Castor oil as a renewable resource for the chemical industry

European Journal of Lipid Science and Technology - Tập 112 Số 1 - Trang 10-30 - 2010
Hatice Mutlu1, Michaël A. R. Meier1,2
1University of Applied Sciences Oldenburg/Ostfriesland/Wilhelmshaven, Emden, Germany
2University of Potsdam, Institute of Chemistry, Golm, Germany

Tóm tắt

Abstract

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.

Từ khóa


Tài liệu tham khảo

10.1016/0378-8741(82)90038-1

FAOSTAT: FAO onlinehttp://faostat.fao.org 2008.

Brickell C., 2008, The RHS Gardener's Encyclopedia of Plants and Flowers

Atsman D., 1989, Oil Crops of the World, 438

http://www.cambridge2000.com/castor/

10.1016/B978-0-08-045316-3.00003-X

Anderson D., 2005, Bailey's Industrial Oil and Fat Products, 1

Kemper T. G., 2005, Bailey's Industrial Oil and Fat Products, 57

Ali M. F., 2005, Handbook of Industrial Chemistry: Organic Chemicals, 86

Ambekar V. R., 1957, Detoxification of castor cake., Indian J Dairy Sci., 10, 107

10.1081/TXR-120030648

10.1007/BF02633795

10.1007/BF02546065

10.1016/S0091-3057(99)00007-6

10.1016/j.anifeedsci.2004.10.002

10.1016/j.indcrop.2008.09.006

Okorie A. U., 1985, Heat‐treated castor oil bean (Ricinus communis): A potential livestock protein‐supplement in the tropics, Nutr Rep Int., 32, 659

Rao N. P., 1988, Utilization of autoclaved castor bean meal in concentrate ration for sheep, Indian J Anim Nutr, 5, 121

10.1007/BF02672540

10.1039/jr9470000753

Brink M., 2006, Plant Resources of Tropical Africa. 1. Cereals and Pulses, 144

Verhé R. G., 2004, Renewable Bioresources: Scope and Modification for Non‐Food Applications, 208

10.1002/jsl.3000190305

BASF:http://www.basf.com 2009

Arkema:http://www.arkema‐inc.com 2009

10.1021/jo01066a067

10.1007/BF02638857

10.1016/j.indcrop.2005.10.004

F.Ahmad H.Schiller K. D.Mukherjee:Lipids containing isoricinoleoyl (9‐hydroxy‐cis‐12‐octadecenoyl) moieties in seeds of Wrightia species. Lipids.1986 21 486–490.

10.1021/ie070761b

10.1201/9781420077070.ch6

10.1007/s10722-007-9244-3

Lavanya C., 2003, Development of wilt resistant pistillate lines in castor through mutation breeding., J Oilseed Res., 20, 48

10.2135/cropsci2004.7600

10.1042/bj2870141

10.1016/S0926-6690(97)00029-0

McKeon T. A., 2002, Lipid Biotechnology, 129

10.1300/J153v03n03_03

10.1042/BST0280947

10.1021/ie50370a010

10.1007/BF02637767

10.1007/BF02639914

10.1007/BF02637515

Boeseken J., 1930, Action of maleic anhydride on 9,11‐octadecadienic acid and its ethyl ester. The products of the dehydration of ricinoleic acid, Rec Trev Chim., 49, 1165

10.1007/BF02639652

10.1021/i360061a022

10.1021/ie50364a025

10.1007/BF02638537

10.1007/BF02635584

10.1007/BF02582184

10.1007/BF02545511

10.1007/BF02662284

10.1021/ie50425a028

Weiss E. A., 1971, Castor, Sesame and Safflower

10.1002/pi.1995.210360403

10.1007/BF02697813

Ogunniyi D. S., 2000, Preparation and evaluation of alkyd resin from castor oil., Pak J Sci Ind Res., 43, 378

10.1108/03699420210442347

Onukwlo O. D., 2008, Production and characterization of castor oil‐modified alkyd resins., J Eng Appl Sci., 3, 161

10.1007/BF02638830

10.1007/BF00000015

10.1007/BF02646283

10.1007/BF02540143

10.1007/BF02646783

10.1021/ie50445a022

10.1007/BF02670036

10.1007/BF00724010

H.Iwamatsu M.Akiyama Y.Miyamoto S.Okamura: US Patent Application 20080305973 (2008).

10.1007/BF01130493

J. F.Barnes: US Patent 5 126 062 (1992).

10.1108/eb041574

R. A.Lindner E.Dudek: US Patent 5 426 144 (1995).

10.1007/BF02638517

Adhvaryu A., 2005, Industrial Uses of Vegetable Oils, 14

10.1007/BF02890753

10.1007/BF02544763

Flinn R. A., 1978, Encyclopedia of Chemical Processing and Design, 401

Domsch A., 1994, Chemistry and application of undecylenic acid and derivatives thereof for cosmetics., SÖFW J., 120, 322

Hunting A. L. L., 1981, Properties and uses of undecylenic acid and derivatives., Cosmet Toiletries, 96, 29

10.1016/j.ejmech.2004.10.003

10.1007/s11745-006-1397-x

10.1002/ejlt.200800024

Green M. M., 2003, Organic Chemistry Principles and Industrial Practice, 107

10.1002/cssc.200900075

10.1007/BF02523370

10.1007/BF02636251

10.1021/ja01303a018

Gupta A. S., 1954, 10‐Undecenoic acid and heptaldehyde from castor oil., J Sci Ind Res (India), 13, 277

Figueriredo M. K.‐K., 2009, Low temperature conversion (LCT) of castor seeds – A study of the oil fraction (pyrolysis oil)., J Anal Appl Pyrolysis.

