NMR spectroscopic study of the aldoxane formation in aqueous acetaldehyde solutions

Industrial and Engineering Chemistry Research

Volumn 53, Issue 20, 2014, Pages 8395-8403

  Scheithauer, Andreas ^a   Grützner, Thomas ^a   Rijksen, Christiaan ^a   Zollinger, Daniel ^a   Von Harbou, Erik ^a   Thiel, Werner R ^b   Hasse, Hans ^a  

^a University of Koblenz Landau   (Germany)

^b LONZA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL INDUSTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SPECTROSCOPIC ANALYSIS;

ACIDIC CONDITIONS; CHEMICAL EQUILIBRIUMS; CROTONALDEHYDE; LOWER TEMPERATURES; PRELIMINARY INFORMATION; SPECTROSCOPIC STUDIES; TWO-STEP PROCESS;

ACETALDEHYDE;

EID: 84901207717     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie5004043     Document Type: Article

References (48)

1. Eckert, M.; Fleischmann, G.; Jira, R.; Bolt, H. M.; Golka, K. Acetaldehyde. Ullmann's Encyclopedia of Industrial Chemistry, 6 th ed.; Wiley-VCH, 2006.
2. Fernandez, J.; Salomons, T. Crotonaldehyde Chem. Rev. 1962, 5, 485-502
3. Schulz, R.; Blumenstein, J.; Kohlpaintner, C. Crotonaldehyde and Crotonic Acid. Ullmann's Encyclopedia of Industrial Chemistry, 6 th ed.; Wiley-VCH, 2000.
4. Alhéritière, L. Process for Producing Acetaldol. Patent US 2489608, 1949.
5. Alhéritière, L. Manufacture of Aldol and/or Crotonaldehyde. Patent CA 511225D, 1955.
6. Craven, E.; Gell, W. Improvements in or Relating to the Production of Aldol and Crotonaldehyde. Patent GB 704854, 1950.
7. Heinz, W.; McLean, A. Aldol Condensation Reactions. Patent US 3077500, 1963.
8. Guimei, Y.; Hongwei, L. Process for Preparation of Crotonaldehyde. Patent CN 100344598C, 2006.
9. Mueller-Cunradi, M. Verfahren zur Herstellung von Crotonaldehyd. Patent DE 907888, 1954.
10. 13C-NMR Spectroscopic Study of Chemical Equilibria in Solutions of Formaldehyde in Water, Deuterium Oxide, and Methanol Ind. Eng. Chem. Res. 1994, 33, 1022-1029
11. Ahrens, M.; Strehlow, H. Acid Catalyzed Hydration of Acetaldehyde Discuss. Faraday Soc. 1965, 39, 112-120
12. Bell, R. P.; Clunie, J. C. The Hydration of Acetaldehyde in Aqueous Solution Trans. Faraday Soc. 1952, 48, 439-442
13. Bell, R. P.; Clunie, J. C. Binary and Ternary Mechanisms in the Hydration of Acetaldehyde Proc. R. Soc. Lond. A 1952, 212, 33-37
14. Podo, F.; Viti, V. A PMR Study of Hydration Products in Aqueous Acetaldehyde Solutions Org. Magn. Reson. 1970, 3, 259-261
15. Socrates, G. Hydration Study of Acetaldehyde and Propionaldehyde J. Org. Chem. 1969, 34 (10) 2958-2961
16. SoÌrensen, P.; Jencks, W. Acid- and Base-Catalyzed Decomposition of Acetaldehyde Hydrate and Hemiacetals in Aqueous Solution J. Am. Chem. Soc. 1987, 109, 4675-4690
17. Lombardi, E.; Sogo, P. NMR Study of Acetaldehyde-Water Mixtures J. Chem. Phys. 1960, 32, 635-636
18. Kurz, J. L. The Hydration of Acetaldehyde. I. Equilibrium Thermodynamic Parameters J. Am. Chem. Soc. 1967, 89, 3524-3528
19. Fujiwara, Y.; Fujiwara, S. Nuclear Magnetic Resonance Study of Acetaldehyde Aqueous Solution Bull. Chem. Soc. Jpn. 1963, 36, 574-578
20. Scheithauer, A. Physico-Chemical Data and Conceptual Design of a Crotonaldehyde Production Process. Ph.D. thesis, Laboratory of Engineering Thermodynamics, University of Kaiserslautern, 2014; Scientific Report Series 13, ISBN 978-3-944433-12-7.
21. Kohlpaintner, C.; Schulte, M.; Falbe, J.; Lappe, P.; Weber, J. Aldehydes, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry, 6 th ed.; Wiley-VCH, 2005.
22. Anderson, J.; Peters, M. Acetaldehyde Aldol Condensation Kinetics J. Chem. Eng. Data 1960, 5, 359-364
23. Newby, H. Improvements in the Production of Crotonaldehyde. Patent GB 660972, 1951.
24. Horn, O. Products with Commercial Possibilities from Reactions of Crotonaldehyde Ind. Eng. Chem. 1959, 51, 655-658
