Structure, Stability and Crystal Growth of Polymorphs and Polytypes of Long-Chain Aliphatic Compounds

  • Kiyotaka Sato
  • Masamichi Kobayashi
Part of the Crystals book series (CRYSTALS, volume 13)

Abstract

This article reviews recent studies on crystal structure, thermodynamic stability and crystal growth of polymorphs and polytypes of long-chain aliphatic compounds. Particular attention is paid to the n-fatty acids, since numerous studies have recently been made on these compounds. Details of their molecular structures are described, based on X-ray crystallographic and vibrational spectroscopic data. Using stearic acid, an outstanding model substance, the thermodynamic stability of the different polymorphic as well as polytypic modifications is studied, by precisely measuring the solubility data of each modification (using single crystals). Calculations of molecular interactions combined with vibrational spectroscopic data are also used to evaluate the thermodynamic stability. A few examples of solid-state transformations, where polymorphic and polytypic conversions occur at the same time, are examined by electron microscopic and vibrational spectroscopic methods. The characteristics of nucleation probability and crystal growth rate of different polymorphs and polytypes from various organic solutions are subsequently described. It is found that, depending on the polymorph, the effects of temperature, supersaturation and solvents appear in a different manner. Finally thin film growth by vacuum deposition is studied by electron microscopic observation and analyzed with respect to the importance of the molecular orientation and the underlying vapor growth mechanisms.

