Synthesis of Bio-aromatics from Black Liquors Using Catalytic Pyrolysis.
Open accessAbstract
Bio-aromatics (benzene, toluene, xylenes, BTX) were prepared by the catalytic pyrolysis of six different black liquors using both in situ and ex situ approaches.
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Claims the paper makes
3 of 11 cited sources checked · 0 supported · 0 flagged · accuracy not yet measured
- Interpretationcitation
It is likely that high temperature and catalyst acidity first cleave methoxy groups, converting syringyl and guaiacyl lignin units mainly into catechols and pyrogallols.
“It seems likely that at first methoxy groups are cleaved by the high temperature and acidity of the catalyst. As most of the monomers of lignins consist of syringyl (S) and guaiacyl units (G) and to a lesser extent of p-hydroxphenyl units (H), this results in a mixture of mainly catechols/pyrogallols.39”
Quote in the paperNot a substantial claim1 of 1 sources checked- cites [39] Novaes, 2010, Lignin and Biomass: A Negative Correlation for Wood Formation and Lignin Content in Trees, Plant Physiol. source
The LIGNIN VARIATION section identifies guaiacyl and syringyl as the two main types of lignin subunits. It does not describe high-temperature, acid-catalyzed methoxy cleavage or the formation of catechols and pyrogallols; searches for those terms found no supporting passage. No page number was provided for the indexed passage. (LLM, conf=0.84)
Experimental — accuracy not yet measured
- Premisecitation
A main disadvantage of in situ catalytic pyrolysis of biomass is possible irreversible deactivation of the acidic zeolite by inorganic cations (Na+, K+, Ca2+) in the feedstock.
“It is well-recognized that one of the main disadvantages of an in situ catalytic pyrolysis of biomass is the potential irreversible deactivation of the acidic zeolite catalyst by inorganic cations (Na+, K+, Ca2+) present in the feed stock.34”
Quote in the paperSubstantial claim1 of 1 sources checked- cites [34] Paasikallio, 2014, Product quality and catalyst deactivation in a four day catalytic fast pyrolysis production run, Green Chem. source
The Introduction identifies biomass metals as a potential cause of catalyst deactivation, and §3.3 reports that metal accumulation coincided with declining HZSM-5 acidity; it also describes the observed deactivation as potentially permanent (page numbers unavailable). The paper does not establish this as a well-recognized main disadvantage—it says only a limited number of studies had addressed the phenomenon—and its reported metal measurements include K and Ca but not Na. (LLM, conf=0.85)
Experimental — accuracy not yet measured
- Findingown data
Catalytic pyrolysis of six different black liquors, using both in situ and ex situ configurations, produced BTX (benzene, toluene, xylenes).
“Bio-aromatics (benzene, toluene, xylenes, BTX) were prepared by the catalytic pyrolysis of six different black liquors using both in situ and ex situ approaches.”
Quote in the paperSubstantial claim - Findingown data
The highest BTX yield was about 7 wt % of the organic fraction in the black liquors, obtained in both configurations at 500-600 °C with a Ga-modified H-ZSM-5 catalyst.
“Up to 7 wt % of BTX, based on the organic fraction of the black liquors, was obtained for both the in situ and ex situ pyrolysis (T = 500–600 °C) using a Ga-modified H-ZSM-5 catalyst.”
- Also stated in: § Conclusions · plain
“Our screening program showed that acidic, preferably gallium impregnated, H-ZSM-5 catalysts afforded BTX in yields of about 5–7 wt % based on the organic fraction present in the black liquor.”
Quote in the paperSubstantial claim - Also stated in: § Conclusions · plain
- Findingnone given
The organic fraction of Eucalyptus hardwood black liquor consists of 80% lignins and 20% oxidized hemicellulose/cellulose.
“For eucalyptus hardwood the organic fraction is a mixture of lignins (80%) and (oxidized) (hemi)cellulose (20%).”
Quote in the paperNot a substantial claim
- Findingown data
For Eucalyptus hardwood black liquor in ex situ pyrolysis, the highest BTX yields came from Ga-impregnated H-ZSM-5 (50) and H-ZSM-5 (23) at aromatization temperatures of 550-600 °C.
