复合催化剂在油酸豆甾醇酯合成中的应用

doi:10.11949/j.issn.0438-1157.20150552

化工学报 ›› 2015, Vol. 66 ›› Issue (8): 3078-3083.DOI: 10.11949/j.issn.0438-1157.20150552

• 催化、动力学与反应器 • 上一篇下一篇

复合催化剂在油酸豆甾醇酯合成中的应用

张硕, 杨亦文, 邢华斌, 苏宝根, 张治国, 鲍宗必, 杨启炜, 任其龙

浙江大学生物质化工教育部重点实验室, 化学工程与生物工程学院, 浙江杭州 310027

收稿日期:2015-05-04 修回日期:2015-05-30 出版日期:2015-08-05 发布日期:2015-08-05
通讯作者: 杨亦文
基金资助:
国家自然科学基金项目(21222601);教育部新世纪优秀人才支持计划(NCET-13-0524);浙江省重点科技创新团队计划(2011R50002)。

Synthesis of phytosteryl oleate using composite catalysts

ZHANG Shuo, YANG Yiwen, XING Huabin, SU Baogen, ZHANG Zhiguo, BAO Zongbi, #br# YANG Qiwei, REN Qilong

Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China

Received:2015-05-04 Revised:2015-05-30 Online:2015-08-05 Published:2015-08-05
Supported by:
supported by the National Natural Science Foundation of China (21222601), Program for New Century Excellent Talents in University of Ministry of Education of China (NCET-13-0524), and Zhejiang Key Scientific and Technological Innovation Team (2011R50002).

摘要/Abstract

摘要：

以油酸和豆甾醇为原料,研究了以硫酸氢钾-金属氧化物为组合的复合催化剂在酯化合成中的应用。首先,通过与其他硫酸盐的酯化效果进行比较,筛选出KHSO₄是适用于酯化合成中高效且安全的催化剂,并将其和不同的金属氧化物进行组合作为复合催化剂进一步探究酯化效果。通过实验结果比较,得到KHSO₄-ZnO作催化剂的酯化率最高。然后,将KHSO₄-ZnO作为复合催化剂,针对催化剂用量、反应温度、反应时间、酸醇摩尔比等因素进行考察,探究油酸和豆甾醇的最佳酯化条件。得到最佳工艺条件为:在通高纯氮气条件下,选用3.0%KHSO₄+1.0%ZnO(以豆甾醇的质量分数计)为催化剂,油酸和豆甾醇的摩尔比为1.8:1,反应的温度为 150℃,反应的时间为7 h,酯化率达到92.17%。本工艺利用KHSO₄-ZnO作为复合催化剂,得到较高的酯化率,实现了一条合成油酸豆甾醇酯的新工艺路线。

关键词: 复合催化剂, 金属氧化物, 硫酸氢钾, 酯化合成, 甾醇酯

Abstract:

Phytosteryl oleate synthesized from stigmasterol and oleic acid using the composite catalysts of potassium bisulfate and metal oxide was investigated. By comparing with other sulfates, potassium bisulfate was proved to be more suitable for the esterification of oleic acid and stigmasterol in an efficient and safe way. Taking into account the high catalytic efficiency of metal oxide, the combination of potassium bisulfate and different metal oxides as a kind of composite catalyst may be promising. The catalyst comparative experiments suggested that the composite catalyst of KHSO₄-ZnO was the best catalyst in terms of the esterification yields. When the esterification reaction was carried out at 150℃ for 7 h with oleic acid and stigmasterol in a molar ratio of 1.8:1 and 3.0% KHSO₄ + 1.0% ZnO catalyst (based on the mass of stigmasterol) under the protection of nitrogen, the highest esterification yield was 92.17%. In the presence of the composite catalyst of KHSO₄-ZnO, a new process for the synthesis of stigmasterol oleate with high esterification yield is acquired.

Key words: composite catalyst, metal oxide, potassium bisulfate, esterification, phytosteryl oleate

中图分类号:

TQ645.9⁺8

张硕, 杨亦文, 邢华斌, 苏宝根, 张治国, 鲍宗必, 杨启炜, 任其龙. 复合催化剂在油酸豆甾醇酯合成中的应用[J]. 化工学报, 2015, 66(8): 3078-3083.

ZHANG Shuo, YANG Yiwen, XING Huabin, SU Baogen, ZHANG Zhiguo, BAO Zongbi,
YANG Qiwei, REN Qilong. Synthesis of phytosteryl oleate using composite catalysts[J]. CIESC Journal, 2015, 66(8): 3078-3083.