Keywords

Entropy Surfactant Crystallization Enthalpy Hydrocarbon 

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References

  1. 1.
    Verma AR, Krishna P (1966) Polymorphism and polytypism in crystals, Wiley, New YorkGoogle Scholar
  2. 2.
    Boistelle R (1980) Defect structures and growth mechanisms of long-chain alkanes, in: Current Topics in Materials Sciences, Kaldis E (ed.), North Holland Publ. Co, Amsterdam, 413Google Scholar
  3. 3.
    Vand V (1951) Acta Cryst. 4: 104CrossRefGoogle Scholar
  4. 4.
    Abrahamsson S, Dahlen B, Lofgren H, Pascher H (1978) Prog Chem Fats Other Lipids 16: 125CrossRefGoogle Scholar
  5. 5.
    Hernqvist L (1988) Crystal structures of fats and fatty acids, in: Crystallization and polymorphism of fats and fatty Acids, Garti N, Sato K (eds), Marcel Dekker Inc, New York p 97Google Scholar
  6. 6.
    Nyberg SC, Luth H (1972) Acta Cryst B28: 2992Google Scholar
  7. 7.
    Nyberg SC, Porworowski JA (1973) Acta Cryst B29: 347Google Scholar
  8. 8.
    Goto M, Asada E (1978) Bull Chem Soc Japan 51: 70CrossRefGoogle Scholar
  9. 9.
    Lomer TR (1963) Acta Cryst 16: 984CrossRefGoogle Scholar
  10. 10.
    Goto M, Asada E (1980) Bull Chem Soc Japan 53: 2111CrossRefGoogle Scholar
  11. 11.
    Teare HMM (1959) Acta Cryst 12: 294CrossRefGoogle Scholar
  12. 12.
    Shearer HMM, Vand V (1956) Acta Cryst 9: 379CrossRefGoogle Scholar
  13. 13.
    Pieszek W, Strobl CR, Malzahn K (1974) Acta Crystallogr B30: 1278Google Scholar
  14. 14.
    Goto M, Asada E (1978) Bull Chem Soc Japan 51: 2456CrossRefGoogle Scholar
  15. 15.
    Malta V, Cellotti G, Zannetti R, Martelli AF (1971) J Chem Soc (B), 548Google Scholar
  16. 16.
    Goto M, Asada E (1984) Bull Chem Soc Japan 57: 1145CrossRefGoogle Scholar
  17. 17.
    Abrahamsson S, Larsson K, von Sydow E (1960) Acta Cryst 13: 770CrossRefGoogle Scholar
  18. 18.
    Schaerer AA, Busso CJ, Smith AE, Skinner LB (1955) J Am Chem Soc 77: 2017CrossRefGoogle Scholar
  19. 19.
    Kobayashi M, Kobayashi T, Tadokoro H (1984) Mol Cryst Liq Cryst 104: 193CrossRefGoogle Scholar
  20. 20.
    von Sydow E (1955) Acta Cryst 8: 845CrossRefGoogle Scholar
  21. 21.
    von Sydow E (1956) Acta Chem Scand 10, 1CrossRefGoogle Scholar
  22. 22.
    Lutton ES (1967) in Fatty Acids, 2nd Edition, Part 4, Markeley KS (eds), John Wiley & Sons Inc., New York, 2583Google Scholar
  23. 23.
    Vand V, Morley WH, Lomer TR (1951) Acta Cryst 4: 324CrossRefGoogle Scholar
  24. 24.
    von Sydow E (1955) Acta Cryst 8: 557CrossRefGoogle Scholar
  25. 25.
    Larsson K, von Sydow E (1966) Acta Chem Scand 20: 1203CrossRefGoogle Scholar
  26. 26.
    Holland RF, Nielsen JR (1962) J Mol Spectrose 9: 436CrossRefGoogle Scholar
  27. 27.
    Holland RF, Nielsen JR (1963) Acta Cryst 16: 902CrossRefGoogle Scholar
  28. 28.
    Kobayashi M (1985) J Mol Struct 16: 193CrossRefGoogle Scholar
  29. 29.
    von Sydow E (1955) Acta Cryst 8: 810CrossRefGoogle Scholar
  30. 30.
    Boistelle R, Simon B, Pepe G (1976) Acta Cryst B32: 1240Google Scholar
  31. 31.
    Kobayashi M, Sakagami K, Tadokoro H (1983) J Chem Phys 78: 6391CrossRefGoogle Scholar
  32. 32.
    Kobayashi M, Kobayashi T, Itoh Y, Sato K (1984) J Chem Phys 80: 2897CrossRefGoogle Scholar
  33. 33.
    Aquilano D (1977) J Crystal Growth 37: 215CrossRefGoogle Scholar
  34. 34.
    Rinaudo C, Aquilano D, Abbona F (1981) J Crystal Growth 53: 361CrossRefGoogle Scholar
  35. 35.
    Tasumi M, Shimanouchi T, Miyazawa T (1962) (1963) J Mol Spectrosc 9: 261; 11: 422CrossRefGoogle Scholar
