佳乐麝香的合成研究
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摘要
佳乐麝香是一种多环麝香,香气浓郁、细腻,很接近大环麝香的香韵,且理化性质稳定,价格又比较低廉,可以广泛应用于香水、香精、化妆品、食品、医药等领域,是很有发展前途的合成麝香品种。
本文以α-甲基苯乙烯(AMS)、叔戊醇、环氧丙烷、多聚甲醛为原料,采用三步法合成佳乐麝香:先AMS和叔戊醇在酸性催化剂的条件下发生缩合反应,生成的产物五甲基茚满与环氧丙烷发生羟异丙基化反应,生成的六甲基茚满醇再与聚甲醛发生醇醛半缩合反应,经缩合环化得到最终产品。各步产物经IR,UV-Vis表征验证。
在合成茚满实验中,通过单因素实验讨论了催化剂种类与用量、反应温度、反应时间、反应物料比等反应因素对合成反应的影响;通过正交实验优化了工艺条件:当n(AMS)∶n(H3PO4)∶n(叔戊醇):n(H2O)= 1.00∶0.85∶1.15:0.85,在35℃下反应6h。收率可达59.7%。
在合成茚满醇时,通过单因素实验讨论了溶剂种类和用量、反应物料比、催化剂用量、反应温度、反应时间等反应因素对合成反应的影响;通过正交实验优化了工艺条件:当n(CH2Cl2)∶n(茚满)∶n(环氧丙烷)∶n(AlCl3)=10∶0.93∶1.00∶0.87,在-20～-15℃循环反应5h。收率可达62.7%。
最后在合成佳乐麝香中,通过单因素实验讨论了催化剂种类和用量、聚甲醛用量、反应温度、反应时间和碱环化时间等反应因素对合成反应的影响;通过正交实验优化了工艺条件:当n(CH2Cl2)∶n(茚满醇)∶n(甲醛)∶n(PCl5):n(H2O)=2.90∶1.00∶1.32∶0.95:9.5,在40℃下反应6h,碱环化60min。收率可达98.2%。
该工艺选择了更合理的催化剂和溶剂,改善了现有工艺,减少了“三废”污染和设备腐蚀问题,同时提高收率、降低成本。
Galaxolide as one kind of the polycyclic musk, which have strong, comfortable and similar to macrocyclic musk's fragrances, is broadly used in many fields, such as perfume, cosmetic, food, medicines and etc. And galaxolide possesses simple production methods, stable physical and chemical properties, and low cost price. So it has rather competitive edge and is the most promising among the synthetical musk.
There presents the preparation of the three steps to galaxolide in this paper. First, the indene was synthesized by the condensation with AMS and tert-amyl alcohol under condition of acidic catalyst. And then the indanol was obtained through the OH-isopropylation with the indene and propylene oxide as the materials. Finally, galaxolide was synthesized through the condensation and cyclization using the indanol and polyformaldehyde, and acid as the catalyst. All the products were confirmed by IR and UV-Vis spectra.
Through single-factor experiments, some factors have been analyzed on the reaction of synthesizing indene, including the kinds and dosage of catalyst, the action temperature, the action time and the materiel ratio. And through orthogonal experiment method, the optimum technologic condition of the process is the molar ratio of n(AMS)∶n(H3PO4)∶n(tert-amyl alcohol):n(H2O)= 1.00∶0.85∶1.15:0.85, at 35℃for 6 h. and the yield of indene was up to 59.7%.
