TiO2@TDI@DMAPA: an amine-modified nanoparticle, tailored to act as an economic basic heterogeneous nanocatalyst
Source abstract
Abstract
This study has represented an easy and inexpensive method for the synthesis of a new basic nanocatalyst. In this regard, 3-dimethylaminopropylamine (DMAPA), an economic, industrial, and readily obtainable basic compound, has been grafted onto nano-titania particles by the use of 2,4-toluene diisocyanate (TDI) as a bi-functional, inexpensive, and highly reactive linker. The prepared catalyst has been characterized using the spectroscopic FT-IR method, XRD, FE-SEM, EDX, and back titration. Furthermore, it was identified as an effective catalyst in the preparation of DHPM derivatives and pyranopyrazoles which results in high purity and high yields of products. Response surface methodology (RSM) based on a central composite design (CCD) was employed to reach the optimal conditions. The catalyst can be readily separated and recycled up to six times.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Multicomponent Synthesis of Heterocycles · Chemical Synthesis and Reactions · Synthesis and biological activity
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (76)
Show source-provided references
1. Akbari A (2015) Ca (OH) 2/CaO as a green catalyst for the synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones derivatives. Iran JOC 7:1649–1653
2. Allef P, Begoihn U, Grüning B, Klein R, Peggau J (2007) Process for the preparation of highly concentrated flowable aqueous solutions of betaines. US Patent 7297675 B2, 20 Nov
3. Amoozadeh A, Rahmani S (2015) Nano-WO 3-supported sulfonic acid: new, efficient and high reusable heterogeneous nano catalyst. J Mol Catal A Chem 396:96–107. https://doi.org/10.1016/j.molcata.2014.09.02010.1016/j.molcata.2014.09.020 ↗
4. Amoozadeh A, Golian S, Rahmani S (2015) TiO 2-coated magnetite nanoparticle-supported sulfonic acid as a new, efficient, magnetically separable and reusable heterogeneous solid acid catalyst for multicomponent reactions. RSC Adv 5:45974–45982. https://doi.org/10.1039/C5RA06515A10.1039/C5RA06515A ↗
5. Amoozadeh A, Rahmani S, Bitaraf M, Abadi FB, Tabrizian E (2016) Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: a new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions. New J Chem 40:770–780. https://doi.org/10.1039/C5NJ02430G10.1039/C5NJ02430G ↗
6. Bouzina Z, Mokbel I, Negadi A, Jose J, Negadi L (2016) Phase equilibrium measurements and thermodynamic modeling of aqueous solutions of polyamines CO 2 absorbents: 3-aminopropylmethylamine, 3-aminopropyldimethylamine and N, N-diethyl 1, 3-propanediamine at temperatures from 273K to 363K. J Chem Thermodyn 92:43–54. https://doi.org/10.1016/j.jct.2015.08.02310.1016/j.jct.2015.08.023 ↗
7. Brunn C, Behler A, Stanislowski D, Barbenheim M (2015) Aqueous surfactant compositions. US Patent 20170007520 A1, 12 Jan
8. Buyse K, Moonen K (2012) Agricultural and detergent compositions containing a tertiary amide as adjuvant or as surfactant. US Patent 20140080708 A1, 20 Mar
9. Chen X, Peng Y (2008) Chloroferrate (III) ionic liquid: efficient and recyclable catalyst for solvent-free synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. Catal Lett 122:310–313. https://doi.org/10.1007/s10562-007-9377-110.1007/s10562-007-9377-1 ↗
