Highly selective transformation of poly[(R)-3-hydroxybutyric acid] into trans-crotonic acid by catalytic thermal degradation
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The presence of catalyst allowed pyrolysis to be conducted at lower temperature than without a catalyst and suppressed the formation of oligomeric species.
“The presence of catalyst not only allowed the pyrolysis to be conducted at lower temperature than without a catalyst, but also suppressed the formation of oligomeric species.”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [466]
The use of MgO or Mg(OH)2 as the catalyst enables selective thermal degradation of PHB to trans-crotonic acids.
“For example, the use of MgO or Mg(OH)2 as the catalyst enables a selective thermal degradation of PHB to trans-crotonic acids (Scheme 22B).466”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [466]
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“[Figure 1] Apparent activation energy values, Ea, for PHB-H and PHB-H/MCs degradation were estimated by using the method previously proposed by our research group [22], which is an improved method from the Doyle’s [23,24] and Reich’s [25] methods and plotted against residual weight, w, in Figure 2.”
MethodThermal degradation of poly[(R)-3-hydroxybutyrate], poly[ε-caprolactone], and poly[(S)-lactide]
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Self-citationThermal decomposition of biodegradable polyesters—I: Poly(β-hydroxybutyric acid)
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“Fax: +603- 89467510 Running title Selective transformation of PHB into trans-crotonic acid © 2010This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ Abstract Completely selective transformation of poly[(R)-3-hydroxybutyric acid] (PHB) into trans…”
MethodInfluentialSelf-citationThermal Degradation of Poly(3-hydroxyalkanoates): Preparation of Well-Defined Oligomers
Nguyen, S., Yu, G., & MARCHESSAULT, R. H. (2001) · Biomacromolecules · doi:10.1021/bm0156274 · Cited by 161 · cited 1× · see citing works
“CO2 [2,3], H2O [3], propene [2,4], ketene [3], acetaldehyde [3], 2 butyrolactone [3], trans/cis-crotonic acid (CA) [2,4-8], 3-butenoic acid (BA) [2], linear oligomers [4-6,8,9], and cyclic trimers [10].”
Pyrolysis of bacterial polyalkanoates
Morikawa, H., & MARCHESSAULT, R. H. (1981) · Canadian Journal of Chemistry · doi:10.1139/v81-334 · Cited by 147 · cited 1× · see citing works
“CO2 [2,3], H2O [3], propene [2,4], ketene [3], acetaldehyde [3], 2 butyrolactone [3], trans/cis-crotonic acid (CA) [2,4-8], 3-butenoic acid (BA) [2], linear oligomers [4-6,8,9], and cyclic trimers [10].”
Determination of multiple thermal degradation mechanisms of poly(3-hydroxybutyrate)
Ariffin, H., Nishida, H., Shirai, Y., & Hassan, M. A. (2008) · Polymer Degradation and Stability · doi:10.1016/j.polymdegradstab.2008.05.020 · Cited by 127 · cited 7× · see citing works
“In the previous report [5], we proposed a novel depolymerization mechanism: unzipping”
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“[Figure 1] Apparent activation energy values, Ea, for PHB-H and PHB-H/MCs degradation were estimated by using the method previously proposed by our research group [22], which is an improved method from the Doyle’s [23,24] and Reich’s [25] methods and plotted against residual weight, w, in Figure 2.”
MethodSelf-citationThermal Degradation of Environmentally Degradable Poly(hydroxyalkanoic acid)s
Abe, H. (2006) · Macromolecular Bioscience · doi:10.1002/mabi.200600070 · Cited by 121 · cited 1× · see citing works
“CO2 [2,3], H2O [3], propene [2,4], ketene [3], acetaldehyde [3], 2 butyrolactone [3], trans/cis-crotonic acid (CA) [2,4-8], 3-butenoic acid (BA) [2], linear oligomers [4-6,8,9], and cyclic trimers [10].”
Carboxylate-Induced Degradation of Poly(3-hydroxybutyrate)s
Kawalec, M., Adamus, G., Kurcok, P., Kowalczuk, M. M., Foltran, I., Focarete, M. L., & Scandola, M. (2007) · Biomacromolecules · doi:10.1021/bm061155n · Cited by 98 · cited 1× · see citing works
“A few reports, however, have treated the effect of catalysts on thermal degradation of PHB [10,16-18].”
