Effect of Temperature, Time and Diimide/Rubber Ratio on the Hydrogenation of Liquid Natural Rubber by Response Surface Methodology

https://doi.org/10.22146/ijc.36706

Mohamad Shahrul Fizree Idris(1), Nur Hanis Adila Azhar(2), Fazira Firdaus(3), Siti Efliza Ashari(4), Siti Fairus Mohd Yusoff(5*)

(1) School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
(2) School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
(3) School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
(4) Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Jalan UPM, 43400 Serdang, Selangor, Malaysia
(5) School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia Polymer Research Center (PORCE), Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
(*) Corresponding Author

Abstract


Hydrogenated liquid natural rubber (HLNR) was synthesized from liquid natural rubber (LNR) by thermolysis of p-toluenesulfonyl hydrazide (TSH). The HLNR structure was characterized by Fourier-transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopies. Thermogravimetric analysis (TGA) showed that the HLNR had higher decomposition temperature compared to LNR. A response surface methodology (RSM) based on a central composite rotatable design (CCRD) with five-level-three-factors was used to optimize the main important reaction parameters, such as the TSH:LNR weight ratio (1–3), reaction temperature (110–150 °C), and reaction time (1–8 h). A quadratic model was developed using this multivariate statistical analysis. Optimum conditions for the non-catalytic hydrogenation of LNR using TSH were obtained; an LNR hydrogenation percentage of 83.47% at a TSH:LNR weight ratio of 1.41, a reaction temperature of 118.11 °C, and a reaction time of 3.84 h were predicted. The R2 value of 0.9949 indicates that the model provides data that are well matched with those from the experiment.

Keywords


response surface methodology; central composite rotatable design; optimization; liquid natural rubber; hydrogenation

Full Text:

Full Text PDF


References

[1]      Bode, H.B., Kerkhoff, K., and Jendrossek, D., 2001, Bacterial degradation of natural and synthetic rubber, Biomacromolecules, 2 (1), 295–303.

[2] Tanaka, Y., and Sakdapipanich, J.T., 2005, “Chemical Structure and Occurrence of Natural Polyisoprenes” in Biopolymers Online, Steinbüchel, A., (Ed.), Wiley‐VCH Verlag GmbH & Co. KGaA.

[3] Rose, K., and Steinbüchel, A., 2005, Biodegradation of natural rubber and related compounds: Recent insights into a hardly understood catabolic capability of microorganisms, Appl. Environ. Microbiol., 71 (6), 2803–2812.

[4] Azhar, N.H.A., Jamaluddin, N., Md Rasid, H., Yusof, M.J.M., and Yusoff, S.F.M., 2015, Studies on hydrogenation of liquid natural rubber using diimide, Int. J. Polym. Sci., 2015, 243038.

[5] Institut de Recherches sur le Caouthchouc (IRCA), 1985, Development of liquid rubber, Final report, UNIDO, UF/GLO/81/059.

[6] Nor, H.M., and Ebdon, J.R., 1998, Telechelic liquid natural rubber: A review, Prog. Polym. Sci., 23 (2), 143–177.

[7] Tanaka, Y., Sakaki, T., Kawasaki, A., Hayashi, M., Kanamaru, E., and Shibata, K., 1999, Production process of depolymerized natural rubber, US Patents, US5856600 A.

[8] Burfield, D., and Gan, S.N., 1977, Determination of epoxy groups in natural rubber by degradation methods, Polymer, 18 (6), 607–611.

[9] Gillier‐Ritoit, S., Reyx, D., Campistron, I., Laguerre, A., and Singh, R.P., 2003, Telechelic cis‐1,4‐oligoisoprenes through the selective oxidolysis of epoxidized monomer units and polyisoprenic monomer units in cis‐1,4‐polyisoprenes, J. Appl. Polym. Sci., 87 (1), 42–46.

[10] Thanki, P.N., Reyx, D., Campistron, I., Laguerre, A., and Singh, R.P., 2004, Metathetic alkenolysis of unsaturated units in polymers and copolymers-application to the synthesis of epoxy-functionalized oligomers and organic compounds, Eur. Polym. J., 40 (11), 2611–2616.

