Phthalates

Phthalates (US: /ˈθæleɪts/,^[1] UK: /ˈθɑːleɪtsˌ ˈfθælɪts/^[2][3]), or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften polyvinyl chloride (PVC). Note that while phthalates are usually plasticizers, not all plasticizers are phthalates. The two terms are specific and unique and cannot be used interchangeably.

Lower-molecular-weight phthalates are being replaced in many products in the United States, Canada, and European Union over health concerns.^[4][5] They are being replaced by higher molecular-weight phthalates as well as non-phthalic plasticizers.

Prevalence and human exposure

Due to the ubiquity of plasticized plastics, the majority of people are exposed to some level of phthalates. For example, most Americans tested by the Centers for Disease Control and Prevention have metabolites of multiple phthalates in their urine.^[6] In February 2009, the Joint Research Centre (JRC) of the European Commission published a review of methods to measure phthalates in food.^[7]

In 2021, a study looked for phthalates in 64 fast food items. Phthalate

The properties of the phthalate can be varied by changing the alcohol,^[12] allowing for an almost limitless range of products, although only around 30 are, or have been, commercially important. Phthalates' share of the global plasticisers market has been decreasing since around 2000. Despite this the global production of phthalates has continued to rise. In 2015 total production of was around 5.5 million tonnes,^[13] up from around 2.7 million tonnes in the 1980s.^[14] The reason for this has been the increasing size of the plasticiser market (a smaller slice of a much bigger pie), driven by increases in PVC production, which nearly doubled between 2000 and 2020.^[15] 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.^[13]

Natural occurrence

Various plants and microorganisms have been reported to naturally produce small amounts of phthalate esters (

Between 90 and 95% of all phthalates are used as plasticisers for the production of flexible PVC.^[21][22] They were the first commercially important compounds for this role,^[23] a historic advantage that has led to them becoming firmly embedded in flexible PVC technology.^[24] 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.^[24] Phthalates derived from alcohols with 7-13 carbon atoms occupy a privileged position as general purpose plasticizers, suitable for almost all flexible PVC applications.^[25][24] 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 excessive fuming at processing temperatures (typically 180-210 °C).^[24]

Historically DINP,

Almost 90% of all plasticizers are used in PVC, giving this material improved flexibility and durability.[29] The majority is used in films and cable sheathing.^[27] 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-type plastics, such as cellulose acetate, nitrocellulose and cellulose acetate butyrate, with commonly encountered applications including nail polish. Most phthalates are also compatible with alkyds and acrylic resins, which are used in both oil and emulsion based paints.

Other plasticised polymer systems include

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

Relatively minor amounts of some phthalates find use in personal-care items such as eye shadow, moisturizer, nail polish, liquid soap, and hair spray.[33]^[34][35] Low-molecular-weight phthalates like dimethyl phthalate and diethyl phthalate are used as fixatives for perfumes.^[36][37] Dimethyl phthalate has been also used as an insect repellent and is especially useful against ixodid ticks responsible for Lyme disease.^[38] and species of mosquitoes such as Anopheles stephensi, Culex pipiens and Aedes aegypti,^[39][40][41]

Diallyl phthalate is used to prepare vinyl ester resins with excellent electrical insulation properties, these are used to manufacture of electronics components. Alkyds are sometimes classes as phthalates, as they meet the technical definition, however, being polymeric esters of phthalic acid their properties and applications are very different.

History

The development of

Because they are not chemically bonded to the host plastics, 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

Many bio-based plasticizers based on vegetable oil have been developed.[45]

Environmental impact

Phthalates are easily released into the environment. In general, they do not persist due to rapid biodegradation, photodegradation, and anaerobic degradation. Outdoor air concentrations are higher in urban and suburban areas than in rural and remote areas.^[46] They also pose no acute toxicity.^[32]

Because of their

In a 2008 Bulgarian study, higher dust concentrations of DEHP were found in homes of children with asthma and allergies, compared with healthy children's homes.[51] 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."^[51] 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.^[51]

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.^[49] 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 [phthalate 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."^[52]

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)".^[53] 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, "[c]hildren undergoing certain medical procedures may represent a population at increased risk for the effects of DEHP".^[53]

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.^[54]

Phthalates are also found in some medications, where they are used as inactive ingredients in producing enteric coatings. Urinary concentrations of monobutyl phthalate, a DBP metabolite of Asacol (a particular formulation of mesalamine) can be 50 times higher than the mean of nonusers.^[55] The study showed that exposures from phthalate-containing medications can far exceed population levels from other sources.^[55] DBP in medications raises concern about health risks due to the high level of exposures associated with taking these medications, especially in vulnerable segments of the population, including pregnant women and children.^[55]