“For Eucalyptus hardwood black liquor, highest yields of BTX were obtained using Ga-impregnated H-ZSM-5 (50) and H-ZSM-5 (23) at aromatization temperatures of T = 550–600 °C (Figure 5).”
Quote in the paperSubstantial claim - Findingown data
The catalytic pyrolysis conditions achieved almost complete deoxygenation of the lignin and carbohydrate fractions of black liquor.
“An almost full deoxygenation of the lignin and carbohydrate fraction was achieved”
- Also stated in: § Ex Situ Pyrolysis in a Tandem micro-Reactor (TMR) · boosted
“Almost no phenols or small organic acids are present and it can be concluded that almost full deoxygenation occurs under the prevailing reaction conditions.”
Quote in the paperSubstantial claim - Also stated in: § Ex Situ Pyrolysis in a Tandem micro-Reactor (TMR) · boosted
- Findingown data
BTX yields from in situ and ex situ catalytic pyrolysis of black liquors were not significantly different.
“The results are given in Figure 7 and show that the BTX yields for in- and ex-situ approach do not differ significantly.”
- Also stated in: § Conclusions · plain
“No significant differences were observed in the BTX yields for the in situ and ex situ approach.”
Quote in the paperSubstantial claim - Also stated in: § Conclusions · plain
- Findingown data
In in situ pyrolysis of as-received Eucalyptus black liquor, Ga-ZSM-5 (50) raised the BTX yield slightly to 3.25%.
“Experiments with the metal-impregnated catalyst (Ga-ZSM-5 (50), slightly increased the yield of BTX to 3.25%.”
Quote in the paperSubstantial claim - Findingown data
Ex situ catalytic pyrolysis also showed higher BTX yields for hardwood black liquors than for softwood black liquors.
“a trend that could be confirmed by the results obtained in the ex situ catalytic pyrolysis.”
- Also stated in: § Ex Situ Pyrolysis in a Tandem micro-Reactor (TMR) · hedged
“The results obtained are slightly lower than the in situ pyrolysis but also in this case it seems that hardwood black liquors result in higher yields of BTX than softwood analogs.”
Quote in the paperNot a substantial claim - Also stated in: § Ex Situ Pyrolysis in a Tandem micro-Reactor (TMR) · hedged
- Findingown data
The ex situ BTX yield of about 3.5% for Eucalyptus hardwood was comparable to in situ catalytic pyrolysis values.
“The yields (about 3.5%) are in line with the values observed for the in situ catalytic pyrolysis.”
Quote in the paperNot a substantial claim - Findingown data
In in situ catalytic pyrolysis, selectivity among individual aromatics followed xylenes > toluene > benzene.
“In general the selectivity between the individual aromatics is in the order xylenes > toluene > benzene.”
- Also stated in: § In Situ Catalytic Pyrolysis of Black Liquor · plain
“In general the selectivity for the lower molecular weight aromatics follows the trend xylenes > toluene > benzene.”
Quote in the paperNot a substantial claim - Also stated in: § In Situ Catalytic Pyrolysis of Black Liquor · plain
- Findingown data
In ex situ pyrolysis, the highest BTX yields were obtained from hardwood black liquors with Ga-ZSM-5 (50) at pyrolysis and aromatization temperatures of 500 °C and 600 °C.
“Highest yields of BTX were obtained for the ex situ pyrolysis of black liquor from hardwoods using a Ga-ZSM-5 (50) catalyst (T1 = 500 °C, T2 = 600 °C).”
Quote in the paperSubstantial claim - Findingreasoning
Eucalyptus hardwood black liquor gave slightly lower BTX yields than the other black liquors in in situ pyrolysis.
“The yields of BTX for Eucalyptus hardwood are slightly lower than for the other black liquors.”
Quote in the paperNot a substantial claim - Findingreasoning
As-received black liquors gave higher BTX yields based on organic fraction than black liquors that were freeze-dried before pyrolysis.