Some factors have been investigated on the synthesis of indanol by the single-factor studies, including the kinds and dosage of solvent, the dosage of catalyst, the action temperature, the action time and the materiel ratio. And through orthogonal experiment method, the optimum technologic condition of the process is the molar ratio of n(CH2Cl2)∶n(indene)∶n(propylene oxide)∶n(AlCl3)=10∶0.93∶1.00∶0.87, between -20℃and -15℃for 6 h, and the yield of indene is up to 62.7%. During the preparation of galaxolide, last, some factors had been analyzed, including the kinds and dosage of catalyst, the action temperature, the action time and the materiel ratio, through the single-factor experiments. And through orthogonal experiment method, the optimum technologic condition of the process is the molar ratio of n(CH2Cl2)∶n(indanol)∶n(formaldehyde)∶n(PCl5):n(H2O)=2.90∶1.00∶1.32∶0.95:9.5, at 40℃for 6 h and alkaline cyclization for 60min. And the yield of galaxolide was up to 98.2%
The synthesis method of galaxolide was improved and opted for a more rational solvent and catalyst, reducing the problems of pollution and corrosion, while it increased the yield but reduced the costs.
本文以α-甲基苯乙烯(AMS)、叔戊醇、环氧丙烷、多聚甲醛为原料,采用三步法合成佳乐麝香:先AMS和叔戊醇在酸性催化剂的条件下发生缩合反应,生成的产物五甲基茚满与环氧丙烷发生羟异丙基化反应,生成的六甲基茚满醇再与聚甲醛发生醇醛半缩合反应,经缩合环化得到最终产品。各步产物经IR,UV-Vis表征验证。
在合成茚满实验中,通过单因素实验讨论了催化剂种类与用量、反应温度、反应时间、反应物料比等反应因素对合成反应的影响;通过正交实验优化了工艺条件:当n(AMS)∶n(H3PO4)∶n(叔戊醇):n(H2O)= 1.00∶0.85∶1.15:0.85,在35℃下反应6h。收率可达59.7%。
在合成茚满醇时,通过单因素实验讨论了溶剂种类和用量、反应物料比、催化剂用量、反应温度、反应时间等反应因素对合成反应的影响;通过正交实验优化了工艺条件:当n(CH2Cl2)∶n(茚满)∶n(环氧丙烷)∶n(AlCl3)=10∶0.93∶1.00∶0.87,在-20～-15℃循环反应5h。收率可达62.7%。
最后在合成佳乐麝香中,通过单因素实验讨论了催化剂种类和用量、聚甲醛用量、反应温度、反应时间和碱环化时间等反应因素对合成反应的影响;通过正交实验优化了工艺条件:当n(CH2Cl2)∶n(茚满醇)∶n(甲醛)∶n(PCl5):n(H2O)=2.90∶1.00∶1.32∶0.95:9.5,在40℃下反应6h,碱环化60min。收率可达98.2%。
该工艺选择了更合理的催化剂和溶剂,改善了现有工艺,减少了“三废”污染和设备腐蚀问题,同时提高收率、降低成本。
Galaxolide as one kind of the polycyclic musk, which have strong, comfortable and similar to macrocyclic musk's fragrances, is broadly used in many fields, such as perfume, cosmetic, food, medicines and etc. And galaxolide possesses simple production methods, stable physical and chemical properties, and low cost price. So it has rather competitive edge and is the most promising among the synthetical musk.
There presents the preparation of the three steps to galaxolide in this paper. First, the indene was synthesized by the condensation with AMS and tert-amyl alcohol under condition of acidic catalyst. And then the indanol was obtained through the OH-isopropylation with the indene and propylene oxide as the materials. Finally, galaxolide was synthesized through the condensation and cyclization using the indanol and polyformaldehyde, and acid as the catalyst. All the products were confirmed by IR and UV-Vis spectra.
Through single-factor experiments, some factors have been analyzed on the reaction of synthesizing indene, including the kinds and dosage of catalyst, the action temperature, the action time and the materiel ratio. And through orthogonal experiment method, the optimum technologic condition of the process is the molar ratio of n(AMS)∶n(H3PO4)∶n(tert-amyl alcohol):n(H2O)= 1.00∶0.85∶1.15:0.85, at 35℃for 6 h. and the yield of indene was up to 59.7%.
