CN111051483A - 用作芳香化学品的2,2,4,4-四甲基环丁烷-1,3-二醇的酯和醚 - Google Patents
用作芳香化学品的2,2,4,4-四甲基环丁烷-1,3-二醇的酯和醚 Download PDFInfo
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- CN111051483A CN111051483A CN201880057849.9A CN201880057849A CN111051483A CN 111051483 A CN111051483 A CN 111051483A CN 201880057849 A CN201880057849 A CN 201880057849A CN 111051483 A CN111051483 A CN 111051483A
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- 239000003205 fragrance Substances 0.000 title claims abstract description 89
- 239000000126 substance Substances 0.000 title claims abstract description 86
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 title claims description 53
- 150000002148 esters Chemical class 0.000 title abstract description 28
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- 238000002360 preparation method Methods 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims description 52
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- 238000000746 purification Methods 0.000 claims description 28
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 150000008064 anhydrides Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 15
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- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 10
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- 229910000104 sodium hydride Inorganic materials 0.000 description 10
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- INCLPCMHSAPRGR-UHFFFAOYSA-N (3-acetyloxy-2,2,4,4-tetramethylcyclobutyl) acetate Chemical compound CC(=O)OC1C(C)(C)C(OC(C)=O)C1(C)C INCLPCMHSAPRGR-UHFFFAOYSA-N 0.000 description 9
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- KCZZNAJDCVQMTK-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2,4-di(propan-2-yloxy)cyclobutane Chemical compound CC(C)OC1C(C)(C)C(OC(C)C)C1(C)C KCZZNAJDCVQMTK-UHFFFAOYSA-N 0.000 description 6
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- 150000003626 triacylglycerols Chemical class 0.000 description 1
- WKSPQBFDRTUGEF-UHFFFAOYSA-N tridec-2-enenitrile Chemical compound CCCCCCCCCCC=CC#N WKSPQBFDRTUGEF-UHFFFAOYSA-N 0.000 description 1
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- 239000013638 trimer Substances 0.000 description 1
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- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
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- 235000012141 vanillin Nutrition 0.000 description 1
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- RGVQNSFGUOIKFF-UHFFFAOYSA-N verdyl acetate Chemical compound C12CC=CC2C2CC(OC(=O)C)C1C2 RGVQNSFGUOIKFF-UHFFFAOYSA-N 0.000 description 1
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- 235000013343 vitamin Nutrition 0.000 description 1
- 239000001529 viverra civetta schreber and viverra zibeth a schreber absolute Substances 0.000 description 1
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- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
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- WGPCZPLRVAWXPW-UHFFFAOYSA-N xi-Dihydro-5-octyl-2(3H)-furanone Chemical compound CCCCCCCCC1CCC(=O)O1 WGPCZPLRVAWXPW-UHFFFAOYSA-N 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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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
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/184—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring to a carbon atom of a non-condensed ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/04—Formic acid esters
- C07C69/08—Formic acid esters of dihydroxylic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
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- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
