CN109715771A - 香料组合物 - Google Patents
香料组合物 Download PDFInfo
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- CN109715771A CN109715771A CN201780057025.7A CN201780057025A CN109715771A CN 109715771 A CN109715771 A CN 109715771A CN 201780057025 A CN201780057025 A CN 201780057025A CN 109715771 A CN109715771 A CN 109715771A
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- Prior art keywords
- formula
- methyl
- ester
- fragrance
- reaction
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 235000013599 spices Nutrition 0.000 title claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 20
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 6
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- 230000036541 health Effects 0.000 claims description 5
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- 239000003205 fragrance Substances 0.000 abstract description 69
- 238000013329 compounding Methods 0.000 abstract description 15
- 239000002994 raw material Substances 0.000 abstract description 13
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- -1 fructose ester Chemical class 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 38
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- 150000002148 esters Chemical class 0.000 description 25
- 150000001336 alkenes Chemical class 0.000 description 19
- 238000007037 hydroformylation reaction Methods 0.000 description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 17
- 229910002091 carbon monoxide Inorganic materials 0.000 description 17
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 5
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- 238000010189 synthetic method Methods 0.000 description 5
- YKVIWISPFDZYOW-UHFFFAOYSA-N 6-Decanolide Chemical compound CCCCC1CCCCC(=O)O1 YKVIWISPFDZYOW-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 244000241257 Cucumis melo Species 0.000 description 4
- 235000009847 Cucumis melo var cantalupensis Nutrition 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 4
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- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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Abstract
