and included in the class of phthalates which are used as plasticizers.
CAS Number: 117-81-7
EC Number: 204-211-0 617-060-4
Chemical Formula: C24H38O4
Molar Mass: 390.564 g·mol−1
Synonyms: Dioctyl phthalate, DI-N-OCTYL PHTHALATE, 117-84-0, dioctyl benzene-1,2-dicarboxylate, DNOP, Vinicizer 85, Dinopol NOP, n-Octyl phthalate, Phthalic acid, dioctyl ester, Phthalic acid di-n-octyl ester, Dioctyl 1,2-benzenedicarboxylate, Dioctyl o-benzenedicarboxylate, Bis(n-octyl) phthalate, 1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester, 1,2-Benzenedicarboxylic acid, dioctyl ester, RCRA waste number U107, di-octyl phthalate, Dioktylester kyseliny ftalove, NSC 15318, N-Dioctyl phthalate, CCRIS 6196, o-Benzenedicarboxylic acid, dioctyl ester, 1,2-Benzenedicarbonic acid, dioctyl ester, HSDB 1345, AI3-15071 (USDA), EINECS 204-214-7, 8031-29-6, Dioktylester kyseliny ftalove [Czech], RCRA waste no. U107, BRN 1915994, Benzenedicarboxylic acid di-n-octyl ester, UNII-8X3RJ0527W, DTXSID1021956, CHEBI:34679, 8X3RJ0527W, NSC-15318, NCGC00090781-02, DTXCID801956, Phthalic acid, bis-n-octyl ester, CAS-117-84-0, Di-n-octyl phthalate, analytical standard, Dioktylftalat, Diocyl phthalate, n-Dioctylphthalate, 1, dioctyl ester, Vinycizer 85, Phthalate, Dioctyl, di-n-octylphthalate, Dioctyl o-phthalate, Phthalic acid dioctyl, Dioctyl phthalate, n-, DOP (CHRIS Code), Dioctyl phthalate, n-;, Phtalate de dioctyle normal, Di-n-octylphthalate (DnOP), SCHEMBL23053, BIDD:ER0319, DnOP (Di-n-octyl phthalate), CHEMBL1409747, NSC15318, DI-N-OCTYL PHTHALATE [HSDB], Tox21_111020, Tox21_202233, Tox21_300549, Di-n-octyl phthalate, p.a., 99%, LS-594, MFCD00015292, STL280370, O-Benzenedicarboxylicacid Dioctylester, AKOS015889916, 1,2-dioctyl benzene-1,2-dicarboxylate, NCGC00090781-01, NCGC00090781-03, NCGC00090781-04, NCGC00090781-05, NCGC00254360-01, NCGC00259782-01, Di-n-octyl phthalate, >=98.0% (GC), FT-0655747, FT-0667608, P0304, EN300-40135, IS_DI-N-OCTYL PHTHALATE-3,4,5,6-D4, A803836, Q908490, J-003672, J-520376, F0001-0293, Z407875554, Di-n-octyl phthalate, certified reference material, TraceCERT(R), 4-[Bis(1-aziridinyl)phosphinyl]morpholine, 4-[Bis(1-aziridinyl)phosphoryl]morpholin [German] [ACD/IUPAC Name], 4-[Bis(1-aziridinyl)phosphoryl]morpholine [ACD/IUPAC Name], 4-[Bis(1-aziridinyl)phosphoryl]morpholine [French] [ACD/IUPAC Name], 545-82-4 [RN], Aziridine, 1,1'-(4-morpholinylphosphinylidene)bis-, Aziridine, 1,1'-(morpholinophosphinylidene)bis-, Bis(1-aziridinyl)morpholinophosphine oxide, Dioctyl phthalate [ACD/IUPAC Name], Morpholine, 4-[bis(1-aziridinyl)phosphinyl]- [ACD/Index Name], 4-(di(aziridin-1-yl)phosphoryl)morpholine, 4-[BIS(AZIRIDIN-1-YL)PHOSPHOROSO]MORPHOLINE, 4-[bis(aziridin-1-yl)phosphoryl]morpholine, Aziridine, 1, 1'-(4-morpholinylphosphinylidene)bis-, Lederle 7-7344, MEPA, Morpholine, 4-(bis(1-aziridinyl)phosphinyl)- (9CI), Morpholine, 4-[bis (1-aziridinyl)phosphinyl]-, N-(3-Oxapentamethylene)-N',N''-diethylenephosphoramide, N, N'-Diethylene-N''-(3-oxapentamethylene)phosphoramide, N,N'-Diethylene-N''-(3-oxapentamethylene)phosphoramide, ODEPA, Oxa DEPA, Phosphine oxide, bis (1-aziridinyl)morpholino-, Phosphine