uses of phthalic acid

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It is recommended to take special care regarding the storage conditions on bottles. Physical Properties 2.2. Phthalates are among the most common synthetic chemicals to which humans are exposed. This chemical is sensitive to exposure to extreme heat. Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). The EU has already taken steps to reduce the use of certain phthalates (such as DEHP). Phthalates are also ubiquitous food and environmental contaminants. Esters of phthalic acid are obtained by the reaction of phthalic anhydride or the acid with alcohol and are used in diffusion pumps and in place of mercury in manometers. They are found in many plastic consumer products, including adhesives and glues, paints, packaging, children’s toys, electronics, flooring, medical equipment, personal care products, air fresheners, food products, pharmaceuticals, and textiles. Our editors will review what you’ve submitted and determine whether to revise the article. In rodents, the end results are impaired masculinization of the exposed offspring and impaired sperm production later in life (Kay et al., 2014; David, 2006). PAEs with long alkyl chain (such as DEHP) are mineralized at a slower rate. Dermal exposure may also be important routes of exposures to phthalates such as DBP, which are used in many cosmetics including perfume, hair gels, hair sprays, body lotion, deodorant, and nail polish (Koch et al., 2003a; Koo and Lee, 2007). (Ed. It is a conjugate acid of a phthalate (1-) … Also of practical importance are the cyclic imide (phthalimide) and dichloranhydride (phthalyl chloride) of ortho-phthalic acid, as well as phthalylsulfathiazole (Ftalazol). Due credit and reputation for authors [authorship tracking technology]. Phthalates are obesogenic EDCs, found in many plastics such as tubing and vinyl flooring, as well as in household and personal care products, fragrances, and food packaging (reviewed in Heindel et al., 2017). Many of the phthalates are individually listed by the OECD in their 2004 list of HPV chemicals [34]. The mechanism by which phthalates interfere with thyroid function is not entirely understood. PHTHALIC ACID is a carboxylic acid. See more. Prenatal exposure to DEHP leads to reduced ovarian weight and increased uterine weight in female mice. Table 44.2. Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. Phthalates are chemicals used as plasticizers and in adhesives, solvents, cosmetics, and other products. Humans are exposed to phthalates through ingestion, inhalation, and dermal contact. Therefore, DEHP, DBP, BBP, and DIBP have been classified as being reproductive toxicants (ECHA, 2017). Typical concentrations of DEHP in various sludge types are listed in Table 4 based on measurements performed in sludge samples taken from four sewage-treatment plants in Seville. Jan Ludvig Lyche, in Reproductive and Developmental Toxicology (Second Edition), 2017. Concentrations of DEHP in indoor air in Japan were reported to be up to 1000-fold higher than outdoor air concentrations (Otake et al., 2004). They are also used in PVC (Heudorf et al., 2007). A process for the preparation of nitrophthalic acid by the nitration of phthalic acid and/or phthalic anhydride using only nitric acid, said nitric acid having a concentration of at least about 95% by weight, and then recovering the nitrophthalic acid formed from the nitric acid solution. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. Safe alternatives such as glass or polyethylene plastics and phthalate-free labeled are highly recommended. It is generally understood that phthalates with backbones of three to six carbons share similar modes of action when it comes to adversely affecting the reproductive system in experimental animals. (NTP, 1992). They are found in many plastic consumer products, including adhesives and glues, paints, packaging, children’s toys, electronics, flooring, medical equipment, personal care products, air fresheners, food products, pharmaceuticals, and textiles. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780123864543009635, URL: https://www.sciencedirect.com/science/article/pii/B9780128042397000445, URL: https://www.sciencedirect.com/science/article/pii/B978012801238364415X, URL: https://www.sciencedirect.com/science/article/pii/B9780128012994000128, URL: https://www.sciencedirect.com/science/article/pii/B9780080885049004967, URL: https://www.sciencedirect.com/science/article/pii/B9780128011393000016, URL: https://www.sciencedirect.com/science/article/pii/B9780128012383960033, URL: https://www.sciencedirect.com/science/article/pii/B9780128012383643829, URL: https://www.sciencedirect.com/science/article/pii/B9780128012383652078, Encyclopedia of Toxicology (Third Edition), 2014, Encyclopedia of Toxicology (Third Edition), Reproductive and Developmental Toxicology (Second Edition), Phthalates are diesters of 1,2-benzenedicarboxylic acid (, Bouma and Schakel, 2002; Wooten and Smith, 2013, http://www.environmentalhealth.ca/fall02pretty.html, Center for Devices and Radiological Health, 2001; Strømmen et al., 2016, Dine et al., 2000; Buchta et al., 2003, 2005; Koch et al., 2005b, Encyclopedia of Reproduction (Second Edition), Environmental Contamination and Testicular Function, Bioenvironmental Issues Affecting Men's Reproductive and Sexual Health, Comprehensive Biotechnology (Second Edition). DEHP has been detected in higher concentration values than all the other phthalates in raw or treated sewage. Figure 44.1. On the other hand, higher biodegradation of DEHP during the aerobic conditions that prevail during composting leads to lower DEHP concentrations (expressed as mass of DEHP per mass of sludge solids in composted sludge), despite the reduction of volatile solids that naturally takes place during composting). Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. Polyesters containing isophthalic acid are also used extensively in industrial coatings applications for home appliances, automobiles, aluminum siding, and metal office furniture. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. In this way, MEHP promoted preadipocyte differentiation and adipogenesis. Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. These phthalates seem to act via multiple modes of action. The most widely used phthalates are di(2-ethylhexyl) phthalate (DEHP), diisodecyl phthalate, and diisononyl phthalate. The use information is displayed per substance life cycle stage (consumer use, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites or in manufacturing). Sigal A. Willner, Bruce Blumberg, in Encyclopedia of Endocrine Diseases (Second Edition), 2019. The primary use of phthalic anhydride is a precursor to phthalate esters, used as plasticizers in vinyl chloride. (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. Phthalic acid has a chemical formula C 6 H 4 (CO 2 H) 2 and comprises a six-carbon benzene ring with two carboxylic acid groups (-COOH) attached. (2016) measured dermal uptake in humans exposed in an experimental chamber and showed higher uptake in through bare skin compared with those wearing clean clothes. Certain phthalates have been found to interfere with early male reproductive development by altering fetal germ cell development or inhibiting synthesis of sex steroid hormones. Baby-care products represent a dermal route of phthalate exposure with relevance for infants, as exposure to lotions, powder, and shampoo was associated with increased levels of metabolites in infant urine (Sathyanarayana et al., 2008). phthalic acid: ChEBI ID CHEBI:29069: Definition A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. CAMEO Chemicals. Manufacturers use low-MW phthalates such as DMP, di-ethyl phthalate (DEP), and DBP as solvents in personal care products (perfumes, lotions, cosmetics), insecticides, lacquers, and in coatings including those used to provide timed releases in some pharmaceuticals. By continuing you agree to the use of cookies. Phthalic Anhydride 2.1. We use cookies to help provide and enhance our service and tailor content and ads. Phthalic acid is produced in final stage metabolites of phthalic acid esters. The Levels of Urinary Di(2-ethylhexyl) Phthalate Metabolites Measured in Patients Undergoing Medical Treatments, Radwa Barakat, CheMyong J. Ko, in Encyclopedia of Reproduction (Second Edition), 2018. Biodegradation is the main mechanism of degradation of PAEs in the environment (the rates of hydrolysis and photolysis are very low). Unfortunately, plastic containers, such as food utilities, are the main source of DEHP, in which phthalates are physically dissolved in plastic not by chemical bounding. This acid was invented by a great French chemist Auguste Laurent through the oxidizing naphthalene tetrachloride. DEHP is generally applied in medical devices, including cardiac catheters, endotracheal tubes, and some implanted devices, whereas DINP is commonly found in wires, cables, hoses, and plastic toys. DEHP is produced from phthalate anhydride reacting with 2-ethylhexanol. Morrison et al. Source: GreenFacts Phthalic acid, isophthalic acid and terephthalic acid are all isomers of each other. Le catalyseur du type V.P.O. DEHP as well as other PAEs seem to be estrogen disruptors; high doses of DEHP on mouse embryos inhibit the synthesis of testosterone. Exposure during fetal development altered follicular recruitment and development, eventually causing premature ovarian failure. Studies in humans have shown varied effects associated with adipogenesis and obesity, including one finding that phthalate exposure during pregnancy was associated with elevated triglyceride levels in cord blood with increased body mass at 3 months, in boys (Kim et al., 2016). The annual production of phthalic anhydride exceeded 1,000,000 metric tons in the late 20th century; most of it was used as an ingredient of polyesters, including alkyd resins (vehicles for paints and enamels), and simple esters used as plasticizers for polyvinyl chloride and other polymers. Children are among those highest exposed to phthalates, and infants in neonatal intensive care units that are treated with PVC plastic medical devices containing DEHP, can be significantly exposed. Recent studies have found harmful effects of prenatal exposure to DEHP. Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. No damage or toxicity to humans after handling the substance for a prolonged period has been reported (BG Chemie 1990). Phthalic anhydride can also be prepared from phthalic acid by simple thermal dehydration. This article was most recently revised and updated by, https://www.britannica.com/science/phthalic-acid. In addition to dietary exposure, oral intake of phthalates also occurs when children mouth, suck, or chew on toys containing phthalates (Bouma and Schakel, 2002; Wooten and Smith, 2013). The world's first wiki where authorship really matters. Long-chain phthalates such as diisododecyl phthalate (DIDP) and diisononyl phthalate (DINP) are abundantly used, and while DIDP does not appear to influence reproductive function or markers of androgen insufficiency in early life, DINP does seem to affect male reproduction via alterations of testosterone production, though with less potency than e.g., DEHP and DBP (ECHA, 2013). Although the levels of phthalates in bottled waters have been detected as low, high consumption of such waters leads to a concern. Define 1,2-benzenedicarboxylic acid. Tests on animals (in vivo) as well as laboratory tests (in vitro) have shown that DEHP and its metabolites have an impact on vital organs such as the heart, kidney, and the reproductive system. Phthalic acid definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. The dinitrile of ortho-phthalic acid (phthalonitrile) is used in the production of phthalocyanine dyes and polyphthalocyanines. Xenotransplants of testis tissue from different species appear to respond differently to phthalate exposure with respect to testosterone production, but similarly with respect to germ cell changes. From 2009, it was prohibited to manufacture, distribute, or import into the United States any children's toy or child-care article that contains concentrations of more than 0.1% of DEHP, DBP, BBP, DINP, DIDP, or DnOP (GovTrack.us, 2009). N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110; 33 KB. ), The Handbook of Environmental Chemistry. Being structurally similar, they can present difficulties to reverse-phase HPLC separation. Julie Boberg, ... Anne Marie Vinggaard, in Encyclopedia of Reproduction (Second Edition), 2018. Phthalates are widely employed in many personal care products, cosmetics as well as plastics (softening of products made by these materials, especially vinyl plastics), paper coating, paints, and adhesives. 44.1) and they are synthetically produced by esterification of phthalic acid with different alcohols. However, biodegradation of DEHP is active during the subsequent steps too (such as the maturation step) rendering the whole process duration an important factor for the DEHP removal. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. Phthalates [41,42] (Figure 1.7) are esters of phthalic acid and are used mainly as plasticizers to increase flexibility, transparency, and durability of plastic materials. Ring in the new year with a Britannica Membership. Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. Other phthalates detected in indoor air include butyl benzyl phthalate (BBzP), di-n-butyl phthalate (DnBP), di-isobutyl phthalate (DiBP), and DEP (Bornehag and Nanberg, 2010). The also showed that the levels of DEHP were high in the blood bags (6.6%), the tubing (25.2%), and the filter (22.3%). Current methods for detecting this doping focus on analyzing DEHP metabolites, which enter the stored blood from blood bags. These resins are polyesters of acids … Consequently, low-MW phthalates with short alkyl groups such as di-methyl phthalate (DMP) and DBP are more water soluble, whereas the long-chained phthalates are poorly soluble. DEHP removal during sludge composting, Philippa D. Darbre, in Endocrine Disruption and Human Health, 2015. What Are Endocrine Disrupters and Where Are They Found? Despite phthalates not being identified on any of the labels, they were present in 52 of the products (http://www.environmentalhealth.ca/fall02pretty.html). The diethyl and dihexyl esters are very widely used for this purpose. Because of the toxic effects associated with phthalates, attention has also been put on phthalates in medication and US Food and Drug Association (FDA) has recommended against use of DEP and DHEP as excipients in medication. It is an isomer of isophthalic acid and terephthalic acid. Effects of phthalic acid esters on fetal health/Uticaj estara ftalne kiseline na fetalno zdravlje The phthalic acid, 1,2-benzenedicarboxylic acid, bis (2-methylpropyl) ester, is used in the preparation of perfumes and cosmetics. Several studies have also shown a positive association between urinary phthalates and serum TSH, although the overall strength of this association is weaker than that between urinary phthalates and serum thyroid hormone levels (Gore et al., 2015; Dirtu et al., 2013; Wu et al., 2013). Higher concentrations of metabolites from DBP and DEP, as well as DEHP, were also found in women than in men in a Taiwanese population (Huang et al., 2015). DEHP is considered very toxic to humans because it has an adverse effect on fertility and on embryo development and, moreover, it is possibly carcinogenic. Butylbenzylphthalate is used in the manufacture of foamed PVC, which is used mostly as a flooring material. Let us know if you have suggestions to improve this article (requires login). products.metrohm.com. Hydrazide of 3-Nitrophthalic acid.jpg 4,320 × 2,432; 1.91 MB. Consequently, phthalates are never employed in plastic food wraps marketing in the digested!, inhalation, and synthetic fibers from Clark, K., Cousins, I.T.,,! Dehp leads to reduced ovarian weight and increased uterine weight in female mice an of. Low cost cosmetics and personal care and pharmaceutic products, purchased directly from stores were! 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