In 2008, the

hazard ratios were below 2 in both cases. The study estimated that phthalates may contribute to 91,000–107,000 premature deaths each year among people aged 55–64 in the United States.^[58]

Endocrine disruption

Further information: Endocrine disruptor § Phthalates

Phthalates enter the bloodstream and disrupt sex hormone production, interfering with sexual development in infants and sexual behaviour in adults. Levels of phthalates have been dose-dependently linked to reduced anogenital distance^[59] decreased sexual desire and satisfaction in women,^[60] and malformed genital development in rats.

Phthalates act by mimicking the female hormone estrogen, which in turn inhibits production of the male hormone testosterone. As such, phthalates are considered to be endocrine disruptors^[61][62][63]—a substance that interferes with the normal hormonal mechanisms that allow a biological organism to interact with its environment, and has sparked demands to ban or restrict its use in baby toys.^[61]

Endocrine disruptors exhibit numerous behaviors that can make studying them a challenge. There can be a lag between when someone is exposed to an endocrine disruptor and any symptoms manifesting themselves–in particular fetal and early childhood exposure may have consequences later in adulthood.

epigenetically to one's offspring without them being directly exposed to the endocrine disruptors.^[65] Finally, particularly low levels of exposure may still have significant effects, and exposure to multiple endocrine disruptors across a variety of compounds (not just phthalates) may synergistically combine to cause a greater effect.^[61][64] Evaluating the actual effects of a specific compound such as a particular phthalate requires examining cumulative exposure across multiple compounds, rather than evaluating one compound in isolation.^[64]

A widespread concern about phthalate exposure is the possibility (though not conclusive) that it is the cause of a worldwide drop in male fertility.[66]^[67][68] Studies have shown that phthalates cause abnormalities in the reproductive systems of animals,^[69] with the greatest effects when the animal is exposed during gestation and immediately thereafter.^[70] Numerous studies on adult male humans show the similar result that phthalate exposure correlates with worsening metrics of male fertility, such as semen quality, the quantity of damaged DNA in sperm, decreased sperm motility, decreased semen volume, and other metrics.^[62][70][71] Phthalates causing harm to the male reproductive system is plausible,^[72] and continues to be researched.

The effect of phthalates on the female reproductive system is also not fully understood yet. Current studies indicate phthalates have negative effects on folliculogenesis and steroidogenesis.^[73]

Early research also shows phthalate exposure may be associated with diabetes and insulin resistance, breast cancer, obesity,^[74] metabolic disorders, and immune function.^[63]

There are possible (though not conclusive) associations between phthalate exposure and adverse child neurodevelopment,

autistic behaviors and lower cognitive and motor development.^[77] Most common associations found in medical reports link the phthalates exposure to hyperactivity, aggression, and other adverse behaviors.^[77] Some studies have found the childhood exposure to be as early as in utero.^[78]

In many cases, there are studies that show connections between phthalates and these negative outcomes, as well as studies that show no connection; this is likely due to the research challenges outlined above, and when resolved, could show that phthalate exposure does not cause health effects, or even that they have a much greater effect than currently predicted.[64] In all cases, larger studies are needed to demonstrate incontrovertibly what effect phthalate exposure has on human health.

A

DEHP phthalates leached from plastics, and (3) eliminating use of any personal product such as moisturizer, perfume, or cosmetics that contain phthalates.^[64] Eliminating personal products containing phthalates can be particularly difficult or impossible due to some countries such as the United States not requiring them to be disclosed in a list of ingredients.^[79]

Endocannabinoid system disruption

Phthalates block

CB₁ as allosteric antagonists.^[80]

Other effects

This section needs more primary sources. Please review the contents of the section and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. Find sources: "Phthalates" – news · newspapers · books · scholar · JSTOR (April 2022)

There may be a link between the

obesity epidemic and endocrine disruption and metabolic interference. Studies conducted on mice exposed to phthalates in utero did not result in metabolic disorder in adults.^[81] However, "in a national cross-section of U.S. men, concentrations of several prevalent phthalate metabolites showed statistically significant correlations with abnormal obesity and insulin resistance."^[81] Mono-ethylhexyl-phthalate (MEHP), a metabolite of DEHP, has been found to interact with all three peroxisome proliferator-activated receptors (PPARs).^[81] PPARs are members of the nuclear receptor superfamily. The author of the study stated "The roles of PPARs in lipid and carbohydrate metabolism raise the question of their activation by a sub-class of pollutants, tentatively named metabolic disrupters."^[81] Phthalates belong to this class of metabolic disruptors. It is a possibility that, over many years of exposure to these metabolic disruptors, they are able to deregulate complex metabolic pathways in a subtle manner.^[81]