oxide, bis(1-aziridinyl)-4-morpholinyl-, Phosphine oxide, bis(1-aziridinyl)morpholino-, Phosphine oxide, bis(1-aziridinyl)morpholino- (8CI), Dioctyl phthalate, DI-N-OCTYL PHTHALATE, 117-84-0, dioctyl benzene-1,2-dicarboxylate, Dinopol NOP, n-Octyl phthalate, Vinicizer 85, DNOP, Phthalic acid, dioctyl ester, Polycizer 162, Phthalic acid di-n-octyl ester, Dioctyl 1,2-benzenedicarboxylate, Dioctyl o-benzenedicarboxylate, 1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester, 1,2-Benzenedicarboxylic acid, dioctyl ester, Bis(n-octyl) phthalate, Dioktylester kyseliny ftalove, NSC 15318, UNII-8X3RJ0527W, 1,2-Benzenedicarbonic acid, dioctyl ester, CHEBI:34679, 8X3RJ0527W, MFCD00015292, 68515-43-5, NCGC00090781-02, DSSTox_CID_1956, DSSTox_RID_76425, DSSTox_GSID_21956, 8031-29-6, octyl 2-(octyloxycarbonyl)benzoate, di-octyl phthalate, CAS-117-84-0, Di-n-octyl phthalate, analytical standard, CCRIS 6196, HSDB 1345, AI3-15071 (USDA), EINECS 204-214-7, Dioktylester kyseliny ftalove [Czech], RCRA waste no. U107, BRN 1915994, Benzenedicarboxylic acid di-n-octyl ester, 1, dioctyl ester, Vinycizer 85, di-n-octylphthalate, Dioctyl o-phthalate, Phthalic acid dioctyl, Phthalic acid, bis-n-octyl ester, 0014AD, ANW-17052, Di-n-octyl phthalate, p.a., 99%, NSC-15318, SBB008723, STL280370, AKOS015889916, MCULE-5138747558, 1,2-dioctyl benzene-1,2-dicarboxylate, Di-n-octyl phthalate, >=98.0% (GC), LS-15074, FT-0655747, FT-0667608, P0304, ST50826905, C14227, 1,2-BENZENEDICARBOXYLIC ACID DIOCTYL ESTER, Di-n-octyl phthalate, certified reference material, TraceCERT(R)
Dioctyl phthalate is an organic compound with the formula C6H4(CO2C8H17)2.
Dioctyl phthalate is the most common member of the class of phthalates, which are used as plasticizers.
Dioctyl phthalate is the diester of phthalic acid and the branched-chain 2-ethylhexanol.
This colorless viscous liquid is soluble in oil, but not in water.
Dioctyl phthalate has good heat stability, plasticized capacity, resistance to freeze, electrical properties and good UV filtering properties.
Dioctyl phthalate is used in PVC, PE, cellulose, film, artificial leather, cable, pipe material, sheet material, mold plastic and rubber.
Dioctyl phthalate is a non-volatile solvent mainly used as a plasticizer for polymers such as polyvinyl chloride (PVC), polystyrene (PS) and polyisoprene (PI).
Dioctyl phthalate is a combustible non-toxic colorless oily liquid with slight odor.
Dioctyl Phthalate is an organic compound and included in the class of phthalates which are used as plasticizers.
Dioctyl phthalate is a colorless liquid and the diester of phthalic acid.
Dioctyl phthalate is not soluble in water but is soluble in oil and finds use as a solvent in glow sticks.
Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.
Dioctyl phthalate is a diester of phthalic acid.
Dioctyl Phthalate is a low cost, general use plasticizer, which can be useful in hydraulic fluid applications and as a dielectric fluid in capacitors.
Dioctyl phthalate is still widely used as a plasticizer in selected applications where volatiles are less of an issue.
Dioctyl phthalate is also used as a hydraulic fluid and as a dielectric fluid in capacitors.
