Bisisobutyryl peroxide

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

other: Literature

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

data from handbook or collection of data

Qualifier:

no guideline followed

Principles of method if other than guideline:

See Results field.

GLP compliance:

no

Inoculum or test system:

other: see summary on results

Parameter:

other: see results field

Remarks:

see results field

Remarks on result:

other: see results field

Remarks on result:

other: see results field

ASSESSMENT OF READY BIODEGRADABILITY OF DIISOBUTYRYL PEROXIDE (TRIGONOX 187) USING WEIGHT OF EVIDENCE APPROACH

Diisobutyryl peroxide is an instable substance. It is therefore assumed that in soils and surface waters rapid conversion of this peroxide into isobutyric acid takes place. The biodegradability of diisobutyryl peroxide and isobutyric acid are therefore equal. The branched fatty acid, isobutyric acid (2-methyl-propionic acid) is an intermediate in the microbial degradation of valine (dePaul Marshal and Sokatch, 1972). Isobutyric acid is also excreted by microorganisms during fermentation of valine (Sanceda et al. 2003). Valine is initially deaminated and subsequently decarboxylated. As a result isobutyric acid is present in many fermented food products (Allison and Bryant 1963; Beck 2005). It is also present in certain plants, fruits (Panagou and Tassou 2006; Cantalejo 1997) and insects (Seigler and Lampman 2000). Isobutyric acid consequently occurs naturally in soils and fresh water systems. Natural occurrence already points to the ready biodegradability of this fatty acid. A ready biodegradability test result provides the following information about different aspects of biodegradation 1) ultimate (complete) biodegradation by micro-organism capable of utilizing the test substance as sole carbon and energy source, 2) high rate of biodegradation by micro-organisms growing on isobutyric acid and finally 3) the wide-spread occurrence of competent micro-organisms present in ecosystems and biological treatment plants. Below all three aspects are dealt with to enable classification of isobutyric acid. Ultimate (complete) biodegradation; The enzymes involved in microbial isobutyrate degradation have been identified. Isobutyrate is activated to its CoA derivative and subsequently oxidized to methylmalonate semialdehyde. Decarboxylation of methylmalonate semialdehyde yields propionyl CoA. Propionyl- CoA is channeled into the citric acid cycle. Microorganisms therefore have the ability to degrade isobutyric acid completely. Rate of biodegradation; Growth rates on isobutyric acid were only determined for bacteria isolated from a soda lake and soda soil (very alkaline environments). The growth rates of these bacteria were 0.045, 0.25, 0.16 and 0.33 h-1 (Sorokin et al. 2007). Rates in alkaline environments are usually low compared to environments with a pH of 6 to 8. Painter and King (1983) used a model based on the Monod equation to interpret the biodegradation curves in ready biodegradability tests. According to this model growth rates of competent micro-organisms of 0.025 h-1 or higher will result in a ready biodegradation of the test substance (degradation within 28 days in an OECD 301 test).

Ubiquitousness of competent micro-organisms; Isobutyric acid utilizing bacteria (also anaerobic) were present in industrial waste water treatment plants (Cibis et al. 2002; Tholozan et al. 1988), a thermophilic sludge pretreatment plant (Haner et al. 1994), bacteria isolated from wastewater treatment plants capable of utilizing isobutyric acid were Denitratisoma oestradiolicum (Fahrbach et al. 2006), Delftia tsuruhatensis (Shigematsu et al. 2003), Comamonas nitrativorans (Kim et al. 2008) and Clostridium thiosulfatireducens (Hernández-Eugenio et al. 2002). Actinobacteria and in the Marinospirillia were isolated from the soda lake sediment (Sorokin et al. 2007). Desulfococcus multivorans was found in a marine sediment was (Stieb and Schink 1989). Isobutyric acid utilizing bacteria are therefore expected to be widely distributed in the environment. The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.

Interpretation of results:

readily biodegradable

Conclusions:

The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.

