参考文献/References:
[1] 崔丽凤, 侯志扬. 丙烯酸市场分析与技术发展趋势[J]. 化学工业, 2012, 30(7): 21-24.
[2] WEISSRMEL K, ARPE H J. Industrial organic chemistry[M]. 4th ed. Weinheim: Wiley-VCH, 2003: 291-296.
[3] LIN M M. Selective oxidation of propane to acrylic acid with molecular oxygen[J]. Applied Catalysis A: General, 2001, 207(1/2): 1-16.
[4] MAYO F R. Monomeric acrylic esters[J]. Journal of the American Chemical Society, 2002, 77(6): 1713-1714.
[5] 钱延龙, 缪世健. 均相催化反应进展[M]. 北京: 化学工业出版社, 1990, 10-13.
[6] SCHNIZER A W, WHEELER E N. Treating propiolactone with heated phosphoric acid to produce acrylic acid: US3176042[P]. 1965-03-30.
[7] 张俊峰. 乳酸高效催化转化制备丙烯酸研究[D]. 南京: 南京大学, 2011.
[8] 徐忠, 宁艳春, 严生虎, 等. 磷酸钠组合氧气预处理提高玉米秸秆酶解糖化效率[J]. 常州大学学报(自然科学版), 2021, 33(3): 65-74.
[9] BEERTHUIS R, ROTHENBERG G, SHIJU N R. Catalytic routes towards acrylic acid, adipic acid and ε-caprolactam starting from biorenewables[J]. Green Chemistry, 2015, 17(3): 1341-1361.
[10] HAYASHI H, SUGIYAMA S, KATAYAMA Y, et al. An alloy phase of Pd3Pb and the activity of Pb/Pd/C catalysts in the liquid-phase oxidation of sodium lactate to pyruvate[J]. Journal of Molecular Catalysis, 1994, 91(1): 129-137.
[11] ENGIN A, HALUK H, GURKAN K. Production of lactic acid esters catalyzed by heteropoly acid supported over ion-exchange resins[J]. Green Chemistry, 2003, 5(4): 460.
[12] LI K T, WANG C K, WANG I, et al. Esterification of lactic acid over TiO2-ZrO2 catalysts[J]. Applied Catalysis A: General, 2011, 392(1/2): 180-183.
[13] WADLEY D C, TAM M S, KOKITKAR P B, et al. Lactic acid conversion to 2, 3-pentanedione and acrylic acid over silica-supported sodium nitrate:reaction optimization and identification of sodium lactate as the active catalyst[J]. Journal of Catalysis, 1997, 165(2): 162-171.
[14] GUNTER G C, LANGFORD R H, JACKSON J E, et al. Catalysts and supports for conversion of lactic acid to acrylic acid and 2, 3-pentanedione[J]. Industrial & Engineering Chemistry Research, 1995, 34(3): 974-980.
[15] TAKEDA Y, SHOJI T, WATANABE H, et al. Selective hydrogenation of lactic acid to 1, 2-propanediol over highly active ruthenium-molybdenum oxide catalysts[J]. ChemSusChem, 2015, 8(7): 1170-1178.
[16] ZHANG Z G, JACKSON J E, MILLER D J. Aqueous-phase hydrogenation of lactic acid to propylene glycol[J]. Applied Catalysis A: General, 2001, 219(1/2): 89-98.
[17] UPARE P P, YOON J W, HWANG D W, et al. Design of a heterogeneous catalytic process for the continuous and direct synthesis of lactide from lactic acid[J]. Green Chemistry, 2016, 18(22): 5978-5983.
[18] CHEN G X, KIM H S, KIM E S, et al. Synthesis of high-molecular-weight poly(L-lactic acid)through the direct condensation polymerization of L-lactic acid in bulk state[J]. European Polymer Journal, 2006, 42(2): 468-472.
[19] KATRYNIOK B, PAUL S, DUMEIGNIL F. Highly efficient catalyst for the decarbonylation of lactic acid to acetaldehyde[J]. Green Chemistry, 2010, 12(11): 1910.
