Critical review of hydrolysis of organic compounds in water under environmental conditions

Mabey, William R.; Mill, Theodore

doi:10.1063/1.555572

Cited by 464 publications

(314 citation statements)

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“…The chemical loss rates are estimated from published data which include hydrolysis, halogen substitution and photolysis. The half-lives of CHBr 3 and CH 2 Br 2 due to hydrolysis are hundreds to thousands of years (Mabey and Mill, 1978), while for CH 3 I, the half-life due to hydrolysis ranges from 1600 days at 25 • C to 4000 days at 5 • C (Elliott and Rowland, 1995). The half-life of CHBr 3 with respect to photolysis is 9 years assuming a mixed-layer depth of 100 m and is potentially longer for CH 2 Br 2 .…”

Section: Transport and Loss Processes In The Mixed Layermentioning

confidence: 99%

“…The deeper maxima may be either due to an additional source of CH 2 Br 2 such as the biologically mediated conversion of CHBr 3 or to a faster degradation of CHBr 3 than of CH 2 Br 2 at depth. Sinks for CHBr 3 and CH 2 Br 2 in tropical surface waters include very slow hydrolysis (hundreds to thousands of years; Mabey and Mill, 1978) and slow halogen substitution (5 years; Geen, 1992). Photolysis, which has been suggested to be faster for CHBr 3 (9 years with a mixed layer of 100 m for CHBr 3 ) than for CH 2 Br 2 (Carpenter et al, 2009) would be of more significance in the surface layer.…”

Section: Chbr 3 and Ch 2 Brmentioning

confidence: 99%

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Halocarbon emissions and sources in the equatorial Atlantic Cold Tongue

et al. 2015

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Abstract.Halocarbons from oceanic sources contribute to halogens in the troposphere, and can be transported into the stratosphere where they take part in ozone depletion. This paper presents distribution and sources in the equatorial Atlantic from June and July 2011 of the four compounds bromoform (CHBr 3 ), dibromomethane (CH 2 Br 2 ), methyl iodide (CH 3 I) and diiodomethane (CH 2 I 2 ). Enhanced biological production during the Atlantic Cold Tongue (ACT) season, indicated by phytoplankton pigment concentrations, led to elevated concentrations of CHBr 3 of up to 44.7 and up to 9.2 pmol L −1 for CH 2 Br 2 in surface water, which is comparable to other tropical upwelling systems. While both compounds correlated very well with each other in the surface water, CH 2 Br 2 was often more elevated in greater depth than CHBr 3 , which showed maxima in the vicinity of the deep chlorophyll maximum. The deeper maximum of CH 2 Br 2 indicates an additional source in comparison to CHBr 3 or a slower degradation of CH 2 Br 2 . Concentrations of CH 3 I of up to 12.8 pmol L −1 in the surface water were measured. In contrary to expectations of a predominantly photochemical source in the tropical ocean, its distribution was mostly in agreement with biological parameters, indicating a biological source. CH 2 I 2 was very low in the near surface water with maximum concentrations of only 3.7 pmol L −1 . CH 2 I 2 showed distinct maxima in deeper waters similar to CH 2 Br 2 . For the first time, diapycnal fluxes of the four halocarbons from the upper thermocline into and out of the mixed layer were determined. These fluxes were low in comparison to the halocarbon sea-to-air fluxes. This indicates that despite the observed maximum concentrations at depth, production in the surface mixed layer is the main oceanic source for all four compounds and one of the main driving factors of their emissions into the atmosphere in the ACTregion. The calculated production rates of the compounds in the mixed layer are 34 ± 65 pmol m −3 h −1 for CHBr 3 , 10 ± 12 pmol m −3 h −1 for CH 2 Br 2 , 21 ± 24 pmol m −3 h −1 for CH 3 I and 384 ± 318 pmol m −3 h −1 for CH 2 I 2 determined from 13 depth profiles.