香料组合物作为调配香料原料是有用的,且具有优异的香气和香气持续性,所述香料组合物含有:式(1)所示的化合物;(式中,R1、R2、R3独立地为氢或甲基,X为碳数1~4的烷基,R4和R5独立地为氢或‑CHO基,AA为单键或双键。)。
Description
技术领域
本发明涉及香料组合物。
背景技术
已知酯类中存在作为香料有用的化合物。例如,非专利文献1中记载了如下内容:具有玫瑰样香气的醋酸香叶酯、具有茉莉花样的甘甜的香气的茉莉酸甲酯、具有果味的香气的果糖酯、具有强烈干果味的香气的苯甲酸甲酯等作为调配香料原料是有用的。
现有技术文献
非专利文献
非专利文献1:中岛基贵编、“香料与调香的基础知识”、1995年、215页、235页、244~246页、产业图书株式会社
发明内容
发明要解决的问题
本发明的课题在于,提供:作为调配香料原料有用的、具有优异的香气和香气持续性的香料组合物。
用于解决问题的方案
本发明人对萜类中具有多环结构的化合物很多具有优异的香气很感兴趣,合成了多种具有多环结构的化合物,并对其香气进行了评价,结果发现:降冰片烷-2-羧酸酯化合物类具有优异的香气,作为调配香料是极优异的,至此完成了本发明。
即,本发明如以下所述。
[1]
一种香料组合物,其含有式(1)所示的化合物;
(式(1)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基,
R4和R5独立地为氢或-CHO基,
为单键或双键。)。
[2]
根据[1]所述的香料组合物,其中,式(1)所示的化合物为选自由以下的式(1-1)~式(1-3)组成的组中的1种以上,
(式(1-1)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基。)
(式(1-2)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基。)
(式(1-3)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基,
R4和R5中的任一者为氢,另一者为-CHO基。)。
[3]
化妆品、健康卫生材料、杂货、饮料、食品、准药品或药品,其含有[1]或[2]所述的香料组合物。
发明的效果
本发明的含有降冰片烷-2-羧酸酯化合物类的香料组合物具有优异的香气,且具有优异的香气持续性,因此,作为对梳妆用品、肥皂、衣料用洗涤剂等宽范围的制品的赋香成分是有用的。
具体实施方式
以下,对用于实施本发明的方式(以下,简称为“本实施方式”)详细进行说明。以下的本实施方式是用于说明本发明的示例,不意图将本发明限定于以下的内容。本发明可以在其主旨的范围内适宜变形而实施。
[香料组合物]
本实施方式的香料组合物含有降冰片烷-2-羧酸酯化合物类、即、式(1)所示的化合物。
本实施方式的香料组合物可以为以式(1)所示的化合物单独或2种以上为主成分的香料组合物,也可以为在通常使用的其他香料成分、期望组成的调配香料中单独混合有式(1)所示的化合物、或混合有2种以上的式(1)所示的化合物的香料组合物。
以式(1)所示的化合物单独或2种以上为主成分是指,相对于该香料组合物总量包含通常为85质量%以上、优选90质量%以上、更优选96质量%以上、进一步优选98质量%以上的式(1)所示的化合物。
式(1)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基,
R4和R5独立地为氢或-CHO基,
为单键或双键。
本实施方式中的式(1)所示的化合物优选为以下的式(1-1)~式(1-3)所示的化合物。式(1-1)~式(1-3)所示的化合物可以为单独1种,也可以为2种以上的组合。
式(1-1)中,R1、R2、R3和X与式(1)中的R1、R2、R3和X为相同含义。
即,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基。
式(1-2)中,R1、R2、R3和X与式(1)中的R1、R2、R3和X为相同含义。
即,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基。
式(1-3)中,R1、R2、R3和X与式(1)中的R1、R2、R3和X为相同含义。
即,式(1-3)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基。
R4和R5中的任一者为氢,另一者为-CHO基。
式(1)、式(1-1)~式(1-3)中的R1、R2、R3独立地为氢或甲基。
R2和R3优选氢。
另外,式(1)、式(1-1)~式(1-3)中的X为碳数1~4的烷基。作为碳数1~4的烷基,可以举出甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基。X优选甲基和乙基。
式(1)和式(1-1)~式(1~3)所示的化合物可以为关于不体现立体构型的不对称碳的光学异构体中的任1种的单一物,也可以为以任意比例包含它们的混合物。