Executive summary:

The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.

Description of key information

The instable nature of Diisobutyryl peroxide leads to rapid thermal and hydrolytic breakdown of the substance to Isobutyric acid (main degradation

product). Isobutyric acid is naturally occurring and is itself readily biodegradable. Literature references supporting this are listed in the expert

statement (below) in the discussion.

Key value for chemical safety assessment

Biodegradation in water:

readily biodegradable

Additional information

ASSESSMENT OF READY BIODEGRADABILITY OF DIISOBUTYRYL PEROXIDE (TRIGONOX 187) USING WEIGHT OF EVIDENCE APPROACH

Diisobutyryl peroxide is an instable substance. It is therefore assumed that in soils and surface waters rapid conversion of this peroxide into isobutyric acid takes place. The biodegradability of diisobutyryl peroxide and isobutyric acid are therefore equal. The branched fatty acid, isobutyric acid (2-methyl-propionic acid) is an intermediate in the microbial degradation of valine (dePaul Marshal and Sokatch, 1972). Isobutyric acid is also excreted by microorganisms during fermentation of valine (Sanceda et al. 2003). Valine is initially deaminated and subsequently decarboxylated. As a result isobutyric acid is present in many fermented food products (Allison and Bryant 1963; Beck 2005). It is also present in certain plants, fruits (Panagou and Tassou 2006; Cantalejo 1997) and insects (Seigler and Lampman 2000). Isobutyric acid consequently occurs naturally in soils and fresh water systems. Natural occurrence already points to the ready biodegradability of this fatty acid. A ready biodegradability test result provides the following information about different aspects of biodegradation 1) ultimate (complete) biodegradation by micro-organism capable of utilizing the test substance as sole carbon and energy source, 2) high rate of biodegradation by micro-organisms growing on isobutyric acid and finally 3) the wide-spread occurrence of competent micro-organisms present in ecosystems and biological treatment plants. Below all three aspects are dealt with to enable classification of isobutyric acid. Ultimate (complete) biodegradation; The enzymes involved in microbial isobutyrate degradation have been identified. Isobutyrate is activated to its CoA derivative and subsequently oxidized to methylmalonate semialdehyde. Decarboxylation of methylmalonate semialdehyde yields propionyl CoA. Propionyl- CoA is channeled into the citric acid cycle. Microorganisms therefore have the ability to degrade isobutyric acid completely. Rate of biodegradation; Growth rates on isobutyric acid were only determined for bacteria isolated from a soda lake and soda soil (very alkaline environments). The growth rates of these bacteria were 0.045, 0.25, 0.16 and 0.33 h-1 (Sorokin et al. 2007). Rates in alkaline environments are usually low compared to environments with a pH of 6 to 8. Painter and King (1983) used a model based on the Monod equation to interpret the biodegradation curves in ready biodegradability tests. According to this model growth rates of competent micro-organisms of 0.025 h-1 or higher will result in a ready biodegradation of the test substance (degradation within 28 days in an OECD 301 test).

Ubiquitousness of competent micro-organisms; Isobutyric acid utilizing bacteria (also anaerobic) were present in industrial waste water treatment plants (Cibis et al. 2002; Tholozan et al. 1988), a thermophilic sludge pretreatment plant (Haner et al. 1994), bacteria isolated from wastewater treatment plants capable of utilizing isobutyric acid were Denitratisoma oestradiolicum (Fahrbach et al. 2006), Delftia tsuruhatensis (Shigematsu et al. 2003), Comamonas nitrativorans (Kim et al. 2008) and Clostridium thiosulfatireducens (Hernández-Eugenio et al. 2002). Actinobacteria and in the Marinospirillia were isolated from the soda lake sediment (Sorokin et al. 2007). Desulfococcus multivorans was found in a marine sediment was (Stieb and Schink 1989). Isobutyric acid utilizing bacteria are therefore expected to be widely distributed in the environment. The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.

References

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