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Section: Transport and Loss Processes In The Mixed Layermentioning

confidence: 99%

Section: Chbr 3 and Ch 2 Brmentioning

confidence: 99%

Halocarbon emissions and sources in the equatorial Atlantic Cold Tongue

et al. 2015

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“…In an integrated system, we expect to recycle peroxydisulfate at > 80% efficiencies at T = 20-30 o C. This efficiency has been achieved by industrial plants as well as by our laboratory cells. [1,7] A fourth key performance indicator is demonstration of general applicability, by treatment of such varied wastes as chlorinated solvents and plastics, charcoal and charcoal filters, incinerator carbon-containing chars, paper and rags, oils and greases, ion exchange resins, nitrated and nitratecontaining wastes, complexing agents (tributyl phosphate), cutting oils (Trimsol), detergents and complexing agents.…”

Section: B Indicators Of Performance For Fy97 Workmentioning

confidence: 99%

“…We have been conducting research on a Direct Chemical Oxidation process at LLNL since 1992 for application to the organic fraction of mixed wastes, to the destruction of chemical warfare agents, and for general applications to demilitarization [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. (Total internal funding by Livermore Directed Research and Development to date, ~$150 K).…”

Section: A Prior Work Fy92-fy95mentioning

confidence: 99%

Final Report: Fiscal Year 1997 demonstration of omnivorous non-thermal mixed waste treatment: Direct chemical oxidation of organic solids and liquids using peroxydisulfate

Cooper¹

1998

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“…Numerous research reports on degradation of different drugs under hydrolytic conditions are available in literature. Mabey and Mill 10 have reviewed hydrolytic behaviour of different classes of organic compounds under different chemical environments. Reviews of hydrolytic susceptibility of sulfonylureas, cellulose and polymers are also available in literature.…”

Section: Introductionmentioning

confidence: 99%

Understanding unconventional routes to impurities from drugs in hydrolytic conditions

Kaur¹,

Bansal²,

Bansal³

2016

IJPER

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Introduction: Hydrolytic degradation is the most common cause of formation of impurities or degradation products in drugs during different stages of drug product development and/or shelf life of the drug/product. Degradation products formed by hydrolysis of ester, amide, urethane, sulfonamide, sulfonate and ether linkages, and of nitrile, hydroxyl and amino groups in drugs can be conveniently predicted and identified. Many drugs are known to degrade to such expected conventional hydrolytic degradation products, and the mechanisms of such degradations are also well known and reported. However, many drugs are reported to degrade under hydrolytic conditions to products, which cannot be justified by the conventional hydrolytic reactions. Objectives: Though structures of such unconventional hydrolytic products can be characterized through different spectral techniques, but there is a need to understand the mechanisms of such unconventional hydrolytic reactions in order to help in establishing intrinsic stability characteristics of a drug. Methodology: In the present review, we have studied and critically analysed all possible reports on hydrolytic degradation of various dugs to provide a thorough insight into unconventional routes of hydrolytic degradations of drugs. The various unconventional hydrolytic reactions found responsible for degradation of drugs are classified as oxidation, dehydrogenation, coupling/condensation, N-alkylation, C-C bond cleavage, C-N bond cleavage, dehalogenation, cyclization, decarboxylation and hydroxylation. Discussion: Varied types of reactions under hydrolytic conditions are triggered/controlled by the nature of substituent(s) across or around the susceptible bonds/groups. The mechanisms for such unconventional hydrolytic reactions have been discussed or proposed with support from the standard literature. The contents are expected to enable an analyst and a drug formulator to predict various possible as well as seemingly improbable hydrolytic degradation products of a drug well ahead of systematic forced degradation studies.

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Critical review of hydrolysis of organic compounds in water under environmental conditions

Cited by 464 publications

References 1 publication

Halocarbon emissions and sources in the equatorial Atlantic Cold Tongue

Halocarbon emissions and sources in the equatorial Atlantic Cold Tongue

Final Report: Fiscal Year 1997 demonstration of omnivorous non-thermal mixed waste treatment: Direct chemical oxidation of organic solids and liquids using peroxydisulfate

Understanding unconventional routes to impurities from drugs in hydrolytic conditions

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