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- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
本发明涉及通式(I)化合物、其立体异构体或其立体异构体的混合物作为芳香化学品的用途,R1为C1‑C4烷基或‑(C=O)‑R3,R2为氢、C1‑C4烷基或‑(C=O)‑R4,且R3和R4相互独立地选自氢和C1‑C4烷基,涉及包含至少一种通式(I)化合物、其立体异构体或其立体异构体的混合物的芳香化学品组合物,和制备加香即用组合物的方法,其包括将至少一种通式(I)化合物、其立体异构体或其立体异构体的混合物结合到即用组合物中。本发明进一步涉及通式(I)化合物的具体醚和具体酯,及其制备方法。
Description
本发明涉及2,2,4,4-四甲基环丁烷-1,3-二醇的酯和醚作为芳香化学品的用途,包含至少一种2,2,4,4-四甲基环丁烷-1,3-二醇的酯或醚的芳香化学品组合物,和制备加香即用组合物的方法,其包括将至少一种2,2,4,4-四甲基环丁烷-1,3-二醇的酯或醚结合到即用组合物中。本发明进一步涉及2,2,4,4-四甲基环丁烷-1,3-二醇的具体醚和具体酯及其制备方法。
发明背景
芳香化学品,尤其是芳香剂,尤其在化妆品以及清洁和洗衣组合物领域中是很重要的。天然来源的芳香剂多数是昂贵的,通常在其可得量方面是有限的,并且由于环境条件的波动,还遭遇其含量、纯度等的变化。为避免这些不理想的因素,因此很有意义的是产生具有类似于较昂贵的天然芳香剂的感官性能或者具有新和有意义的感官特征的合成物质。
尽管大量已经存在的合成芳香化学品(芳香剂和香料),仍需要新的组分以便能够满足极其多样的应用领域所需的大量性能。这些首先包括感官性能,即化合物应当具有有利的气味(嗅觉)或味觉性能。然而,此外,芳香化学品还应当具有其它积极的第二性能,例如,有效的制备方法、由于与其它芳香剂的协同效果而提供较好感觉特征的可能性、在某些应用条件下较高的稳定性、较高的可延伸性、较高的持久力等。
然而,由于甚至小的化学结构变化产生感觉性能如气味以及味道的大变化,关于具有特定感觉性能如特定气味的目标研究是极困难的。因此,在多数情况下,关于新芳香剂和香料的研究是困难且费力的,甚至不知道实际上是否会找到具有所需气味和/或味道的物质。
DE 1114811描述了二酯的制备方法,其中使脂族羧酸或苯甲酸与2,2,4,4-四甲基环丁烷-1,3-二醇、2,4-二甲基-2,4-二乙基环丁烷-1,3-二醇或2,2,4,4-四乙基环丁烷-1,3-二醇反应,以及所述酯作为润滑剂、增塑剂、传热油和液压流体的用途。
DE 1142695描述了使用可由脂族羧酸或苯甲酸和2,2,4,4-四甲基环丁烷-1,3-二醇、2,4-二甲基-2,4-二乙基环丁烷-1,3-二醇或2,2,4,4-四乙基环丁烷-1,3-二醇得到的二酯作为增塑剂将纤维素酯增塑的方法。
US 3,043,791描述了使用可由(C1-C4)羧酸和2,2,4,4-四甲基环丁烷-1,3-二醇、2,4-二甲基-2,4-二乙基环丁烷-1,3-二醇或2,2,4,4-四乙基环丁烷-1,3-二醇得到的二酯作为聚氯乙烯的增塑剂的用途和包含聚氯乙烯和所述二酯的塑料组合物。
US 3,062,852描述了可由脂族羧酸和2,2,4,4-四-(C1-C4)烷基环丁烷-1,3-二醇得到的二酯,和所述二酯作为合成润滑剂的用途。
US 3,227,764描述了将2,2,4,4-四-(C1-C4)烷基环丁烷-1,3-二醇,特别是2,2,4,4-四甲基环丁烷-1,3-二醇分离成它的顺式和反式异构体的方法,其中使所述二醇与(C1-C9)羧酸反应以得到相应的二酯,由于其不同的熔融温度,然后可将其分离成单独的顺式和反式异构体,并再转换成2,2,4,4-四甲基环丁烷-1,3-二醇的相应顺式和反式异构体。
迄今为止,现有技术中没有描述2,2,4,4-四甲基环丁烷-1,3-二醇的酯和醚作为芳香化学品的用途。
发明概述
本发明的目的是提供显示出愉悦的感官性能并且可有利地用作芳香化学品的物质。本发明的另一目的是提供可作为芳香化学品用于即用组合物中的物质。特别是,寻求具有愉悦气味的气味强烈物质。此外,这些芳香化学品应当可与其它芳香化学品组合,容许产生新的有利感觉特征。另外,这些芳香化学品应当可由容易得到的原料得到,容许它们的快速且经济的生产,并且应当不会有毒物学顾虑。
惊讶地发现,这些和其它目的通过2,2,4,4-四甲基环丁烷-1,3-二醇的酯和醚实现。
因此,本发明的第一方面涉及通式(I)化合物、其立体异构体或其立体异构体的混合物作为芳香化学品的用途:
其中:
R1为C1-C4烷基或-(C=O)-R3,
R2为氢、C1-C4烷基或-(C=O)-R4,且
R3和R4相互独立地选自氢和C1-C4烷基。
本发明用途还包括例如在基团R1和/或基团R2方面彼此不同的两种或更多种通式(I)化合物的混合物的用途。
本发明进一步涉及芳香化学品组合物,其包含至少一种如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物,和至少一种选自不同于化合物(I)的其它芳香化学品和非芳香化学品载体的其它化合物。
进一步发现通式(I)化合物通常显示出愉悦和特性气味,并且可用于制备加香即用组合物。另外,它们可有利地与不同于化合物(I)的其它芳香化学品组合以产生新的香味特征。
因此,本发明进一步涉及制备加香即用组合物的方法,其包括将至少一种式(I)化合物、其立体异构体或其立体异构体的混合物结合到即用组合物中,和如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物在改进加香即用组合物的香味特征中的用途。
在式(I)化合物组中,本领域中没有描述式(I.a)醚化合物和式(I.b)酯化合物。
因此,本发明还涉及新的通式(I.a)化合物、其立体异构体或其立体异构体的混合物及其制备方法:
其中:
R1a为C2-C4烷基且
R2a为氢或C2-C4烷基。
此外,本发明涉及新的通式(I.b)化合物、其立体异构体或其立体异构体的混合物及其制备方法:
其中:
R1b为-(C=O)-R3,
R2b为氢或-(C=O)-R4,且
R3和R4相互独立地选自氢和C1-C4烷基,条件是如果存在的话R3和R4是不同的。
式(I)化合物、其立体异构体或其立体异构体的混合物具有有利的感官性能,特别是愉悦的气味。因此,它们可有利地作为芳香化学品例如用于香料组合物、化妆品组合物、身体护理组合物、口腔和牙齿卫生用产品、卫生制品、清洁组合物、织物洗涤剂组合物、器皿洗涤组合物、香水分配器用组合物、食品、食品增补剂、药物组合物、作物保护组合物和其它即用组合物中。
借助它们的物理性能,式(I)化合物、其立体异构体或其立体异构体的混合物对加香即用组合物,例如特别是香料组合物中的其它芳香剂和其它常规成分具有特别好、基本通用的溶剂性能。因此,式(I)化合物、其立体异构体或其立体异构体的混合物有利地与其它芳香化学品组合,特别容许产生具有新的有利感觉特征的香料组合物。
此外,式(I)化合物、其立体异构体或其立体异构体的混合物可通过单步骤或两步合成,分别起始于容易得到且便宜的2,2,4,4-四甲基环丁烷-1,3-二醇以良好的收率和纯度制备。因此,式(I)化合物、其立体异构体或其立体异构体的混合物可以以大规模并且以简单且划算的方式制备。
另外,式(I)化合物、其立体异构体或其立体异构体的混合物可能具有低或者不具有毒性,因为它们衍生自2,2,4,4-四甲基环丁烷-1,3-二醇,关于它,目前不存在致癌或有毒效应的证明。
发明详述
在本发明上下文中,表述“C1-C4烷基”指甲基、乙基、正丙基、异丙基、正丁基、异丁烯和叔丁基。优选,表述“C1-C4烷基”指甲基、乙基、正丙基和异丙基,特别是甲基和乙基。
术语“芳香化学品”表示用于得到感觉印象,更确切地说,嗅觉或香味印象,特别是芳香或香味印象的物质。因此,这些芳香化学品适用于“芳香化学品组合物”和/或“加香即用组合物”中。因此,如本文所用,术语“芳香化学品组合物”指主要引起气味印象的组合物。同样,如本文所用,术语“加香即用组合物”指主要引发气味印象的即用组合物。
术语“嗅觉”表示不带任何正面或负面判断的气味印象,而术语“芳香”(也称为“芳香”或“香味”)与通常感觉愉悦的气味印象有关。气味引起味道印象。
术语“气味强烈物质”指显示出强烈的气味印象的物质或芳香化学品。强烈的气味印象应当理解意指芳香化学品甚至以非常低的气体空间浓度容许惊人感知的那些性能。强度可借助阈值测定测定。阈值为尽管不再必须限定,气味印象恰好仍可通过代表性试验小组感知时相关气体空间中的物质浓度。可能属于最强烈气味的已知物质类,即具有非常低的气味阈值的物质类为硫醇,其阈值通常在ppb/m3范围内。