作为式(1-1)所示的化合物,优选为降冰片烯-2-羧酸甲酯、降冰片烯-2-羧酸乙酯、降冰片烯-2-甲基-2-羧酸甲酯、降冰片烯-2-甲基-2-羧酸乙酯中的任意者,更优选为降冰片烯-2-羧酸甲酯、降冰片烯-2-甲基-2-羧酸甲酯中的任意者。
本实施方式中的式(1-1)所示的化合物具备兼有强烈的成熟香蕉和香瓜样的果味和臭氧样的海洋香的香气、乃至兼有新鲜的青花香(Floral Green)调的香味和果味的香气,且持续性也优异。
作为式(1-2)所示的物质,优选为降冰片烷-2-羧酸甲酯、降冰片烷-2-羧酸乙酯、降冰片烷-2-甲基-2-羧酸甲酯、降冰片烷-2-甲基-2-羧酸乙酯中的任意者,更优选为降冰片烷-2-羧酸甲酯、降冰片烷-2-甲基-2-羧酸甲酯中的任意者。
本实施方式中的式(1-2)所示的化合物具备有果味感的草本绿(HerbalGreen)样的香气、且持续性也优异。
作为式(1-3)所示的化合物,优选为甲酰基降冰片烷-2-羧酸甲酯、甲酰基降冰片烷-2-羧酸乙酯、甲酰基降冰片烷-2-甲基-2-羧酸甲酯、甲酰基降冰片烷-2-甲基-2-羧酸乙酯中的任意者,更优选为甲酰基降冰片烷-2-羧酸甲酯、甲酰基降冰片烷-2-甲基-2-羧酸甲酯中的任意者。
本实施方式中的式(1-3)所示的化合物为兼有强烈的香瓜、猕猴桃样果味和新鲜的海洋香、和玫瑰样花香的新型的香气,且持续性也优异。
如以上,式(1)所示的化合物具有果味等优异的香气、且持续性也优异,因此,可以单独或与其他成分组合而作为化妆品类、健康卫生材料、杂货、饮料、食品、准药品、药品等各种制品的香气成分来使用。具体而言,可以作为肥皂、洗发剂、护发素、洗涤剂、化妆品、喷雾制品、芳香剂、香水、或沐浴剂等的赋香成分来使用。
[式(1)所示的化合物的制造方法]
本实施方式中的式(1)所示的化合物例如可以通过如下合成法而制作:将使烯烃和二环戊二烯进行加热反应的狄尔斯-阿尔德反应作为关键工序。
具体而言,式(1-1)所示的化合物可以如下通过使烯烃和二环戊二烯进行加热反应的狄尔斯-阿尔德反应而制造。
(式中,R1、R2、R3和X与式(1)中的R1、R2、R3和X为相同含义。即,R1、R2、R3独立地为氢或甲基,X为碳数1~4的烷基。)
作为前述烯烃,例如可以举出丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸丁酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸丁酯、巴豆酸甲酯、巴豆酸乙酯、巴豆酸丙酯、巴豆酸丁酯、3-甲基巴豆酸甲酯、3-甲基巴豆酸乙酯、3-甲基巴豆酸丙酯、3-甲基巴豆酸丁酯等。这些烯烃中,优选丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、巴豆酸甲酯、巴豆酸乙酯、3-甲基巴豆酸甲酯、3-甲基巴豆酸乙酯,更优选丙烯酸甲酯、丙烯酸乙酯等、甲基丙烯酸甲酯、甲基丙烯酸乙酯。
另外,前述二环戊二烯优选其纯度高,理想的是尽量避免丁二烯、异戊二烯等的含量。二环戊二烯的纯度优选90%以上、更优选95%以上。另外,已知二环戊二烯在加热条件下解聚而成为环戊二烯,因此,也可以使用环戊二烯代替二环戊二烯。
为了使狄尔斯-阿尔德反应有效地进行,重要的是,环戊二烯存在于反应体系内,因此,反应温度优选100℃以上、更优选120℃以上、进一步优选130℃以上。
另一方面,为了抑制高沸物质的产生,反应温度优选250℃以下的温度。
另外,作为反应溶剂,也可以使用烃类、醇类、酯类等,适合的是碳数6以上的脂肪族烃类、具体而言环己烷、甲苯、二甲苯、乙基苯、均三甲苯、丙醇、丁醇等。
作为本实施方式的狄尔斯-阿尔德反应的反应方式,可以采用:利用槽型反应器等的分批式、向反应条件下的槽型反应器供给基质、基质溶液的半分批式、在反应条件下使基质类在管型反应器中流通的连续流通式等各种反应方式。
上述反应中得到的产物可以作为含有式(1)所示的化合物的香料组合物使用,也可以作为如下反应的原料使用,也可以通过蒸馏、提取、析晶等方法纯化后作为香料组合物、如下反应的原料。
所得产物、即、式(1-1)所示的化合物可以作为如下反应的原料,可以作为用于合成式(1-2)所示的化合物和式(1-3)所示的化合物的原料。
具体而言,式(1-2)所示的化合物可以如下通过使式(1-1)所示的化合物在催化剂存在下进行氢化反应而制造。
(式中,R1、R2、R3和X与式(1)中的R1、R2、R3和X为相同含义。即,R1、R2、R3独立地为氢或甲基,X为碳数1~4的烷基。)
前述氢化反应中使用的催化剂只要为通常不饱和键的氢化中使用的催化剂就没有特别限定,优选含有选自周期表第8~11族金属中的至少1种的催化剂。具体而言,可以举出:含有铁、钴、镍、铜、钌、铑、钯、银、锇、铱、铂、金中的至少1种的催化剂。
前述氢化催化剂可以为固体催化剂也可以为均相催化剂,从与反应物的分离性的观点出发,优选固体催化剂。作为固体催化剂,可以举出非负载型金属催化剂、负载金属催化剂等。
作为非负载型金属催化剂,优选可以举出雷尼镍、雷尼钴和雷尼铜等雷尼催化剂;铂、钯、铑和钌等的氧化物;胶体催化剂;等。