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参考文献 39

[1] Fernandes P, Cabral J M S. Phytosterols: applications and recovery methods [J]. Bioresource Technology, 2007, 98: 2335-2350.

[2] Berger A, Jones P J H, Abumweis S S. Plant sterols: factors affecting their efficacy and safety as functional food ingredients [J]. Lipids Health Dis., 2004, 3: 5-23.

[3] Kritchevsky D, Chen S C. Phytosterol-health benefits and potential concerns: a review [J]. Nutr. Res., 2005, 25: 413-428.

[4] Institute of Food Science & Technology Trust Fund Information Statement. Phytosterol Esters (Plant Sterol and Stanol Esters). [ER/OL]. [2005-01]. http://www.ifst.org.

[5] Vuorio A F, Gylling H, Turtola H, et al. Stanol ester margarine alone and with simvastatin lowers serum cholesterol in families with familial hypercholesterolemia caused by the FH-North Karelia mutation [J]. Arterioscler Thromb. Vasc. Biol., 2000, 20 (2): 500-506.

[6] Mattson F H, Grundy S M, Crouse J R. Optimizing the effect of plant sterols on cholesterol absorption in man [J]. Am. J. Clin. Nutr., 1982, 35: 697-700.

[7] Kim J C, Kang B H, Shin C C, et al. Subchronic toxicity of plant sterol esters administered by gavage to Sprague-Dawley rats [J]. Food and Chemical Toxicology, 2002, 40: 1569-1580.

[8] Choi Y H, Kong K R, Kim Y A, et al. Induction of bax and activation of caspases during beta-sitosterol-mediated apoptosis in human colon cancer cells [J]. Int. J. Oncol., 2003, 23: 1657-1662.

[9] Nashed B, Yeganeh B, Hayglass K T, et al. Antiatherogenie effects of dietary plant sterols are associated with inhibition of proinflammatory cytokine production in Apo E-KO mice [J]. J. Nutr., 2005, 135: 2438-2444.

[10] Okoli C O, Akah P A. Mechanisms of the anti-inflammatory activity of the leaf extracts of Culcasia scandens P. Beau (Araceae) [J]. Pharmacol. Biochem. Behavior, 2004, 79: 473-481.

[11] Karppanen, et al. Food seasoning, food ingredients and food item compositions and methods for their preparation [P]: US, 6136349. 2000.

[12] David K, Shirley C C. Phytosterols-health benefits and potential concerns: a review [J]. Nutrition Research, 2005, 25: 413-428.

[13] Moreau R A, Whitaker B D, Hicks K B. Phytosterols, phytostanols, and their conjugates in foods:structural diversity, quantitative analysis, and health-promoting uses [J]. Progress in Lipid Research, 2002, 41: 457-500.

[14] He W S, Jia C S, Yang Y B, et al. Cholesterol-lowering effects of plant steryl and stanyl laurate by oral administration in mice [J]. Journal of Agricultural and Food Chemistry, 2011, 59: 5093-5099.

[15] Engel R, Schubert H. Formulation of phytosterols in emulsions for increased dose response in functional foods [J]. Innov. Food Sci. Emerging Technology, 2005, 6 (2): 233-237.

[16] Kevin B H, Robert A M. Phytosterols and phytostanols: functional food choleste rol busters [J]. Food technology, 2001, 55 (1): 63-67.

[17] Ryan C M,Wilson M A, Slavin J, et al.Associations between liver histology and severity of the metabolic syndrome in subjects with nonalcoholic fatty liver disease [J]. Diabetes Care, 2005, 28: 1222-1224.

[18] Richieri G V, Kleinfeld A M.Unbound free fatty acid levels in human serum [J]. J. Lipid Res. Feb., 1995, 36 (2):229-40.

[19] Moruisi K G, Oosthuizen W, Opperman A M. Phytosterols/stanols lower cholesterol concentrations in familial hypercholesterolemic subjects: a systematic review with meta-analysis [J]. Journal of the American College of Nutrition, 2006, 25: 41-48.

[20] He W S, Jia C S, Yang Y B, et al. Cholesterol-lowering effects of plant steryl and stanyl laurate by oral administration in mice [J]. Journal of Agricultural and Food Chemistry, 2011, 59: 5093-5099.

