Critical review and exergy analysis of formaldehyde production processes

Reviews in Chemical Engineering

Volumn 30, Issue 6, 2014, Pages 583-604

  Bahmanpour, Ali Mohammad ^a   Hoadley, Andrew ^a   Tanksale, Akshat ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

exergy analysis; formaldehyde; kinetics and mechanism; methanol ballast process

Indexed keywords

ADHESIVES; BALLAST (RAILROAD TRACK); CATALYSIS; COMPUTER SOFTWARE; EFFICIENCY; EXERGY; METHANOL; NATURAL GAS; NATURAL GASOLINE PLANTS; REACTION KINETICS; STEAM REFORMING; SYNTHESIS GAS;

EXERGY ANALYSIS; FORMALDEHYDE PRODUCTION; FORMALDEHYDE SYNTHESIS; INTERMEDIATE CHEMICALS; KINETICS AND MECHANISM; NATURAL GAS CONVERSION; PRODUCT SPECIFICATIONS; SUSTAINABLE PRODUCTS;

FORMALDEHYDE;

EID: 84912054680     PISSN: 01678299     EISSN: None     Source Type: Journal    
DOI: 10.1515/revce-2014-0022     Document Type: Review

References (93)

1. Adkins H, Peterson WR. The oxidation of methanol with air over iron, molybdenum, and iron-molybdenum oxides. J Am Chem Soc 1931; 53: 1512-1520
2. Albert M, Hahnenstein I, Hasse H, Maurer G. Vapor-Liquid equilibrium of formaldehyde mixtures: new data and model revision. AIChE J 1996; 42: 1741-1751
3. Albert M, Garcia BG, Kreiter C, Maurer G. Vapor-liquid and chemical equilibria of formaldehyde-water mixtures. AIChE J 1999; 45: 2024-2033
4. Albert M, García BC, Kuhnert C, Peschla R, Maurer G. Vapor-liquid equilibrium of aqueous solutions of formaldehyde and methanol. AIChE J 2000; 46: 1676-1687
5. Andreasen A, Lynggaard H, Stegelmann C, Stoltze P. A microkinetic model of the methanol oxidation over silver. Surf Sci 2003; 544: 5-23
6. Aries RS. Process for making anhydrous monomeric formaldehyde. US Patent application, 1960
7. Arthur BW, Maurice ND. Process of producing formaldehyde. US2196188 A, 1940
8. Bailey GC, Craver AE. Process of producing formaldehyde. US Patent application, 1921
9. Bao X, Barth JV, Lehmpfuhl G, Schuster R, Uchida Y, SchlÖgl R, Ertl G. Oxygen-induced restructuring of Ag(111). Surf Sci 1993a; 284: 14-22
10. Bao X, Muhler M, Pettinger B, SchlÖgl R, Ertl G. On the nature of the active state of silver during catalytic oxidation of methanol. Catal Lett 1993b; 22: 215-225
11. Barnes C, Pudney P, Guo Q, Bowker M. Molecular-beam studies of methanol partial oxidation on Cu(110). J Chem Soc Farad Trans 1990; 86: 2693-2699
12. Bejan A. Advanced engineering thermodynamics. New York: Wiley, 1997
13. Beznis NV, Van Laak ANC, Weckhuysen BM, Bitter JH. Oxidation of methane to methanol and formaldehyde over Co-ZSM-5 molecular sieves: tuning the reactivity and selectivity by alkaline and acid treatments of the zeolite ZSM-5 agglomerates. Microp Mesop Mater 2011; 138: 176-183
14. Bhattacharyya SK, Janakiram K, Ganguly ND. Kinetics of the vapor-phase oxidation of methyl alcohol on vanadium pentoxide catalyst. J Catal 1967; 8: 128-136
15. Bizzari SN. CEH marketing research report: formaldehyde. Chemical Industries Newsletter, 2007
16. Blair EW, Wheeler TS. The estimation of formaldehyde and acetaldehyde. Analyst 1923; 48: 110-112
17. Bobrova II, Bobrov NN, Simonova LG, Parmon VN. Direct catalytic oxidation of methane to formaldehyde: new investigation opportunities provided by an improved flow circulation method. Kinet Catal 2007; 48: 676-692
18. Bone WA, Smith HL. XCIV. - The thermal decomposition of formaldehyde and acetaldehyde. J Chem Soc Trans 1905; 87: 910-916
19. Brackman W. Process for the preparation of aldehydes and ketones. US Patent application, 1959
20. Brenk M. Silver catalyst for formaldehyde preparation. PCT/ EP2009/006170, 2010
21. Burcham LJ, Wachs IE. The origin of the support effect in supported metal oxide catalysts: in situ infrared and kinetic studies during methanol oxidation. Catal Today 1999; 49: 467-484
