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A Review of the Environmental Degradation, Ecotoxicity, and Bioaccumulation Potential of the Low Molecular Weight Polyether Polyol Substances

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Reviews of Environmental Contamination and Toxicology Volume 244

Part of the book series: Reviews of Environmental Contamination and Toxicology ((RECT,volume 244))

Abstract

“Polyalkylene glycol” is the name given to a broad class of synthetic organic chemicals which are produced by polymerization of one or more alkylene oxide (epoxide) monomers, such as ethylene oxide (EO) and propylene oxide (PO), with various initiator substances which possess amine or alcohol groups. A generalization of this polymerization reaction is illustrated in Fig. 1.

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Abbreviations

DEG:

Diethylene glycol; 2,2′-oxy-diethanol

EO:

Ethylene oxide; oxirane

GLY:

Glycerol; propane-1,2,3-triol

MPG:

Mono-propylene glycol; propane-1,2-diol

NTE:

2,2′,2″-Nitrilotriethanol; triethanol amine

o-TDA:

Methyl-phenylene-2,3-diamine and methyl-phenylene-3,4-diamine, mixture of isomers

PEC:

Predicted environmental concentration

PEG:

Polyethylene glycol

PENT:

Pentaerythritol; 2,2-bis(hydroxymethyl)propane-1,3-diol

PNEC:

Predicted no-effect concentration

PO:

Propylene oxide; methyloxirane

SOR:

Sorbitol; glucitol; 1,2,3,4,5,6-hexahydroxy-cyclohexane

SUC:

Sucrose; α,β-1,4-gluco-fructopyranose

TMP:

1,1,1-Trimethylolpropane; propylidyne-1,1,1-trimethanol

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Acknowledgement

The authors are grateful to Monika Leutbecher of Covestro Deutschland AG, Gitta Egbers of BASF Polyurethanes GmbH and Joerg Palmersheim, European Isocyanate and Polyols Producer Association (ISOPA) for their contributions to the discussion, and to Yunzhou Chai for performing the OASIS metabolism predictions. The authors gratefully acknowledge the many significant contributions of Dr. Urs Friederich (formerly Dow Europe GmbH) to the early development and drafting of this review. The authors are grateful to ISOPA for financial support. Views and opinions expressed in this paper are those of the authors and not necessarily of ISOPA.

Conflict of Interest

T. Schupp worked for BASF, a Polyether-polyol producer, until 2012.

B.T.A. Bossuyt is working for Huntsman, a Polyether-polyol producer.

R.J. West and S.M. Shen are working for Dow Chemical Company, a Polyether-polyol producer.

T. Austin and C.V. Eadsforth are working for Shell Chemical Company, a Polyether-polyol producer.

This work was sponsored by ISOPA, the European Isocyanate, and Polyol Producer Association. The authors declare that all data of the PEPOs available to them are evaluated and presented in good faith. The views presented are those of the authors and do not necessarily coincide with the views of ISOPA.

Author information

Authors and Affiliations

  1. Faculty of Chemical Engineering, Muenster University of Applied Science, Stegerwaldstrasse 39, Steinfurt, 48565, Germany

    Thomas Schupp

  2. Shell Health, Brabazon House, Concord Business Park, Threapwood Road, Manchester, M22 0RR, UK

    Tom Austin & Charles V. Eadsforth

  3. Global Product EHS Department, Huntsman Europe, Everslaan 45, Everberg, 3078, Belgium

    Bart Bossuyt

  4. The Dow Chemical Company, Shanghai, People’s Republic of China

    Summer M. Shen

  5. Toxicology and Environmental Research and Consulting, The Dow Chemical Company, 1803 Building, Washington Street, Midland, MI, 48674, USA

    Robert J. West

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  1. Thomas Schupp
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  2. Tom Austin
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  4. Bart Bossuyt
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Corresponding author

Correspondence to Thomas Schupp .