Dioctyl phthalate was the most widely used material as a plasticizer in manufacturing of articles made of PVC.
Due to toxicity reasons, Dioctyl phthalate usage has dropped and has been replaced by lower volatile phthalate and phthalate free products in some PVC and other applications
Dioctyl phthalate, also known as dioctyl 1,2-benzenedicarboxylate or DEHP, is a member of the class of compounds known as benzoic acid esters.
Benzoic acid esters are ester derivatives of benzoic acid.
Dioctyl phthalate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on Dioctyl phthalate pKa).
Dioctyl phthalate can be found in kohlrabi, which makes di(n-octyl) phthalate a potential biomarker for the consumption of this food product.
Dioctyl phthalate is a non-carcinogenic (not listed by IARC) potentially toxic compound.
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) (T3DB).
Dioctyl phthalate is a clear, colourless liquid which is slightly more dense than water with a slight but characteristic odour.
Dioctyl phthalate is miscible with most organic solvents but not soluble in water.
Dioctyl phthalate has several advantages over some other plasticizers in that Dioctyl phthalate is more economical.
Dioctyl phthalate provides the desired changes to physical and mechanical properties without causing changes to the chemical structure of the polymer.
Dioctyl phthalate jellifies quickly; in lacquer applications Dioctyl phthalate serves to eliminate cracks, increase resistance and provide a smooth surface.
Dioctyl phthalate is often used as a general purpose plasticizer.
Dioctyl phthalate is highly cost effective and also widely available.
Dioctyl phthalate broad range of characteristics such as high plasticizing efficiency, low volatility, UV-resistance, water-extracting proof, cold-resisting property, softness and electric property makes Dioctyl phthalate suitable for making a wide range of products.
Dioctyl phthalate is used in the production of synthetic rubber, as a softening agent to make the synthetic rubber easier to rebound and harder to undergo form change under pressure.
Dioctyl phthalate is widely used in PVC and ethyl cellulose resins to make plastic film, imitation leather, electric wire, etc.
Dioctyl phthalate, also known as diethylhexyl phthalate, is an organic compound with the molecular formula C6H4 (CO2C8H17).
Dioctyl phthalate, characterized by Dioctyl phthalate molecular weight, high boiling point, and low vapor pressure, is one of the most widely used general emollients.
Dioctyl phthalate is synthesized by the reaction of phthalic anhydride with an chemical alcohol such as 2-ethyl hexanol.
Dioctyl phthalate is a softener used in the production of flexible polyvinyl chloride (PVC) plastics.
Dioctyl phthalate is insoluble in water and has good stability against heat, ultraviolet light, wide compatibility, and has excellent resistance to hydrolysis.
Dioctyl phthalate is a colorless, odorless, oily liquid that doesn't evaporate easily.
Dioctyl phthalate is a man-made substance used to keep plastics soft or more flexible.
This type of plastic can be used for medical tubing and blood storage bags, wire and cables, carpetback coating, floor tile, and adhesives.
Dioctyl phthalate is also used in cosmetics and pesticides.
Dioctyl phthalate appears as a clear liquid with a mild odor.
Slightly less dense than water and insoluble in water.
The primary hazard is the threat to the environment.
Immediate steps should be taken to limit Dioctyl phthalate spread to the environment.
As a liquid, can easily penetrate the soil and contaminate groundwater and nearby streams.
Eye contact may produce severe irritation and direct skin contact may produce mild irritation.
Dioctyl phthalate is used in the manufacture of a variety of plastics and coating products.
Dioctyl phthalate is a phthalate ester and a diester.
Applications of Dioctyl phthalate:
Dioctyl phthalate is a phthalate ester which is used in the manufacture of a wide range of plastics and coating products.
Dioctyl phthalate is used as a plasticizer in PVC paste and pulp mixtures and as an additive in many other processes.
Dioctyl phthalate can be found in many end products including PVC soles for shoes and slippers, synthetic leather, waterproof membranes, paints, varnishes, floor coverings, door mats and hoses.
Dioctyl phthalate is also used in the calendaring process of paper finishing, to produce PVC granules, as a hydraulic or dielectric fluid in capacitors, in toxicology studies and in risk assessment studies on food contamination which occurs via migration of phthalates into foodstuffs from food-contact materials (FCM).
Dioctyl Phthalate is a plasticizer used in the production of flexible polyvinyl chloride (PVC) plastic.