[21] Villeneuve P, Turon F, Caro Y, et al. Lipase-catalyzed synthesis of canola phytosterols oleate esters as cholesterol lowing agents [J]. Enzyme and Microbial Technology, 2005, 37: 150-155.

[22] Kim B H, Akoh C C. Modeling and optimization of lipase-catalyzed synthesis of phytosteryl esters of oleic acid by response surface methodology [J]. Food Chemistry, 2007, 102: 336-342.

[23] van Horn L, McCoin M, Kris-Etherton P M, Burke F, Carson J A S, Champagne C M, et al. The evidence for dietary prevention and treatment of cardiovascular disease [J]. Journal of the American Dietetic Association, 2008, 108:287-331.

[24] Plat J, Mensink R P. Plant stanol and sterol esters in the control of blood cholesterol levels: mechanism and safety aspects [J]. The American Journal of Cardiology, 2005, 96:15-22.

[25] Duchateau E A, G S M J E, Lin Y, Mel'nikov S M, et al. Proposed mechanisms of cholesterol-lowering action of plant sterols [J]. Eur. J.Lipid Sci. Technol., 2003, 105:171-185.

[26] Rozner S, Garti N. The activity and absorption relationship of cholesterol and phytosterols [J]. Colloids and Surfaces, 2006, 282/283: 435-456.

[27] Moghadasian M H, McManus B M, Godin D V, Rodrigues B, Frohlich J J. Proatherogenic and antiatherogenic effects of probucol and phytosterols in apolipoprotein E-deficient mice: possible mechanisms of action [J]. Journal of the American Heart Association, 1999, 99: 1733-1739.

[28] Bouic P J D. The role of phytosterols and phytosterolins in immune modulation: a review of the past 10 years [J]. Nutraceutics and Micronutrients, 2001, 4 (6): 471-475.

[29] van Rensburg S J, Daniels W M U, van Zyl J M, Taljaard J J F. A comparative study of the effects of cholesterol, beta-sitosterol, beta-sitosterol glucoside, dehydroepiandrosterone sulphate and melatonin on in vitro lipid peroxidation [J]. Metabolic Brain Disease, 2000, 15: 257-265.

[30] Yang Y B, He W S, Jia C S, et al. Efficient synthesis of phytosteryl esters using the Lewis acidic ionic liquid [J]. Journal of Molecular Catalysis A: Chemical, 2012, 357:39-43.

[31] Flickinger B D, Grabiel R, Poppe G. Methods for producing sterol ester-rich compositions [P]: US, 20050038270. 2005-02-17.

[32] Comelis W V O, Marnix P V A,Lourus C L. Method of manufacturing a sterol eater mixture [P]: US, 6492538. 2002-12-10.

[33] Mazzuca M, Miscoria S A, Rost E, et al. Fatty acids and sterol in seeds from wild species of berberis in argentine patagonia [J]. J. Argent. Chem. Soc., 2005, 93: 241-246.

[34] Meng X G, Pan Q Y, Yang T K. Synthesis of phytosteryl esters by using alumina-supported zinc oxide (ZnO/Al2O3) from esterification production of phytosterol with fatty acid [J]. J .Am. Oil Chem. Soc., 2011, 88: 143-149.

[35] Guo Tao (郭涛), Jiang Yuanrong (姜元荣), Wang Yong (王勇), et al. Preparation of phytosterolesters from phytosterol and fatty acid [J]. China Oils and Fats (中国油脂), 2011, 36 (1): 53-55.

[36] Pan Qiuyue (潘秋月), Zhou Xiaohong (周晓红), Meng Xianghe (孟祥河). Synthesis of phytosterol esters using solid green catalyst [J]. Journal of the Chinese Cereals and Oils Association (中国粮油学报), 2009, 24 (5): 115-118.

[37] Higgins Ⅲ J D. Preparation of sterol and stanol-esters [P]: US, 5892068. 1999-04-06.

[38] Higgins Ⅲ J D. Preparation of sterol and stanol-esters [P]: US, 6147236. 2000-11-14.

[39] Deng Q C, Zhang P, Huang Q D, et al. Chemical synthesis of phytosterol esters of polyunsaturated fatty acids with ideal oxidative stability [J]. European Journal of Lipid Science and Technology, 2011, 113 (4): 441-449.