  36. 36.
    Tasumi M, Shimanouchi T (1965) J Chem Phys 43: 1245CrossRefGoogle Scholar
  37. 37.
    Tasumi M, Krimm S (1967) J Chem Phys 46: 755CrossRefGoogle Scholar
  38. 38.
    Kitagawa T, Miyazawa T (1972) Adv Polym Sci 9: 335CrossRefGoogle Scholar
  39. 39.
    Snyder RG, Schachtschreider JH (1963) Spectrochim Acta 19: 85CrossRefGoogle Scholar
  40. 40.
    Schachtschreider JH, Snyder PG (1963) Spectrochim Acta 19: 117CrossRefGoogle Scholar
  41. 41.
    Koyama Y, Ikeda K (1980) Chem Phys Lipids 26: 149CrossRefGoogle Scholar
  42. 42.
    Kobayashi M, Kaneko F, Sato K, Suzuki M (1986) J Phys Chem 90: 6371CrossRefGoogle Scholar
  43. 43.
    Hayashi S, Umemura J (1975) J Chem Phys 63: 1732CrossRefGoogle Scholar
  44. 44.
    Umemura J (1978) J Chem Phys 68: 42CrossRefGoogle Scholar
  45. 45.
    Snyder RG (1979) J Chem Phys 71: 3329Google Scholar
  46. 46.
    Carter VB (1970) J Mol Spectrosc 34: 356CrossRefGoogle Scholar
  47. 47.
    Kobayashi M, Tadokoro H, Porter RS (1980) J Chem Phys 73: 3635CrossRefGoogle Scholar
  48. 48.
    Kobayashi M, Kobayashi T, Tadokoro H, Cho Y, Kaneko F (1986) Makromol Chem Macromol Symp 5, 1CrossRefGoogle Scholar
  49. 49.
    Ewen B, Fisher EW, Piesczek W, Strobl G (1974) J Chem Phys 61: 5265CrossRefGoogle Scholar
  50. 50.
    Kobayashi M, Kobayashi T, Itoh Y, Chatani Y, Tadokoro H (1980) J Chem Phys 72: 2024CrossRefGoogle Scholar
  51. 51.
    Kobayashi M, Kobayashi T, Itoh Y, Sato K (1986) Bull Mineral 109: 171Google Scholar
  52. 52.
    Beckman W, Boistell R, Sato K (1984) J Chem Eng Data 29: 215CrossRefGoogle Scholar
  53. 53.
    Sato K, Suzuki K, Okada M, Garti N (1985) J Crystal Growth 72: 699CrossRefGoogle Scholar
  54. 54.
    Sato K, Boistelle R (1983) J Colloid Interface Sci 94: 593CrossRefGoogle Scholar
  55. 55.
    Sato K, Boistelle R (1984) J Crystal Growth 66: 441CrossRefGoogle Scholar
  56. 56.
    von Sydow E (1955) Arkiv Kemi 9: 231Google Scholar
  57. 57.
    Garti N, Wellner E, Sarig S (1980) Krist Techn 15: 1303CrossRefGoogle Scholar
  58. 58.
    Wellner E, Garti N, Sarig S (1983) Cryst Res Techn 16: 1283Google Scholar
  59. 59.
    Bailey AV, Mitcham D, Pittman RA, Sumrell G (1972) J Am Oil Chem Soc 49: 419CrossRefGoogle Scholar
  60. 60.
    Sato K (unpublished data)Google Scholar
  61. 61.
    Morishita H, Ishioka T, Kobayashi M, Sato K (1987) J Phys Chem 91: 2273CrossRefGoogle Scholar
  62. 62.
    Sato K, Kobayashi M, Morishita H (1988) J Crystal Growth 87: 236CrossRefGoogle Scholar
  63. 63.
    Baronnet A (1978) Prog Crystal Growth Charact 1: 151CrossRefGoogle Scholar
  64. 64.
    Small DM (1986) Physical chemistry of lipids, in the series: Handbook of Lipid Research, vol 4, Hanahan DJ (ed) Plenum, New York, Chap. 7Google Scholar
  65. 65.
    Garti N, Wellner E, Sarig S (1980) Thermochim Acta 37: 131CrossRefGoogle Scholar
  66. 66.
    Kobayashi M (unpublished data)Google Scholar
  67. 67.
    Morishita H, Kobayashi M, Suzuki M, Sato K (1987) In Collected Abstracts of 54th Annual Meeting of Chem Soc Japan, Tokyo 402Google Scholar
  68. 68.
    Inaoka K, Kobayashi, Okada M, Sato K (1988) J Crystal Growth 87: 243CrossRefGoogle Scholar
  69. 69.
    Sato K (1979) Japan J Appl Phys 18: 1019CrossRefGoogle Scholar
  70. 70.
    Verma AR (1955) Proc Roy Soc A228: 34Google Scholar
  71. 71.
    Amelinckx S (1956) Acta Cryst 9: 16CrossRefGoogle Scholar
  72. 72.
    Kaneko F, Kobayashi M, Kitagawa Y, Matsuura Y (1988) Proc. ISA-JOCS Congress, vol. 1: 536Google Scholar