Dioctyl Phthalate is one of the most widely used plasticizers in PVC due to Dioctyl phthalate low cost.
Dioctyl phthalate is a general-purpose plasticizer and long-time industry standard known for Dioctyl phthalate good stability to heat and ultraviolet light, and broad range of compatibility for use with PVC resins.
Dioctyl Phthalate can also be used as dielectric and hydraulic fluids.
Dioctyl phthalate is also a solvent for many chemicals, such as in glowsticks.
Dioctyl phthalate is a non-volatile solvent mainly used as a plasticizer for polymers such as polyvinyl chloride (PVC), polystyrene (PS) and polyisoprene (PI).
Plasticizers for:
Cables and wires.
Building and construction for cladding and roof membranes.
PVC pipes and flooring.
Others such as hoses, shoe soles sealings industrial doors, swimming pool covers, shower curtains, roofing materials, water beds, furniture and disposable gloves.
Plastic Industry:
Plasticizers:
Dioctyl phthalate can be used as a softening agent, such as to make Dioctyl phthalate easier to rebound and harder to undergo form change under pressure, without affecting of the plastics.
Dioctyl phthalate possesses Dioctyl phthalate good plasticizing properties thanks to the ability to make the long polimers molecules to slide against one another.
Dioctyl phthalate is extensively used in processing polyvinyl choride and ethylcellulose resins to produce plastic film, imitation leather, electric wire, cable wearer, sheet, planet, mould plastic products and used in nitrocellulose paints.
Dioctyl phthalate has the applications in the industry of automotive, building and construction material, flooring, medical device.
Wood Coating:
Dioctyl phthalate is used in the industrial wood coating to enhance the performance properties of the wood coatings formulations.
Medical Devices:
Dioctyl phthalate is used a plasticiser in the manufacture of medical and sanitary products, such as blood bags and dialysis equipment.
Dioctyl phthalate has a further and unique role in blood bags because Dioctyl phthalate actually helps to prolong the life of the blood itself.
Dioctyl phthalate also stabilises the membranes of red blood cells enabling blood product storage in PVC blood bags for several weeks.
Plastics may contain from 1% to 40% of Dioctyl phthalate.
Uses of Dioctyl phthalate:
Dioctyl phthalate is used as a plasticizer and dye carrier for film, wire, cables, and adhesives.
Dioctyl phthalate is used as a plasticizer in carpet backing, packaging films, medical tubing, blood storage bags, floor tile, wire, cables, and adhesives.
Dioctyl phthalate is also used in cosmetics and pesticides.
There are no known commercial uses for pure DnOP.
However, DnOP constitutes approximately 20% of C6-10 phthalate substance.
Dioctyl phthalate is used in PVC utilized in the manufacture of flooring and carpet tile, canvas tarps, swimming pool liners, notebook covers, traffic cones, toys, vinyl gloves, garden hoses, weather stripping, flea collars, and shoes.
DnOP-containing phthalate substances are also used in PVC intended for food applications such as seam cements, bottle cap liners, and conveyor belts.
Dioctyl phthalate is principally used as a plasticizer in the production of plastics and PVC resins.
When used as a plasticizer, Dioctyl phthalate can represent 5-60% of the total weight of the plastics and resins.
Dioctyl phthalate increases flexibility and enhances or alters the properties of Dioctyl phthalate.
Dioctyl phthalate is also used for cellulose ester and polystyrene resins, as a dye carrier in plastic production (primarily PVC), and as a chemical intermediate in the manufacture of adhesives, plastisols, and nitrocellulose lacquer coatings.
Dioctyl phthalate also serves as a carrier for catalysts or initiators and as a substitute for electrical capacitor fluid.
Dioctyl phthalate is monomeric plasticizer for vinyl and cellulosic resins.
Due to Dioctyl phthalate suitable properties and the low cost, Dioctyl phthalate is widely used as a plasticizer in manufacturing of articles made of PVC.
Plastics may contain 1% to 40% of Dioctyl phthalate.
Dioctyl phthalate is also used as a hydraulic fluid and as a dielectric fluid in capacitors.
Dioctyl phthalate also finds use as a solvent in glowsticks.
Approximately three million tonnes are produced and used annually worldwide.
Manufacturers of flexible PVC articles can choose among several alternative plasticizers offering similar technical properties as Dioctyl phthalate.