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  1. Reviews of Environmental Contamination and Toxicology, University of Amsterdam, Amsterdam, The Netherlands

    Pim de Voogt

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Appendices

Appendix 1: Toxicity to Fish; 96 h LC50

Composition

CAS-no.

Mn (g/mol)

Species

Value

TMP + PO

50586-59-9

340

Danio rerio

>100 mg/L

SUC + GLY + PO

9049-71-2

720

Pimephales promelas

27.2 g/L

SUC + PO

9049-71-2

440

Danio rerio

>4.2, <7.5 g/L

EDA + PO

25214-63-5

360

Danio rerio

>3.1, <7.5 g/L

EDA + PO

25214-63-5

480

Leuciscus idus

4.6 g/L

EDA + EO + PO

26316-40-5

280

Danio rerio

>100 mg/L

EDA + EO + PO

26316-40-5

280

Pimephales promelas

4.23 g/L

GLY + PO

25791-96-2

300

Leuciscus idus

>1 g/L

SOR + PO

52625-13-5

700

Leuciscus idus

>1 g/L

o-TDA + PO

63641-63-4

340

Danio rerio

>77 mg/L (LC0)

MPG + PO

25322-69-4

230

Danio rerio

>100 mg/L (LC0)

MPG + PO

25322-69-4

400

Poecelia reticulata

>100 mg/L (LC0)

MPG + PO

25322-69-4

450

Leuciscus idus

>4.6, <10 g/L

PENT + PO

9051-49-4

420

Danio rerio

>100 mg/L (LC0)

NTE + PO

37208-53-0

320

Danio rerio

>100 mg/L (LC0)

DEG + PO

9051-51-8

280

Danio rerio

>100 mg/L (LC0)

Appendix 2: Acute Toxicity to Crustacea (48 h EC50)

Composition

CAS-No.

Mn (g/mol)

Species

Value

TMP + PO

50586-59-9

340

Daphnia magna

>100 mg/L (EC0)

SUC + PO

9049-71-2

440

Daphnia magna

>100 mg/L (EC0)

SUC + GLY + PO

9049-71-2

720

Daphnia magna

9.89 g/L

EDA + PO

25214-63-5

360

Daphnia magna

>100 mg/L (EC0)

EDA + EO + PO

26316-40-5

280

Daphnia magna

>100 mg/L (EC0)

EDA + EO + PO

26316-40-5

280

Daphnia magna

305a and 103b mg/L

GLY + PO

25791-96-2

300

Daphnia magna

>100 mg/L (EC0)

SOR + PO

52625-13-5

700

Daphnia magna

>100 mg/L (EC0)

SOR + PO

52625-13-5

600

Acartia tonsa

>1000 mg/L (EC10)

o-TDA + PO

63641-63-4

340

Daphnia magna

>100 mg/L (EC0)

o-TDA + PO + EO

67800-94-6

520

Daphnia magna

>100 mg/L (EC0)

MPG + PO

25322-69-4

230

Daphnia magna

105 mg/L

PENT + PO

9051-49-4

420

Daphnia magna

>100 mg/L (EC0)

NTE + PO

37208-53-0

320

Daphnia magna

>100 mg/L (EC0)

DEG + PO

9051-51-8

280

Daphnia magna

>100 mg/L (EC0)

GLY + EO

31694-55-0

310

Daphnia magna

>100 mg/L (EC0)

  1. aNon-neutralized
  2. bNeutralized

Appendix 3: Toxicity to Algae (72 h)

Composition

CAS-No.

Mn (g/mol)

Species

ErC50 (mg/L)

NOECr (mg/L)

TMP + PO

50586-59-9

340

Desmodesmus subspicatus

>100

≥100

SUC + PO

9049-71-2

580

Desmodesmus subspicatus

>100

100

EDA + EO + PO

26316-40-5

280

Desmodesmus subspicatus

>100

100

GLY + PO

25791-96-2

300

Desmodesmus subspicatus

>100

100

SOR + PO

52625-13-5

600

Skeletonema costatum

>1000

1000

o-TDA + PO

63641-63-4

340

Desmodesmus subspicatus

>100

100

MPG + PO

25322-69-4

230

Desmodesmus subspicatus

>100

100

PENT + PO

9051-49-4

420

Desmodesmus subspicatus

>100

100

NTE + PO

37208-53-0

320

Desmodesmus subspicatus

>100

100

DEG + PO

9051-51-8

280

Desmodesmus subspicatus

>100

100

Appendix 4: Toxicity to Microorganisms

Composition

CAS-no.

