Research and application progress of castor oil-based downstream products and its plasticizer

doi:10.16085/j.issn.1000-6613.2015.07.029

Abstract

Abstract: With the rapid consumption of fossil resources, the global energy crisis has caused serious concern. In the utilization of plant resources, the exploitation of downstream products, during which castor oil used as raw materials, has become to be a hot research area. The preparation methods, performance as well as the application fields of castor oil-based downstream products were introduced in this work. The preparation and properties of some castor oil-based downstream products, such as dehydrated castor oil, transesterification of castor oil, exploitation of castor oil, polyurethane of castor oil and so on, were reviewed. The types and application areas of castor oil-based plasticizers were sketched and the preparation methods and the properties of epoxidized methyl acetorieinoleate were analyzed. The problems of the effects of the reaction temperature and the dosage of catalyst on the stability of epoxy group in the production process of the castor oil-based plasticizer were discussed, and the developing trends in the field of castor oil-based plasticizers were proposed.

Key words: castor oil, polyurethane, plasticizers, epoxidation

摘要： 随着全球化石资源消耗量的不断剧增, 能源危机问题引起了广泛的关注。在植物资源能源化的利用中, 以蓖麻油为原料开发高附加值下游产品已成为研究热点。本文介绍了国内外蓖麻油基下游产品的制备方法、产品性能及应用领域等方面。回顾了脱水蓖麻油、酯交换蓖麻油、环氧化蓖麻油、蓖麻油基聚氨酯等下游产物的制备与应用性能研究。简述了蓖麻油基增塑剂的种类及应用领域, 具体分析了环氧乙酰蓖麻油酸甲酯的制备方法及产品特性。提出了在我国蓖麻油基增塑剂的生产过程中反应温度、催化剂用量等因素影响环氧基团稳定性的问题, 指出目前我国催化合成蓖麻油基增塑剂的趋势和发展方向。

关键词: 蓖麻油, 聚氨酯, 增塑剂, 环氧化

CLC Number:

TQ414.5

XU Wei, GE Xiaodong, JIN Lizhu, SHAO Rong. Research and application progress of castor oil-based downstream products and its plasticizer[J]. Chemical Industry and Engineering Progree, 2015, 34(07): 1983-1988,2002.

许伟, 葛小东, 金丽珠, 邵荣. 蓖麻油基下游产物及蓖麻油增塑剂的研究及其应用进展[J]. 化工进展, 2015, 34(07): 1983-1988,2002.

