化工学报 ›› 2021, Vol. 72 ›› Issue (5): 2448-2464.DOI: 10.11949/0438-1157.20201355
收稿日期:
2020-09-25
修回日期:
2020-11-16
出版日期:
2021-05-05
发布日期:
2021-05-05
通讯作者:
马养民,强涛涛
作者简介:
郭林新(1990—),男,博士研究生,基金资助:
GUO Linxin1,2(),MA Yangmin3(
),QIANG Taotao1(
),REN Longfang1
Received:
2020-09-25
Revised:
2020-11-16
Online:
2021-05-05
Published:
2021-05-05
Contact:
MA Yangmin,QIANG Taotao
摘要:
植物单宁作为一种天然多酚类物质,广泛存在于多种植物的各组织部位中。单宁的结构复杂多样,含有大量的酚羟基、酯基、醚基等活性基团,可以和多种物质结合从而具有抗氧化、离子吸附及皮革鞣制等作用。这使得植物单宁这一功能材料,在医药加工、食品生产、污水处理等行业中应用广泛。然而天然的单宁类成分也存在着其结构上的固有不足之处,如分子量大、脂溶性差等。基于此,国内外的学者一直在探索寻找合适的单宁结构改性方法,从而改善单宁的渗透性、溶解性及反应活性等,使其能更加充分地用于工业生产中。以单宁的组成结构为基础,综述了近年来有关单宁的结构改性方法,并对其进行了展望,以期为单宁的结构修饰及高值化利用提供有益参考。
中图分类号:
郭林新, 马养民, 强涛涛, 任龙芳. 植物单宁的结构改性研究进展[J]. 化工学报, 2021, 72(5): 2448-2464.
GUO Linxin, MA Yangmin, QIANG Taotao, REN Longfang. Review on structure modification of plant tannins[J]. CIESC Journal, 2021, 72(5): 2448-2464.
1 | Dong L L, Mao Z J, Sun T. Condensed tannin effects on decomposition of very fine roots among temperate tree species[J]. Soil Biology and Biochemistry, 2016, 103: 489-492. |
2 | Sartori C J, Mota G S, Miranda I, et al. Tannin extraction and characterization of polar extracts from the barks of two Eucalyptus urophylla hybrids[J]. Bioresources, 2018, 13(3): 4820-4831. |
3 | Zhou Q, Rather L J, Ali A, et al. Environmental friendly bioactive finishing of wool textiles using the tannin-rich extracts of Chinese tallow (Sapium sebiferum L.) waste/fallen leaves[J]. Dyes and Pigments, 2020, 176: 108230. |
4 | Braga W L M, Roberto J A, Vaz C, et al. Extraction and optimization of tannin from the flower of Musa sp. applied to the treatment of iron ore dump[J]. Journal of Environmental Chemical Engineering, 2018, 6(4): 4310-4317. |
5 | Ping L, Pizzi A, Guo Z D, et al. Condensed tannins from grape pomace: characterization by FTIR and MALDI TOF and production of environment friendly wood adhesive[J]. Industrial Crops and Products, 2012, 40: 13-20. |
6 | Teng B, Hayasaka Y, Smith P A, et al. Effect of grape seed and skin tannin molecular mass and composition on the rate of reaction with anthocyanin and subsequent formation of polymeric pigments in the presence of acetaldehyde[J]. Journal of Agricultural and Food Chemistry, 2019, 67(32): 8938-8949. |
7 | Reuben U, Barminas J T, Aliyu B A, et al. The application of tannin extract from Anogeissus leiocarpus plant as wood adhesives[J]. International Journal of Biological and Chemical Sciences, 2014, 7(4): 1784-1793. |
8 | Pinto P C R, Sousa G, Crispim F, et al. Eucalyptus globulus bark as source of tannin extracts for application in leather industry[J]. ACS Sustainable Chemistry & Engineering, 2013, 1(8): 950-955. |
9 | Onem E, Gulumser G, Akay S, et al. Optimization of tannin isolation from acorn and application in leather processing[J]. Industrial Crops and Products, 2014, 53: 16-22. |
10 | Missio A L, Tischer B, dos Santos P S B, et al. Analytical characterization of purified mimosa (Acacia mearnsii) industrial tannin extract: single and sequential fractionation[J]. Separation and Purification Technology, 2017, 186: 218-225. |
11 | 闵凡芹, 张宗和, 秦清, 等. 负压空化法提取五倍子单宁酸的响应面法优化[J]. 天然产物研究与开发, 2013, 25(9): 1240-1244. |
Min F Q, Zhang Z H, Qin Q, et al. Optimization of vacuum cavitation extraction of tannic acid from Chinese gallnut using response surface method[J]. Natural Product Research and Development, 2013, 25(9): 1240-1244. | |
12 | Guo L X, Qiang T T, Ma Y M, et al. Optimisation of tannin extraction from Coriaria nepalensis bark as a renewable resource for use in tanning[J]. Industrial Crops and Products, 2020, 149: 112360. |
