Surfactants from renewable resources

Series Preface. Preface. Acknowledgements. List of Contributors. PART 1 RENEWABLE HYDROPHOBES. 1 Surfactants Based on Natural Fatty Acids (Martin Svensson). 1.1 Introduction and History. 1.2 Fats and Oils as Raw Materials. 1.3 Fatty Acid Soaps. 1.4 Polyethylene Glycol Fatty Acid Esters. 1.5 Polyglycerol Fatty Acid Esters. 1.6 Conclusions. References. 2 Nitrogen Derivatives of Natural Fats and Oils (Ralph Franklin). 2.1 Introduction. 2.2 Manufacture of Fatty Nitrogen Derivatives. 2.3 Production Data. 2.4 Ecological Aspects. 2.5 Biodegradation. 2.6 Properties of Nitrogen-Based Surfactants. 2.7 Applications. 2.8 Conclusions. References. 3 Surface-Active Compounds as Forest-Industry By-Products (Bjarne Holmbom, Anna Sundberg and Anders Strand). 3.1 Introduction. 3.2 Resin and Fatty Acids. 3.3 Sterols and Sterol Ethoxylates. 3.4 Hemicelluloses. Acknowledgements. References. PART 2 REWNEWABLE HYDROPHILES. 4 Surfactants Based on Carbohydrates and Proteins for Consumer Products and Technical Applications (Karlheinz Hill). 4.1 Introduction. 4.2 Raw Materials. 4.3 Products and Applications. 4.4 Conclusion. Acknowledgements. References. 5 Amino Acids, Lactic Acid and Ascorbic Acid as Raw Materials for Biocompatible Surfactants (Carmen Moran, Lourdes Perez, Ramon Pons, Aurora Pinazo and Maria Rosa Infante). 5.1 Introduction. 5.2 Production of Raw Materials. 5.3 Lysine-Based Surfactants. 5.4 Lactic Acid-Based Surfactants. 5.5 Ascorbic Acid-Based Surfactants. References. PART 3 NEW WAYS OF MAKING RENEWABLE BUILDING BLOCKS. 6 Ethylene from Renewable Resources (Anna Lundgren and Thomas Hjertberg). 6.1 Introduction. 6.2 Why Produce Ethylene from Renewable Resources? 6.3 Production of Ethylene from Renewable Feedstock. 6.4 Commercialization of Bioethylene. 6.5 Environmental Impact of Bioethylene. 6.6 Certificate of Green Carbon Content. 6.7 Concluding Remarks. References. 7 Fermentation-Based Building Blocks for Renewable Resource-Based Surfactants (Kris Arvid Berglund, Ulrika Rova, David B Hodge). 7.1 Introduction. 7.2 Existing and Potential Classes of Surfactants from Biologically-Derived Metabolites. 7.3 Fermentation-Based Building Blocks with Large Existing Markets. 7.4 New Fermentation-Based Building Blocks. Conclusion. References. PART 4 BIOSURFACTANTS. 8 Synthesis of Surfactants Using Enzymes (Patrick Adlercreutz and Rajni Hatti-Kaul). 8.1 Introduction. 8.2 Enzymes as Catalysts for Synthesis of Surfactants. 8.3 Enzymatic Synthesis of Polar Lipids Useful as Surfactants. 8.4 Carbohydrate Esters. 8.5 Fatty Amide Surfactants. 8.6 Amino Acid-Based Surfactants. 8.7 Alkyl Glycosides. 8.8 Future Prospects. Acknowledgements. References. 9 Surfactants from Waste Biomass (Flor Yunuen Garcia-Becerra, David Grant Allen, and Edgar Joel Acosta). 9.1 Introduction. 9.2 Surfactants Obtained from Biological Transformation of Waste Biomass. 9.3 Surfactants Obtained from Chemical Transformation of Waste Biomass. 9.4 Summary and Outlook. 9.5 References. 10 Lecithin and Other Phospholipids (Willem van Nieuwenhuyzen). 10.1 Introduction. 10.2 Sources and Production. 10.3 Composition. 10.4 Quality and Analysis of Lecithins. 10.5 Modification. 10.6 Emulsifying Properties. 10.7 Applications. 10.8 Legislation and Reach. 10.9 Conclusion. References. 11 Sophorolipids and Rhamnolipids (Dirk W. G. Develter and Steve J. J. Fleurackers). 11.1 Sophorolipids. 11.2 Derivatives of Native Sophorolipids. 11.3 Biosynthesis of Novel Sophorolipids. 11.4 Rhamnolipids. 11.5 Cleaning Applications Using Sophorolipids and Rhamnolipids. References. 12 Saponin-Based Surfactants (Wieslaw Oleszek and Arafa Hamed). 12.1 Introduction. 12.2 Molecular Properties. 12.3 Sources of Saponins. 12.4 Saponins as Emulsifiers and Surfactants. 12.5 Application of Saponins as Surfactants and Emulsifiers. Acknowledgements. References. PART 5 POLYMERIC SURFACTANTS/SURFACE-ACTIVE POLYMERS 13 Surface-Active Polymers from Cellulose (Leif Karlson). 13.1 Introduction. 13.2 Structure and Synthesis of Cellulose Ether. 13.3 Cellulose Ethers in Aqueous Solution. 13.4 Interaction with Surfactants. 13.5 Clouding. References. 14 New Developments in the Commercial Utilization of Lignosulfonates (Rolf Andreas Lauten, Bernt O. Myrvold and Stig Are Gundersen). 14.1 Introduction. 14.2 Lignosulfonates. 14.3 Lignosulfonate Production. 14.4 Environmental Issues. 14.5 Lignosulfonates as Stabilizers for Emulsions and Suspoemulsions. 14.6 Superplasticizers for Concrete. 14.7 Summary. Acknowledgements. References. 15 Dispersion Stabilizers Based on Inulin (Tharwat Tadros and Bart Levecke). 15.1 Introduction. 15.2 Solution Properties of Long-Chain Inulin and Hydrophobically Modified Inulin (HMI). 15.3 Interfacial Aspects of HMI at Various Interfaces. 15.4 Emulsions Stabilized Using HMI. 15.5 Emulsion Polymerization Using HMI. 15.6 Use of HMI for Preparation and Stabilization of Nanoemulsions. References Index.

