Castor oil as a renewable resource for the chemical industry

Castor oil is, as many other plant oils, a very valuable renewable resource for the chemical industry. This review article provides an overview on this specialty oil, covering its production and properties. More importantly, the preparation, properties and major application possibilities of chemical derivatives of castor oil are highlighted. Our discussion focuses on application possibilities of castor oil and its derivatives for the synthesis of renewable monomers and polymers. An overview of recent developments in this field is provided and selected examples are discussed in detail, including the preparation and characterization of castor oil-derived polyurethanes, polyesters and polyamides.

[1]  G. C. Bailey,et al.  Olefin Disproportionation. A New Catalytic Process , 1964 .

[2]  Michael J Yaszemski,et al.  Synthesis and evaluation of novel biodegradable hydrogels based on poly(ethylene glycol) and sebacic acid as tissue engineering scaffolds. , 2008, Biomacromolecules.

[3]  J. A. Posada,et al.  Preparation and Properties of Polyurethanes based on Castor Oil Chemically Modified with Yucca Starch Glycoside , 2009 .

[4]  F. Anugwa,et al.  Heat-treated castor oil bean (Ricinus communis) : a potential livestock protein-supplement in the tropics , 1985 .

[5]  T. Hefferan,et al.  Potential of hydrogels based on poly(ethylene glycol) and sebacic acid as orthopedic tissue engineering scaffolds. , 2009, Tissue engineering. Part A.

[6]  R. K. Mendes,et al.  Evaluation of a new rigid carbon-castor oil polyurethane composite as an electrode material. , 2002, Talanta.

[7]  L. A. Goldblatt,et al.  Chromatographie analysis of seed oils. Fatty acid composition of castor oil , 1962 .

[8]  R. Grubbs,et al.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. , 1999, Organic letters.

[9]  P. Nayak.  Natural Oil-Based Polymers: Opportunities and Challenges , 2000 .

[10]  Y. Yagcı,et al.  Styrenation of castor oil and linseed oil by macromer method , 2000 .

[11]  C. Cunha,et al.  Pharmacological Evaluation of Ricinine, a Central Nervous System Stimulant Isolated from Ricinus communis , 1999, Pharmacology Biochemistry and Behavior.

[12]  P. Vijayalakshmi,et al.  Composition of fatty acids obtained by decomposition of castor oil fatty acid estolides , 1982 .

[13]  C. Winder.  Toxicity of Ricin , 2004 .

[14]  A. Domb,et al.  Ricinoleic acid-based biopolymers. , 1999, Journal of biomedical materials research.

[15]  S. Anandan,et al.  Effect of different physical and chemical treatments on detoxification of ricin in castor cake , 2005 .

[16]  Avanish Kumar Srivastava,et al.  Interpenetrating polymer networks : a review on synthesis and properties , 1994 .

[17]  S. Stymne,et al.  Evidence for cytochrome b5 as an electron donor in ricinoleic acid biosynthesis in microsomal preparations from developing castor bean (Ricinus communis L.). , 1992, The Biochemical journal.

[18]  V. Athawale,et al.  Recent Developments in Polyurethanes and Poly(acrylates) Interpenetrating Polymer Networks , 2003 .

[19]  M. Meier,et al.  Improving the selectivity for the synthesis of two renewable platform chemicals via olefin metathesis , 2009 .

[20]  Shuren Yao,et al.  Synthesis and dynamic mechanical behavior of crosslinked copolymers and IPNs from vegetable oils , 2003 .

[21]  Field correlators in Abelian projected theories and stochastic vacuum model , 2000, hep-ph/0006156.

[22]  M. Dwivedi,et al.  Total vegetable-oil based greases prepared from castor oil , 2002 .

[23]  L. Sperling,et al.  Semi‐interpenetrating polymer networks composed of poly(ethylene terephthalate) and castor oil: Synthesis, structure, and properties , 1993 .

[24]  G. Lemiére,et al.  Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. , 2005, European journal of medicinal chemistry.

[25]  B. Freedman,et al.  Dehydrogenation of methyl 12-hydroxystearate to methyl 12-ketostearate with Raney nickel , 1966 .

[26]  A. Domb,et al.  Poly(ester anhydride)s prepared by the insertion of ricinoleic acid into poly(sebacic acid) , 2003 .

