Synthesis of Oleic Acid Derivatives as Pour Point Depressant (PPD)

Nila Tanyela Berghuis; Zayed Abdulmalik Marwan; Agus Astra Pramana; Jati Arie Wibowo

doi:10.14710/jksa.28.1.23-30

DOI: https://doi.org/10.14710/jksa.28.1.23-30

Synthesis of Oleic Acid Derivatives as Pour Point Depressant (PPD)

Nila Tanyela Berghuis^{1, 2}

, Zayed Abdulmalik Marwan¹, Agus Astra Pramana³

, Jati Arie Wibowo³

¹Department of Chemistry, Faculty of Sciences and Computer Science, Universitas Pertamina, Jakarta, Indonesia

²Downstream, Center of Excellence (COE), Universitas Pertamina, Jakarta, Indonesia

³Petroleum Engineering, Faculty of Exploration and Industrial Technology, Universitas Pertamina, Jakarta, Indonesia

Received: 10 Oct 2024; Revised: 15 Jan 2025; Accepted: 16 Jan 2025; Published: 31 Jan 2025.

BibTex Citation Data :

@article{JKSA67379,
    author = {Nila Berghuis and Zayed Abdulmalik Marwan and Agus Astra Pramana and Jati Arie Wibowo},
    title = {Synthesis of Oleic Acid Derivatives as Pour Point Depressant (PPD)},
    journal = {Jurnal Kimia Sains dan Aplikasi},
  volume = {28},
    number = {1},
    year = {2025},
    keywords = {Pour Point Depressant; Oleic Acid; Derivative reactions; Crude Oil; Pour Point},
    abstract = { Crude oil is widely used worldwide as an energy source in various fields. Over the years, crude oil production has decreased due to one major problem that continues to occur, namely wax deposition. Wax deposits tend to occur due to the composition of the crude oil itself. Crude oil mostly consists of large amounts of hydrocarbon compounds, such as paraffins. Therefore, an additive, such as a pour point depressant (PPD), is needed to inhibit or prevent wax formation. This study compares the performance of various PPDs synthesized using oleic acid as a base material. The esterification of oleic acid with alcohols yielded PPD-Ester Butanol (96.72%) and PPD-Ester Decanol (72.21%). Further esterification with oleic acid resulted in PPD-Ester Butanol + Oleic Acid (47.30%) and PPD-Ester Decanol + Oleic Acid (22.56%). These derivatives can undergo additional reactions, such as epoxidation, diol formation, and esterification, to produce a PPD. Pour point measurements on crude oil samples were conducted following ASTM D-5853. The blank sample had a pour point of 39°C. PPD-Ester Decanol reduced the pour point by 3°C, while all PPD-Esters further esterified with oleic acid lowered it by 9°C. Chemical characterization via FTIR analysis confirmed the presence of C=C, C=O, and aliphatic C-H functional groups. GC-MS analysis of PPD-Ester Decanol + Oleic Acid (decyl 9-monooleate, 10-hydroxy oleate) identified three major compounds: 1-decanol, oleic acid, and decyl oleate. Physical characterization revealed that the synthesized PPDs had densities ranging from 850 to 1,066 kg/m 3 . },
   issn = {2597-9914},   pages = {23--30}  doi = {10.14710/jksa.28.1.23-30},
    url = {https://ejournal.undip.ac.id/index.php/ksa/article/view/67379}
}

Citation Format:

Abstract

Crude oil is widely used worldwide as an energy source in various fields. Over the years, crude oil production has decreased due to one major problem that continues to occur, namely wax deposition. Wax deposits tend to occur due to the composition of the crude oil itself. Crude oil mostly consists of large amounts of hydrocarbon compounds, such as paraffins. Therefore, an additive, such as a pour point depressant (PPD), is needed to inhibit or prevent wax formation. This study compares the performance of various PPDs synthesized using oleic acid as a base material. The esterification of oleic acid with alcohols yielded PPD-Ester Butanol (96.72%) and PPD-Ester Decanol (72.21%). Further esterification with oleic acid resulted in PPD-Ester Butanol + Oleic Acid (47.30%) and PPD-Ester Decanol + Oleic Acid (22.56%). These derivatives can undergo additional reactions, such as epoxidation, diol formation, and esterification, to produce a PPD. Pour point measurements on crude oil samples were conducted following ASTM D-5853. The blank sample had a pour point of 39°C. PPD-Ester Decanol reduced the pour point by 3°C, while all PPD-Esters further esterified with oleic acid lowered it by 9°C. Chemical characterization via FTIR analysis confirmed the presence of C=C, C=O, and aliphatic C-H functional groups. GC-MS analysis of PPD-Ester Decanol + Oleic Acid (decyl 9-monooleate, 10-hydroxy oleate) identified three major compounds: 1-decanol, oleic acid, and decyl oleate. Physical characterization revealed that the synthesized PPDs had densities ranging from 850 to 1,066 kg/m³.