[20] ZHAI Z J, LI X L, TANG C M, et al. Decarbonylation of lactic acid to acetaldehyde over aluminum sulfate catalyst[J]. Industrial & Engineering Chemistry Research, 2014, 53(25): 10318-10327.
[21] MÜLLER V, KUHNE K, SCHUBART R, et al. Method for producing high-purity dilactide: 2000043381[P]. 2000-07-27.
[22] 贺璇, 郭锡坤, 郑敦胜, 等. 合成丙交酯工艺的改进[J]. 精细化工, 2004, 21(10): 745-747.
[23] MOK W S L, ANTAL M J J, JONES M J. Formation of acrylic acid from lactic acid in supercritical water[J]. The Journal of Organic Chemistry, 1989, 54(19): 4596-4602.
[24] LIRA C T, MCCRACKIN P J. Conversion of lactic acid to acrylic acid in near-critical water[J]. Industrial & Engineering Chemistry Research, 1993, 32(11): 2608-2613.
[25] HOLMEN R E. Production of acrylates by catalytic dehydration of lactic acid and alkyl lactates: US2859240[P]. 1958-11-04.
[26] PENG J S, LI X L, TANG C M, et al. Barium sulphate catalyzed dehydration of lactic acid to acrylic acid[J]. Green Chemistry, 2014, 16(1): 108-111.
[27] TANG C M, PENG J S, FAN G C, et al. Catalytic dehydration of lactic acid to acrylic acid over dibarium pyrophosphate[J]. Catalysis Communications, 2014, 43: 231-234.
[28] TANG C M, PENG J S, LI X L, et al. Strontium pyrophosphate modified by phosphoric acid for the dehydration of lactic acid to acrylic acid[J]. RSC Advances, 2014, 4(55): 28875.
[29] GUO Z, THENG D S, TANG K Y, et al. Dehydration of lactic acid to acrylic acid over lanthanum phosphate catalysts: the role of Lewis acid sites[J]. Physical Chemistry Chemical Physics: PCCP, 2016, 18(34): 23746-23754.
[30] KIBBY C L, HALL W K. Dehydrogenation of alcohols and hydrogen transfer from alcohols to ketones over hydroxyapatite catalysts[J]. Journal of Catalysis, 1973, 31(1): 65-73.
[31] TSUCHIDA T, JUN K B, YOSHIOKA T, et al. Reaction of ethanol over hydroxyapatite affected by Ca/P ratio of catalyst[J]. Journal of Catalysis, 2008, 259(2): 183-189.
[32] SILVESTER L, LAMONIER J F, FAYE J, et al. Reactivity of ethanol over hydroxyapatite-based Ca-enriched catalysts with various carbonate contents[J]. Catalysis Science & Technology, 2015, 5(5): 2994-3006.
[33] JORIS S J, AMBERG C H. Nature of deficiency in nonstoichiometric hydroxyapatites. I. catalytic activity of calcium and strontium hydroxyapatites[J]. The Journal of Physical Chemistry, 1971, 75(20): 3167-3171.
[34] GHANTANI V C, LOMATE S T, DONGARE M K, et al. Catalytic dehydration of lactic acid to acrylic acid using calcium hydroxyapatite catalysts[J]. Green Chemistry, 2013, 15(5): 1211.
[35] MATSUURA Y, ONDA A, YANAGISAWA K. Selective conversion of lactic acid into acrylic acid over hydroxyapatite catalysts[J]. Catalysis Communications, 2014, 48: 5-10.
[36] YAN B, TAO L Z, LIANG Y, et al. Sustainable production of acrylic acid: catalytic performance of hydroxyapatites for gas-phase dehydration of lactic acid[J]. ACS Catalysis, 2014, 4(6): 1931-1943.
[37] MATSUURA Y, ONDA A, OGO S, et al. Acrylic acid synthesis from lactic acid over hydroxyapatite catalysts with various cations and anions[J]. Catalysis Today, 2014, 226: 192-197.
[38] GHANTANI V C, DONGARE M K, UMBARKAR S B. Nonstoichiometric calcium pyrophosphate: a highly efficient and selective catalyst for dehydration of lactic acid to acrylic acid[J]. RSC Advances, 2014, 4(63): 33319-33326.
