phthalates
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Phthalates ( ), or phthalate esters, are
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s of phthalic acid. They are mainly used as plasticizers, i.e., substances added to
plastic Plastics are a wide range of synthetic polymers, synthetic or Semisynthesis, semisynthetic materials composed primarily of Polymer, polymers. Their defining characteristic, Plasticity (physics), plasticity, allows them to be Injection moulding ...
s to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften
polyvinyl chloride Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons of ...
(PVC). While phthalates are commonly used as plasticizers, not all plasticizers are phthalates. The two terms are specific, unique, and not used interchangeably. Lower-molecular-weight phthalates are typically replaced in many products in the United States, Canada, and European Union over health concerns. They are being replaced by higher molecular-weight phthalates as well as non-phthalic plasticizers. Phthalates are commonly ingested in small quantities via the diet. One of the most commonly known phthalates is bis(2-ethylhexyl) phthalate (DEHP). In many countries, DEHP is regulated as a
toxin A toxin is a naturally occurring poison produced by metabolic activities of living cells or organisms. They occur especially as proteins, often conjugated. The term was first used by organic chemist Ludwig Brieger (1849–1919), derived ...
, and is banned from use in broad categories of consumer goods, such as
cosmetics Cosmetics are substances that are intended for application to the body for cleansing, beautifying, promoting attractiveness, or altering appearance. They are mixtures of chemical compounds derived from either Natural product, natural source ...
, children's toys, medical devices, and food packaging. There are numerous forms of phthalates not regulated by governments.


Production

Phthalate esters are produced industrially by the reaction of phthalic anhydride with excess
alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...
. Often the phthalic anhydride is molten. The monoesterification occurs readily, but the second step is slow: : : The conversion is conducted at high temperatures to drive off the water. Typical catalysts are based on tin or titanium alkoxides or carboxylates. The properties of the phthalate can be varied by changing the alcohol. Around 30 are, or have been, commercially important. Phthalates' share of the global plasticisers market has been decreasing since around 2000 however total production has been increasing, with around 5.5 million tonnes made in 2015, up from around 2.7 million tonnes in the 1980s. The explanation for this is the increasing size of the plasticiser market, largely due driven by increases in PVC production, which nearly doubled between 2000 and 2020. The People's Republic of China is the largest consumer, accounting for around 45% of all use. Europe and the United States together account for around 25% of use, with the remainder widely spread around the world.


Uses


PVC plasticisers

Between 90 and 95% of all phthalates are used as plasticisers for the production of flexible PVC. They were the first commercially important compounds for this role, a historic advantage that has led to them becoming firmly embedded in flexible PVC technology. Among the common plastics, PVC is unique in its acceptance of large amounts of plasticizer with gradual changes in physical properties from a rigid solid to a soft gel. Phthalates derived from alcohols with 7–13 carbon atoms occupy a privileged position as general purpose plasticizers, suitable for almost all flexible PVC applications. Phthalates larger than this have limited compatibility in PVC, with di(isotridecyl) phthalate representing the practical upper limit. Conversely, plasticizers derived from alcohols with 4–6 carbon atoms are too volatile to be used on their own, but have been used alongside other compounds as secondary plasticizers, where they improve low-temperature flexibility. Compounds derived from alcohols with 1–3 carbon atoms are not used as plasticizers in PVC at all, due to excessive fuming at processing temperatures (typically 180-210 °C). Historically DINP, DEHP, BBP, DBP, and DIHP have been the most important phthalates, however many of these are now facing regulatory pressure and gradual phase-outs. Almost all phthalates derived from alcohols with between 3 and 8 carbons are classed as toxic by ECHA. This includes Bis(2-ethylhexyl) phthalate (DEHP or DOP), which has long been the most widely used phthalate, with commercial production dating back to the 1930s. In the EU, the use of DEHP is restricted under REACH and it can only be used in specific cases if an authorisation has been granted; similar restrictions exist in many other jurisdictions. Despite this, the phase-out of DEHP is slow and it was still the most frequently used plasticizer in 2018, with an estimated global production of 3.24 million tonnes. DINP and DIDP are used as a substitutes for DEHP in many applications, as they are not classified as hazardous. Non-phthalate plasticizers are also being increasingly used. Almost 90% of all plasticizers are used in PVC, giving this material improved flexibility and durability. The majority is used in films and cable sheathing. Flexible PVC can consist of over 85% plasticizer by mass, however unplasticized PVC (UPVC) should not contain any.


