Advertisement

Reaction Kinetics, Mechanisms and Catalysis

, Volume 127, Issue 2, pp 787–801 | Cite as

Formation and transformation of nitroso compounds of ketoxime isomers in ketone ammoximation catalyzed by hollow titanium silicalite

  • Shengjian ZhangEmail author
  • Hong Zhao
  • Xiaoyong Wang
  • Shu Luo
  • Yuanqing Shi
  • Yingxian Zhao
  • Liyan Ying
  • Jie Chen
Article
  • 12 Downloads

Abstract

2-Nitrosopropane as the isomer of acetoxime was first found in ammoxidation of acetone with hydrogen peroxide catalyzed by hollow titanium silicalite (HTS). Experimental investigation indicates that the formation of 2-nitrosopropane was closely related to the pore size and surface acidity of HTS zeolite and significantly affected by reaction conditions, and further revealed that once formed, this isomer could be easily converted into main product acetoxime and also turned into by-product 2-nitropropane in the presence of excess hydrogen peroxide or O2. Based on the experimental results in combination with the analysis of reaction mechanism, it was suggested that the pathways of acetone ammoxidation catalyzed by HTS could involve both hydroxylamino intermediate and imino intermediate. The former was dominant in the production of acetone oxime, while the latter was mainly responsible for the formation of 2-nitropropane. In the latter case, an acetone first reacted with ammonia to form an imine and then interacted with an active center of Ti-OOH on catalyst to generate an unstable 2-nitrosopropane.

Keywords

Hollow titanium silicalite Ketone ammoximation Mechanism pathway Imine Nitroso propane 

Notes

Acknowledgement

The support of the Zhejiang Province Natural Science Foundation of China (Granted No. LY13B030003) is greatly acknowledged.

Supplementary material

11144_2019_1597_MOESM1_ESM.docx (102 kb)
Supplementary material 1 (DOCX 101 kb)

