{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,6]],"date-time":"2026-03-06T01:01:22Z","timestamp":1772758882661,"version":"3.50.1"},"reference-count":33,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2022,4,25]],"date-time":"2022-04-25T00:00:00Z","timestamp":1650844800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100009377","name":"Education Department of Hunan Province","doi-asserted-by":"publisher","award":["20B459"],"award-info":[{"award-number":["20B459"]}],"id":[{"id":"10.13039\/100009377","id-type":"DOI","asserted-by":"publisher"}]},{"name":"the Natural Science Foundation of Hunan Province","award":["2021JJ40430"],"award-info":[{"award-number":["2021JJ40430"]}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21776068"],"award-info":[{"award-number":["21776068"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100018681","name":"Huaihua University","doi-asserted-by":"publisher","award":["HHUY2020-08"],"award-info":[{"award-number":["HHUY2020-08"]}],"id":[{"id":"10.13039\/501100018681","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Nanomaterials"],"abstract":"<jats:p>Through the amination of oxidized activated carbon with ethylenediamine and then the adsorption of sulfuric acid, a strong carbon-based solid acid catalyst with hydrogen sulfate (denoted as AC-N-SO4H) was prepared, of which the surface acid density was 0.85 mmol\/g. The acetalization of benzaldehyde with ethylene glycol catalyzed by AC-N-SO4H was investigated. The optimized catalyst dosage accounted for 5 wt.% of the benzaldehyde mass, and the molar ratio of glycol to benzaldehyde was 1.75. After reacting such mixture at 80 \u00b0C for 5 h, the benzaldehyde was almost quantitatively converted into acetal; the conversion yield was up to 99.4%, and no byproduct was detected. It is surprising that the catalyst could be easily recovered and reused ten times without significant deactivation, with the conversion yield remaining above 99%. The catalyst also exhibited good substrate suitability for the acetalization of aliphatic aldehydes and the ketalization of ketones with different 1,2-diols.<\/jats:p>","DOI":"10.3390\/nano12091462","type":"journal-article","created":{"date-parts":[[2022,4,26]],"date-time":"2022-04-26T02:14:39Z","timestamp":1650939279000},"page":"1462","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Sulfuric Acid Immobilized on Activated Carbon Aminated with Ethylenediamine: An Efficient Reusable Catalyst for the Synthesis of Acetals (Ketals)"],"prefix":"10.3390","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8415-7272","authenticated-orcid":false,"given":"Wenzhu","family":"Liu","sequence":"first","affiliation":[{"name":"College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418000, China"},{"name":"National & Local Joint Engineering Laboratory for New Petro-Chemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha 410081, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ruike","family":"Guo","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418000, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Guanmin","family":"Peng","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418000, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dulin","family":"Yin","sequence":"additional","affiliation":[{"name":"National & Local Joint Engineering Laboratory for New Petro-Chemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha 410081, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,4,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"15849","DOI":"10.1021\/acs.joc.0c00395","article-title":"Acceleration and deceleration factors on the hydrolysis reaction of 4, 6-O-Benzylidene acetal group","volume":"85","author":"Maki","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1021\/cr0200769","article-title":"Protection (and deprotection) of functional groups in organic synthesis by heterogeneous catalysis","volume":"104","author":"Sartori","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2008","DOI":"10.1021\/acs.biomac.9b00215","article-title":"Spirocyclic acetal-modified dextran as a flexible ph-sensitive solubility-switching material","volume":"20","author":"Graham","year":"2019","journal-title":"Biomacromolecules"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1002\/asia.201901695","article-title":"Iron-catalyzed radical cleavage\/C\u2212C bond formation of acetal-derived alkylsilyl peroxides","volume":"15","author":"Shiozaki","year":"2020","journal-title":"Chem.-Asian J."