“有利的感觉性能”、“有利的感官性能”或“愉悦的气味”为快乐印象,其描述由芳香化学品传达的气味印象的美好和简明。“美好”和“简明”为本领域技术人员,调香师熟悉的术语。美好一般指自发产生的正面感知的愉悦感觉印象。然而,“美好的”未必与“甜的”同义。“美好的”也可以为麝香或檀香气味。“简明”一般指对相同实验小组而言产生一些特异性的再现相同暗示的自发产生的感觉印象。例如,物质可具有“苹果”的自发回忆:气味则简明地为“苹果”的。如果由于气味为例如甜熟苹果回忆,该苹果气味是非常愉悦的,则气味称为“美好的”。然而,通常酸苹果的气味也可以是简明的。如果在闻物质时出现两种反应,在实施例中,因此出现美好和简明的苹果气味,则该物质具有特别有利的感觉性能。
取决于氧原子相对于环丁烷环的空间排列,式(I)化合物可作为单独的顺式异构体(I-cis)或反式异构体(I-trans)或者作为顺式/反式异构体混合物存在:
因此,本发明涉及顺式异构体,即(I-cis)的用途,反式异构体,即(I-trans)的用途,以及其顺式/反式异构体混合物,即(I-cis/trans)的用途。因此,如果没有另外说明,如本文所用表述“化合物I”、“通式I化合物”等指纯顺式异构体、纯反式异构体及其顺式/反式异构体混合物,其中异构体以相同的量存在或者包含过量的一种异构体。
化合物(I)的纯顺式异构体和纯反式异构体以及顺式/反式异构体混合物具有所有有利的感官性能。因此,化合物(I)的纯顺式异构体和纯反式异构体以及顺式/反式异构体混合物相同地适用作芳香化学品。此外,至少对于一些化合物(I),例如对于酯化合物乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯,顺式异构体的感官性能不明显地不同于反式异构体的感官性能。
另一方面,通式(I)醚化合物的基本香味特征不同于通式(I)的酯化合物的香味特征。
因此,本发明的第一实施方案涉及通式(I)醚化合物的用途,其中在式(I)中:
R1为C1-C4烷基,且
R2为氢或C1-C4烷基。
该第一实施方案的化合物(I)包括2,2,4,4-四甲基环丁烷-1,3-二醇的单醚以及二醚。通常,2,2,4,4-四甲基环丁烷-1,3-二醇的单醚显示出比2,2,4,4-四甲基环丁烷-1,3-二醇的相应二醚更小强度的气味。
因此,优选使用二醚化合物,即其中在式(I)中,R1和R2相互独立地选自C1-C4烷基的通式(I)化合物。
此外,其中与氧原子连接的取代基是相同的通式(I)醚化合物的合成通常比氧原子上具有不同的取代基的通式(I)醚化合物的合成更简单。
因此,进一步优选使用其中R1和R2为相同的通式(I)醚化合物。
优选的通式(I)醚化合物的实例为:
2,4-二甲氧基-1,1,3,3-四甲基-环丁烷,
2,4-二甲氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二甲氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二异丙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二异丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二异丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷,
2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二异丁氧基-1,1,3,3-四甲基-环丁烷,
2,4-二异丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,和
2,4-二异丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二-叔丁氧基-1,1,3,3-四甲基-环丁烷,
2,4-二-叔丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,和
2,4-二-叔丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在。
尽管与2,2,4,4-四甲基环丁烷-1,3-二醇的相应二醚相比,2,2,4,4-四甲基环丁烷-1,3-二醇的单醚的通常稍微较小强度的气味,这些单醚仍具有特性香味特征。因此,本发明2,2,4,4-四甲基环丁烷-1,3-二醇的单醚衍生物为用作芳香化学品的有价值化合物。
因此,本发明的另一优选实施方案涉及通式(I)化合物、其立体异构体或其立体异构体的混合物作为芳香化学品的用途:
其中:
R1为C1-C4烷基且
R2为氢。
该实施方案的优选单醚化合物(I)的实例为:
3-甲氧基-2,2,4,4-四甲基-环丁醇,
3-甲氧基-2,2,4,4-四甲基-环丁醇,其基本以其顺式异构体的形式存在,
3-甲氧基-2,2,4,4-四甲基-环丁醇,其基本以其反式异构体的形式存在,
3-乙氧基-2,2,4,4-四甲基-环丁醇,
3-乙氧基-2,2,4,4-四甲基-环丁醇,其基本以其顺式异构体的形式存在,
3-乙氧基-2,2,4,4-四甲基-环丁醇,其基本以其反式异构体的形式存在,
3-正丙氧基-2,2,4,4-四甲基-环丁醇,
3-正丙氧基-2,2,4,4-四甲基-环丁醇,其基本以其顺式异构体的形式存在,
3-正丙氧基-2,2,4,4-四甲基-环丁醇,其基本以其反式异构体的形式存在,
3-正丁氧基-2,2,4,4-四甲基-环丁醇,
3-正丁氧基-2,2,4,4-四甲基-环丁醇,其基本以其顺式异构体的形式存在,
3-正丁氧基-2,2,4,4-四甲基-环丁醇,其基本以其反式异构体的形式存在,
3-叔丁氧基-2,2,4,4-四甲基-环丁醇,
3-叔丁氧基-2,2,4,4-四甲基-环丁醇,其基本以其顺式异构体的形式存在,和
3-叔丁氧基-2,2,4,4-四甲基-环丁醇,其基本以其反式异构体的形式存在。
更优选使用通式(I)醚化合物,其中R1和R2为C1-C3烷基。
甚至更优选使用通式(I)醚化合物,其中R1和R2为相同的且选自甲基、乙基、正丙基和异丙基。
特别优选使用通式(I)醚化合物,其中R1和R2为甲基或乙基。
尤其优选使用:
2,4-二甲氧基-1,1,3,3-四甲基-环丁烷,
2,4-二甲氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二甲氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,和
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在。
本发明第二实施方案涉及通式(I)酯化合物的用途,其中在式(I)中:
R1为-(C=O)-R3,
R2为氢或-(C=O)-R4,且
R3和R4如上文所定义。
该第二实施方案的化合物(I)包括2,2,4,4-四甲基环丁烷-1,3-二醇的单酯以及二酯。通常,2,2,4,4-四甲基环丁烷-1,3-二醇的单酯显示出比2,2,4,4-四甲基环丁烷-1,3-二醇的相应二酯更小强度的气味。
因此,优选使用二酯化合物,即通式(I)化合物,其中在式(I)中:
R1为-(C=O)-R3,
R2为-(C=O)-R4且
R3和R4如上文所定义,
此处,其中与氧原子连接的取代基是相同的通式(I)酯化合物的合成也通常比氧原子上具有不同的取代基的通式(I)酯化合物的合成更简单。
因此,进一步优选使用通式(I)酯化合物,其中:
R1为-(C=O)-R3,
R2为-(C=O)-R4,且
R3和R4如上文所定义,
且其中基团R3和R4为相同的。
进一步优选使用通式(I)酯化合物,其中R3和R4选自氢和C1-C3烷基。
优选的通式(I)酯化合物的实例为:
甲酸(3-甲酰氧基-2,2,4,4-四甲基-环丁基)酯,
甲酸(3-甲酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其顺式异构体的形式存在,
甲酸(3-甲酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其反式异构体的形式存在,
乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯,
乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其顺式异构体的形式存在,
乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其反式异构体的形式存在,
丙酸(3-丙酰氧基-2,2,4,4-四甲基-环丁基)酯,