Fulltext View|Download Email colleagues

Keywords: Pour Point Depressant; Oleic Acid; Derivative reactions; Crude Oil; Pour Point

Funding: Universitas Pertamina

Article Metrics:

Article Info

Section: Research Articles

Language : EN

In Vol 28, No 1 (2025): Volume 28 Issue 1 Year 2025

Most cited articles

Pengaruh Waktu pada Pembentukan Kalsium Fosfat dengan Sistem Membran Selulosa Bakterial Pemanfaatan Montmorillonit Terpilar Al-Cr pada Adsorpsi Zat Warna Rhodamin B dengan Variasi Massa Adsorben dan Waktu Adsorpsi Penentuan Total Kadar Fenol dari Daun Kersen Segar, Kering dan Rontok (Muntingia calabura L.) serta Uji Aktivitas Antioksidan dengan Metode DPPH Profil Kandungan Protein dan Tekstur Tahu Akibat Penambahan Fitat pada Proses Pembuatan Tahu Activity of Actinomycetes Isolated from Mangrove Segara Anakan Cilacap toward Methicillin-resistant Staphylococcus aureus (MRSA) More cited articles

Anas Azeem, Rahul Kumar, Biswadeep Pal, Tarun Kumar Naiya, Use of novel pour point depressant synthesized from vegetable oil for waxy crude oil, Petroleum Science and Technology, 38, 3, (2020), 185-193 https://doi.org/10.1080/10916466.2019.1697291
Lize M. S. L. Oliveira, Rita C. P. Nunes, Ygor L. L. Ribeiro, Dayane M. Coutinho, Débora A. Azevedo, Júlio C. M. Dias, Elizabete F. Lucas, Wax Behavior in Crude Oils by Pour Point Analyses, Journal of the Brazilian Chemical Society, 29, 10, (2018), 2158–2168 https://doi.org/10.21577/0103-5053.20180092
Yulia M. Ganeeva, Tatiana N. Yusupova, Gennady V. Romanov, Waxes in asphaltenes of crude oils and wax deposits, Petroleum Science, 13, 4, (2016), 737-745 https://doi.org/10.1007/s12182-016-0111-8
Fei Yang, Chen Li, Chuanxian Li, Dan Wang, Scaling of Structural Characteristics of Gelled Model Waxy Oils, Energy & Fuels, 27, 7, (2013), 3718-3724 https://doi.org/10.1021/ef400554v
Nurul Komariyah, Perbandingan Hasil Pengujian Pour Point pada Crude Oil Menggunakan Metode Uji ASTM D 97 dan ASTM D 5853, Swara Patra : Majalah Ilmiah PPSDM Migas, 12, 1, (2022), 11-16 https://doi.org/10.37525/sp/2022-1/315
Alnaimat Fadi, Ziauddin Mohammed, Mathew Bobby, Wax Deposition in Crude Oil Transport Lines and Wax Estimation Methods, in: Y. Yang (Ed.) Intelligent System and Computing, IntechOpen, Rijeka, 2019, https://doi.org/10.5772/intechopen.89459
Mingan Zhou, Yi He, Yanwei Chen, Yingpin Yang, Hualin Lin, Sheng Han, Synthesis and Evaluation of Terpolymers Consist of Methacrylates with Maleic Anhydride and Methacrylic Morpholine and Their Amine Compound as Pour Point Depressants in Diesel Fuels, Energy & Fuels, 29, 9, (2015), 5618-5624 https://doi.org/10.1021/acs.energyfuels.5b01072
Bengt Kronberg, Krister Holmberg, Bjorn Lindman, Surface chemistry of surfactants and polymers, John Wiley & Sons, 2014, ^ https://doi.org/10.1002/9781118695968
Lim Zhen Hao, Hikmat Said Al-Salim, Norida Ridzuan, A Review of the Mechanism and Role of Wax Inhibitors in the Wax Deposition and Precipitation, Pertanika Journal of Science and Technology, 27, 1, (2019), 499-526
Astra Agus Pramana D. N., Teddy Anda Pagpa, Analisis Keefektifan Pour Point Depressant pada Waxy Crude Oil pada Lapangan TAP, Lembaran Publikasi Minyak dan Gas Bumi, 57, 1, (2023), 41-48 https://doi.org/10.29017/LPMGB.57.1.1312
Cheah Han Sern, Choo Yuen May, Zuriati Zakaria, Rusli Daik, Synthesis of palmitic acid-based esters and their effect on the pour point of palm oil methyl esters, Journal of Oil Palm Research, 20, (2008), 542-547
Thevaruban Ragunathan, Hazlina Husin, Colin D. Wood, Wax Formation Mechanisms, Wax Chemical Inhibitors and Factors Affecting Chemical Inhibition, Applied Sciences, 10, 2, (2020), 479 https://doi.org/10.3390/app10020479
Suryanarayan Cherukuvada, Ramanpreet Kaur, Tayur N. Guru Row, Co-crystallization and small molecule crystal form diversity: from pharmaceutical to materials applications, CrystEngComm, 18, 44, (2016), 8528-8555 https://doi.org/10.1039/C6CE01835A
Arun Borthakur, Narayan C. Laskar, Ranjit K. Mazumdar, Kosuru V. Rao, Bulusu Subrahmanyam, Synthesis and evaluation of alkyl fumarate–vinyl acetate copolymers in combination with alkyl acrylates as flow improvers for Borholla crude oil, Journal of Chemical Technology & Biotechnology, 62, 1, (1995), 75-80 https://doi.org/10.1002/jctb.280620112
Yuandao Chi, Nagu Daraboina, Cem Sarica, Effect of the Flow Field on the Wax Deposition and Performance of Wax Inhibitors: Cold Finger and Flow Loop Testing, Energy & Fuels, 31, 5, (2017), 4915-4924 https://doi.org/10.1021/acs.energyfuels.7b00253
O. A. A. El-Shamy, T. T. Khidr, M. M. Doheim, Polymeric Nonionic Surfactants as a Pour Point Depressant, Petroleum Science and Technology, 32, 18, (2014), 2195-2202 https://doi.org/10.1080/10916466.2013.774015
T. T. Khidr, M. M. Doheim, O. A. A. El-Shamy, Pour Point Depressant of Fuel Oil Using Non-ionic Surfactants, Petroleum Science and Technology, 33, 17-18, (2015), 1619-1626 https://doi.org/10.1080/10916466.2015.1081942
Fatimah Zahara Abdullah, Azman Ma’amor, Nur Atiqah Daud, Sharifah Bee Abd Hamid, Selective Synthesis of PEG-Monoester Using Cesium Heteropoly Acid as Heterogeneous Catalyst, Química Nova, 40, 5, (2017), 506-512 http://dx.doi.org/10.21577/0100-4042.20170040
Maisaroh Maisaroh, Handayani Wiwik, Optimasi Proses Epoksidasi Asam Oleat pada Scaling Up Sintesis Asam 9,10-Dihidroksi Stearat (DHSA) Bench Scale, Majalah Ilmiah Pengkajian Industri; Journal of Industrial Research and Innovation, 12, 1, (2023), 39-46 https://doi.org/10.29122/mipi.v12i1.2616