10. Cosimbescu L, Robinson JW, Zhou Y, Qu J (2016) Dual functional star polymers for lubricants. RSC Adv 6:86259–86268. https://doi.org/10.1039/C6RA17461B10.1039/C6RA17461B ↗
11. Dai Y, Wang H, Zhang X (2017) Reduction-responsive interlayer-crosslinked micelles prepared from star-shaped copolymer via click chemistry for drug controlled release. J Nanopart Res 19:383. https://doi.org/10.1007/s11051-017-4082-510.1007/s11051-017-4082-5 ↗
12. de Fátima Â, Braga TC, LDS N, Terra BS, Oliveira BG, da Silva DL, Modolo LV (2015) A mini-review on Biginelli adducts with notable pharmacological properties. J Adv Res 6:363–373. https://doi.org/10.1016/j.jare.2014.10.00610.1016/j.jare.2014.10.006 ↗
13. Dong K et al (2017) Highly active and efficient catalysts for alkoxycarbonylation of alkenes. Nat Commun 8:14117. https://doi.org/10.1038/ncomms1411710.1038/ncomms14117 ↗
14. Ernst M, Oehlenschläger S, Kuhnke F, Roβ K-H, Deeg R, Melder J-P (2010) Process for the synthesis of DMAPA. US Patent 7723547 B2, 25 May
15. Fairlamb IJ, Marrison LR, Dickinson JM, Lu F-J, Schmidt JP (2004) 2-Pyrones possessing antimicrobial and cytotoxic activities. Bioorg Med Chem 12:4285–4299. https://doi.org/10.1016/j.bmc.2004.01.05110.1016/j.bmc.2004.01.051 ↗
16. Fihri A, Len C, Varma RS, Solhy A (2017) Hydroxyapatite: a review of syntheses, structure and applications in heterogeneous catalysis. Coord Chem Rev 347:48–76. https://doi.org/10.1016/j.ccr.2017.06.00910.1016/j.ccr.2017.06.009 ↗
17. Frederich N, Nysten B, Muls B, Hofkens J, Jiwan J-LH, Jonas AM (2008) Nano-patterned layers of a grafted coumarinic chromophore. Photochem Photobiol Sci 7:460–466. https://doi.org/10.1039/B717309A10.1039/b717309a ↗
18. Friend CM, Xu B (2017) Heterogeneous catalysis: a central science for a sustainable future. Acc Chem Res 50:517–521. https://doi.org/10.1021/acs.accounts.6b0051010.1021/acs.accounts.6b00510 ↗
19. Godard N, Vivian A, Fusaro L, Cannavicci L, Aprile C, Debecker DP (2017) High-yield synthesis of ethyl lactate with mesoporous tin silicate catalysts prepared by an aerosol-assisted sol–gel process. ChemCatChem 9:2211–2218. https://doi.org/10.1002/cctc.20160163710.1002/cctc.201601637 ↗
20. Gruar RI, Tighe CJ, Southern P, Pankhurst QA, Darr JA (2015) A direct and continuous supercritical water process for the synthesis of surface-functionalized nanoparticles. Ind Eng Chem Res 54:7436–7451. https://doi.org/10.1021/acs.iecr.5b0181710.1021/acs.iecr.5b01817 ↗
21. Ishii K, Tanaka Y (2009) Aerosol cosmetic composition. US Patent 7481996 B2, 27 Jan
22. Kappe CO (2000) Biologically active dihydropyrimidones of the Biginelli-type—a literature survey. Eur J Med Chem 35:1043–1052. https://doi.org/10.1016/S0223-5234(00)01189-210.1016/S0223-5234(00)01189-2 ↗
23. Kim K, Kim MP, Lee W-G (2017) Preparation and evaluation of mesoporous carbon derived from waste materials for hybrid-type Li–air batteries. New J Chem 41:8864–8869. https://doi.org/10.1039/C7NJ00863E10.1039/C7NJ00863E ↗
24. Kiyani H, Samimi H, Ghorbani F, Esmaieli S (2013) One-pot, four-component synthesis of pyrano [2, 3-c] pyrazoles catalyzed by sodium benzoate in aqueous medium. CCL 2:197–206. https://doi.org/10.5267/j.ccl.2013.07.00210.5267/j.ccl.2013.07.002 ↗