In order to build up adipose tissue and establish metabolic homeostasis, it has been established that early childhood and puberty are crucial developmental stages. Exposure to endocrine disruptors, such as phthalates, during these crucial developmental stages may negatively affect adipose tissue function and metabolic homeostasis, increasing the risk of obesity.[82] The prevalence of obesity, particularly in children, is rising, according to mounting evidence, which suggests that increased exposure to phthalates through food packaging materials is to blame. In a study conducted on schoolchildren in China, the concentration of mono-n-butyl phthalate (MnBP) was assessed in urine samples. Additionally, increased exposure to phthalates has been linked to an increase in MnBP. MnBP has been linked to significant increases in weight and obesity in schoolchildren. Significant increases in MnBP concentration were found in the study's urine samples.^[82] The disruption of the arginine and proline metabolism associated with this elevated MnBP concentration as a result of phthalate exposure is thought to be a factor in the pathophysiological changes associated with childhood obesity.

Large amounts of specific phthalates fed to rodents have been shown to damage their

WHO. Later studies on primates showed that the mechanism is specific to rodents; humans are resistant to the effect.^[83]

The carcinogen classification was subsequently withdrawn.

Legal status

Canada

In 1994, a Health Canada 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.^[84]

A 2017 assessment found that B79P and DEHP may cause environmental damage. As of 2019, regulations to protect the environment against DEHP and B79P have not yet been put into place.^[85]

European Union

The use of some phthalates has been restricted in the European Union for use in children's toys since 1999.

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 2008–9, and added to the Authorisation list, Annex XIV, in 2012.^[4] 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, however they may still be imported in consumer products.^[87] 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.^[88]

In 2006 the Dutch office of Greenpeace UK sought to encourage the European Union to ban sex toys that contained phthalates.^[89]

United States

During August 2008, the

DIDP, 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.^[91]

In another development in 1986, California voters approved an initiative to address their growing concerns about exposure to toxic chemicals. That initiative became the Safe Drinking Water and Toxic Enforcement Act of 1986, better known by its original name of Proposition 65.[92] In December 2013 DINP was listed as a chemical "known to the State of California to cause cancer"^[93] This means that, starting December 2014, companies with ten or more employees manufacturing, distributing or selling the product(s) containing DINP are 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.^[94]

Identification in plastics

Phthalates are used in some, but not all,

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.^[96] Despite this, however, a number of studies have found phthalates such as DEHP in bottled water and soda.^[97] One hypothesis is that these may have been introduced during plastic recycling.^[97]

See also

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

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Further reading

• Lovekamp-Swan T, Davis BJ (February 2003). "Mechanisms of phthalate ester toxicity in the female reproductive system". Environmental Health Perspectives. 111 (2): 139–145.
  PMID 12573895
  .
• Tickner JA, Schettler T, Guidotti T, McCally M, Rossi M (January 2001). "Health risks posed by use of Di-2-ethylhexyl phthalate (DEHP) in PVC medical devices: a critical review". American Journal of Industrial Medicine. 39 (1): 100–111.
  S2CID 23676863
  .
• Kohn MC, Parham F, Masten SA, Portier CJ, Shelby MD, Brock JW, Needham LL (October 2000). "Human exposure estimates for phthalates". Environmental Health Perspectives. 108 (10): A440–A442.
  PMID 11097556
  .
• Centers for Disease Control. "National Report on Human Exposure to Environmental Chemicals. Updated Tables, February 2011". Archived from the original on 4 January 2010.
• Centers for Disease Control. "Phthalate Fact Sheet". Archived from the original on 29 December 2010.
• Centers for Disease Control. "Agency for Toxic Substances and Disease Registry-Public Health Statement for Di(2-ethylhexyl) phthalate DEHP". Archived from the original on 2 November 2019. Retrieved 28 December 2021.
• Latini G, Del Vecchio A, Massaro M, Verrotti A, De Felice C (September 2006). "Phthalate exposure and male infertility". Toxicology. 226 (2–3): 90–98.
  PMID 16905236
  .
• Amaral Mendes JJ (June 2002). "The endocrine disrupters: a major medical challenge". Food and Chemical Toxicology. 40 (6): 781–788.
  PMID 11983272
  .

External links

• Media related to Phthalates at Wikimedia Commons