CN113015717B - 羧酸酯化合物及其制造方法以及香料组合物 - Google Patents
羧酸酯化合物及其制造方法以及香料组合物 Download PDFInfo
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- CN113015717B CN113015717B CN201980074605.6A CN201980074605A CN113015717B CN 113015717 B CN113015717 B CN 113015717B CN 201980074605 A CN201980074605 A CN 201980074605A CN 113015717 B CN113015717 B CN 113015717B
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- -1 Carboxylic acid ester compound Chemical class 0.000 title claims abstract description 72
- 239000002304 perfume Substances 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 20
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 19
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 18
- 239000002994 raw material Substances 0.000 abstract description 15
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 235000013399 edible fruits Nutrition 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000003205 fragrance Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 238000005810 carbonylation reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- JURLNXPXCMWCHE-KRXBUXKQSA-N (3e)-3-ethylidenebicyclo[2.2.1]heptane Chemical compound C1CC2C(=C/C)/CC1C2 JURLNXPXCMWCHE-KRXBUXKQSA-N 0.000 description 14
- 238000005886 esterification reaction Methods 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 230000032050 esterification Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
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- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 230000006315 carbonylation Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
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- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
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- 150000001265 acyl fluorides Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
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- 229940079593 drug Drugs 0.000 description 4
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229940095102 methyl benzoate Drugs 0.000 description 4
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- VNYPXKJMCADQLD-UHFFFAOYSA-N ethyl 2-ethylbicyclo[2.2.1]heptane-2-carboxylate Chemical compound CCC1(CC2CCC1C2)C(=O)OCC VNYPXKJMCADQLD-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 3
