Chemical conversion of poly(carbonate) to 1,3-dimethyl-2-imidazolidinone (DMI) and bisphenol A: a practical approach to the chemical recycling of plastic wastes

Hata, Sohei; Goto, Hidekazu; Yamada, E.; Oku, Akira

doi:10.1016/s0032-3861(01)00800-x

Cited by 82 publications

(62 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Hata et al 52 investigated the solvolytic recycling of PC with N,N¢-dimethyl-1,2-diaminoethane into BPA and 1,3-dimethylimidazolidin-2-one (Scheme 11b). This method proceeded with a very high conversion of almost 100 wt% at temperatures lower than 100 1C for 30 min.…”

Section: Chemical Recycling Of Pet and Its Relativesmentioning

confidence: 99%

Development of materials and technologies for control of polymer recycling

Nishida

2011

Polym J

View full text Add to dashboard Cite

The movement toward a recycling-based society through the essential development of recyclable materials alongside technologies for controlling recycling is reviewed. Recently, there has been progress in producing various polymers and technologies with the aim of achieving circulative utilization. For example, the upgrade recycling of commodity plastics, selective transformation of engineering plastics, selective depolymerization of various polymers in supercritical fluids, crosslinking-decrosslinking control using reversible reactions and developments in biomass-based recyclable polymers. Despite great strides taken in the effectiveness, efficiency and precision of these polymers and technologies, further improvements will be required to meet the practical requirements of a responsible sustainable system for the recycling of containers, packages, electric household appliances and end-of-life vehicles all of which are operated in compliance with the recycling laws of Japan.

show abstract

Section: Chemical Recycling Of Pet and Its Relativesmentioning

confidence: 99%

Development of materials and technologies for control of polymer recycling

Nishida

2011

Polym J

View full text Add to dashboard Cite

show abstract

“…Therefore, it can be considered as normal that amines are constantly in contact with PC baby bottles (as well as other PC materials). The use of amines has already been studied as a possible way to recycle plastics, because PC can be degraded by aminolysis, resulting in the release of BPA (Hata, Goto, Yamada, & Oku, 2002). In this paper, several substances, including amines and amides, are assayed in order to find out which of them induce a higher BPA release from PC.…”

Section: Introductionmentioning

confidence: 99%

Effect of amines in the release of bisphenol A from polycarbonate baby bottles

Maia

Cruz

Sendón

et al. 2010

Food Research International

View full text Add to dashboard Cite

a b s t r a c tThe key block for the production of polycarbonate (PC) is bisphenol A (BPA). Recent studies have proven that this monomer is able to migrate from PC baby bottles into food simulants and, although this is a polemical subject, numerous investigations indicate that BPA may have an effect on the human health. For these reasons, BPA safety regarding human exposure has recently become an alarming issue.Amines are a class of chemicals which are present in foodstuffs, such as milk. For this reason PC baby bottles, while being used, are continuously in contact with several amines, some of which are able to cause PC aminolysis, resulting in the release of BPA.In this work, 16 substances (14 with amine groups and 2 with amide groups) were tested in order to verify if they were able to increase BPA release by increasing PC depolymerization. High-performance liquid chromatography (HPLC) with fluorescence detection (FLD) and gas chromatography coupled to mass spectrometry (GC-MS) were used to quantify and identify the BPA, respectively. Although most of the substances tested did not increase the release of BPA from PC, some of them had a significant effect and high levels of this monomer were measured in the solutions. Of all of the amines tested that originating the worst case of BPA release was 1,4-diaminobutane. Also known as putrescine, 1,4-diaminobutane is a biogenic amine that results from protein degradation and it may be present in milk. In this case, BPA concentration in the solution was more than 5000 times the level found in the control sample.

show abstract

“…In view of this change in manufacturing method, it is clear that the recycling technology for PC must be synchronized with the manufacturing technology to achieve the highest atom economy, i.e., the carbonate unit of PC must be recycled as the counterpart monomer of BPA. [2][3][4][5][6] Thus, with reproduced BPA and carbonate such as diaryl or dialkyl carbonate, the chemical recycling of PC fi nally composes a closed circuit.…”

Section: Introductionmentioning

confidence: 99%

“…In a previous study, we examined the low-temperature CRAC of PC for coproducing BPA and organic carbonates without losing any chemical components. [2][3][4][5][6] In the present study, along the same conceptual lines, we chose carbohydrates (CHs) as biomass-based polyols, in expectation of their solvolytic behavior, as the reservoir of the carbonyl unit of PC. Among typical carbohydrates, we chose glycerol (Gly) initially and then glucose (Glu) (Figs.…”

Section: Introductionmentioning

confidence: 99%

Viable chemical recycling of poly(carbonate) as a phosgene equivalent illustrated by the coproduction of bisphenol A and carbohydrate carbonates

Hidaka

Iwakawa

Maoka

et al. 2009

J Mater Cycles Waste Manag

Self Cite

View full text Add to dashboard Cite

Chemical recycling of waste poly(carbonate) (PC) to coproduce bisphenol A (BPA) and carbohydrate carbonates was studied by selecting glycerol (Gly) and glucose (Glu) as model carbohydrates (CHs). In advance of the reaction of PC with CHs, reactions with diphenyl carbonate were examined as a model PC. In dioxane at 100°C using NaOH as catalyst, Gly was converted to cyclic carbonate hydroxymethyldioxolane (HMDO) at 98% and Glu was converted to the dicarbonate (Glu-DC) at 46%, in pyridine, in addition to the production of phenol. Similar treatment of PC with Gly using KOH as a catalyst produced HMDO and BPA at very high yields and treatment with Glu produced Glu-DC and BPA in 38%-42% yields.Key words Chemical recycling of poly(carbonate) · Carbonate of glycerol · Carbonate of glucose · Bisphenol A J Mater Cycles Waste Manag (

show abstract

Chemical conversion of poly(carbonate) to 1,3-dimethyl-2-imidazolidinone (DMI) and bisphenol A: a practical approach to the chemical recycling of plastic wastes

Cited by 82 publications

References 20 publications

Development of materials and technologies for control of polymer recycling

Development of materials and technologies for control of polymer recycling

Effect of amines in the release of bisphenol A from polycarbonate baby bottles

Viable chemical recycling of poly(carbonate) as a phosgene equivalent illustrated by the coproduction of bisphenol A and carbohydrate carbonates

Contact Info

Product

Resources

About