Non-PVC plasticisers

Phthalates see use as plasticisers in various other polymers, with applications centred around coatings such as lacquers, varnishes, and paints. The addition of phthalates imparts some flexibility to these materials, reducing their tendency to chip. Phthalates derived from alcohols with between 1–4 carbon atoms are used as plasticisers for
cellulose Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important s ...
-type plastics, such as
cellulose acetate In biochemistry, cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, and ...
,
nitrocellulose Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and ...
and cellulose acetate butyrate, with commonly encountered applications including
nail polish Nail polish (also known as nail varnish in British English or nail enamel) is a lacquer that can be applied to the human Nail (anatomy), fingernails or toenails to decorate and protect the nail plates. The formula has been revised repeatedly t ...
. Most phthalates are also compatible with alkyds and
acrylic resin 186 px, Polyhydroxyethylmethacrylate is a typical acrylate resin. An acrylic resin is a thermoplastic or thermosetting plastic substance typically derived from acrylic acid, methacrylic acid and acrylate monomers such as butyl acrylate and me ...
s, which are used in both oil and emulsion based paints. Other plasticised polymer systems include polyvinyl butyral (particularly the forms used to make laminated glass), PVA and its co-polymers like PVCA. They are also compatible in
nylon Nylon is a family of synthetic polymers characterised by amide linkages, typically connecting aliphatic or Polyamide#Classification, semi-aromatic groups. Nylons are generally brownish in color and can possess a soft texture, with some varieti ...
,
polystyrene Polystyrene (PS) is a synthetic polymer made from monomers of the aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per unit weight. It i ...
,
polyurethane Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...
s, and certain
rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Types of polyisoprene ...
s; but their use in these is very limited. Phthalates can plasticise ethyl cellulose, polyvinyl acetate phthalate (PVAP) and cellulose acetate phthalate (CAP), all of which are used to make enteric coatings for tablet and capsule medications. These coatings protect drugs from the acidity of the stomach, but allow their release and absorption in the intestines.


Solvent and phlegmatizer

Phthalate esters are widely used as solvents for highly reactive organic peroxides. Thousands of tonnes are consumed annually for this purpose. The great advantage offered by these esters is that they are phlegmatizers, i.e. they minimize the explosive tendencies of a family of chemical compounds that otherwise are potentially dangerous to handle. Phthalates have also been used for producing
plastic explosive Plastic explosive is a soft and hand-moldable solid form of explosive material. Within the field of explosives engineering, plastic explosives are also known as putty explosives or blastics. Plastic explosives are especially suited for explos ...
s such as Semtex.


Other uses

Relatively minor amounts of some phthalates find use in personal-care items such as eye shadow, moisturizer, nail polish, liquid soap, and hair spray.Peter M. Lorz, Friedrich K. Towae, Walter Enke, Rudolf Jäckh, Naresh Bhargava, Wolfgang Hillesheim "Phthalic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. Low-molecular-weight phthalates like dimethyl phthalate and diethyl phthalate are used as fixatives for perfumes. Dimethyl phthalate has been also used as an insect repellent and is especially useful against ixodid ticks responsible for
Lyme disease Lyme disease, also known as Lyme borreliosis, is a tick-borne disease caused by species of ''Borrelia'' bacteria, Disease vector, transmitted by blood-feeding ticks in the genus ''Ixodes''. It is the most common disease spread by ticks in th ...
. and species of mosquitoes such as ''
Anopheles stephensi ''Anopheles stephensi'' is a primary mosquito vector of malaria in urban India and is included in the same subgenus as ''Anopheles gambiae'', the primary malaria vector in Africa. ''A. gambiae'' consists of a complex of morphologically identical ...
, Culex pipiens and
Aedes aegypti ''Aedes aegypti'' ( or from Greek 'hateful' and from Latin, meaning 'of Egypt'), sometimes called the Egyptian mosquito, dengue mosquito or yellow fever mosquito, is a mosquito that spreads diseases like dengue fever, yellow fever, malar ...
'', Diallyl phthalate is used to prepare vinyl ester resins with good electrical insulation properties. These resins are used to manufacture of electronics components.