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- LHXQHHJUVUCVBY-UHFFFAOYSA-N propan-2-yl 2-ethylbicyclo[2.2.1]heptane-2-carboxylate Chemical compound CCC1(CC2CCC1C2)C(=O)OC(C)C LHXQHHJUVUCVBY-UHFFFAOYSA-N 0.000 description 3
- CEPAPUSAKOIZMY-UHFFFAOYSA-N propyl 2-ethylbicyclo[2.2.1]heptane-2-carboxylate Chemical compound CCCOC(=O)C1(CC2CCC1C2)CC CEPAPUSAKOIZMY-UHFFFAOYSA-N 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
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- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 2
- 240000006927 Foeniculum vulgare Species 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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Abstract
本发明的技术问题是提供一种可用作调合香料原料的具有水果香气的羧酸酯化合物及其制造方法，并提供含有该羧酸酯化合物的香料组合物。本发明的羧酸酯化合物如式(1)所示(式中，R为碳数2～6的烷基)。
Description
技术领域
本发明涉及一种新型羧酸酯化合物及其制造方法以及含有该羧酸酯化合物的香料组合物，尤其涉及一种可用作调合香料原料的羧酸酯化合物及其制造方法以及含有该羧酸酯化合物的香料组合物。
背景技术
已知酯类中有可用作香料的化合物。例如，具有玫瑰般香气的乙酸香叶酯、具有茉莉般甜香的茉莉酸甲酯、具有水果香调的果香酯(三环[5.2.1.02,6]癸烷-2-羧酸乙酯)、具有强烈的干果香调的苯甲酸甲酯等可用作调合香料原料。另外，专利文献1记载了作为樟脑衍生物的羧酸酯化合物具有清爽的松树(Pine)般的香气。
现有技术文献
专利文献
专利文献1：国际公开第2012/063433号
发明内容
发明要解决的问题
本发明要解决的问题是提供一种可用作调合香料原料的、具有水果香气的新型羧酸酯化合物及其制造方法，并提供含有该羧酸酯化合物的香料组合物。
用于解决问题的方案
本发明人合成了各种化合物，并对其香气进行了研究后发现，特定的羧酸酯化合物具有水果香气，由此完成了本发明。
本发明提供以下的<1>～<4>。
＜1＞一种羧酸酯化合物，其如式(1)所示。
(式中，R为碳数2～6的烷基。)
＜2＞根据上述＜1＞所述的羧酸酯化合物，其中，R为乙基、正丙基或异丙基。
＜3＞一种香料组合物，其含有如式(1)所示的羧酸酯化合物。
(式中，R为碳数2～6的烷基。)
＜4＞一种如式(1)所示的羧酸酯化合物的制造方法，其中，在氟化氢的存在下，使如式(2)所示的化合物与一氧化碳反应，接着与碳数2～6的醇反应。
(式中，R为碳数2～6的烷基。)
发明的效果
本发明的羧酸酯化合物具有水果香气，可作为卫生间用品、皂类，衣物用洗剂等广泛的产品中的赋香成分使用。另外，根据本发明的羧酸酯化合物的制造方法，可通过工业上有利的方法制造该羧酸酯化合物。
具体实施方式
以下，用实施方式对本发明进行说明。需要说明的是，以下的说明中，表示数值范围的“A～B”的表述表示“A以上且B以下”(A＜B的情况)，或表示“A以下且B以上”(A＞B的情况)。即，表示包括端点A和B在内的数值范围。
另外，质量份和质量％分别与重量份和重量％同义。
[羧酸酯化合物]
本发明的羧酸酯化合物如下述式(1)所示。
(式中，R为碳数2～6的烷基。)
式(1)中，R为碳数2～6的烷基。作为碳数2～6的烷基，优选为直链状或支链状的烷基，可列举出乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、戊基、己基等。其中，从香气性的角度出发，优选为乙基、正丙基、异丙基，更优选为乙基。
如式(1)所示的羧酸酯化合物具有空间异构体，可以是Exo型，也可以是Endo型，并且Exo型和Endo型可以以任意比率混合，并不特别限定。
其中，从易制造性和香气性的角度出发，优选为Exo型。
[羧酸酯化合物的制造方法]
本发明的羧酸酯化合物(如式(1)所示的羧酸酯化合物)可通过以下方法在工业上有利地制造：在氟化氢(以下也称为“HF”)的存在下，使如式(2)所示的化合物与一氧化碳反应，接着与碳数2～6的醇反应。
具体而言，在氟化氢(HF)的存在下，使如式(2)所示的化合物与一氧化碳反应而羰基化，得到如式(3)所示的酰氟。并且，在氟化氢的存在下，使如式(3)所示的酰氟与碳数2～6的醇反应而酯化。
(式中，R为碳数2～6的烷基。)
