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p -Coumaric acid photodegradation with solar light, using a 2,4,6-triphenylpyrylium salt as photosensitizer

Identifieur interne : 000421 ( Istex/Corpus ); précédent : 000420; suivant : 000422

p -Coumaric acid photodegradation with solar light, using a 2,4,6-triphenylpyrylium salt as photosensitizer

Auteurs : Ana Mar A Amat ; Antonio Arques ; Miguel Angel Miranda

Source :

RBID : ISTEX:282A1E8A3F4651601A51667C4585F2B8719C5E58

English descriptors

Abstract

p-Coumaric acid has been used as a probe in order to study the effect of solar light catalysed by 2,4,6-triphenylpyrylium salts on phenolic compounds present in olive oil industry wastewaters. The results are very satisfactory, and important degradation yields are achieved. Methylene blue has also been used as a photocatalyst, but it results in slower degradation. Other advanced oxidation methods (ozone and/or UV radiation) have been tested as well; as expected, p-coumaric acid abatement is much faster (100 times), but ozone and UV are dangerous and expensive for industrial uses. In contrast with other phenolic acids, ozone and UV do not show an important synergistic effect in p-coumaric acid oxidation. This could be due to differences in the absorption spectra. Major p-coumaric acid oxidation intermediates have been identified and quantitated by HPLC; on the basis of these data, a reaction mechanism is proposed.

Url:
DOI: 10.1016/S0926-3373(99)00080-6

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ISTEX:282A1E8A3F4651601A51667C4585F2B8719C5E58