丙酸(3-丙酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其顺式异构体的形式存在,
丙酸(3-丙酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其反式异构体的形式存在,
异丁酸(3-异丁酰氧基-2,2,4,4-四甲基-环丁基)酯,
异丁酸(3-异丁酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其顺式异构体的形式存在,和
异丁酸(3-异丁酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其反式异构体的形式存在。
甚至更优选使用通式(I)酯化合物,其中R3和R4为相同的且选自氢和C1-C3烷基。
特别优选使用通式(I)酯化合物,其中R3和R4选自氢、甲基或乙基。
尤其优选使用:
乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯,
乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其顺式异构体的形式存在,和乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其反式异构体的形式存在。
在本发明一个特定实施方案中,通式(I)化合物基本以其顺式异构体的形式存在。
在本发明另一特定实施方案中,通式(I)化合物基本以其反式异构体的形式存在。
本发明另一优选实施方案涉及通式(I)化合物、其立体异构体或其立体异构体的混合物作为芳香化学品的用途:
其中:
R1为C1-C4烷基且
R2为-(C=O)-R3。
关于基团C1-C4烷基和-(C=O)-R3的优选和非常优选的含义,优选上文给出的论述。
该实施方案的特别优选的化合物为:
乙酸(3-甲氧基-2,2,4,4-四甲基-环丁基)酯,
乙酸(3-甲氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其顺式异构体的形式存在,和
乙酸(3-甲氧基-2,2,4,4-四甲基-环丁基)酯,其基本以其反式异构体的形式存在。
就这点而言,术语“基本”意指特定化合物的顺式或反式异构体以基于顺式和反式异构体的总量至少90重量%的量,优选以至少95重量%的量,特别是以至少98重量%的量存在。
通常,化合物(I)作为顺式/反式异构体混合物产生。顺式和反式异构体的分离可能是困难且费力的,或者不能以合理的努力完全实现。
因此,本发明的优选实施方案涉及如上文和下文所定义的通式(I)化合物的用途,其中通式(I)化合物以顺式/反式异构体混合物的形式存在。在这些混合物中,两种异构体可以以相同的量或者几乎相同的量,例如以50:50或55:45的顺式/反式或反式/顺式异构体比存在,或者一种异构体,即顺式或反式异构体可以以过量存在,例如一种异构体可以以60:40、65:35、70:30或75:25的顺式/反式或反式/顺式异构体比存在。
此外,化合物(I)可以以宽范围的纯度用作芳香化学品,只要杂质对化合物(I)的香味不具有显著的有害影响。因此,根据本发明,对于用作芳香化学品,化合物(I)的纯度不受特殊限制。优选,化合物(I)具有至少70%,特别是至少90%,尤其是至少95%的纯度。
由于其起始于2,2,4,4-四甲基环丁烷-1,3-二醇的制备方法,通式(I)二醚化合物可包含次要量的单醚化合物(I-OH),且通式(I)二酯化合物可包含次要量的单酯化合物(II-OH):
其中R1和R3具有上文给出的含义之一。
优选,可包含在通式(I)的二醚和二酯化合物中的单取代化合物(I-OH)或(II-OH)的量基于化合物(I)的总量为小于25重量%,更优选小于10重量%,甚至更优选小于5重量%,特别是小于1重量%。
在本发明的特别优选实施方案中,通式(I)的二醚和二酯化合物分别不含单取代化合物(I-OH)或(II-OH)。
同样,通式(I)的单醚和单酯化合物可包含次要量的相应二取代化合物。优选,包含在通式(I)的单醚和单酯化合物中的通式(I)二取代化合物的量基于化合物(I)的总量为小于25重量%,更优选小于10重量%,甚至更优选小于5重量%,特别是小于1重量%。
此外,其中基团R1和R2为不同的通式(I)二醚化合物以及其中基团R3和R4为不同的通式(I)二酯化合物(下文中称为不对称取代化合物)可包含次要量的对称取代化合物,即其中基团R1和R2为相同的通式(I)二醚化合物和其中基团R3和R4为相同的通式(I)二酯化合物。通常,可包含在通式(I)的不对称取代化合物中的对称取代化合物的量基于化合物(I)的总量为小于50重量%,优选小于25重量%,更优选小于10重量%,甚至更优选小于5重量%,特别是小于1重量%。
此外,其中基团R1为C1-C4烷基且R2为-(C=O)-R3的通式(I)醚-酯化合物在下文中也称为混合取代化合物(I),可包含相应的二醚或二酯化合物。此外,取决于单醚还是单酯化合物用作原料,这些混合取代化合物(I)还可包含次要量的相应单醚或单酯化合物。优选,可包含在通式(I)的混合取代化合物中的这些副产物的量基于化合物(I)的总量为小于50重量%,更优选小于40重量%,特别是小于30重量%。
上述优选实施方案可根据需要相互组合。
因此,在本发明特别优选的实施方案中,涉及具有至少95%的纯度并以顺式/反式异构体混合物的形式存在的通式(I)化合物的用途。
通式(I)单醚化合物可有效地通过通常在碱的存在下使用烷基化试剂R1-X将2,2,4,4-四甲基环丁烷-1,3-二醇烷基化而制备,其中R1具有上文给出的含义之一且X表示离去基团,其选自卤素,例如Cl、Br、I,和磺酸根,例如甲苯磺酸根、甲磺酸根、三氟甲磺酸根或全氟丁基磺酸根。
合适的碱通常选自无机碱和有机碱。
可用于该烷基化反应中的合适无机碱为例如碱金属碳酸盐,例如Li2CO3、Na2CO3、K2CO3或Cs2CO3,碱金属氢氧化物,例如LiOH、NaOH或KOH,和氢给体,例如NaH、LiAlH4或NaBH4。
可用于该烷基化反应中的合适有机碱为例如叔胺,例如三甲胺、三乙胺、三丙胺、乙基二异丙胺等,或者碱性N杂环,例如吗啉、吡啶、卢剔啶、DMAP、DABCO、DBU或DBN。
烷基化反应在技术人员熟知的常规烷基化反应条件下进行。
通常,使2,2,4,4-四甲基环丁烷-1,3-二醇与亚等摩尔或几乎等摩尔量,例如0.7、0.8、0.9或0.95当量的烷基化试剂R1-X反应以得到单取代化合物(I-OH),使其进一步经受提纯步骤以除去不想要的副产物或杂质,例如残余原料或相应的二取代化合物。
一般而言,提纯步骤通过使用常规提纯方法,例如结晶、蒸馏或色谱法,例如柱色谱或高效液相色谱进行。
其中基团R1和R2为相同的通式(I)二醚化合物的制备通常通过使2,2,4,4-四甲基环丁烷-1,3-二醇分别与至少2当量,例如2.0、2.1、2.5或3.0当量的烷基化试剂R1-X或R2-X反应而进行,其中基团R1、R2和X具有以上给出的含义之一,随后使所得粗产物经受如上文所定义的提纯步骤。如果仅次要量的杂质和副产物存在于粗产物混合物中,则提纯步骤也可借助简单的萃取后处理进行。
其中基团R1和R2不同的通式(I)二醚化合物的制备通常通过首先使2,2,4,4-四甲基环丁烷-1,3-二醇与亚等摩尔或几乎等摩尔量,例如0.7、0.8、0.9或0.95当量的烷基化试剂R1-X反应以得到单取代化合物(I-OH),在提纯步骤以后使其进一步与第二烷基化试剂R2-X反应而进行。
一般而言,通式(I)酯化合物有效地通过使2,2,4,4-四甲基环丁烷-1,3-二醇与羧酸R3-COOH以及任选与羧酸R4-COOH(其中R3和R4具有以上给出的含义之一)或其酸酐,或者羧酸R3-COOH和/或R4-COOH与其酸酐的混合物反应而制备。反应通常在酯化催化剂或碱的存在下进行。
可用于该反应中的合适酯化催化剂为技术人员熟知的。合适的酯化催化剂为例如金属基催化剂,例如金属、金属氧化物或金属盐如金属醇盐形式的铁、镉、钴、铅、锌、锑、镁、钛和锡催化剂;矿物酸,例如硫酸、盐酸或磷酸;或有机磺酸,例如甲磺酸或对甲苯磺酸。
合适的碱为例如如上文所定义的有机碱。
作为选择,通式(I)酯化合物可通过在有机碱的存在下使2,2,4,4-四甲基环丁烷-1,3-二醇与式R3-(C=O)X'或R4-(C=O)X'的酸性卤化物反应而制备,其中R3和R4具有以上给出的含义之一,且X'为卤素如Cl、Br或I。
合适的有机碱如上文所定义。
制备通式(I)酯化合物的各个反应条件是技术人员熟知的。
为制备通式(I)单酯化合物,通常使2,2,4,4-四甲基环丁烷-1,3-二醇与亚等摩尔或几乎等摩尔量,例如0.7、0.8、0.9或0.95当量的羧酸R3-COOH或其酐或者所述羧酸与其酐的混合物反应。作为选择,通常使2,2,4,4-四甲基环丁烷-1,3-二醇与相同量的酸性卤化物R3-(C=O)X'在有机碱的存在下反应。随后使所得粗产物经受如上文所定义的提纯步骤。
