Plasticizers: Synthesis of phthalate esters via FeCl3-catalyzed nucleophilic addition of alcohols to phthalic anhydride

Bajracharya, Gan B.; Koju, Rashmi; Ojha, Sarbeshwar; Nayak, Sashisu; Subedi, Sabita; Sasai, Hiroaki

doi:10.1016/j.rechem.2021.100190

Cited by 5 publications

(7 citation statements)

References 15 publications

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“…Recently, a report showed that the latter reaction can be performed at lower temperatures by having FeCl 3 as the Lewis acid catalyst for esterification. This catalyst is a neutral and cheap material, enabling the production of PAEs commercially valuable [ 18 ].…”

Section: Phthalatesmentioning

confidence: 99%

Unpacking Phthalates from Obscurity in the Environment

Baneshi,

Tonney-Gagne,

Halilu

et al. 2023

Molecules

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Phthalates (PAEs) are a group of synthetic esters of phthalic acid compounds mostly used as plasticizers in plastic materials but are widely applied in most industries and products. As plasticizers in plastic materials, they are not chemically bound to the polymeric matrix and easily leach out. Logically, PAEs should be prevalent in the environment, but their prevalence, transport, fate, and effects have been largely unknown until recently. This has been attributed, inter alia, to a lack of standardized analytical procedures for identifying them in complex matrices. Nevertheless, current advancements in analytical techniques facilitate the understanding of PAEs in the environment. It is now known that they can potentially impact ecological and human health adversely, leading to their categorization as endocrine-disrupting chemicals, carcinogenic, and liver- and kidney-failure-causing agents, which has landed them among contaminants of emerging concern (CECs). Thus, this review article reports and discusses the developments and advancements in PAEs’ standard analytical methods, facilitating their emergence from obscurity. It further explores the opportunities, challenges, and limits of their advancements.

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Section: Phthalatesmentioning

confidence: 99%

Unpacking Phthalates from Obscurity in the Environment

Baneshi,

Tonney-Gagne,

Halilu

et al. 2023

Molecules

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“…The ring-closing metathesis of diallyl phthalate using the Grubb's 2nd generation catalyst led to macrolide (298) ( Scheme 114 ). 279 …”

Section: Applications Of Pa In Esterificationmentioning

confidence: 99%

Phthalic anhydride (PA): a valuable substrate in organic transformations

Nikoofar,

Sadathosainy

2023

RSC Adv.

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“…PAEs, in addition to PVC materials, allow the polymers to slide against each other, improving their flexibility, durability, and stability [6]. Chemically, PAEs are dialkyl, alkyl, or aryl esters of 1,2-benzenedicarboxylic acid synthetized from the esterification of phthalic anhydride and specific alcohols (Figure 1) [7]. Their structure consists of a planar aromatic benzene ring attached to two carboxyl group at the R and R ′ positions (Figure 2) [8].…”

Section: Introductionmentioning

confidence: 99%

“…Separations 2024, 11, 133 2 of 21 alkyl, or aryl esters of 1,2-benzenedicarboxylic acid synthetized from the esterification of phthalic anhydride and specific alcohols (Figure 1) [7]. Their structure consists of a planar aromatic benzene ring attached to two carboxyl group at the R and R′ positions (Figure 2) [8].…”

Section: Introductionmentioning

confidence: 99%

“…However, PAEs are also applied as excipients and enteric coatings on drugs to control the oral administration and release of drugs into gastrointestinal tract. Guidelines published by the European Medicines Agency (EMA) and alkyl, or aryl esters of 1,2-benzenedicarboxylic acid synthetized from the esterificatio phthalic anhydride and specific alcohols (Figure 1) [7]. Their structure consists of a pl aromatic benzene ring attached to two carboxyl group at the R and R′ positions (Figu [8].…”

Section: Introductionmentioning

confidence: 99%

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Phthalates: The Main Issue in Quality Control in the Beverage Industry

Iannone,

Di Fiore,

Carriera

et al. 2024

Separations

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Phthalate esters (PAEs) are a group of chemicals used to improve the flexibility and durability of plastics. The chemical properties and the resistance to high temperatures promote their degradation and release into the environment. Food and beverages can be contaminated by PAEs through the migration from packaging material because they are not covalently bound to plastic and also via different kinds of environmental sources or during processing. For instance, alcoholic drinks in plastic containers are a particular risk, since the ethanol contained provides a good solubility for PAEs. According to its role as an endocrine disruptor compound and its adverse effects on the liver, kidney, and reproductive and respiratory systems, the International Agency on Research Cancer (IARC) classified di-(2-ethylhexyl) phthalate (DEHP) as a possible human carcinogen. For this reason, to control human exposure to PAEs, many countries prohibited their use in food as non-food substances. For example, in Europe, the Commission Regulation (EU) 2018/2005 restricts the use of DEHP, dibutyl phthalate (DBP), benzyl butyl phthalate (BBP), and diisobutyl phthalate (DiBP) to a concentration equal to or below 0.1 by weight in plasticizers in articles used by consumers or in indoor areas. There are reports from the US Food and Drug Administration (FDA) that some beverages (and food as well), particularly fruit juices, contain high levels of phthalates. In some cases, the deliberate adulteration of soft drinks with phthalate esters has been reported. This paper would like to show the difficulties of performing PAE analysis in beverage matrices, in particular alcoholic beverages, as well as the main solutions provided for quality control in the industrial branches.

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Plasticizers: Synthesis of phthalate esters via FeCl3-catalyzed nucleophilic addition of alcohols to phthalic anhydride

Cited by 5 publications

References 15 publications

Unpacking Phthalates from Obscurity in the Environment

Unpacking Phthalates from Obscurity in the Environment

Phthalic anhydride (PA): a valuable substrate in organic transformations

Phthalates: The Main Issue in Quality Control in the Beverage Industry

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