(如式(2)所示的化合物)
如式(2)所示的化合物为2-亚乙基降冰片烷，可通过使5-亚乙基-2-降冰片烯(ENB)氢化而得到。需要说明的是，ENB作为三元乙丙橡胶(EPDM)的原料被广泛知晓。
(一氧化碳)
本发明中使用的一氧化碳可以含有氮气、甲烷等非活性气体。反应时的一氧化碳分压优选为0.5～5MPaG，更优选为1～3MPaG的范围。一氧化碳分压高于0.5MPaG时，羰基化反应充分进行，不发生歧化、聚合等副反应，能够高收率地得到作为目标物的脂环式羰基化合物。另外，从设备负荷的角度出发，一氧化碳分压优选为5MPaG以下。
(氟化氢)
本发明中使用的HF由于是反应的溶剂、催化剂且作为原料，因此优选使用基本无水的产品。相对于作为原料的如式(2)所示的化合物，HF的用量优选为4～25摩尔倍，更优选为6～15摩尔倍。HF的摩尔比为4摩尔倍以上时，羰基化反应高效率地进行，可以抑制歧化、聚合等副反应，能够高收率地得到作为目标物的羰基化合物。另外，从原料成本和生产率的角度出发，优选使用25摩尔倍以下的HF。
(反应溶剂)
羰基化反应中，可以使用原料溶解良好、对HF呈非活性的溶剂。例如可以使用己烷、庚烷、癸烷之类的饱和烃化合物。是否使用溶剂及其用量并不特别限定，适当选择即可，从抑制聚合反应、提高收率的角度出发，相对于作为原料的式(2)的化合物，优选为0.2～2.0质量倍，从生产率和能量效率的角度出发，优选为0.5～1.2质量倍。
(羰基化反应的反应条件)
羰基化反应的形式并无特别限制，可以是分批式、半连续式、连续式等任意一种方式。
羰基化反应的反应温度优选为-50℃～30℃，更优选为-30℃～20℃的范围。从反应速度的角度出发，优选在-50℃以上进行。另外，从抑制异构体生成量的角度出发，优选在30℃以下进行。
羰基化反应的反应时间从使反应充分进行的角度出发优选为1小时以上，并且从反应效率的角度出发优选为5小时以下。反应终点并不特别限定，例如可以是一氧化碳吸收停止的时间点。
羰基化反应中，由HF和一氧化碳生成酰氟(式(3))。对于生成的酰氟反应液(羰基化反应液)，虽然也可以将多余的HF蒸馏去除后，通过蒸馏等常规方法进行纯化，作为下一工序即酯化工序的原料使用，但通常采用使含HF催化剂在内的羰基化反应液直接与醇反应来制造羧酸酯化合物的方法。
(醇)
本发明中使用的醇为碳数2～6的醇。
作为碳数2～6的醇，并无特别限制，可根据目的适当选择，例如，可列举出乙醇、正丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、戊醇、己醇。其中，优选为乙醇、正丙醇、异丙醇、正丁醇、异丁醇，更优选为乙醇、正丙醇、异丙醇，进一步优选为乙醇。
碳数2～6的醇的用量并无特别限制，可根据目的适当选择，相对于作为原料的式(2)的化合物，优选为0.5～2.0倍摩尔，更优选为0.8～1.7倍摩尔，进一步优选为1.0～1.7倍摩尔。
(酯化反应的反应条件)
酯化反应的反应温度从提高收率的角度出发优选为-20℃以上，并且从抑制酯分解和抑制所添加的醇的脱水反应等副反应的角度出发优选为20℃以下。
酯化反应的反应时间从使反应充分进行的角度出发优选为0.5小时以上，并且从反应效率的角度出发优选为3小时以下。反应终点并不特别限定，例如可以是不再观察到反应热上升的时间点。
由此得到的酯化产物为羧酸酯·HF络合物溶液。通过加热羧酸酯·HF络合物溶液，羧酸酯和HF之间的键分解，可以使HF气化分离，并回收再利用。该络合物的分解操作需要尽量快速地进行，避免产物加热变质、异构化等。为了快速地进行络合物的热分解，例如优选在对HF呈非活性的溶剂(例如庚烷等饱和脂肪族烃、甲苯等芳香族烃)回流下进行分解。另外，如果将反应液抽取至冰水中，则优选例如从高压釜底部抽液至冰水中，使油相和水相分离后，将油相用2质量％氢氧化钠水溶液清洗2次，用蒸馏水清洗2次，用无水硫酸钠进行脱水。进而，将得到的液体用蒸发器去除低沸物等之后，使用理论级数20级左右的精馏塔进行精馏，可得到纯化的羧酸酯化合物。
需要说明的是，本发明的羧酸酯化合物也可以通过上述以外的方法制造。例如，如下述方案所示，可通过使由环戊二烯和2-乙基丙烯醛的狄尔斯-阿尔德反应得到的醛化合物(式(4))氧化，得到羧酸化合物(式(5))，使该羧酸化合物与碳数2～6的醇反应而得到酯化合物(式(6))，使该酯化合物氢化，得到本发明的羧酸酯化合物(如式(1)所示的羧酸酯化合物)。另外，如式(5)所示的羧酸化合物也可以通过环戊二烯和2-乙基丙烯酸(2-亚甲基丁酸)的狄尔斯-阿尔德反应得到。
(式中，R为碳数2～6的烷基。)
本发明的羧酸酯化合物由于具有水果香气，可单独或与其它成分组合，作为皂类、洗发水、护发素、洗涤剂、化妆品、喷雾产品、芳香剂、香水、泡浴剂等的赋香成分使用。另外，可期待作为食品、医药、农药、液晶等的合成中间体使用。
[香料组合物]
本发明的香料组合物含有如所述式(1)所示的羧酸酯化合物。
本发明的香料组合物是在通常使用的其它香料成分或期望组成的调合香料中，单独添加或混配2种以上如所述式(1)所示的羧酸酯化合物而得到。如所述式(1)所示的羧酸酯化合物的配混量根据调合香料的种类、目标香气的种类以及香气的强度等而不同，优选在调合香料中加入0.01～90质量％，更优选加入0.1～50质量％。
