P toluenesulfonic acid

The following chemical reagents were used in the procedures described below for the synthesis of KIT-5 materials: Pluronic F127 (ethylene oxide and propylene oxide triblock copolymer EO₁₀₆PO₇₀EO₁₀₆, BASF, Ludwigshafen am Rhein, Germany), tetraethyl orthosilicate, TEOS (≥99%, Sigma-Aldrich, Darmstadt, Germany), 3-mercapropyltrimethoxysilane, MPTMS (95%, abcr GmbH, Karlsruhe, Germany), hydrochloric acid (37.3%, POCh, Gliwice, Poland), ethyl alcohol 96% (POCh, Gliwice, Poland), toluene (Chempur, Piekary Śląskie, Poland), and chloroform (98.5%, POCh, Gliwice, Poland). For the analysis of active acidic centres in the synthesized materials: sodium hydroxide (0.01 M, test portion, Chempur, Piekary Śląskie, Poland), sulphuric acid(VI) (0.005 M, test portion, Merck, Darmstadt, Germany) were used. In the Friedel–Crafts alkylation reaction the following materials were used: anisole (99%, Sigma-Aldrich, Darmstadt, Germany), benzyl alcohol (Ph Eur, Fluka Analytical, Darmstadt, Germany), n-decane (>94%, Merck, Darmstadt, Germany). Commercially available non-mesoporous silica (Sigma-Aldrich, Darmstadt, Germany) was used as a reference material in the heterogeneous catalytic tests, while p-toluenesulfonic acid, PTSA (≥98.5%, Sigma-Aldrich, Darmstadt, Germany) was used as a homogeneous catalyst.

Trans-cinnamic acid (purity ≥99%), p-cumaric acid (purity ≥98%), trans-ferulic acid (purity ≥99%), 1-decanol (purity 99%), p-toluenesulfonic acid, anhydrous toluene, luminol, H₂O₂, Tris-HCl buffer, lucigenin, xanthine, and xanthine oxidase were purchased from Sigma-Aldrich (St. Louis, Missouri, USA). DPPP was purchased from Cayman Chemical Co., Ann Arbor, MI, USA. Ethyl acetate, cyclohexane, ethanol, and potassium hydroxide (KOH) were purchased from Carlo Erba (Cornaredo, MI, Italy). Polysorbate 80 and phenolphthalein were purchased from A.C.E.F. (Fiorenzuola d’Arda, PC, Italy). Nigella oil from black cumin (Nigella sativa L.) seeds was produced by Tre Ponti Snr company (Polverigi, AN, Italy). Extra-virgin olive (EVO) oil from the Raggia cultivar of olive drupes (Olea europaea L.) was produced in a local olive mill. Chemical characterization of the EVO oil and Nigella oils has been reported in previous works [16 (link)].

Sucrose and diisopropyl azodicarboxylate (DIAD) were purchased from Fluorochem (Hadfield, UK). Triphenylphosphine (PPh₃) and oxalyl chloride [(CO)₂Cl₂] were purchased from Alpha Aesar (Ward Hill, MA, USA). Lactose monohydrate, p-toluene sulfonic acid, 2,2-dimethoxypropane, tetrafluoro boric acid diethyl ether complex [HBF₄^.Et₂O], phenylacetic acid, p-biphenyl acetic acid, p-phenyl benzoic acid, acetone [CH₃C(O)CH₃], dimethylformamide (DMF), dimethyl sulfoxide (DMSO), methanol (CH₃OH), and methylene chloride (CH₂Cl₂) were purchased from Sigma-Aldrich (Milan, Italy).

Acryloyl chloride (97%), crotonic acid (98%), itaconic acid (IA, 97%), methyl acrylate (99%), methyl crotonate (98%), succinic acid (SA, 99%), p-toluenesulfonic acid, phenothiazine (98%), zinc iodide (98%), and boron trifluoride diethyl etherate (46%) were purchased from Sigma-Aldrich and used as received. Isosorbide (98%) and E-benzaldoxime (97%) were purchased from Alfa Aesar, and Isosorbide was recrystallized from acetone/ethyl acetate. All used solvents are commercially available and were used without further purification.

Bagasse was obtained from a local sugar factory (Guangxi, China). It was dried, screened and crushed. We obtained 60-mesh bagasse powders. The chemical composition was analyzed using National Renewable Energy Laboratory methods. The specific steps and methods are described by Ge and collaborators [3 (link)]. The contents of cellulose, hemicellulose and lignin were 46.69%, 19.81% and 21.33%, respectively. p-toluenesulfonic acid was purchased from Sigma-Aldrich (Shanghai, China). Other analytical chemicals were purchased from Aladdin (Shanghai, China).