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.
Industrial Processes with risk of exposure:
Working with Glues and Adhesives
Textiles (Printing, Dyeing, or Finishing)
Environmental exposure of Dioctyl phthalate:
Dioctyl phthalate 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.
Dioctyl phthalate is an indoor air pollutant in homes and schools.
Common exposures come from the use of Dioctyl phthalate as a fragrance carrier in cosmetics, personal care products, laundry detergents, colognes, scented candles, and air fresheners.
The most common exposure to Dioctyl phthalate comes through food with an average consumption of 0.25 milligrams per day.
Dioctyl phthalate can also leach into a liquid that comes in contact with the plastic.
Dioctyl phthalate extracts faster into nonpolar solvents (e.g. oils and fats in foods packed in PVC).
Fatty foods that are packaged in plastics that contain Dioctyl phthalate are more likely to have higher concentrations such as milk products, fish or seafood, and oils.
The US FDA therefore permits use of Dioctyl phthalate-containing packaging only for foods that primarily contain water.
Dioctyl phthalate can leach into drinking water from discharges from rubber and chemical factories; The US EPA limits for Dioctyl phthalate in drinking water is 6 ppb.
Dioctyl phthalate is also commonly found in bottled water, but unlike tap water, the EPA does not regulate levels in bottled water.
Dioctyl phthalate 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 Dioctyl phthalate in some European cheeses and creams were even higher, up to 200,000 ppb, in 1994.
Additionally, workers in factories that utilize Dioctyl phthalate in production experience greater exposure.
The U.S. agency OSHA's limit for occupational exposure is 5 mg/m3 of air.
Use in medical devices of Dioctyl phthalate:
Dioctyl phthalate 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.
Dioctyl phthalate 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 Dioctyl phthalate 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 Dioctyl phthalate 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 Dioctyl phthalate into patients and, instead, to resort to Dioctyl phthalate-free alternatives.
In July 2002, the U.S. FDA issued a Public Health Notification on Dioctyl phthalate, 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-Dioctyl phthalate 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 Dioctyl phthalate leaching out of these devices.
Although more research is needed to develop alternatives to Dioctyl phthalate 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 Dioctyl phthalate then a Dioctyl phthalate alternative should be considered if medically safe.
Metabolism of Dioctyl phthalate:
Dioctyl phthalate hydrolyzes to mono-ethylhexyl phthalate (MEHP) and subsequently to phthalate salts.
The released alcohol is susceptible to oxidation to the aldehyde and carboxylic acid.
Manufacturing process of Dioctyl phthalate:
All manufacturers of phthalate esters use the same processes.
Dioctyl phthalate is manufactured by phthalic sterilization of anhydride with 2-ethyl-hexanol.
This reaction occurs in two successive stages. The first stage of the reaction leads to the formation of a monoester by the de-alcoholization of phthalic acid, this step is completed quickly.
The second step of the production of dioctyl phthalate involves converting the monoster to a diester.
This is a reversible reaction and proceeds more slowly than the first reaction.
To change the equilibrium towards the diester, the reaction water is removed by distillation.
High temperatures and catalysts accelerate the reaction rate.
Depending on the catalyst used, the temperature in the second stage varies from 140°C to 165°C with acidic catalysts and from 200°C to 250°C with amphoteric catalysts.
Purity changes may occur depending on the catalyst, the reacting alcohol, and the type of process.
Excess alcohol is recovered and the Iran dioctyl phthalate is purified by vacuum distillation.
The reaction sequence is performed in a closed system.
This process can be performed sequentially or in batches.
Manufacturing Methods of Dioctyl phthalate:
Dioctyl phthalate is produced commercially as a component of mixed phthalate esters, including straight- chain C6, C8, and Cl0 phthalates.
Dioctyl phthalate is produced at atmospheric pressure or in a vacuum by heating an excess of n-octanol with phthalic anhydride in the presence of an esterification catalyst such as sulfuric acid or p-toluenesulfonic acid.
The process may be either continuous or discontinuous.
Dioctyl phthalate can also be produced by the reaction of n-octylbromide with phthalic anhydride.
Dioctyl phthalate is formed via the esterification of n-octanol with phthalic anhydride in the presence of a catalyst (sulfuric acid or p-toluenesulfonic acid) or noncatalytically at high temperature.