22. Busca G. On the mechanism of methanol oxidation over vanadia-based catalysts: a FT-IR study of the adsorption of methanol, formaldehyde and formic acid on vanad. J Mol Catal 1989; 50: 241-249
23. Calvert JG, Steacie EWR. Vapor phase photolysis of formaldehyde at wavelength 3130A. J Chem Phys 1951; 19: 176-182
24. Cao E, Gavriilidis A. Oxidative dehydrogenation of methanol in a microstructured reactor. Catal Today 2005; 110: 154-163
25. Carlsson PA, Jing D, Skoglundh M. Controlling selectivity in direct conversion of methane into formaldehyde/methanol over iron molybdate via periodic operation conditions. Energy Fuels 2012; 26: 1984-1987
26. Chauvel A, Lefebvre G. Petrochemical processes (volume 1: synthesis - Gas derivatives and major hydrocarbons). Houston, TX: Institut Francais du Petrole Publications, 1989
27. Christopher K, Dimitrios R. A review on exergy comparison of hydrogen production methods from renewable energy sources. Energy Environ Sci 2012; 5: 6640-6651
28. Cogliano VJ, Grosse Y, Baan RA, Straif K, Secretan MB, El Ghissassi F. Meeting report: summary of IARC monographs on formaldehyde, 2-butoxyethanol, and 1-tert-butoxy-2-propanol. Environ Health Perspect 2005; 113: 1205-1208
29. Demirel Y. Thermodynamic analysis. Arab J Sci Eng 2013; 38: 221-249
30. Deng J, Wu J. Formaldehyde production by catalytic dehydrogenation of methanol in inorganic membrane reactors. Appl Catal A 1994; 109: 63-76
31. Deo G, Wachs IE. Reactivity of supported vanadium oxide catalysts: the partial oxidation of methanol. J Catal 1994; 146: 323-334
32. Dincer I, Rosen MA. Chemical exergy. In: Dincer I, Rosen MA, editors. Exergy, 2nd ed. New York: Elsevier, 2013: chapter 3
33. Fajardo CAG, Niznansky D, Nguyen Y, Courson C, Roger AC. Methane selective oxidation to formaldehyde with Fe-catalysts supported on silica or incorporated into the support. Catal Commun 2008; 9: 864-869
34. Forzatti P, Tronconi E, Elmi AS, Busca G. Methanol oxidation over vanadia-based catalysts. Appl Catal A 1997; 157: 387-408
35. Francis SM, Leibsle FM, Haq S, Xiang N, Bowker M. Methanol oxidation on Cu(110). Surf Sci 1994; 315: 284-292
36. Gómez-Ramírez A, Rico VJ, Cotrino J, González-Elipe AR, Lambert RM. Low temperature production of formaldehyde from carbon dioxide and ethane by plasma-assisted catalysis in a ferroelectrically moderated dielectric barrier discharge reactor. ACS Catal 2014; 4: 402-408
37. Hasse H, Maurer G. Vapor-liquid equilibrium of formaldehydecontaining mixtures at temperatures below 320 K. Fluid Phase Equilibria 1991; 64: 185-199
38. Hasse H, Hahnenstein I, Maurer G. Revised vapor-liquid equilibrium model for multicomponent formaldehyde mixtures. AIChE J 1990; 36: 1807-1814
39. He J, Li Y, An D, Zhang Q, Wang Y. Selective oxidation of methane to formaldehyde by oxygen over silica-supported iron catalysts. J Nat Gas Chem 2009; 18: 288-294
40. Kirk RE, Othmer DF. Kirk-Othmer encyclopedia of chemical technology. New Jersey: Wiley, 1991
41. Kuhnert C, Albert M, Breyer S, Hahnenstein I, Hasse H, Maurer G. Phase equilibrium in formaldehyde containing multicomponent mixtures: experimental results for fluid phase equilibria of (formaldehyde+(water or methanol)+methylal) and (formal dehyde+water+methanol+methylal) and comparison with predictions. Ind Eng Chem Res 2006; 45: 5155-5164
42. Launay H, Loridant S, Nguyen DL, Volodin AM, Dubois JL, Millet JMM. Vanadium species in new catalysts for the selective oxidation of methane to formaldehyde: activation of the catalytic sites. Catal Today 2007; 128: 176-182
43. Lausche AC, Hummelshoj JS, Abild-Pedersen F, Studt F, Norskov JK. Application of a new informatics tool in heterogeneous catalysis: analysis of methanol dehydrogenation on transition metal catalysts for the production of anhydrous formaldehyde. J Catal 2012; 291: 133-137