[27]  R. Grubbs,et al.  Increased ring closing metathesis activity of ruthenium-based olefin metathesis catalysts coordinated with imidazolin-2-ylidene ligands , 1999 .

[28]  A. Gandini,et al.  Preparation of acrylated and urethanated triacylglycerols , 2006 .

[29]  Jerry Horton,et al.  A cooker-extruder for deallergenation of castor bean meal , 1989 .

[30]  B. Suthar,et al.  Interpenetrating polymer networks from castor oil-based polyurethanes and poly(methyl methacrylate). V , 1987 .

[31]  Liucheng Zhang,et al.  Study on the properties, morphology, and applications of castor oil polyurethane—poly(methyl methacrylate) IPNs , 1997 .

[32]  Joseph W. Ziller,et al.  A Series of Well‐Defined Metathesis Catalysts–Synthesis of [RuCl2(CHR′)(PR3)2] and Its Reactions , 1995 .

[33]  T. Foglia,et al.  Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α,ω-dicarboxylic acids , 2006 .

[34]  E. Frankel,et al.  Hydroxyaliphatic acids in branched copolymers with acyl chloride-terminated long side chains: A new shrink-resist treatment for wool , 1971 .

[35]  Christian V. Stevens,et al.  Industrial products from lipids and proteins , 2004 .

[36]  T. Mckeon,et al.  Biosynthesis of Ricinoleic Acid for Castor-Oil Production , 2002 .

[37]  J. Ravel,et al.  Worldwide genotyping of castor bean germplasm (Ricinus communis L.) using AFLPs and SSRs , 2008, Genetic Resources and Crop Evolution.

[38]  J Kost,et al.  Polyanhydrides for controlled release of bioactive agents. , 1986, Biomaterials.

[39]  M. J. Diamond,et al.  Alkaline cleavage of hydroxy unsaturated fatty acids and derivatives. II 10-hydroxydecanoic acid from ricinoleates and 1,10-decanediol from ricmoleyl alcohol , 1967 .

[40]  O. Grummitt,et al.  Alternative methods for dehydrating castor oil , 1953 .

[41]  C. Stevens,et al.  Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. , 2009, ChemSusChem.

[42]  M. Meier,et al.  Unsaturated PA X,20 from Renewable Resources via Metathesis and Catalytic Amidation , 2009 .

[43]  Zoran S. Petrović,et al.  Polyurethanes from Vegetable Oils , 2008 .

[44]  J. W. Barlow,et al.  Polymer blends and alloys—a review of selected considerations , 1981 .

[45]  Cédric Fischmeister,et al.  First Transformation of Unsaturated Fatty Esters Involving Enyne Cross-Metathesis , 2009 .

[46]  A. T. Erciyes,et al.  The decomposition of secondary esters of castor oil with fatty acids , 1991 .

[47]  J. G. Kane,et al.  Studies on castor oil. II. Hydrogenation of castor oil , 1957 .

[48]  V. R. Ambekar,et al.  Detoxication of castor cake. , 1957 .

[49]  F. Naughton.  Production, chemistry, and commercial applications of various chemicals from castor oil , 1974 .

[50]  M. Meier,et al.  Acyclic diene metathesis with a monomer from renewable resources: control of molecular weight and one-step preparation of block copolymers. , 2008, ChemSusChem.

[51]  A. Palanisamy,et al.  Photo-DSC and dynamic mechanical studies on UV curable compositions containing diacrylate of ricinoleic acid amide derived from castor oil , 2007 .

[52]  M. Meier,et al.  Acyclic Triene Metathesis Polymerization with Chain-Stoppers : Molecular Weight Control in the Synthesis of Branched Polymers , 2008 .

[53]  D. Braasch,et al.  Degradation of ricin in castor seed meal by temperature and chemical treatment , 2009 .

[54]  D. Hayes,et al.  The triglyceride composition, structure, and presence of estolides in the oils ofLesquerella and related species , 1995 .

[55]  C. Boelhouwer,et al.  Metathesis of unsaturated fatty acid esters by a homogeneous tungsten hexachloride–tetramethyltin catalyst , 1972 .

[56]  A. K. Vasishtha,et al.  Sebacic acid and 2-octanol from castor oil , 1990 .