[1]  M. Infante,et al.  Potential irritation of lysine derivative surfactants by hemolysis and HaCaT cell viability. , 2006, Toxicology letters.

[2]  B. Holmbom,et al.  Polysaccharides Dissolved from Norway Spruce in Thermomechanical Pulping and Peroxide Bleaching , 1994 .

[3]  E. Diczfalusy,et al.  The Ionization Constant, Solubility Product, and Solubility of Abietic and Dehydroabietic Acid. , 1958 .

[4]  M. Moresi,et al.  Direct ammonium fumarate production by Rhizopus arrhizus under phosphorous limitation , 2004, Biotechnology Letters.

[5]  Thomas F. Guetzloff,et al.  Does humic acid form a micelle , 1994 .

[6]  Kenneth Sundberg,et al.  Spruce-derived mannans – A potential raw material for hydrocolloids and novel advanced natural materials , 2008 .

[7]  D. Shah,et al.  Effect of degree, type, and position of unsaturation on the pKa of long-chain fatty acids. , 2002, Journal of colloid and interface science.

[8]  J. Zeikus,et al.  Biotechnology of succinic acid production and markets for derived industrial products , 1999, Applied Microbiology and Biotechnology.

[9]  B. Mattiasson,et al.  Lipase catalyzed acylation of glucose , 1994, Biotechnology Letters.

[10]  M. Infante,et al.  “Green” amino acid-based surfactants , 2004 .

[11]  J. Baeyens,et al.  Alkaline thermal sludge hydrolysis. , 2003, Journal of hazardous materials.

[12]  Christoph Berg,et al.  6 – World fuel ethanol – analysis and outlook , 2004 .

[13]  A. Mukherjee,et al.  Comparison of lipopeptide biosurfactants production by Bacillus subtilis strains in submerged and solid state fermentation systems using a cheap carbon source: Some industrial applications of biosurfactants , 2007 .

[14]  R. Mullen,et al.  Development and potential of genetically engineered oilseeds , 2005, Seed Science Research.

[15]  M. Johansson,et al.  Bio-based multifunctional fatty acid methyl esters as reactive diluents in coil coatings , 2019, Progress in Organic Coatings.

[16]  A. Gessesse,et al.  Synthesis of sucrose laurate using a new alkaline protease , 2003 .

[17]  G. Zacchi,et al.  Economic evaluation of isolation of hemicelluloses from process streams from thermomechanical pulping of spruce , 2007, Applied biochemistry and biotechnology.

[18]  S. Divakar,et al.  Lipase catalyzed synthesis of organic acid esters of lactic acid in non-aqueous media. , 2001, Journal of biotechnology.

[19]  A. Oikari,et al.  Free and conjugated resin acids in the bile of rainbow trout,Salmo gairdneri , 1984, Bulletin of environmental contamination and toxicology.

[20]  Carmen C. Tadini,et al.  Influence of vegetable shortening and emulsifiers on the unfrozen water content and textural properties of frozen French bread dough , 2005 .

[21]  K. Hanabusa,et al.  Supramolecular hydrogel formed by glucoheptonamide of l-lysine: simple preparation and excellent hydrogelation ability , 2007 .

[22]  B. Law,et al.  Glycosidases in organic solvents: I. Alkyl-β-glucoside synthesis in a water-organic two-phase system , 1990 .

[23]  T. Song,et al.  Extraction of galactoglucomannan from spruce wood with pressurised hot water , 2008 .

[24]  B. Diehl High resolution NMR spectroscopy , 2001 .

[25]  P. Fernandes,et al.  Phytosterols: applications and recovery methods. , 2007, Bioresource technology.

[26]  Guido Viscardi,et al.  Chemicals from wastes: compost-derived humic acid-like matter as surfactant. , 2006, Environmental science & technology.

[27]  S. Adachi,et al.  Condensation of L-Ascorbic Acid and Medium-Chain Fatty Acids by Immobilized Lipase in Acetonitrile with Low Water Content , 1999 .

[28]  Ramkrishna Sen,et al.  Towards commercial production of microbial surfactants. , 2006, Trends in biotechnology.

[29]  B. Ninham,et al.  Water of hydration in coagelsPresented at the 17th Conference of the European Colloid & Interface Science Society, Firenze, Italy, September 21?26, 2003. , 2004 .

[30]  D. Wei,et al.  Enzymatic synthesis of l-ascorbyl linoleate in organic media , 2006, Bioprocess and biosystems engineering.

[31]  M. Infante,et al.  Enzymatic synthesis of arginine-based cationic surfactants. , 1999, Biotechnology and bioengineering.

[32]  U. Bornscheuer,et al.  Lipase-catalyzed synthesis of vitamin C fatty acid esters , 1999, Biotechnology Letters.

[33]  Sanket J. Joshi,et al.  Biosurfactant production using molasses and whey under thermophilic conditions. , 2008, Bioresource technology.

[34]  W. V. Nieuwenhuyzen Lecithin production and properties , 1976 .

[35]  Zheng Guo,et al.  Lipase-catalyzed glycerolysis of fats and oils in ionic liquids : a further study on the reaction system , 2006 .

[36]  M. Kawaguchi,et al.  Surface Properties of Mono-, Di-, and Triglycerol Monostearate Monolayers Spread at the Air−Water Interface , 2001 .

