메뉴 건너뛰기




Volumn 13, Issue 27, 2007, Pages 7673-7681

Polyamide synthesis from 6-aminocapronitrile, part 2: Heterogeneously catalyzed nitrile hydrolysis with consecutive amine amidation

Author keywords

Amides; Heterogeneous catalysis; Hydrolysis; Metal oxides; Nitriles; Zirconium

Indexed keywords

AMIDES; CATALYSIS; HYDROLYSIS; MATHEMATICAL MODELS; REACTION KINETICS; ZIRCONIUM COMPOUNDS;

EID: 34748892366     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601898     Document Type: Article
Times cited : (16)

References (58)
  • 1
    • 34748896348 scopus 로고    scopus 로고
    • 1) a) B. S. Curatolo, R. C. Sentman, G. P. Coffey Standard Oil Co, US Patent 4629776, 1986;
    • [1) a) B. S. Curatolo, R. C. Sentman, G. P. Coffey (Standard Oil Co.), US Patent 4629776, 1986;
  • 2
    • 34748918092 scopus 로고    scopus 로고
    • R. Mohrschladt, V. Hildebrandt BASF A.-G, WO Patent 9943734, 1998;
    • b) R. Mohrschladt, V. Hildebrandt (BASF A.-G.), WO Patent 9943734, 1998;
  • 3
    • 34748920446 scopus 로고    scopus 로고
    • D. N. Marks DuPont, EP Patent 479306, 1991;
    • c) D. N. Marks (DuPont), EP Patent 479306, 1991;
  • 4
    • 34748828352 scopus 로고    scopus 로고
    • E. K. Marchildon, A. T. Mutel DuPont, WO Patent 2000024808, 1998;
    • d) E. K. Marchildon, A. T. Mutel (DuPont), WO Patent 2000024808, 1998;
  • 5
    • 34748881576 scopus 로고    scopus 로고
    • R. Mohrschladt, H. Winterling, D. Krauss BASF A.-G, DE Patent 19962573, 1995;
    • e) R. Mohrschladt, H. Winterling, D. Krauss (BASF A.-G.), DE Patent 19962573, 1995;
  • 6
    • 34748912747 scopus 로고    scopus 로고
    • R. Mohrschladt, V. Hildebrandt BASF A.-G, WO Patent 9938905, 1998;
    • f) R. Mohrschladt, V. Hildebrandt (BASF A.-G.). WO Patent 9938905, 1998;
  • 7
    • 34748845497 scopus 로고    scopus 로고
    • R. Mohrschladt, D. Krauss, V. Hildebrandt BASF A.-G, WO Patent 9938906, 1998;
    • g) R. Mohrschladt, D. Krauss, V. Hildebrandt (BASF A.-G.), WO Patent 9938906, 1998;
  • 8
    • 34748836171 scopus 로고    scopus 로고
    • R. Mohrschladt, V. Hildebrandt, E. Fuchs BASF A.-G, WO Patent 9938908, 1998;
    • h) R. Mohrschladt, V. Hildebrandt, E. Fuchs (BASF A.-G.), WO Patent 9938908, 1998;
  • 9
    • 34748862742 scopus 로고    scopus 로고
    • J. D. Cohen, S. B. Fergusson, E. K. Marchildon, D. N. Marks, A. Mutel DuPont, US Patent 6437089, 2001;
    • i) J. D. Cohen, S. B. Fergusson, E. K. Marchildon, D. N. Marks, A. Mutel (DuPont), US Patent 6437089, 2001;
  • 10
    • 34748900972 scopus 로고    scopus 로고
    • C. H. Greenewalt DuPont, US Patent 2245129, 1938;
    • j) C. H. Greenewalt (DuPont). US Patent 2245129, 1938;
  • 11
    • 34748842389 scopus 로고    scopus 로고
    • R. Weiss, D. Krauss, D. Keller, G. Pipper, W. Harder, A. Ludwig, R. Mohrschladt BASF A.-G, WO Patent 9808889, 1997;
    • k) R. Weiss, D. Krauss, D. Keller, G. Pipper, W. Harder, A. Ludwig, R. Mohrschladt (BASF A.-G.), WO Patent 9808889, 1997;
  • 12
    • 34748813438 scopus 로고    scopus 로고
    • H. Liehr Zimmer A.-G, US Patent 5627257, 1996;
    • l) H. Liehr (Zimmer A.-G.), US Patent 5627257, 1996;
  • 13
    • 34748916787 scopus 로고    scopus 로고
    • D. N. Marks DuPont, US Patent 5185427, 1991;
    • m) D. N. Marks (DuPont), US Patent 5185427, 1991;
  • 14
    • 34748901592 scopus 로고    scopus 로고
    • B. S. Curatolo Standard Oil Co, US Patent 4640976, 1985;
    • n) B. S. Curatolo (Standard Oil Co.), US Patent 4640976, 1985;
  • 15
    • 34748877498 scopus 로고    scopus 로고
    • G. P. Coffey Standard Oil Co, US Patent 4603192, 1985;
    • o) G. P. Coffey (Standard Oil Co.), US Patent 4603192, 1985;
  • 16
    • 34748890266 scopus 로고    scopus 로고
    • B. S. Curatolo Standard Oil Co, US Patent 4568736, 1984;
    • p) B. S. Curatolo (Standard Oil Co.), US Patent 4568736, 1984;
  • 17
    • 34748912116 scopus 로고    scopus 로고
    • B. S. Curatolo Standard Oil Co, US Patent 4542205, 1984;
    • q) B. S. Curatolo (Standard Oil Co.), US Patent 4542205, 1984;
  • 18
    • 34748815387 scopus 로고    scopus 로고
    • R. Mohrschladt, H. Winterling, D. Krauss BASF A.-G, DE Patent 19962573, 1996
    • r) R. Mohrschladt, H. Winterling, D. Krauss (BASF A.-G.). DE Patent 19962573, 1996.
  • 19
    • 34748820534 scopus 로고    scopus 로고
    • Part 1 in this series: A. J. M. Van Dijk, T. Heyligen R. Duchateau J. Meuldijk, C. E. Koning, Chem. Eur. J. 2007, 13, 10.1002/chem.200601897.