44. Leibsle FM, Francis SM, Haq S, Bowker M. Aspects of formaldehyde synthesis on Cu(110) as studied by STM. Surf Sci 1994; 318: 46-60
45. Lou Y, Wang H, Zhang Q, Wang Y. SBA-15-supported molybdenum oxides as efficient catalysts for selective oxidation of ethane to formaldehyde and acetaldehyde by oxygen. J Catal 2007a; 247: 245-255
46. Lou Y, Zhang Q, Wang H, Wang Y. Catalytic oxidation of ethylene and ethane to formaldehyde by oxygen. J Catal 2007b; 250: 365-368
47. Lunev NK, Shmyrko YI, Pavlenko NV, Norton B. Selective formation of formaldehyde from carbon dioxide and hydrogen over PtCu/ SiO2. Appl Organomet Chem 2001; 15: 148-150
48. Mann RS, Dosi MK. Kinetics of vapor-phase oxidation of methyl alcohol on vanadium pentoxide-molybdenum trioxide catalyst. J Catal 1973; 28: 282-288
49. Mars P, van Krevelen DW. Oxidations carried out by means of vanadium oxide catalysts. Chem Eng Sci 1954; 3 (Suppl 1): 41-59
50. Maurer G. Vapor-liquid equilibrium of formaldehyde- and water-containing multicomponent mixtures. AIChE J 1986; 32: 932-948
51. Michalkiewicz B, Srenscek-Nazzal J, Tabero P, Grzmil B, Narkiewicz U. Selective methane oxidation to formaldehyde using polymorphic T-, M-, and H-forms of niobium(V) oxide as catalysts. Chem Papers 2008; 62: 106-113
52. Nagy A, Mestl G, Rühle T, Weinberg G, SchlÖgl R. The dynamic restructuring of electrolytic silver during the formaldehyde synthesis reaction. J Catal 1998; 179: 548-559
53. Nagy AJ, Mestl G, Herein D, Weinberg G, Kitzelmann E, SchlÖgl R. The correlation of subsurface oxygen diffusion with variations of silver morphology in the silver-oxygen system. J Catal 1999; 182: 417-429
54. Nakata K, Ozaki T, Terashima C, Fujishima A, Einaga Y. High-yield electrochemical production of formaldehyde from CO2 and seawater. Angew Chem Int Ed 2014; 53: 871-874
55. National Fire Protection Association. Fire protection guide to hazardous materials. Quincy, MA: National Fire Protection Association, 1994
56. Newton RH, Dodge BF. The equilibrium between carbon monoxide, hydrogen, formaldehyde and methanol.1 I. the reactions CO+H2 HCOH and H2+HCOH CH3OH. J Am Chem Soc 1933; 55: 4747-4759
57. Polnišer R, Štolcová M, Hronec M, Mikula M. Structure and reactivity of copper iron pyrophosphate catalysts for selective oxidation of methane to formaldehyde and methanol. Appl Catal A 2011; 400: 122-130
58. Punderson JO. Dehydrogenation of alcohols to aldehydes. US Patent application, 1960
59. Qian M, Liauw MA, Emig G. Formaldehyde synthesis from methanol over silver catalysts. Appl Catal A 2003; 238: 211-222
60. Reuss G, Disteldorf W, Gamer AO, Hilt A. Ullmanns encyclopedia of industrial chemistry. Weinheim: Wiley, 2003
61. Roeda DDF. Preparation of formaldehyde using a silver-containing ceramic catalyst. J Label Compd Radiopharm 2003; 46: 449
62. Routray K, Zhou W, Kiely CJ, Grünert W, Wachs IE. Origin of the synergistic interaction between MoO3 and iron molybdate for the selective oxidation of methanol to formaldehyde. J Catal 2010; 275: 84-98
63. Sabatier P, Mailhe A. Actions des oxydes metalliques sur les alcools primaires. Ann Chim Phys 1910; 20: 289-352
64. Sexton BA. Methanol decomposition on platinum (111). Surf Sci 1981; 102: 271-281
65. Sexton AW, Kartheuser B, Batiot C, Zanthoff HW, Hodnett BK. The limiting selectivity of active sites on vanadium oxide catalysts supported on silica for methane oxidation to formaldehyde. Catal Today 1998; 40: 245-250
66. Shreiber EH, Roberts GW. Methanol dehydrogenation in a slurry reactor: evaluation of copper chromite and iron/titanium catalysts. Appl Catal B 2000; 26: 119-129
67. Soares APV, Farinha Portela M, Kiennemann A, Hilaire L, Millet JMM. Iron molybdate catalysts for methanol to formaldehyde oxidation: effects of Mo excess on catalytic behaviour. Appl Catal A 2001; 206: 221-229
68. Spence R, Wild W. The thermal reaction between chlorine and formaldehyde. J Am Chem Soc 1935; 57: 1145-1146
