Abstract
Methylene-4,4′-dianiline (MDA, CAS-No. 101–77-9) is a high production volume intermediate that is mainly processed to diisocyanates and finally polyurethanes. This review summarizes available data concerning the environmental behavior. When released into the environment, MDA distributes into water and subsequently sediment and soil compartments; the air is of little relevance, owed to the low vapor pressure and short atmospheric half-life, which renders MDA non-critical for long-range transport. Biodegradation data present a diverged picture; in some tests, MDA is not readily biodegradable or even not inherent biodegradable; in other tests, MDA turned out to be readily biodegradable (but failing the 10-d window). The history and composition of the inoculum used for testing seem to play an important role, which is underlined by good test results with adapted inoculum. In soil, initially a rapid mineralization is observed, which slows down within the first days due to competitive chemical absorption. The latter results in degradation rates comparable to that of natural organic matter. Under anaerobic conditions, mineralization is poor. Irreversible chemisorption occurs unless soils/sediments are highly reduced. Half-lives due to primary decay do not indicate MDA to be persistent according to the regulatory guidance used in then EU, Canada, or the USA; in Japan, however, due to test results in MITI degradation tests, MDA would be regarded as persistent. The identification of microbial MDA metabolites deserves further research. MDA is not bioaccumulative, but it is toxic to aquatic organisms and mammals. MDA in pore water of soils is rapidly adsorbed on the surface of plant roots. Test runs were too short to draw a final conclusion with regards to transport to stem, leaves, and fruits. Data from structurally similar compounds indicate that such transport would account for less than 1% of the root-adsorbed material.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Alport DC, Gilbert DS, Outterside SM (eds) (2003) MDI and TDI: safety, health, and the environment – a source book and practical guide. Wiley, West Sussex
BASF (1981) Biologische Eliminierbarkeit im Zahn-Wellens-Test. BASF-SE, Experimental Toxicology and Ecology, Report No. 87/0892. Robust summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Baumann W (1985) Report on the test for ready biodegradability of TK10504 in the modified Sturm test (OECD Guideline No. 301B, Paris 1981). Ciba-Geigy Ltd, Basel, report R-1066.K.247; project no. 850729. 12.09.1985. Robust summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Baumann W (1986) Report on the bioelimination test on TK 10504 in the simulation test – aerobic sewage OECD Coupled Units Test No. 303 A. Ciba-Geigy Ltd, Basel. Project-no. 860630. Archive R-1066.K2.47. 15.10.1986. Robust summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Becker KH, Bastian V, Klein T (1988) The reaction of OH radicals with toluene diisocyanate, toluenediamine and methylenedianiline under simulated atmospheric conditions. J Photochem Photobiol A Chem 45:195–205
Bollag J-M, Minard RD, Liu S-Y (1983) Cross-linkage between anilines and phenolic humus constituents. Environ Sci Technol 17:72–80
Bollag J-M, Myers CJ, Minard RD (1992) Biological and chemical interactions of pesticides with soil organic matter. Sci Total Environ 123/124:205–217
Bongartz R (2012) MDA: uptake by plants in a hydroponic culture. III Report No. 11635. International Isocyanate Institute, Manchester. Robust summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Briggs GG, Olgivie SY (1971) Metabolism of 3-chloro-4-methoxyaniline and some N-acyl derivatives in soil. Pest Sci 2:165–168