Le document en format XML

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<div type="abstract" xml:lang="en">p-Coumaric acid has been used as a probe in order to study the effect of solar light catalysed by 2,4,6-triphenylpyrylium salts on phenolic compounds present in olive oil industry wastewaters. The results are very satisfactory, and important degradation yields are achieved. Methylene blue has also been used as a photocatalyst, but it results in slower degradation. Other advanced oxidation methods (ozone and/or UV radiation) have been tested as well; as expected, p-coumaric acid abatement is much faster (100 times), but ozone and UV are dangerous and expensive for industrial uses. In contrast with other phenolic acids, ozone and UV do not show an important synergistic effect in p-coumaric acid oxidation. This could be due to differences in the absorption spectra. Major p-coumaric acid oxidation intermediates have been identified and quantitated by HPLC; on the basis of these data, a reaction mechanism is proposed.</div>
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<note type="content">Scheme 1:</note>
<note type="content">Fig. 1: Emission spectrum of the Dulux Osram lamp.</note>
<note type="content">Fig. 2: p-Coumaric acid photodegradation with visible light (solar simulator) catalysed by pyrylium salt: ▴ total p-coumaric acid, trans p-coumaric acid, ■ cis p-coumaric acid.</note>
<note type="content">Fig. 3: p-Coumaric acid photodegradation with solar light after 1 day under different conditions: A, absence of air, B, with no stirring, C, with magnetic stirring.</note>
<note type="content">Fig. 4: p-Coumaric acid photodegradation with solar light using pyrylium salt as a catalyst. Comparison with blanks; A, with no stirring, B, with magnetic stirring. A′ and B′ are the corresponding blanks without pyrylium salt.</note>
<note type="content">Fig. 5: p-Coumaric photodegradation with solar light using 5% (weight) of pyrylium salt as a catalyst. Different initial concentrations of p-coumaric acid: 0.0001M, ■0.001M, ▴0.005M.</note>
<note type="content">Fig. 6: p-Coumaric photodegradation with solar light using pyrylium salt as a catalyst. Different concentrations of pyrylium salt: 5%, ■2%, ▴1%, ×0.5%, • 0.1%.</note>
<note type="content">Fig. 7: Intermediates of p-coumaric acid (0.005M) photodegradation with solar light catalysed by pyrylium salt. Oxalic acid, ■ maleic acid, ▴ protocatechuic aldehyde, × p-hydroxybenzoic acid, • p-hydroxybenzaldehyde.</note>
<note type="content">Fig. 8: p-Coumaric acid abatement with solar light catalysed by methylene blue. Comparison with pyrylium salt. A, pyrylium salt. B, methylene blue.</note>
<note type="content">Fig. 9: p-Coumaric photodegradiation with solar light using 5% (weight) of methylene blue as a catalyst. Different initial concentrations of p-coumaric acid: 0.0001M, ■0.001M, ▴0.005M</note>
<note type="content">Fig. 10: p-Coumaric acid (0.001M) abatement with ozone and/or UV radiation under different conditions, ○ ozone in acidic media, ■ UV in acidic media, ▵ ozone and UV in acidic media, × ozone in basic media, □ UV in basic media, • ozone and UV in basic media.</note>
<note type="content">Fig. 11: p-Coumaric acid abatement with ozone in acidic media: □ formic acid, + maleic acid, ○ p-hydroxybenzaldehyde, – p-coumaric acid, ■ protocatechuic aldehyde, × p-hydroxybenzoic acid, • protocatechuic acid, oxalic acid.</note>
<note type="content">Fig. 12: p-Coumaric acid abatement with ozone and UV in acidic media. □ formic acid, + maleic acid, ○ p-hydroxybenzaldehyde, – p-coumaric acid, ■ protocatechuic aldehyde, × p-hydroxybenzoic acid, • protocatechuic acid, oxalic acid.</note>
<note type="content">Fig. 13: p-Coumaric acid abatement with ozone in basic media. □ caffeic acid, + maleic acid, ○ p-hidroxibenzaldehyde, – p-coumaric acid, ■ protocatechuic aldehyde, × p-hydroxybenzoic acid, • protocatechuic acid, oxalic acid.</note>
<note type="content">Fig. 14: p-Coumaric acid abatement with ozone and UV in basic media. oxalic acid, ■ formic acid, ▴ maleic acid, × protocatechuic aldehyde, • p-hydroxybenzaldehyde, -- caffeic acid, + p-coumaric acid.</note>
<note type="content">Fig. 15: UV spectra of several phenolic compounds. — p-hydroxybenzaldehyde, —— protocatechuic acid, --- p-coumaric acid. The spectrum of vanillic acid closely matches that of protocatechuic acid.</note>
<note type="content">Scheme 2:</note>
<note type="content">Scheme 3:</note>
<note type="content">Scheme 4:</note>
<note type="content">Scheme 5:</note>
<note type="content">Scheme 6:</note>
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<ce:doi>10.1016/S0926-3373(99)00080-6</ce:doi>
<ce:copyright type="full-transfer" year="1999">Elsevier Science B.V.</ce:copyright>
