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Journal : Indonesian Journal of Chemistry

Synthesis of 1,4-Dioxaspiro[4.4] and 1,4-Dioxaspiro[4.5] Novel Compounds from Oleic Acid as Potential Biolubricant Kurniawan, Yehezkiel Steven; Ramanda, Yudha; Thomas, Kevin; Hendra, Hendra; Wahyuningsih, Tutik Dwi
Indonesian Journal of Chemistry Vol 17, No 2 (2017)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (381.558 KB) | DOI: 10.22146/ijc.24891

Abstract

Two 1,4-dioxaspiro novel compounds which derivated from methyl 9,10-dihydroxyoctadecanoate (MDHO) with cyclopentanone and cyclohexanone had been synthesized by a sonochemical method in the presence of montmorillonite KSF catalyst. The MDHO compound had been prepared from 9,10-dihydroxyoctadecanoic acid (DHOA) and methanol. Meanwhile, DHOA was synthesized by hydroxylation of oleic acid with the solution of 1% KMnO4 under basic condition. The structures of the products were confirmed by FTIR, GC-MS, 1H-NMR, and 13C-NMR spectrometers. Hydroxylation reaction of oleic acid gave DHOA as a white solid powder in 46.52% yield (m.p. 131-132 °C). On the other side, esterification reaction via sonochemical method between DHOA and methanol gave MDHO as a white powder in 93.80% yield (m.p. 80-81 °C). The use of cyclopentanone in 45 min sonochemical method gave methyl 8-(3-octyl-1,4-dioxaspiro[4.4]nonan-2-yl)octanoate as a yellow viscous liquid in 50.51% yield. The other compound, methyl 8-(3-octyl-1,4-dioxaspiro[4.5]decan-2-yl)octanoate as yellow viscous liquid had been synthesized by similar method with cyclohexanone via the sonochemical method in 45.12% yield. From physicochemical properties, i.e. density, total acid number, total base number, and iodine value, gave the conclusion that these novel compounds are potential biolubricant candidates to be developed.
Co-Authors Abdul Rahmat, Abdul Abdul Razak Achmad Yasir Baeda, Achmad Yasir Adithya Yudistira Aditya Rochman, Aditya Afif, Muhammad Ibnu Afrizal Afrizal Agus Supriyanto Alipudin, Alipudin Amah Majidah Amin, Amirudin M Amrizal Amrizal Anas, Irwan Andino Maseleno Anizar Indriani Apriadi, Muhammad ARDYANSAH, ADY Argubi, Adi Hidayat Ari Lukas Runtunuwu, Ari Lukas Arif Wibowo arnomo, sasa ani Asfriyati, Asfriyati Azis, Mochammad Abdul Baiduri Baiduri Baihaqy Yussof, Mohd Hilmy Batubara, Fanny Yuliana Budi, Nawanto Budijanto Budijanto, Budijanto C Cari, C Candra, Suryadi Ce, Win Chandra Irsan Chandra Satrya Citra Dewi Darius H Ananda Darmiah Darmiah Diaraya Diaraya, Diaraya Djinis, Musdar Effy Dwi P.Priadi, Dwi Edy Lazuardi, Edy Eri Barlian, Eri Erlina Erlina Erminawati erminawati Fahmi, Khandra Fajri, M Fauzi, Rahman Fawwaz, Insidini Feidihal Feidihal Fetricia, Rika Firdaus Hamta, Firdaus Fredicia Fredicia Gembong Edhi Setyawan Gilang Ramadhan Gusti Budjang Hadi Sutopo Hadi, Syukri Hadipranoto, Ichsan Hadipranoto, Ichsan Ham, Hanry Hardani Hardani, Hardani Harijanto Pangestu, Harijanto Hary Sanjaya Haryani, Sesmeri Hasmin Tamsah, Hasmin Hastina, Nina Herdian, Fithra Hernadewita Hernadewita I Nyoman Ruja, I Nyoman Imam Santoso Imanila, Imanila Indra Laksmana Indri Hapsari Susilowati Irzal, Irzal Isahak, Marzuki Jamaluddin Jamaluddin Jamili Jamili Jayanti, Mei Indra Jeanny Pragantha Jimmy Jimmy Johan Johan Julianto, Rifki Junaidi Indrawadi Kanda Ruskandi, Kanda Kholil, A. Yusuf Kholil, Ahmad Yusuf Kristiana kristiana Kristyadi, Tarsisius Kurniawan, Johanus Kurniawan, Yehezkiel Steven La Surimi, La M Suparlan Maimunah Maimunah Manoppo, Jeanette Irene Chistie Mardiah Mardiah Maria Montessori Mas Mera, Mas Mas'ud, Mas'ud Mudiyati Rahmatunnisa Muh. Iman Darmawan, Muh. Iman Muhammad Adam, Muhammad Muhammad Anshar Muhammad Makky Muhsin Muhsin Muliyati, Rita Mulyani, Astriana Nanik Riandita Sari Nasrullah Nasrullah Nelvia Nelvia Nina Sevani Nirwana, Eva Njo Anastasia Novianto, Chiko Nurhaeni Nurhaeni Nurmaini Nurmaini Nurtam, Mohamad Riza Nurvelly Rosanti, Nurvelly Padli, Feri Perdana Putera, Perdana Puspa Arum, Enggar Diah Puspawan, Angky Putri, Ronasari Mahaji Rahmad Ade Putra, Rahmad Ade Rahman Rahman Ramanda, Yudha Ranelis Ranelis Ratnia Solihah, Ratnia Retnani Latifah, Retnani Reynaldo Reynaldo, Reynaldo Ridwan Zahdi Syaaf Riko Riko Rowena, Janny Rowena, Janny Rudy Dwi Nyoto, Rudy Dwi Rully Mujiastuti Rusdi Rusdi Ruslan Ruslan Rustan Efendi Rustiyarso, Rustiyarso Rusydi H., M. Samuddin, Sakka Saputri, Sisca Wulansari Sardino, Sardino Sarif, Rafi Satiawan, Budi Sautma Ronni Basana Sekar Tina Selvi Selvi Shantika, Tito Siti Witianti Son Suwasono, Son Sri Aulia Novita Sri Ratmini, Niluh Putu Suhardjono Suhardjono Suhartini, Yenni Sumantri, Surya Suparto Darudiato, Suparto Supriyadi Supriyadi Suryanti Suryanti Sutarmadi Sutarmadi Swito Prastiwi, Swito Syelly, Rosda Syerly Klara Tajung, Ariani Taurusyanti, Dewi Thomas Stefanus Kaihatu Thomas, Kevin Trisnawati, Desi Tursina Tursina Tutik Dwi Wahyuningsih Umar Umar Vinola Herawaty Wardati, Wardati Wasino Wasino Wesley, Julian Widjaja, Antonius Andri Widodo S. Pranowo Wijaya Kurniawan Winaldi, Dio Wirawan, Erick Womsiwor, Olla Ona Oktarian Y Witanto, Y Yovan Witanto Yudistira Yudistira Yunika, Febri Yulsa Yusuf, Andreas Zikri, Afdal