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复合催化剂在油酸豆甾醇酯合成中的应用

Synthesis of phytosteryl oleate using composite catalysts

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[1]	Fernandes P, Cabral J M S. Phytosterols: applications and recovery methods [J]. Bioresource Technology, 2007, 98: 2335-2350.
[2]	Berger A, Jones P J H, Abumweis S S. Plant sterols: factors affecting their efficacy and safety as functional food ingredients [J]. Lipids Health Dis., 2004, 3: 5-23.
[3]	Kritchevsky D, Chen S C. Phytosterol-health benefits and potential concerns: a review [J]. Nutr. Res., 2005, 25: 413-428.
[4]	Institute of Food Science & Technology Trust Fund Information Statement. Phytosterol Esters (Plant Sterol and Stanol Esters). [ER/OL]. [2005-01]. http://www.ifst.org.
[5]	Vuorio A F, Gylling H, Turtola H, et al. Stanol ester margarine alone and with simvastatin lowers serum cholesterol in families with familial hypercholesterolemia caused by the FH-North Karelia mutation [J]. Arterioscler Thromb. Vasc. Biol., 2000, 20 (2): 500-506.
[6]	Mattson F H, Grundy S M, Crouse J R. Optimizing the effect of plant sterols on cholesterol absorption in man [J]. Am. J. Clin. Nutr., 1982, 35: 697-700.
[7]	Kim J C, Kang B H, Shin C C, et al. Subchronic toxicity of plant sterol esters administered by gavage to Sprague-Dawley rats [J]. Food and Chemical Toxicology, 2002, 40: 1569-1580.
[8]	Choi Y H, Kong K R, Kim Y A, et al. Induction of bax and activation of caspases during beta-sitosterol-mediated apoptosis in human colon cancer cells [J]. Int. J. Oncol., 2003, 23: 1657-1662.
[9]	Nashed B, Yeganeh B, Hayglass K T, et al. Antiatherogenie effects of dietary plant sterols are associated with inhibition of proinflammatory cytokine production in Apo E-KO mice [J]. J. Nutr., 2005, 135: 2438-2444.
[10]	Okoli C O, Akah P A. Mechanisms of the anti-inflammatory activity of the leaf extracts of Culcasia scandens P. Beau (Araceae) [J]. Pharmacol. Biochem. Behavior, 2004, 79: 473-481.
[11]	Karppanen, et al. Food seasoning, food ingredients and food item compositions and methods for their preparation [P]: US, 6136349. 2000.
[12]	David K, Shirley C C. Phytosterols-health benefits and potential concerns: a review [J]. Nutrition Research, 2005, 25: 413-428.
[13]	Moreau R A, Whitaker B D, Hicks K B. Phytosterols, phytostanols, and their conjugates in foods:structural diversity, quantitative analysis, and health-promoting uses [J]. Progress in Lipid Research, 2002, 41: 457-500.
[14]	He W S, Jia C S, Yang Y B, et al. Cholesterol-lowering effects of plant steryl and stanyl laurate by oral administration in mice [J]. Journal of Agricultural and Food Chemistry, 2011, 59: 5093-5099.
[15]	Engel R, Schubert H. Formulation of phytosterols in emulsions for increased dose response in functional foods [J]. Innov. Food Sci. Emerging Technology, 2005, 6 (2): 233-237.
[16]	Kevin B H, Robert A M. Phytosterols and phytostanols: functional food choleste rol busters [J]. Food technology, 2001, 55 (1): 63-67.
[17]	Ryan C M,Wilson M A, Slavin J, et al.Associations between liver histology and severity of the metabolic syndrome in subjects with nonalcoholic fatty liver disease [J]. Diabetes Care, 2005, 28: 1222-1224.
[18]	Richieri G V, Kleinfeld A M.Unbound free fatty acid levels in human serum [J]. J. Lipid Res. Feb., 1995, 36 (2):229-40.
[19]	Moruisi K G, Oosthuizen W, Opperman A M. Phytosterols/stanols lower cholesterol concentrations in familial hypercholesterolemic subjects: a systematic review with meta-analysis [J]. Journal of the American College of Nutrition, 2006, 25: 41-48.
[20]	He W S, Jia C S, Yang Y B, et al. Cholesterol-lowering effects of plant steryl and stanyl laurate by oral administration in mice [J]. Journal of Agricultural and Food Chemistry, 2011, 59: 5093-5099.