History

The development of cellulose nitrate plastic in 1846 led to the patent of castor oil in 1856 for use as the first plasticizer. In 1870, camphor became the more favored plasticizer for cellulose nitrate. Phthalates were first introduced in the 1920s and quickly replaced the volatile and odorous camphor. In 1931, the commercial availability of
polyvinyl chloride Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons of ...
(PVC) and the development of di(2-ethylhexyl) phthalate (DEHP) began the boom of the plasticizer PVC industry.


Properties

Phthalate
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s usually refers to di
alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...
esters of phthalic acid (also called 1,2-benzenedicarboxylic acid, not be confused with the structurally isomeric terephthalic or isophthalic acids); the name "phthalate" derives from phthalic acid, which itself is derived from the word "
naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...
". When added to plastics, phthalates allow the polyvinyl polymers to slide against one another. The phthalates have a clear syrupy liquid consistency and show low water solubility, high oil solubility, and low volatility. The polar carboxyl group contributes little to the physical properties of the phthalates, except when R and R' are very small (such as ethyl or methyl groups). Phthalates are colorless, odorless liquids produced by the reaction of phthalic anhydride with
alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...
s. The mechanism by which phthalates and related compounds plasticize polar polymers has been a subject of intense study since the 1960s. The mechanism is one of polar interactions between the polar centres of the phthalate molecule (the C=O functionality) and the positively charged areas of the vinyl chain, typically residing on the carbon atom of the carbon-chlorine bond. For this to be established, the polymer must be heated in the presence of the plasticizer, first above the Tg of the polymer and then into a melt state. This enables an intimate mix of polymer and plasticizer to be formed, and for these interactions to occur. When cooled, these interactions remain and the network of PVC chains cannot reform (as is present in unplasticized PVC, or PVC-U). The alkyl chains of the phthalate then screen the PVC chains from each other as well. They are blended within the plastic article as a result of the manufacturing process. Because they are not chemically bonded to the host
plastic Plastics are a wide range of synthetic polymers, synthetic or Semisynthesis, semisynthetic materials composed primarily of Polymer, polymers. Their defining characteristic, Plasticity (physics), plasticity, allows them to be Injection moulding ...
s, phthalates are released from the plastic article by relatively gentle means. For example, they can be extracted by extraction with organic solvents and, to some extent, by handling.


Alternatives

Being inexpensive, nontoxic (in an acute sense), colorless, noncorrosive, biodegradable, and with easily tuned physical properties, phthalate esters are nearly ideal plasticizers. Among the numerous alternative plasticizers are dioctyl terephthalate (DEHT) (a terephthalate isomeric with DEHP) and 1,2-cyclohexane dicarboxylic acid diisononyl ester (DINCH) (a hydrogenated version of DINP). Both DEHT and DINCH have been used in high volumes for a variety of products used in contact with humans as alternative plasticizers for DEHP and DINP. Some of these products include medical devices, toys, and food packaging. DEHT and DINCH are more hydrophobic than other phthalate alternatives such as bis(2-ethylhexyl) adipate (DEHA) and diisodecyl adipate (DIDA). Since alternative plasticizers such as DEHT and DINCH are more likely to bind to organic matter and airborne particles indoors, exposure occurs primarily through food consumption and contact with dust. Many bio-based plasticizers based on vegetable oil have been developed.