作为负载金属催化剂,例如可以举出:在氧化镁、氧化锆、氧化铈、硅藻土、活性炭、氧化铝、二氧化硅、沸石和二氧化钛等载体上负载或混合有铁、钴、镍、铜、钌、铑、钯、银、锇、铱、铂和金中的至少1种而成的催化剂。
作为负载金属催化剂,具体而言,可以适宜举出在载体上负载有铜-铬催化剂(Adkins催化剂)、铜-锌催化剂、铜-铁等铜催化剂而成的负载铜催化剂、Pt/C、Pt/氧化铝等负载铂催化剂、Pd/C、Pd/氧化铝等负载钯催化剂、Ru/C、Ru/氧化铝等负载钌催化剂、Rh/C、Rh/氧化铝等负载铑催化剂等。
这些催化剂中,从反应活性和选择性的方面出发,更优选含有铜的催化剂。
氢化催化剂的用量可以根据催化剂的种类而适宜调整,相对于作为原料的降冰片烯-2-羧酸酯化合物,为0.001~100质量%、优选0.01~30质量%、进一步优选0.1~20质量%。
氢化反应的氢气压力可以为常压、加压下均可,通常为常压~4.0MPa、优选0.1~3.0MPa、更优选0.1~2.0MPa。
氢化反应可以在无溶剂下进行,也可以使用溶剂而进行。
作为溶剂,可以举出水、甲酸和乙酸等有机酸类;乙酸乙酯和乙酸丁酯等酯类;苯、邻二氯苯、甲苯和二甲苯等芳香族化合物类;己烷、庚烷和环己烷等烃类;甲醇、乙醇、异丙醇、叔丁醇、乙二醇和二乙二醇等醇类;二氧杂环己烷、四氢呋喃、二甲氧基乙烷和二甘醇二甲醚等醚类;等或它们的混合物。
在氢化反应中使用溶剂时的溶剂的量相对于作为原料的降冰片烯-2-羧酸酯化合物,通常为0.1~30质量倍、优选为0.2~20质量倍。
氢化反应的反应温度通常可以在-90℃~200℃下进行。反应温度优选20℃~150℃、更优选50℃~120℃。
氢化反应的形式只要能进行催化氢化反应就没有特别限定,可以为通常使用的公知的形式。作为氢化反应的形式,例如可以举出利用如下反应器的形式等:使催化剂在流体中流动化而进行催化氢化反应的悬浮床反应器、填充固定化催化剂且供给流体从而进行催化氢化反应的固定床反应器。
氢化反应中得到的反应产物利用旋转蒸发仪等将低沸物等去除后,使用蒸馏塔进行精馏,从而可以作为含有式(1-2)所示的化合物的香料组合物使用。
式(1-3)所示的化合物可以如下合成:在铑化合物、有机磷化合物的存在下,对于式(1-1)所示的化合物,使一氧化碳和氢气进行氢甲酰化反应,从而合成。
(式中,R1、R2、R3和X与式(1)中的R1、R2、R3和X为相同含义。即,式中,R1、R2、R3独立地为氢或甲基,X为碳数1~4的烷基。R4和R5中的任一者为氢,另一者为-CHO基。)
氢甲酰化反应中使用的铑化合物只要为与有机磷化合物形成络合物、且在一氧化碳和氢的存在下体现氢甲酰化活性的化合物就对其前体的形态没有限制。可以将二羰基乙酰丙酮铑(以下,记作Rh(acac)(CO)2)、Rh2O3、Rh4(CO)12、Rh6(CO)16、Rh(NO3)3等催化剂前体物质与有机磷化合物一起导入至反应混合物中,在反应容器内形成具有催化活性的铑金属氢化物羰基磷络合物,或者可以预先制备铑金属氢化物羰基磷络合物,将其导入至反应器内。作为氢甲酰化反应中使用的铑化合物的优选制造方法,具体例中可以举出如下方法:在溶剂的存在下,使Rh(acac)(CO)2与有机磷化合物反应后,与过量的有机磷化合物一起导入至反应器,形成具有催化活性的铑-有机磷络合物。
氢甲酰化反应中的铑化合物的用量相对于作为氢甲酰化反应的基质的烯烃1摩尔,优选为0.1~30微摩尔、更优选为0.2~20微摩尔、进一步优选为0.5~10微摩尔。通过使铑化合物的用量相对于烯烃1摩尔少于30微摩尔,从而即使不设置铑络合物的回收再利用设备,也可以减轻铑催化剂费用,因此,可以减轻回收再利用设备的经济负担。另外,通过使铑化合物的用量相对于烯烃1摩尔多于0.1微摩尔,从而可以以高的收率得到氢甲酰化反应产物。
氢甲酰化反应中,作为与铑化合物形成氢甲酰化反应的催化剂的有机磷化合物,例如可以举出通式P(-R6)(-R7)(-R8)所示的膦或P(-OR6)(-OR7)(-OR8)所示的亚磷酸酯等。
作为R6、R7、R8的具体例,可以举出:任选被碳数1~4的烷基或碳数1~4的烷氧基所取代的芳基、和任选被碳数1~4的烷基或碳数1~4的烷氧基所取代的脂环式烷基等。
作为有机磷化合物,具体而言,适合使用三苯基膦、亚磷酸三苯酯。
有机磷化合物的用量优选为铑金属的500倍摩尔~10000倍摩尔,更优选为700倍摩尔~5000倍摩尔,进一步优选为900倍摩尔~2000倍摩尔。有机磷化合物的用量少于铑金属的500倍摩尔的情况下,催化活性物质的铑金属氢化物羰基磷络合物的稳定性受损,有反应的进行变慢的倾向。另外,有机磷化合物的用量多于铑金属的10000倍摩尔的情况下,有机磷化合物所耗费的成本有增加的倾向。
氢甲酰化反应也可以在不使用溶剂的情况下进行,通过使用对反应为非活性的溶剂,也可以更适合地实施。作为溶剂,例如只要使烯烃、二环戊二烯或环戊二烯、和前述铑化合物、以及前述有机磷化合物溶解就没有特别限制。
作为溶剂,具体而言,可以举出脂肪族烃、脂环式烃、和芳香族烃等烃类;脂肪族酯、脂环式酯、和芳香族酯等酯类;脂肪族醇、和脂环式醇等醇类;芳香族卤化物;等。这些溶剂中,优选烃类,更优选脂环式烃、芳香族烃。