[39] SUN P, YU D H, FU K M, et al. Potassium modified NaY: a selective and durable catalyst for dehydration of lactic acid to acrylic acid[J]. Catalysis Communications, 2009, 10(9): 1345-1349.
[40] SUN P, YU D H, TANG Z C, et al. NaY zeolites catalyze dehydration of lactic acid to acrylic acid: studies on the effects of anions in potassium salts[J]. Industrial & Engineering Chemistry Research, 2010, 49(19): 9082-9087.
[41] ZHANG J F, ZHAO Y L, PAN M, et al. Efficient acrylic acid production through bio lactic acid dehydration over NaY zeolite modified by alkali phosphates[J]. ACS Catalysis, 2011, 1(1): 32-41.
[42] ZHANG J F, ZHAO Y L, FENG X Z, et al. Na2HPO4-modified NaY nanocrystallites: efficient catalyst for acrylic acid production through lactic acid dehydration[J]. Catalysis Science & Technology, 2014, 4(5): 1376-1385.
[43] ZHANG L L, THENG D S, DU Y H, et al. Selective conversion of lactic acid to acrylic acid over alkali and alkaline-earth metal co-modified NaY zeolites[J]. Catalysis Science & Technology, 2017, 7(24): 6101-6111.
[44] LARI G M, PUÉRTOLAS B, FREI M S, et al. Hierarchical NaY zeolites for lactic acid dehydration to acrylic acid[J]. ChemCatChem, 2016, 8(8): 1507-1514.
[45] YAN B, TAO L Z, LIANG Y, et al. Sustainable production of acrylic acid: alkali-ion exchanged beta zeolite for gas-phase dehydration of lactic acid[J]. ChemSusChem, 2014, 7(6): 1568-1578.
[46] YAN B, MAHMOOD A, LIANG Y, et al. Sustainable production of acrylic acid: Rb+- and Cs+-exchanged beta zeolite catalysts for catalytic gas-phase dehydration of lactic acid[J]. Catalysis Today, 2016, 269: 65-73.
[47] ZHANG X H, LIN L, ZHANG T, et al. Catalytic dehydration of lactic acid to acrylic acid over modified ZSM-5 catalysts[J]. Chemical Engineering Journal, 2016, 284: 934-941.
[48] YUAN C, LIU H Y, ZHANG Z K, et al. Alkali-metal-modified ZSM-5 zeolites for improvement of catalytic dehydration of lactic acid to acrylic acid[J]. Chinese Journal of Catalysis, 2015, 36(11): 1861-1866.
[49] YAN B, TAO L Z, MAHMOOD A, et al. Potassium-ion-exchanged zeolites for sustainable production of acrylic acid by gas-phase dehydration of lactic acid[J]. ACS Catalysis, 2017, 7(1): 538-550.
[50] GHAFFAR T, IRSHAD M, ANWAR Z, et al. Recent trends in lactic acid biotechnology: a brief review on production to purification[J]. Journal of Radiation Research and Applied Sciences, 2014, 7(2): 222-229.
[51] SU C Y, YU C C, CHIEN I L, et al. Control of highly interconnected reactive distillation processes: purification of raw lactic acid by esterification and hydrolysis[J]. Industrial & Engineering Chemistry Research, 2015, 54(27): 6932-6940.
[52] YANG X M, ZHANG Y L, ZHOU L P, et al. Production of lactic acid derivatives from sugars over post-synthesized Sn-beta zeolite promoted by WO3[J]. Food Chemistry, 2019, 289: 285-291.
[53] YANG X M, BIAN J J, HUANG J H, et al. Fluoride-free and low concentration template synthesis of hierarchical Sn-beta zeolites: efficient catalysts for conversion of glucose to alkyl lactate[J]. Green Chemistry, 2017, 19(3): 692-701.
[54] YAN Y, ZHANG Z H, BAK S M, et al. Confinement of ultrasmall cobalt oxide clusters within silicalite-1 crystals for efficient conversion of fructose into methyl lactate[J]. ACS Catalysis, 2019, 9(3): 1923-1930.