Burge WD (1972) Microbial populations hydrolyzing propanil and accumulation of 3,4-dichloroaniline and 3,3′,4,4′-tetrachloro-azobenzene in soil. Soil Biol Biochem 4:379–386
Campbell K (2017) [14C]-methylenedianiline: generation of transformation products in aerobic aquatic sediment systems for identification by LC-MS/MS. Unpublished Report No. 11688 of the International Isocyanates Institute, Boonton
Carvajal-Diaz J (2015) IHS chemical economics handbook: aniline. IHS, Englewood
Caspers N, Hamburger B, Kanne R, Klebert W (1986) Ecotoxicity of toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), toluene diamine (TDA), diphenylmethanediamine (MDA). III Report No. 10417. International Isocyanate Institute, Manchester. Available from: British Library Document Supply Centre, Boston Spa, Wetherby, West Yorks. Robust summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
CITI (1992) 4-Methylphenylene-1,3-diamine (CAS-No. 95-80-7) & 4,4′-diaminodiphenylmethane (CAS-No. 101-77-8) [Acute toxicity, biodegradability and bioaccumulation data]. In: Biodegradation and bioaccumulation data of existing chemicals based on the CSCL Japan. Chemical Inspection and Testing Institute Japan, Japan Chemical Industry Ecology-Toxicology and Information Center, Tokyo, pp 3–24, 4–6. ISBN 4-89074-101-1
Cowen WF, Gastinger AM, Spanier CE, Buckel JR, Bailey RE (1996) Sorption and microbial degradation of toluene diamines and methylene dianiline in soil under aerobic and anaerobic conditions. III Report No. 11230. International Isocyanate Institute, Manchester. Robust summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Cowen WF, Gastinger AM, Spanier CE, Buckel JR (1998) Sorption and microbial degradation of toluenediamines and methylendianiline in soil under aerobic and anaerobic conditions. Environ Sci Technol 1998;32:598–603
Deng Y, Xu L, Sun X, Cheng L, Liu G (2015) Measurement and correlation of the solubility for 4,4′-diaminodiphenylmethane in different solvents. J Chem Eng Data 2015;60(7):2028–2034
ECHA (2014a) 4,4′-Methylenedianiline [REACh Dossier]. European Chemicals Agency, Helsinki. https://echa.europa.eu/de/registration-dossier/-/registered-dossier/15201. Accessed 21 June 2014
ECHA (2014b) Formaldehyde, oligomeric reaction products with aniline [REACH Dossier]. European Chemicals Agency, Helsinki. https://echa.europa.eu/de/registration-dossier/-/registered-dossier/14114. Accessed 21 June 2014
Ekici P, Leupold G, Parlar H (2001a) Degradability of selected azo dye metabolites in activated sludge systems. Chemosphere 44:721–728
Ekici P, Angerhoefer D, Parlar H (2001b) Photoinduced reactions of selected azo dye metabolites in water. Fresenius Environ Bull 10(3):245–256
European Union (2001) European Union risk assessment report, 4,4′-methylenedianiline, CAS-No. 101-77-9, EINECS-No. 202-974-4. Office for Official Publications of the European Union, Luxembourg. ISBN: 92-894-0484-1
European Union (2016) Joint Research Center: the European Union System for the Evaluation of Substances (EUSES). https://ec.europa.eu/jrc/en/scientific-tool/european-union-system-evaluation-substances. Accessed 29 Dec 2016
Frank R, Kloepffer W (1988) Spectral solar photon irradiation in Central Europa and the adjacent North Sea. Chemosphere 17(5):985–994
Government of Canada (2014) Draft screening assessment for methylenediphenyl diisocyanates and methylenediphenyl diamines, August 2014. Government of Canada, Chemicals Management Plan Division, Gatineau. http://www.chemicalsubstanceschimiques.gc.ca/group/diisocyanate-eng.php