Pharmacology and Biochemistry of Dioctyl phthalate:
MeSH Pharmacological Classification:
Plasticizers:
Materials incorporated mechanically in plastics (usually PVC) to increase flexibility, workability or distensibility; due to the non-chemical inclusion, plasticizers leach out from the plastic and are found in body fluids and the general environment.
Identification of Dioctyl phthalate:
Analytic Laboratory Methods:
Method: DOE OM100R
Procedure: gas chromatography with mass spectrometer ion trap detector
Analyte: Dioctyl phthalate
Matrix: solid waste matrices, soils, and groundwater
Detection Limit: 160 ug/L.
Method: EPA-EAD 1625
Procedure: gas chromatography/mass spectrometry
Analyte: Dioctyl phthalate
Matrix: water
Detection Limit: 10 ug/L.
Method: EPA-EAD 606
Procedure: gas chromatography with electron capture detector
Analyte: Dioctyl phthalate
Matrix: wastewater and other waters
Detection Limit: 3 ug/L.
Method: EPA-NERL 506
Procedure: gas chromatography with photoionization detection
Analyte: Dioctyl phthalate
Matrix: drinking water
Detection Limit: 6.42 ug/L.
Production of Dioctyl phthalate:
Dioctyl phthalate is produced commercially by the reaction of excess 2-ethylhexanol with phthalic anhydride in the presence of an acid catalyst such as sulfuric acid or para-toluenesulfonic acid.
Dioctyl phthalate was first produced in commercial quantities in Japan circa 1933 and in the United States in 1939.
Dioctyl phthalate has two stereocenters, located at the carbon atoms carrying the ethyl groups.
As a result, has three distinct stereoisomers, consisting of an (R,R) form, an (S,S) form (diastereomers), and a meso (R, S) form.
As most 2-ethylhexanol is produced as a racemic mixture, commercially-produced Dioctyl phthalate is therefore almost always racemic as well, and consists of equal amounts of all three stereoisomers.
Properties of Dioctyl phthalate:
Dioctyl phthalate, is clear, colourless, viscous liquid with a slight, characteristic odor.
Soluble in ethanol, ether, mineral oil and the majority of organic solvents.
Immiscible with water, resistant to hydrolysis and air oxygen activity.
Dioctyl phthalate high plasticizing efficiency, fusion rate, visosity, low volatility, UV-resisting property, water-extracting proof, cold-resisting property, and also good softness and electric property found a lot of applications in many offshoots of the industry.
Effects on living organisms of Dioctyl phthalate:
Endocrine disruption:
Dioctyl phthalate, along with other phthalates, is believed to cause endocrine disruption in males, through Dioctyl phthalate action as an androgen antagonist, and may have lasting effects on reproductive function, for both childhood and adult exposures.
Prenatal phthalate exposure has been shown to be associated with lower levels of reproductive function in adolescent males.
In another study, airborne concentrations of Dioctyl phthalate at a PVC pellet plant were significantly associated with a reduction in sperm motility and chromatin DNA integrity.
Additionally, the authors noted the daily intake estimates for Dioctyl phthalate were comparable to the general population, indicating a "high percentage of men are exposed to levels of Dioctyl phthalate that may affect sperm motility and chromatin DNA integrity".
The claims have received support by a study using dogs as a "sentinel species to approximate human exposure to a selection of chemical mixtures present in the environment".
The authors analyzed the concentration of Dioctyl phthalate and other common chemicals such as PCBs in testes from dogs from five different world regions.
The results showed that regional differences in concentration of the chemicals are reflected in dog testes and that pathologies such as tubule atrophy and germ cells were more prevalent in testes of dogs proveining from regions with higher concentrations.
Development:
Dioctyl phthalate exposure during pregnancy has been shown to disrupt placental growth and development in mice, resulting in higher rates of low birthweight, premature birth, and fetal loss.
In a separate study, exposure of neonatal mice to Dioctyl phthalate through lactation caused hypertrophy of the adrenal glands and higher levels of anxiety during puberty.
In another study, pubertal administration of higher-dose Dioctyl phthalate delayed puberty in rats, reduced testosterone production, and inhibited androgen-dependent development; low doses showed no effect.