[57]  V. T. Bui,et al.  Synthesis and properties of radiation modified thermally cured castor oil based polyurethanes , 2007 .

[58]  R. Wool,et al.  Soybean and castor oil based monomers: Synthesis and copolymerization with styrene , 2006 .

[59]  Hamid Yeganeh,et al.  Preparation and properties of novel biodegradable polyurethane networks based on castor oil and poly(ethylene glycol) , 2007 .

[60]  A. Scarpa,et al.  Various uses of the castor oil plant (Ricinus communis L.). A review. , 1982, Journal of ethnopharmacology.

[61]  Wei Zhang,et al.  Polyester polyols and polyurethanes from ricinoleic acid , 2008 .

[62]  T. Mckeon,et al.  Development of Castor with Reduced Toxicity , 2001 .

[63]  M. Meier,et al.  Cross-metathesis of fatty acid derivatives with methyl acrylate: renewable raw materials for the chemical industry , 2007 .

[64]  R. Wool,et al.  Soybean‐ and castor‐oil‐based thermosetting polymers: Mechanical properties , 2006 .

[65]  I. Wolff,et al.  Lesquerolic Acid. A New Hydroxy Acid from Lesquerella Seed Oil1a , 1961 .

[66]  B. Mackey,et al.  Temperature and elevation effects on plant growth, development, and seed production of two Lesquerella species , 2006 .

[67]  L. N. Owen,et al.  143. Reactions of carbinols in the presence of alkali. Part II. The scission of ricinoleic acid , 1947 .

[68]  R. Larock,et al.  Rubbery Thermosets by Ring‐Opening Metathesis Polymerization of a Functionalized Castor Oil and Cyclooctene , 2007 .

[69]  Hong-bo Hu,et al.  Optimization of production temperatures of heptaldehyde and methyl undecenoate from methyl ricinoleate by pyrolysis process , 2000 .

[70]  I. Djordjevic,et al.  Synthesis and characterization of novel citric acid-based polyester elastomers , 2009 .

[71]  J. Dubois,et al.  Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile , 2009 .

[72]  E. G. Bobalek,et al.  Synthesis of drying oils by thermal splitting of secondary fatty acid esters of castor oil , 1954 .

[73]  Eric Cloutet,et al.  Polyurethane nanoparticles from a natural polyol via miniemulsion technique , 2006 .

[74]  M. Meier,et al.  Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact , 2008 .

[75]  H. Moeini.  Preparation and properties of novel green poly(ether–ester urethane)s insulating coatings based on polyols derived from glycolyzed PET, castor oil, and adipic acid and blocked isocyanate , 2007 .

[76]  G. W. Priest,et al.  Composition and Analysis of Dehydrated Castor Oil , 1940 .

[77]  A. Corma,et al.  Chemical routes for the transformation of biomass into chemicals. , 2007, Chemical reviews.

[78]  Hamid Yeganeh,et al.  Synthesis and properties of isocyanate curable millable polyurethane elastomers based on castor oil as a renewable resource polyol , 2004 .

[79]  F. Ahmad,et al.  Lipids containing isoricinoleoyl (9-hydroxy-cis-12-octadecenoyl) moieties in seeds ofWrightia species , 1986, Lipids.

[80]  C. Elliger,et al.  The effect of ammoniation upon ricinine in castor meal , 1972 .

[81]  U. Riaz,et al.  Compatibility Studies on Dehydrated Castor Oil Epoxy Blend with Poly(Methacrylic Acid) , 2005 .

[82]  Zhengdong Cheng,et al.  Polyurethanes sintetized of polyols obtained from castor oil modified by transesterification with pentaerythritol , 2008 .

[83]  N. Karak,et al.  Synthesis and Characterization of Castor-Oil-Modified Hyperbranched Polyurethanes , 2009 .

[84]  Kinam Park,et al.  Superporous IPN hydrogels having enhanced mechanical properties , 2003, AAPS PharmSciTech.

[85]  R. L. Terrill.  Dehydration of castor oil , 1950 .

[86]  Junzhe Guo,et al.  Properties of two kinds of room temperature cured interpenetrating polymer networks based on castor oil polyurethane , 1993 .

[87]  M. Meier,et al.  Metathesis as a versatile tool in oleochemistry , 2008 .