Graveel JG, Sommers LE, Nelson DW (1985) Sites of benzidine, α-naphthylamine and p-toluidine retention in soil. Environ Toxicol Chem 4: 607–613
Han X, Nabb DL, Mingoia RT, Yang C-H (2007) Determination of xenobiotic intrinsic clearance in freshly isolated hepatocyte from rainbow trout (Oncorhynchus mykiss) and rat and its application in bioaccumulation risk assessment. Environ Sci Technol 41:3269–3276
Harms H, Langenbartels C (1986) Standardized plant cell suspension test systems for an ecotoxicologic evaluation of the metabolic fate of xenobiotics. Plant Sci 45: 157–165
Hellpointer E (1997) Determination of the quantum yield and assessment of the environmental half-life of the direct photodegradation of 4,4′-methylenedianiline in water. III Report No. 11265. International Isocyanate Institute, Manchester. Available from: British Library Document Supply Centre, Boston Spa, Wetherby, West Yorks. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Howard PH, Boethling RS, Jarvis WF, Meylan WM, Michalenko EM (eds) (1991) Handbook of environmental degradation rates. Lewis Publishers, Chelsea
Hsu T-S, Bartha R (1974) Biodegradation of chloroaniline-humus complexes in soil and in culture solution. Soil Sci 118:213–220
Kajbaf M, Sepai O, Lamb JH (1992) Identification of metabolites of 4,4′-diaminodiphenylmethane (methylene dianiline) using liquid chromatographic and mass spectrometric techniques. J Chromat B 583:63–76
Karabunarliev S, Dimitrov S, Pavlov T, Nedelcheva D, Mekenyan O (2012) Simulation of chemical metabolism for fate and hazard assessment. IV. Computer-based derivation of metabolic simulators from documented metabolism maps. SAR QSAR Environ Res 23:371–387
Kaufman DD, Plimmer JR, Klingebiel UI (1973) Microbial oxidation of 4-chloroaniline. J Agric Food Chem 21(1):127–132
Kim M-N, Jang J-C, Lee I-M, Lee H-S, Yoon J-S (2002) Toxicity and biodegradation of diamines. J Environ Sci Health B 37(1):53–64
Li H, Lee LS, Jafvert CT, Graveel JG (2000) Effect of substitution on irreversible binding and transformation of aromatic amines with soils in aqueous systems. Environ Sci Technol 34:3674–3680
Li H, Lee LS, Schulze DG, Guest CA (2003) Role of manganese in the oxidation of aromatic amines. Environ Sci Technol 37:2686–2693
Mei C-F, Liu Y-Z, Long W-N, Sun G-P, Zeng G-Q, Xu M-Y, Luan T-G (2015) A comparative study of biodegradability of a carcinogenic aromatic amine (4,4′-diaminodiphenylmethane) with OECD 301 test methods. Ecotoxicol Environ Saf 111:123–130
Morgott DA (1984) The in vivo biotransformation and acute hepatotoxicity of methylene dianiline. Dissertation, University of Michigan
Nabb DL, Mingoia RT, Yang CH, Han X (2006) Comparison of basal level metabolic enzyme activities of freshly isolated hepatocytes from rainbow trout (Oncorhynchuss mykiss) and rat. Aquat Toxicol 80:52–9
NITE (Japan National Institute of Technology and Evaluation) (2007) 4,4-MDA risk assessment report. http://www.nite.go.jp/chem/chrip/chrip_search/dt/pdf/CI_02_001/risk/pdf_hyoukasyo/340riskdoc.pdf
NTP (2018) Methylenedianiline (101-77-9). Chemical Effects in Biological Systems (CEBS). Research Triangle Park, NC (USA): National Toxicology Program (NTP). https://manticore.niehs.nih.gov/cebssearch/test_article/101-77-9. Accessed 14 Mar 2018
Ononyne AI, Graveel JG (1994) Modelling the reaction of 1-napthylamine and 4-methylaniline with humic acids: spectroscopic investigations of the covalent linkages. Environ Toxicol Chem 13(4):537–541