Last update:

No citation recorded.

Last update: 2026-09-02 01:47:08

No citation recorded.

As an article writer, the author has the right to use their article for various purposes, including use by institutions that employ the author or institutions that provide funding for the research. These author rights are granted without special permission.

Authors who publish a paper in JKSA have broad rights to use their work for teaching and scientific purposes without the need to request permission, including: (i) teaching in the author's class or institution; (ii) presenting the work at meetings or conferences and distributing copies to participants; (iii) using the work in training conducted by the author or the author's institution; (iv) distributing copies to colleagues for research purposes; (v) using the work in the compilation of subsequent works by the author; (vi) including the work in a thesis or dissertation; (vii) reusing part of the article in another work, with appropriate citation; (viii) preparing derivative works, with appropriate citation; and (ix) voluntarily posting the work on open websites operated by the author or the author's institution for scientific purposes, in accordance with the CC BY-SA License.

Authors and readers may copy and redistribute the material in any medium or format, and may remix, transform, and build upon the material for any purpose, provided that they give appropriate credit by citing the article or its content, provide a link to the license, and indicate if changes were made.

The authors submitting a manuscript do so on the understanding that, if accepted for publication, the copyright of the article shall be assigned to Jurnal Kimia Sains dan Aplikasi (JKSA). Copyright encompasses the rights to reproduce and distribute the article in all forms and media, including reprints, photographs, microfilms, and any other similar reproductions, as well as translations.

Reproducing any part of this journal, storing it in a database, or transmitting it in any form or medium is permitted without written permission from JKSA. However, the original source must be properly cited in accordance with academic conventions.

JKSA, the Chemistry Department of Diponegoro University, and the Editor make every effort to ensure that no inaccurate, false, or misleading data, opinions, or statements are published in JKSA. However, the content of each article is the sole and exclusive responsibility of its authors.

The Copyright Transfer Form can be downloaded here: [Copyright Transfer Form - Indonesian] [Copyright Transfer Form - English]. The copyright form should bear the authors' original signatures and be sent to the Editor as a printed document, a scanned document sent via email, or by fax.

Prof. Adi Darmawan, Ph.D (Editor in Chief)

Editor in chief of Jurnal Kimia Sains dan Aplikasi (JKSA)

Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University

Jl. Prof. Soedarto, Kampus Undip Tembalang, Semarang, Central Java, Indonesia 50275
Email: jksa@live.undip.ac.id