作为可与本发明的羧酸酯化合物组合使用的其它香料成分，并无特别限制，可根据目的适当选择。例如，可列举出：
柠檬烯、α-蒎烯、β-蒎烯、萜品烯、柏木烯、长叶烯、凡伦橘烯等烃类；
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、雪松醇、薄荷醇、龙脑、β-苯乙醇、苯甲醇、苯己醇、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、异氟醚环己醇、3,7-二甲基-7-甲氧基辛烷-2-醇等醇类；
丁香油酚、百里香酚、香草醛等酚类；
甲酸芳樟酯、甲酸香茅酯、甲酸香叶酯、乙酸正己酯、乙酸顺式-3-己烯酯、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、乙酸诺吡酯、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、乙酸苯乙烯酯、乙酸肉桂酯、二甲基苄基原醇乙酯、3-戊基四氢吡喃-4-基乙酸酯、丙酸香茅酯、丙酸三环癸烯酯、环己基丙酸烯丙基酯、2-环己基丙酸乙酯、丙酸苄酯、丁酸香茅酯、正丁酸二甲基苄基原醇酯、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、惕各酸顺式-3-己烯酯、茉莉酸甲酯、茉莉酸二氢甲酯、2,4-二羟基-3,6-二甲基苯甲酸甲酯、杨梅醛、邻氨基苯甲酸甲酯、果香酯等酯类；
正辛醛、正癸醛、正十二醛、2-甲基十一醛、10-十一烯醛、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-甲醛、2-环己基丙醛、对叔丁基-α-甲基氢化肉桂醛、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、茴香酮、甲基β-萘基酮、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、环十七酮、环十五酮、环十六烯酮等酮类；
乙醛乙苯丙缩醛、柠檬醛二乙缩醛、苯乙醛甘油缩醛、乙基乙酰乙酸酯乙二醇缩酮类的缩醛类和缩酮类；
茴香烯、β-萘基甲基醚、β-萘基乙基醚、柠檬醚、玫瑰醚、1,8-桉叶素、外消旋或旋光的十二氢-3a,6,6,9a-四甲基萘[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、巴西酸亚乙酯、11-氧十六内酯等内酯类；
橙、柠檬、佛手柑、柑橘、椒样薄荷、绿薄荷、薰衣草、甘菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、天竺葵、茉莉、依兰、茴香、丁香、姜、肉豆蔻、豆蔻、雪松、扁柏、香根草、广藿香、岩蔷薇等天然精油或天然提取物等；
等等。需要说明的是，所述其它香料成分可单独添加或混配多种。
含有如所述式(1)所示的羧酸酯化合物的香料组合物由于如式(1)所示的羧酸酯化合物带来优异的水果香气，可作为香妆品类、健康卫生材料、杂货、食品、类药品、药品等各种产品的香气成分使用，以对配混对象的香气进行改良。
含有如所述式(1)所示的羧酸酯化合物的香料组合物可作为例如香水、古龙水类等香水类产品；洗发水、护发素类、养发剂、发膏类、美发慕丝、发胶、润发油、发用喷雾以及其它毛发用化妆品；化妆水、美容液、乳霜、乳液、面膜、粉底、卸妆水、口红、各种化妆类等皮肤用化妆品；洗碗剂、洗衣液、柔顺剂类、消毒用洗涤剂类、消臭洗涤剂类、室内芳香剂、家具护理剂、玻璃清洁剂、家具清洁剂、床清洁剂、消毒剂、殺虫剂、漂白剂、其它各种健康卫生用洗涤剂类；牙膏、漱口水、泡浴剂、止汗类产品、烫发液等类药品；卫生纸、餐巾纸等杂货；药品等；食品等产品的香气成分使用。
另外，本发明的香料组合物在产品中的配混量并无特别限制，可根据目的适当选择，但以如所述式(1)所示的羧酸酯化合物在产品中的配混量计优选为0.001～50质量％，更优选为0.01～20质量％。
实施例
以下，用实施例和比较例对本发明进行更具体的说明，但本发明不限于这些实施例。
＜气相色谱法分析条件＞
气相色谱法使用气相色谱仪(株式会社岛津制作所制，“GC-2010Plus”)和毛细管柱(信和化工株式会社制，“HR-1”(0.32mmφ×25m))。升温条件为以5℃/分钟从100℃升温至310℃。
＜GC-MS＞
使用日本电子株式会社制GC-MS谱图仪JMS-T100GCV。
＜1H-NMR，13C-NMR谱图分析＞
基于以下条件进行测定。
装置：日本电子株式会社制NMR谱图仪JNM-ECA500
内部标准物质：四甲基硅烷(TMS)
＜羧酸酯化合物收率、异构体比＞
·羧酸酯化合物收率(摩尔％)＝(羧酸酯化合物的摩尔数)/(2-亚乙基降冰片烷的摩尔数)×100
·异构体比(％)＝(2-乙基降冰片烷-Exo-2-羧酸酯的摩尔数)/(羧酸酯化合物总和的摩尔数)×100
合成例1
(通过5-亚乙基-2-降冰片烯(ENB)的氢化来制备2-亚乙基降冰片烷)