Mn (g/mol)

Test

Value

TMP + PO

50586-59-9

340

Resp. inhib. activated sludge (OECD 209)

IC50/30 min > 10 g/L

SUC + PO

9049-71-2

500

Resp. inhib. activated sludge (OECD 209)

IC50/30 min > 0.72 g/L

EDA + PO

25214-63-5

360

Resp. inhib. activated sludge (OECD 209)

IC50 > 10 g/L (IC10)

EDA + EO + PO

26316-40-5

280

Resp. inhib. activated sludge (OECD 209)

IC50 > 10 g/L (IC10)

GLY + PO

25791-96-2

300

Resp. inhib. activated sludge (OECD 209)

IC50 > 10 g/L (IC0)

GLY + PO

25791-96-2

300

Pseudomonas putida growth inhibitiona)

LOEC = 6.6 g/L

SOR + PO

52625-13-5

600

Resp. inhib. activated sludge (OECD 209)

IC50 > 10 g/L (IC0)

SOR + PO

52625-13-5

700

Pseudomonas putida growth inhibitiona

LOEC = 2.4 g/L

o-TDA + PO

63641-63-4

340

Resp. inhib. activated sludge (OECD 209)

IC50 = 10 g/L

o-TDA + PO + EO

67800-94-6

520

Resp. inhib. activated sludge (OECD 209)

IC50 > 2 g/L (IC0)

MPG + PO

25322-69-4

230

Resp. inhib. activated sludge (OECD 209)

IC50 > 1 g/L (IC0)

MPG + PO

25322-69-4

450

Resp. inhib. activated sludge (OECD 209)

IC50 > 700 mg/L (IC0)

MPG + PO

25322-69-4

450

Pseudomonas putida growth inhibitiona)

LOAEC > 10 g/L (IC0)

PENT + PO

9051-49-4

420

Resp. inhib. activated sludge (OECD 209)

IC50 > 10 g/L (IC5)

NTE + PO

37208-53-0

320

Resp. inhib. activated sludge (OECD 209)

IC50 > 10 g/L (IC0)

DEG + PO

9051-51-8

280

Resp. inhib. activated sludge (OECD 209)

IC50 > 1 g/L (IC0)

GLY + EO

31694-55-0

310

Resp. inhib. activated sludge (OECD 209)

IC50 > 640 mg/L (IC10)

  1. Water quality—Pseudomonas putida growth inhibition test (Pseudomonas cell multiplication inhibition test). https://www.iso.org/obp/ui/#iso:std:iso:10712:ed-1:v1:en. Accessed at: June 23rd, 2016
  2. aGerman Umweltbundesamt: “Bewertung wassergefaehrdender Stoffe, LTwS Nr. 10, 1979.” See also: ISO 10712:1995(en)

Appendix 5: Metabolic Transformation of EDA + PO + EO, Modeled with OASIS®

1.1 Prediction of Biodegradation Metabolites of Polyols

Objective: The objective of this study is to identify potential metabolites from aerobic biodegradation of propoxylated/ethoxylated ethylenediamine polyol (EDA + EO + PO, CAS No. 26316-40-5), sorbitol propoxylated polyol (SOR + PO, CAS No. 52625-13-5), and propoxylated o-diaminotoluene (TDA + PO, CAS No. 63641-63-4) using prediction software.