13 | Deepti B, Suyog G, Beautikuma S, et al. Tannin rich fraction of Punica granatum Linn. leaves ameliorates Freund's adjuvant induced arthritis in experimental animals[J]. Pharmacologia, 2014, 5(1): 19-31. |
14 | Park C G, Lee K C, Lee D W, et al. Effects of purified persimmon tannin and tannic acid on survival and reproduction of bean bug, Riptortus clavatus[J]. Journal of Chemical Ecology, 2004, 30(11): 2269-2283. |
15 | 公绪金, 李伟光, 张多英, 等. 负载金属捕获剂改性PAC吸附低温水中低浓度Cr(Ⅵ)特性[J]. 化工学报, 2012, 63(11): 3680-3687. |
Gong X J, Li W G, Zhang D Y, et al. Adsorption characteristics of metal-capture-agent immobilized PAC for low concentration Cr(Ⅵ) in water at low temperature[J]. CIESC Journal, 2012, 63(11): 3680-3687. | |
16 | 马贺伟, 廖学品, 王茹, 等. 皮胶原纤维固化单宁膜的制备及其对水溶液中铅和汞的吸附[J]. 化工学报, 2005, 56(10): 1907-1911. |
Ma H W, Liao X P, Wang R, et al. Immobilization of tannin on collagen fiber membrane and its adsorption to Pb(Ⅱ) and Hg(Ⅱ) in aqueous solution[J]. Journal of Chemical Industry and Engineering (China), 2005, 56(10): 1907-1911. | |
17 | Lacoste C, Čop M, Kemppainen K, et al. Biobased foams from condensed tannin extracts from Norway spruce (Picea abies) bark[J]. Industrial Crops and Products, 2015, 73: 144-153. |
18 | Pinela J, Prieto M A, Pereira E, et al. Optimization of heat- and ultrasound-assisted extraction of anthocyanins from Hibiscussabdariffa calyces for natural food colorants[J]. Food Chemistry, 2019, 275: 309-321. |
19 | Sánchez-Martín J, Beltrán-Heredia J, Delgado-Regaña A, et al. Optimization of tannin rigid foam as adsorbents for wastewater treatment[J]. Industrial Crops and Products, 2013, 49: 507-514. |
20 | Dutra R P, Abreu B V D B, Cunha M S, et al. Phenolic acids, hydrolyzable tannins, and antioxidant activity of geopropolis from the stingless bee Melipona fasciculata Smith[J]. Journal of Agricultural and Food Chemistry, 2014, 62(12): 2549-2557. |
21 | Maier M, Oelbermann A L, Renner M, et al. Screening of European medicinal herbs on their tannin content—new potential tanning agents for the leather industry[J]. Industrial Crops and Products, 2017, 99: 19-26. |
22 | Cai Y Z, Xing J, Sun M, et al. Phenolic antioxidants (hydrolyzable tannins, flavonols, and anthocyanins) identified by LC-ESI-MS and MALDI-QIT-TOF MS from Rosa chinensis flowers[J]. Journal of Agricultural and Food Chemistry, 2005, 53(26): 9940-9948. |
23 | 张亮亮, 汪咏梅, 徐曼, 等. 植物单宁化学结构分析方法研究进展[J]. 林产化学与工业, 2012, 32(3): 107-116. |
Zhang L L, Wang Y M, Xu M, et al. Research progress in analytical methods of vegetable tannins[J]. Chemistry and Industry of Forest Products, 2012, 32(3): 107-116. | |
24 | 贾喜庆, 姚庆达, 杨义清, 等. 植物鞣剂的结构、改性及其在制革中的应用[J]. 西部皮革, 2018, 40(21): 35-42. |
Jia X Q, Yao Q D, Yang Y Q, et al. Structure, modification of vegetable tannins and its application in tanning[J]. West Leather, 2018, 40(21): 35-42. | |
25 | 李冬冬, 蔡超, 杨萌, 等. 基于单宁酸的功能材料研究进展[J]. 高分子通报, 2017, (9): 10-20. |
Li D D, Cai C, Yang M, et al. Progress in the application of tannic acid to the functional materials[J]. Polymer Bulletin, 2017, (9): 10-20. | |
26 | Quideau S, Deffieux D, Douat-Casassus C, et al. Plant polyphenols: chemical properties, biological activities, and synthesis[J]. Angewandte Chemie International Edition, 2011, 50(3): 586-621. |
27 | Andjelković M, van Camp J, De Meulenaer B, et al. Iron-chelation properties of phenolic acids bearing catechol and galloyl groups[J]. Food Chemistry, 2006, 98(1): 23-31. |