Some factors have been investigated on the synthesis of indanol by the single-factor studies, including the kinds and dosage of solvent, the dosage of catalyst, the action temperature, the action time and the materiel ratio. And through orthogonal experiment method, the optimum technologic condition of the process is the molar ratio of n(CH2Cl2)∶n(indene)∶n(propylene oxide)∶n(AlCl3)=10∶0.93∶1.00∶0.87, between -20℃and -15℃for 6 h, and the yield of indene is up to 62.7%. During the preparation of galaxolide, last, some factors had been analyzed, including the kinds and dosage of catalyst, the action temperature, the action time and the materiel ratio, through the single-factor experiments. And through orthogonal experiment method, the optimum technologic condition of the process is the molar ratio of n(CH2Cl2)∶n(indanol)∶n(formaldehyde)∶n(PCl5):n(H2O)=2.90∶1.00∶1.32∶0.95:9.5, at 40℃for 6 h and alkaline cyclization for 60min. And the yield of galaxolide was up to 98.2%
The synthesis method of galaxolide was improved and opted for a more rational solvent and catalyst, reducing the problems of pollution and corrosion, while it increased the yield but reduced the costs.
引文
[1]林翔云.香料史话(上)[J].国内外香化信息, 2008,(04)
[2]汪秋安.中国古近代香料史初探[J].香料香精化妆品, 1999,(02)
[3]杨峻山,赵杨景.加速对药用植物的研究发展具有我国特色的药学事业[J].资源节约和综合利用, 1995,(01)
[4]柴素芬.药用植物在化妆品中的应用[J].广东科技, 1999,(08)
[5]葛传吉.药用植物在化妆品中的应用[J].山东中医杂志, 2005,(12)
[6] Roman Holubowicz, Magdalena Frackowiak,张佐双,张本刚,刘洋.波兰药用植物生产概况[J].中国现代中药, 2007,(04)
[7]王金陵.在《东北地区药用植物图志》审稿会上的讲话[J].国土与自然资源研究, 1982,(01)
[8]甘炳春,李榕涛.海南药用植物资源状况及其保护[J].国土与自然资源研究, 2005,(02)
[9]李英.药用植物与环境卫生[J].绿化与生活, 2001,(05)
[10]五分之一的药用植物面临灭绝[J].中国中医药信息杂志, 2004,(02)
[11]林翔云.香料史话(下)[J].国内外香化信息, 2008,(05)
[12]颜伟.用于食品的合成香料[J].食品工业科技, 1985,(02)
[13]李明.重视合成香料的发展[J].浙江化工, 1983,(02)
[14]石方.合成香料[J].现代化工, 1983,(01)
[15]日本合成香料的十年(一)[J].国内外香化信息, 2007,(09)
[16]陈景茹.国内香料工业发展概况[J].应用化工, 1984,(01)
[17]张意宽.合成香料十年概况[J].精细化工, 1988,(06)
[18]黄致喜.中国大百科全书精细化工部分选登[J].精细与专用化学品, 1987,(08)
[19]呋喃基环缩醛类合成香料[J].安徽化工, 1987,(04)
[20]陈丽珍.日推出2种新型合成香料[J].精细与专用化学品, 1992,(04)
[21]巩江,倪士峰,骆蓉芳,任艳萍,吴一飞,赵桂仿.食用香料成分研究进展[J].中国调味品, 2009,(03)
[22]胡勤裕,田如芬.近年来国外食用香料的发展动态及展望[J].食品与发酵工业, 1980,(02)
[23]王立军.食用香料贸易漫淡[J].国际市场, 1996,(03)
[24]范军.江苏省涂料工业技术进展(1995～1996年度)[J].江苏化工, 1997,(04)
[25]舒宏福.食用香料中的长效和耐高温香料[J].香料香精化妆品, 2005,(01)
[26] Firmenich建成食用香料技术中心[J].国内外香化信息, 2002,(03)
[27]张建梅.重金属废水处理技术研究进展(综述)[J].西安联合大学学报, 2003,(02)
[28]唐伟家. 1996年度江苏省石油化工技术进展[J].江苏化工, 1997,(03)
[29]孔岩,黎植昌,刘治中,蒲涛.氨基酸类农药的研究与进展[J].西南师范大学学报(自然科学版) , 1999,(03)