    • Part 1 in this series: A. J. M. Van Dijk, T. Heyligen R. Duchateau J. Meuldijk, C. E. Koning, Chem. Eur. J. 2007, 13, 10.1002/chem.200601897).
  • 20
    • 0000500402 scopus 로고
    • A number of patents consider the gas-phase conversion of an aliphatic amino-nitrile into the corresponding N-substituted amide by using metal oxides, mainly aimed at the synthesis of the corresponding lactams
    • a) M. Lasperas, P. Graffin, P. Geneste, J. Catal. 1993, 139, 362-370. A number of patents consider the gas-phase conversion of an aliphatic amino-nitrile into the corresponding N-substituted amide by using metal oxides, mainly aimed at the synthesis of the corresponding lactams.
    • (1993) J. Catal , vol.139 , pp. 362-370
    • Lasperas, M.1    Graffin, P.2    Geneste, P.3
  • 21
    • 34748903876 scopus 로고    scopus 로고
    • J.-P. Brunelle, C. Nedez Rhodia, WO Patent 2000004994, 1999;
    • b) J.-P. Brunelle, C. Nedez (Rhodia), WO Patent 2000004994, 1999;
  • 22
    • 34748836168 scopus 로고    scopus 로고
    • H.-J. Buysch, O. Immel, R. Langer Bayer A.-G, DE Patent 19632006, 1996;
    • c) H.-J. Buysch, O. Immel, R. Langer (Bayer A.-G.), DE Patent 19632006, 1996;
  • 23
    • 34748826540 scopus 로고
    • EP Patent 150295
    • d) F. Mares (Allied Co.), EP Patent 150295, 1984;
    • (1984)
    • Mares, F.1
  • 25
    • 34748881002 scopus 로고    scopus 로고
    • M. Eiermann BASF A.-G, DE Patent 19753301, 1997;
    • f) M. Eiermann (BASF A.-G.), DE Patent 19753301, 1997;
  • 26
    • 34748917364 scopus 로고    scopus 로고
    • E. L. Martin DuPont, US Patent 2357484, 1944. The operating temperature is typically near or above 300°C. However, under these conditions the uncatalyzed nitrile hydrolysis already proceeds with a decent rate, making it difficult to measure the effect of the oxide
    • g) E. L. Martin (DuPont), US Patent 2357484, 1944. The operating temperature is typically near or above 300°C. However, under these conditions the uncatalyzed nitrile hydrolysis already proceeds with a decent rate, making it difficult to measure the effect of the oxide.
  • 27
    • 0040887778 scopus 로고    scopus 로고
    • Furthermore, the process requires a highly dilute system to obtain the lactam, which corresponds to a large excess of water in the process
    • h) A. Kramer, S. Mittelstadt, H. Vogel, Chem. Eng. Technol. 1999, 22, 494-500. Furthermore, the process requires a highly dilute system to obtain the lactam, which corresponds to a large excess of water in the process.
    • (1999) Chem. Eng. Technol , vol.22 , pp. 494-500
    • Kramer, A.1    Mittelstadt, S.2    Vogel, H.3
  • 29
    • 4544239197 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 1576-1580;
    • (2004) Chem. Int. Ed , vol.43 , pp. 1576-1580
    • Angew1
  • 31
  • 37
    • 34748914000 scopus 로고    scopus 로고
    • Although ruthenium on Al2O3 is highly active for the selective nitrile hydrolysis ref, 4a, with our system a 30, loss of amine selectivity in the conversion of hexylamine into N-hexylpentanamide is observed after 2 h, at 160°C. Furthermore, the presence of nitrile, amine, and water results in leaching of the metal because a clear-colored reaction mixture was observed, due to ruthenium in solution
    • 3 is highly active for the selective nitrile hydrolysis (ref. [4a], with our system a 30 % loss of amine selectivity in the conversion of hexylamine into N-hexylpentanamide is observed after 2 h, at 160°C. Furthermore, the presence of nitrile, amine, and water results in leaching of the metal because a clear-colored reaction mixture was observed, due to ruthenium in solution.
  • 44
    • 34748839959 scopus 로고    scopus 로고
    • For the uncatalyzed amidation the only observed product is N-hexylpentanamide
    • For the uncatalyzed amidation the only observed product is N-hexylpentanamide.
  • 51
    • 0003776661 scopus 로고
    • Eds, L. M. Sverdlov, M. A. Kovner, E. P. Krainov, Jerusalem, Israel program for Scientific Translations
    • b) Vibrational Spectra of Polyatomic Molecules (Eds.: L. M. Sverdlov, M. A. Kovner, E. P. Krainov), Jerusalem, Israel program for Scientific Translations, 1974.
    • (1974) Vibrational Spectra of Polyatomic Molecules
  • 58
    • 34748855271 scopus 로고    scopus 로고
    • PhD Thesis, Eindhoven University of Technology The Netherlands
    • M. A. G. Jansen, PhD Thesis, Eindhoven University of Technology (The Netherlands), 2005.
    • (2005)
    • Jansen, M.A.G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.