28 | 石碧, 狄莹. 植物多酚[M]. 北京: 科学出版社, 2000: 105-111. |
Shi B, Di Y. Vegetable Polyphenol [M]. Beijing: Science Press, 2000: 105-111. | |
29 | Yamaguchi H, Yoshino K, Kido A. Termite resistance and wood-penetrability of chemically modified tannin and tannin-copper complexes as wood preservatives[J]. Journal of Wood Science, 2002, 48(4): 331-337. |
30 | Qiang T T, Chen L, Zhang Q, et al. A sustainable and cleaner speedy tanning system based on condensed tannins catalyzed by laccase[J]. Journal of Cleaner Production, 2018, 197: 1117-1123. |
31 | Cateto C A, Barreiro M F, Rodrigues A E, et al. Optimization study of lignin oxypropylation in view of the preparation of polyurethane rigid foams[J]. Industrial & Engineering Chemistry Research, 2009, 48(5): 2583-2589. |
32 | Sadeghifar H, Cui C Z, Argyropoulos D S. Toward thermoplastic lignin polymers(Part 1): Selective masking of phenolic hydroxyl groups in kraft lignins via methylation and oxypropylation chemistries[J]. Industrial & Engineering Chemistry Research, 2012, 51(51): 16713-16720. |
33 | García D E, Glasser W G, Pizzi A, et al. Hydroxypropyl tannin derivatives from Pinus pinaster (Ait.) bark[J]. Industrial Crops and Products, 2013, 49: 730-739. |
34 | García D E, Glasser W G, Pizzi T A, et al. Synthesis and physicochemical properties of hydroxypropyl tannins from maritime pine bark (Pinus pinaster Ait.)[J]. Holzforschung, 2014, 68(4): 411-418. |
35 | Jahanshahi S, Pizzi A, Abdulkhani A, et al. MALDI-TOF, 13C NMR and FT-MIR analysis and strength characterization of glycidyl ether tannin epoxy resins[J]. Industrial Crops and Products, 2016, 83: 177-185. |
36 | Zhang S J, Ji Y L, Ao F J, et al. Selective adsorption of Au(Ⅲ) from aqueous solution using 2, 5‑dimercapto‑1, 3, 4‑thiadiazole modified persimmon tannin[J]. Journal of the Brazilian Chemical Society, 2018, 29(7):1487-1498. |
37 | Grigsby W, Bridson J, Lomas C, et al. Esterification of condensed tannins and their impact on the properties of poly(lactic acid)[J]. Polymers, 2013, 5(2): 344-360. |
38 | Gaugler M, Grigsby W J. Thermal degradation of condensed tannins from Radiata pine bark[J]. Journal of Wood Chemistry and Technology, 2009, 29(4): 305-321. |
39 | Luo C H, Grigsby W, Edmonds N, et al. Synthesis, characterization, and thermal behaviors of tannin stearates prepared from quebracho and pine bark extracts[J]. Journal of Applied Polymer Science, 2010, 117(1): 352-360. |
40 | Bridson J H, Grigsby W J, Main L. Synthesis and characterization of flavonoid laurate esters by transesterification[J]. Journal of Applied Polymer Science, 2013, 129(1): 181-186. |
41 | Grigsby W J, Bridson J H, Lomas C, et al. Evaluating modified tannin esters as functional additives in polypropylene and biodegradable aliphatic polyester[J]. Macromolecular Materials and Engineering, 2014, 299(10): 1251-1258. |
42 | Grigsby W J, Bridson J H, Schrade C. Modifying biodegradable plastics with additives based on condensed tannin esters[J]. Journal of Applied Polymer Science, 2015, 132(11): 41626-41629. |
43 | 段文贵, 耿哲, 张加研, 等. 改性松香-缩合单宁酯的制备及性质[J]. 林产化学与工业, 2009, 29(3): 6-12. |
Duan W G, Geng Z, Zhang J Y, et al. Preparation and properties of modified rosin-condensed tannins esters[J]. Chemistry and Industry of Forest Products, 2009, 29(3): 6-12. | |
44 | 邢其毅, 裴伟伟, 徐瑞秋. 基础有机化学 [M]. 北京: 北京大学出版社, 2017: 818-819. |
Xing Q Y, Pei W W, Xu R Q. Basic Organic Chemistry [M]. Beijing: Peking University Press, 2017: 818-819. | |
45 | 杨丹丹, 陈中兴. 天然水处理剂单宁的改性及性能研究[J]. 华东理工大学学报, 2001, 27(4): 388-391. |
