Removal of Phthalic Acid Esters from Aqueous Solution by Inclusion and Adsorption on β-Cyclodextrin

Murai, Shoji; Imajo, Satoshi; Takasu, Yasuhiro; Takahashi, Keiko; Hattori, Kiyohiko

doi:10.1021/es970463d

Cited by 94 publications

(60 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…CDs exist in three forms (a, p, and y), corresponding to progressively larger molecular size. The interior cavity of a CD molecule is hydrophobic; thus, they behave somewhat like surfactant micelles and can solubilize low polarity or nonionic SOCs (Murai, et al, 1998). CDs solubilize SOCs by forming 1 : 1 inclusion complexes through non-specific chemical interactions between the solute and the hydrophobic cavity of the CD (Cahill and Bulusu, 1993).…”

Section: Cyclodextrinsmentioning

confidence: 99%

Biodegradation of high explosives on granular activated carbon [GAC]: Enhanced desorption of high explosives from GAC -- Batch studies

Morley¹,

Speitel

1999

View full text Add to dashboard Cite

Adsorption to GAC is an effective method for removing high explosives (HE) compounds from water, but no permanent treatment is achieved. Bioregeneration, which treats adsorbed contaminants by desorption and biodegradation, is being developed as a method for reducing GAC usage rates and permanently degrading RDX and HMX. Because desorption is often the limiting mass transfer mechanism in bioregeneration systems, several methods for increasing the rate and extent of desorption of RDX and HMX are being studied. These include use of cosolvents (methanol and ethanol), surfactants (both anionic and nonionic), and p-and y-cyclodextrins. Batch experiments to characterize the desorption of these HEs from GAC have been completed using Northwestern LB-830, the GAC being used at Pantex. Over a total of 11 days of desorption, about 3% of the adsorbed RDX was desorbed from the GAC using buffered water as the desorption fluid. In comparison, about 96% of the RDX was extracted from the GAC by acetonitrile over the same desorption period. Ethanol and methanol were both effective in desorbing RDX and HMX; higher alcohol concentrations were able to desorb more HE from the GAC. Surfactants varied widely in their abilities to enhance desorption of HEs. The most effective surfactant that was studied was sodium dodecyl sulfate (SDS), which desorbed 56.4% of the adsorbed RDX at a concentration of 500 mg SDSL. The cyclodextrins that were used were marginally more effective than water. Continuous-flow column tests are underway for further testing the most promising of these methods. These results will be compared to column experiments that have been completed under baseline conditions (using buffered water as the desorption fluid). Results of this research will support modeling and design of further desorption and bioregeneration experiments.

show abstract

Section: Cyclodextrinsmentioning

confidence: 99%

Biodegradation of high explosives on granular activated carbon [GAC]: Enhanced desorption of high explosives from GAC -- Batch studies

Morley¹,

Speitel

1999

View full text Add to dashboard Cite

show abstract

“…[1][2][3][4][5][6][7][8][9] These toxic compounds result from many industrial processes, and they are common water pollutants. Therefore, it is necessary to have sorbents that are able to eliminate them.…”

Section: Introductionmentioning

confidence: 99%

Sorption properties toward substituted phenolic derivatives in water using macroporous polyamines containing ?-cyclodextrin

Crini

Janus²,

Morcellet³

et al. 1999

J. Appl. Polym. Sci.

View full text Add to dashboard Cite

Macroporous polyamines containing ␤-cyclodextrin (␤-CD) are used for the recovery of various organic pollutants from aqueous solutions. Several insoluble polyamines with various degrees of ␤-CD were prepared. Studies concerning the sorption kinetics, the effect of pollutant concentration, pH of the solutions, and ␤-CD content are presented here. The results of sorption experiments show that these sorbents exhibit high sorption capacities toward substituted phenolic derivatives. The mechanism of sorption is both physical adsorption in the resin polymer network through acid-base interactions, ion exchange, and hydrogen bonding due to the amino groups and the formation of an inclusion complex due to the ␤-CD molecules through host-guest interactions, and hydrophobic interactions such as guest-guest interactions.

show abstract

“…8,17) DEHP has a similar but slightly higher value in the octanol-water partition coefficient (log P ow ) than that of DHPP. 18,19) Another example is diethyl phthalate (DEP). 18,19) DEP enhanced sensitization to FITC as well as IL-4 production upon application to the skin with FITC.…”