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<head>
<ce:title>
<ce:italic>p</ce:italic>
-Coumaric acid photodegradation with solar light, using a 2,4,6-triphenylpyrylium salt as photosensitizer</ce:title>
<ce:subtitle>A comparison with other oxidation methods</ce:subtitle>
<ce:author-group>
<ce:author>
<ce:given-name>Ana Marı́a</ce:given-name>
<ce:surname>Amat</ce:surname>
<ce:cross-ref refid="FN1">
<ce:sup>1</ce:sup>
</ce:cross-ref>
<ce:cross-ref refid="AFF1">
<ce:sup>a</ce:sup>
</ce:cross-ref>
<ce:e-address>aamat@txp.upv.es</ce:e-address>
</ce:author>
<ce:author>
<ce:given-name>Antonio</ce:given-name>
<ce:surname>Arques</ce:surname>
<ce:cross-ref refid="AFF1">
<ce:sup>a</ce:sup>
</ce:cross-ref>
</ce:author>
<ce:author>
<ce:given-name>Miguel Angel</ce:given-name>
<ce:surname>Miranda</ce:surname>
<ce:cross-ref refid="AFF2">
<ce:sup>b</ce:sup>
</ce:cross-ref>
<ce:cross-ref refid="CORR1">*</ce:cross-ref>
<ce:e-address>mmiranda@qim.upv.es</ce:e-address>
</ce:author>
<ce:affiliation id="AFF1">
<ce:label>a</ce:label>
<ce:textfn>Departamento de Ingenierı́a Textil y Papelera, EPSA-UPV, Universidad Politécnica de Valencia, Paseo Viaducto 1, E-03801 Alcoy (Alicante), Spain</ce:textfn>
</ce:affiliation>
<ce:affiliation id="AFF2">
<ce:label>b</ce:label>
<ce:textfn>Departamento de Quı́mica e Instituto de Tecnologı́a Quı́mica CSIC-UPV, Universidad Politécnica de Valencia, Apartado 22012, E-46071 Valencia, Spain</ce:textfn>
</ce:affiliation>
<ce:correspondence id="CORR1">
<ce:label>*</ce:label>
<ce:text>Corresponding author. Tel.: +34-96-387-7343; fax: +34-96-387-7349</ce:text>
</ce:correspondence>
<ce:footnote id="FN1">
<ce:label>1</ce:label>
<ce:note-para>Co-corresponding author.</ce:note-para>
</ce:footnote>
</ce:author-group>
<ce:date-received day="4" month="2" year="1999"></ce:date-received>
<ce:date-revised day="29" month="6" year="1999"></ce:date-revised>
<ce:date-accepted day="4" month="7" year="1999"></ce:date-accepted>
<ce:abstract>
<ce:section-title>Abstract</ce:section-title>
<ce:abstract-sec>
<ce:simple-para>
<ce:italic>p</ce:italic>
-Coumaric acid has been used as a probe in order to study the effect of solar light catalysed by 2,4,6-triphenylpyrylium salts on phenolic compounds present in olive oil industry wastewaters. The results are very satisfactory, and important degradation yields are achieved. Methylene blue has also been used as a photocatalyst, but it results in slower degradation. Other advanced oxidation methods (ozone and/or UV radiation) have been tested as well; as expected,
<ce:italic>p</ce:italic>
-coumaric acid abatement is much faster (100 times), but ozone and UV are dangerous and expensive for industrial uses. In contrast with other phenolic acids, ozone and UV do not show an important synergistic effect in
<ce:italic>p</ce:italic>
-coumaric acid oxidation. This could be due to differences in the absorption spectra. Major
<ce:italic>p</ce:italic>
-coumaric acid oxidation intermediates have been identified and quantitated by HPLC; on the basis of these data, a reaction mechanism is proposed.</ce:simple-para>
</ce:abstract-sec>
</ce:abstract>
<ce:keywords class="keyword" xml:lang="en">
<ce:section-title>Keywords</ce:section-title>
<ce:keyword>
<ce:text>2,4,6-Triphenylpyrylium</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>
<ce:italic>p</ce:italic>
-Coumaric acid</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Photodegradation</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Solar light</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Oxidation</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Ozone</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Methylene blue</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Wastewaters</ce:text>
</ce:keyword>
</ce:keywords>
</head>
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<title>-Coumaric acid photodegradation with solar light, using a 2,4,6-triphenylpyrylium salt as photosensitizer</title>
<subTitle>A comparison with other oxidation methods</subTitle>
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<namePart type="given">Ana Marı́a</namePart>
<namePart type="family">Amat</namePart>
<affiliation>E-mail: aamat@txp.upv.es</affiliation>
<affiliation>Departamento de Ingenierı́a Textil y Papelera, EPSA-UPV, Universidad Politécnica de Valencia, Paseo Viaducto 1, E-03801 Alcoy (Alicante), Spain</affiliation>
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<namePart type="given">Miguel Angel</namePart>
<namePart type="family">Miranda</namePart>
<affiliation>E-mail: aamat@txp.upv.es</affiliation>
<affiliation>Departamento de Quı́mica e Instituto de Tecnologı́a Quı́mica CSIC-UPV, Universidad Politécnica de Valencia, Apartado 22012, E-46071 Valencia, Spain</affiliation>