[11] Rao, P.V.C., Upadhyay, V.K., and Pillai, S.M., 2001, Hydrogenation of polybutadienes catalyzed by RuCl2(PPh3)3 and a structural study, Eur. Polym. J., 37 (6), 1159–1164.

[12] Singha, N.K., De, P.P., and Sivaram, S., 1997, Homogeneous catalytic hydrogenation of natural rubber using RhCl(PPh3)3, J. Appl. Polym. Sci., 66 (9), 1647–1652.

[13] Gan, S.N., Subramaniam, N., and Yahya, R., 1996, Hydrogenation of natural rubber using nickel 2-ethylhexanoate catalyst in combination with triisobutylaluminum, J. Appl. Polym. Sci., 59 (1), 63–70.

[14] Harwood, H.J., Russell, D.B., Verthe, J.J., and Zymonas, J., 1973, Diimide as a reagent for the hydrogenation of unsaturated polymers, Macromol. Chem. Phys., 163 (1), 1–12.

[15] Mango, L.A., and Lenz, R.W., 1973, Hydrogenation of unsaturated polymers with diimide, Macromol. Chem. Phys., 163 (1), 13–36.

[16] Mahittikul, A., Prasassarakich, P., and Rempel, G.L., 2007, Noncatalytic hydrogenation of natural rubber latex, J. Appl. Polym. Sci., 103 (5), 2885–2895.

[17] Jamaluddin, N., Yusof, M.J.M., Abdullah, I., and Yusoff, S.F.M., 2016, Synthesis, characterization, and properties of hydrogenated liquid natural rubber, Rubber Chem. Technol., 89 (2), 227–239.

[18] Lundstedt, T., Seifert, E., Abramo, L., Thelin, B., Nyström, Å., Pettersen, J., and Bergman, R., 1998, Experimental design and optimization, Chemom. Intell. Lab. Syst., 42 (1), 3–40.

[19] Li, B., Wang, W., Wang, K., Zhang, D., Guan, L., and Liu, F., 2015, Thiacloprid suspension formula optimization by a response surface methodology, RSC Adv., 5 (34), 26654–26661.

[20] Gunawan, E.R., Basri, M., Rahman, M.B.A., Salleh, A.B., and Rahman, R.N.Z.A., 2005, Study on response surface methodology (RSM) of lipase-catalyzed synthesis of palm-based wax ester, Enzyme Microb. Technol., 37 (7), 739–744.

[21] Gunawan, E.R., and Suhendra, D., 2010, Four-factor response surface optimization of the enzymatic synthesis of wax ester from palm kernel oil, Indones. J. Chem., 8 (1), 83–90.

[22] Abdullah, I., 1996, Process for manufacturing liquid natural rubber (LNR), Malaysian Patent, MY-108852-A.

[23] Kargarzadeh, H., Ahmad, I., Abdullah, I., Thomas, R., Dufresne, A., Thomas, S., and Hassan, A., 2015, Functionalized liquid natural rubber and liquid epoxidized natural rubber: A promising green toughening agent for polyester, J. Appl. Polym. Sci., 132 (3), 41292 (1–15).

[24] Li, Y., Lu, J., Gu, G., and Mao, Z., 2005, Characterization of the enzymatic degradation of arabinoxylans in grist containing wheat malt using response surface methodology, J. Am. Soc. Brew. Chem., 63 (4), 171–176.

[25] Hamzaoui, A.H., Jamoussi, B., and M'nif, A., 2008, Lithium recovery from highly concentrated solutions: Response surface methodology (RSM) process parameters optimization, Hydrometallurgy, 90 (1), 1–7.

[26] Bezerra, M.A., Santelli, R.E., Oliveira, E.P., Villar, L.S. and Escaleira, L.A., 2008, Response surface methodology (RSM) as a tool for optimization in analytical chemistry, Talanta, 76 (5), 965–977.



DOI: https://doi.org/10.22146/ijc.36706

Article Metrics

Abstract views : 645 | views : 553


Copyright (c) 2018 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemisty (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.