Parris GE (1980) Covalent binding of aromatic amines to humates. 1. Reactions with carbonyls and quinones. Environ Sci Technol 14(9):1099–1106
Pemberton D, Tury B (2008) Prediction of atmospheric half-lives for MDI, TDI, MDA and TDA using the AOPWIN™ model. GIL Report No. 2008/C. Global Isocyanates, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Pillai P, Helling CS, Dragun J (1982) Soil-catalyzed oxidation of aniline. Chemosphere 11(3):299–317
Saxena A, Bartha R (1983) Microbial mineralization of humic acid – 3,4-dichloroaniline complexes. Soil Biol Biochem 15(1): 59–62
Schaefer EC, Carpenter K (2013) 4,4′-MDA: aerobic mineralization in surface waters. III Report No. 11652. International Isocyanate Institute, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Schaefer EC, Ponizovsky A (2013) 4,4′-MDA: aerobic and anaerobic transformation aquatic sediment systems. III Report No. 11646. International Isocyanate Institute, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Schupp T, Allmendinger H, Bossuyt BTA, Hidding B, Tury B, West RJ (2016) Review of the ecotoxicological properties of the methylenedianiline substances. Rev Environ Contam Toxicol 241: 39–72
Schwarz H (2009) MDA determination of the ready biodegradability according to OECD Test Guideline 301B. III Report No. 11567. International Isocyanate Institute, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Suidan MT, Campo P, Platten W, Chai Y, Davis JD (2011) Aerobic biodegradation of amines in industrial saline wastewaters. Chemosphere 85:1199–1203
US EPA (2004) Appendix C to 40 CFR Part 63 - determination of the fraction biodegraded (Fbio) in a biological treatment unit. Fed Regist 69:39383–39392
Voorman R, Penner D (1986a) Fate of MBOCA [4,4′-methylene-bis(2-chloroaniline)] in soil. Arch Environ Contam Toxicol 15: 595–602
Voorman R, Penner D (1986b) Plant uptake of MBOCA [4,4′-methylene-bis(2-chloroaniline)]. Arch Environ Contam Toxicol 15: 589–593
Weber EJ, Spidle DL, Thorn KA (1996) Covalent binding of aniline to humic substances. 1: kinetic studies. Environ Sci Technol 30:2755–2763
Weber EJ, Colon, D, Baughman, GL (2002) Sediment-associated reactions of aromatic amines. 2. QSAR development. Environ Sci Technol 36:2443–2450
West RJ (2007) Evaluation of the intrinsic anaerobic biodegradability of MDA and TDA in soil-free enrichment cultures. III Report No. 11530. International Isocyanate Institute, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
West RJ, Tury B (2006) PBT categorization analysis for TDI, MDI, TDA and MDA. III Report No. 11522. International Isocyanate Institute, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
West RJ, Davis JW, Bailey RE (2002) Sorption and biodegradation of 2,4-TDA, 2,6-TDA and 4,4′-MDA in soils under anaerobic conditions: second study. III Report No. 11463. International Isocyanate Institute, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Yakabe Y (1994) The study of the environmental fate of TDA, MDA and oligoureas of MDI and TDI: biodegradability test of 2,4-diaminotoluene and 4,4′-diaminodiphenylmethane. III Report No. 11170. International Isocyanate Institute, Manchester. Robust study summary: http://apps.echa.europa.eu/registered/data/dossiers/DISS-9c7b34e3-c5c4-7414-e044-00144f67d249/AGGR-acfea30d-ad97-4274-b8ce-aabd18d556da_DISS-9c7b34e3-c5c4-7414-e044-00144f67d249.html
Acknowledgement
This work was sponsored by the International Isocyanate Institute, Inc. The views presented in this paper are those of the authors and not necessarily those of the sponsor.