25. Kjellin M, Johansson I (2010) Surfactants from renewable resources vol 1, 1st edn. Wiley, Chichester10.1002/9780470686607 ↗
26. Koshti NM, Parab BB, Nashte SS (2008) Aqueous composition of a betaine with solids content of at least 45% by weight. US Patent 7384898 B2, 10 Jun
27. Kumar A, Maurya RA (2007) An efficient bakers’ yeast catalyzed synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones. Tetrahedron Lett 48:4569–4571. https://doi.org/10.1016/j.tetlet.2007.04.13010.1016/j.tetlet.2007.04.130 ↗
28. Kunz S (2016) Supported, ligand-functionalized nanoparticles: an attempt to rationalize the application and potential of ligands in heterogeneous catalysis. Top Catal 59:1671–1685. https://doi.org/10.1007/s11244-016-0687-710.1007/s11244-016-0687-7 ↗
29. Lavacchi A, Miller H, Vizza F (2013) Nanotechnology in electrocatalysis for energy, vol 170, 1st edn. Springer, New York. https://doi.org/10.1007/978-1-4899-8059-510.1007/978-1-4899-8059-5 ↗
30. Li G, Xiao J, Zhang W (2011) Knoevenagel condensation catalyzed by a tertiary-amine functionalized polyacrylonitrile fiber. Green Chem 13:1828–1836. https://doi.org/10.1039/C0GC00877J10.1039/c0gc00877j ↗
31. Lu J, Bai Y (2002) Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates. One-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. Synthesis 2002:0466–0470. https://doi.org/10.1055/s-2002-2095610.1055/s-2002-20956 ↗
32. Mägerlein W, Eberhardt J, Melder J-P, Köhler U, Hahn T, Kreitschmann M, Herbrecht D (2014) DMAPN having a low DGN content and a process for preparing DMAPA having a low DGN content. US Patent 8710269 B2, 29 Apr
33. Makawana JA, Mungra DC, Patel MP, Patel RG (2011) Microwave assisted synthesis and antimicrobial evaluation of new fused pyran derivatives bearing 2-morpholinoquinoline nucleus. Bioorg Med Chem Lett 21:6166–6169. https://doi.org/10.1016/j.bmcl.2011.07.12310.1016/j.bmcl.2011.07.123 ↗
34. Mandha SR, Siliveri S, Alla M, Bommena VR, Bommineni MR, Balasubramanian S (2012) Eco-friendly synthesis and biological evaluation of substituted pyrano [2, 3-c] pyrazoles. Bioorg Med Chem Lett 22:5272–5278. https://doi.org/10.1016/j.bmcl.2012.06.05510.1016/j.bmcl.2012.06.055 ↗
35. Manos-Turvey A, Al-Ashtal HA, Needham PG, Hartline CB, Prichard MN, Wipf P, Brodsky JL (2016) Dihydropyrimidinones and-thiones with improved activity against human polyomavirus family members. Bioorg Med Chem Lett 26:5087–5091. https://doi.org/10.1016/j.bmcl.2016.08.08010.1016/j.bmcl.2016.08.080 ↗
36. Mansoor SS, Shafi SS, Ahmed SZ (2016) An efficient one-pot multicomponent synthesis of 3, 4-dihydropyrimidine-2-(1H)-ones/thiones/imines via a Lewis base catalyzed Biginelli-type reaction under solvent-free conditions. Arab J Chem 9:S846–S851. https://doi.org/10.1016/j.arabjc.2011.09.01810.1016/j.arabjc.2011.09.018 ↗
37. Mao L, Wu Y, Stoumpos CC, Wasielewski MR, Kanatzidis MG (2017) White-light emission and structural distortion in new corrugated two-dimensional lead bromide perovskites. J Am Chem Soc 139:5210–5215. https://doi.org/10.1021/jacs.7b0131210.1021/jacs.7b01312 ↗