向具备磁感应式搅拌机、并在上部有3个入口喷嘴、在底部有1个抽取喷嘴、可通过夹套调节内部温度的内容积200mL的不锈钢制高压釜中，投入Cu-Cr系催化剂(日挥催化剂化成株式会社制，“N-203S”)2.0g、庚烷(和光纯药工业株式会社制，特级)30g，在170℃、1MPaG氢气压力下进行1小时的活化。冷却后，投入5-亚乙基-2-降冰片烯(东京化成工业株式会社制)100g，在90℃、2MPaG氢气压力下搅拌2小时进行氢化反应，过滤反应液而去除催化剂，将溶剂庚烷蒸馏去除，得到含有2-亚乙基降冰片烷浓度95质量％、2-乙基降冰片烷浓度5质量％的液态反应产物(以下也称为“反应液”)89g(收率88摩尔％(需要说明的是，收率由2-亚乙基降冰片烷和2-乙基降冰片烷的总摩尔数与作为原料的5-亚乙基-2-降冰片烯的摩尔数的比来计算得出))。另外，2-亚乙基降冰片烷的收率为84摩尔％(由2-亚乙基降冰片烷的摩尔数与作为原料的5-亚乙基-2-降冰片烯的摩尔数的比来计算得出)。
反应式如下所示。
实施例1
(由2-亚乙基降冰片烷的羰基化和酯化来制造2-乙基降冰片烷-2-羧酸乙酯)
使用可通过夹套抑制内部温度的内容积500ml的不锈钢制高压釜进行实验，该不锈钢制高压釜具备磁感应式搅拌机，并在上部具有3个入口喷嘴，在底部具有1个抽取喷嘴。
首先，将高压釜内部用一氧化碳置换后，导入氟化氢158g(7.9摩尔)，使液温达到0℃后，用一氧化碳加压至2MPaG。
一边将反应温度保持在0℃，且将反应压力保持在2MPaG，一边将合成例1中制备的反应液(2-亚乙基降冰片烷浓度95质量％，2-乙基降冰片烷浓度5质量％)82g与庚烷(和光纯药工业株式会社制，特级)82g的混合液从高压釜上部用60分钟进料，进行羰基化反应。原料的进料结束后，继续搅拌约20分钟，直到不再观察到一氧化碳的吸收。
接着，一边将反应温度保持在0℃，一边将乙醇46g(1.0摩尔，相对于作为原料的2-亚乙基降冰片烷为1.6摩尔倍)从高压釜上部用15分钟进料，在搅拌下进行1小时酯化。将反应液从高压釜底部抽取至冰水中，将油相与水相分离后，将油相用2质量％氢氧化钠水溶液100mL清洗2次，用蒸馏水100mL清洗2次，用无水硫酸钠10g进行脱水。
将得到的液体用蒸发器除去低沸物后，使用理论级数20级的精馏塔进行精馏(馏出温度150℃，真空度60托)后，基于内部标准法用气相色谱法进行分析。其结果是，羧酸酯化合物(Exo型和Endo型的混合物)的收率为94.1摩尔％(相对于2-亚乙基降冰片烷)。另外，作为主产物的2-乙基降冰片烷-2-exo-羧酸乙酯的收率为84.9摩尔％(相对于2-亚乙基降冰片烷；异构体比90.3％)。
对主产物用GC-MS(CI+)进行分析的结果为：相对于目标物的分子量196.29，显示为197.15([M+H]+)。另外，在氘代氯仿溶剂中的1H-NMR的化学位移值以及13C-NMR的化学位移值(δppm，相对于TMS)如下，由该结果确定为2-乙基降冰片烷-2-羧酸乙酯。需要说明的是，在NMR测定中，[2]在下述化学式中表示带有符号2的碳原子或与该碳原子键合的氢原子。下同。
1H NMR(500MHz，CDCl3)δ(ppm):0.76(t，J＝7.5Hz，3H，[9])，0.90(dd，J＝12.5，3.0Hz，1H，[5a<endo>])，1.06-1.11(m，1H，[7a<endo>])，1.19-1.21(m，1H，[3b])，1.23(t，J＝7.0Hz，3H，[13])，1.28-1.32(m，1H，[3a])，1.33-1.41(m，1H，[6a<endo>])，1.45-1.50(m，1H，[7b<exo>])，1.51-1.58(m，1H，[6b<exo>])，1.58-1.64(m，2H，[8])，2.17-2.19(m，1H，[4])，2.20-2.24(m，1H，[5b<exo>])，2.54(br d，J＝4.0，1H，[2])，4.09-4.13(m，2H，[12])
13C NMR(126MHz，CDCl3)δ(ppm):10.55[9]，14.37[13]，23.15[6]，29.05[7]，29.60[8]，36.81[4]，38.81[3]，41.29[5]，42.78[2]，54.35[1]，60.27[12]，178.06[10]
2-乙基降冰片烷-2-羧酸乙酯具有果香基调且带有青草、原木般(fruity-herbal-woody)的香气。
实施例2
(由2-亚乙基降冰片烷的羰基化和酯化来制造2-乙基降冰片烷-2-羧酸正丙酯)
除了将实施例1的酯化中使用的醇替换为正丙醇以外，与实施例1同样地进行羰基化和酯化以及反应生成液的处理。
用气相色谱法进行分析，结果是羧酸酯化合物的收率为92.9摩尔％(相对于2-亚乙基降冰片烷)，作为主产物的2-乙基降冰片烷-exo-2-羧酸正丙酯的收率为83.0摩尔％(相对于2-亚乙基降冰片烷；异构体比89.4％)。
对主产物用GC-MS(CI+)进行分析的结果为：相对于目标物的分子量210.32，显示为211.13([M+H]+)。另外，在氘代氯仿溶剂中的1H-NMR的化学位移值以及13C-NMR的化学位移值(δppm，相对于TMS)如下，由该结果确定为2-乙基降冰片烷-2-羧酸正丙酯。