[30]雷得漾.对开发我省食用香料工业的几点看法[J].精细化工中间体, 1986,(02)
[31]香精香料知识问答(九)[J].国内外香化信息, 2009,(02)
[32]香精香料知识问答(十)[J].国内外香化信息, 2009,(03)
[33]香精香料知识问答(八)[J].国内外香化信息, 2009,(01)
[34]曾智勇.重要中间体CA的合成方法与工艺路线概况[J].精细化工中间体, 1988,(04)
[35]冯传启. KICl_4合成方法的改进[J].化学试剂, 1994,(04)
[36]陈竹雯.“Best Synthetic Methods”《最佳合成方法》[J].大学化学, 1988,(02)
[37]尚岩,王春颖.氨基酸酯合成方法最新研究进展[J].哈尔滨理工大学学报, 2008,(02)
[38]徐尚成.噻螨酮及其中间体的合成方法[J].农药, 1989,(01)
[39]王献钊,刘明娣.阿魏酸及阿魏酸乙酯的合成[J].湖南城市学院学报(自然科学版) , 2007,(04)
[40]李宗成.拟除虫菊酯杀虫剂的合成[J].农药, 1983,(03)
[41]思源.哥伦布的香料迷途[J].海洋世界, 2008,(02)
[42]严小青,惠富平.郑和下西洋与明代香料朝贡贸易[J].江海学刊, 2008,(01)
[43] Karen J.R.,Structuere-odor relationships[J]. Chem.Rev.,1996,96:3201~3240
[44]王天民,天然麝香与合成麝香[J].上海轻工业,1996,2:30~33
[45] Reynold C.,Fuson J.,Mills T.,The structure of musk ketone and musk tibetene[J]. J. Org.Chem., 1947,12(4):587~595
[46] Bauer K.;Garbe D.,Common fragrance and flavor materials:preparation,properties and uses[J]. Deerfield Beach:VCH Publishers,1985,40~58
[47] Lauren Barbetta.,Musk aroma chemical industry[J]. erf.&Flav.,1987,6(13):60~67
[48]董万超,赵伟刚,刘春华,麝香研究进展[J].特产研究,2001,2:48~58
[49] Geog F.,Jerry A.B.,Phillp K.,Fragrance chemistry[J]. Tetrahedron,1998,54:7633~7703
[50] Ruzicka M.,Schinz H.,A new method for the synthesis of macrocyclic ketones[J]. Helv.Chim.Acta., 1926,9:715~718
[51] Eugene G.H.,West C.O.,Progress for improving the fragrance properties ofmacrocyclic compounds obtained by thermal polymerization[P]. US,4331603,1982-03-25
[52] Arctander S.,Perfume and flavor chemicals(aroma chemicals) [J]. Las Vegas:Steffen Arctander's Publications,1969
[53]李宏,调香中的天然和合成麝香[J].四川日化,1993,4:62~67
[54] MtUler P.M.,Lamparsky D.,Perfumes:,art,science and technology[J]. London:Elsevier Applied Science,1991
[55] Elisabetta B.,Claudio F.,Stefano S.,Enantioselective perception of chiral odorants[J]. Asymm.,2003,14:1~42
[56] Akira L.,Manufacturing of microcylic musk compound from long-chaindicarboxylic acid[J]. Flav. Frag.J.,1987,15(4):161~164
[57] Jingjiang L.,Guilin D.,Common structural characteristics of musk ordorant molecules[J]. J.Mol.Struc.(Theoch),1998,2(432):97~103
[58] Api A.M.,Ford R.A.,San R.H.,An evaluation of musk xylene in a battery of genotoxicity tests[J]. Food Chem.&Toxol.,1995,33(12):1039~1045
[59] Xiaoming Z.,Wolfgang S.,Photochemical behavior of musk ambrette[J]. Chemosphere, 1999,39(1):11~21
[60] Severin M.,Peter S.,Christian S.,Occurrence of nitro and non-nitro benzenoid musk compounds in human adipose tissu[J]. e, Chemosphere,1996,33(1):17~28