[37]  B. Binks,et al.  Effects of temperature on the partitioning and adsorption of C12E5 in heptane–water mixtures , 1990 .

[38]  V. Tyagi,et al.  Cationic Gemini Surfactants: A Review , 2006 .

[39]  Hong Tan,et al.  Synthesis and antimicrobial characterization of novel l-lysine gemini surfactants pended with reactive groups , 2008 .

[40]  G. T. Tsao,et al.  Simultaneous Production and Recovery of Fumaric Acid from Immobilized Rhizopus oryzae with a Rotary Biofilm Contactor and an Adsorption Column , 1996, Applied and environmental microbiology.

[41]  Seong-Geun Oh,et al.  Stability of alkanoyl-6-O-ascorbates in various surfactant aggregates systems , 2002 .

[42]  G. Pastore,et al.  Production of biosurfactant by Bacillus subtilis LB5a on a pilot scale using cassava wastewater as substrate , 2008, Journal of Industrial Microbiology & Biotechnology.

[43]  Amino acid-based surfactants , 2004 .

[44]  P. Villeneuve Lipases in lipophilization reactions. , 2007, Biotechnology advances.

[45]  A. Nagao,et al.  Synthesis of O-Acyl-L-Homoserine by lipase , 1989 .

[46]  A. Kiener,et al.  Industrial biocatalysis today and tomorrow , 2001, Nature.

[47]  U. Bornscheuer,et al.  Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t-BuOH , 2005 .

[48]  P. Das,et al.  Water gelation of an amino acid-based amphiphile. , 2006, Chemistry.

[49]  Alexander M. Klibanov,et al.  Enzyme-catalyzed processes in organic solvents. , 1985 .

[50]  U. A. Budanova,et al.  pH-sensitive cationic lipopeptides for the design of drug-delivery systems , 2006, Russian Journal of Bioorganic Chemistry.

[51]  S. Udaka,et al.  STUDIES ON THE AMINO ACID FERMENTATION , 1957 .

[52]  M. Lenes,et al.  Stabilization of colloidal wood resin by dissolved material from TMP and DIP , 2004 .

[53]  P. Somasundaran,et al.  Dimerization of Oleate in Aqueous Solutions , 1984 .

[54]  K. L. Kalra,et al.  Fungal production of citric acid. , 1995, Biotechnology advances.

[55]  D. Vollhardt,et al.  Texture features of long-chain fatty acid monolayers at high pH of the aqueous subphase , 1999 .

[56]  Anders S Carlsson,et al.  High-value oils from plants. , 2008, The Plant journal : for cell and molecular biology.

[57]  A Fiechter,et al.  Pseudomonas aeruginosa biosurfactant production in continuous culture with glucose as carbon source , 1984, Applied and environmental microbiology.

[58]  M. Michel,et al.  Mixed micelles as delivery systems for enhanced emulsifier adsorption at the air/water interface : Sodium stearoyl lactylate (SSL)/Tween80 solutions , 2007 .

[59]  E. Niki,et al.  Action of Fatty Acid Esters of L-Ascorbic Acid as Antioxidants in Phosphatidylcholine Liposomal Membranes , 1992 .

[60]  J. Szymanowski,et al.  Comparison of Composition and Properties of Ethoxylated Dodecanoic acid obtained in the Presence of Various Catalysts , 2004 .

[61]  Mitsutoshi Nakajima,et al.  The effect of the hydrophobicity of microchannels and components in water and oil phases on droplet formation in microchannel water-in-oil emulsification , 2001 .

[62]  T. Balasubramanian,et al.  Production and characterization of a glycolipid biosurfactant from Bacillus megaterium using economically cheaper sources , 2008 .

[63]  O. Winter,et al.  Make Ethylene from Ethanol. , 1977 .

[64]  A. O'lenick,et al.  The effect of branching and unsaturation upon some properties of polyoxyethylene glycol diesters , 1998 .

[65]  A. Pinazo,et al.  Non-conventional surfactants from amino acids and glycolipids: Structure, preparation and properties , 1997 .

[66]  B. Ninham,et al.  Nanotubes from a vitamin C-based bolaamphiphile. , 2006, Journal of the American Chemical Society.

[67]  A. Sundberg,et al.  Recovery of water-soluble acetylgalactoglucomannans from mechanical pulp of spruce , 2003 .

[68]  T. Nakahara,et al.  Bioconversion of Maleic Acid to Fumaric Acid by Pseudomonas alcaligenes Strain XD-1 , 1997 .

[69]  Masahiro Takehara Properties and applications of amino acid based surfactants , 1989 .

[70]  L. Harvey,et al.  The Genus Gluconobacter and Its Applications in Biotechnology , 2001, Critical reviews in biotechnology.

[71]  I. Chronakis,et al.  Complex formation in aqueous medium of partially hydrolysed oat cereal proteins with sodium stearoyl-2 lactylate (SSL) lipid surfactant and implications for bile acids activity. , 2004, Colloids and surfaces. B, Biointerfaces.

[72]  M. Matsufuji,et al.  High production of rhamnolipids by Pseudomonas aeruginosagrowing on ethanol , 1997, Biotechnology Letters.

[73]  Jih‐Gaw Lin,et al.  Enhancement of anaerobic digestion of waste activated sludge by alkaline solubilization , 1997 .

[74]  E. Campos,et al.  Biodegradability and ecotoxicity of amine oxide based surfactants. , 2007, Chemosphere.

[75]  K. Hanabusa,et al.  l-Lysine-based supramolecular hydrogels containing various inorganic ions. , 2005, Organic & biomolecular chemistry.

[76]  Charles A. Pittinger,et al.  Environmental life-cycle inventory of detergent-grade surfactant sourcing and production , 1993 .