[21]	Villeneuve P, Turon F, Caro Y, et al. Lipase-catalyzed synthesis of canola phytosterols oleate esters as cholesterol lowing agents [J]. Enzyme and Microbial Technology, 2005, 37: 150-155.
[22]	Kim B H, Akoh C C. Modeling and optimization of lipase-catalyzed synthesis of phytosteryl esters of oleic acid by response surface methodology [J]. Food Chemistry, 2007, 102: 336-342.
[23]	van Horn L, McCoin M, Kris-Etherton P M, Burke F, Carson J A S, Champagne C M, et al. The evidence for dietary prevention and treatment of cardiovascular disease [J]. Journal of the American Dietetic Association, 2008, 108:287-331.
[24]	Plat J, Mensink R P. Plant stanol and sterol esters in the control of blood cholesterol levels: mechanism and safety aspects [J]. The American Journal of Cardiology, 2005, 96:15-22.
[25]	Duchateau E A, G S M J E, Lin Y, Mel'nikov S M, et al. Proposed mechanisms of cholesterol-lowering action of plant sterols [J]. Eur. J.Lipid Sci. Technol., 2003, 105:171-185.
[26]	Rozner S, Garti N. The activity and absorption relationship of cholesterol and phytosterols [J]. Colloids and Surfaces, 2006, 282/283: 435-456.
[27]	Moghadasian M H, McManus B M, Godin D V, Rodrigues B, Frohlich J J. Proatherogenic and antiatherogenic effects of probucol and phytosterols in apolipoprotein E-deficient mice: possible mechanisms of action [J]. Journal of the American Heart Association, 1999, 99: 1733-1739.
[28]	Bouic P J D. The role of phytosterols and phytosterolins in immune modulation: a review of the past 10 years [J]. Nutraceutics and Micronutrients, 2001, 4 (6): 471-475.
[29]	van Rensburg S J, Daniels W M U, van Zyl J M, Taljaard J J F. A comparative study of the effects of cholesterol, beta-sitosterol, beta-sitosterol glucoside, dehydroepiandrosterone sulphate and melatonin on in vitro lipid peroxidation [J]. Metabolic Brain Disease, 2000, 15: 257-265.
[30]	Yang Y B, He W S, Jia C S, et al. Efficient synthesis of phytosteryl esters using the Lewis acidic ionic liquid [J]. Journal of Molecular Catalysis A: Chemical, 2012, 357:39-43.
[31]	Flickinger B D, Grabiel R, Poppe G. Methods for producing sterol ester-rich compositions [P]: US, 20050038270. 2005-02-17.
[32]	Comelis W V O, Marnix P V A,Lourus C L. Method of manufacturing a sterol eater mixture [P]: US, 6492538. 2002-12-10.
[33]	Mazzuca M, Miscoria S A, Rost E, et al. Fatty acids and sterol in seeds from wild species of berberis in argentine patagonia [J]. J. Argent. Chem. Soc., 2005, 93: 241-246.
[34]	Meng X G, Pan Q Y, Yang T K. Synthesis of phytosteryl esters by using alumina-supported zinc oxide (ZnO/Al2O3) from esterification production of phytosterol with fatty acid [J]. J .Am. Oil Chem. Soc., 2011, 88: 143-149.
[35]	Guo Tao (郭涛), Jiang Yuanrong (姜元荣), Wang Yong (王勇), et al. Preparation of phytosterolesters from phytosterol and fatty acid [J]. China Oils and Fats (中国油脂), 2011, 36 (1): 53-55.
[36]	Pan Qiuyue (潘秋月), Zhou Xiaohong (周晓红), Meng Xianghe (孟祥河). Synthesis of phytosterol esters using solid green catalyst [J]. Journal of the Chinese Cereals and Oils Association (中国粮油学报), 2009, 24 (5): 115-118.
[37]	Higgins Ⅲ J D. Preparation of sterol and stanol-esters [P]: US, 5892068. 1999-04-06.
[38]	Higgins Ⅲ J D. Preparation of sterol and stanol-esters [P]: US, 6147236. 2000-11-14.
[39]	Deng Q C, Zhang P, Huang Q D, et al. Chemical synthesis of phytosterol esters of polyunsaturated fatty acids with ideal oxidative stability [J]. European Journal of Lipid Science and Technology, 2011, 113 (4): 441-449.

[1]	张永泉, 玄伟伟. 碱金属/（FeO+CaO+MgO）对硅酸盐灰熔渣结构和黏度的影响机理[J]. 化工学报, 2023, 74(4): 1764-1771.
[2]	黄心童, 耿宇昊, 刘恒源, 陈卓, 徐建鸿. 微流控制备新型功能纳米粒子研究进展[J]. 化工学报, 2023, 74(1): 355-364.
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