69. Su S, Prairie MR, Renken A. Reaction mechanism of methanol dehydrogenation on a sodium carbonate catalyst. Appl Catal A 1992; 91: 131-142
70. Szargut J, Morris DR, Steward FR. Exergy analysis of thermal, chemical, and metallurgical processes. New York: Hemisphere Publishing, 1988
71. Tang X, Bai Y, Duong A, Smith MT, Li L, Zhang L. Formaldehyde in China: production, consumption, exposure levels, and health effects. Environment International 2009; 35: 1210-1224
72. Tatibouët JM, Germain JE. A structure-sensitive oxidation reaction: methanol on molybdenum trioxide catalysts. J Catal 1981; 72: 375-378
73. Thomas MD. Preparation of formaldehyde. 1. J Am Chem Soc 1920; 42: [867]-882
74. Tolmacsov P, Gazsi A, Solymosi F. Decomposition and reforming of methanol on Pt metals supported by carbon Norit. Appl Catal A 2009; 362: 58-61
75. Trillat A. Investigation on the catalytic oxidation of the alcohols. Bull Soc Chim France 1903; 29: 35
76. Tsatsaronis G. Definitions and nomenclature in exergy analysis and exergoeconomics. Energy 2007; 32: 249-253
77. Turton R, Bailie RC, Whiting WB, Shaeiwitz JA, Bhattacharyya A. Analysis, synthesis, and design of chemical processes. New Jersey: Prentice Hall, 2009
78. Ulukardesler AH, Atalay S, Atalay FS. Determination of optimum conditions and the kinetics of methanol oxidation. Chem Eng Technol 2010; 33: 167-176
79. Van Veen AC, Hinrichsen O, Muhler M. Mechanistic studies on the oxidative dehydrogenation of methanol over polycrystalline silver using the temporal-analysis-of-products approach. J Catal 2002; 210: 53-66
80. Vining WC, Strunk J, Bell AT. Investigation of the structure and activity of VOx/ZrO2/SiO2 catalysts for methanol oxidation to formaldehyde. J Catal 2011; 281: 222-230
81. Vining WC, Strunk J, Bell AT. Investigation of the structure and activity of VOx/CeO2/SiO2 catalysts for methanol oxidation to formaldehyde. J Catal 2012; 285: 160-167
82. Wachs IE, Madix RJ. The oxidation of methanol on a silver (110) catalyst. Surf Sci 1978a; 76: 531-558
83. Wachs IE, Madix RJ. The selective oxidation of CH3OH to H2CO on a copper(110) catalyst. J Catal 1978b; 53: 208-227
84. Walker JF. Formaldehyde. New York: Reinhold Publishing, 1967
85. Wang Q, Li Y, Chen X. Exergy analysis of liquefied natural gas cold energy recovering cycles. Int J Energy Res 2005; 29: 65-78
86. Wang ZC, Dietl N, Kretschmer R, Ma JB, Weiske T, Schlangen M, Schwarz H. Direct conversion of methane into formaldehyde mediated by [Al2O3]+ at room temperature. Angew Chem Int Ed 2012; 51: 3703-3707
87. Waterhouse GIN, Bowmaker GA, Metson JB. Influence of catalyst morphology on the performance of electrolytic silver catalysts for the partial oxidation of methanol to formaldehyde. Appl Catal A 2004; 266: 257-273
88. Zaza P, Randall H, Doepper R, Renken A. Dynamic kinetics of catalytic dehydrogenation of methanol to formaldehyde. Catal Today 1994; 20: 325-334
89. Zhang X, He DH, Zhang QJ, Ye Q, Xu BQ, Zhu QM. Selective oxidation of methane to formaldehyde over Mo/ZrO2 catalysts. Appl Catal A 2003; 249: 107-117
90. Zhang H, Sun K, Feng Z, Ying P, Li C. Studies on the SbOx species of SbOx/SiO2 catalysts for methane-selective oxidation to formaldehyde. Appl Catal A 2006; 305: 110-119
91. Zhang J, Burklé-Vitzthum V, Marquaire PM, Wild G, Commenge JM. Direct conversion of methane in formaldehyde at very short residence time. Chem Eng Sci 2011; 66: 6331-6340
92. Zhang J, Burklé-Vitzthum V, Marquaire PM. NO2-promoted oxidation of methane to formaldehyde at very short residence time - Part II: kinetic modeling. Chem Eng J 2012a; 197: 123-134
93. Zhang J, Burklé-Vitzthum V, Marquaire PM. NO2-promoted oxidation of methane to formaldehyde at very short residence time. Part I: experimental results. Chem Eng J 2012b; 189-190: 393-403