[55] ZHANG J, WANG L, WANG G X, et al. Hierarchical Sn-beta zeolite catalyst for the conversion of sugars to alkyl lactates[J]. ACS Sustainable Chemistry & Engineering, 2017, 5(4): 3123-3131.
[56] LEE J M, HWANG D W, HWANG Y K, et al. Efficient dehydration of methyl lactate to acrylic acid using Ca3(PO4)2-SiO2 catalyst[J]. Catalysis Communications, 2010, 11(15): 1176-1180.
[57] WANG B, LI C, ZHU Q Q, et al. The effect of K2HPO4 and Al2(SO4)3 modified MCM-41 on the dehydration of methyl lactate to acrylic acid[J]. RSC Advances, 2014, 4(86): 45679-45686.
[58] HONG J H, LEE J M, KIM H, et al. Efficient and selective conversion of methyl lactate to acrylic acid using Ca3(PO4)2-Ca2(P2O7)composite catalysts[J]. Applied Catalysis A: General, 2011, 396(1/2): 194-200.
[59] ZHANG J F, LIN J P, XU X B, et al. Evaluation of catalysts and optimization of reaction conditions for the dehydration of methyl lactate to acrylates[J]. Chinese Journal of Chemical Engineering, 2008, 16(2): 263-269.
[60] ZHANG Z Q, QU Y X, WANG S, et al. Catalytic performance and characterization of silica supported sodium phosphates for the dehydration of methyl lactate to methyl acrylate and acrylic acid[J]. Industrial & Engineering Chemistry Research, 2009, 48(20): 9083-9089.
[61] SHI H F, HU Y C, WANG Y, et al. KNaY-zeolite catalyzed dehydration of methyl lactate[J]. Chinese Chemical Letters, 2007, 18(4): 476-478.
[62] BLANCO E, LORENTZ C, DELICHERE P, et al. Dehydration of ethyl lactate over alkaline earth phosphates: performances, effect of water on reaction pathways and active sites[J]. Applied Catalysis B: Environmental, 2016, 180: 596-606.
[63] MURPHY B M, LETTERIO M P, XU B J. Catalytic dehydration of methyl lactate: reaction mechanism and selectivity control[J]. Journal of Catalysis, 2016, 339: 21-30.
[64] MURPHY B M, LETTERIO M P, XU B J. Selectivity control in the catalytic dehydration of methyl lactate: the effect of pyridine[J]. ACS Catalysis, 2016, 6(8): 5117-5131.
[65] MURPHY B M, LETTERIO M P, XU B J. Catalyst deactivation in pyridine-assisted selective dehydration of methyl lactate on NaY[J]. ACS Catalysis, 2017, 7(3): 1912-1930.
[66] MURPHY B, MOU T, WANG B, et al. The effect of cofed species on the kinetics of catalytic methyl lactate dehydration on NaY[J]. ACS Catalysis, 2018, 8(10): 9066-9078.
[67] LIU Z H, YAN B, LIANG Y, et al. Comparative study of gas-phase “dehydration” of alkyl lactates and lactic acid for acrylic acid production over hydroxyapatite catalysts[J]. Molecular Catalysis, 2020, 494: 111098.
[68] GUNTER G C, CRACIUN R, TAM M S, et al. FTIR and 31P-NMR spectroscopic analyses of surface species in phosphate-catalyzed lactic acid conversion[J]. Journal of Catalysis, 1996, 164(1): 207-219.
[69] TAM M S, GUNTER G C, CRACIUN R, et al. Reaction and spectroscopic studies of sodium salt catalysts for lactic acid conversion[J]. Industrial & Engineering Chemistry Research, 1997, 36(9): 3505-3512.
[70] YAN B, LIU Z H, LIANG Y, et al. Acrylic acid production by gas-phase dehydration of lactic acid over K+-exchanged ZSM-5: reaction variable effects, kinetics, and new evidence for cooperative acid-base bifunctional catalysis[J]. Industrial & Engineering Chemistry Research, 2020, 59(39): 17417-17428.
(责任编辑:谭晓荷)