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Phthalate Esters
Phthalates (, ), 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, those derived from C3-C6 alcohols, are being gradually replaced in many products in the United States, Canada, and European Union over health concerns. They are being replaced by high-molecular-weight phthalates (those with more than six carbons in their backbone, which gives them increased permanency and durability), as well as alternative plasticizers not based on phthalic anhydride. In 2010, the market was still dominated by high-phthalate plasticizers; however, due to legal provisions and growing environmental a ...
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Phthalates
Phthalates (, ), 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, those derived from C3-C6 alcohols, are being gradually replaced in many products in the United States, Canada, and European Union over health concerns. They are being replaced by high-molecular-weight phthalates (those with more than six carbons in their backbone, which gives them increased permanency and durability), as well as alternative plasticizers not based on phthalic anhydride. In 2010, the market was still dominated by high-phthalate plasticizers; however, due to legal provisions and growing environmental a ...
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Molecular Weight
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and biochemistry, the distinction from ions is dropped and ''molecule'' is often used when referring to polyatomic ions. A molecule may be homonuclear, that is, it consists of atoms of one chemical element, e.g. two atoms in the oxygen molecule (O2); or it may be heteronuclear, a chemical compound composed of more than one element, e.g. water (two hydrogen atoms and one oxygen atom; H2O). In the kinetic theory of gases, the term ''molecule'' is often used for any gaseous particle regardless of its composition. This relaxes the requirement that a molecule contains two or more atoms, since the noble gases are individual atoms. Atoms and complexes connected by non-covalent interactions, such as hydrogen bonds or ionic bonds, are typically not ...
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Diisononyl Phthalate
Diisononyl phthalate (DINP) is a phthalate used as a plasticizer. DINP is typically a mixture of chemical compounds consisting of various isononyl esters of phthalic acid, and is commonly used in a large variety of plastic items. Health Issues The European Union has set a maximum specific migration limit (SML) from food contact materials of 9 mg/kg food for the sum of diisononyl phthalates and diisodecyl phthalates. DINP is listed as a substance "known to the State of California to cause cancer" under Proposition 65 legislation. Studies find that exposure to environmentally relevant concentrations of DINP in zebrafish disrupt the endocannabinoid system (ECS) and affect reproduction in a gender specific manner, and have other adverse effects on aquatic organisms, as DINP upregulates orexigenic signals and causes hepatosteatosis together with deregulation of the peripheral ECS and lipid metabolism. ECHA's Risk Assessment Committee (RAC) has concluded, on March 7, 201 ...
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Di(2-ethylhexyl) Phthalate
Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, diisooctyl phthalate, DEHP; incorrectly — dioctyl phthalate, DIOP) is an organic compound with the formula C6H4(CO2C8H17)2. DEHP is the most common member of the class of phthalates, which are used as plasticizers. It is the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colorless viscous liquid is soluble in oil, but not in water. Production Di(2-ethylhexyl) 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. It was first produced in commercial quantities in Japan around 1933 and in the United States in 1939. : As 2-ethylhexanol is produced as a racemic mixture, DEHP consists of the (''R'',''R'')- and (''S'',''S'')-diasteromers, and the '' meso''-isomer. : Use Due to its suitable properties and the low cost, DEHP is widely used as ...
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Dibutoxy Ethyl Phthalate
Dibutoxy ethyl phthalate is an organic compound and phthalate ester, baring 2-butoxyethanol groups. It is used as a plasticizer in polyvinyl chloride, polyvinyl acetate and 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 .... Like most phthalates it is non-volatile, and remains liquid over a wide range of temperatures. Although its water solubility is low, it remains one of the most water soluble of the common phthalates. References {{Reflist Phthalate esters Ethers ...
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Diisoheptyl Phthalate
Diisoheptyl phthalate is a phthalate used as a plasticizer. Diisoheptyl phthalate is typically a mixture of chemical compounds consisting of various isoheptyl esters of phthalic acid with the chemical formula C22H34O4. See also * Diisononyl phthalate Diisononyl phthalate (DINP) is a phthalate used as a plasticizer. DINP is typically a mixture of chemical compounds consisting of various isononyl esters of phthalic acid, and is commonly used in a large variety of plastic items. Health Issues ... References {{ester-stub Phthalate esters ...
