The use of β-cyclodextrins to enhance the aqueous solubility of trichloroethylene and perchloroethylene and their removal from soil organic matter — Effect of substituents

Salma Shirin; Erwin Buncel; Gary W vanLoon

doi:10.1139/v07-144

The use of β-cyclodextrins to enhance the aqueous solubility of trichloroethylene and perchloroethylene and their removal from soil organic matter — Effect of substituents

Canadian Journal of Chemistry ◽

10.1139/v07-144 ◽

2008 ◽

Vol 86 (1) ◽

pp. 79 ◽

Cited By ~ 1

Author(s):

Salma Shirin ◽

Erwin Buncel ◽

Gary W vanLoon

Keyword(s):

Organic Matter ◽

Soil Organic Matter ◽

Aqueous Solubility ◽

Effect Of Substituents ◽

Matter Effect

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The use of β-cyclodextrins to enhance the aqueous solubility of trichloroethylene and perchloroethylene and their removal from soil organic matter: Effect of substituents

Canadian Journal of Chemistry ◽

10.1139/v02-205 ◽

2003 ◽

Vol 81 (1) ◽

pp. 45-52 ◽

Cited By ~ 13

Author(s):

Salma Shirin ◽

Erwin Buncel ◽

Gary W vanLoon

Keyword(s):

Organic Matter ◽

Soil Organic Matter ◽

Binding Constant ◽

Binding Constants ◽

Aqueous Solubility ◽

Solubility Enhancement ◽

Degree Of Substitution ◽

Water Remediation ◽

Effective Removal ◽

Matter Effect

This paper describes a systematic study for the evaluation of different substituted β-cyclodextrins (β-CDs), as agents for the enhancement of the aqueous solubility of two major organic pollutants, trichloroethylene (TCE) and perchloroethylene (PCE). The aqueous solubility enhancement occurs through the formation of hostguest inclusion complexes between the CD molecule (host) and the polychloroethylene (guest) and is driven primarily by hydrophobic forces. The CDs evaluated are: methyl-β-CD (Mβ-CD), hydroxypropyl-β-CD (HPβ-CD), carboxymethyl-β-CD (CMβ-CD1, CMβ-CD2), and sulfated-β-CD (Sβ-CD1, Sβ-CD2); the degree of substitution was also varied. Using a 5% (w/v) aqueous CD solution, solubility enhancement factors (St/So) up to 5.5 and 14 were determined for TCE and PCE, respectively. Binding constants (K11) for TCE with the substituted CDs were evaluated using an 1H NMR technique; these were found to range from 3 to 120 M1. It was shown that solubility enhancement, as well as the binding constant, is dependent on the type and degree of substitution of the β-CD molecule; the determining factors are discussed. The CDs are also capable of effective removal of PCE and TCE retained by soil organic matter. Thus, a suitably substituted β-CD may be a valuable additive in pump-and-treat protocols for site remediation of polychlorinated organics. Key words: Cyclodextrin, trichloroethylene, perchloroethylene, solubility enhancement, binding constant, soil and water remediation.

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Soil Organic Matter, Effect of Wheat Straw, Nitrogenous Fertilizers, and Carbon-to-Nitrogen Ratio on Organic Decomposition in a Subhumid Soil

Journal of Agricultural and Food Chemistry ◽

10.1021/jf60107a004 ◽

1960 ◽

Vol 8 (1) ◽

pp. 19-24 ◽

Cited By ~ 7

Author(s):

Purna Chandra ◽

W. B. Bollen

Keyword(s):

Organic Matter ◽

Soil Organic Matter ◽

Wheat Straw ◽

Carbon To Nitrogen Ratio ◽

Matter Effect ◽

Nitrogen Ratio ◽

Organic Decomposition

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Soil Organic Matter Effect on Activity of Acetanilides, CDAA, and Atrazine

Weed Science ◽

10.1017/s0043174500032008 ◽

1973 ◽

Vol 21 (3) ◽

pp. 157-160 ◽

Cited By ~ 21

Author(s):

J. V. Parochetti

Keyword(s):

Organic Matter ◽

Soil Organic Matter ◽

Field Study ◽

Field Experiments ◽

Herbicidal Activity ◽

Setaria Viridis ◽

Setaria Faberi ◽

Giant Foxtail ◽

Green Foxtail ◽

Matter Effect

Field and greenhouse studies were conducted to determine the influence of soil organic matter on herbicidal activity using four Pocomoke soils with organic matter contents of 4.8, 7.0, 11.9, and 17.0%. In field experiments, control of giant green foxtail [Setaria viridisvar.major(Gaud.) Posp.] was greater than 75% from all treatments of 2-chloro-2′,6′-diethyl-N-(methoxymethyl) acetanilide (alachlor), 2-chloro-N-isopropylacetanilide (propachlor), andN,N-diallyl-2-chloroacetamide (CDAA) with no statistical differences between chemicals, rates, or organic matter levels. Control was statistically lower from all 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine (atrazine) treatments except 2.6 kg/ha at 7% organic matter and 4.4 kg/ha at 7 and 17% organic matter. Under greenhouse conditions, giant foxtail (Setaria faberiHermm.) was used to establish GR50values on soils or soil mixtures containing 0.8, 1.9, 3.9, 6.4, 11.0, and 18.7% organic matter for the herbicides used in the field study and for 2-chloro-N-(1-methyl-2-propynyl)acetanilide (prynachlor). Generally as organic matter levels increased, the GR50values for herbicides increased; the rate of GR50increase varied with herbicides. A ranking of herbicides from most toxic to least toxic is: propachlor>alachlor>prynachlor>CDAA. Atrazine GR50values varied from a low similar to propachlor at 0.8% organic matter to 20 times greater than propachlor at 17% organic matter.

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