Characterization of 1,5‐pentanediol dibenzoate as a potential “green” plasticizer for poly(vinyl chloride)

Firlotte, Nicolas; Cooper, David G.; Marić, Milan; Nicell, Jim A.

doi:10.1002/vnl.20181

Cited by 34 publications

(46 citation statements)

References 27 publications

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“…These alternative plasticizers were selected for leaching tests based on their ability to lower the glass-transition temperature of PVC, as well as for their plasticization, biodegradation and mechanical testing results which have been shown to be comparable to that of DEHP (Erythropel et. al, 2012;Firlotte et al, 2009). …”

Section: Plasticizersmentioning

confidence: 97%

“…Many alternatives have been proposed but not all combine the desirable properties required of the plasticizer during use and after disposal. Our group has investigated the synthesis and design of alternative PVC plasticizers (Erythropel et al, 2012), the biodegradation of alternative plasticizers , as well as the polymer processing and mechanical properties of alternative plasticizers in PVC (Firlotte et al, 2009). The ideal alternative to DEHP must satisfy many criteria but one crucial criterion is to minimize the plasticizer leaching rate from PVC mixtures into the environment.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Aqueous leaching of di-2-ethylhexyl phthalate and “green” plasticizers from poly(vinyl chloride)

Kastner

Cooper

Marić

et al. 2012

Science of The Total Environment

Self Cite

103

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Section: Plasticizersmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Aqueous leaching of di-2-ethylhexyl phthalate and “green” plasticizers from poly(vinyl chloride)

Kastner

Cooper

Marić

et al. 2012

Science of The Total Environment

Self Cite

103

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“…To tackle the problems arising from the widespread use of DEHP, recent research aims at producing equally effective plasticizers that are more biodegradable and less toxic than DEHP and would thus be eliminated more quickly in the environment, an idea that can also be extended to the metabolites of this plasticizer (Erythropel et al 2013;Erythropel et al 2012;Firlotte et al 2009;Pour et al 2009a;Pour et al 2009b;Shi et al 2011;Stuart et al 2010). There also exist many commercial efforts to create plasticizers that are less toxic and recalcitrant; however, formulations of these compounds are often unknown.…”

Section: Perspectivesmentioning

confidence: 99%

Leaching of the plasticizer di(2-ethylhexyl)phthalate (DEHP) from plastic containers and the question of human exposure

Erythropel

Marić

Nicell

et al. 2014

Appl Microbiol Biotechnol

346

182

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Di(2-ethylhexyl)phthalate (DEHP) is a widely used plasticizer to render poly(vinyl chloride) (PVC) soft and malleable. Plasticized PVC is used in hospital equipment, food wrapping, and numerous other commercial and industrial products. Unfortunately, plasticizers can migrate within the material and leach out of it over time, ending up in the environment and, frequently, the human body. DEHP has come under increased scrutiny as its breakdown products are believed to be endocrine disruptors and more toxic than DEHP itself. DEHP and its breakdown products have been identified as ubiquitous environmental contaminants, and daily human exposure is estimated to be in the microgram per kilogram level. The objective of this review is to summarize and comment on published sources of DEHP exposure and to give an overview of its environmental fate. Exposure through bottled water was examined specifically, as this concern is raised frequently, yet only little exposure to DEHP occurs through bottled water, and DEHP exposure is unlikely to stem from the packaging material itself. Packaged food was also examined and showed higher levels of DEHP contamination compared to bottled water. Exposure to DEHP also occurs in hospital environments, where DEHP leaches directly into liquids that passed through PVC/DEHP tubing and equipment. The latter exposure is at considerably higher levels compared to food and bottled water, specifically putting patients with chronic illnesses at risk. Overall, levels of DEHP in food and bottled water were below current tolerable daily intake (TDI) values. However, our understanding of the risks of DEHP exposure is still evolving. Given the prevalence of DEHP in our atmosphere and environment, and the uncertainty revolving around it, the precautionary principle would suggest its phaseout and replacement. Increased efforts to develop viable replacement compounds, which necessarily includes rigorous leaching, toxicity, and impact assessment studies, are needed before alternative plasticizers can be adopted as viable replacements.