“Furthermore, it was observed, that the yields (based on the organic fraction of the black liquors) for the as received black liquors were higher compared to black liquors that were freeze-dried before pyrolysis.”
Quote in the paperSubstantial claim - Findingown data
Among the catalysts screened, the ZSM-5 series had the greatest potential for producing BTX.
“The ZSM-5 series have highest potential for preparation of BTX.”
Quote in the paperSubstantial claim - Findingown data
In in situ pyrolysis, BTX yields varied from 3.25% to 6.75% of feed organics depending on the black liquor feedstock.
“Depending on the feedstock, the yields of BTX vary between 3.25 and 6.75%, based upon organics in the feed.”
Quote in the paperNot a substantial claim - Findingreasoning
Sodium-exchanged forms of some screened catalysts were inactive.
“In line with this observation is that the Na salt of some of the catalysts used were inactive.”
Quote in the paperNot a substantial claim - Findingown data
The lignin and carbohydrate fractions of black liquor were both converted into a broad range of substituted aromatics.
“both organic fractions were converted to a broad range of (substituted) aromatics.”
- Also stated in: § Ex Situ Pyrolysis in a Tandem micro-Reactor (TMR) · plain
“GC-MS confirms the formation of a complex mixture of substituted aromatics, including BTX.”
Quote in the paperSubstantial claim - Also stated in: § Ex Situ Pyrolysis in a Tandem micro-Reactor (TMR) · plain
- Findingreasoning
In ex situ pyrolysis of Eucalyptus hardwood black liquor, changing the pyrolysis reactor temperature from 400 to 600 °C had negligible effect on BTX yield.
“For the ex situ pyrolysis of Eucalyptus hardwood, the effect of T1 within the range of T = 400–600 °C on the BTX yields was negligible.”
Quote in the paperNot a substantial claim - Findingown data
In in situ catalytic pyrolysis, black liquors from hardwood paper mills gave slightly higher aromatics/BTX yields than black liquors from softwood paper mills.
“The in situ catalytic pyrolysis of black liquors from hardwood paper mills afforded slightly higher yields of aromatics/BTX than softwood black liquors”
- Also stated in: § In Situ Catalytic Pyrolysis with Best Catalysts Using Various Black Liquors · hedged
“Furthermore, it seems that black liquors originating from hardwood paper mills give higher yields of BTX compared to black liquors from softwood paper mills for in situ catalytic pyrolysis.”
Quote in the paperNot a substantial claim - Also stated in: § In Situ Catalytic Pyrolysis with Best Catalysts Using Various Black Liquors · hedged
- Findingown data
The black liquors used contained a high amount of inorganics.
“Of relevance is the high amount of inorganics, which may have an effect on catalyst activity and particularly stability (due to irreversible zeolite deactivation), and even be catalysts by themselves.”
Quote in the paperSubstantial claim - Findingown data
For most black liquors tested in in situ pyrolysis, Ga-ZSM-5 (50) gave the highest BTX yields.
“Highest BTX yields for most of the black liquors are observed for the Ga-ZSM-5 (50) catalyst.”
Quote in the paperSubstantial claim - Interpretationreasoning
Ex situ pyrolysis of black liquor could potentially be implemented at large scale in a paper mill without disrupting paper production.
“The ex situ pyrolysis of black liquor has potential for large-scale implementation in a paper mill without disturbing the paper production process.”
- Also stated in: § Discussion · hedged
“The ex situ catalytic pyrolysis thus seems applicable for implementation in paper mills without a major disturbance of the overall pulping process.”
Quote in the paperSubstantial claim - Also stated in: § Discussion · hedged
- Interpretationreasoning
Further reactions of small organic fractions, such as Friedel-Crafts alkylations, Diels-Alder reactions, and aldol condensations, produce more highly substituted aromatics.
“However, this does not seem to be the end point of the reaction and further reaction with small organic fraction (Friedel Craft alkylations, Diels–Alder, aldol condensations, etc.) toward higher substituted aromatics occurs.”
Quote in the paperNot a substantial claim - Interpretationreasoning
From an industrial perspective, ex situ pyrolysis of black liquor is preferred because it prevents catalyst deactivation by inorganics in the feed.