作为进行氢甲酰化反应的情况下的温度,优选40℃~160℃、更优选80℃~140℃。通过使反应温度为40℃以上,从而可以得到充分的反应速度,可以抑制作为原料的烯烃的残留。另外,通过使反应温度为160℃以下,从而可以抑制源自原料烯烃、反应产物的副产物的生成,防止反应效果的降低。
进行氢甲酰化反应的情况下,必须在利用一氧化碳(CO)和氢(H2)气体的加压下进行反应。可以将CO和H2气体各自独立地导入至反应体系内,另外,也可以以预先制备好的混合气体的形式导入至反应体系内。导入至反应体系内的CO和H2气体的摩尔比(=CO/H2)优选0.2~5、更优选0.5~2、进一步优选0.8~1.2。CO和H2气体的摩尔比脱离该范围时,氢甲酰化反应的反应活性、目标醛的选择率有时降低。导入至反应体系内的CO和H2气体随着反应的进行而逐渐减少,因此,如果利用预先制备好的CO与H2的混合气体,则反应控制有时简便。
作为氢甲酰化反应的反应压力,优选1~12MPa、更优选1.2~9MPa、进一步优选1.5~5MPa。通过使反应压力为1MPa以上,从而可以得到充分的反应速度,可以抑制作为原料的烯烃残留。另外,通过使反应压力为12MPa以下,从而变得无需耐压性能优异的昂贵的设备,因此,在经济上是有利的。特别是以分批式、半分批式进行反应的情况下,需要在反应结束后排出CO和H2气体并降压,越为低压,CO和H2气体的损耗越少,因此,在经济上是有利的。
作为进行氢甲酰化反应的情况下的反应方式,适宜的是分批式反应、半分批式反应。半分批式反应可以如下进行:在反应器中加入铑化合物、有机磷化合物、前述溶剂,进行利用CO/H2气体的加压、加热等,形成前述的反应条件后,向反应器供给作为原料的烯烃或其溶液,从而进行。
前述氢甲酰化反应中得到的反应产物可以利用旋转蒸发仪等将低沸物等去除后,利用蒸馏塔进行精馏,从而作为含有式(1-3)所示的化合物的香料组合物使用。
对于本实施方式的香料组合物,可以在通常使用的其它香料成分、期望组成的调配香料中,单独混合前述式(1)所示的化合物或混合2种以上前述式(1)所示的化合物进行配混。
本实施方式的香料组合物中的式(1)所示的化合物的配混量可以根据调配香料的种类、目标香气的种类和香气的强度等而适宜调整,在调配香料中优选加入0.01~90质量%,更优选加入0.1~50质量%。
本实施方式的香料组合物中,作为能与式(1)所示的化合物组合而使用的香料成分,不限定于以下的成分,例如可以举出:聚氧乙烯月桂基硫酸醚等表面活性剂;二丙二醇、邻苯二甲酸二乙酯、乙二醇、丙二醇、肉豆蔻酸甲酯、柠檬酸三乙酯等溶剂;柠檬烯、α-蒎烯、β-蒎烯、松油烯、雪松烯、长叶烯、巴伦西亚橘烯等烃类;芳樟醇、香茅醇、香叶醇、橙花醇、松油醇、二氢月桂烯醇、乙基芳樟醇、金合欢醇、橙花叔醇、顺式-3-己烯醇、柏木脑、薄荷醇、冰片、β-苯基乙醇、苄醇、苯基己醇、2,2,6-三甲基环己基-3-己醇、1-(2-叔丁基环己基氧基)-2-丁醇、4-异丙基环己烷甲醇、4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、异莰基环己醇、3,7-二甲基-7-甲氧基辛烷-2-醇等醇类;丁子香酚、百里香酚、香兰素等酚类;甲酸芳樟酯、甲酸香茅酯、甲酸香叶酯、乙酸正己酯、顺式-3-己烯基乙酸酯、乙酸芳樟酯、乙酸香茅酯、乙酸香叶酯、乙酸橙花酯、乙酸萜品酯、乙酸诺卜酯(nopylacetate)、乙酸冰片酯、乙酸异冰片酯、乙酸邻叔丁基环己酯、乙酸对叔丁基环己酯、乙酸三环癸烯酯、乙酸苄酯、乙酸苏合香酯、乙酸肉桂酯、乙酸二甲基苄基甲醇酯、乙酸3-戊基四氢吡喃-4-基酯、丙酸香茅酯、丙酸三环癸烯酯、丙酸烯丙基环己酯、丙酸乙基2-环己酯、丙酸苄酯、丁酸香茅酯、正丁酸二甲基苄基甲醇酯、异丁酸三环癸烯酯、2-壬烯酸甲酯、苯甲酸甲酯、苯甲酸苄酯、肉桂酸甲酯、水杨酸甲酯、水杨酸正己酯、水杨酸顺式-3-己烯酯、惕各酸香叶酯(Geranyl tiglate)、惕各酸顺式-3-己烯酯、茉莉酮酸甲酯、二氢茉莉酮酸甲酯、苯甲酸甲基-2,4-二羟基-3,6-二甲酯、甲基苯基缩水甘油酸乙酯、邻氨基苯甲酸甲酯、果糖酯(fruitate)等酯类;正辛醛、正癸醛、正十二醛、2-甲基十一醛、10-十一碳烯醛、香茅醛、柠檬醛、羟基香茅醛、二甲基四氢苯甲醛、4(3)-(4-羟基-4-甲基戊基)-3-环己烯-1-羧醛、2-环己基丙醛、对叔丁基-α-甲基氢肉桂醛、对异丙基-α-甲基氢化肉桂醛、对乙基-α,α-二甲基氢化肉桂醛、α-戊基肉桂醛、α-己基肉桂醛、胡椒醛、α-甲基-3,4-亚甲基二氧基氢化肉桂醛等醛类;甲基庚烯酮、4-亚甲基-3,5,6,6-四甲基-2-庚酮、戊基环戊酮、3-甲基-2-(顺式-2-戊烯-1-基)-2-环戊烯-1-酮、甲基环戊烯酮、玫瑰酮、γ-甲基紫罗兰酮、α-紫罗兰酮、香芹酮、薄荷酮、樟脑、诺卡酮、苄基丙酮、茴香丙酮、甲基β-萘酮、2,5-二甲基-4-羟基-3(2H)-呋喃酮、麦芽酚、7-乙酰基-1,2,3,4,5,6,7,8-八氢-1,1,6,7-四甲基萘、麝香酮、灵猫酮、环十五烷酮、环十六烯酮等酮类;乙醛乙基苯基丙基缩醛、柠檬醛二乙基缩醛、苯基乙醛甘油缩醛、乙基乙酰乙酸酯乙二醇缩酮类的缩醛类和缩酮类;茴香脑、β-萘基甲基醚、β-萘基乙基醚、柠檬烯氧化物、玫瑰氧化物、1,8-桉叶素、消旋体或光学活性的十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃等醚类;香茅腈等腈类;γ-壬内酯、γ-十一内酯、σ-癸内酯、γ-茉莉内酯、香豆素、环十五内酯、环十六内酯、黄葵内酯、十三烷二酸环乙撑酯、11-氧杂十六内酯等内酯类;橙子、柠檬、佛手柑、柑橘、薄荷、绿薄荷、薰衣草、黄春菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、天竺葵、茉莉花、依兰、茴芹、丁香、姜、肉豆蔻、小豆蔻、雪松、柏、香根草、广藿香、劳丹脂等天然精油、天然提取物等其他香料物质等。