Occurrence and exposure


Human exposure

Due to the ubiquity of plasticized plastics, people are often exposed to phthalates. For example, most Americans tested by the
Centers for Disease Control and Prevention The Centers for Disease Control and Prevention (CDC) is the National public health institutes, national public health agency of the United States. It is a Federal agencies of the United States, United States federal agency under the United S ...
have
metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
s of multiple phthalates in their urine. Exposure to phthalates is more likely in women and people of color. Differences were found between Mexican-Americans, blacks, and whites in terms of the overall risk of disturbance of glucose homeostasis. With Mexican-Americans having a fasting blood glucose (FBG) increase of 5.82 mg/dL, blacks having a fasting blood glucose increase of 3.63 mg/dL, and whites having a fasting blood glucose increase of 1.79 mg/dL, there was evidence of an increased risk for minorities. Overall, the study concludes that phthalates may alter glucose homeostasis and insulin sensitivity. Higher levels of some phthalate metabolites were associated with elevated FBG, fasting insulin, and insulin resistance. Non-Hispanic black women and Hispanic women have higher levels of some phthalate metabolites. Higher dust concentrations of DEHP were found in homes of children with asthma and allergies, compared with healthy children's homes. The author of the study stated, "The concentration of DEHP was found to be significantly associated with wheezing in the last 12 months as reported by the parents." Phthalates were found in almost every sampled home in Bulgaria. The same study found that DEHP, BBzP, and DnOP were in significantly higher concentrations in dust samples collected in homes where polishing agents were used. Data on flooring materials was collected, but there was not a significant difference in concentrations between homes where no polish was used that have balatum (PVC or linoleum) flooring and homes with wood. High frequency of dusting did decrease the concentration. In general, children's exposure to phthalates is greater than that of adults. In a 1990s Canadian study that modeled ambient exposures, it was estimated that daily exposure to DEHP was 9 μg/kg bodyweight/day in infants, 19 μg/kg bodyweight/day in toddlers, 14 μg/kg bodyweight/day in children, and 6 μg/kg bodyweight/day in adults. Infants and toddlers are at the greatest risk of exposure, because of their mouthing behavior. Body-care products containing phthalates are a source of exposure for infants. The authors of a 2008 study "observed that reported use of infant lotion, infant powder, and infant shampoo were associated with increased infant urine concentrations of hthalate metabolites and this association is strongest in younger infants. These findings suggest that dermal exposures may contribute significantly to phthalate body burden in this population." Although they did not examine health outcomes, they noted that "Young infants are more vulnerable to the potential adverse effects of phthalates given their increased dosage per unit body surface area, metabolic capabilities, and developing endocrine and reproductive systems." Infants and hospitalized children are particularly susceptible to phthalate exposure. Medical devices and tubing may contain 20–40% Di(2-ethylhexyl) phthalate (DEHP) by weight, which "easily leach out of tubing when heated (as with warm saline / blood)". Several medical devices contain phthalates including, but not limited to, IV tubing, gloves, nasogastric tubes, and respiratory tubing. The Food and Drug Administration did an extensive risk assessment of phthalates in the medical setting and found that neonates may be exposed to five times greater than the allowed daily tolerable intake. This finding led to the conclusion by the FDA that, " ildren undergoing certain medical procedures may represent a population at increased risk for the effects of DEHP". In 2008, the Danish Environmental Protection Agency (EPA) found a variety of phthalates in erasers and warned of health risks when children regularly suck and chew on them. The European Commission Scientific Committee on Health and Environmental Risks (SCHER), however, considers that, even in the case when children bite off pieces from erasers and swallow them, it is unlikely that this exposure leads to health consequences. In 2008, the United States National Research Council recommended that the cumulative effects of phthalates and other antiandrogens be investigated. It criticized U.S. EPA guidances, which stipulate that, when examining cumulative effects, the chemicals examined should have similar mechanisms of action or similar structures, as too restrictive. It recommended instead that the effects of chemicals that cause similar adverse outcomes should be examined cumulatively. Thus, the effect of phthalates should be examined together with other antiandrogens, which otherwise may have been excluded because their mechanisms or structure are different.