1H NMR(500MHz，CDCl3)δ(ppm):0.76(t，J＝7.5Hz，3H，[9])，0.89-0.92(m，1H，[5b<endo>])，0.93(t，J＝7.0Hz，3H，[14])，1.05-1.11(m，1H，[7a<endo>])，1.18-1.22(m，1H，[3b])，1.27-1.32(m，1H，[3a])，1.33-1.40(m，1H，[6b<endo>])，1.45-1.51(m，1H，[7b<exo>])，1.52-1.59(m，1H，[6a<exo>])，1.60-1.67(m，4H，[13]，[8])，2.17-2.19(m，1H，[4])，2.20-2.24(m，1H，[5a<exo>])，2.54(br d，J＝3.5Hz，1H，[2])，4.98-4.05(m，2H，[12])
13C NMR(126MHz，CDCl3)δ(ppm):10.59[9，14]，22.16[13]，23.16[6]，29.06[7]，29.64[8]，36.82[4]，38.82[3]，41.30[5]，42.80[2]，54.52[1]，65.98[12]，178.14[10]
另外，2-乙基降冰片烷-2-羧酸正丙酯具有果香基调且带有原木般、青草般(fruity-woody-herbal)的香气。
实施例3
(由2-亚乙基降冰片烷的羰基化和酯化来制造2-乙基降冰片烷-2-羧酸异丙酯)
除了将实施例1的酯化中使用的醇替换为异丙醇以外，与实施例1同样地进行羰基化和酯化以及反应生成液的处理。
用气相色谱法进行分析，结果是羧酸酯化合物的收率为92.4摩尔％(相对于2-亚乙基降冰片烷)，作为主产物的2-乙基降冰片烷-2-exo-羧酸异丙基的收率为81.2摩尔％(相对于2-亚乙基降冰片烷；异构体比87.9％)。
对主产物用GC-MS(CI+)进行分析的结果为：相对于目标物的分子量210.32，显示为211.12([M+H]+)。另外，在氘代氯仿溶剂中的1H-NMR的化学位移值以及13C-NMR的化学位移值(δppm，相对于TMS)如下，由该结果确定为2-乙基降冰片烷-2-羧酸异丙酯。
1H NMR(500MHz，CDCl3)δ(ppm):0.76(t，J＝7.0Hz，3H，[9])，0.87-0.90(m，1H，[5b<endo>])，1.05-1.11(m，1H，[7a<endo>])，1.19-1.21(m，7H，[3b]，[13]，[15])，1.29-1.30(m，1H，[3a])，1.33-1.39(m，1H，[6b<endo>])，1.45-1.51(m，1H，[7b<exo>])，1.51-1.56(m，1H，[6a<exo>])，1.56-1.64(m，2H，[8])，2.16-2.19(m，1H，[4])，2.19-2.22(m，1H，[5a<exo>])，2.54(br d，J＝4.0Hz，1H，[2])，4.96-5.01(m，1H，[12])
13C NMR(126MHz，CDCl3)δ(ppm):10.47[9]，21.85-21.88[13]，[15]，23.16[6]，29.08[7]，29.53[8]，36.80[4]，38.74[3]，41.25[5]，42.79[2]，54.25[1]，67.22[12]，177.49[10]
另外，2-乙基降冰片烷-2-羧酸异丙酯具有草香基调且带有水果般、苹果般、原木般(herbal-fruity-apple-woody)的香气。
实施例4
(香料组合物)
按照下述表1的配方，用实施例1中得到的羧酸酯化合物制备花香-果香调香料组合物。
[表1]
官能评价由具有5年以上经验的4人的专业小组来进行，其结果，小组全员认为：含有实施例1的化合物的花香-果香调香料组合物具有强烈的果香调香气，喜好度高，且在扩散性方面也优异。
产业上的可利用性
本发明的新型羧酸酯化合物具有水果香气，具有优异的香气性，因此可作为有效的赋香成分广泛用于卫生间用品、皂类、衣物用洗涤剂等。另外，根据本发明的羧酸酯化合物的制造方法，可通过工业上有利的方法制造该羧酸酯化合物。
Claims (3)
1.一种羧酸酯化合物，其如下述式(1)所示，
式中，R为乙基或正丙基，所述羧酸酯化合物为Exo体。
2.一种香料组合物，其含有如式(1)所示的羧酸酯化合物，
式中，R为乙基或正丙基。
3.一种如式(1)所示的羧酸酯化合物的制造方法，其中，在氟化氢的存在下，使如式(2)所示的化合物与一氧化碳反应，接着与乙醇或正丙醇反应，
式中，R为乙基或正丙基，所述羧酸酯化合物为Exo体。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018-216004 | 2018-11-16 | ||
| JP2018216004 | 2018-11-16 | ||
| PCT/JP2019/043662 WO2020100708A1 (ja) | 2018-11-16 | 2019-11-07 | 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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| CN113015717A CN113015717A (zh) | 2021-06-22 |
| CN113015717B true CN113015717B (zh) | 2024-04-30 |
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| EP (1) | EP3882233B1 (zh) |