10.1007/BF02682613

G.Wetroff L.Thillay G.D'Ivacheff J.Khaladgi: US Patent 2 807 633 (1957).

Hu H. B., 2000, Optimization of production temperatures of heptaldehyde and methyl undecenoate from methyl ricinoleate by pyrolysis process., J Ind Eng Chem., 6, 238

10.1016/j.jaap.2003.12.008

10.1016/0040-4020(60)80033-6

10.1016/0040-4020(60)80033-6

10.1007/BF02541184

10.1007/BF02680037

10.1007/BF02582593

Adams R., 1921, Methylhexylcarbinol (capryl alcohol), Org Synth, 1, 61

Verma J. P., 1949, Sebacic acid and secondary octyl alcohol from castor oil., J Sci Ind Res., 8, 183

10.1007/BF02539685

C. D.Ries T. S.Totah: US Patent 5 952 517 (1999).

R. L.Logan S. V.Udeshi: US Patent 6 392 074 (2002).

10.1021/ie071345u

10.1016/S0169-409X(03)00036-X

10.1016/j.eurpolymj.2006.09.008

10.1016/j.polymer.2009.01.045

R. T.Sanderson N. Y.Fishkill: US Patent 2 628 974 (1953).

V.Bergeret al.: US Patent 6 111 055 (2000).

A. W.Fogel: US Patent 6 126 951 (2000).

10.1016/0142-9612(86)90007-4

10.1021/bm700924n

10.1089/ten.tea.2008.0326

10.1080/15583720701834224

Z. S.Petrovic M.Ionescu I.Javni: US Patent Application 20090082483 (2009).

10.1590/S0100-40422008000800031

10.1007/s11746-009-1361-z

10.1177/0095244308091785

10.1002/app.27783

10.1002/app.29468

10.1002/app.26623

10.1016/j.eurpolymj.2003.12.013

10.1016/j.polymer.2006.09.057

10.1016/S0039-9140(02)00122-4

10.1002/pat.274

10.1016/j.polymdegradstab.2006.10.011

10.1002/pen.20602

10.1016/j.nimb.2007.08.032

10.1002/app.28401

Kendaganna Swamy B. K., 2003, Structure‐property relationship of castor oil based diol chain extended polyurethanes., J Mater Sci., 38, 453

10.1002/(SICI)1099-1581(199604)7:4<197::AID-PAT514>3.0.CO;2-4

10.1002/pi.1994.210350201

10.1016/S0032-3861(99)00471-1

10.1081/MC-120018018

Sperling L. H., 1977, Novel plastics and elastomers from simultaneous interpenetrating networks from castor oil based IPNs – a review of an international program., Polym Sci Technol., 10, 113

10.1081/MC-100100576

10.1002/app.11839

10.1016/j.progpolymsci.2006.07.001

10.1002/pen.760170505

10.1002/app.1977.070210609

10.1002/pen.760211502

10.1002/pen.760170408

10.1002/pen.760191211

10.1002/pen.760191210

10.1016/0014-3057(93)90245-B

10.1016/S0014-3057(97)00282-6

10.1002/pen.760331408

10.1002/(SICI)1097-4628(19970516)64:7<1393::AID-APP19>3.0.CO;2-Y

10.1002/pola.1987.080250821

10.1002/pola.1989.080270915

10.1002/app.1987.070340520

10.1002/app.1993.070501214

10.1002/app.20930

10.1590/S1516-14392004000400006

10.1007/BF02706727

10.1208/pt040451

10.1021/i360011a002

10.1002/ejlt.200800027

10.1023/B:TOCA.0000013544.89226.c4

10.1021/cr050989d

10.1039/c39720001221

10.1021/ja952676d

10.1002/anie.199520391

10.1021/ol990909q

10.1016/S0040-4039(99)00217-8

10.1007/s11746-006-1249-0

10.1039/b712293d

10.1039/b808930b

10.1016/j.apcata.2008.10.026

10.1039/B816917A

10.1002/cssc.200900028

10.1002/cssc.200900091

10.1002/adsc.200800726

Djigoue G. B., Improving the selectivity for the synthesis of two renewable platform chemicals via olefin metathesis., Appl Catal A.

10.1002/cssc.200800047

10.1002/marc.200800365

Montero de Espinosa L., Fatty acid derived phosphorus‐containing polyesters via acyclic diene metathesis (ADMET) polymerization, J Polym Sci A Polym Chem.

10.1002/macp.200900045

10.1002/mame.200700209

10.1002/app.22994

10.1007/BF02699576

10.1080/10601320500206903

10.1002/app.22138

10.1002/ejlt.200501168

10.1002/app.22322

10.1002/(SICI)1099-0518(19990815)37:16<3337::AID-POLA32>3.0.CO;2-S

10.1002/(SICI)1097-4636(19990605)45:3<258::AID-JBM14>3.0.CO;2-W

10.1002/pola.10651

10.1021/bm050648

10.1002/1439-2054(20001101)283:1<15::AID-MAME15>3.0.CO;2-I

10.1002/app.24548

10.1002/app.24423

Ionescu M., 2005, Chemistry and Technology of Polyols for Polyurethanes, 435

10.1016/j.porgcoat.2008.07.001

10.1016/j.porgcoat.2007.06.002

10.1016/j.eurpolymj.2009.02.007

10.1016/j.porgcoat.2008.08.006