38. Mecadon H, Rohman MR, Rajbangshi M, Myrboh B (2011) γ-Alumina as a recyclable catalyst for the four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2, 4-dihydropyrano [2, 3-c] pyrazole-5-carbonitriles in aqueous medium. Tetrahedron Lett 52:2523–2525. https://doi.org/10.1016/j.tetlet.2011.03.03610.1016/j.tetlet.2011.03.036 ↗
39. Mehta A, Mishra A, Sharma M, Singh S, Basu S (2016) Effect of silica/titania ratio on enhanced photooxidation of industrial hazardous materials by microwave treated mesoporous SBA-15/TiO2 nanocomposites. J Nanopart Res 18:209. https://doi.org/10.1007/s11051-016-3523-x10.1007/s11051-016-3523-x ↗
40. Mohammadipour M, Amoozadeh A (2017) The synthesis of polyhydroacridines by covalent 5-sulfobenzoic acid-functionalized graphene oxide as a novel, green, efficient, and heterogeneous catalyst. Monatsh Chem 148:1075–1084. https://doi.org/10.1007/s00706-016-1876-610.1007/s00706-016-1876-6 ↗
41. Molinari V, Giordano C, Antonietti M, Esposito D (2014) Titanium nitride-nickel nanocomposite as heterogeneous catalyst for the hydrogenolysis of aryl ethers. J Am Chem Soc 136:1758–1761. https://doi.org/10.1021/ja411941210.1021/ja4119412 ↗
42. Moradi-Shoeili Z, Zare M, Bagherzadeh M (2016) Synthesis and characterization of magnetic silica-supported Mn (II)-substituted polyoxophosphotungstate as catalyst in sulfoxidation reaction. J Nanopart Res 18:298. https://doi.org/10.1007/s11051-016-3609-510.1007/s11051-016-3609-5 ↗
43. Nasr MN, Gineinah MM (2002) Pyrido [2, 3-d] pyrimidines and pyrimido [5′, 4′: 5, 6] pyrido [2, 3-d] pyrimidines as new antiviral agents: synthesis and biological activity. Arch Pharm 335:289–295. https://doi.org/10.1002/1521-4184(200208)335:6<289::AID-ARDP289>3.0.CO;2-Z10.1002/1521-4184(200208)335:6<289::AID-ARDP289>3.0.CO;2-Z ↗
44. O'Lenick Jr AJ, LaVay C (2006) Raspberry amido amines and betaines as a delivery system for natural antioxidants. US Patent 7078545 B1, 18 Jul
45. O'Lenick Jr AJ, O'Lenick TG, O'Lenick KA (2005) Dimer amidopropyl dimethyl betaines. US Patent 6979744 B1, 27 Dec
46. Otokesh S, Kolvari E, Amoozadeh A, Koukabi N (2015) Magnetic nanoparticle-supported imidazole tribromide: a green, mild, recyclable and metal-free catalyst for the oxidation of sulfides to sulfoxides in the presence of aqueous hydrogen peroxide. RSC Adv 5:53749–53756. https://doi.org/10.1039/C5RA07530K10.1039/C5RA07530K ↗
47. Ou B, Li D, Liu Y (2009) Compatibilizing effect of maleated polypropylene on the mechanical properties of injection molded polypropylene/polyamide 6/functionalized-TiO 2 nanocomposites. Compos Sci Technol 69:421–426. https://doi.org/10.1016/j.compscitech.2008.11.01010.1016/j.compscitech.2008.11.010 ↗
48. Ou B, Li D, Liu Q, Zhou Z, Chen G, Liu P (2012) Preparation of conductive polyaniline/functionalized titanium dioxide nanocomposites via graft polymerization. J Macromol Sci 49:149–153. https://doi.org/10.1080/10601325.2012.64221210.1080/10601325.2012.642212 ↗
49. Patil AO (1996) Fuel and lubricant additives derived from dihydroxy-aromatic compounds. US Patent 5576274 A, 19 Nov
50. Peffly MM, Brown MA, Staudigel JA, Zhang JJ (2016) Personal care compositions containing cationic synthetic copolymer and a detersive surfactant. US Patent 9427391 B2, 30 Aug