[61] Gerhard G.R.,Manfred W.,Nitro musk fragrances in biota from freshwater and marine environment[J]. Chemosphere,1995,30(4):641~651
[62] Peck A.M.,Hornbuckle K.C.,Synthetic musk fragrances in lake Michigan[J], Environ.Sci.Technol.,2004,38(2):367~372
[63] Kai B.,Heinrich H.,Wilfried L.,Results of non target screening of lipophilic organic pollutants in the German bight II:polycyclic musk fragrances[J], Water Research,1998,32(6):1857-1863
[64] Martin C.,Moeder M.,Daniel X.,Biotransformation of the polycyclic musks HHCB and AHTN and metabolite formation by fungi occurring in freshwater environments[J], Environ.Sci.Technol.,2007,41(15):5395~5402
[65] Gerhard G.R.,Polycyclic musk fragrances in the aquatic environment[J]. Toxicol.Lett., 1999,11(1):37~56
[66] Philip G.S.,American musk.IV.on the biological origin of animal musk.Two more largeting ketones from the muskra[J]. t, J.Am.Chem.Soc.,1945,67(6):907-909.
[67] Antonius J.A.,Van D.W.,Ian M.P.,Macrocyclic musk mixtures[P].US,6103679,2000-08-15
[68] Lilianne A.Z.,Premysl S.,Macrocyclic musk compounds—an absence of genotoxicity in the ames test and the in vivo micronucleus assay[J]. Toxicol.Lett.,2002,135(1):155~163
[69]舒宏福,麝香类香料的开发及安全环保问题[J].精细化工,1999,16:311~315
[70]胡勤裕,田如芬.近年来国外食用香料的发展动态及展望[J].食品与发酵工业, 1980,(02)
[71]浅井治海.香料合成技术的发展[J].香料. 1999,(2):99-103
[72] Philip. Kraft.‘Brain Aided’Musk Design[J]. Chemistry and Biodiversity, 2004(1):1957
[73] Philip. Kraft. Aroma chemicals IV: Musks[J]. Chemistry and Technology of Flavours and Fragrances, 2005: 143-168.
[74]张高勇.日用化学品[M].北京:化学工业出版社,1999
[75] Lambertus G. Heerlnga . New Trieydic Isochromans with Musk Odour [P]. Great Britain Patent, 99l146, May. 1965
[76] Gerald J. Ferber . Production of Indanes [P]. United States Patent, Field of Search . 4440966, Apr. 1984
[77] Ferber , Gerald John . Process for the Production of Indanes [P]. European Patent, 0061267, Sept. 1982
[78]刘树文.三环异色满型合成麝香的研制概况[J].香精与香料. 1982, (2)10
[79] Wilhelmus J. Wiegers . Flavoring With a Mixture of Isochroman Musk Compounds[P]. United States Patent, Field of Search, 4250200, Feb. 1981
[80]刘宇红,阎世翔.论三环异色满类合成麝香的研究[J].北京轻工业学院学报. 1990, 8(1), 69-72
[81]闫朝阳,蔡清海.利用α-甲基苯乙烯合成佳乐麝香的研究[J].化学工程师,2002,(02):13-14
[82]刘宇红,阎世翔,龙湛祥.佳乐麝香中间体——茚满醇的合成研究[J].北京轻工业学院学报,1994(6),12(1):57—59
[83]苏建强.佳乐麝香新工艺的研究[J].香料香精化妆品,1994,(1):6-9
[84]陆培溪.一种新型的三环异色满型合成麝香[J].精细化工,1989,6
[85]汪多仁.三环异色满的合成与应用[J].四川化工,1996,(1):53-55
[86]刘树文.α-甲基苯乙烯系统的合成香料[J].北京日化,2001,(3):29-35
[87] Gerald J. Ferber . Production of Indanes[P] : United States Patent , Field of Search.4440966.Apr.1984