| JP (1) | JP7351313B2 (zh) |
| KR (1) | KR20210092727A (zh) |
| CN (1) | CN113015717B (zh) |
| ES (1) | ES2936714T3 (zh) |
| TW (1) | TWI821449B (zh) |
| WO (1) | WO2020100708A1 (zh) |
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| US4319036A (en) * | 1980-03-25 | 1982-03-09 | International Flavors & Fragrances Inc. | Carboalkoxy alkyl norbornanes and process for preparing same |
| JPS60190738A (ja) * | 1984-03-09 | 1985-09-28 | Kao Corp | 香料組成物 |
| CN103201250A (zh) * | 2010-11-12 | 2013-07-10 | 三菱瓦斯化学株式会社 | 新型羧酸酯化合物及其制造方法以及其香料组合物 |
| CN103415500A (zh) * | 2011-03-25 | 2013-11-27 | 三菱瓦斯化学株式会社 | 新型的羧酸酯化合物及其制造方法、以及香料组合物 |
| WO2018051776A1 (ja) * | 2016-09-15 | 2018-03-22 | 三菱瓦斯化学株式会社 | 香料組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4347858A (en) | 1980-03-25 | 1982-09-07 | International Flavors & Fragrances Inc. | Use of carboalkoxy alkyl norbornanes for augmenting or enhancing the aroma or taste of a smoking tobacco composition or at least a portion of a smoking tobacco article |
| US4310681A (en) | 1980-03-25 | 1982-01-12 | International Flavors & Fragrances Inc. | Carboalkoxy alkyl norbornane derivatives and process for preparing same |
| US4350823A (en) | 1980-03-25 | 1982-09-21 | International Flavors & Fragrances Inc. | Carbomethoxy methyl norbornanes |
| US4386064A (en) | 1980-03-25 | 1983-05-31 | International Flavors & Fragrances Inc. | Flavoring with carbomethoxy methyl norbornanes |
| EP0037644A1 (en) * | 1980-03-25 | 1981-10-14 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Carbonyl norbornanes, organoleptic uses thereof and processes for preparing same |
| US4374054A (en) | 1980-03-25 | 1983-02-15 | International Flavors & Fragrances Inc. | Use in perfumery of carboalkoxy alkyl norbornanes |
| US4312888A (en) | 1980-03-25 | 1982-01-26 | International Flavors & Fragrances Inc. | Flavoring with carboalkoxy alkyl norbornanes |
| US4395366A (en) | 1980-03-25 | 1983-07-26 | International Flavors & Fragrances Inc. | Carbomethoxy methyl norbornanes, organoleptic uses thereof and process for preparing same |
| US4357246A (en) | 1980-03-25 | 1982-11-02 | International Flavors & Fragrances Inc. | Carboalkoxy alkyl norbornanes, organoleptic uses thereof and process for preparing same |