51. Peña L, Xu F, Hohn KL, Li J, Wang D (2014) Propyl-sulfonic acid functionalized nanoparticles as catalyst for pretreatment of corn stover. J Biomater Nanobiotechnol 5:8. https://doi.org/10.4236/jbnb.2014.5100210.4236/jbnb.2014.51002 ↗
52. Quan H, Zhang X, Lu H, Huang Z (2012) Synthesis and acid solution properties of a novel betaine zwitterionic surfactant. Open Chem 10:1624–1632. https://doi.org/10.2478/s11532-012-0084-410.2478/s11532-012-0084-4 ↗
53. Rahmani S, Amoozadeh A, Kolvari E (2014) Nano titania-supported sulfonic acid: an efficient and reusable catalyst for a range of organic reactions under solvent free conditions. Catal Commun 56:184–188. https://doi.org/10.1016/j.catcom.2014.07.00210.1016/j.catcom.2014.07.002 ↗
54. Rodina A et al (2007) Selective compounds define Hsp90 as a major inhibitor of apoptosis in small-cell lung cancer. Nat Chem Biol 3:498–507. https://doi.org/10.1038/nchembio.2007.1010.1038/nchembio.2007.10 ↗
55. Salehi P, Dabiri M, Zolfigol MA, Fard MAB (2003) Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. Tetrahedron Lett 44:2889–2891. https://doi.org/10.1016/S0040-4039(03)00436-210.1016/S0040-4039(03)00436-2 ↗
56. Salinas B, Ruiz-Cabello J, Lechuga-Vieco AV, Benito M, Herranz F (2015) Surface-functionalized nanoparticles by olefin metathesis: a chemoselective approach for in vivo characterization of atherosclerosis plaque. Chem Eur J 21:10450–10456. https://doi.org/10.1002/chem.20150045810.1002/chem.201500458 ↗
57. Schröder K, Matyjaszewski K, Noonan KJ, Mathers RT (2014) Towards sustainable polymer chemistry with homogeneous metal-based catalysts. Green Chem 16:1673–1686. https://doi.org/10.1039/C3GC42159G10.1039/C3GC42159G ↗
58. Schrott A, Cox E (2017) Rinse-off volumizing hair compositions containing styling polymers and polycationic polymers. US Patent 9662292 B2, 30 May
59. Shaban SM, Aiad I, Fetouh HA, Maher A (2015) Amidoamine double tailed cationic surfactant based on dimethylaminopropylamine: synthesis, characterization and evaluation as biocide. J Mol Liq 212:699–707. https://doi.org/10.1016/j.molliq.2015.10.02410.1016/j.molliq.2015.10.024 ↗
60. Shamsi T, Amoozadeh A, Tabrizian E, Sajjadi SM (2017) A new zwitterionic nano-titania supported Keggin phosphotungstic heteropolyacid: an efficient and recyclable heterogeneous nanocatalyst for the synthesis of 2, 4, 5-triaryl substituted imidazoles. React Kinet Mech Catal 121:505–522. https://doi.org/10.1007/s11144-017-1177-z10.1007/s11144-017-1177-z ↗
61. Shehata MR, Shoukry MM, Ragab MS (2012) Synthesis and structural characterization of Pd (N, N-dimethylaminopropylamine) Cl 2 complex—the interaction with bio-relevant ligands with reference to the effect of cysteine on the deactivation of metal-based drug. Spectrochim Acta Mol Biomol Spectrosc 96:809–814. https://doi.org/10.1016/j.saa.2012.07.10110.1016/j.saa.2012.07.101 ↗
62. Soliman AM, Mohamed SK, El-Remaily M, Ali AEAA, Abdel-Ghany H (2014) Synthesis of pyrimidine, dihydropyrimidinone, and dihydroimidazole derivatives under free solvent conditions and their antibacterial evaluation. J Heterocyclic Chem 51:1202–1209. https://doi.org/10.1002/jhet.165710.1002/jhet.1657 ↗