Government and industry response of Dioctyl phthalate:
Taiwan:
In October 2009, Consumers' Foundation, Taiwan (CFCT) published test results that found 5 out of the sampled 12 shoes contained over 0.1% of phthalate plasticizer content, including Dioctyl phthalate, which exceeds the government's Toy Safety Standard (CNS 4797).
CFCT recommend that users should first wear socks to avoid direct skin contact.
In May 2011, the illegal use of the plasticizer Dioctyl phthalate in clouding agents for use in food and beverages has been reported in Taiwan.
An inspection of products initially discovered the presence of plasticizers.
As more products were tested, inspectors found more manufacturers using Dioctyl phthalate and DINP.
The Department of Health confirmed that contaminated food and beverages had been exported to other countries and regions, which reveals the widespread prevalence of toxic plasticizers.
European Union:
Concerns about chemicals ingested by children when chewing plastic toys prompted the European Commission to order a temporary ban on phthalates in 1999, the decision of which is based on an opinion by the Commission's Scientific Committee on Toxicity, Ecotoxicity and the Environment (CSTEE).
A proposal to make the ban permanent was tabled.
Until 2004, EU banned the use of Dioctyl phthalate along with several other phthalates (DBP, BBP, DINP, DIDP and DNOP) in toys for young children.
In 2005, the Council and the Parliament compromised to propose a ban on three types of phthalates (DINP, DIDP, and DNOP) "in toys and childcare articles which can be placed in the mouth by children".
Therefore, more products than initially planned will thus be affected by the directive.
In 2008, six substances were considered to be of very high concern (SVHCs) and added to the Candidate List including musk xylene, MDA, HBCDD, DEHP, BBP, and DBP.
In 2011, those six substances have been listed for Authorization in Annex XIV of REACH by Regulation (EU) No 143/2011.
According to the regulation, phthalates including DEHP, BBP and DBP will be banned from February 2015.
In 2012, Danish Environment Minister Ida Auken announced the ban of DEHP, DBP, DIBP and BBP, pushing Denmark ahead of the European Union which has already started a process of phasing out phthalates.
However, Dioctyl phthalate was postponed by two years and would take effect in 2015 and not in December 2013, which was the initial plan.
The reason is that the four phthalates are far more common than expected and that producers cannot phase out phthalates as fast as the Ministry of Environment requested.
In 2012, France became the first country in the EU to ban the use of Dioctyl phthalate in pediatrics, neonatal, and maternity wards in hospitals.
Dioctyl phthalate has now been classified as a Category 1B reprotoxin, and is now on the Annex XIV of the European Union's REACH legislation.
Dioctyl phthalate has been phased out in Europe under REACH and can only be used in specific cases if an authorization has been granted.
Authorizations are granted by the European Commission, after obtaining the opinion of the Committee for Risk Assessment (RAC) and the Committee for Socio-economic Analysis (SEAC) of the European Chemicals Agency (ECHA).
California:
Dioctyl phthalate is classified as a "chemical known to the State of California to cause cancer and birth defects or other reproductive harm" (in this case, both) under the terms of Proposition 65.
Handling and storage of Dioctyl phthalate:
Precautions for safe handling:
Work under hood.
Do not inhale substance/mixture.
Avoid generation of vapours/aerosols.
Hygiene measures:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with substance.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Tightly closed.
Keep in a well-ventilated place.
Keep locked up or in an area accessible only to qualified or authorized persons.
Storage class:
Storage class (TRGS 510): 6.1C: Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
Storage of Dioctyl phthalate:
Dioctyl phthalate should be stored in tightly-closed containers in a cool, dry, well-ventilated place.
Dioctyl phthalate should be handled in accordance with good industry safety and hygiene practices.
Relevant engineering controls should be implemented.
Dioctyl phthalate may cause skin irritation if contact is repeated or prolonged, as well as severe eye irritation.
Risks from inhalation of vapour are minimal at room temperature but may cause irritation at higher temperatures.
Personal protective equipment including approved safety glasses, impervious clothing and gloves must be worn, and respirators should be worn where deemed necessary by risk assessments for the task being carried out.
Stability and reactivity of Dioctyl phthalate:
Reactivity:
Forms explosive mixtures with air on intense heating.
A range from approx. 15 Kelvin below the flash point is to be rated as critical.
Chemical stability
Dioctyl phthalate is chemically stable under standard ambient conditions (room temperature).
Conditions to avoid
Strong heating.