25. Bell, R.; McTigue, P. Kinetics of the Aldol Condensation of Acetaldehyde J. Chem. Soc. 1960, 2983-2994
26. Guthrie, J. The Aldol Condensation of Acetaldehyde: The Equilibrium Constant for the Reaction and the Rate Constant for the Hydroxide Catalyzed RetroAldol Reaction Can. J. Chem. 1974, 52, 2037-2040
27. Atalay, F.; Atalay, S. Kinetics of Acetaldol Production Chem. Ing. Tech. 1991, 63, 933-934
28. Matsuyama, H. Thermal Analysis of the Aldol Condensation Proc. Jpn. Acad. 1951, 27, 552-555
29. Atalay, S.; Atalay, F. S. Production of Crotonaldehyde from Acetaldol Dev. Chem. Eng. Miner. Process 1994, 2, 58-60
30. González Alafita, O. Investigación sobre la cinética del proceso de transformación del acetaldol a butiraldehído J. Mex. Chem. Soc. 1997, 41, 8-14
31. Hahnenstein, I.; Hasse, H.; Liu, Y.-Q.; Maurer, G. AIChE Symposium Series: Thermophysical Properties for Industrial Process Design; AIChE: New York, 1994; Vol. 90, 298, pp 141-157.
32. Ott, M.; Schoenmakers, H.; Hasse, H. Distillation of Formaldehyde Containing Mixtures: Laboratory Experiments, Equilibrium Stage Modeling and Simulation Chem. Eng. Process. 2005, 44, 687-694
33. Schilling, K.; Sohn, M.; Ströfer, E.; Hasse, H. Reactive Evaporation of Formaldehyde-containing Mixtures and Process Monitoring by Online NMR-Spectroscopy Chem. Ing. Tech. 2003, 75, 240-244
34. Grützner, T.; Lang, N.; Ströfer, E.; Hasse, H. Entwicklung eines neuen Trioxanverfahrens Chem. Ing. Tech. 2004, 76, 1342-1342
35. Maiwald, M.; Fischer, H. H.; Kim, Y.-K.; Albert, K.; Hasse, H. Quantitative High-Resolution On-line NMR Spectroscopy in Reaction and Process Monitoring J. Magn. Reson. 2004, 166, 135-146
36. Grützner, T.; Hasse, H.; Lang, N.; Siegert, M.; Ströfer, E. Development of a New Industrial Process for Trioxane Production Chem. Eng. Sci. 2007, 62, 5613-5620
37. Drunsel, J.-O.; Renner, M.; Hasse, H. Experimental Study and Model of Reaction Kinetics of Heterogeneously Catalyzed Methylal Synthesis Chem. Eng. Res. Des. 2012, 90, 696-703
38. Burger, J.; Ströfer, E.; Hasse, H. Chemical Equilibrium and Reaction Kinetics of the Heterogeneously Catalyzed Formation of Poly(oxymethylene) Dimethyl Ethers from Methylal and Trioxane Ind. Eng. Chem. Res. 2012, 51, 12751-12761
39. Späth, E.; Lorenz, R.; Freund, E. Über ein Additionsprodukt des Acetaldehyds an Acetaldol (V. Mitteil. über Derivate des Aldols und des Crotonaldehyds) Ber. Dtsch. Chem. Ges. 1943, 76, 57-68
40. Späth, E.; Lorenz, R.; Freund, E. Zur Kenntnis der Aldoxane (XII. Mitteil. über Derivate des Aldols und des Crotonaldehyds) Ber. Dtsch. Chem. Ges. 1944, 77, 354-361
41. Hanschke, E. Zur Kenntnis des Aldols. Über eine Verbindung aus Aldol und Acetaldehyd Ber. Dtsch. Chem. Ges. 1943, 76, 180-182
42. Saunders, R. H.; Murray, M. J. The Aldol Condensation. III. Aldol-aldehyde Addition Products and their Derivatives J. Am. Chem. Soc. 1944, 66, 206-208
43. Späth, E.; Schmid, H. Über die Konstitution des Paraldols (III. Mitteil. über Derivate des Aldols und des Crotonaldehyds) Ber. Dtsch. Chem. Ges. 1941, 74, 859-866
44. Vogel, M.; Rhum, D. The Structure of Paraldol J. Org. Chem. 1966, 31, 1775-1780
45. Späth, E.; Lorenz, R.; Freund, E. Über das Gleichgewicht zwischen monomerem und dimerem Acetaldol in wässeriger Lösung Monatsh. Chem. 1946, 76, 83-85
46. Owen, L. N. The Polymerisation of Acetaldol J. Chem. Soc. 1943, 445-446
47. Cheshnovsky, D.; Navon, G. Nuclear Magnetic Resonance Studies of Carbonic Anhydrase Catalyzed Reversible Hydration of Acetaldehyde by the Saturation Transfer Method Biochemistry 1980, 19, 1866-1873
48. Ammann, C.; Meier, P.; Merbach, A. A Simple Multinuclear NMR Thermometer J. Magn. Reson. 1982, 46, 319-321