63. Solymosi F, Raskó J (1980) An infrared study on the formation of isocyanate in the NO+ CO reaction on supported Ir catalyst. J Catal 63:217–225. https://doi.org/10.1016/0021-9517(80)90074-310.1016/0021-9517(80)90074-3 ↗
64. Tabrizian E, Amoozadeh A (2016a) A new type of SO 3 H-functionalized magnetic-titania as a robust magnetically-recoverable solid acid nanocatalyst for multi-component reactions. RSC Adv 6:96606–96615. https://doi.org/10.1039/C6RA21048A10.1039/C6RA21048A ↗
65. Tabrizian E, Amoozadeh A (2016b) A unique approach to magnetization of metal oxides: nano-Fe 3 O 4@ TDI@ TiO 2 as a highly efficient, magnetically separable and recyclable heterogeneous nanocatalyst. Catal Sci Technol 6:6267–6276. https://doi.org/10.1039/C6CY00316H10.1039/C6CY00316H ↗
66. Tabrizian E, Amoozadeh A, Rahmani S (2016a) Sulfamic acid-functionalized nano-titanium dioxide as an efficient, mild and highly recyclable solid acid nanocatalyst for chemoselective oxidation of sulfides and thiols. RSC Adv 6:21854–21864. https://doi.org/10.1039/C5RA20507G10.1039/C5RA20507G ↗
67. Tabrizian E, Amoozadeh A, Shamsi T (2016b) A novel class of heterogeneous catalysts based on toluene diisocyanate: the first amine-functionalized nano-titanium dioxide as a mild and highly recyclable solid nanocatalyst for the Biginelli reaction. React Kinet Mech Catal 119:245–258. https://doi.org/10.1007/s11144-016-1047-010.1007/s11144-016-1047-0 ↗
68. Tasker SZ, Standley EA, Jamison TF (2014) Recent advances in nickel catalysis. Nature 509:–299. https://doi.org/10.1038/nature1327410.1038/nature13274 ↗
69. Tu S, Fang F, Miao C, Jiang H, Feng Y, Shi D, Wang X (2003) One-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones using boric acid as catalyst. Tetrahedron Lett 44:6153–6155. https://doi.org/10.1016/S0040-4039(03)01466-710.1016/S0040-4039(03)01466-7 ↗
70. Utreja D (2014) Synthesis and antifungal activity of dihydropyrimidinones and their derivatives. PhD diss, Punjab Agricultural University Ludhiana
71. Wang W, Hua H, Yin L, He Y (2014) Influence of the hydrophobic groups on quaternary ammonium additives for copper electrodeposition. J Electrochem Soc 161:D651–D656. https://doi.org/10.1149/2.0381412jes10.1149/2.0381412jes ↗
72. Ward GJ, Blanchard BC (2003) Low pressure process for manufacture of 3-dimethylaminopropylamine (DMAPA). US Patent 6660887 B1, 9 Dec
73. Wu S, Peng S, Hameed N, Guo Q, Mai Y-W (2012) A new route to nanostructured thermosets with block ionomer complexes. Soft Matter 8:688–698. https://doi.org/10.1039/C1SM06244A10.1039/C1SM06244A ↗
74. Zhang L, Guo Y, Iqbal A, Li B, Deng M, Gong D, Liu W, Qin W (2017) Palladium nanoparticles as catalysts for reduction of Cr(VI) and Suzuki coupling reaction. J Nanopart Res 19:150. https://doi.org/10.1007/s11051-017-3829-310.1007/s11051-017-3829-3 ↗
75. Zou W, Zhang J-L, Chen F, Anpo M, He D-N (2009) A simple approach for preparing a visible-light TiO2 photocatalyst. Res Chem Intermed 35:717. https://doi.org/10.1007/s11164-009-0093-x10.1007/s11164-009-0093-x ↗
76. Zumpe FL, Flüß M, Schmitz K, Lender A (2007) Propane phosphonic acid anhydride: a new promoter for the one-pot Biginelli synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. Tetrahedron Lett 48:1421–1423. https://doi.org/10.1016/j.tetlet.2006.12.09810.1016/j.tetlet.2006.12.098 ↗