为制备基团R3和R4为相同的通式(I)二酯化合物,通常使2,2,4,4-四甲基环丁烷-1,3-二醇分别与至少2当量,例如2.0、2.1、2.5或3.0当量的羧酸R3-COOH或R4-COOH、其酐或者所述羧酸与其酐的混合物反应。作为选择,通常使2,2,4,4-四甲基环丁烷-1,3-二醇分别与至少2当量的酸性卤化物R3-(C=O)X'或R4-(C=O)X'在有机碱的存在下反应。随后使所得粗产物经受如上文所定义的提纯步骤。如果仅次要量的杂质和副产物存在于粗产物混合物中,则提纯步骤也可借助简单的萃取后处理进行。
其中基团R3和R4不同的通式(I)二酯化合物的制备通常通过首先使2,2,4,4-四甲基环丁烷-1,3-二醇与亚等摩尔或几乎等摩尔量,例如0.7、0.8、0.9或0.95当量的羧酸R3-COOH或其酐反应以得到单取代化合物(II-OH),在提纯步骤以后,使其进一步与第二羧酸R4-COOH或其酐反应而进行。
作为选择,其中基团R3和R4不同的化合物(I)的制备也可通过首先使2,2,4,4-四甲基环丁烷-1,3-二醇与亚等摩尔或几乎等摩尔量,例如0.7、0.8、0.9或0.95当量的酸性卤化物R3-(C=O)X'在有机碱的存在下反应以得到单取代化合物(II-OH),在提纯步骤以后使其进一步与第二酸性卤化物R4-(C=O)X'反应而实现。
原料2,2,4,4-四甲基环丁烷-1,3-二醇为常用作合成聚合物材料的单体的二醇结构单元。因此,2,2,4,4-四甲基环丁烷-1,3-二醇容易由商业来源得到。作为选择,2,2,4,4-四甲基环丁烷-1,3-二醇也可通过使用本领域中熟练描述的方法,例如借助二甲基烯酮的二聚而大量合成。
组合物:
式(I)化合物、其立体异构体或其立体异构体的混合物可用于多种组合物如即用组合物中。式(I)化合物的嗅觉性能、物质性能(例如在常规溶剂中的溶解度和与这类组合物的其它常规组分的相容性)以及毒物学可接受性强调它们特别适于所述使用目的和组合物。
此外,通式(I)化合物显示出有利的第二性能。
例如,通式(I)化合物可以由于与其它芳香剂的协同效应而提供更好的感觉特征,这意指它们可提供对其它芳香剂的促进效应。因此,它们适用作其它芳香剂的促进剂。
促进效应意指在芳香配制剂中,物质增强和强化混合物的总体印象。在薄荷范围内,例如已知薄荷基甲醚强化薄荷油的芳香或味道混合物,特别是在头香中,产生相当更强烈且更复杂的感知,尽管为纯物质的醚本身根本不显现强烈的气味。在芳香剂应用中,作为纯物质,(二氢茉莉酮酸甲酯)仅显示出轻微茉莉花香,作为气味促进剂增强香料组合物的扩散、新鲜感和体积。当其中气味印象待特别快且强烈地传达的要求头香特性应用时,例如在除臭剂、空气清新剂中或者在口香糖中的味觉区中,促进效应是特别需要的。
为实现该促进效应,通式(I)化合物、其立体异构体或其立体异构体的混合物通常以基于芳香剂混合物的总重量0.1-20重量%的量,优选以0.5-5重量%的量,特别是以0.6-3重量%的量使用。
此外,通式(I)化合物、其立体异构体或其立体异构体的混合物可对它们应用于其中的组合物本身具有其它积极影响。例如,通式(I)化合物、其立体异构体或其立体异构体的混合物可增强组合物的总体性能,例如组合物的稳定性、配制稳定性、可延伸性或持久力。
因此,本发明另一实施方案涉及通式(I)化合物或者两种或更多种不同式(I)化合物的混合物或者其立体异构体或其立体异构体的混合物作为芳香化学品在即用组合物中的用途。
如本文所用,术语“即用组合物”指意欲由最终使用者直接应用或使用的组合物。
一般而言,本发明芳香化学品,即如上文所定义的通式(I)化合物可用于其中的即用组合物为加香即用组合物。
本发明芳香化学品,即如上文所定义的通式(I)化合物可用于其中的加香即用组合物为例如用于个人护理的组合物、用于家庭护理的组合物、用于工业应用的组合物以及用于其它应用的组合物,例如药物组合物或作物保护组合物。
优选,即用组合物选自香料组合物、化妆品组合物、身体护理组合物、口腔和牙齿卫生用产品、卫生制品、清洁组合物、织物洗涤剂组合物、器皿洗涤组合物、香水分配器用组合物、食品、食品增补剂、药物组合物和作物保护组合物。
香料组合物可选自精细芳香剂、液体形式、凝胶状形式或应用于固体载体上的形式的空气清新剂、气溶胶喷雾、加香清洁剂、香烛和芳香油,例如灯油或按摩油。
精细芳香剂的实例为香料提取物、淡香精(Eau de Parfums)、淡香水(Eau deToilettes)、古龙水(Eau de Colognes)、固体香水(Eau de Solide)和香精(ExtraitParfum)等。
身体护理组合物可选自须后水、须前产品、古龙水(splash cologne)、固体和液体皂、淋浴凝胶、洗发水、剃须皂、剃须泡沫、沐浴油、水包油型、油包水型和水包油包水型化妆品乳液,例如护肤霜和露、面霜和露、防晒霜和露、晒后霜和露、护手霜和露、护足霜和露、脱毛霜和露、须后霜和露以及美黑霜和露,粉、水凝胶、头发护理产品,例如发用喷雾、发用凝胶、发用定型露、护发素、洗发水以及永久和半永久染发剂,发用定型组合物,例如冷烫,和发用柔顺组合物、养发素、洗发乳和洗发露,除臭剂和止汗剂,例如腋下喷雾、滚珠、除臭棒和除臭膏,装饰性化妆品,例如眼线笔、眼影、指甲油、粉底、唇膏和染眉毛油。
口腔和牙齿卫生用产品可选自牙膏、洁牙线、漱口水、口气清新剂、牙用泡沫、牙用凝胶和牙用条。
卫生制品可选自香、杀虫剂、驱避剂、推进剂、除锈剂、加香清新擦巾、腋窝垫、婴儿尿布、卫生巾、卫生纸、化妆巾、手帕纸、器皿洗涤剂和除臭剂。
清洁组合物,例如固体表面清洁剂,可选自加香酸性、碱性和中性清洁剂,例如地板清洁剂、窗户清洁剂、浴室和卫生清洁剂、冲刷乳、固体和液体卫生间清洁剂、粉末和泡沫地毯清洁剂、用于手动和机器器皿洗涤的器皿洗涤剂、蜡和抛光剂如家具抛光剂、地板蜡、鞋油、消毒剂、表面消毒剂和卫生清洁剂、刹车清洁剂、管清洁剂、水垢清洁剂、烤架和烤箱清洁剂、藻类和苔藓清除剂、脱模剂和立面清洁剂。
织物洗涤剂组合物可选自液体洗涤剂、粉末洗涤剂、衣物预处理剂如漂白剂、浸泡剂和去污剂、织物软化剂、洗涤皂、洗涤片。
食品意指未加工、烹熟或加工的可食用物质、冰、饮料或者用于或意欲全部或部分地用于人类消耗的成分,或者口香糖、胶、果子冻和糖果。
食品增补剂为意欲摄取的产品,其包含意欲向食物增加其它营养价值的饮食成分。饮食成分可以为以下物质中的一种或任何组合:维生素、矿物、药草或其它植物性药材、氨基酸、人们用于通过提高饮食摄入量而补充饮食的饮食物质、浓缩物、代谢物、组分或提取物。食品增补剂可以以许多形式发现,例如片剂、胶囊、软凝胶、凝胶胶囊、液或粉。
药物组合物包含意欲用于诊断、护理、缓解、治疗或预防疾病的组合物以及意欲影响人或其它动物的身体结构或任何功能的制品(不同于食品)。
作物保护组合物包含意欲管理危害农作物和森林的植物病害、杂草和其它害虫(脊椎动物和无脊椎动物)的组合物。
本发明组合物可进一步包含一种或多种物质,例如防腐剂、研磨剂、抗痤疮剂、对抗皮肤老化的试剂、抗菌剂、减肥剂、去头屑剂、消炎剂、防刺激剂、缓和刺激的试剂、抗微生物剂、抗氧化剂、收敛剂、抑汗剂、抗菌剂、抗静电剂、粘合剂、缓冲剂、载体材料、螯合剂、细胞刺激剂、清洁剂、护理剂、脱毛剂、表面活性物质、除臭剂、止汗药、乳化剂、酶、精油、纤维、成膜剂、定色剂、泡沫形成剂、泡沫稳定剂、用于防止起泡的物质、泡沫促进剂、杀真菌剂、胶凝剂、凝胶形成剂、发用护理剂、发用定型剂、发用柔顺剂、保湿剂、保湿物质、润湿物质、漂白剂、增强剂、去污剂、荧光增白剂、浸渍剂、防污剂、减摩剂、润滑剂、保湿霜、药膏、遮光剂、增塑剂、覆盖剂、抛光剂、闪光剂、聚合物、粉末、蛋白质、加脂剂、去角质剂、硅氧烷、皮肤镇定剂、皮肤清洁剂、皮肤护理剂、皮肤愈合剂、皮肤亮化剂、皮肤保护剂、皮肤软化剂、冷却剂、皮肤冷却剂、升温剂、皮肤升温剂、稳定剂、UV吸收剂、UV过滤剂、织物软化剂、悬浮剂、皮肤美黑剂、增稠剂、维生素、油、蜡、脂肪、磷脂、饱和脂肪酸、单或多不饱和脂肪酸、α-羟基酸、多羟基脂肪酸、液化剂、染料、颜色保护剂、颜料、防腐剂、多元醇、表面活性剂、电解质、有机溶剂或硅氧烷衍生物。
如上文所述,进一步发现通式(I)化合物通常显示出愉悦和特性气味,并且可用于制备加香即用组合物,和/或它们可有利地与不同于化合物(I)的其它芳香化学品组合以产生新的香味特征。
因此,本发明的具体实施方案涉及式(I)化合物或者两种或更多种不同式(I)化合物的混合物或其立体异构体或其立体异构体的混合物在改进加香即用组合物的香味特征的用途。
本发明进一步涉及芳香化学品组合物,其包含至少一种如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物,和至少一种选自不同于化合物(I)的其它芳香化学品和非芳香化学品载体的其它化合物。