[77]  S. George,et al.  Analysis of Rhamnolipid Biosurfactants Produced Through Submerged Fermentation Using Orange Fruit Peelings as Sole Carbon Source , 2009, Applied biochemistry and biotechnology.

[78]  H. Miyafuji,et al.  Lignocellulose Feedstocks for the Production of Lactic Acid , 2004 .

[79]  B. Trathnigg,et al.  Direct ethoxylation of a longer-chain aliphatic ester , 2001 .

[80]  K. Hanabusa,et al.  Novel dumbbell-form low-molecular-weight gelators based on L-lysine: their hydrogelation and organogelation properties , 2005 .

[81]  M. Basri,et al.  Optimization of the enzyme-catalyzed synthesis of amino acid-based surfactants from palm oil fractions. , 2003, Journal of bioscience and bioengineering.

[82]  Y. Asano,et al.  Enzymatic chemoselective synthesis of secondary-amide surfactant from N-methylethanol amine. , 2005, Journal of bioscience and bioengineering.

[83]  S. Lee,et al.  Production of succinic acid by bacterial fermentation , 2006 .

[84]  Deepika,et al.  Sulfosuccinates as Mild Surfactants , 2006 .

[85]  Chunlin Xu,et al.  Mannans as stabilizers of oil-in-water beverage emulsions. , 2009 .

[86]  A. Tikhonov,et al.  Molecular ordering and phase behavior of surfactants at water-oil interfaces as probed by X-ray surface scattering. , 2008, Annual review of physical chemistry.

[87]  A G Vlyssides,et al.  Thermal-alkaline solubilization of waste activated sludge as a pre-treatment stage for anaerobic digestion. , 2004, Bioresource technology.

[88]  Anne-Sophie Duwez Exploiting electron spectroscopies to probe the structure and organization of self-assembled monolayers: a review , 2004 .

[89]  P. Adlercreutz,et al.  Enzymatic Synthesis of Hexyl Glycosides from Lactose At Low Water Activity and High Temperature Using Hyperthermostable β-glycosidases , 2002 .

[90]  M. F. Cox,et al.  Impact of molecular structure on the performance of methyl ester ethoxylates , 1998 .

[91]  Michael Edidin,et al.  Lipids on the frontier: a century of cell-membrane bilayers , 2003, Nature Reviews Molecular Cell Biology.

[92]  M. Infante,et al.  Enzymatic synthesis and physicochemical characterization of glycero arginine-based surfactants , 2004 .

[93]  G. Pastore,et al.  Production and properties of a surfactant obtained from Bacillus subtilis grown on cassava wastewater. , 2006, Bioresource technology.

[94]  H. Isoda,et al.  Functions and potential applications of glycolipid biosurfactants--from energy-saving materials to gene delivery carriers. , 2002, Journal of bioscience and bioengineering.

[95]  Y. Peleg,et al.  Optimization of L‐malic acid production by Aspergillus flavus in a stirred fermentor , 1991, Biotechnology and bioengineering.

[96]  D. Riesner,et al.  Prion decontamination during the oleochemical process of fat hydrogenation , 2008 .

[97]  D. Shah,et al.  Cooperativity among Molecules at Interfaces in Relation to Various Technological Processes: Effect of Chain Length on the pKa of Fatty Acid Salt Solutions† , 2000 .

[98]  Rathin Datta,et al.  Lactic acid: recent advances in products, processes and technologies — a review , 2006 .

[99]  R. P. John,et al.  Fermentative production of lactic acid from biomass: an overview on process developments and future perspectives , 2007, Applied Microbiology and Biotechnology.

[100]  R. Spaccini,et al.  Soil remediation: humic acids as natural surfactants in the washings of highly contaminated soils. , 2005, Environmental pollution.

[101]  P. Adlercreutz,et al.  Preparation of lipases for use in organic solvents , 2002 .

[102]  Pernilla Turner,et al.  A novel variant of Thermotoga neapolitana beta-glucosidase B is an efficient catalyst for the synthesis of alkyl glucosides by transglycosylation. , 2007, Journal of biotechnology.

[103]  M. Infante,et al.  Preliminary studies of the toxic effects of non-ionic surfactants derived from lysine. , 1996, Toxicology.

[104]  Sang Hyun Lee,et al.  Ultrasound-enhanced lipase activity in the synthesis of sugar ester using ionic liquids , 2008 .

[105]  Jiumn-Yih Wu,et al.  Microbial synthesis of cis,cis-muconic acid by Sphingobacterium sp GCG generated from effluent of a styrene monomer (SM) production plant , 2004 .

[106]  M. F. Cox,et al.  Methyl ester ethoxylates , 1997 .

[107]  K. Hanabusa,et al.  New Low‐Molecular‐Mass Gelators Based on L‐Lysine: Amphiphilic Gelators and Water‐Soluble Organogelators , 2004 .

[108]  E. Vulfson,et al.  Chemo-enzymatic synthesis of amino acid-based surfactants , 1997 .

[109]  K. Danov,et al.  Effect of the precipitation of neutral-soap, acid-soap, and alkanoic acid crystallites on the bulk pH and surface tension of soap solutions. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[110]  L. Shrestha,et al.  Aqueous foam stabilized by dispersed surfactant solid and lamellar liquid crystalline phase. , 2006, Journal of colloid and interface science.

[111]  Akio Ohta,et al.  Effect of the side chain of N-acyl amino acid surfactants on micelle formation: An isothermal titration calorimetry study , 2008 .

[112]  Sang Yup Lee,et al.  Batch and continuous fermentation of succinic acid from wood hydrolysate by Mannheimia succiniciproducens MBEL55E , 2004 .

[113]  L. Shrestha,et al.  Aqueous Phase Behavior of Diglycerol Fatty Acid Esters , 2007 .