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“[20] also reported on the enhancement of the thermal degradation of PHB by Naþ, Kþ, and Bu4Nþ counter cations at chain-ends, proposing an E1cB mechanism.”
BackgroundMethodInfluentialSelf-citationEffects of MgO catalyst on depolymerization of poly-l-lactic acid to l,l-lactide
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“Recent focus has been on monomer recovery from bio-based polymers, in particular, the depolymerization behavior of poly(L-lactic acid) (PLLA) into L-lactic acid and L,L-lactide, resulting in highly stereo-selective monomer recovery leading to the reproduction of PLLA [1].”
BackgroundInfluentialSelf-citationA rapid estimation of activation energy from thermogravimetric traces
Reich, L. (1964) · Journal of Polymer Science Part B Polymer Letters · doi:10.1002/pol.1964.110020611 · Cited by 90 · cited 2× · see citing works
“[Figure 1] Apparent activation energy values, Ea, for PHB-H and PHB-H/MCs degradation were estimated by using the method previously proposed by our research group [22], which is an improved method from the Doyle’s [23,24] and Reich’s [25] methods and plotted against residual weight, w, in Figure 2.”
MethodKim, K. J., Doi, Y., & Abe, H. (2006) · Polymer Degradation and Stability · doi:10.1016/j.polymdegradstab.2005.06.004 · Cited by 88 · cited 2× · see citing works
“A few reports, however, have treated the effect of catalysts on thermal degradation of PHB [10,16-18].”
BackgroundMelchiors, M., Keul, H., & Höcker, H. (1996) · Macromolecules · doi:10.1021/ma9604350 · Cited by 78 · cited 4× · see citing works
“A few reports, however, have treated the effect of catalysts on thermal degradation of PHB [10,16-18].”
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“-% using thermal volatilization analysis [3] to 87 total ion count % (TIC-%) using pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) analysis [4].”
MethodEffect of metal compounds on thermal degradation behavior of aliphatic poly(hydroxyalkanoic acid)s
Kim, K. J., Doi, Y., & Abe, H. (2008) · Polymer Degradation and Stability · doi:10.1016/j.polymdegradstab.2008.01.026 · Cited by 56 · cited 2× · see citing works
“A few reports, however, have treated the effect of catalysts on thermal degradation of PHB [10,16-18].”
BackgroundCrotonic acid as a bioactive factor in carrot seeds (Daucus carota L.)
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“Crotonic acid and its copolymers may have various specific applications; for example in dental materials, cosmetics, hair styling products, plasticizers, and herbicidal [11].”
BackgroundAnhydride production as an additional mechanism of poly(3‐hydroxybutyrate) pyrolysis
Ariffin, H., Nishida, H., Shirai, Y., & Hassan, M. A. (2008) · Journal of Applied Polymer Science · doi:10.1002/app.29034 · Cited by 27 · cited 1× · see citing works
“[7], and ourselves [27], was assigned to trimeric acids: crotonyl-3HB-3HB acids (M 1⁄4 258) based on a characteristic EI-MS signal recorded at m/z 1⁄4 259 (M þ 1).”
BackgroundSelf-citationHighly threodiisotactic polymerization of triphenylmethyl crotonate
Ute, K., Asada, T., Nabeshima, Y., & Hatada, K. (1993) · Macromolecules · doi:10.1021/ma00077a058 · Cited by 26 · cited 1× · see citing works
“Geometrically-selective trans-CA and its esters may find future application as versatile monomers for stereo-specific or optically active polymers [12-15].”
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“Geometrically-selective trans-CA and its esters may find future application as versatile monomers for stereo-specific or optically active polymers [12-15].”
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“Geometrically-selective trans-CA and its esters may find future application as versatile monomers for stereo-specific or optically active polymers [12-15].”
BackgroundHighly “Diheterotactic” Polymerization of tert-Butyl Crotonate
Ute, K., Asada, T., & Hatada, K. (1996) · Macromolecules · doi:10.1021/ma951275f · Cited by 22 · cited 1× · see citing works
“Geometrically-selective trans-CA and its esters may find future application as versatile monomers for stereo-specific or optically active polymers [12-15].”