“However, from an industrial point of view the ex situ pyrolysis of black liquor seems preferred as this prevents catalyst deactivation by inorganics in the black liquor feed.”
Quote in the paperSubstantial claim- Rests on an assumption: Black liquor from paper mills contains high amounts of sodium and potassium.
- Interpretationown data
Irreversible catalyst deactivation did not occur to a significant extent in the ex situ process.
“and (ii) irreversible deactivation also does not occur to a significant extent.”
Quote in the paperSubstantial claim - Interpretationreasoning
Entrainment of metals from the pyrolysis reactor to the aromatization reactor, for example as aerosols, does not appear to be a major issue.
“As such, entrainment of metals from the pyrolysis reactor to the aromatization reactor, for example, in the form of aerosols, seems not to be a major issue.”
Quote in the paperNot a substantial claim
- May combine two claims. 12
- Classified as probably not a substantial claim. 2
May combine two claims.
PremisecitationGallium impregnation affects the Brønsted acidity of the catalysts and is known to promote deoxygenation/decarbonylation of phenols and aromatization of aliphatics/olefins.
“The impregnation of the catalysts with gallium not only effects the Bronsted acidity of the catalysts but it is also known that it positively influences the deoxygenation/decarbonylation of phenols and is able to aromatize aliphatics/olefins, in our case originating from remaining carbohydrates and the aliphatic backbone of the lignin framework of black liquor.36”
Quote in the paperSubstantial claim1 of 1 sources checked- cites [36] Cheng, 2012, Production of Renewable Aromatic Compounds by Catalytic Fast Pyrolysis of Lignocellulosic Biomass with Bifunctional Ga/ZSM-5 Catalysts, Angew. Chem., Int. Ed. source
In the catalyst-characterization discussion (page unavailable), the paper reports that increasing Ga content lowers the ratio of Brønsted to total acid sites. Its furan-conversion results say Ga promotes furan decarbonylation and olefin aromatization, and its background discussion notes alkane aromatization. It does not establish that Ga promotes deoxygenation or decarbonylation of phenols; phenol appears as a product in the pinewood results, not as a tested feedstock. (LLM, conf=0.87)
Experimental — accuracy not yet measured
May combine two claims.
Findingown dataFor non-impregnated ZSM-5 analogues (23, 50, 80), ex situ BTX yields were similar at 600-625 °C, but at lower temperatures higher Si/Al ratios gave lower yields.
“For the nonimpregnated ZSM-5 analogues (23, 50, 80) the yields of BTX are almost similar (T = 600–625 °C) but at lower temperatures higher Si–Al ratio’s (lower acidity) result in lower yields of BTX.”
Quote in the paperNot a substantial claimMay combine two claims.
Findingown dataZn- and Mo-ZSM-5 (23) gave BTX yields similar to the non-metal-impregnated zeolite, indicating no beneficial effect from Zn or Mo.
“The yields for the Zn- and Mo-ZSM-5 (23) catalysts are in line with the nonmetal impregnated zeolite and thus these metals do not seem to have a beneficial effect on BTX formation.”
Quote in the paperNot a substantial claimMay combine two claims.
Findingown dataThe zeolite catalyst remained stable over 100 batch experiments with intermittent oxidative regeneration, with BTX yields and selectivity staying similar.
“The zeolite catalyst used was remarkably stable and even after 100 experiments in batch mode with intermittent oxidative catalyst regeneration, the yields and selectivity toward BTX remained similar.”
- Also stated in: § Catalyst Deactivation-Regeneration Studies Using H-ZSM-5 (23) · plain
“Figure 9 shows that even after 100 experiments the catalyst is still active and the yield of BTX and the ratio of the individual aromatics remains similar.”
Quote in the paperSubstantial claim- Also stated in: § Catalyst Deactivation-Regeneration Studies Using H-ZSM-5 (23) · plain
May combine two claims.
Findingown dataThe black liquors used had water contents between 26% and 35% and organic contents between 33% and 42%.
“In general the water content of all black liquors used is between 26% and 35% and the organic content between 33% and 42%.”