Software: Prediction software OASIS Catalogic (v5.11.16) was selected. The Kinetic 301F Model (v12.15) implemented in OASIS Catalogic was deemed appropriate for this study. The model was developed based on a training database of catabolic pathways for more than 551 organic compounds. Training set data and expert knowledge were used to determine the principal transformations and to train the system to simulate aerobic catabolism of training chemicals. The documented pathways of microbial catabolism were collected from scientific papers, monographs, and databases accessible over the Internet.

Method: Seven representative molecular structures of these polyols (Tables 18–20) representing various alkoxylation configurations were used for the prediction of their potential metabolites from aerobic biodegradation. The seven molecular structures included three variations from EDA + EO + PO (Table 18), two variations from SOR + PO (Table 19), and two variations from TDA + PO (Table 20). These seven representative molecular structures are in the applicability domain of the model defined by its parametric domain, structure fragment domain, and metabolic domain. Potential metabolites from aerobic biodegradation of the seven molecular structures were predicted using Kinetic 301F Model in OASIS Catalogic (v5.11.16). The metabolites with a predicted quantity of greater than or equal to 5 % (i.e., 0.05) were reported in this study.

Results: Potential metabolites from aerobic biodegradation of the seven representative molecular structures of the polyols are summarized in Tables 21–27. Predicted quantities, octanol-water partition coefficient (logKow) values, and the predicted mode-of-action (predicted using the Verhaar Scheme (modified) and OASIS®) of the potential metabolites as well as their parent compounds are also shown in Tables 21–28. Predicted metabolites have logKow values similar or less than their corresponding parent compounds. As far as the ecotoxicity and bioaccumulation potential of these polyols and their metabolites correlate with their logKow, the metabolites are not expected to be more toxic or more bioaccumulative than their parent compounds. However, it cannot be excluded that EDA and TDA-based PEPOs might release the core substance (initiator), which shows a higher ecotoxicity than the respective PEPO. Additionally, after mode of action prediction, a number of the metabolites fall into the categories “Reactive unspecified” or “Narcotic amine”; compounds that fall into these categories are expected to exert toxicity greater than expected via non-polar narcosis.

Conclusion: Predicted metabolites have logKow values similar or less than their corresponding parent compounds. The bioaccumulation potential of these polyols and their metabolites correlate with their logKow, therefore, the metabolites are not expected to be more bioaccumulative than their parent compounds although some metabolites appear to be generally more reactive and may have higher aquatic toxicity.

Appendix 6: QPRFs of the Seven Representative Molecular Structures

Table 18 Representative structures for propoxylated/ethoxylated ethylenediamine polyol (EDA + EO + PO)
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Table 19 Representative structures for sorbitol propoxylated polyol (SOR + PO)
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Table 20 Representative structures for propoxylated o-diaminotoluene (TDA + PO)
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Table 21 Predicted quantities and logKow values for metabolites of EDA + 1EO + 2PO
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Table 22 Predicted quantities and logKow values for metabolites of EDA + 2EO + 4PO (a)
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Table 23 Predicted quantities and logKow values for metabolites of EDA + 2EO + 4PO (b)
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Table 24 Predicted quantities and logKow values for metabolites of SOR + 6PO (a)
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Table 25 Predicted quantities and logKow values for metabolites of SOR + 6PO (b)
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Table 26 Predicted quantities and logKow values for metabolites of TDA + 3PO (a)
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Table 27 Predicted quantities and logKow values for metabolites of TDA + 3PO (b)
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Table 28 Metabolite mode of action as predicted by the Verhaar scheme (modified) and OASIS®
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Schupp, T., Austin, T., Eadsforth, C.V., Bossuyt, B., Shen, S.M., West, R.J. (2017). A Review of the Environmental Degradation, Ecotoxicity, and Bioaccumulation Potential of the Low Molecular Weight Polyether Polyol Substances. In: de Voogt, P. (eds) Reviews of Environmental Contamination and Toxicology Volume 244. Reviews of Environmental Contamination and Toxicology, vol 244. Springer, Cham. https://doi.org/10.1007/398_2017_2

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