[114]  Kulkarni,et al.  Mixtures of Ascorbyl-stearate and Vitamin D3: A Monolayer Study at the Gas/Water Interface , 1997, Journal of colloid and interface science.

[115]  S. Palma,et al.  Evaluation of the surfactant properties of ascorbyl palmitate sodium salt. , 2002, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[116]  M. C. Feiters,et al.  Gemini surfactants: new synthetic vectors for gene transfection. , 2003, Angewandte Chemie.

[117]  W. Hreczuch,et al.  Rapeseed Methyl Ester Ethoxylates: A New Class of Surfactants of Environmental and Commercial Interest , 2005 .

[118]  S. Adachi,et al.  Equilibrium yield of n-alkyl-β-D-glucoside through condensation of glucose and n-alcohol by β-glucosidase in a biphasic system , 1995 .

[119]  P. Brogueira,et al.  Microdomains in mixed monolayers of oleanolic and stearic acids: thermodynamic study and BAM observation at the air-water interface and AFM and FTIR analysis of LB monolayers. , 2007, Chemistry and physics of lipids.

[120]  D. Seebach,et al.  pH‐Sensitive Vesicles Containing a Lipidic β‐Amino Acid with Two Hydrophobic Chains , 2008, Chemistry & biodiversity.

[121]  D. Sabatini,et al.  Rhamnolipid biosurfactant mixtures for environmental remediation. , 2008, Water research.

[122]  S. Palma,et al.  Solubilization of hydrophobic drugs in octanoyl-6-O-ascorbic acid micellar dispersions. , 2002, Journal of pharmaceutical sciences.

[123]  A. Jensen,et al.  Production of heat-sensitive monoacylglycerols by enzymatic glycerolysis in tert-pentanol: Process optimization by response surface methodology , 2006 .

[124]  P. Monsan,et al.  Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo-cosmetic applications. , 1999, Biotechnology and bioengineering.

[125]  J. Contiero,et al.  Rhamnolipid production by Pseudomonas aeruginosa LBI growing on soapstock as the sole carbon source , 2002 .

[126]  J. Stefan Rokem,et al.  Organic acids: old metabolites, new themes , 2006 .

[127]  H. Hensen,et al.  Comparative studies on the ocular and dermal irritation potential of surfactants. , 2007, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[128]  F. Fava,et al.  Soya lecithin effects on the aerobic biodegradation of polychlorinated biphenyls in an artificially contaminated soil. , 2001, Biotechnology and bioengineering.

[129]  Karlheinz Hill,et al.  Alkyl Polyglycosides-Properties and Applications of a new Class of Surfactants. , 1998, Angewandte Chemie.

[130]  J. Baeyens,et al.  Reducing the Heavy Metal Content of Sewage Sludge by Advanced Sludge Treatment Methods , 2006 .

[131]  Soon Ho Hong,et al.  Biological conversion of wood hydrolysate to succinic acid by Anaerobiospirillum succiniciproducens , 2004, Biotechnology Letters.

[132]  Jiang Yang Viscoelastic wormlike micelles and their applications , 2002 .

[133]  M. C. Feiters,et al.  Cationic gemini Surfactants based on tartaric acid: Synthesis, aggregation, monolayer behaviour, and interaction with DNA , 2002 .

[134]  A. Janssen,et al.  Enzymatic synthesis of carbohydrate esters in 2-pyrrolidone. , 1991 .

[135]  Pär Tufvesson,et al.  Solvent‐free enzymatic synthesis of fatty alkanolamides , 2007, Biotechnology and bioengineering.

[136]  Y. Y. Lee,et al.  High-yield fermentation of pentoses into lactic acid , 2000, Applied biochemistry and biotechnology.

[137]  A. Klibanov,et al.  Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide , 1988 .

[138]  J. Szymanowski,et al.  Catalysts for Oxyethylation of Alcohols and Fatty Acid Methyl Esters , 2004 .

[139]  C. Boettcher,et al.  Molecular monolayer rods and tubules made of .alpha.-(L-lysine),.omega.-(amino) bolaamphiphiles , 1993 .

[140]  E. Vulfson,et al.  Application of enzymes to the synthesis of amino acid-based bola and gemini surfactants , 1998 .

[141]  B. Novalès,et al.  Self-assembly of fatty acids and hydroxyl derivative salts. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[142]  M. Infante,et al.  Chemo-enzymatic synthesis of arginine-based gemini surfactants. , 2000, Biotechnology and bioengineering.

[143]  Richard P. Vlosky,et al.  Past, Present, and Future of the Wood Preservation Industry , 2003 .

[144]  J. Kohlbrecher,et al.  Microstructure and stability of a lamellar liquid crystalline and gel phase formed by a polyglycerol ester mixture in dilute aqueous solution. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[145]  P. Gorin,et al.  HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE , 1961 .

[146]  Sumita Roy,et al.  Self-Organization Properties and Microstructures of Sodium N-(11-Acrylamidoundecanoyl)-L-valinate and -L-threoninate in Water , 2006 .

[147]  M. Girardin,et al.  Enzymatic synthesis of fatty acid ascorbyl esters , 1998 .

[148]  S. Adachi,et al.  Lipase-catalyzed synthesis of O-lauroyl l-serinamide and O-lauroyl l-threoninamide , 2005 .

[149]  Huai N. Cheng,et al.  Soybean oil as a renewable feedstock for nitrogen-containing derivatives , 2008 .

[150]  M. A. Eiteman,et al.  Effects of Growth Mode and Pyruvate Carboxylase on Succinic Acid Production by Metabolically Engineered Strains of Escherichia coli , 2002, Applied and Environmental Microbiology.

[151]  Naoual Anoune,et al.  Synthesis and characterization of new cationic surfactants derived from lactic acid , 2000 .