Food

Phthalates are found in food, especially fast food items. Phthalate DnBP was detected in 81 percent of the samples, while DEHP was found in 70 percent. Diethylhexyl terephthalate (DEHT), the main alternative to DEHP, was detected in 86%. A 2024 study by
Consumer Reports Consumer Reports (CR), formerly Consumers Union (CU), is an American nonprofit consumer organization dedicated to independent product testing, investigative journalism, consumer-oriented research, public education, and consumer advocacy. Founded ...
found phthalates in all but one of the grocery store products and fast foods they tested. Diet is believed to be the main source of DEHP and other phthalates in the general population. Fatty foods such as milk, butter, and meats are a major source. Studies show that exposure to phthalates is greater from ingestion of certain foods, rather than exposure via water bottles, as is most often first thought of with plastic chemicals. Low-molecular-weight phthalates such as DEP, DBP, BBzP may be dermally absorbed. Inhalational exposure is also significant with the more volatile phthalates. PVC tubing, vinyl gloves used in food handling, and food packaging may serve as potential sources of phthalate contamination in fast food. One study, conducted between 2003 and 2010 analysing data from 9,000 individuals, found that those who reported that they had eaten at a
fast food restaurant A fast-food restaurant, also known as a quick-service restaurant (QSR) within the industry, is a specific type of restaurant that serves fast food, fast-food cuisine and has minimal Foodservice#Table service, table service. The food served ...
had much higher levels of two separate phthalates—DEHP and DiNP—in their urine samples. Even small consumption of
fast food Fast food is a type of Mass production, mass-produced food designed for commercial resale, with a strong priority placed on speed of service. ''Fast food'' is a commercial term, limited to food sold in a restaurant or store with frozen, preheat ...
caused higher presence of phthalates. "People who reported eating only a little fast food had DEHP levels that were 15.5 percent higher and DiNP levels that were 25 percent higher than those who said they had eaten none. For people who reported eating a sizable amount, the increase was 24 percent and 39 percent, respectively." Phthalates have a short half-life of less than five hours, so their widespread presence likely indicates continuous exposure rather than long-term accumulation in the body.


Air

Outdoor air concentrations are higher in urban and
suburb A suburb (more broadly suburban area) is an area within a metropolitan area. They are oftentimes where most of a metropolitan areas jobs are located with some being predominantly residential. They can either be denser or less densely populated ...
an areas than in
rural In general, a rural area or a countryside is a geographic area that is located outside towns and cities. Typical rural areas have a low population density and small settlements. Agricultural areas and areas with forestry are typically desc ...
and remote areas. They also pose no acute toxicity. Common plasticizers such as DEHP are only weakly volatile. Higher air temperatures result in higher concentrations of phthalates in the air. PVC flooring leads to higher concentrations of BBP and DEHP, which are more prevalent in dust. A 2012 Swedish study of children found that phthalates from PVC flooring were taken up into their bodies, showing that children can ingest phthalates not only from food but also by breathing and through the skin.


Natural occurrence

Various plants and microorganisms produce small amounts of phthalate esters, the so-called
endogenous Endogeny, in biology, refers to the property of originating or developing from within an organism, tissue, or cell. For example, ''endogenous substances'', and ''endogenous processes'' are those that originate within a living system (e.g. an ...
phthalates.
Biosynthesis Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthe ...
is believed to involve a modified Shikimate pathway The extent of this natural production is not fully known, but it may create a background of phthalate pollution.


Biodegradation

Phthalates do not persist due to rapid
biodegradation Biodegradation is the breakdown of organic matter by microorganisms, such as bacteria and fungi. It is generally assumed to be a natural process, which differentiates it from composting. Composting is a human-driven process in which biodegrada ...
, photodegradation, and anaerobic degradation.


Research

Phthalates are under research as a class of possible endocrine disruptors, substances that may interfere with normal hormonal responses in varied environmental conditions. The concern has sparked demands to ban or restrict the use of phthalates in baby toys. A 2024 review indicated that exposure of mothers to environmental phthalates may have adverse pregnancy outcomes, such as a higher miscarriage rate and lower birth weights. Another review showed small reductions in lung function in adolescents and children who had been exposed to phthalates. A 2017 review indicated ways to avoid exposure to phthalates: (1) eating a balanced diet to avoid ingesting too many endocrine disruptors from a single source, (2) eliminating canned or packaged food in order to limit ingestion of DEHP phthalates leached from plastics, and (3) eliminating use of any personal product such as moisturizer, perfume, or cosmetics that contain phthalates. Exposure to phthalates may increase the risk of
asthma Asthma is a common long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wh ...
. A 2018 study indicated that exposure to phthalates during developmental stages in childhood may negatively affect adipose tissue function and metabolic homeostasis, possibly increasing the risk of obesity.