Conflict of Interest
T. Schupp worked for BASF, an MDA producer, until 2012.
H. Allmendinger is a consultant for Currenta GmbH & Co. OHG.
S. Shen is working for Dow, an MDA producer.
B. T. A. Bossuyt is working for Huntsman, an MDA producer.
C. Boegi and B. Hidding are working for BASF, an MDA producer.
B. Tury and R. J. West have been employed by the International Isocyanate Institute, Inc.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Appendices
Annex 1: Output of the QSAR Toolbox Microbial Metabolism Simulator for 4,4′-MDA
Smiles notation: Nc1ccc(Cc2ccc(O)cc2)cc1
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 2.62 | 2.47E-04 | 975 |
Smiles notation: Nc1ccc(Cc2ccc(O)c(O)c2)cc1
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 2.14 | 3.42E-06 | 2,070 |
Smiles notation: Nc1ccc(Cc2ccc(N)c(O)c2O)cc1
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 1.22 | 1.16E-07 | 2,748 |
Smiles notation: Nc1ccc(Cc2ccc(O)cc2)c(O)c1O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 1.66 | 2.12E-07 | 4,372 |
Smiles notation: Oc1ccc(Cc2ccc(O)c(O)c2)cc1
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 2.57 | 5.74E-06 | 866 |
Smiles notation: Oc1ccc(Cc2ccc(O)c(O)c2)cc1O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 2.09 | 3.89E-07 | 1,830 |
Smiles notation: Oc1ccc(Cc2ccc(O)c(O)c2O)cc1O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 2.04 | 2.52E-08 | 1,678 |
Smiles notation: OC(=O)C(O)=C(O)C=CC(=O)Cc1ccc(O)c(O)c1
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 0.05 | 3.71E-12 | >1.00E05 |
Smiles notation: OC=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.54 | 4.78E03 | >1.00E05 |
Smiles notation: OC(CCC(O)=O)CC(=O)C(O)=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −2.64 | 4.94E-06 | >1.00E05 |
Smiles notation: OC(C(O)=O)C(=O)C=CC(=O)Cc1ccc(O)c(O)c1
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 0.27 | 5.85E-10 | >1.00E05 |
Smiles notation: OC(=O)CCC=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.42 | 16 | >1.00E05 |
Smiles notation: OC(=O)CCC(O)=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.59 | 2.55E-05 | >1.00E05 |
Smiles notation: OC(=O)Cc1ccc(O)c(O)c1
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 0.98 | 1.32E-04 | >1.00E05 |
Smiles notation: OC(=O)CC=CCC(=O)C(O)=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −1.32 | 1.61E-03 | >1.00E05 |
Smiles notation: OC(=O)CC=CC=C(O)C(O)=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.29 | 6.38E-06 | 1.36E05 |
Smiles notation: OC(=O)CC(C=O)=CC=C(O)C(O)=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −1.23 | 2.56E-07 | >1.00E05 |
Smiles notation: Nc1ccc(Cc2ccc(O)c(O)c2)c(O)c1O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 1.18 | 1.37E-08 | 9,191 |
Smiles notation: CCC(O)=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 0.33 | 471 | >1.00E05 |
Smiles notation: CC(=O)C(O)=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −1.24 | 172 | >1.00E05 |
Smiles notation: C=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 0.35 | 5.19E05 | >1.00E05 |
Smiles notation: C=CC=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.01 | 3.65E04 | >1.00E05 |
Smiles notation: OC(=O)C=C
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| 0.35 | 529 | 53,468 |
Smiles notation: C=CC(=O)C=O
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.36 | 1,370 | >1.00E05 |
Smiles notation: OC(C(O)=O)C(=O)C=C
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.65 | 3.86E-02 | >1.00E05 |
Smiles notation: OC(=O)C(=O)C=C
Structure | Log Kow | Vapor pressure (Pa/25°C) | Water solubility (mg/L) |
| −0.11 | 32 | >1.00E05 |
Annex 2: Summary Table of Selected EUSUS 2.1 Calculation Results
Rights and permissions
Copyright information
© 2018 Springer International Publishing AG, part of Springer Nature
About this chapter
Cite this chapter
Schupp, T. et al. (2018). The Environmental Behavior of Methylene-4,4′-dianiline. In: de Voogt, P. (eds) Reviews of Environmental Contamination and Toxicology Volume 246. Reviews of Environmental Contamination and Toxicology, vol 246. Springer, Cham. https://doi.org/10.1007/398_2018_13
Download citation
DOI: https://doi.org/10.1007/398_2018_13
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-97739-3
Online ISBN: 978-3-319-97740-9
eBook Packages: Earth and Environmental ScienceEarth and Environmental Science (R0)