[88]香精和香料[M].NO. 2,1982
[89] Ferber,Gerald John.Pro~ss for the Production of Indanes[P]:European Patent,0061267.Sep.1982
[90] Lambertus G Heerlnga.New Trieydic Isochromans with Musk Odour[P].Great Br/tain Pat ent,99l146.May.1965
[91]吴传贤.三环异色满的合成[J].江苏化工,1998,(3):27-28
[92]刘宇红,阎世翔.论三环异色满类合成麝香的研究[J].北京轻工业学院学报,1990,(8):69-72
[2]汪秋安.中国古近代香料史初探[J].香料香精化妆品, 1999,(02)
[3]杨峻山,赵杨景.加速对药用植物的研究发展具有我国特色的药学事业[J].资源节约和综合利用, 1995,(01)
[4]柴素芬.药用植物在化妆品中的应用[J].广东科技, 1999,(08)
[5]葛传吉.药用植物在化妆品中的应用[J].山东中医杂志, 2005,(12)
[6] Roman Holubowicz, Magdalena Frackowiak,张佐双,张本刚,刘洋.波兰药用植物生产概况[J].中国现代中药, 2007,(04)
[7]王金陵.在《东北地区药用植物图志》审稿会上的讲话[J].国土与自然资源研究, 1982,(01)
[8]甘炳春,李榕涛.海南药用植物资源状况及其保护[J].国土与自然资源研究, 2005,(02)
[9]李英.药用植物与环境卫生[J].绿化与生活, 2001,(05)
[10]五分之一的药用植物面临灭绝[J].中国中医药信息杂志, 2004,(02)
[11]林翔云.香料史话(下)[J].国内外香化信息, 2008,(05)
[12]颜伟.用于食品的合成香料[J].食品工业科技, 1985,(02)
[13]李明.重视合成香料的发展[J].浙江化工, 1983,(02)
[14]石方.合成香料[J].现代化工, 1983,(01)
[15]日本合成香料的十年(一)[J].国内外香化信息, 2007,(09)
[16]陈景茹.国内香料工业发展概况[J].应用化工, 1984,(01)
[17]张意宽.合成香料十年概况[J].精细化工, 1988,(06)
[18]黄致喜.中国大百科全书精细化工部分选登[J].精细与专用化学品, 1987,(08)
[19]呋喃基环缩醛类合成香料[J].安徽化工, 1987,(04)
[20]陈丽珍.日推出2种新型合成香料[J].精细与专用化学品, 1992,(04)
[21]巩江,倪士峰,骆蓉芳,任艳萍,吴一飞,赵桂仿.食用香料成分研究进展[J].中国调味品, 2009,(03)
[22]胡勤裕,田如芬.近年来国外食用香料的发展动态及展望[J].食品与发酵工业, 1980,(02)
[23]王立军.食用香料贸易漫淡[J].国际市场, 1996,(03)
[24]范军.江苏省涂料工业技术进展(1995～1996年度)[J].江苏化工, 1997,(04)
[25]舒宏福.食用香料中的长效和耐高温香料[J].香料香精化妆品, 2005,(01)
[26] Firmenich建成食用香料技术中心[J].国内外香化信息, 2002,(03)
[27]张建梅.重金属废水处理技术研究进展(综述)[J].西安联合大学学报, 2003,(02)
[28]唐伟家. 1996年度江苏省石油化工技术进展[J].江苏化工, 1997,(03)
[29]孔岩,黎植昌,刘治中,蒲涛.氨基酸类农药的研究与进展[J].西南师范大学学报(自然科学版) , 1999,(03)
[30]雷得漾.对开发我省食用香料工业的几点看法[J].精细化工中间体, 1986,(02)
[31]香精香料知识问答(九)[J].国内外香化信息, 2009,(02)
[32]香精香料知识问答(十)[J].国内外香化信息, 2009,(03)
[33]香精香料知识问答(八)[J].国内外香化信息, 2009,(01)
[34]曾智勇.重要中间体CA的合成方法与工艺路线概况[J].精细化工中间体, 1988,(04)
[35]冯传启. KICl_4合成方法的改进[J].化学试剂, 1994,(04)
[36]陈竹雯.“Best Synthetic Methods”《最佳合成方法》[J].大学化学, 1988,(02)
[37]尚岩,王春颖.氨基酸酯合成方法最新研究进展[J].哈尔滨理工大学学报, 2008,(02)
[38]徐尚成.噻螨酮及其中间体的合成方法[J].农药, 1989,(01)
[39]王献钊,刘明娣.阿魏酸及阿魏酸乙酯的合成[J].湖南城市学院学报(自然科学版) , 2007,(04)
[40]李宗成.拟除虫菊酯杀虫剂的合成[J].农药, 1983,(03)
[41]思源.哥伦布的香料迷途[J].海洋世界, 2008,(02)
[42]严小青,惠富平.郑和下西洋与明代香料朝贡贸易[J].江海学刊, 2008,(01)
[43] Karen J.R.,Structuere-odor relationships[J]. Chem.Rev.,1996,96:3201~3240
[44]王天民,天然麝香与合成麝香[J].上海轻工业,1996,2:30~33
[45] Reynold C.,Fuson J.,Mills T.,The structure of musk ketone and musk tibetene[J]. J. Org.Chem., 1947,12(4):587~595
[46] Bauer K.;Garbe D.,Common fragrance and flavor materials:preparation,properties and uses[J]. Deerfield Beach:VCH Publishers,1985,40~58