Legal status

The governments of Australia, New Zealand, Canada, the US, and California have determined that many phthalates are not harmful to human health or the environment in amounts typically found, and therefore are legally unregulated. The focus for regulation in these jurisdictions has been mainly on diethyl phthalate (DEHP), which is generally regarded as a
carcinogen A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...
ic toxin requiring regulation. The European Chemicals Agency (European Union, EU) regards ortho-phthalates, such as DEHP, dibutyl phthalate, diisobutyl phthalate, and benzyl butyl phthalate as potentially harmful to fertility, unborn babies, and the
endocrine system The endocrine system is a messenger system in an organism comprising feedback loops of hormones that are released by internal glands directly into the circulatory system and that target and regulate distant Organ (biology), organs. In vertebrat ...
. The EU also regulates some phthalates to protect the environment.


Australia and New Zealand

A 2017 survey of foods and packaging in Australia and New Zealand led to recognition of DEHP and diisononyl phthalate as among possible contaminants posing a risk to human health, resulting in several regulations on these phthalates in both countries. Australia has a permanent ban on certain children's products containing DEHP, which is considered poisonous if products containing it are placed in the mouths of children up to three years old.


Canada

In 1994, a
Health Canada Health Canada (HC; )Health Canada is the applied title under the Federal Identity Program; the legal title is Department of Health (). is the Structure of the Canadian federal government#Departments, with subsidiary units, department of the Gove ...
assessment found that DEHP and another phthalate product, B79P, were harmful to human health. The Canadian federal government responded by banning their use in cosmetics and restricting their use in other applications, such as soft toys and child-care products. In 1999, DEHP was put on the national List of Toxic Substances, under the Canadian Environmental Protection Act, 1999, and in 2021, it was deemed a risk to the environment. It is on the List of Ingredients that are Prohibited for Use in Cosmetic Products. Twenty of the 28 phthalate substances under national screening programs are considered possible risks to human health or the environment. As of 2021, regulations to protect the environment against DEHP and B79P have not been enacted.


European Union

Some phthalates have been restricted in the European Union for use in children's toys since 1999. DEHP, BBP, and DBP are restricted for all toys; DINP, DIDP, and DNOP are restricted only in toys that can be taken into the mouth. The restriction states that the amount of these phthalates may not be greater than 0.1% mass percent of the plasticized part of the toy. Generally, the high molecular weight phthalates DINP, DIDP, and DPHP have been registered under REACH and have demonstrated their safety for use in current applications. They are not classified for any health or environmental effects. The low molecular weight products BBP, DEHP, DIBP, and DBP were added to the Candidate list of Substances for Authorisation under REACH in 2008–09, and added to the Authorisation list, Annex XIV, in 2012. This means that from February 2015 they are not allowed to be produced in the EU unless authorisation has been granted for a specific use, although they may still be imported in consumer products. The creation of an Annex XV dossier, which could ban the import of products containing these chemicals, was being prepared jointly by the ECHA and Danish authorities, and expected to be submitted by April 2016. Since 2021, the European Waste Framework Directive requires manufacturers, importers and distributors of products containing phthalates on the REACH Candidate List to notify the European Chemicals Agency. In November 2021, the
European Commission The European Commission (EC) is the primary Executive (government), executive arm of the European Union (EU). It operates as a cabinet government, with a number of European Commissioner, members of the Commission (directorial system, informall ...
added endocrine disrupting properties to DEHP and other phthalates, meaning that companies must apply for REACH authorization for some uses that were previously exempted, including in food packaging, medical devices, and drug packaging.


