Reaction products of N6,N6'-hexane-1,6-diylbis[N2,N4-dibutyl-N2,N4,N6-tris(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-triazine-2,4,6-triamine] and allylbromide, subsequently reacted with ethaneperoxoic acid, hydrogenated

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

other: handbook

Adequacy of study:

supporting study

Study period:

1990

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

data from handbook or collection of data

Data source

Reference

Reference Type:

publication

Title:

Rate of hydrolysis

Author:

Harris JC

Year:

1990

Bibliographic source:

in: Lyman WJ et al., Handbook of chemical property estimation methods, 3rd edition, ACS Washington.

Materials and methods

Principles of method if other than guideline:

Hydrolysis is a chemical transformation process in which an organic molecule, RX, reacts with water, forming a new carbon-oxygen bond and cleaving a carbon-X bond in the original molecule. The net reaction is most commonly a direct displacement of X by OH:
R-X + H2O -> R-OH + X- + H+
This process can be distinguished from several other possible reactions between organic chemicals and water such as acid:base reactions, hydration of carbonyls, addition to carbon-carbon bonds, and elimination. Hydrolysis is likely to be the most important reaction of organic compounds with water in aqueous environments and is a significant environmental fate process for many organic chemicals. It is actually not one reaction but a family of reactions involving compound types as diverse as alkyl halides, carboxylic acid esters, organ-ophosphonates, carbamates, epoxides, and nitriles.

GLP compliance:

no

Test material

Radiolabelling:

no

Remarks:

not applicable, theoretical evaluation only

Study design

Analytical monitoring:

no

Remarks:

not applicable, theoretical evaluation only

Positive controls:

no

Negative controls:

no

Results and discussion

Transformation products:

not measured

Dissipation DT50 of parent compound

Remarks on result:

not measured/tested

Remarks:

not applicable, theoretical evaluation only

Any other information on results incl. tables

Many organic functional groups are relatively or completely inert with respect to hydrolysis. Other functional groups may hydrolyze under environmental conditions.

Table 1. Types of Organic Functional Groups That Are Generally Resistant to Hydrolysis ^a

Alkanes Alkenes Alkynes Benzenes/byphenyls Polycyclic aromatic hydrocarbons Heterocyclic polycyclic aromatic hydrocarbons Halogenated aromatics/PCBs Dieldrin/aldrin and related halogenated hydrocarbon pesticides

Aromatic nitro compounds Aromatic amines Alcohols Phenols Glycols Ethers Aldehydes Ketones Carboxylic acids Sulfonic acids

a. Multifunctional organic compounds in these categories may, of course, be hydrolytically reactive if they contain a hydrolyzable functional group in addition to the alcohol, acid, etc., functionality.

Table 2. Types of Organic Functional Groups That are Potentially Susceptible to Hydrolysis

Alkyl halides Amides Amines Carbamates Carboxylic acid esters Epoxides

Nitriles Phosphonic acid esters Phosphoric acid esters Sulfonic acid esters Sulfuric acid esters

Applicant's summary and conclusion

Validity criteria fulfilled:

not applicable

Remarks:

theoretical evaluation only

Conclusions:

Uncertainty in Estimating Values
Hydrolysis rate constants that are estimated by these methods are subject to the following major sources of uncertainty:
(1) The correlation equations are typically based on three to six data points. This reduces confidence in the validity of extrapolating to compounds outside the original data set.
(2) Substituent and reaction constants are obtained from a variety of sources and may refer to temperatures and reaction media that differ from those of the ambient aquatic environment.
(3) Changes in reaction mechanism across a series of related organic compounds is a real possibility.
(4) Correlation equations apply to kH, k0 and kOH individually; it may be impossible to estimate all of the rate constants required for calculation of kT and hence the hydrolysis half-life.
While it is not possible to quantify the probable uncertainties, a qualitative review would suggest that estimated k's be considered order-of-magnitude estimates. If an estimated k is within one or two orders of magnitude of the value considered critical in a given context, a sufficiently reliable value would probably be obtainable only by experimental measurement.