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Butyl Benzyl Phthalate
Benzyl butyl phthalate (BBP) is an organic compound historically used a plasticizer, but which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and ''n''-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB. BBP was commonly used as a plasticizer for vinyl foams, which are often used as sheet vinyl flooring and tiles. Compared to other phthalates it was less volatile than dibutyl phthalate and imparted better low temperature flexibility than di(2-ethylhexyl) phthalate. BBP is classified as toxic by the European Chemical Bureau (ECB) and hence its use in Europe has declined rapidly. Structure and reactivity BBP is a diester. Since BBP contains two ester bonds it can react in a variety of chemical pathways. Both the carbonyl C-atoms are weakly electrophili ...
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Bis(2-methoxyethyl) Phthalate
Bis(2-methoxyethyl) phthalate, also commonly di(2-methoxyethyl) phthalate (DMEP), is a phthalate ester baring 2-methoxyethanol groups. Historically it was used as a plasticizer in 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 ... plastics, it is now largely banned owing to concerns over its effects to human health. References {{Reflist Phthalate esters Ethers Methoxy compounds ...
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Diisobutyl Phthalate
Diisobutyl phthalate (DIBP) is prepared by esterification process of isobutanol and phthalic anhydride. Its structural formula is C6H4(COOCH2CH(CH3)2)2. DIBP is an odorless plasticizer and has excellent heat and light stability. It is the lowest cost plasticizer for cellulose nitrate. DIBP has lower density and freezing point than the related compound dibutyl phthalate (DBP). Otherwise, it has similar properties DBP and can often be used as a substitute for it. Its refractive index is 1.488–1.492 (at 20 °C, D). Health issues The concentration of a metabolite of DIBP, monoisobutyl phthalate (MIBP), has been steadily increasing in the urine of Americans over the period 1999–2008.Center for Disease Control Fourth National Report on Human Exposure to Environmental Chemicals, Updated Tables, February 201CDC Exposure Report In 2021, DIBP, along with dextrorphan, was identified in >75% of sludge samples taken from 12 wastewater treatment plants in California. The same stud ...
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Persistent, Bioaccumulative And Toxic Substances
Persistent, bioaccumulative and toxic substances (PBTs) are a class of compounds that have high resistance to degradation from abiotic and biotic factors, high mobility in the environment and high toxicity. Because of these factors PBTs have been observed to have a high order of bioaccumulation and biomagnification, very long retention times in various media, and widespread distribution across the globe. Most PBTs in the environment are either created through industry or are unintentional byproducts.Blais J. 2005. Biogeochemistry of persistent bioaccumulative toxicants: processes affecting the transport of contaminants to remote areas. Canadian Journal of Fisheries and Aquatic Sciences 62: 236-243. History Persistent organic pollutants (POPs) were the focal point of the Stockholm Convention 2001 due to their persistence, ability to biomagnify and the threat posed to both human health and the environment. The goal of the Stockholm Convention was to determine the classification o ...
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Di-n-butyl Phthalate
Dibutyl phthalate (DBP) is an organic compound which is commonly used as a plasticizer because of its low toxicity and wide liquid range. With the chemical formula C6H4(CO2C4H9)2, it is a colorless oil, although commercial samples are often yellow.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. Production and use DBP is produced by the reaction of ''n''-butanol with phthalic anhydride. DBP is an important plasticizer that enhances the utility of some major engineering plastics, such as PVC. Such modified PVC is widely used in plumbing for carrying sewerage and other corrosive materials. Degradation Hydrolysis of DBP leads to phthalic acid and 1-butanol. Monobutyl phthalate (MBP) is its major metabolite. Biodegradation Biodegradation by microorganisms represents one route for remediation of DBP. For example, ''Ente ...
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Diethyl Phthalate
Diethyl phthalate (DEP) is a phthalate ester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water. Synthesis and applications Diethyl phthalate is produced by the reaction of ethanol with phthalic anhydride, in the presence of a strong acid catalyst: It finds some use as a specialist plasticiser in PVC, it has also been used as a blender and fixative in perfume. Biodegradation Biodegradation by microorganisms Biodegradation of DEP in soil occurs by sequential hydrolysis of the two diethyl chains of the phthalate to produce monoethyl phthalate, followed by phthalic acid. This reaction occurs very slowly in an abiotic environment. Thus there exists an alternative pathway of biodegradation which includes transesterification or demethylation by microorganisms, if the soil is also contaminated with methanol, that would produce another three intermediate comp ...
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