[47] Lauren Barbetta.,Musk aroma chemical industry[J]. erf.&Flav.,1987,6(13):60~67
[48]董万超,赵伟刚,刘春华,麝香研究进展[J].特产研究,2001,2:48~58
[49] Geog F.,Jerry A.B.,Phillp K.,Fragrance chemistry[J]. Tetrahedron,1998,54:7633~7703
[50] Ruzicka M.,Schinz H.,A new method for the synthesis of macrocyclic ketones[J]. Helv.Chim.Acta., 1926,9:715~718
[51] Eugene G.H.,West C.O.,Progress for improving the fragrance properties ofmacrocyclic compounds obtained by thermal polymerization[P]. US,4331603,1982-03-25
[52] Arctander S.,Perfume and flavor chemicals(aroma chemicals) [J]. Las Vegas:Steffen Arctander's Publications,1969
[53]李宏,调香中的天然和合成麝香[J].四川日化,1993,4:62~67
[54] MtUler P.M.,Lamparsky D.,Perfumes:,art,science and technology[J]. London:Elsevier Applied Science,1991
[55] Elisabetta B.,Claudio F.,Stefano S.,Enantioselective perception of chiral odorants[J]. Asymm.,2003,14:1~42
[56] Akira L.,Manufacturing of microcylic musk compound from long-chaindicarboxylic acid[J]. Flav. Frag.J.,1987,15(4):161~164
[57] Jingjiang L.,Guilin D.,Common structural characteristics of musk ordorant molecules[J]. J.Mol.Struc.(Theoch),1998,2(432):97~103
[58] Api A.M.,Ford R.A.,San R.H.,An evaluation of musk xylene in a battery of genotoxicity tests[J]. Food Chem.&Toxol.,1995,33(12):1039~1045
[59] Xiaoming Z.,Wolfgang S.,Photochemical behavior of musk ambrette[J]. Chemosphere, 1999,39(1):11~21
[60] Severin M.,Peter S.,Christian S.,Occurrence of nitro and non-nitro benzenoid musk compounds in human adipose tissu[J]. e, Chemosphere,1996,33(1):17~28
[61] Gerhard G.R.,Manfred W.,Nitro musk fragrances in biota from freshwater and marine environment[J]. Chemosphere,1995,30(4):641~651
[62] Peck A.M.,Hornbuckle K.C.,Synthetic musk fragrances in lake Michigan[J], Environ.Sci.Technol.,2004,38(2):367~372
[63] Kai B.,Heinrich H.,Wilfried L.,Results of non target screening of lipophilic organic pollutants in the German bight II:polycyclic musk fragrances[J], Water Research,1998,32(6):1857-1863
[64] Martin C.,Moeder M.,Daniel X.,Biotransformation of the polycyclic musks HHCB and AHTN and metabolite formation by fungi occurring in freshwater environments[J], Environ.Sci.Technol.,2007,41(15):5395~5402
[65] Gerhard G.R.,Polycyclic musk fragrances in the aquatic environment[J]. Toxicol.Lett., 1999,11(1):37~56
[66] Philip G.S.,American musk.IV.on the biological origin of animal musk.Two more largeting ketones from the muskra[J]. t, J.Am.Chem.Soc.,1945,67(6):907-909.