该其他香料物质可以单独使用或配混多种。
为了赋予香气、和为了进行配混对象物的香气的改良,含有式(1)所示的化合物的香料组合物可以作为化妆品、健康卫生材料、杂货、饮料、食品、准药品、药品等各种制品的香气成分使用。
含有式(1)所示的化合物的香料组合物例如可以作为香水、古龙水类等香味制品;洗发剂、护发素类、护发素(hair tonic)、护发霜类、摩丝、啫喱、发蜡、喷雾等头发用化妆用品;化妆水、美容液、霜、乳液、面膜、粉底、香粉、口红、各种美容品类等肌肤用化妆料;洗碗洗涤剂、洗衣用洗涤剂、柔软剂类、消毒用洗涤剂类、除臭洗涤剂类、室内芳香剂、家具保养剂、玻璃清洁剂、家具清洁剂、地板清洁剂、消毒剂、杀虫剂、漂白剂等各种健康卫生用洗涤剂类;牙膏、漱口水、沐浴剂、止汗制品、烫发液等准药品;卫生纸、薄绵纸等杂货;药品等;食品等香气成分而使用。
另外,本实施方式的香料或香料组合物在上述制品中的配混量以式(1)所示的甲酰基降冰片烷-2-羧酸酯化合物的量计,相对于制品的总量,优选为0.001~50质量%、更优选为0.01~20质量%。
实施例
以下,依据实施例对本发明的方法进一步详细进行说明,但本发明不限定于这些实施例。
示出以下的实施例中的测定方法。
<气相色谱法分析条件>
·分析装置:株式会社岛津制作所制毛细管色谱仪GC-2010Plus
·分析柱:GL Sciences,Inc.制、InertCap1(30m、0.32mmI.D.、膜厚0.25μm
·柱温箱温度:60℃(0.5分钟)-升温速度15℃/分钟-280℃(4分钟)
·检测器:FID、温度280℃
<羧酸酯化合物收率、选择率>
通过气相色谱法分析,求出作为产物的羧酸酯化合物的面积比例(GC%),通过内标法,根据下述式算出降冰片烯-2-羧酸酯和降冰片烷-2-羧酸酯化合物的收率、选择率。
·烯烃基准的收率(摩尔%)=降冰片烯-2-羧酸酯的获得量(摩尔)/烯烃的投入量(摩尔)×100
·二环戊二烯基准的收率(摩尔%)=降冰片烯-2-羧酸酯的获得量(摩尔)/二环戊二烯的投入量(摩尔)×100/2
·烯烃基准的选择率(摩尔%)=降冰片烯-2-羧酸酯的获得量(摩尔)/烯烃的反应量(摩尔)×100
·二环戊二烯基准的选择率(摩尔%)=降冰片烯-2-羧酸酯的获得量(摩尔)/二环戊二烯的反应量(摩尔)×100/2
·氢化反应的收率(摩尔%)=降冰片烷-2-羧酸酯的获得量(摩尔)/(降冰片烯-2-羧酸酯的投入量(摩尔)×100
·氢化反应的选择率(摩尔%)=降冰片烷-2-羧酸酯的获得量(摩尔)/降冰片烯-2-羧酸酯的反应量(摩尔)×100
·氢甲酰化反应的收率(摩尔%)=甲酰基降冰片烷-2-羧酸酯的获得量(摩尔)/降冰片烯-2-羧酸酯的投入量(摩尔)×100
·氢甲酰化反应的选择率(摩尔%)=甲酰基降冰片烷-2-羧酸酯的获得量(摩尔)/降冰片烯-2-羧酸酯的反应量(摩尔)×100
<GC-MS测定条件>
·分析装置:株式会社岛津制作所制、GCMS-QP2010Plus
·离子化电压:70eV
·分析柱:Agilent Technologies制、DB-1(30m、0.32mmI.D.、膜厚1.00μm)
·柱温箱温度:60℃(0.5分钟)-升温速度15℃/分钟-280℃(4分钟)
[实施例1]
(降冰片烯-2-羧酸甲酯的合成法)
使用具备磁力感应式搅拌机和位于上部的3个入口喷嘴的内容积500ml的不锈钢制高压釜,进行合成。
首先,在高压釜中投入正十二烷(东京化成制试剂特级)101.2g,进行氮气气体置换后,使液温为195℃。
边将反应温度保持为195℃,边从高压釜上部用1小时供给丙烯酸甲酯96.4g(1.12摩尔)与二环戊二烯105.7g(0.80摩尔)的混合液后,进而,继续搅拌2小时。
将前述反应液冷却后,通过内标法对所得液体301.0g用气相色谱法进行分析,结果含有目标降冰片烯-2-羧酸甲酯化合物133.2g。丙烯酸甲酯基准的效果如下:收率78.2摩尔%、选择率79.0摩尔%,二环戊二烯基准的效果如下:收率54.7摩尔%、选择率59.3摩尔%。
用理论塔板数20级的精馏塔对所得液体进行精馏(馏出温度88℃、真空度2.7kPa),结果得到在气相色谱法分析中为98.5GC%者120.5g(蒸馏收率90.5摩尔%)作为主馏部分。
对所得馏分用GC-MS进行分析,结果示出目标物的分子量152。