Quote in the paperNot a substantial claimMay combine two claims.
Findingown dataBTX yield was highest for H-ZSM-5 (50), with lower yields for the more acidic H-ZSM-5 (23) and the less acidic H-ZSM-5 (80) and H-ZSM-5 (280).
“The acidity of the catalyst seems to have an optimum for H-ZSM-5 (50), as lower yields of BTX are obtained using a more acidic (H-ZSM-5 (23) and less acidic (H-ZSM-5 (80) and H-ZSM-5 (280)) catalyst.”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataIn ex situ pyrolysis, the ratio among individual aromatics depended slightly on conditions and catalyst, generally toluene > benzene > xylenes, with more benzene for Ga-impregnated catalysts.
“The ratio between the individual aromatics is slightly dependent on the conditions and catalyst used and in general seems to be toluene > benzene > xylenes but in the case of the Ga-impregnated catalysts higher amounts of benzene are formed.”
Quote in the paperNot a substantial claimProbably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationKraft black liquor is an aqueous solution containing lignin, tall oil, turpentine, depolymerized/oxidized hemicellulose fragments, and inorganic salts.
“The black liquor produced in this Kraft paper process consists of an aqueous solution of lignin, tall oil, turpentine, (depolymerized) oxidized (hemi)cellulose fragments, and inorganic salts.16”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [16] Sricharoenchaikul, 2009, Assessment of black liquor gasification in supercritical water, Bioresour. Technol. source
May combine two claims.
Interpretationown dataThe attractiveness of the ex situ process is supported by the lack of significant catalyst deactivation in the TMR and by unchanged activity/selectivity after 100 experiments with oxidative regeneration.
“The attractiveness of an ex situ process is supported by the observation that significant deactivation of the catalyst for the ex situ process was not observed (TMR) and after 100 experiments with intermittent oxidative regeneration to burn of the coke, the catalyst remained the same activity/selectivity.”
Quote in the paperSubstantial claimMay combine two claims.
InterpretationcitationThese catechol/pyrogallol intermediates are less stable than phenols and can defragment via quinones into smaller units that enter zeolite pores for aromatization.
“It is well-known that these intermediates are less stable than phenols and may defragment under the harsh conditions, via the corresponding quinones, in smaller units, able to enter the pores of the zeolite catalysts where the actual aromatization takes place (see Figure 8).40”
Quote in the paperSubstantial claim0 of 1 sources checked- cites [40] Asmadi, 2011, Thermal reactivities of catechols/pyrogallols and cresols/xylenols as lignin pyrolysis intermediates, J. Anal. Appl. Pyrolysis source
May combine two claims.
InterpretationreasoningSeparating pyrolysis from catalytic aromatization in an ex situ process avoids direct biomass-catalyst contact, which is especially advantageous for black liquor feeds and has greater commercial potential.
“In an ex situ process the pyrolysis is separated from the catalytic aromatization step, thereby avoiding direct contact between biomass and the catalyst. Especially using black liquors as a feed stock, the latter approach has more potential to be of commercial interest.”
Quote in the paperSubstantial claim- Rests on an assumption: Black liquor from paper mills contains high amounts of sodium and potassium.
May combine two claims.
InterpretationreasoningEx situ pyrolysis can be integrated into a paper mill because residual char can be co-fed to the recovery boiler, recycling inorganics and providing energy.
“The advantage of an ex situ process is that it can more easily be integrated in a paper mill as the residual char obtained after pyrolysis can be (co)fed to the recovery boiler. In this way the inorganics present in the char phase can be recycled to the paper mill and the char may be used for energy generation.”
Quote in the paperSubstantial claimMay combine two claims.
Interpretationown dataThe preliminary recycle experiment indicates that reversible coke deactivation is not a major problem and coke can be burned off easily.
“This preliminary experiment indicates that (i) reversible deactivation is not a major issue and the coke formed during reaction may be burned off easily”
Quote in the paperSubstantial claimProbably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationVarious biomass feedstocks, including lignins, have been identified as having potential to produce bio-aromatics.