References

[1] Dias J M, Araujo J M, Costa J F, et al. Biodiesel production from raw castor oil[J]. Energy, 2013, 53:58-66.
[2] Zeng Q F, Dong G N. Influence of load and sliding speed on super-low friction of nitinol 60 alloy under castor oil lubrication[J]. Tribology Letters, 2013, 52(1):47-55.
[3] 吴杰. 环氧乙酰蓖麻油酸甲酯的工艺研究[J]. 农业机械, 2011, 61(4):61-64.
[4] Doudin K, Al-Malaika S, Dole H, et al. Effect of contact surfaces on the thermal and photooxidation of dehydrated castor oil[J]. Polymer Degradation and Stability, 2011, 96:438-454.
[5] Amador P, Martinez E, Sanchez-Daza O, et al. Energies of combustion and standard molar enthalpies of formation of ricinoleic acid and methyl ricinoleate[J]. J. Chem. Thermodynamics, 2012, 50:15-18.
[6] Dupe A, Achard M, Fischmeister C, et al. Methyl ricinoleate as platform chemical for simultaneous production of fine chemicals and polymer precursors[J]. ChemSusChem, 2012, 5(11):2249-2254.
[7] Rejaibi M, Bigot S, Kebir N, et al. Elaboration of novel biosourced AA-BB polyamides with dangling chains from methyl ricinoleate[J]. European Journal of Lipid Science and Technology, 2014, 116(7):918-927.
[8] Reddy K K, Ravinder T, Kanjilal S. Synthesis and evaluation of antioxidant and antifungal activities of novel ricinoleate-based lipoconjugates of phenolic acids[J]. Food Chemistry, 2012, 134(4):2201-2207.
[9] Gomes N, Teixeira J A, Belo I. Fed-batch versus batch cultures of yarrowia lipolytica for gamma-decalactone production frommethyl ricinoleate[J]. Biotechnology Letters, 2012, 34(4):649-654.
[10] Miao X, Malacea R, Fischmeister C, et al. Ruthenium-alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile andmethyl acrylate:A key step toward long-chain bifunctional and amino acid compounds[J]. Green Chemistry, 2011, 13(10):2911-2919.
[11] Amador P, Martinez E, Sanchez-Daza O, et al. Energies of combustion and standard molar enthalpies of formation of ricinoleic acid and methylricinoleate[J]. Journal of Chemical Thermodynamics, 2012, 50:15-18.
[12] Panwar N L, Shrirame H Y, Rathore N S, et al. Performance evaluation of a diesel engine fueled with methyl ester of castor seed oil[J]. Applied Thermal Engineering, 2010, 30:245-249.
[13] Meller E, Green U, Aizenshtat Z, et al. Catalytic deoxygenation of castor oil over Pd/C for the production of cost effective biofuel[J]. Fuel, 2014, 133:89-95.
[14] Albuquerque A D, Maul J, Santos J P, et al. Estimation of the oxidation temperature of biodiesels from a limited number of chemical parameters[J].Fuel, 2012, 102:585-591.
[15] Sharmin E, Akram D, Zafar F, et al. Plant oil polyol based poly(ester urethane) metallohybrid coatings[J]. Progress in Organic Coatings, 2012, 73(1):118-122.
[16] Ning Z Y, Zhang Q S, Wu Q P, et al. Efficient synthesis of hydroxyl functioned polyesters from natural polyols and sebacic acid[J]. Chinese Chemical Letters, 2011, 22(6):635-638.
[17] Sharmin E, Alam M S, Philip R K, et al. Linseed amide diol/DGEBA epoxy blends for coating applications:Preparation, characterization, ageing studies and coating properties[J]. Progress in Organic Coatings, 2010, 67(2):170-179.
[18] Ning Z Y, Zhang Q S, Wu Q P, et al. Efficient synthesis of hydroxyl functioned polyesters from natural polyols and sebacic acid[J]. Chinese Chemical Letters, 2011, 22:635-638.
[19] Djordjevic I, Choudhury N R, Dutta, N K, et al. Synthesis and characterization of novel citric acid-based polyester elastomers[J]. Polymer, 2009, 50:1682-1691.
[20] Zhang Z, Chen L B, Gao J, et al. Preparation of poly(sebacic anhydride) and polylactic acid pills used as drug carrier for levofloxacin controlled release[J]. Journal of Polymer Engineering, 2013, 33(7):659-664.
[21] Levy-Nissenbaum E, Khan W, Pawar R P, et al. Pharmacokinetic and efficacy study of cisplatin and paclitaxel formulated in a new injectable poly(sebacic-co-ricinoleic acid) polymer[J]. European Journal of Pharmaceutics and Biopharmaceutics, 2012, 82(1):85-93.
[22] Samano C, Cifuentes F, Morales M A. Neurotransmitter segregation:Functional and plastic implications[J]. Progress in Neurobiology, 2012, 97(3):277-287.
[23] de Meirleir N, Pellens L, Broeckx W, et al. The rheological properties of hydrogenated castor oil crystals[J]. Colloid and Polymer Science, 2014, 292(10):2539-2547.
[24] Alwaseem H, Donahue CJ, Marincean S. Catalytic transfer hydrogenation of castor oil[J]. Journal of Chemical Education, 2014, 91(4):575-578.
[25] Sinadinovic-Fiser S, Jankovic M, Borota O. Epoxidation of castor oil with peracetic acid formed in situ in the presence of an ion exchange resin[J]. Chemical Engineering and Processing, 2012, 62:106-113.
[26] Abbasi E, Vatankhah M, Hosseini Y, et al. Synthesis, structure, and mechanical properties of castor oil-based polyamidoamines toughenedepoxy coatings[J]. Journal of Applied Polymer Science, 2013, 128(6):4023-4030.
[27] Santacesaria E, Tesser R. A biphasic model describing soybean oil epoxidation with H₂O₂in a fed-batch reactor[J]. Chemical Engineering Journal, 2011, 173:198-209.
[28] Chen S B, Wang Q H, Wang T M. Physical properties of aramid fiber reinforced castor oil-based polyurethane/epoxy resin IPN composites[J]. Journal of Reinforced Plastics and Composites, 2013, 32(15):1136-1142.