Legislation, additional


United States

During August 2008, the
United States Congress The United States Congress is the legislature, legislative branch of the federal government of the United States. It is a Bicameralism, bicameral legislature, including a Lower house, lower body, the United States House of Representatives, ...
passed and President
George W. Bush George Walker Bush (born July 6, 1946) is an American politician and businessman who was the 43rd president of the United States from 2001 to 2009. A member of the Bush family and the Republican Party (United States), Republican Party, he i ...
signed the Consumer Product Safety Improvement Act (CPSIA), which became public law 110–314. Section 108 of that law specified that as of February 10, 2009, "it shall be unlawful for any person to manufacture for sale, offer for sale, distribute in commerce, or import into the United States any children's toy or child care article that contains concentrations of more than 0.1 percent of" DEHP, DBP, or BBP and "it shall be unlawful for any person to manufacture for sale, offer for sale, distribute in commerce, or import into the United States any children's toy that can be placed in a child's mouth or child care article that contains concentrations of more than 0.1 percent of" DINP, DIDP, and DnOP. Furthermore, the law requires the establishment of a permanent review board to determine the safety of other phthalates. Prior to this legislation, the Consumer Product Safety Commission had determined that voluntary withdrawals of DEHP and diisononyl phthalate (DINP) from teethers, pacifiers, and rattles had eliminated the risk to children, and advised against enacting a phthalate ban. In 1986, California voters approved an initiative to address concerns about exposure to toxic chemicals. That initiative became the Safe Drinking Water and Toxic Enforcement Act of 1986, also called Proposition 65. In December 2013, DINP was listed as a chemical "known to the State of California to cause cancer" Beginning in December 2014, companies with ten or more employees manufacturing, distributing or selling the product(s) containing DINP were required to provide a clear and reasonable warning for that product. The California Office of Environmental Health Hazard Assessment, charged with maintaining the Proposition 65 list and enforcing its provisions, has implemented a "No Significant Risk Level" of 146 μg/day for DINP. The CDC provided a 2011 public health statement on diethyl phthalate describing regulations and guidelines concerning its possible harmful health effects. Under laws for
Superfund sites Superfund sites are Pollution, polluted locations in the United States requiring a long-term response to clean up hazardous material contaminations. Sites include landfills, mines, manufacturing facilities, processing plants where toxic waste h ...
, the Environmental Protection Agency named diethyl phthalate as a hazardous substance. The
Occupational Safety and Health Administration The Occupational Safety and Health Administration (OSHA; ) is a regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. The United States Congress established ...
stated that the maximum amount of diethyl phthalate allowed in workroom air during an 8-hour workday, 40-hour workweek, is 5 milligrams per cubic meter.


Identification in plastics

Phthalates are used in some, but not all, PVC formulations, and there are no specific labeling requirements for phthalates. PVC plastics are typically used for various containers and hard packaging, medical tubing and bags, and are labeled "Type 3". However, the presence of phthalates rather than other plasticizers is not marked on PVC items. Only unplasticized PVC (uPVC), which is mainly used as a hard construction material, has no plasticizers. If a more accurate test is needed, chemical analysis, for example by
gas chromatography Gas chromatography (GC) is a common type of chromatography used in analytical chemistry for Separation process, separating and analyzing compounds that can be vaporized without Chemical decomposition, decomposition. Typical uses of GC include t ...
or liquid chromatography, can establish the presence of phthalates. Polyethylene terephthalate (PET, PETE, Terylene, Dacron) is the main substance used to package bottled water and many sodas. Products containing PETE are labeled "Type 1" (with a "1" in the recycle triangle). Although the word "phthalate" appears in the name, PETE does not use phthalates as plasticizers. The terephthalate polymer PETE and the phthalate ester plasticizers are chemically different substances. Despite this, however, many studies have found phthalates, such as DEHP in bottled water and soda. One hypothesis is that these may have been introduced during plastic recycling.


See also

* Xenoestrogen * Non-phthalate plasticizers such as ** 1,2-Cyclohexane dicarboxylic acid diisononyl ester, ** Dioctyl terephthalate, and ** Citrates * Antiandrogens in the environment


References


Further reading

* * *


External links

* : video of Steve Risotto of the American Chemistry Council, 23 October 2009 {{Authority control Plasticizers Suspected testicular toxicants Suspected fetotoxicants Suspected teratogens Endocrine disruptors