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1779","DOI":"10.1039\/C4GC02377C","article-title":"Glycerol acetals and ketals as bio-based solvents: Positioning in Hansen and COSMO-RS spaces, volatility and stability towards hydrolysis and autoxidation","volume":"17","author":"Moity","year":"2015","journal-title":"Green Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5487","DOI":"10.1039\/D0GC01775B","article-title":"A transesterification\u2013acetalization catalytic tandem process for the functionalization of glycerol: The pivotal role of isopropenyl acetate","volume":"22","author":"Rigo","year":"2020","journal-title":"Green Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"118136","DOI":"10.1016\/j.apcata.2021.118136","article-title":"Highly active solid oxide acid catalyst for the synthesis of benzaldehyde glycol acetal","volume":"618","author":"Han","year":"2021","journal-title":"Appl. Catal. A Gen."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"4974","DOI":"10.1021\/acsomega.8b00159","article-title":"A simple and versatile method for the formation of acetals\/ketals using trace conventional acids","volume":"3","author":"Dong","year":"2018","journal-title":"ACS Omega"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1006\/jcat.2000.3044","article-title":"Zeolites for the production of fine chemicals: Synthesis of fructone fragrancy","volume":"196","author":"Climent","year":"2000","journal-title":"J. Catal."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"44946","DOI":"10.1039\/D0RA09087E","article-title":"Catalytic application of sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (SA-MNPs) for protection of aromatic carbonyl compounds and alcohols: Experimental and theoretical studies","volume":"10","author":"Khaef","year":"2020","journal-title":"RSC Adv."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.apcata.2014.08.001","article-title":"Heteropoly acid-based ionic liquids as effective catalysts for the synthesis of benzaldehyde glycol acetal","volume":"485","author":"Han","year":"2014","journal-title":"Appl. Catal. A Gen."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2341","DOI":"10.1002\/cssc.202100303","article-title":"Batch and continuous-flow preparation of biomass-derived furfural acetals over a TiO2 nanoparticle-exfoliated montmorillonite composite catalyst","volume":"14","author":"Zhou","year":"2021","journal-title":"ChemSusChem"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"26180","DOI":"10.1039\/C8RA04471F","article-title":"8-Hydroxy-2-methylquinoline-modified H4SiW12O40: A reusable heterogeneous catalyst for acetal\/ketal formation","volume":"8","author":"Liu","year":"2018","journal-title":"RSC Adv."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"106705","DOI":"10.1016\/j.fuproc.2020.106705","article-title":"Synthesis of bio-additive fuels from glycerol acetalization over a heterogeneous Ta\/W mixed addenda heteropolyacid catalyst","volume":"214","author":"Peng","year":"2021","journal-title":"Fuel Process. Technol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"117543","DOI":"10.1016\/j.apcata.2020.117543","article-title":"Pickering emulsions assisted synthesis of fatty acetal over phenyl sulfonic groups grafted on activated charcoal","volume":"597","author":"Xu","year":"2020","journal-title":"Appl. Catal. A Gen."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1016\/j.apcata.2009.10.027","article-title":"Esterification of oleic acid with ethanol by 12-tungstophosphoric acid supported on zirconia","volume":"372","author":"Oliveira","year":"2010","journal-title":"Appl. Catal. A Gen."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1016\/j.molcata.2004.11.024","article-title":"Direct synthesis, characterization and catalytic application of SBA-15 containing heteropolyacid H3PW12O40","volume":"229","author":"Yang","year":"2005","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.apcata.2016.04.023","article-title":"Manganese oxide-based catalysts for low-temperature selective catalytic reduction of NOx with NH3: A review","volume":"522","author":"Liu","year":"2016","journal-title":"Appl. Catal. A Gen."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"663","DOI":"10.3906\/kim-1810-63","article-title":"Investigation of sulfuric acid-treated activated carbon properties","volume":"43","author":"KOLUR","year":"2019","journal-title":"Turk. J. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1016\/j.carbon.2016.02.015","article-title":"Functionalization of activated carbons by HNO3 treatment: Influence of phosphorus surface groups","volume":"101","author":"Rosas","year":"2016","journal-title":"Carbon"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"127496","DOI":"10.1016\/j.chemosphere.2020.127496","article-title":"Enrichment of surface oxygen functionalities on activated carbon for adsorptive removal of sevoflurane","volume":"260","author":"Ang","year":"2020","journal-title":"Chemosphere"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"11576","DOI":"10.1021\/acs.chemrev.9b00199","article-title":"SO3H-containing functional carbon materials: Synthesis, structure, and acid catalysis","volume":"119","author":"Konwar","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2886","DOI":"10.1021\/acscatal.5b00375","article-title":"Nitrogen-doped, metal-free activated carbon catalysts for aerobic oxidation of alcohols","volume":"5","author":"Watanabe","year":"2015","journal-title":"Acs Catal."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/j.biombioe.2017.01.015","article-title":"Carbon dioxide capture using ammonium sulfate surface modified activated biomass carbon","volume":"98","author":"Yadavalli","year":"2017","journal-title":"Biomass Bioenergy"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1556","DOI":"10.1002\/cplu.201500293","article-title":"Chitin-derived mesoporous, nitrogen-containing carbon for heavy-metal removal and styrene epoxidation","volume":"80","author":"Gao","year":"2015","journal-title":"ChemPlusChem"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"3544","DOI":"10.1080\/09593330.2019.1615131","article-title":"Preparation and evaluation of nitrogen-tailored hierarchical meso-\/micro-porous activated carbon for CO2 adsorption","volume":"41","author":"Zhang","year":"2020","journal-title":"Environ. Technol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"109846","DOI":"10.1016\/j.jpcs.2020.109846","article-title":"New approach for sulfonation of carbonaceous materials: Highly efficient solid acid catalysts for benzaldehyde acetalization with ethylene glycol","volume":"150","author":"Hosseini","year":"2021","journal-title":"J. Phys. Chem. Solids"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1092","DOI":"10.1016\/j.renene.2019.11.108","article-title":"Propyl-SO3H functionalized graphene oxide as multipurpose solid acid catalyst for biodiesel synthesis and acid-catalyzed esterification and acetalization reactions","volume":"151","author":"Hosseini","year":"2020","journal-title":"Renew. Energy"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2079","DOI":"10.1016\/j.cclet.2020.11.027","article-title":"Sulfonic acid-functionalized core-shell Fe3O4@carbon microspheres as magnetically recyclable solid acid catalysts","volume":"32","author":"Yuan","year":"2021","journal-title":"Chin. Chem. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"23716","DOI":"10.1039\/C5TA05605E","article-title":"Al-coordination polymer-derived nanoporous nitrogen-doped carbon microfibers as metal-free catalysts for oxygen electroreduction and acetalization reactions","volume":"3","author":"Han","year":"2015","journal-title":"J. Mater. Chem. A"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.molcata.2011.08.005","article-title":"Acetalization of carbonyl compounds catalyzed by acidic ionic liquid immobilized on silica gel","volume":"348","author":"Miao","year":"2011","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1039\/C8RA09457H","article-title":"Imidazolyl activated carbon refluxed with ethanediamine as reusable heterogeneous catalysts for Michael addition","volume":"9","author":"Liu","year":"2019","journal-title":"RSC Adv."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3749","DOI":"10.1021\/cs5008206","article-title":"Highly selective two-electron oxygen reduction catalyzed by mesoporous nitrogen-doped carbon","volume":"4","author":"Park","year":"2014","journal-title":"ACS Catal."}],"container-title":["Nanomaterials"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2079-4991\/12\/9\/1462\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:00:58Z","timestamp":1760137258000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2079-4991\/12\/9\/1462"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,25]]},"references-count":33,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2022,5]]}},"alternative-id":["nano12091462"],"URL":"https:\/\/doi.org\/10.3390\/nano12091462","relation":{},"ISSN":["2079-4991"],"issn-type":[{"value":"2079-4991","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,25]]}}}