[88]  Gökhan Çaylı,et al.  Biobased polyisocyanates from plant oil triglycerides: Synthesis, polymerization, and characterization , 2008 .

[89]  A. Palanisamy,et al.  Synthesis, photo curing and viscoelastic properties of triacrylate compositions based on ricinoleic acid amide derived from castor oil , 2008 .

[90]  M. Meier,et al.  A design-of-experiments approach for the optimization and understanding of the cross-metathesis reaction of methyl ricinoleate with methyl acrylate. , 2009, ChemSusChem.

[91]  S. Ghosh,et al.  Study of hexafunctional polyol in high solids air-drying alkyd : Improved film performance , 2009 .

[92]  Kalappa Prashantha,et al.  Interpenetrating polymer networks based on polyol modified castor oil polyurethane and poly(2-hydroxyethylmethacrylate): Synthesis, chemical, mechanical and thermal properties , 2001 .

[93]  J. Manson,et al.  Simultaneous interpenetrating networks based on castor oil elastorners and polystyrene. IV. Stress-strain and impact loading behavior , 1979 .

[94]  S. Prasannakumar,et al.  Interpenetrating polymer networks based on polyol modified castor oil polyurethane and poly(2‐ethoxyethyl methacrylate): Synthesis, chemical, mechanical, thermal properties, and morphology , 2004 .

[95]  J. Fernández-martínez,et al.  Isolation of a Natural Mutant in Castor with High Oleic/Low Ricinoleic Acid Content in the Oil , 2004 .

[96]  K. C. Mundim,et al.  Diesel-like fuel obtained by pyrolysis of vegetable oils , 2004 .

[97]  G. Ma,et al.  Synthesis and in vitro cytotoxic activity of N-, F-, and S-ether derivatives of podophyllotoxin fatty acid adducts , 2005, Lipids.

[98]  Gel point prediction of metal‐filled castor oil‐based polyurethanes system , 2002 .

[99]  Dan Anderson,et al.  A Primer on Oils Processing Technology , 2005, Bailey's Industrial Oil and Fat Products.

[100]  M. Meier,et al.  Cross-metathesis reactions of allyl chloride with fatty acid methyl esters : Efficient synthesis of α,ω-difunctional chemical intermediates from renewable raw materials , 2009 .

[101]  A. K. Vasishtha,et al.  Heptaldehyde and undecylenic acid from castor oil , 1989 .

[102]  J. Manson,et al.  Castor oil based interpenetrating polymer networks, IV. Mechanical behavior , 1977 .

[103]  M. J. Diamond,et al.  Alkaline cleavage of hydroxy unsaturated fatty acids. I. Ricinoleic acid and lesquerolic acid , 1965 .

[104]  L. Kunst,et al.  Production of hydroxy fatty acids in the seeds of Arabidopsis thaliana. , 2000, Biochemical Society transactions.

[105]  L. Falkenburg,et al.  A Continuous process for the dehydration of castor oil , 1948 .

[106]  Leslie H. Sperling,et al.  The current status of interpenetrating polymer networks , 1996 .

[107]  Siddaramaiah,et al.  Structure-property relationship of castor oil based diol chain extended polyurethanes (PUs) , 2003 .

[108]  D. S. Ogunniyi,et al.  Preparation and evaluation of alkyd resin from castor oil , 2000 .

[109]  H. Frisch,et al.  Swollen interpenetrating polymer networks , 2000 .

[110]  A. Gandini,et al.  Acrylated vegetable oils as photocrosslinkable materials , 2006 .

[111]  I. Ahmad,et al.  Oleochemicals from Isoricinoleic Acid (Wrightia tinctoria Seed Oil) , 2008 .

[112]  C. Bruneau,et al.  A direct route to bifunctional aldehyde derivatives via self- and cross-metathesis of unsaturated aldehydes. , 2009, ChemSusChem.

[113]  K. Achaya.  Chemical derivatives of castor oil , 1971, Journal of the American Oil Chemists' Society.

[114]  V. Kale,et al.  High pressure splitting of castor oil , 1984 .

[115]  Jinchen Tang,et al.  Synthesis and characterization of elastic aliphatic polyesters from sebacic acid, glycol and glycerol , 2006 .

[116]  Zhengdong Cheng,et al.  Simultaneous Interpenetrating Polymer Networks of Polyurethane from Pentaerythritol–Modified Castor Oil and Polystyrene: Structure–Property Relationships , 2009 .