  73. 73.
    Walton G (1969) in Nucleation Zettlemeyer AC (ed), New York, Dekker 225Google Scholar
  74. 74.
    Beckmann W, Boistelle R (1984) J Crystal Growth 67: 271CrossRefGoogle Scholar
  75. 75.
    Beckmann W, Rouquerol R, Beckmann H (1983) Thermochim Acta 66: 295CrossRefGoogle Scholar
  76. 76.
    Cardew PT, Davey RJ (1982) Proceeding of a Symposium on “Tailoring of Crystal Growth”, Manchester, Inst Chem Eng, 1.1Google Scholar
  77. 77.
    Davey RJ, Richards J (1985) J Crystal Growth 71: 597CrossRefGoogle Scholar
  78. 78.
    Sato K, Okada M (1972) J Crystal Growth 42: 259CrossRefGoogle Scholar
  79. 79.
    Cardew PT, Davey RJ (1985) Proc Roy Soc London A398: 415Google Scholar
  80. 80.
    Sato K (1989) in: Morphology and Growth Units of Crystals, Sunagawa I (ed), Terra Pub Co Tokyo, 513.Google Scholar
  81. 81.
    Murata Y, Motomura K, Matsuura R (1978) Mem Fac Sci Kyushu Univ Ser C 11: 29Google Scholar
  82. 82.
    Garti N, Sato K, Schlichter J, Wellner E (1986) Cryst Res Techn 20: 653CrossRefGoogle Scholar
  83. 83.
    Beckmann W, Boistelle R (1985) J Crystal Growth 72: 621CrossRefGoogle Scholar
  84. 84.
    Garti N, Sato K (1986) J Am Oil Chem Soc 63: 236CrossRefGoogle Scholar
  85. 85.
    Beckmann W (1986) J Crystal Growth 79: 797CrossRefGoogle Scholar
  86. 86.
    Beckmann W (1986) J Sci Instrum 19: 444CrossRefGoogle Scholar
  87. 87.
    Beckmann W, Kammer S, Meier J, Boistelle R (1986) J Crystal Growth 74: 326CrossRefGoogle Scholar
  88. 88.
    Beckmann W, Kammer S, Rauls M (1987) Fat Sci Technol 89: 313Google Scholar
  89. 89.
    Sato K, Boistelle R (unpublished data)Google Scholar
  90. 90.
    Kuhn H (1983) Thin Soild Films 99: 1CrossRefGoogle Scholar
  91. 91.
    Mistuya M, Taniguchi Y, Akagi M (1983) J Colloid Interface Sci 92: 29Google Scholar
  92. 92.
    Neuman RD, Fereshtehkhou S, Ovalle F (1984) J Colloid Interface Sci 101: 309CrossRefGoogle Scholar
  93. 93.
    Uyeda N, Takenaka H, Aoyama K, Matsumoto M, Fujiyoshi Y (1987) Nature 327: 319CrossRefGoogle Scholar
  94. 94.
    Mastuzaki F, Inaoka K, Okada M, Sato K (1984) J Crystal Growth 69: 231CrossRefGoogle Scholar
  95. 95.
    Agarwal VK, Ugasaki Y, Mitsubayashi H (1976) Japan J Appl Phys 15: 2327CrossRefGoogle Scholar
  96. 96.
    Ueda Y, Ashida M (1980) J Electron Microsc 29: 38Google Scholar
  97. 97.
    Ueda Y (1986) Bull Chem Soc Japan 59: 3775CrossRefGoogle Scholar
  98. 98.
    Ueda Y (1987) Bull Chem Soc Japan 60: 2011CrossRefGoogle Scholar
  99. 99.
    Miki T, Inaoka K, Sato K, Okada M (1985) Japan J Appl Phys 24: L672CrossRefGoogle Scholar
  100. 100.
    Yase K, Inoue T, Inaoka K, Okada M (1989) J Electron Microsc. 38: 132Google Scholar
  101. 101.
    Inoue T, Yase K, Inaoka K, Okada M (1987) J Crystal Growth 38: 306CrossRefGoogle Scholar
  102. 102.
    Davies M, Malpass VE (1961) J Chem Soc 1048Google Scholar
  103. 103.
    Cevc G, Marsh D (1987) in: Phospholipid bilayers, Wiley, New YorkGoogle Scholar
  104. 104.
    Garti N, Sato K (eds) (1988) Crystallization and polymorphism of fats and fatty acids, Marcel Dekker, New York, Chaps 4 and 6Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1991

Authors and Affiliations

  • Kiyotaka Sato
    • 1
  • Masamichi Kobayashi
    • 2
  1. 1.Faculty of Applied Biological ScienceHiroshima UniversityHigashi-Hiroshima, 724Japan
  2. 2.Department of Macromolecular Science, Faculty of ScienceOsaka UniversityToyonaka, 560Japan

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