所得馏分与仅具有果味的香气的公知的果糖酯或仅具有玫瑰样香气的公知的醋酸香叶酯不同,其具备兼有成熟香蕉和香瓜样的果味、和臭氧样的海洋香的新型香气,与其他公知的酯或醋酸香叶酯相比,具有香气持续性优异的特征。
(具有花香感的杏子样果味的香料组合物)
首先,制作表1所示的组成的香料组合物(对照品)。接着,在该对照品90质量份中加入上述中制备的降冰片烯-2-羧酸甲酯10质量份,制作香料组合物。
所得香料组合物在基于调香师的香味评价中,确认为具有浓厚的栀子花样花香感的杏子样果味的香味。
[表1]
配混成分 | 聚合份 |
苄醇 | 25 |
芳樟醇 | 20 |
ε-癸内酯 | 17 |
三环癸烷-2-羧酸乙酯 | 15 |
乙酸苄酯 | 5 |
乙酸异丁酯 | 3 |
丙二酸二乙酯 | 2 |
β-紫罗兰酮 | 2 |
柠檬烯 | 1 |
总计 | 90 |
[实施例2]
(降冰片烯-2-甲基-2-羧酸甲酯的合成法)
作为烯烃,使用甲基丙烯酸甲酯112.1g(1.12摩尔),除此之外,与实施例1同样地进行狄尔斯-阿尔德反应和处理。
将前述反应液冷却后,通过内标法,用气相色谱法对所得液体316.9g进行分析,结果含有目标降冰片烯-2-甲基-2-羧酸甲酯化合物140.0g。甲基丙烯酸甲酯基准的效果如下:收率75.2摩尔%、选择率75.9摩尔%,二环戊二烯基准的效果如下:收率52.7摩尔%、选择率57.4摩尔%。
使用理论塔板数40级的旋转带蒸馏塔,对所得液体进行精馏(馏出温度90℃、真空度2.7kPa),结果得到在气相色谱法分析中为98.5GC%者127.5g(蒸馏收率91.1摩尔%)作为主馏部分。
对所得馏分用GC-MS进行分析,结果示出目标物的分子量166。
所得馏分与仅具有果味的香气的公知的果糖酯或仅具有玫瑰样香气的公知的醋酸香叶酯不同,其具有兼有新鲜的青花香样的香味和果味的新型香气,与其他公知的酯或醋酸香叶酯相比,有香气持续性优异的特征。
(认为是新鲜的西洋梨那样的水果型的香料组合物)
首先,制作表2所示的组成的香料组合物(对照品)。接着,在该对照品90质量份中加入上述中制备的降冰片烯-2-甲基-2-羧酸甲酯10质量份,制作香料组合物。
所得香料组合物在基于调香师的香味评价中,确认为认为是新鲜的西洋梨那样的水果型的香味。
[表2]
配混成分 | 聚合份 |
三环癸烷-2-羧酸乙酯 | 30 |
环十五烷酮 | 14 |
乙酸异丁酯 | 12 |
庚酸烯丙酯 | 10 |
ε-癸内酯 | 10 |
β-紫罗兰酮 | 5 |
苄醇 | 3 |
异丙基环己醇 | 3 |
乙酰乙酸乙酯 | 2 |
柠檬烯 | 1 |
总计 | 90 |
[实施例3]
(降冰片烷-2-羧酸甲酯的合成法)
使用具备磁力感应式搅拌机和位于上部的3个入口喷嘴的内容积500ml的不锈钢制高压釜进行氢化反应。
在前述高压釜中,投入Cu-Cr催化剂(日挥制N-203S)6.0g、异丙醇(和光纯药工业制特级)120.0g,在170℃、氢气压力2MPa下,进行1小时的活化。冷却后,投入上述中制备的降冰片烯-2-羧酸甲酯60.0g,在120℃、氢气压力2MPa下进行3小时搅拌,进行还原反应。将反应液过滤,去除催化剂,得到含有降冰片烷-2-羧酸甲酯57.6g的反应液173.9g(转化率100%、收率96.2%)。降冰片烯-2-羧酸甲酯基准的效果如下:收率96.2摩尔%、选择率100摩尔%。
使用理论塔板数40级的旋转带蒸馏塔,对所得液体进行精馏(馏出温度89℃、真空度2.7kPa),结果得到在气相色谱法分析中为98.5GC%者53.5g(蒸馏收率91.5摩尔%)作为主馏部分。
对所得馏分用GC-MS进行分析,结果示出目标物的分子量154。
所得馏分与仅具有果味的香气的公知的果糖酯或仅具有玫瑰样香气的公知的醋酸香叶酯不同,其具备有强烈的果味感的草本绿样的新型香气,与其他公知的酯或醋酸香叶酯相比,有香气持续性优异的特征。
(具有青苹果的新鲜感的水果型的香料组合物)
首先,制作表3所示的组成的香料组合物(对照品)。接着,在该对照品90质量份中加入上述中制备的降冰片烷-2-羧酸甲酯10质量份,制作香料组合物。
所得香料组合物在基于调香师的香味评价中,确认为具有青苹果的新鲜感的水果型的香味。
[表3]
配混成分 | 聚合份 |
三环癸烷-2-羧酸乙酯 | 30 |
环十五烷酮 | 14 |
乙酸异丁酯 | 12 |
庚酸烯丙酯 | 10 |
ε-癸内酯 | 10 |
β-紫罗兰酮 | 5 |
苄醇 | 3 |
异丙基环己醇 | 3 |
乙酰乙酸乙酯 | 2 |
柠檬烯 | 1 |
总计 | 90 |
[实施例4]
(甲酰基降冰片烷-2-羧酸甲酯的合成法)
使用具备磁力感应式搅拌机和位于上部的3个入口喷嘴的内容积500ml的不锈钢制高压釜进行氢甲酰化反应。
在前述高压釜中,加入上述中制备的降冰片烯-2-羧酸甲酯60.0g、甲苯116.9g、亚磷酸三苯酯0.37g、另行制备好的Rh(acac)(CO)2的甲苯溶液3.10g(浓度0.01wt%)。利用氮气和CO/H2混合气体的置换各进行3次后,用CO/H2混合气体将体系内加压,以100℃、2MPa进行5小时反应。反应结束后,进行反应液的气相色谱法分析,得到含有甲酰基降冰片烷-2-羧酸甲酯(5-甲酰基降冰片烷-2-羧酸甲酯和6-甲酰基降冰片烷-2-羧酸甲酯的混合物)69.0g的反应液186.9g。降冰片烯-2-羧酸甲酯基准的效果如下:收率96.2摩尔%、选择率100摩尔%。