[117]  M. Meier,et al.  Fatty acid derived phosphorus‐containing polyesters via acyclic diene metathesis polymerization , 2009 .

[118]  A. Domb,et al.  Poly(sebacic acid-co-ricinoleic acid) biodegradable injectable in situ gelling polymer. , 2006, Biomacromolecules.

[119]  J. W. Rawlins,et al.  Thiol–ene UV-curable coatings using vegetable oil macromonomers , 2009 .

[120]  V. Athawale,et al.  Interpenetrating polymer networks based on polyol modified castor oil polyurethane and polymethyl methacrylate , 1998 .

[121]  B. Freedman,et al.  Catalytic dehydrogenation of methyl 12-hydroxystearate to methyl 12-ketostearate , 1966 .

[122]  J. Manson,et al.  Castor-oil-based interpenetrating polymer networks: Synthesis and characterization , 1977 .

[123]  Thomas McKeon.  Engineering Plants for Industrial Uses , 2009 .

[124]  J. Manson,et al.  Simultaneous interpetrating network based on castor oil elastomers and polystyrene. III. Morphology and glass transition behavior , 1979 .

[125]  M. J. Diamond,et al.  A convenient preparation of 10-hydroxydecanoic acid , 1972 .

[126]  K. Achaya,et al.  Hydrogenolysis of saturated, oleic and ricinoleic acids to the corresponding alcohols , 1964 .

[127]  A. Gandini,et al.  Materials from Vegetable Oils: Major Sources, Properties and Applications , 2008 .

[128]  A. Albertsson,et al.  Polyesters based on diacid monomers. , 2003, Advanced drug delivery reviews.

[129]  A. A. Vernon,et al.  Some Characteristics of the Residue from the Cracking of Castor Oil1 , 1936 .

[130]  J. Mol,et al.  Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils , 2004 .

[131]  C. Stevens,et al.  Undecylenic acid: A valuable renewable building block on route to Tyromycin A derivatives , 2008 .

[132]  C. A. Ferreira,et al.  Properties evaluation of the membranes synthesized with castor oil polyurethane and polyaniline , 2006 .

[133]  M. M. C. Forte,et al.  Study of castor oil polyurethane - poly(methyl methacrylate) semi-interpenetrating polymer network (SIPN) reaction parameters using a 2³ factorial experimental design , 2004 .

[134]  N. Krishnamurti.  Vinyl monomers from 12‐hydroxy stearic acid , 1980 .

[135]  J. G. Kane,et al.  Studies in estolides. I. Kinetics of estolide formation and decomposition , 1965 .

[136]  P. Patel,et al.  Interpenetrating polymer network from castor oil‐based polyurethanes and poly(methyl acrylate). XIV , 1989 .

[137]  Han Guobin,et al.  Study of reaction and kinetics in pyrolysis of methyl ricinoleate , 1996 .

[138]  A. R. Kelly,et al.  Lipase‐catalyzed synthesis of polyhydric alcohol‐poly(ricinoleic acid) ester star polymers , 2006 .

[139]  B. Freedman,et al.  Conversion of methyl ricinoleate to methyl 12-ketostearate with Raney nickel , 1965 .

[140]  Yusuf Yagci,et al.  Polymers from triglyceride oils , 2006 .

[141]  A. J. Stirton,et al.  Surface-active properties of salts of alpha-sulfonated acids and esters , 1954 .

[142]  J. Ziller,et al.  Synthesis and Applications of RuCl2(CHR‘)(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity , 1996 .

[143]  Nezihe Azcan and,et al.  Obtaining 2-Octanol, 2-Octanone, and Sebacic Acid from Castor Oil by Microwave-Induced Alkali Fusion , 2008 .

[144]  Y. P. S. Nirvan,et al.  Acrylate grafted dehydrated castor oil alkyd—A binder for exterior paints , 1998 .

[145]  O. Grummitt,et al.  Acetylated Castor Oil. , 1945 .

[146]  V. L. Hansley.  Sodium reduction of fatty acid esters , 1947 .

[147]  U. Riaz,et al.  Studies on miscibility of dehydrated castor oil epoxy blend with poly(methyl methacrylate) , 2006 .