Incompatible materials:
Strong oxidizing agents
First aid measures of Dioctyl phthalate:
General advice:
Show Dioctyl phthalate safety data sheet to the doctor in attendance.
If inhaled:
After inhalation:
Fresh air.
Call in physician.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Consult a physician.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
Firefighting measures of Dioctyl phthalate:
Suitable extinguishing media:
Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For Dioctyl phthalate no limitations of extinguishing agents are given.
Special hazards arising from Dioctyl phthalate:
Carbon oxides
Combustible.
Vapors are heavier than air and may spread along floors.
Forms explosive mixtures with air on intense heating.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental release measures of Dioctyl phthalate:
Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel:
Do not breathe vapors, aerosols.
Avoid substance contact.
Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up carefully with liquid-absorbent material.
Dispose of properly.
Clean up affected area.
Identifiers of Dioctyl phthalate:
CAS Number: 117-81-7
ChEBI: CHEBI:17747
ChEMBL: ChEMBL402794
ChemSpider: 21106505
ECHA InfoCard: 100.003.829
EC Number: 204-211-0 617-060-4
KEGG: C03690
PubChem CID: 8343
RTECS number: TI0350000
UNII: C42K0PH13C
CompTox Dashboard (EPA): DTXSID5020607
InChI: InChI=1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3
Key: BJQHLKABXJIVAM-UHFFFAOYSA-N
SMILES: O=C(OCC(CC)CCCC)C1=CC=CC=C1C(OCC(CC)CCCC)=O
Synonym(s): Bis(2-ethylhexyl) phthalate, DEHP, DOP, Phthalic acid bis(2-ethylhexyl ester)
Linear Formula: C6H4-1,2-[CO2CH2CH(C2H5)(CH2)3CH3]2
CAS Number: 117-81-7
Molecular Weight: 390.56
Beilstein: 1890696
EC Number: 204-211-0
MDL number: MFCD00009493
PubChem Substance ID: 24893594
NACRES: NA.22
Properties of Dioctyl phthalate:
Chemical formula: C24H38O4
Molar mass: 390.564 g·mol−1
Appearance: Colorless, oily liquid
Density: 0.99 g/mL (20°C)
Melting point: −50 °C (−58 °F; 223 K)
Boiling point: 385 °C (725 °F; 658 K)
Solubility in water: 0.00003% (23.8 °C)
Vapor pressure: < 0.01 mmHg (20 °C)
Refractive index (nD): 1.4870
vapor density: >16 (vs air)
Quality Level: 200
vapor pressure: 1.2 mmHg ( 93 °C)
Assay: ≥99.5%
form: oil
autoignition temp.: 734 °F
impurities: ≤0.05% water (Karl Fischer)
color: APHA: ≤10
refractive index:
n25/D 1.483-1.487
n20/D 1.486 (lit.)
bp: 384 °C (lit.)
mp: −50 °C (lit.)
density:
0.985-0.987 g/mL at 20 °C
0.985 g/mL at 25 °C (lit.)
suitability: suitable for acidity (<=0.003%as phthalic acid)
SMILES string: CCCCC(CC)COC(=O)c1ccccc1C(=O)OCC(CC)CCCC
InChI: 1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3
InChI key: BJQHLKABXJIVAM-UHFFFAOYSA-N
Molecular Weight: 390.6 g/mol
XLogP3: 9.1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 18
Exact Mass: 390.27700969 g/mol
Monoisotopic Mass: 390.27700969 g/mol
Topological Polar Surface Area: 52.6Ų
Heavy Atom Count: 28
Complexity: 369
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Names of Dioctyl phthalate:
Regulatory process names:
Di-n-octyl phthalate (DNOP)
Dioctyl phthalate
Dioctyl phthalate
dioctyl phthalate
IUPAC names:
1,2-dioctyl benzene-1,2-dicarboxylate
Di-n-octyl Phthalate
dioctyl benzene-1,2-dicarboxylate
dioctyl phtalate
DIOCTYL PHTHALATE
Dioctyl phthalate
dioctyl phthalate
Preferred IUPAC name:
Bis(2-ethylhexyl) benzene-1,2-dicarboxylate
Other names:
Bis(2-ethylhexyl) phthalate
Di-sec octyl phthalate (archaic)
DEHP
Isooctyl phthalate, di-
DNOP
Other identifiers:
117-84-0
27214-90-0
8031-29-6
