Abstract
Vapor phase methylation of phenol with methanol is widely carried out to produce a variety of products such as anisole, cresols and xylenols due to their increasing application in industries. Numerous researches have been carried out to understand the mechanistic behavior of phenol methylation. Based on discussion of reaction mechanism, the present article covered methylation of phenol with methanol over various catalysts, including zeolites, metal oxides, spinel, phosphates, sulfates, hydrotalcites and others. Moreover, the influence of reaction conditions and catalyst deactivation behavior were described. Finally, this review paper gives useful insights for the future direction of phenol methylation with methanol.
Graphical Abstract
This review provides a summary for the process of phenol methylation with methanol: catalysts, reaction mechanism and deactivated behavior, etc.
Similar content being viewed by others
References
Cavani F, Maselli L, Passeri S, Lercher JA (2010) J Catal 269(2):340–350
Devassy BM, Shanbhag GV, Lefebvre F, Halligudi SB (2004) J Mol Catal A-Chem 210(1–2):125–130
Renaud M, Chantal PD, Kaliaguine S (1986) Can J Chem Eng 64(5):787–791
Lewis HF, Shaffer S, Trieschmann W, Cogan H (1930) Ind eng chem 22(1):34–36
Clark JH (1999) Green Chem 1(1):1–8
Kocal JA, Vora BV, Imai T (2001) Appl Catal A 221(1–2):295–301
Bal R, Mayadevi S, Sivasanker S (2003) Org Process Res Dev 7(1):17–21
Jafari AA, Khodadadi A, Mortazavi Y (2013) J Mol Catal A 372:79–83
Bal R, Tope BB, Sivasanker S (2002) J Mol Catal A 181(1–2):161–171
Xie J, Zhuang W, Yan N, Du Y, Xi S, Zhang W, Tang J, Zhou Y, Wang J (2017) Chem Eng J 328:1031–1042
Devi GS, Giridhar D, Reddy BM (2002) J Mol Catal A 181(1–2):173–178
Kirichenko GN, Glazunova VI, Balaev AV, Dzhemilev UM (2008) Pet Chem 48(5):389–392
Lazar K, Mathew T, Koppany Z, Megyeri J, Samuel V, Mirajkar SP, Rao BS, Guczi L (2002) Phys Chem Chem Phys 4(14):3530–3536
Beltrame P, Beltrame PL, Carniti P, Castelli A, Forni L (1987) Appl Catal 29(2):327–334
Bhongale P, Joshi S, Mali N (2021) Catal Rev Sci Eng (6):1–46.
Bautista FM, Campelo JM, Garcia A, Luna D, Marinas JM, Romero A, Navio JA, Macias M (1993) Appl Catal A 24(40):161–173
Santacesaria E, Grasso D, Gelosa D, Carrá S (1990) Appl Catal 64:83–99
Chantal PD, Kaliaguine S, Grandmaison JL (1985) Appl Catal 18(1):133–145
Sad ME, Padro CL, Apesteguia CR (2008) Catal Today 133(1):720–728
Marczewski M, Bodibo JP, Perot G, Guisnet M (1989) J Mol Catal 50(2):211–218
Grabowska H, Kaczmarczyk W, Wrzyszcz J (1989) Appl Catal 47(2):351–355
Klimkiewicz R, Grabowska H, Teterycz H (2003) Appl Catal A 246(1):125–136
Wolska J, Przepiera K, Grabowska H, Przepiera A, Jabloski M, Klimkiewicz R (2008) Res Chem Intermed 34(1):43–51
Grabowska H, Mista W, Trawczynski J, Wrzyszcz J, Zawadzki M (2001) Res Chem Intermed 27(3):305–313
Santacesaria E, Diserio M, Ciambelli P, Gelosa D, Carra S (1990) Appl Catal 64(1–2):101–117
Sad ME, Padro CL, Apesteguia CR (2008) Appl Catal A 342(1–2):40–48
Ballarini N, Cavani F, Maselli L, Montaletti A, Passeri S, Scagliarini D, Flego C, Perego C (2007) J Catal 251(2):423–436
Chary KVR, Ramesh K, Naresh D, Rao PVR, Rao AR, Rao VV (2009) Catal Today 141(1–2):187–194
Wang Y, Song Y, Huo W, Jia M, Jing X, Yang P, Yang Z, Liu G, Zhang W (2012) Chem Eng J 181:630–635
Velu S, Swamy CS (1997) Appl Catal A 162(1–2):81–91
Velu S, Swamy CS (1996) Appl Catal A 145(1–2):141–153
Bezouhanova C, Alzihari MA (1992) Appl Catal A 83(1):45–49
Kotanigawa T (1974) Chem Inf 5(26):950–953
Mathew T, Vijayaraj M, Pal S, Tope BB, Hegde SG, Rao BS, Gopinath CS (2004) J Catal 227(1):175–185
Sato S, Koizumi M, Nozaki F (1998) J Catal 178(1):264–274
Sreekumar K, Sugunan S (2002) Appl Catal A 230(1–2):245–251
Gandhe AR, Fernandes JB, Varma S, Gupta NM (2005) J Mol Catal A 238(1–2):63–71
Gandhe AR, Fernandes JB (2004) Catal Commun 5(2):89–94
Ballarini N, Cavani F, Guidetti S, Maselli L, Rovinetti S (2008) Stud Surf Sci Catal 174 (Part B):1243–1246.