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<abstract lang="en">p-Coumaric acid has been used as a probe in order to study the effect of solar light catalysed by 2,4,6-triphenylpyrylium salts on phenolic compounds present in olive oil industry wastewaters. The results are very satisfactory, and important degradation yields are achieved. Methylene blue has also been used as a photocatalyst, but it results in slower degradation. Other advanced oxidation methods (ozone and/or UV radiation) have been tested as well; as expected, p-coumaric acid abatement is much faster (100 times), but ozone and UV are dangerous and expensive for industrial uses. In contrast with other phenolic acids, ozone and UV do not show an important synergistic effect in p-coumaric acid oxidation. This could be due to differences in the absorption spectra. Major p-coumaric acid oxidation intermediates have been identified and quantitated by HPLC; on the basis of these data, a reaction mechanism is proposed.</abstract>
<note type="content">Scheme 1: </note>
<note type="content">Fig. 1: Emission spectrum of the Dulux Osram lamp.</note>
<note type="content">Fig. 2: p-Coumaric acid photodegradation with visible light (solar simulator) catalysed by pyrylium salt: ▴ total p-coumaric acid, trans p-coumaric acid, ■ cis p-coumaric acid.</note>
<note type="content">Fig. 3: p-Coumaric acid photodegradation with solar light after 1 day under different conditions: A, absence of air, B, with no stirring, C, with magnetic stirring.</note>
<note type="content">Fig. 4: p-Coumaric acid photodegradation with solar light using pyrylium salt as a catalyst. Comparison with blanks; A, with no stirring, B, with magnetic stirring. A′ and B′ are the corresponding blanks without pyrylium salt.</note>
<note type="content">Fig. 5: p-Coumaric photodegradation with solar light using 5% (weight) of pyrylium salt as a catalyst. Different initial concentrations of p-coumaric acid: 0.0001M, ■0.001M, ▴0.005M.</note>
<note type="content">Fig. 6: p-Coumaric photodegradation with solar light using pyrylium salt as a catalyst. Different concentrations of pyrylium salt: 5%, ■2%, ▴1%, ×0.5%, • 0.1%.</note>
<note type="content">Fig. 7: Intermediates of p-coumaric acid (0.005M) photodegradation with solar light catalysed by pyrylium salt. Oxalic acid, ■ maleic acid, ▴ protocatechuic aldehyde, × p-hydroxybenzoic acid, • p-hydroxybenzaldehyde.</note>
<note type="content">Fig. 8: p-Coumaric acid abatement with solar light catalysed by methylene blue. Comparison with pyrylium salt. A, pyrylium salt. B, methylene blue.</note>
<note type="content">Fig. 9: p-Coumaric photodegradiation with solar light using 5% (weight) of methylene blue as a catalyst. Different initial concentrations of p-coumaric acid: 0.0001M, ■0.001M, ▴0.005M</note>
<note type="content">Fig. 10: p-Coumaric acid (0.001M) abatement with ozone and/or UV radiation under different conditions, ○ ozone in acidic media, ■ UV in acidic media, ▵ ozone and UV in acidic media, × ozone in basic media, □ UV in basic media, • ozone and UV in basic media.</note>
<note type="content">Fig. 11: p-Coumaric acid abatement with ozone in acidic media: □ formic acid, + maleic acid, ○ p-hydroxybenzaldehyde, – p-coumaric acid, ■ protocatechuic aldehyde, × p-hydroxybenzoic acid, • protocatechuic acid, oxalic acid.</note>
<note type="content">Fig. 12: p-Coumaric acid abatement with ozone and UV in acidic media. □ formic acid, + maleic acid, ○ p-hydroxybenzaldehyde, – p-coumaric acid, ■ protocatechuic aldehyde, × p-hydroxybenzoic acid, • protocatechuic acid, oxalic acid.</note>
<note type="content">Fig. 13: p-Coumaric acid abatement with ozone in basic media. □ caffeic acid, + maleic acid, ○ p-hidroxibenzaldehyde, – p-coumaric acid, ■ protocatechuic aldehyde, × p-hydroxybenzoic acid, • protocatechuic acid, oxalic acid.</note>
<note type="content">Fig. 14: p-Coumaric acid abatement with ozone and UV in basic media. oxalic acid, ■ formic acid, ▴ maleic acid, × protocatechuic aldehyde, • p-hydroxybenzaldehyde, -- caffeic acid, + p-coumaric acid.</note>
<note type="content">Fig. 15: UV spectra of several phenolic compounds. — p-hydroxybenzaldehyde, —— protocatechuic acid, --- p-coumaric acid. The spectrum of vanillic acid closely matches that of protocatechuic acid.</note>
<note type="content">Scheme 2: </note>
<note type="content">Scheme 3: </note>
<note type="content">Scheme 4: </note>
<note type="content">Scheme 5: </note>
<note type="content">Scheme 6: </note>
<subject lang="en">
<genre>Keywords</genre>
<topic>2,4,6-Triphenylpyrylium</topic>
<topic>p-Coumaric acid</topic>
<topic>Photodegradation</topic>
<topic>Solar light</topic>
<topic>Oxidation</topic>
<topic>Ozone</topic>
<topic>Methylene blue</topic>
<topic>Wastewaters</topic>
</subject>
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