[152]  S. Féry-Forgues,et al.  Self-assembly properties of some chiral N-palmitoyl amino acid surfactants in aqueous solution. , 2008, Journal of colloid and interface science.

[153]  Andreas Schmid,et al.  The production of fine chemicals by biotransformations. , 2002, Current opinion in biotechnology.

[154]  M. Infante,et al.  Synthesis of glycero amino acid-based surfactants. Part 1. Enzymatic preparation of rac-1-O-(Nα-acetyl-L-aminoacyl)glycerol derivatives , 2001 .

[155]  B. Holmbom,et al.  Stabilization of wood-resin emulsions by dissolved galactoglucomannans and galactomannans , 2004 .

[156]  B. C. Guha,et al.  Biosynthesis of Ascorbic Acid , 1936, Nature.

[157]  R. Seviour,et al.  Growth of Filamentous Fungi in Submerged Culture: Problems and Possible Solutions , 2000, Critical reviews in biotechnology.

[158]  S. Morel,et al.  Glucosylation of α-butyl- and α-octyl-d-glucopyranosides by dextransucrase and alternansucrase from Leuconostoc mesenteroides , 2003 .

[159]  J. Ortega-Calvo,et al.  Bioavailability of solid and non-aqueous phase liquid (NAPL)-dissolved phenanthrene to the biosurfactant-producing bacterium Pseudomonas aeruginosa 19SJ. , 2001, Environmental microbiology.

[160]  A. Antipova,et al.  Thermodynamic and functional properties of legumin (11S globulin from Vicia faba) in the presence of small-molecule surfactants: effect of temperature and pH. , 2004, Journal of colloid and interface science.

[161]  B. Folmer Sterol surfactants: from synthesis to applications. , 2003, Advances in colloid and interface science.

[162]  J. O. Metzger,et al.  Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification , 2006, Applied Microbiology and Biotechnology.

[163]  Asha A. Juwarkar,et al.  Distillery and curd whey wastes as viable alternative sources for biosurfactant production , 2001 .

[164]  T. Tryfona,et al.  Fermentative production of lysine by Corynebacterium glutamicum : transmembrane transport and metabolic flux analysis , 2005 .

[165]  S. Lang,et al.  Rhamnose lipids – biosynthesis, microbial production and application potential , 1999, Applied Microbiology and Biotechnology.

[166]  P. Halling,et al.  Organic solvent functional group effect on enzyme inactivation by the interfacial mechanism , 2000 .

[167]  Pradip K. Roychoudhury,et al.  L (+) lactic acid fermentation and its product polymerization , 2004 .

[168]  V. Tyagi,et al.  Fatty Imidazolines: Chemistry, Synthesis, Properties and Their Industrial Applications , 2006 .

[169]  Rafael Luque,et al.  Towards a bio-based industry: benign catalytic esterifications of succinic acid in the presence of water. , 2007, Chemistry.

[170]  J. Borchardt The use of surfactants in de-inking paper for paper recycling , 1997 .

[171]  M. Navia,et al.  Cross-linked enzyme crystals as robust biocatalysts , 1992 .

[172]  Marin Berovic,et al.  Citric acid production. , 2007, Biotechnology annual review.

[173]  A. Fiechter Biosurfactants: moving towards industrial application. , 1992, Trends in biotechnology.

[174]  A. O'lenick Evaluation of polyoxyethylene glycol esters of castor, high-erucic acid rapeseed, and soybean oils , 2000 .

[175]  Sang Yup Lee,et al.  The genome sequence of the capnophilic rumen bacterium Mannheimia succiniciproducens , 2004, Nature Biotechnology.

[176]  J. Kukkonen,et al.  Fate of wood extractives in wastewater treatment plants at kraft pulp mills and mechanical pulp mills. , 2004, Water research.

[177]  E. Vulfson,et al.  Application of enzymes to the synthesis of surfactants. , 1995, Trends in biotechnology.

[178]  Karlheinz Hill,et al.  Industrial development and application of biobased oleochemicals , 2007 .

[179]  M. Basri,et al.  Response surface methodological study on lipase-catalyzed synthesis of amino acid surfactants , 2004 .

[180]  W. Friedt,et al.  New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry. , 2000, Angewandte Chemie.

[181]  P. Adlercreutz,et al.  alpha-Amylase-catalysed synthesis of alkyl glycosides , 2005 .

[182]  Y. Peleg,et al.  Malic acid accumulation by Aspergillus flavus , 1989, Applied Microbiology and Biotechnology.

[183]  Rosário Oliveira,et al.  Biosurfactants: potential applications in medicine. , 2006, The Journal of antimicrobial chemotherapy.

[184]  G. T. Tsao,et al.  Mycelial pellet formation by Rhizopus oryzae ATCC 20344 , 2000 .

[185]  E. Gilbert The Reactions of Sulfur Trioxide, and Its Adducts, with Organic Compounds. , 1962 .

[186]  K. Hanabusa,et al.  Supramolecular Gels Formed by Amphiphilic Low‐Molecular‐Weight Gelators of Nα,Nε‐Diacyl‐L‐Lysine Derivatives , 2008 .

[187]  George Italo Pitombeira Nunes,et al.  Review on Anionic/Cationic Surfactant Mixtures , 2008 .

[188]  Johnathan E. Holladay,et al.  Top Value Added Chemicals From Biomass. Volume 1 - Results of Screening for Potential Candidates From Sugars and Synthesis Gas , 2004 .

[189]  J. Johansson,et al.  Polymyxin B/Pulmonary Surfactant Mixtures Have Increased Resistance to Inactivation by Meconium and Reduce Growth of Gram-Negative Bacteria In Vitro , 2006, Pediatric Research.