| US4367158A (en) * | 1980-10-23 | 1983-01-04 | International Flavors & Fragrances Inc. | Use of norbornyl ethers in augmenting or enhancing the aroma of detergents |
| US4357253A (en) | 1980-11-13 | 1982-11-02 | International Flavors & Fragrances Inc. | Process of enhancing or augmenting the aroma of detergents using norbornyl esters |
| US4431577A (en) | 1981-07-16 | 1984-02-14 | International Flavors & Fragrances Inc. | Carbomethoxy methyl norbornanes, organoleptic uses thereof and process for preparing same |
| GB2383049A (en) * | 2000-11-13 | 2003-06-18 | Rhodia Cons Spec Ltd | Tannages |
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2019
- 2019-11-07 CN CN201980074605.6A patent/CN113015717B/zh active Active
- 2019-11-07 JP JP2020555581A patent/JP7351313B2/ja active Active
- 2019-11-07 US US17/291,022 patent/US11725161B2/en active Active
- 2019-11-07 KR KR1020217013041A patent/KR20210092727A/ko unknown
- 2019-11-07 EP EP19884807.9A patent/EP3882233B1/en active Active
- 2019-11-07 WO PCT/JP2019/043662 patent/WO2020100708A1/ja active Application Filing
- 2019-11-07 ES ES19884807T patent/ES2936714T3/es active Active
- 2019-11-08 TW TW108140578A patent/TWI821449B/zh active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4319036A (en) * | 1980-03-25 | 1982-03-09 | International Flavors & Fragrances Inc. | Carboalkoxy alkyl norbornanes and process for preparing same |
| JPS60190738A (ja) * | 1984-03-09 | 1985-09-28 | Kao Corp | 香料組成物 |
| CN103201250A (zh) * | 2010-11-12 | 2013-07-10 | 三菱瓦斯化学株式会社 | 新型羧酸酯化合物及其制造方法以及其香料组合物 |
| CN103415500A (zh) * | 2011-03-25 | 2013-11-27 | 三菱瓦斯化学株式会社 | 新型的羧酸酯化合物及其制造方法、以及香料组合物 |
| WO2018051776A1 (ja) * | 2016-09-15 | 2018-03-22 | 三菱瓦斯化学株式会社 | 香料組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020100708A1 (ja) | 2020-05-22 |
| TW202033488A (zh) | 2020-09-16 |
| JP7351313B2 (ja) | 2023-09-27 |
| KR20210092727A (ko) | 2021-07-26 |
| TWI821449B (zh) | 2023-11-11 |
| US11725161B2 (en) | 2023-08-15 |
| US20220041955A1 (en) | 2022-02-10 |
| EP3882233A1 (en) | 2021-09-22 |
| CN113015717A (zh) | 2021-06-22 |
| ES2936714T3 (es) | 2023-03-21 |
| EP3882233A4 (en) | 2022-03-30 |
| JPWO2020100708A1 (ja) | 2021-10-14 |
| EP3882233B1 (en) | 2023-01-11 |
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