Ballarini N, Cavani F, Maselli L, Passeri S, Rovinetti S (2008) J Catal 256(2):215–225
Ballarini N, Cavani F, Passeri S, Pesaresi L, Lee AF, Wilson K (2009) Appl Catal A 366(1):184–192
Crocella V, Cerrato G, Magnacca G, Morterra C, Cavani F, Maselli L, Passeri S (2010) Dalton Trans 39(36):8527–8537
Tabanelli T, Passeri S, Guidetti S, Cavani F, Lucarelli C, Cargnoni F, Mella M (2019) J Catal 370:447–460
Guo F, Fang Z, Xu CC, Smith RL Jr (2012) Prog Energy Combust Sci 38(5):672–690
Cundy CS, Cox PA (2003) Chem Rev 34(3):663–701
Beck JS, Vartuli JC, Roth WJ, Leonowicz ME, Kresge CT, Schmitt KD, Chu CTW, Olson DH, Sheppard EW, McCullen SB, Higgins JB, Schlenker JL (1992) J Am Chem Soc 114(27):10834–10843
Barman S, Pradhan NC, Basu JK (2006) Catal Lett 111(1):67–73
Lee SC, Lee SW, Kim KS, Lee TJ, Kim DH, Kim JC (1998) Catal Today 44(1–4):253–258
Namba S, Yashima T, Itaba Y, Hara N (1980) Stud Surf Sci Catal 5:105–111
Garcia L, Giannetto G, Goldwasser MR, Guisnet M, Magnoux P (1996) Catal Lett 37(1/2):121–123
Gonzalez Pena LF, Sad ME, Padro CL, Apesteguia CR (2011) Catal Lett 141(7):939–947
Reddy KR, Ramesh K, Seela KK, Rao VV, Chary KVR (2003) Catal Commun 4(3):112–117
Chang NS, Chen CC, Chu SJ, Chen PY, Chuang TK (1989) Stud Surf Sci Catal 46:223–230
Bhattacharyya KG, Talukdar AK, Das P, Sivasanker S (2003) J Mol Catal A 197(1–2):255–262
Ji WP, Sun JK, Seo M, Sang YK, Sugi Y, Seo G (2008) Appl Catal A 349:76–85
Mores D, Kornatowski J, Olsbye U, Weckhuysen BM (2015) Chem 17:2874–2884
Balsama S, Beltrame P, Beltrame PL, Carniti P, Forni L, Zuretti G (1984) Appl Catal 13(1):161–170
Moon G, Moller KP, Bohringer W, O’Connor CT (2002) Stud Surf Sci Catal 142:635–642
Moon G, Bohringer W, O’Connor CT (2004) Catal Today 97(4):291–295
Marczewski M, Perot G, Guisnet M (1988) Stud Surf Sci Catal 41:273–282
Bregolato M, Bolis V, Busco C, Ugliengo P, Bordiga S, Cavani F, Ballarini N, Maselli L, Passeri S, Rossetti I, Forni L (2007) J Catal 245(2):285–300
Xu J, Yan AZ, Xu QH (1997) React Kinet Catal Lett 62(1):71–74
Sad ME, Padro CL, Apesteguia CR (2010) J Mol Catal A 327(1–2):63–72
Vishwanathan V, Jun KW, Kim JW, Roh HS (2004) Appl Catal A 276(1–2):251–255
Sad ME, Padro CL, Apesteguia CR (2014) Appl Catal A- 475:305–313
Vedrine JC (2019) Chin J Catal 40(1):1627–1636
Dang S, Yang H, Gao P, Wang H, Li X, Wei W, Sun Y (2019) Catal Today 330:61–75
Rui N, Zhang F, Sun K, Liu Z, Liu CJ (2020) ACS Catal 10(19):11307–11317
Védrine JC (2018) Chemsuschem 12(3):577–588
Tanabe K, Tamaru K, Kondo T, Hattori H, Sumiyoshi T (1978) J Catal 53(1):1–8
Sato S, Koizumi K, Nozaki F (1995) Appl Catal A 133(1):L7–L10
Li KT, Wang I, Chang KR (1993) Ind Eng Chem Res 32(6):1007–1011
Reddy AS, Gopinath CS, Chilukuri S (2006) J Catal 243(2):278–291
Grabowska H, Jablonski J, Mista W, Wrzyszcz J (1996) Res Chem Intermed 22(1):53–60
Rao VV, Chary KVR, Durgakumari V, Narayanan S (1990) Appl Catal 61(1):89–97
Gandhe AR, Naik SP, Kakodkar SB, Fernandes JB (2006) Catal Commun 7(5):285–288
Dang D, Wang Z, Lin W, Song W (2016) Chin J Catal 37(5):720–726
Choi WC, Kim JS, Lee TH, Woo SI (2000) Catal Today 63(2–4):229–236
Chary KVR, Ramesh K, Vidyasagar G, Rao VV (2003) J Mol Catal A-Chem 198(1–2):195–204
Gorczyca A, Moizan V, Chizallet C, Proux O, Del N (2014) Angew Chem 126(46):12426–12429
Ionescu NI, Chirca MS, Meroiu E, Albu B, Nicolau A, Enachescu M, Bota T, Charson MS (1987) Z Phys Chem 268(1):1201–1207
Kawamata M, Kiyoura T, Ohshima K, Kogure Y, Kudoh A, Kotani M (1980) US.