Yang D D, Chen Z X. Preparation and evaluation of modified tannin[J]. Journal of East China University of Science and Technology, 2001, 27(4): 388-391. | |
46 | Tambi L, Frediani P, Frediani M, et al. Hide tanning with modified natural tannins[J]. Journal of Applied Polymer Science, 2008, 108(3): 1797-1809. |
47 | 蒋廷方, 唐一果, 廖华. 冷杉栲胶的接枝改性及其应用的研究[J]. 皮革科技, 1984, 13(10): 5-9, 34. |
Jiang Y F, Tang Y G, Liao H. Study on graft modification of fir tannin extract and its application[J]. Leather Science and Technology, 1984, (10): 5-9, 34. | |
48 | 汪建根, 杨宗邃, 马建中, 等. 接枝改性橡椀栲胶的性能及其应用[J]. 中国皮革, 2002, 31(19):1-5. |
Wang J G, Yang Z S, Ma J Z, et al. Properties and application of graft modified valex extract[J]. China Leather, 2002, 31(19):1-5. | |
49 | 汪建根, 杨宗邃, 马建中, 等. 橡椀栲胶接枝改性的研究[J]. 中国皮革, 1998, 27(7): 9-11. |
Wang J G, Yang Z S, Ma J Z, et al. Study on graft modification of valonea extract[J]. China Leather, 1998, 27(7): 9-11. | |
50 | Barbosa V, Ramires E C, Razera I A T, et al. Biobased composites from tannin-phenolic polymers reinforced with coir fibers[J]. Industrial Crops and Products, 2010, 32(3): 305-312. |
51 | Ramires E C, Frollini E. Tannin-phenolic resins: synthesis, characterization, and application as matrix in biobased composites reinforced with sisal fibers[J]. Composites Part B: Engineering, 2012, 43(7): 2851-2860. |
52 | Bello A, Virtanen V, Salminen J P, et al. Aminomethylation of spruce tannins and their application as coagulants for water clarification[J]. Separation and Purification Technology, 2020, 242: 116765. |
53 | Li X J, Wang Z M, Ning J L, et al. Preparation and characterization of a novel polyethyleneimine cation-modified persimmon tannin bioadsorbent for anionic dye adsorption[J]. Journal of Environmental Management, 2018, 217: 305-314. |
54 | Kim Y H, Alam M N, Marutani Y, et al. Improvement of Pd(Ⅱ) adsorption performance of condensed-tannin gel by amine modification[J]. Chemistry Letters, 2009, 38(10): 956-957. |
55 | Gurung M, Adhikari B B, Kawakita H, et al. Selective recovery of precious metals from acidic leach liquor of circuit boards of spent mobile phones using chemically modified persimmon tannin gel[J]. Industrial & Engineering Chemistry Research, 2012, 51(37): 11901-11913. |
56 | Morisada S, Kim Y H, Ogata T, et al. Improved adsorption behaviors of amine-modified tannin gel for palladium and platinum ions in acidic chloride solutions[J]. Industrial & Engineering Chemistry Research, 2011, 50(4): 1875-1880. |
57 | Gurung M, Adhikari B B, Morisada S, et al. N-aminoguanidine modified persimmon tannin: a new sustainable material for selective adsorption, preconcentration and recovery of precious metals from acidic chloride solution[J]. Bioresource Technology, 2013, 129: 108-117. |
58 | Morisada S, Rin T, Ogata T, et al. Adsorption recovery of rhodium(Ⅲ) in acidic chloride solutions by amine-modified tannin gel[J]. Journal of Applied Polymer Science, 2012, 126(S2): E34-E38. |
59 | Yi Q P, Fan R Y, Xie F, et al. Selective recovery of Au(Ⅲ) and Pd(Ⅱ) from waste PCBs using ethylenediamine modified persimmon tannin adsorbent[J]. Procedia Environmental Sciences, 2016, 31: 185-194. |
60 | Wang L, Liang W Y, Yu J, et al. Flocculation of Microcystis aeruginosa using modified larch tannin[J]. Environmental Science & Technology, 2013, 47(11): 5771-5777. |
61 | Wang X Y, Zhao Y, Jiang X X, et al. The growth and physiological activity of Microcystis aeruginosa after flocculation using modified tannin[J]. International Biodeterioration & Biodegradation, 2018, 133: 180-186. |