[190]  P. Halling,et al.  Immiscible organic solvent inactivation of urease, chymotrypsin, lipase, and ribonuclease: Separation of dissolved solvent and interfacial effects , 1994, Biotechnology and bioengineering.

[191]  J. V. Gerpen,et al.  Biodiesel processing and production , 2005 .

[192]  A. Klibanov Improving enzymes by using them in organic solvents , 2001, Nature.

[193]  Fengbao Zhang,et al.  Comparison of four catalysts in the catalytic dehydration of ethanol to ethylene , 2008 .

[194]  S. Cameotra,et al.  Recent applications of biosurfactants as biological and immunological molecules. , 2004, Current opinion in microbiology.

[195]  B. Mattiasson,et al.  Synthesis of alkylgalactosides using whole cells of Bacillus pseudofirmus species as catalysts. , 2004, Journal of biotechnology.

[196]  J. Chaudhuri,et al.  Biocatalysis in organic media using enzymes from extremophiles , 1999 .

[197]  U. Bornscheuer,et al.  Lipase-Catalyzed Solid Phase Synthesis of Sugar Fatty Acid Esters , 1996 .

[198]  M. Lupo Antioxidants and vitamins in cosmetics. , 2001, Clinics in dermatology.

[199]  Hylke B. Akkerman,et al.  Towards molecular electronics with large-area molecular junctions , 2006, Nature.

[200]  M. Reetz,et al.  Superior Biocatalysts by Directed Evolution , 1999 .

[201]  J. R. Frank,et al.  Technological and economic potential of poly(lactic acid) and lactic acid derivatives , 1995 .

[202]  T. Watanabe,et al.  Citric acid production from xylan and xylan hydrolysate by semi-solid culture of Aspergillus niger. , 1999, Bioscience, biotechnology, and biochemistry.

[203]  H. Sasamoto,et al.  Effects of ethoxylate structure on surfactant properties of ethoxylated fatty methyl esters , 1997 .

[204]  D. Shah,et al.  Effect of Premicellar Aggregation on the pKa of Fatty Acid Soap Solutions , 2003 .

[205]  C. Selve,et al.  Nonionic amphiphilic compounds from lysine as molecular mimics of lecithins , 1996 .

[206]  S. Adachi,et al.  β-Glucosidase-catalyzed condensation of glucose with 2-alcohols in buffer-saturated alcohols , 1997, Biotechnology Letters.

[207]  George John,et al.  Crops: a green approach toward self-assembled soft materials. , 2008, Accounts of chemical research.

[208]  Joseph M. Perez,et al.  Soybean Oil-Based Lubricants: A Search for Synergistic Antioxidants† , 2007 .

[209]  Henrikke Baumann,et al.  The hitch hiker's guide to LCA : an orientation in life cycle assessment methodology and application , 2004 .

[210]  M. Rossi,et al.  Oligosaccharide synthesis by glycosynthases. , 2004, Trends in biotechnology.

[211]  Fulvia Tambone,et al.  Use of biosurfactants from urban wastes compost in textile dyeing and soil remediation. , 2009, Waste management.

[212]  O. Ward,et al.  Lipase-catalyzed synthesis of a sugar ester containing arachidonic acid , 1997 .

[213]  V. Tyagi,et al.  Microbial Surfactants: A Review , 2006 .

[214]  Érica Regina Daiuto,et al.  Effects of Extraction Methods on Yam (Dioscorea alata) Starch Characteristics , 2005 .

[215]  Keith J. Watson,et al.  HOW MIGHT BIOFUELS IMPACT THE CHEMICAL INDUSTRY , 2008 .

[216]  C. Otero,et al.  Enzymatic synthesis of amide surfactants from ethanolamine. , 2001, Enzyme and microbial technology.

[217]  E. Coutouli-argyropoulou,et al.  Synthesis and characterization of nonconventional surfactants of aromatic amino acid-glycerol ethers: effect of the amino acid moiety on the orientation and surface properties of these soap-type amphiphiles. , 2006, Chemistry.

[218]  M. Nydén,et al.  Structure and dynamics of micelles and cubic phase structures with ethoxylated phytosterol surfactant in water. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[219]  L. Pérez,et al.  Cationic surfactants from lysine: synthesis, micellization and biological evaluation. , 2009, European journal of medicinal chemistry.

[220]  P. Adlercreutz,et al.  Enhanced transglucosylation/hydrolysis ratio of mutants of Pyrococcus furiosus beta-glucosidase: effects of donor concentration, water content, and temperature on activity and selectivity in hexanol. , 2001, Biotechnology and bioengineering.

[221]  D. G. Allen,et al.  Alkaline extraction of wastewater activated sludge biosolids. , 2010, Bioresource technology.

[222]  Anders Strand,et al.  Phase Distribution of Resin and Fatty Acids in Colloidal Wood Pitch Emulsions at Different pH-Levels , 2009 .

[223]  R. Miller,et al.  Enhanced octadecane dispersion and biodegradation by a Pseudomonas rhamnolipid surfactant (biosurfactant) , 1992, Applied and environmental microbiology.

[224]  M. Ferrer,et al.  Effect of the Immobilization Method of Lipase from Thermomyces lanuginosus on Sucrose Acylation , 2002 .

[225]  R. Darton,et al.  Continuous production of biosurfactant with foam fractionation , 2006 .

[226]  Yala Zhang,et al.  Kinetic ESR study on the reaction of vitamin E radical with vitamin C and its lipophilic derivatives in cetyltrimethylammonium bromide micelles , 1992 .

[227]  P. Bahadur,et al.  A comparative study on the surface activity and micellar behaviour of some N-acylamino acid based surfactants , 1998 .

[228]  S. Anastassiadis,et al.  Citric acid production patent review. , 2008, Recent patents on biotechnology.