[67] Antonius J.A.,Van D.W.,Ian M.P.,Macrocyclic musk mixtures[P].US,6103679,2000-08-15
[68] Lilianne A.Z.,Premysl S.,Macrocyclic musk compounds—an absence of genotoxicity in the ames test and the in vivo micronucleus assay[J]. Toxicol.Lett.,2002,135(1):155~163
[69]舒宏福,麝香类香料的开发及安全环保问题[J].精细化工,1999,16:311~315
[70]胡勤裕,田如芬.近年来国外食用香料的发展动态及展望[J].食品与发酵工业, 1980,(02)
[71]浅井治海.香料合成技术的发展[J].香料. 1999,(2):99-103
[72] Philip. Kraft.‘Brain Aided’Musk Design[J]. Chemistry and Biodiversity, 2004(1):1957
[73] Philip. Kraft. Aroma chemicals IV: Musks[J]. Chemistry and Technology of Flavours and Fragrances, 2005: 143-168.
[74]张高勇.日用化学品[M].北京:化学工业出版社,1999
[75] Lambertus G. Heerlnga . New Trieydic Isochromans with Musk Odour [P]. Great Britain Patent, 99l146, May. 1965
[76] Gerald J. Ferber . Production of Indanes [P]. United States Patent, Field of Search . 4440966, Apr. 1984
[77] Ferber , Gerald John . Process for the Production of Indanes [P]. European Patent, 0061267, Sept. 1982
[78]刘树文.三环异色满型合成麝香的研制概况[J].香精与香料. 1982, (2)10
[79] Wilhelmus J. Wiegers . Flavoring With a Mixture of Isochroman Musk Compounds[P]. United States Patent, Field of Search, 4250200, Feb. 1981
[80]刘宇红,阎世翔.论三环异色满类合成麝香的研究[J].北京轻工业学院学报. 1990, 8(1), 69-72
[81]闫朝阳,蔡清海.利用α-甲基苯乙烯合成佳乐麝香的研究[J].化学工程师,2002,(02):13-14
[82]刘宇红,阎世翔,龙湛祥.佳乐麝香中间体——茚满醇的合成研究[J].北京轻工业学院学报,1994(6),12(1):57—59
[83]苏建强.佳乐麝香新工艺的研究[J].香料香精化妆品,1994,(1):6-9
[84]陆培溪.一种新型的三环异色满型合成麝香[J].精细化工,1989,6
[85]汪多仁.三环异色满的合成与应用[J].四川化工,1996,(1):53-55
[86]刘树文.α-甲基苯乙烯系统的合成香料[J].北京日化,2001,(3):29-35
[87] Gerald J. Ferber . Production of Indanes[P] : United States Patent , Field of Search.4440966.Apr.1984
[88]香精和香料[M].NO. 2,1982
[89] Ferber,Gerald John.Pro~ss for the Production of Indanes[P]:European Patent,0061267.Sep.1982
[90] Lambertus G Heerlnga.New Trieydic Isochromans with Musk Odour[P].Great Br/tain Pat ent,99l146.May.1965
[91]吴传贤.三环异色满的合成[J].江苏化工,1998,(3):27-28
[92]刘宇红,阎世翔.论三环异色满类合成麝香的研究[J].北京轻工业学院学报,1990,(8):69-72