Section: Discussionmentioning

confidence: 99%

“…18,19) Another example is diethyl phthalate (DEP). 18,19) DEP enhanced sensitization to FITC as well as IL-4 production upon application to the skin with FITC. 8,12) Log P ow for DEP is even lower than that of DIA, suggesting that molecules with relatively low lipophilicity, such as DIA and DEP, can enhance sensitization to FITC.…”

Section: Discussionmentioning

confidence: 99%

Dibutyl Maleate and Dibutyl Fumarate Enhance Contact Sensitization to Fluorescein Isothiocyanate in Mice

Matsuoka

Kurohane

Suzuki

et al. 2016

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Di-n-butyl phthalate (DBP), a phthalate ester, has been shown to have an adjuvant effect on fluorescein isothiocyanate (FITC)-induced contact hypersensitivity (CHS) mouse models. Di-n-butyl maleate (DBM), widely used as a plasticizer for industrial application, has been reported to cause dermatitis in humans. DBM is a butyl alcohol ester of di-carboxylic acid that represents a part of the DBP structure, while di-nbutyl fumarate (DBF) is a trans isomer of DBM. We examined whether DBM or DBF exhibits an adjuvant effect like DBP does. When BALB/c mice were epicutaneously sensitized with FITC in the presence of DBM or DBF, the FITC-specific CHS response was enhanced, as we have observed for DBP. As to underlying mechanisms, DBM and DBF facilitated the trafficking of FITC-presenting CD11c dendritic cells (DCs) from skin to draining lymph nodes and increased the cytokine production by draining lymph nodes. In conclusion, DBM and DBF may have an effect that aggravates contact dermatitis through a skin sensitization process.Key words dibutyl maleate; dibutyl fumarate; adjuvant; contact hypersensitivity; dendritic cell trafficking; cytokine productionIn 1985, a dermatitis outbreak occurred in an envelopemaking factory where di-n-butyl maleate (DBM)-containing polyvinyl acetate glue was used. 1) In 2009, a case of allergic dermatitis due to occupational exposure to DBM was reported. 2) A 47-year-old woman working as a batch mixer in a factory producing gelcoats and specialty paints developed eczematous lesions until she was withdrawn from work. Interestingly, among the North American Contact Dermatitis Group standard series, plastics, glues, adhesives as well as products in the workplace, DBM was the only chemical that gave a positive reaction in the patch test. DBM is a colorless, clear, and oily liquid used for industrial applications. DBM consists of an alkenyl di-carboxylic acid with two butyl alcohol esters of cis configuration.Di-n-butyl fumarate (DBF) is an isomer of DBM with butyl alcohol esters of trans configuration. There has been no report on dermatitis caused by DBF. However, dimethyl fumarate (DMF) has been banned for the use in consumer products in the European Union (EU), because it caused an unprecedented large-scale dermatitis outbreak. 3) DBM and DBF have been used as plasticizers, raw materials for polymer syntheses, and preservatives for oils and fats, but the risk of their use for dermatitis development has not been established. 4) DBM represents a part of the structure of di-n-butyl phthalate (DBP), an aromatic dibutyl ester. DBP is widely used as a plasticizer for consumer products such as paints, varnishes, paper coatings and cosmetics. 5,6) Our previous studies demonstrated that DBP contributed to contact hypersensitivity (CHS) to isothiocyanate haptens as adjuvant chemicals. 7) Thus, we hypothesized that DBM might exhibit an enhancing effect through a similar mechanism as observed for DBP. We also examined whether or not DBF, an isomer of DBM, produced such an enhancing effect.In this study, we ...

show abstract

Removal of Phthalic Acid Esters from Aqueous Solution by Inclusion and Adsorption on β-Cyclodextrin

Cited by 94 publications

References 31 publications

Biodegradation of high explosives on granular activated carbon [GAC]: Enhanced desorption of high explosives from GAC -- Batch studies

Biodegradation of high explosives on granular activated carbon [GAC]: Enhanced desorption of high explosives from GAC -- Batch studies

Sorption properties toward substituted phenolic derivatives in water using macroporous polyamines containing ?-cyclodextrin

Dibutyl Maleate and Dibutyl Fumarate Enhance Contact Sensitization to Fluorescein Isothiocyanate in Mice

Contact Info

Product

Resources

About