[229]  W. Rosenblatt,et al.  Micro-emulsion process for the preparation of sucrose esters , 1967 .

[230]  V. Spitzer Screening analysis of unknown seed oils , 1999 .

[231]  R. Sheldon,et al.  Glycosidase-catalysed synthesis of alkyl glycosides , 1999 .

[232]  B. Szuhaj,et al.  High-performance liquid chromatographic separations of soy phospholipids , 1996 .

[233]  A. Straathof,et al.  Fumaric acid production by fermentation , 2008, Applied Microbiology and Biotechnology.

[234]  William A. Weigand,et al.  Economic comparison of calcium fumarate and sodium fumarate production byRhizopus arrhizus , 1990 .

[235]  C. Otero,et al.  Selective enzymatic synthesis of amide surfactants from diethanolamine , 2003 .

[236]  D. G. Allen,et al.  Surfactant-like Properties of Alkaline Extracts from Wastewater Biosolids , 2010 .

[237]  M. Infante,et al.  Biological properties of arginine-based glycerolipidic cationic surfactants , 2005 .

[238]  K. Berglund,et al.  Effect of Different Carbon Sources on the Production of Succinic Acid Using Metabolically Engineered Escherichia coli , 2007, Biotechnology progress.

[239]  Y. Wee,et al.  Biotechnological Production of Lactic Acid and Its Recent Applications , 2006 .

[240]  S. Nishimura,et al.  Carbohydrate analysis by a phenol-sulfuric acid method in microplate format. , 2005, Analytical biochemistry.

[241]  K. Hanabusa,et al.  Novel family of low molecular weight hydrogelators based on L-lysine derivatives. , 2002, Chemical communications.

[242]  Phospholipid class and FA compositions of modified soybeans processed with two extraction methods , 2003 .

[243]  M. Infante,et al.  Synthesis, Aggregation, and Biological Properties of a New Class of Gemini Cationic Amphiphilic Compounds from Arginine, bis(Args)† , 1996 .

[244]  A. Romani,et al.  Self-assembling and antioxidant activity of some vitamin C derivatives , 2000 .

[245]  D. Boocock,et al.  Fuels and chemicals from sewage sludge , 1992 .

[246]  Pål Börjesson,et al.  Industrial biotechnology for the production of bio-based chemicals--a cradle-to-grave perspective. , 2007, Trends in biotechnology.

[247]  D. Cooper,et al.  Surface active properties of a biosurfactant fromCorynebacterium lepus , 1981 .

[248]  T. Müller,et al.  Ethoxylated rapeseed oil derivatives as non-ionic adjuvants for glyphosate. , 2007, Pest management science.

[249]  M. Flickinger,et al.  L-lysine production at 50 degrees C by mutants of a newly isolated and characterized methylotrophic Bacillus sp , 1990, Applied and environmental microbiology.

[250]  D. Riesner,et al.  Risk assessment for fat derivatives in case of contamination with BSE , 2006 .

[251]  Sang Hyun Lee,et al.  Lipase‐catalyzed synthesis of fatty acid sugar ester using extremely supersaturated sugar solution in ionic liquids , 2008, Biotechnology and bioengineering.

[252]  David P. Clark,et al.  Mutation of the ptsG Gene Results in Increased Production of Succinate in Fermentation of Glucose byEscherichia coli , 2001, Applied and Environmental Microbiology.

[253]  B. Dien,et al.  Fermentation of sugar mixtures using Escherichia coli catabolite repression mutants engineered for production of L-lactic acid , 2002, Journal of Industrial Microbiology and Biotechnology.

[254]  K. Holmberg Unsaturated monoethanolamide ethoxylates as paint surfactants , 1996 .

[255]  V. Vinci,et al.  Improvement of microbial strains and fermentation processes , 2000, Applied Microbiology and Biotechnology.

[256]  J. Gauvrit,et al.  Critical micelle concentrations of different classes of surfactants: A quantitative structure property relationship study , 2002 .

[257]  W. F. Libby,et al.  Age determinations by radiocarbon content; checks with samples of known age. , 1949, Science.

[258]  G. Gadd Fungal production of citric and oxalic acid: importance in metal speciation, physiology and biogeochemical processes. , 1999, Advances in microbial physiology.

[259]  Tae Yong Kim,et al.  Metabolic engineering of Escherichia coli for the production of malic acid , 2008 .

[260]  V. Wray,et al.  Enzymatic monoacylation of fructose by two procedures , 1995 .

[261]  S. Adachi,et al.  Enzymatic synthesis of N-acyl-l-amino acids in a glycerol-water system using acylase I from pig kidney , 2002 .

[262]  M. Leser,et al.  Interfacial and foaming properties of some food grade low molecular weight surfactants , 2008 .

[263]  Yonghua Wang,et al.  Insight into the Enzymatic Degumming Process of Soybean Oil , 2008 .

[264]  D. Konopacka-Łyskawa,et al.  The interactions of saturated fatty acids at the dodecane/water interface and their sodium salts at the air/water interface , 1999 .

[265]  M. Britten,et al.  Heat treatment of whey proteins in the presence of anionic surfactants , 2004 .

[266]  S. L. Fox,et al.  Production of surfactant from Bacillus subtilis ATCC 21332 using potato substrates , 2000 .

[267]  SYNTHESIS AND PROPERTIES OF ASYMMETRICAL NONIONIC DOUBLE CHAIN SURFACTANTS FROM LYSINE , 1999 .

[268]  J. Hemming,et al.  Phenolic and Lipophilic Extractives in Scots Pine Knots and Stemwood , 2003 .

[269]  Yu-Yen Linko,et al.  Fumaric acid production from xylose by immobilized Rhizopus arrhizus cells , 2004, Applied Microbiology and Biotechnology.