Synthesis of Patchouli Esters from Patchouli Oil in the Presence of Homogeneous and Heterogeneous Catalyst

Abstract:

Patchouli alcohol was isolated from patchouli oil by fractional distillation under reduced pressure. Patchouli esters were then prepared from isolated patchouli alcohol via esterification reaction in the presence of homogeneous (concentrated hydrochloric acid) and heterogeneous (acid-activated bentonite) catalysts. Fractional distillation under reduced pressure was carried out by heating patchouli oil under a pressure until 0 mmHg. Esterification reaction was carried out by heating patchouli alcohol with propionic acid in the presence of an acid catalyst at 100-110 for 3 h The products were characterized using FTIR and GCMS spectrometers. The esterification reaction with HCl 37% and bentonite catalysts produced patchouli propionate in 26% and 21% yields, respectively.

• Periodical: Materials Science Forum (Volume 1061)
• Pages: 145-150
• DOI: https://doi.org/10.4028/p-24p399
• Online since: May 2022
• Authors: Priatmoko Priatmoko*, Muhammad Idham Darussalam Mardjan, Fadlilah Fadlilah, Dian Hafiizh Rachmawati
• Keywords: Esterification, Patchouli Alcohol, Patchouli Propionate, Vacuum Distillation

References

[1] K.H.C. Başer, G. Buchbauer, Handbook of Essential Oils: Science, Technology, and Applications,1st ed., CRC Press, Boca Raton, Florida, US, (2009).

[2] TA van Beek, D. Joulain, The essential oil of patchouli, Pogostemon cablin: A review, Flavour Fragrance J. 33 (2017) 6–51.

DOI: 10.1002/ffj.3418

[3] L. Bacci, J.K.A. Lima, A.P.A. Araújo, A.F. Blank, I.M.A. Silva, A.A. Santos, A.C.C. Santos, P.B. Alves, M.C. Picanço, Toxicity, behavior impairment, and repellence of essential oils from pepper-Rosmarin and patchouli to termites, Entomol. Exp. Appl. 156 (2015) 66–76.

DOI: 10.1111/eea.12317

[4] J. Howarth, Natural product supply bulletin: Patchouli, Mexican lime and the Crimean conflict, Ingredients 40 (2015) 32–37.

[5] P.L.B. Jain, S.R. Patel, M.A. Desai, Enrichment of patchouli alcohol in patchouli oil by aiding sonication in hydrotropic extraction, Ind. Crops Prod. 158 (2020) 113011.

DOI: 10.1016/j.indcrop.2020.113011

[6] D. Ermaya, S.P. Sari, A. Patria, F. Hidayat, F. Radi, Identification of patchouli oil chemical components as the results on distillation using GC-MS, IOP Conf. Ser.: Earth Environ. Sci. 365 (2019) 012039.

DOI: 10.1088/1755-1315/365/1/012039

[7] Z.Q. Su, X.L. Wu, M.J. Bao, C.W. Li, S.Z. Kong, Z.R. Su, X.P. Lai, Y.C. Li, J.N. Chen, Isolation of (-)-patchouli alcohol from patchouli oil by fractional distillation and crystallization, Trop. J. Pharm. Res. 13 (2014) 359–363.

DOI: 10.4314/tjpr.v13i3.7

[8] R. Sirsam, D. Hansora, G.A. Usmani, A mini-review on solid acid catalysts for esterification reactions, J. Inst. Eng. (India): Ser. E 97 (2016) 167–181.

DOI: 10.1007/s40034-016-0078-4

[9] R. Retnowati, W. Warsito, B. Poerwadi, The effort to improve the economic value of patchouli oil: The controlled esterification at production of aroma compounds base on patchouli oil, Jurnal Teknik Industri 8 (2007) 67–70.

DOI: 10.22219/jtiumm.vol8.no1.67-70

[10] G.F. Swieger, Mechanical Catalyst, John Wiley & Sons, Inc., New Jersey, (2008).

[11] S. Jeenpadiphat, D.N. Tungasmita, Acid-activated pillar bentonite as novel catalyst for the esterification of high FFA oil, Powder Technol. 237 (2013) 634–640.

DOI: 10.1016/j.powtec.2013.02.001

[12] V.V. Krupskaya, S.V. Zakusin, E.A. Tyupina, O.V. Dorzhieva, M.S. Chernov, Y.V. Bychkova, Transformation of structure and adsorption properties of montmorillonite under thermochemical treatment, Geochem. Int. 57 (2019) 314–330.

DOI: 10.1134/s0016702919030066

[13] A. Abdulloh, S. Maryam, N.S. Aminah, T. Triyono, W. Trisunaryanti, M. Mudasir, D. Prasetyoko, Modification of Turen's bentonite with AlCl3 for esterification of palmitic acid, Bull. Chem. React. Eng. Catal. 9 (2014) 66–73.

DOI: 10.9767/bcrec.9.1.5513.66-73

[14] B. Caglar, B. Afsin, E. Koksal, A. Tabak, E. Eren, Characterization of Unye bentonite after treatment with sulfuric acid, Quim. Nova 36 (2013) 955–959.

DOI: 10.1590/s0100-40422013000700006

[15] S. Sundarajan, N.H. Abdurahman, Chemical compound characterizations of patchouli leaf extract via GC-MS, LC-QTOF-MS, FTIR, and 1H-NMR, Int. J. Eng. Res. Sci. Technol. 8 (2019) 1054–1059.

DOI: 10.17577/ijertv8is060541

[16] F. Firdaus, N.H. Soekamto, S. Firdausiah, H. Rasyid, A. Rifai, β-Patchoulene: Conversion from patchouli alcohol by acid catalysts and its in silico anti-inflammatory study, Nat. Prod. Sci. 27 (2021) 208–215.

[17] K. Nisyak, M.F. Rahman, S. Sutrisno, Synthesis organonitrogen compounds from patchouli alcohol through Ritter reaction with acetonitrile and its toxicity to Artemia salina Leach, J. Pure Appl. Chem. Res. 2 (2013) 11–18.

DOI: 10.21776/ub.jpacr.2013.002.01.113

[18] L.E. Kolsi, J. Yli-Kauhaluoma, V.M. Moreira, Catalytic, tunable, one-step bismuth(III) triflate reaction with alcohols: Dehydration versus dimerization, ACS Omega 3 (2018) 8836–8842.

DOI: 10.1021/acsomega.8b01401