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“…Di(ethylene glycol)dibenzoate and di(propylene glycol)dibenzoate were shown to form toxic, stable metabolites when treated with yeast [55]. The related chemical 1,5-pentanediol dibenzoate shows improved biodegradability [56]. The outlook is promising, but it was reported that a technical-grade plasticizer containing predominantly di(propylene glycol) dibenzoate showed estrogenic properties [47], so more thorough testing is needed.…”

Section: E S Beach Et Almentioning

confidence: 99%

Plastics additives and green chemistry

Beach

Weeks

Stern

et al. 2013

Pure and Applied Chemistry

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The plastics enterprise depends on a small number of commodity polymers to perform in diverse applications, requiring additives to produce desired properties and performance. Toxic effects and environmental persistence of certain additive chemicals impact the sustainability of the industry. Green chemistry has been and will continue to be applied to find solutions to these issues. This review focuses on alternatives to phthalate plasticizers and halogenated flame retardants, two categories that together account for a significant portion of the global additives market and the global dispersion of endocrine-disrupting chemicals. Small-molecule alternatives that exist in various stages of research and commercialization will be discussed, with emphasis on the use of renewable resources. The rise of biorefineries and new bio-based monomers may help overcome existing economic barriers to adoption of alternatives. Increasing the molecular weight of additives or covalently linking them to polymer backbones are two promising strategies for reducing both mobility and toxicity that will also be discussed. Finally, the design of new polymers that show desirable properties without the use of additives will be considered. The substances put forward as "green" alternatives have yet to receive the same level of scrutiny as diethylhexyl phthalate (DEHP, also known as dioctyl phthalate) or polybrominated diphenyl ethers (PBDEs). Cooperation between chemists, engineers, and the environmental health community will be critical to ensure the safety and sustainability of new technologies. Phthalate plasticizers: Occurrence and toxicityPhthalates are diesters of 1,2-benzenedicarboxylic acids (phthalic acids) with chemical characteristics that depend on the nature of the side-chains [5]. Since phthalate additives in plastic are not covalently linked to the host polymer, they can leach into the environment [6]. Although they are generally nonpersistent, contamination in the environment is still significant due to widespread use; low-and highmolecular-weight phthalates are commonly found in household dust, soil, and indoor and outdoor air, and as detectable residues in foods [5]. Phthalate exposures may occur through ingestion, inhalation, dermal absorption, and parenteral administration [7]. Several studies have shown that some phthalates possess endocrine-disrupting effects in male rat offspring, following in utero or lactational exposure, which manifest as hypospadias, cryptorchidism, testicular cancer, decreased testosterone levels, and reduced semen quality [5]. Phthalate activation of peroxisome proliferator-activated receptors alpha and gamma (PPARα and PPARγ), adjuvant activity, induction of cell proliferation, suppression of apoptosis, oxidative DNA damage, and production of reactive oxygen species (ROS) have been implicated as well [8][9][10][11]. It has been proposed that oral exposure in rats and humans allows diethylhexyl phthalate (DEHP) to enter the gastrointestinal tract, where it is rapidly metabolized to mono-(2-methylhex...

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Characterization of 1,5‐pentanediol dibenzoate as a potential “green” plasticizer for poly(vinyl chloride)

Cited by 34 publications

References 27 publications

Aqueous leaching of di-2-ethylhexyl phthalate and “green” plasticizers from poly(vinyl chloride)

Aqueous leaching of di-2-ethylhexyl phthalate and “green” plasticizers from poly(vinyl chloride)

Leaching of the plasticizer di(2-ethylhexyl)phthalate (DEHP) from plastic containers and the question of human exposure

Plastics additives and green chemistry

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