用理论塔板数40级的旋转带蒸馏塔,对所得液体进行精馏(馏出温度112℃、真空度0.19kPa),结果得到在气相色谱法分析中为98.4GC%者63.5g(蒸馏收率90.7摩尔%)作为主馏部分。
对所得馏分用GC-MS进行分析,结果示出目标物的分子量182。
所得馏分与仅具有果味的香气的公知的果糖酯或仅具有玫瑰样香气的公知的醋酸香叶酯不同,其为兼有强烈的香瓜、猕猴桃样果味和新鲜的海洋调、和玫瑰样花香的新型香气,与其他公知的酯或醋酸香叶酯相比,有香气持续性优异的特征。
(具有认为是甘甜且浓厚的栀子花的花香感的水果型的香料组合物)
首先,制作表4所示的组成的香料组合物(对照品)。接着,在该对照品90质量份中加入上述中制备的甲酰基降冰片烷-2-羧酸甲酯10质量份,制作香料组合物。
所得香料组合物在基于调香师的香味评价中,确认为具有认为是甘甜且浓厚的栀子花的花香感的水果型的香味。
[表4]
配混成分 | 聚合份 |
苄醇 | 25 |
芳樟醇 | 20 |
ε-癸内酯 | 17 |
三环癸烷-2-羧酸乙酯 | 15 |
乙酸苄酯 | 5 |
乙酸异丁酯 | 3 |
丙二酸二乙酯 | 2 |
β-紫罗兰酮 | 2 |
柠檬烯 | 1 |
总计 | 90 |
本申请基于2016年9月15日申请的日本专利申请(特愿2016-180434号)、2016年9月15日申请的日本专利申请(特愿2016-180435号)、和2016年9月15日申请的日本专利申请(特愿2016-180436号),将其内容作为参照引入至此。
产业上的可利用性
本发明的具有降冰片烷骨架的羧酸酯化合物具备有果味的香气,且具有优异的香气持续性,因此,作为梳妆用品、肥皂、衣料用洗涤剂等宽范围的制品中的赋香成分是有用的。
Claims (3)
1.一种香料组合物,其含有式(1)所示的化合物;
式(1)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基,
R4和R5独立地为氢或-CHO基,
为单键或双键。
2.根据权利要求1所述的香料组合物,其中,式(1)所示的化合物为选自由以下的式(1-1)~式(1-3)组成的组中的1种以上,
式(1-1)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基,
式(1-2)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基,
式(1-3)中,R1、R2、R3独立地为氢或甲基,
X为碳数1~4的烷基,
R4和R5中的任一者为氢,另一者为-CHO基。
3.化妆品、健康卫生材料、杂货、饮料、食品、准药品或药品,其含有权利要求1或2所述的香料组合物。
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JP2016180435 | 2016-09-15 | ||
JP2016-180436 | 2016-09-15 | ||
JP2016180434 | 2016-09-15 | ||
PCT/JP2017/030796 WO2018051776A1 (ja) | 2016-09-15 | 2017-08-28 | 香料組成物 |
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EP (1) | EP3514221B1 (zh) |
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WO2020100708A1 (ja) * | 2018-11-16 | 2020-05-22 | 三菱瓦斯化学株式会社 | カルボン酸エステル化合物及びその製造方法、並びに香料組成物 |
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US11292988B2 (en) | 2020-01-15 | 2022-04-05 | Promerus, Llc | Fine fragrance compositions containing norbornene ester derivatives |
US11584899B2 (en) | 2020-01-15 | 2023-02-21 | Promerus, Llc | Fragrance compositions containing norbornene derivatives for personal care products |
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US11098267B2 (en) | 2021-08-24 |
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