References

  1. 1.
    Taramasso M, Perego G, Notari B (1983), US Patent 4,410,501 to SNAM Progetti, ItalyGoogle Scholar
  2. 2.
    Tuel A, Moussa-Khouzami S, Taarit YB et al (1991) Hydroxylation of phenol over TS-1: surface and solvent effects. J Mol Catal 68:45–52CrossRefGoogle Scholar
  3. 3.
    Maspero F, Romano U (1994) Oxidation of alcohols with H2O2 catalyzed by titanium silicalite-1. J Catal 146:476–482CrossRefGoogle Scholar
  4. 4.
    Reddy JS, Sayari A (1995) Oxidation of propylamine over titanium silicate molecular sieves. Appl Catal A 128:231–242CrossRefGoogle Scholar
  5. 5.
    Clerici M, Bellussi G, Romano U (1991) Synthesis of propylene oxide from propylene and hydrogen peroxide catalyzed by titanium silicalite. J Catal 129:159–167CrossRefGoogle Scholar
  6. 6.
    Sheldon RA, Dakka J (1994) Heterogeneous catalytic oxidations in the manufacture of fine chemicals. Catal Today 19:215–245CrossRefGoogle Scholar
  7. 7.
    Huybrechts D, De Bruycker L, Jacobs P (1990) Oxyfunctionalization of alkanes with hydrogen peroxide on titanium silicalite. Nature 345:240–242CrossRefGoogle Scholar
  8. 8.
    Clerici MG (1991) Oxidation of saturated hydrocarbons with hydrogen peroxide, catalysed by titanium silicalite. Appl Catal 68:249–261CrossRefGoogle Scholar
  9. 9.
    Thangaraj A, Sivasanker S, Ratnasamy P (1991) Catalytic properties of crystalline titanium silicalites III. Ammoximation of cyclohexanone. J Catal 131:394–400CrossRefGoogle Scholar
  10. 10.
    Shi CF, Zhu B, Lin M et al (2011) Cyclohexane mild oxidation catalyzed by new titanosilicate with hollow structure. Catal Today 175:398–403CrossRefGoogle Scholar
  11. 11.
    Zhao S, Xie W, Yang JX et al (2011) An investigation into cyclohexanone ammoximation over Ti-MWW in a continuous slurry reactor. Appl Catal A 394:1–8CrossRefGoogle Scholar
  12. 12.
    Reddy JS, Sivasanker S, Ratnasamy P (1991) Ammoximation of cyclohexanone over a titanium silicate molecular sieve, TS-2. J Mol Catal 69:383–392CrossRefGoogle Scholar
  13. 13.
    Tvaruzkova Z, Habersberger K, Zilkova N et al (1991) Role of surface complexes on titanium-silicate in the ammoximation of cyclohexanone with hydrogen peroxide. Appl Catal A 79:105–114CrossRefGoogle Scholar
  14. 14.
    Sooknoi T, Chitranuwatkul V (2005) Ammoximation of cyclohexanone in acetic acid using tiatanium silicalite-1 catalyst: activity and reaction pathway. J Mol Catal A 236:220–226CrossRefGoogle Scholar
  15. 15.
    Zecchina A, Spoto G, Bordiga S et al (1993) Ammoximation of cyclohexanone on titanium silicalite—investigation of the reaction-mechanism. Stud Surf Sci Catal 75:719–729CrossRefGoogle Scholar
  16. 16.
    Wu P, Komatsu T, Yashima T (1997) Ammoximation of ketones over titanium mordenite. J Catal 168:400–411CrossRefGoogle Scholar
  17. 17.
    Dal Pozzo L, Fornasari G, Monti T (2002) TS-1, catalytic mechanism in cyclohexanoneoxime production. Catal Commun 3:369–375CrossRefGoogle Scholar
  18. 18.
    Zecchin A, Bordiga S, Lamberti C et al (1996) Structural characterization of Ti centres in Ti-silicalite and reaction mechanisms in cyclohexanoneammoximation. Catal Today 32:97–106CrossRefGoogle Scholar
  19. 19.
    Wang Y, Zhang SJ, Zhao YX et al (2014) The mechanism of catalyst deactivation and by-product formation in acetone ammoximation catalyzed by hollow titanium silicalite. J Mol Catal A 385:1–6CrossRefGoogle Scholar
  20. 20.
    Varlamov SV, Kadorkina GK, Kostyanovskii RG (1988) Hydroxymethylation, alkoxymethylation and aminomethylation of NH-oxaziridines. Khim Geterotsikl Soedin (Chem Heterocycl Compd) 243:90–395Google Scholar
  21. 21.
    Wang CY (1993) Application of oxaziridines in organic synthesis. Chem Reag 15:31–34Google Scholar
  22. 22.
    Zhang SJ, Zhang H, Shi YQ et al (2010) O-Alkylation of ketone oxime in ionic liquids. Chin J Org Chem 30:606–610Google Scholar
  23. 23.
    Gowenlock B, Trotman J (1955) Geometrical isomerism of dimericnitrosomethane. J Chem Soc.  https://doi.org/10.1039/jr9550004190 Google Scholar
  24. 24.
    Long JA, Harris NJ, Lammertsma K (2001) Formaldehyde oxime reversible arrow nitrosomethane tautomersim. J Org Chem 66:6762–6767CrossRefGoogle Scholar
  25. 25.
    Chu QY, He GK, Xi Y et al (2018) Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1. Catal Commun 108:46–50CrossRefGoogle Scholar
  26. 26.
    Wang YR, Lin M, Tuel A (2007) Hollow TS-1 crystals formed via a dissolution–recrystallization process. Micropor Mesopor Mater 102:80–85CrossRefGoogle Scholar
  27. 27.
    Notari B (1990) Titanium silicalite: a new selective oxidation catalyst, structure-activity and selectivity relationships in heterogenous catalysis. Stud Surf Sci Catal 60:243–252Google Scholar
  28. 28.
    Chen J, Zhao YX, Zhang YM et al (2018) Efects of TMPDO and 4-NOH-TMPD on H2O2/HTS catalytic system for free radicals generation and its application. Chem J Chin Univ 39:497–505CrossRefGoogle Scholar
  29. 29.
    Shang Y, Zhang SJ, Zhao YX et al (2016) The adsorption mechanisms of TMPDO and 4-NOH-TMPD in HTS/H2O2 system and effects on the stabilization of Ti-OOH. Chem J Chin Univ 37:946–955Google Scholar

Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2019

Authors and Affiliations

  1. 1.Ningbo Institute of TechnologyZhejiang UniversityNingboPeople’s Republic of China
  2. 2.Ningbo Siming Chemical Co., LtdNingboPeople’s Republic of China

Personalised recommendations