[29] Zhang C Q, Li Y Z, Chen R Q, et al. Polyurethanes from solvent-free vegetable oil-based polyols[J]. Sustainable Chemistry & Engineering, 2014, 2(10):2465-2476.
[30] Fu C Q, Yang Z, Zheng Z T, et al. Properties of alkoxysilane castor oil synthesized via thiol-ene and its polyurethane/siloxane hybrid coating films[J]. Progress in Organic Coating, 2014, 77(8):1241-1248.
[31] Gurunathan T, Mohanty S, Nayak S K. Preparation and performance evaluation of castor oil-based polyurethane prepolymer/polylactide blends[J]. Journal of Materials Science, 2014, 49(23):8016-8030.
[32] Eceiza A, Caba K, Martin M D, et al. Thermoplastic polyurethane elastomers based on polycarbonate diol with different soft segment molecular weight and chemical structure:Mechanical and thermal properties[J]. Polymer Engineering and Science, 2008, 48:297-306.
[33] Alam M, Akra D, Sharmin E, et al. Vegetable oil based eco-friendly coating materials:A review article[J]. Arabian Journal of Chemistry, 2014, 7(4):469-479.
[34] Choi T, Weksler J, Padsalgikar A, et al. Influence of soft segment composition on phase-separated microstructure of polydimethylsiloxane-based segmented polyurethanes copolymers[J]. Polymer, 2009, 50:2320-2327.
[35] Bakhshi H, Yeganeh H, Yari A, et al. Castor oil-based polyurethane coatings containing benzyl triethanol ammonium chloride:Synthesis, characterization, and biological properties[J]. Journal of Materials Science, 2014, 49(15):5365-5377.
[36] Rueda-Larraz L, Fernández d'Arlas B, Tercjak A, et al. Synthesis and structure behaviour of segmented polyurethanes based on a tbiodegradable PCL-PTHF-PCL block copolymer as soft segment[J]. European Polymer Journal, 2009, 45:2096-2109.
[37] Hablot E, Zheng D, Bouquey M, et al. Polyurethane based on castor oil:Kinetics, chemical, mechanical and thermal properties[J]. Macromol Mater Engineering, 2008, 293:922-929.
[38] Santos W L F, Silva A J P, Cabral A A, et al. Particleboard manufactured from tauari (couratari oblongifolia) wood waste using castor oilbased polyurethane resin[J]. Materials Research- Ibero-American Journal of Materials, 2014, 17(3):657-663.
[39] Corcuera M A, Rueda L. Microstructure and properties of polyurethanes derived from castor oil[J]. Polymer Degradation and Stability, 2010, 95:2175-2184.
[40] Thakur S, Karak N. Castor oil-based hyperbranched polyurethanes as advanced surface coating materials[J]. Progress in Organic Coatings, 2013, 76:157-164.
[41] Du J J, Zuo Y, Zou Q, et al. Preparation and in vitro evaluation of polyurethane composite scaffolds based on glycerol esterified castor oil and hydroxyapatite[J]. Materials Research Innovations, 2014, 18(3):160-168.
[42] Deka H, Karak N. Bio-based hyperbranched polyurethanes for surface coating applications[J]. Progress in Organic Coatings, 2009, 66:192-198.
[43] Shaik A, Narayan R, Raju K V S N. Synthesis and properties of siloxane-crosslinked polyurethane-urea/silica hybrid films fromcastor oil[J]. Journal of Coatings Technology and Research, 2014, 11(3):397-407.
[44] Mohamed H A, Badran B M, Rabie A M, et al. Synthesis and characterization of aqueous (polyurethane/aromatic polyamide sulfone) copolymer dispersions from castor oil[J]. Progress in Organic Coating, 2014, 77(5):965-974.
[45] Saralegi A, Gonzalez M L, Valea A, et al. The role of cellulose nanocrystals in the improvement of the shape-memory properties of castoroil-based segmented thermoplastic polyurethanes[J]. Composites Science and Technology, 2014, 92:27-33.
[46] Abbasi E, Vatankhah M, Hosseini Y, et al. Synthesis, structure and mechanical properties of castor oil-based polyamidoamines toughened epoxy coatings[J]. Applied Polymer, 2012, 128(6):4023-4030.
[47] Farag S, Fu D B, Jessop P G, et al. Detailed compositional analysis and structural investigation of a bio-oil from microwave pyrolysis of kraft lignin[J]. Journal of Analytical and Applied Pyrolysis, 2014, 109:249-257.
[48] Tokiwa Y, Kitagawa M, Raku T, et al. Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis[J]. Bioorganic&Medicinal Chemistry Letters, 2007, 17:3105-3108.
[49] Samano C, Cifuentes F, Morales M A. Neurotransmitter segregation:
Functional and plastic implications[J]. Progress in Neurobiology, 2012, 97(3):277-287.
[50] Chua S C, Xu X B, Guo Z. Emerging sustainable technology for epoxidation directed toward plant oil-based plasticizers[J]. Process Biochemistry, 2012, 47:1439-1451.
[51] 佟拉嘎. 蓖麻油基精细化工产品的研究开发进展[J]. 北京石油化工学院学报, 2010, 18(1):58-61.
[52] Jankovic M R, Sinadinovic-Fiser S V, Govedarica O M. Kinetics of the epoxidation of castor oil with peracetic acid formed in situ in the presence of an ion-exchange resin[J]. Industrial & Engineering Chemistry Research, 2014, 53(22):9357-9364.
[53] Liu S W, Li L, Yu S T, et al. Polymerization of fatty acid methyl ester using acidic ionic liquid as catalyst[J]. Chinese Journal of Catalysis, 2010, 31(12):1433-1438.
[54] Elsheikh Y A. Bronsted imidazolium ionic liquids:Synthesis and comparison of their catalytic activities as pre-catalyst for biodiesel production through two stage process[J]. Energy Conversion and Management, 2011, 52(2):804-809.
[55] 李存燕, 李为民. 离子液体催化制备乙酰蓖麻油酸甲酯的工艺研究[J]. 中国油脂, 2011, 36(8):56-59.
[56] De B, Gupta K, Mandal M, et al. Biodegradable hyperbranched epoxy from castor oil-based hyperbranched polyester polyol[J]. Sustainable Chemistry & Engineering, 2014, 2(3):445-453.