这包括包含至少一种如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物和至少一种不同于化合物(I)的其它芳香化学品的芳香化学品组合物。
进一步包括包含至少一种如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物和至少一种非芳香化学品载体的芳香化学品组合物。
还包括包含至少一种如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物、至少一种不同于化合物(I)的其它芳香化学品和至少一种非芳香化学品载体的芳香化学品组合物。
优选,芳香化学品组合物包含至少一种如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物、至少一种不同于化合物(I)的其它芳香化学品和至少一种非芳香化学品载体。
不同于化合物(I)的其它芳香化学品可例如为一种,优选2、3、4、5、6、7、8种其它芳香化学品,其选自:乙酸香叶酯(乙酸酯3,7-二甲基-2,6辛二烯-1基)酯、α-己基肉桂醛、异丁酸2-苯氧基乙酯(Phenirat1)、二氢月桂烯醇(2,6-二甲基-7-辛烯-2-醇)、二氢茉莉酸酯(优选具有大于60重量%的顺式异构体含量)(Hedione9、Hedione HC9)、4,6,6,7,8,8-六甲基-1,3,4,6,7,8-六氢-环戊[g]苯并吡喃(Galaxolid3)、四氢里哪醇(3,7-二甲基辛-3-醇)、乙基里哪醇、水杨酸苄基酯、2-甲基-3-(4-叔丁基苯基)丙醛(Lilial2)、肉桂醇、乙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5-茚基酯和/或乙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-6-茚基酯(Herbaflorat1)、香茅醇、乙酸香茅酯、四氢香叶醇、香草醛、乙酸里哪酯、乙酸苯乙酯(乙酸1-苯基乙酯)、八氢-2,3,8,8-四甲基-2-萘乙酮和/或2-乙酰基-1,2,3,4,6,7,8-八氢-2,3,8,8-四甲基萘(Iso E Super3)、水杨酸乙酯、乙酸4-叔丁基环己基酯(Oryclone1)、乙酸2-叔丁基环己基酯(Agrumex HC1)、α-紫罗兰酮(4-(2,2,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮)、正-α-甲基紫罗兰酮、α-异甲基紫罗兰酮、香豆素、乙酸萜品酯、2-苯基乙醇、4-(4-羟基-4-甲基戊基)-3-环己烯甲醛(Lyral3)、α-戊基肉桂醛、巴西酸亚乙酯、(E)-和/或(Z)-3-甲基环十五碳-5-烯酮(Muscenon9)、15-十五碳-11-烯内酯和/或15-十五碳-12-烯内酯(Globalide1)、15-环十五碳烯内酯(Macrolide1)、1-(5,6,7,8-四氢-3,5,5,6,8,8-六甲基-2-萘基)乙酮(Tonalid10)、2-异丁基-4-甲基四氢-2H-吡喃-4-醇(Florol9)、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Sandolen1)、顺-乙酸3-己烯酯、反-乙酸3-己烯酯、反-2/顺-6-壬二烯醇、2,4-二甲基-3-环己烯甲醛(Vertocitral1)、2,4,4,7-四甲基辛-6-烯-3-酮(Claritone1)、2,6-二甲基-5-庚烯-1-醛(Melonal2)、龙脑、3-(3-异丙基苯基)丁醛(Florhydral2)、2-甲基-3-(3,4-亚甲基二氧基苯基)丙醛(Helional3)、3-(4-乙基苯基)-2,2-二甲基丙醛(Florazon1)、7-甲基-2H-1,5-苯并二氧杂-3(4H)-酮(Calone)、乙酸3,3,5-三甲基环己基酯(优选具有70重量%或更多的顺式异构体含量)和2,5,5-三甲基-1,2,3,4,4a,5,6,7-八氢萘-2-醇(Ambrinol S1)。
如果上文给出商品名,则这些指以下来源:
1 Symrise GmbH,德国的商品名;
2 Givaudan AG,瑞士的商品名;
3 International Flavors & Fragrances Inc.,美国的商品名;
5 Danisco Seillans S.A.,法国的商品名;
9 Firmenich S.A.,瑞士的商品名;
10 PFW Aroma Chemicals B.V.荷兰的商品名。
如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物可与其组合例如以得到本发明组合物的其它芳香化学品可在例如S.Arctander自己出版的Perfumeand Flavor Chemicals,第I和II卷,Montclair,N.J.,1969,或者K.Bauer,D.Garbe和H.Surburg,Common Fragrance and Flavor Materials,第4版,Wiley-VCH,Weinheim 2001中找到。具体而言,可提到:
天然来源的提取物,例如精油、凝结物、净油、树脂、类树脂、香液、酊剂,例如
龙涎香酊;脂檀油;当归籽油;当归根油;茴香油;缬草油;丁香罗勒油;树苔净油;月桂油;艾蒿油;安息香树脂;佛手柑油;蜜蜡净油;白桦油;苦杏仁油;香旱芹油;木刺叶油;香脂豆油;杜松油;菖蒲油;樟脑油;卡南加油;小豆蔻油;卡藜油;桂皮油;桂皮净油;海狸香净油;雪松叶油;雪松木油;岩玫瑰油;香茅油;柠檬油;苦配巴香脂;古巴香脂油;芫荽油;广木香根油;枯茗油;柏木油;印蒿油;莳萝果油;莳萝籽油;橡苔净油(Eau de broutsabsolute);橡苔净油(oak moss absolute);榄香油;龙蒿油;柠檬桉油;桉树油;茴香油;松针油;格蓬油;格蓬香树脂;天竺葵油;葡萄柚油;愈创木油;古云香脂;古芸香脂油;蜡菊净油;蜡菊油;生姜油;鸢尾根净油;鸢尾根油;茉莉净油;菖蒲油;洋甘菊熟油;罗马甘菊油;胡萝卜籽油;卡藜油;松针油;留兰香油;香菜油;岩蔷薇油;岩蔷薇净油;岩蔷薇树脂;杂熏衣草净油;杂熏衣草油;熏衣草净油;熏衣草油;柠檬香草油;独活草油;蒸馏白柠檬油;压榨白柠檬油;里哪油;山苍子油;月桂叶油;肉豆蔻衣油;马郁兰油;橘子油;香厚壳桂皮油;含羞草净油;麝香籽油;麝香酊;鼠尾草油;肉豆蔻油;没药净油;没药油;桃金娘油;丁香叶油;丁香花油;橙花油;乳香净油;乳香油;防风根油;橙花净油;橙油;牛至油;玫瑰草油;广藿香油;紫苏子油;秘鲁香脂油;欧芹叶油;欧芹籽油;苦橙叶油;薄荷油;胡椒油;甘椒油;松油;胡薄荷油;玫瑰净油;玫瑰木油;玫瑰油;迷迭香油;Dalmatian鼠尾草油;西班牙鼠尾草油;檀木油;芹菜籽油;穗熏衣草油;八角茴香油;苏合香油;万寿菊油;冷杉针油;茶树油;松节油;百里香油;吐鲁香脂;零陵香豆净油;晚香玉净油;香草香精提取物;紫罗兰叶净油;马鞭草油;香根油;杜松子油;酒糟油;苦艾油;冬绿油;牛膝草油;灵猫净油;桂叶油;桂皮油及其馏分或由其分离的成分;
来自烃组的各种芳香剂,例如3-蒈烯;α-蒎烯;β-蒎烯;α-萜品烯;γ-萜品烯;对伞花烃;红没药烯;莰烯;石竹烯;雪松烯;金合欢烯;柠檬烯;长叶烯;月桂烯;罗勒烯;巴伦西亚桔烯;(E,Z)-1,3,5-十一碳三烯;苯乙烯;二苯基甲烷;
脂族醇,例如己醇;辛醇;3-辛醇;2,6-二甲基庚醇;2-甲基-2-庚醇;2-甲基-2-辛醇;(E)-2-己烯醇;(E)-和(Z)-3-己烯醇;1-辛烯-3-醇;3,4,5,6,6-五甲基-3/4-庚烯-2-醇和3,5,6,6-四甲基-4-亚甲基庚-2-醇的混合物;(E,Z)-2,6-壬二烯醇;3,7-二甲基-7-甲氧基辛-2-醇;9-癸烯醇;10-十一碳烯醇;4-甲基-3-癸烯-5-醇;
脂族醛及其缩醛,例如己醛;庚醛;辛醛;壬醛;癸醛;十一醛;十二醛;十三醛;2-甲基辛醛;2-甲基壬醛;(E)-2-己烯醛;(Z)-4-庚烯醛;2,6-二甲基-5-庚烯醛;10-十一烯醛;(E)-4-癸烯醛;2-十二烯醛;2,6,10-三甲基-9-十一烯醛;2,6,10-三甲基-5,9-十一碳二烯醛;庚醛二乙基缩醛;1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅氧基乙醛;(E/Z)-1-(1-甲氧基丙氧基)-己-3-烯;脂族酮及其肟,例如2-庚酮;2-辛酮;3-辛酮;2-壬酮;5-甲基-3-庚酮;5-甲基-3-庚酮肟;2,4,4,7-四甲基-6-辛烯-3-酮;6-甲基-5-庚烯-2-酮;