Huang H, Liu J, Liu X, Xiao J, Zhong S, She X, Fu Z, Yin D (2016) Fuel 182:373–381
Malshe KM, Patil PT, Umbarkar SB, Dongare MK (2004) J Mol Catal A 212(1–2):337–344
Braganza CF, Salker AV (2016) Chin J Catal 37(11):1991–1996
Grabowska H, Teterycz H, Klimkiewicz R (2005) Res Chem Intermed 31(9):797–806
Lysik P, Gorska A, Szarlik S (2014) Ind Eng Chem Res 53:17558–17562
Tabanelli T, Cocchi S, Gumina B, Izzo L, Mella M, Passeri S, Cavani F, Lucarelli C, Schutz J, Bonrath W, Netscher T (2018) Appl Catal A 552:86–97
Strassberger Z, Tanase S, Rothenberg G (2011) Eur J Org Chem 27:5246–5249
Bhadra KH, Yadav GD (2018) Appl Catal A 562:67–78
Kocevski V, Pilania G, Uberuaga BP (2020) J Mater Chem A 8:25756–25767
Sreekumar K, Sugunan S (2002) J Mol Catal A 185(1–2):259–268
Mathew T, Tope BB, Shiju NR, Hegde SG, Rao BS, Gopinath CS (2002) Phys Chem Chem Phys
Mathew T, Shiju NR, Sreekumar K, Rao BS, Gopinath CS (2002) J Catal 210(2):405–417
Mathew T, Shylesh S, Devassy BM, Vijayaraj M, Satyanarayana CV, Rao BS, Gopinath CS (2004) Appl Catal A 273(1–2):35–45
Wang YL, Zhou Z, Jia MJ, Zhu XN, Zhang WX, Jiang DZ (2005) Catal Lett 104(1–2):67–71
Wang Y, Yang P, Liu G, Xu L, Jia M, Zhang W, Jiang D (2008) Catal Commun 9(10):2044–2047
Klimkiewicz R, Grabowska H, Mista W, Przybylski K (2012) Ind Eng Chem Res 51(5):2205–2213
Fumio N, Isao K (1977) Bull Chem Soc Jpn 8(24):614–619
Pierantozzi R, Nordquist AF (1986) Appl Catal 21(2):263–271
Samolada MC, Grigoriadou E, Kiparissides Z, Vasalos IA (1995) J Catal 152(1):52–62
Velu S, Swamy CS (1994) Appl Catal A 119(2):241–252
Velu S, Swamy CS (1996) Appl Catal A 145(2):225–230
Velu S, Swamy CS (1997) React Kinet Catal Lett 62(2):339–346
Dai W, Wang C, Dyballa M, Wu G, Guan N, Li L, Xie Z, Hunger M (2015) ACS Catal 5:317–326
Grabowska H, Klimkiewicz R, Tylus W, Godowski PJ (2003) Appl Catal A 240(1–2):111–117
Tleimatmanzalji R, Bianchi D, Pajonk GM (1993) Appl Catal A 101(2):339–350
Funding
Funding was provided by National Natural Science Foundation of China (Grant Number 91534115).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Huang, F., Li, L., Guan, M. et al. A Review of the Process on Vapor Phase Methylation of Phenol with Methanol. Catal Lett 153, 754–769 (2023). https://doi.org/10.1007/s10562-022-04011-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-022-04011-5