“Various biomass feed-streams, including lignins, have been identified for their potential to produce bio-aromatics.10−15”
Quote in the paperNot a substantial claim0 of 6 sources checked- cites [10] Mihalcik, 2011, Screening acidic zeolites for catalytic fast pyrolysis of biomass and its components, J. Anal. Appl. Pyrolysis source
- cites [11] Ma, 2014, Selective deoxygenation of lignin during catalytic fast pyrolysis, Catal. Sci. Technol. source
- cites [12] Ma, 2012, Controlling the selectivity to chemicals from lignin via catalytic fast pyrolysis, Appl. Catal., A source
- cites [13] Jackson, 2009, Screening heterogeneous catalysts for the pyrolysis of lignin, J. Anal. Appl. Pyrolysis source
- cites [14] Mullen, 2010, Catalytic pyrolysis-GC/MS of lignin from several source.s, Fuel Process. Technol. source
- cites [15] Zhang, 2014, Catalytic fast pyrolysis of aspen lignin via Py-GC/MS, Fuel source
The paper relies on this without support.
No prior open or patent literature reports catalytic pyrolysis of crude black liquor to aromatics or BTX.
“To the best of our knowledge, no attempts in either the open and patent literature describe the catalytic pyrolysis of crude black liquor toward aromatics.”
“However, to the best of our knowledge, no attempts have been reported for the catalytic pyrolysis of black liquor, an important and high-volume lignin-containing stream of the paper industry, toward these essential building blocks for the chemical industry.”
The paper relies on this without support.
Black liquor from paper mills contains high amounts of sodium and potassium.
“As black liquor, originating from a paper mill, contains high amounts sodium and potassium, this may lead to a reduction of the acidity of the zeolite catalyst by H+/metal cation exchange, resulting in a lower conversion toward aromatics.”
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“Liquid industrial waste streams, such as black liquor 17 (from the pulp and paper industry) and crude glycerol 18 (from the biodiesel industry), have also been applied for bio-BTX synthesis.”
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- Authors
- Heeres, A., Schenk, N., Muizebelt, I., Blees, R., De Waele, B., Zeeuw, A.-J., Meyer, N., Carr, R., Wilbers, E., & Heeres, H. J.
- Affiliations
- BioBTX , De Mudden 14 , ,
- Huntsman , Everslaan 45 , , ,
- Huntsman (Belgium) (BE)
- University of Groningen (NL)
- Corresponding author
- Heeres, Hero Jan
- Venue
- ACS Sustainable Chemistry & Engineering
- Publisher
- American Chemical Society (ACS)
- Published
- 2018-02-01
- Volume
- 6
- Issue
- 3
- Pages
- 3472-3480
- ISSN
- 2168-0485 (ISSN-L)
- PMC
- PMC5871335
- OpenAlex
- W2786007903
- Semantic Scholar
- c707117e559be8d0ba80af1ca6919b56c1447946
- Cited by
- 63
- References
- 38
- Citations by year
- 2026: 5 · 2025: 5 · 2024: 7 · 2023: 12 · 2022: 16 · 2021: 6 · 2020: 6 · 2019: 6
- FWCI
- 1.80
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Locations
- ACS Sustainable Chemistry & Engineering (publishedVersion, cc-by-nc-nd)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- University of Groningen research database (University of Groningen / Centre for Information Technology) (publishedVersion, cc-by-nc-nd)
- Data Archiving and Networked Services (DANS) (submittedVersion, cc-by-nc-nd)
- University of Groningen research database (University of Groningen / Centre for Information Technology) (submittedVersion, cc-by-nc-nd)
- Topics
- Physical Sciences › Engineering › Biomedical Engineering › Thermochemical Biomass Conversion Processes
- Physical Sciences › Chemistry › Inorganic Chemistry › Zeolite Catalysis and Synthesis
- Physical Sciences › Engineering › Biomedical Engineering › Lignin and Wood Chemistry
- Keywords
- black liquor, catalytic pyrolysis, BTX, benzene, toluene, xylene, HZSM-5, gallium-modified zeolite, in situ catalysis, catalyst regeneration
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