脂族含硫化合物,例如3-甲基硫代己醇;乙酸3-甲基硫代己酯;3-巯基己醇;乙酸3-巯基己酯;丁酸3-巯基己酯;乙酸3-乙酰基流量的己酯;1-薄荷烯-8-硫醇;
脂族腈,例如2-壬烯腈;2-十一烯腈;2-十三烯腈;3,12-十三碳二烯腈;3,7-二甲基-2,6-辛二烯腈;3,7-二甲基-6-辛烯腈;
脂族羧酸的酯,例如(E)-和(Z)-甲酸3-己烯酯;乙酰乙酸乙酯;乙酸异戊酯;乙酸己酯;乙酸3,5,5-三甲基己酯;乙酸3-甲基-2-丁烯酯;(E)-乙酸2-己烯酯;(E)-和(Z)-乙酸3-己烯酯;乙酸辛酯;乙酸3-辛酯;乙酸1-辛烯-3-基质;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;(E)-和(Z)-异丁酸3-己烯酯;巴豆酸己酯;异戊酸乙酯;2-甲基戊酸乙酯;己酸乙酯;己酸烯丙酯;庚酸乙酯;庚酸烯丙酯;辛酸乙酯;(E,Z)-2,4-癸二烯酸乙酯;2-辛酸甲酯;2-壬酸甲酯;2-异戊氧基乙酸烯丙酯;3,7-二甲基-2,6-辛二烯酸甲酯;巴豆酸4-甲基-2-戊基酯;
无环萜烯醇,例如香叶醇;橙花醇;里哪醇;薰衣草醇;橙花叔醇;法呢醇;四氢里哪醇;2,6-二甲基-7-辛烯-2-醇;2,6-二甲基辛-2-醇;2-甲基-6-亚甲基-7-辛烯-2-醇;2,6-二甲基-5,7-辛二烯-2-醇;2,6-二甲基-3,5-辛二烯-2-醇;3,7-二甲基-4,6-辛二烯-3-醇;3,7-二甲基-1,5,7-辛二烯-3-醇;2,6-二甲基-2,5,7-辛二烯-1-醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸烯酯和3-甲基-2-丁烯酸酯;无环萜烯醛和酮,例如香叶醛;橙花醛;香茅醛;7-羟基-3,7-二甲基辛醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一烯醛;香叶基丙酮;以及香叶醛、橙花醛、7-羟基-3,7-二甲基辛醛的二甲基-和二乙基缩醛;环状萜烯醇,例如薄荷醇;异胡薄荷醇;α-萜烯醇;萜烯-4-醇;薄荷-8-醇;薄荷-1-醇;薄荷-7-醇;龙脑;异龙脑;氧化里哪醇;诺卜醇;雪松醇;龙涎醇;香根醇;愈创醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸烯酯和3-甲基-2-丁烯酸酯;
环状萜烯醛和酮,例如薄荷酮;异薄荷酮;8-巯基异薄荷-3-酮;香芹酮;樟脑;葑酮;α-紫罗兰酮;β-紫罗兰酮;α-正甲基紫罗兰酮;β-正甲基紫罗兰酮;α-异甲基紫罗兰酮;β-异甲基紫罗兰酮;α-鸢尾酮;α-突厥酮;β-突厥酮;β-突厥烯酮;δ-突厥酮;γ-突厥酮;1-(2,4,4-三甲基-2-环己烯-1-基)-2-丁烯-1-酮;1,3,4,6,7,8a-六氢-1,1,5,5-四甲基-2H-2,4a-桥亚甲基萘-8(5H)-酮;2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-2-丁烯醛;诺卡酮;二氢诺卡酮;4,6,8-巨豆三烯-3-酮;α-甜橙醛;β-甜橙醛;乙酰化雪松木油(甲基雪松酮);
环状醇,例如4-叔丁基环己醇;3,3,5-三甲基环己醇;3-异龙脑环己醇;2,6,9-三甲基-Z2,Z5,E9-环十二碳三烯-1-醇;2-异丁基-4-甲基四氢-2H-吡喃-4-醇;
脂环族醇,例如α-3,3-三甲基环己基甲醇;1-(4-异丙基环己基)乙醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)丁醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;2-乙基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)戊-2-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;3,3-二甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;1-(2,2,6-三甲基环己基)戊-3-醇;1-(2,2,6-三甲基环己基)己-3-醇;
环状和脂环族醚,例如桉油酚;甲基柏木醚;环十二烷基甲醚;1,1-二甲氧基环十二烷;(乙氧基甲氧基)环十二烷;α-环氧柏木烷;3a,6,6,9a-四甲基十二氢萘[2,1-b]呋喃;3a-乙基-6,6,9a-三甲基十二氢萘[2,1-b]呋喃;1,5,9-三甲基-13-氧杂二环-[10.1.0]十三碳-4,8-二烯;玫瑰醚;2-(2,4-二甲基-3-环己烯-1-基)-5-甲基-5-(1-甲基丙基)-1,3-二烷;
环状和大环酮,例如4-叔丁基环己酮;2,2,5-三甲基-5-戊基环戊酮;2-庚基环戊酮;2-戊基环戊酮;2-羟基-3-甲基-2-环戊烯-1-酮;3-甲基-顺-2-戊烯-1-基-2-环戊烯-1-酮;3-甲基-2-戊基-2-环戊烯-1-酮;3-甲基-4-环戊烯酮;3-甲基-5-环戊烯酮;3-甲基环十五酮;4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮;4-叔戊基环己酮;5-环十六碳烯-1-酮;6,7-二氢-1,1,2,3,3-五甲基-4(5H)-茚酮;8-环十六碳烯-1-酮;7-环十六碳烯-1-酮;(7/8)-环十六碳烯-1-酮;9-环十七碳-1-酮;环十五酮;环十六酮;
脂环族醛,例如2,4-二甲基-3-环己烯甲醛;2-甲基-4-(2,2,6-三甲基环己烯-1-基)-2-丁烯醛;4-(4-羟基-4-甲基戊基)-3-环己烯甲醛;4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛;
脂环族酮,例如1-(3,3-二甲基环己基)-4-戊烯-1-酮;2,2-二甲基-1-(2,4-二甲基-3-环己烯-1-基)-1-丙酮;1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮;2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢-2-萘基甲酮;甲基2,6,10-三甲基-2,5,9-环十二碳三烯酮;叔丁基(2,4-二甲基-3-环己烯-1-基)酮;
环状醇的酯,例如乙酸2-叔丁基环己基酯;乙酸4-叔丁基环己基酯;乙酸2-叔戊基环己基酯;乙酸4-叔戊基环己基酯;乙酸3,3,5-三甲基环己基酯;乙酸八氢-2-萘基酯;巴豆酸2-环戊基环戊基酯;乙酸3-戊基四氢-2H-吡喃-4-基酯;乙酸八氢-2,5,5,8a-四甲基-2-萘基酯;乙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;丙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;异丁酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;乙酸4,7-桥亚甲基八氢-5或6-茚基酯;
脂环族醇的酯,例如巴豆酸1-环己基乙酯;
脂环族羧酸的酯,例如3-环己基丙酸烯丙基酯;环己氧基乙酸烯丙基酯;顺-和反-二氢茉莉酸酮甲酯;顺-和反-茉莉酸酮甲酯;2-己基-3-氧代环戊烷羧酸甲酯;2-乙基-6,6-二甲基-2-环己烯羧酸乙酯;2,3,6,6-四甲基-2-环己烯羧酸乙酯;2-甲基-1,3-二氧杂环戊烷-2-乙酸乙酯;
芳脂族醇,例如苄醇;1-苯基乙醇、2-苯基乙醇、3-苯基丙醇;2-苯基丙醇;2-苯氧基乙醇;2,2-二甲基-3-苯基丙醇;2,2-二甲基-3-(3-甲基苯基)丙醇;1,1-二甲基-2-苯基乙醇;1,1-二甲基-3-苯基丙醇;1-乙基-1-甲基-3-苯基丙醇;2-甲基-5-苯基戊醇;3-甲基-5-苯基戊醇;3-苯基-2-丙烯-1-醇;4-甲氧基苄醇;1-(4-异丙基苯基)乙醇;
芳脂族醇和脂族羧酸的酯,例如乙酸苄酯;丙酸苄酯;异丁酸苄酯;异戊酸苄酯;乙酸2-苯基乙酯;丙酸2-苯基乙酯;异丁酸2-苯基乙酯;异戊酸2-苯基乙酯;乙酸1-苯基乙酯;乙酸α-三氯甲基苄酯;乙酸α,α-二甲基苯基乙酯;丁酸α,α-二甲基苯基乙酯;乙酸肉桂基酯;异丁酸2-苯氧基乙酯;乙酸酯4-甲氧基苄酯;
芳脂族醚,例如2-苯基乙基甲醚;2-苯基乙基异戊基醚;2-苯基乙基1-乙氧基***;苯乙醛二甲基乙缩醛;苯乙醛二乙基乙缩醛;龙葵醛二甲基乙缩醛;苯乙醛甘油乙缩醛;2,4,6-三甲基-4-苯基-1,3-二烷;4,4a,5,9b-四氢茚基[1,2-d]-间-二英;4,4a,5,9b-四氢-2,4-二甲基茚基[1,2-d]-间-二英。