62 | Shi Z Q, Yang Q L, Kuga S, et al. Dissolution of wood pulp in aqueous NaOH/urea solution via dilute acid pretreatment[J]. Journal of Agricultural and Food Chemistry, 2015, 63(27): 6113-6119. |
63 | Li J J, Zhang A B, Zhang S F, et al. Larch tannin-based rigid phenolic foam with high compressive strength, low friability, and low thermal conductivity reinforced by cork powder[J]. Composites Part B: Engineering, 2019, 156: 368-377. |
64 | Mouls L, Fulcrand H. Identification of new oxidation markers of grape-condensed tannins by UPLC-MS analysis after chemical depolymerization[J]. Tetrahedron, 2015, 71(20): 3012-3019. |
65 | Liu J, Wang L L, Li J J, et al. Degradation mechanism of Acacia mangium tannin in NaOH/urea aqueous solution and application of degradation products in phenolic adhesives[J]. International Journal of Adhesion and Adhesives, 2020, 98: 102556. |
66 | Peres R S, Armelin E, Alemán C, et al. Modified tannin extracted from black wattle tree as an environmentally friendly antifouling pigment[J]. Industrial Crops and Products, 2015, 65: 506-514. |
67 | Banerjee R, Mukherjee G, Patra K C. Microbial transformation of tannin-rich substrate to gallic acid through co-culture method[J]. Bioresource Technology, 2005, 96(8): 949-953. |
68 | Mukherjee G, Banerjee R. Biosynthesis of tannase and gallic acid from tannin rich substrates by Rhizopus oryzae and Aspergillus foetidus[J]. Journal of Basic Microbiology, 2004, 44(1): 42-48. |
69 | 宋立江, 杜光伟, 狄莹, 等. 落叶松栲胶高度亚硫酸化改性及其产物应用性质的研究[J]. 林产化学与工业, 1999, 19(4): 1-6. |
Song L J, Du G W, Di Y, et al. Modification of larch bark tannin extract by intensive sulfitation[J]. Chemistry and Industry of Forest Products, 1999, 19(4): 1-6. | |
70 | 石碧, 狄莹, 宋立江, 等. 栲胶的化学改性及其产物在无铬少铬鞣法中的应用[J]. 中国皮革, 2001, 30(9): 3-8. |
Shi B, Di Y, Song L J, et al. Chemical modifications of vegetable extracts and applications of the products in chrome-free and chrome-reduced tannages[J]. China Leather, 2001, 30(9): 3-8. | |
71 | 田金平, 陈武勇, 陈萍, 等. 栲胶改性做中和复鞣剂的研究[J]. 皮革化工, 1999, 16(5): 14-18. |
Tian J P, Chen W Y, Chen P, et al. Studies on modification of vegetable tannin as neutralizing retanning agent[J]. Leather Chemicals, 1999, 16(5): 14-18. | |
72 | 陈武勇, 陈发奋, 田金平. 毛杨梅栲胶重度亚硫酸化改性与应用研究[J]. 林产化学与工业, 2002, 22(4): 55-58. |
Chen W Y, Chen F F, Tian J P. Modified myrtan tannin extract by intensive sulfitation as a neutralizer for leather[J]. Chemistry & Industry of Forest Products, 2002, 22(4): 55-58. | |
73 | 陈武勇, 王应红, 陈继平. 铬-橡椀复鞣剂的制备及应用研究[J]. 中国皮革, 2005, 34(17): 20-22, 29. |
Chen W Y, Wang Y H, Chen J P. Preparation and application of chrome-valonia tannin retanning agent[J]. China Leather, 2005, 34(17): 20-22, 29. | |
74 | Li Y, Luo X G, Liu Z, et al. Adsorption and deposition of Cu(Ⅱ) on modified valonia tannin[J]. Materials Science Forum, 2009, 620/621/622: 555-558. |
75 | Wang Z M, Gao M M, Li X J, et al. Efficient adsorption of methylene blue from aqueous solution by graphene oxide modified persimmon tannins[J]. Materials Science and Engineering: C, 2020, 108: 110196. |
76 | Li X J, Wang Z M, Liang H J, et al. Chitosan modification persimmon tannin bioadsorbent for highly efficient removal of Pb(Ⅱ) from aqueous environment: the adsorption equilibrium, kinetics and thermodynamics[J]. Environmental Technology, 2019, 40(1): 112-124. |
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摘要 870
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