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“The presence of moisture, fermentation residues, oxygen, metal and alkali catalysts also is known to favor thermal degradation[14,24-28].”
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“They obtained high condensate yield (over 80%) with a remarkable trans-crotonic acid yield, superior to 95% when a catalyst was used [159].”
BackgroundInfluentialEffect of additives on the melt rheology and thermal degradation of poly[(R)‐3‐hydroxybutyric acid]
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“21 , , = [(1 − )/ , + 1/ , ] (4) 417 The overall conversion yield (YNET, P3HB,3HB) calculated using the values from the above 418 kinetic models is 0.”
MethodResultInfluentialFixation of carbon dioxide by a hydrogen-oxidizing bacterium for value-added products
Yu, J. (2018) · World Journal of Microbiology and Biotechnology · doi:10.1007/s11274-018-2473-0 · Cited by 54 · see citing works
“Crotonic acid or 3-methylacrylic acid can be obtained with a high yield (> 99 wt%) via catalytic degradation of P3HB (Ariffin et al. 2010).”
BackgroundBio-based products from solar energy and carbon dioxide
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“The presence of oxidized groups on the surface of MCC‐T may enhance not only the thermal degradation of cellulose but also the degradation of PHB because they may catalyze the depolymerization reaction of PHB by interacting with the carboxyl group and favoring the chain scission reaction [43].”
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Conversion of polyhydroxybutyrate (PHB) to methyl crotonate for the production of biobased monomers
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“Several studies were performed on the thermal degradation mechanism of PHB/PHBV, in which different reaction paths were considered.”
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“So, PHBg-AA had a lower IDT value than PHB [41,42].”
BackgroundShao, Z., Kumagai, S., Kameda, T., Saito, Y., & Yoshioka, T. (2022) · Journal of Material Cycles and Waste Management · doi:10.1007/s10163-022-01573-9 · Cited by 14 · see citing works
“Metal-based catalysts, such as Zn, Ti, and Sn, were reported to facilitate the pyrolysis of PLA [22, 23], and MgO, Mg(OH)2 and CaO were used to improve the yield of crotonic acid in PHB pyrolysis [24, 25].”
MethodPreparative synthesis of Poly[(R)-3-hydroxybutyrate] monomer for enzymatic cell-free polymerization
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Kinetics of poly(3-hydroxybutyrate) hydrolysis using acidic functionalized ionic liquid as catalyst
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- Authors
- Ariffin, H., Nishida, H., Shirai, Y., & Hassan, M. A.
- Affiliations
- Universiti Putra Malaysia (MY)
- Kyushu Institute of Technology (JP)
- Corresponding author
- Ariffin, Hidayah
- Nishida, Haruo
- Venue
- Polymer Degradation and Stability
- Publisher
- Elsevier BV
- Published
- 2010-08
- Volume
- 95
- Issue
- 8
- Pages
- 1375-1381
- ISSN
- 0141-3910 (ISSN-L)
- OpenAlex
- W1970082641
- Cited by
- 85
- References
- 27
- Citations by year
- 2026: 4 · 2025: 2 · 2024: 4 · 2023: 16 · 2022: 13 · 2021: 9 · 2020: 5 · 2018: 2 · 2017: 5 · 2016: 6 · 2015: 5 · 2014: 4 · 2013: 3 · 2012: 2
- FWCI
- 1.32
- Type
- journal article
- Language
- en
- Open access
- Licence
- cc-by-nc-nd
- www.elsevier.com/tdm/userlicense/1.0/ (tdm)
- Locations
- Polymer Degradation and Stability (publishedVersion)
- Universiti Putra Malaysia Institutional Repository (Universiti Putra Malaysia) (acceptedVersion)
- Institutional Repositories DataBase (IRDB) (submittedVersion, cc-by-nc-nd)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer Science and PVC
- Physical Sciences › Materials Science › Materials Chemistry › Thermal and Kinetic Analysis
- Keywords
- polyhydroxyalkanoates, magnesium oxide catalyst, β-elimination, degradation kinetics, activation energy
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