芳族和芳脂族醛,例如苯甲醛;苯乙醛;3-苯基丙醛;龙葵醛;4-甲基苯甲醛;4-甲基苯基-乙醛;3-(4-乙基苯基)-2,2-二甲基丙醛;2-甲基-3-(4-异丙基苯基)-丙醛;2-甲基-3-(4-叔丁基苯基)丙醛;2-甲基-3-(4-异丁基苯基)-丙醛;3-(4-叔丁基苯基)丙醛;肉桂醛;α-丁基肉桂醛;α-戊基肉桂醛;α-己基肉桂醛;3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯甲醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧基苯甲醛;3,4-二甲氧基苯甲醛;2-甲基-3-(4-甲氧基苯基)丙醛;2-甲基-3-(4-亚甲基二氧基苯基)丙醛;
芳族和芳脂族酮,例如苯乙酮;4-甲基苯乙酮;4-甲氧基苯乙酮;4-叔丁基-2,6-二甲基苯乙酮;4-苯基-2-丁酮;4-(4-羟苯基)-2-丁酮;1-(2-萘基)-乙酮;2-苯并呋喃基-乙酮;(3-甲基-2-苯并呋喃基)乙酮;二苯甲酮;1,1,2,3,3,6-六甲基-5-茚满基甲酮;6-叔丁基-1,1-二甲基-4-茚满基甲酮;1-[2,3-二氢-1,1,2,6-四甲基-3-(1-甲基乙基)-1H-5-茚基]乙酮;5′,6′,7′,8′-四氢-3′,5′,5′,6′,8′,8′-六甲基-2-萘乙酮;
芳族和芳脂族羧酸及其酯;例如苯甲酸;苯基乙酸;苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄酯;苯基乙酸甲酯;苯基乙酸乙酯;苯基乙酸香叶基酯;苯基乙酸苯基乙酯;肉桂酸甲酯;肉桂酸乙酯;肉桂酸苄酯;肉桂酸苯基乙酯;肉桂酸肉桂酯;苯氧基乙酸烯丙酯;水杨酸甲酯;水杨酸异戊基酯;水杨酸己酯;水杨酸环己基酯;顺-水杨酸3-己烯酯;水杨酸苄酯;水杨酸苯基乙酯;2,4-二羟基-3,6-二甲基苯甲酸甲酯;3-苯基甘油三乙酯;3-甲基-3-苯基甘油酸乙酯;
含氮芳族化合物,例如2,4,6-三硝基-1,3-二甲基-5-叔丁基苯;3,5-二硝基-2,6-二甲基-4-叔丁基苯乙酮;肉桂腈;3-甲基-5-苯基-2-戊烯腈;3-甲基-5-苯基戊腈;邻氨基苯甲酸甲酯;N-甲基邻氨基苯甲酸甲酯;邻氨基苯甲酸甲酯与7-羟基-3,7-二甲基辛醛、2-甲基-3-(4-叔丁基苯基)丙醛或2,4-二甲基-3-环己烯甲醛的席夫碱;6-异丙基喹啉;6-异丁基喹啉;6-仲丁基喹啉;2-(3-苯基丙基)吡啶;吲哚;粪臭素;2-甲氧基-3-异丙基吡嗪;2-异丁基-3-甲氧基吡嗪;
苯酚、苯基醚和苯基酯,例如草蒿脑;茴香脑;丁子香酚;丁子香基甲醚;异丁子香酚;异丁子香基甲醚;麝香草酚;香芹酚;二苯醚;β-萘基甲醚;β-萘基***;β-萘基异丁醚;1,4-二甲氧基苯;乙酸丁子香基酯;2-甲氧基-4-甲基苯酚;2-乙氧基-5-(1-丙烯基)苯酚;苯基乙酸对甲苯基酯;
杂环化合物,例如2,5-二甲基-4-羟基-2H-呋喃-3-酮;2-乙基-4-羟基-5-甲基-2H-呋喃-3-酮;3-羟基-2-甲基-4H-吡喃-4-酮;2-乙基-3-羟基-4H-吡喃-4-酮;
内酯,例如1,4-辛内酯;3-甲基-1,4-辛内酯;1,4-壬内酯;1,4-癸内酯;8-癸烯-1,4-内酯;1,4-十一烷内酯;1,4-十二烷内酯;1,5-癸内酯;1,5-十二烷内酯;4-甲基-1,4-癸内酯;1,15-十五烷内酯;顺-和反-11-十五碳烯-1,15-内酯;顺-和反-12-十五碳烯-1,15-内酯;1,16-十六烷内酯;9-十六碳烯-1,16-内酯;10-氧杂-1,16-十六烷内酯;11-氧杂-1,16-十六烷内酯;12-氧杂-1,16-十六烷内酯;1,12-十二烷二酸亚乙酯;1,13-十三烷二酸亚乙酯;香豆素;2,3-二氢香豆素;八氢香豆素。
至少一种非芳香化学品载体可以为不具有或者不具有显著的感觉性能的化合物、化合物混合物或者其它添加剂。通常,如果存在于本发明芳香化学品组合物中,则至少一种非芳香化学品载体为不具有或者不具有显著的感觉性能的化合物、化合物混合物或者其它添加剂。非芳香化学品载体用于稀释和/或固定芳香化学品组合物中所含的芳香化学品,即式(I)化合物,以及任选一种或多种不同于化合物(I)的其它芳香化学品。
合适的载体材料可以为液体或油状载体材料以及蜡状或固体载体材料。
合适的液体或油状载体材料例如选自水,醇,例如甲醇或乙醇,具有20℃以下的熔融温度的脂族二醇和多元醇,例如乙二醇、甘油、二甘油、丙二醇或二丙二醇和1,2-丁二醇,环状硅氧烷,例如六甲基环三硅氧烷或十甲基环五硅氧烷、二乙二醇单甲醚,邻苯二甲酸二乙酯、肉豆蔻酸异丙酯、柠檬酸三乙酯、苯甲酸苄酯,植物油,例如分馏椰子油或者具有20℃以下的熔融温度的脂肪醇酯,例如乙酸十四烷基酯或乳酸十四烷基酯,具有20℃以下的熔融温度的甘油酯,和具有20℃以下的熔融温度的脂肪酸烷基酯,例如肉豆蔻酸异丙酯。
合适的蜡状或固体载体材料例如选自具有20℃以下的熔融温度的脂肪醇,例如肉豆蔻醇、硬脂醇或鲸蜡醇,具有20℃以上的熔融温度的多元醇,具有20℃以上的熔融温度的脂肪酸与脂肪醇的酯,例如羊毛脂、蜜蜡、巴西棕榈蜡、小烛树蜡或日本蜡,由石油制备的蜡,例如硬石蜡,水不溶性多孔矿物,例如硅胶,硅酸盐,例如滑石,微孔结晶铝硅酸盐(沸石),粘土矿物,例如膨润土,或磷酸盐,例如三聚磷酸钠,纸、纸板、木、由天然和/或合成纤维制成的织物复合物或非织造材料。
合适的载体材料还例如选自水溶性聚合物,例如聚丙烯酸酯或季铵化聚乙烯吡咯烷酮,或者水醇可溶性聚合物,例如特殊热塑性聚酯和聚酰胺。聚合物载体材料可以以各种形式,例如以凝胶、糊、固体颗粒如微胶囊或易碎涂层的形式存在。
优选,芳香化学品组合物选自如上文所定义的加香即用组合物。
一般而言,本发明芳香化学品组合物中至少一种式(I)化合物、其立体异构体或其立体异构体的混合物的总量通常适于特定的意欲用途或意欲应用,因此可经宽范围变化。通常,使用香水常用的标准商业用量。
因此,组合物中至少一种式(I)化合物、其立体异构体或其立体异构体的混合物的总量基于组合物的总重量为0.001-99.9重量%,优选0.01-90重量%,更优选0.05-80重量%,甚至更优选0.1-60重量%,特别是0.1-40重量%。
在本发明的一个实施方案中,组合物中至少一种式(I)化合物、其立体异构体或其立体异构体的混合物的总量基于组合物的总重量为0.001-5重量%,优选0.01-2重量%。
本发明另一实施方案涉及包含至少一种式(I)化合物、其立体异构体或其立体异构体的混合物和至少一种选自表面活性剂、缓和剂和溶剂的组分的组合物。
本发明一个实施方案涉及包含至少一种式(I)化合物、其立体异构体或其立体异构体的混合物和至少一种溶剂的组合物。
在本发明上下文中,“溶剂”用于稀释如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物。一些溶剂同时具有固定性能。
一种或多种溶剂可以以基于组合物0.01-99重量%存在于组合物中。在本发明一个实施方案中,组合物包含基于组合物0.1-90重量%,优选0.5-80重量%溶剂。溶剂的量可取决于组合物选择。在本发明一个实施方案中,组合物包含基于组合物0.05-10重量%,优选0.1-5重量%,更优选0.2-3重量%。在本发明一个实施方案中,组合物包含基于组合物20-70重量%,优选25-50重量%溶剂。
优选的溶剂为乙醇、二丙二醇(DPG)、丙二醇、1,2-丁二醇、甘油、二乙二醇单***、邻苯二甲酸二乙酯(DEP)、肉豆蔻酸异丙酯(IPM)、柠檬酸三乙酯(TEC)和苯甲酸苄酯(BB)。
尤其优选的溶剂选自乙醇、丙二醇、二丙二醇、柠檬酸三乙酯、苯甲酸苄酯和肉豆蔻酸异丙酯。
在本发明一个优选实施方案中,溶剂选自乙醇、异丙醇、二乙二醇单***、甘油、丙二醇、1,2-丁二醇、二丙二醇、柠檬酸三乙酯和肉豆蔻酸异丙酯。
根据另一方面,式(I)化合物、其立体异构体或其立体异构体的混合物适用于含有表面活性剂的化合物中。根据其特性香味特征,式(I)化合物、其立体异构体或其立体异构体的混合物尤其可用于含有表面活性剂的组合物如清洁剂(特别是衣物清洁剂和多用途清洁剂)的加香。
因此,本发明一个实施方案涉及包含至少一种式(I)化合物、其立体异构体或其立体异构体的混合物和至少一种表面活性剂的组合物。
表面活性剂可选自阴离子、非离子、阳离子和/或两亲或两性离子表面活性剂。含有表面活性剂的组合物,例如淋浴凝胶、泡泡浴、洗发水等优选包含至少一种阴离子表面活性剂。
本发明组合物通常包含基于组合物的总重量总计0-40重量%,优选0-20重量%,更优选0.1-15重量%,特别是0.1-10重量%的量的表面活性剂。非离子表面活性剂的典型实例为脂肪醇聚乙二醇醚、烷基苯酚聚乙二醇醚、脂肪酸聚乙二醇酯、脂肪酸酰胺聚乙二醇醚、脂肪胺聚乙二醇醚、烷氧基化甘油三酯、混合醚和混合缩甲醛、任选部分氧化的烷基(烯基)低聚糖苷或葡糖醛酸衍生物、脂肪酸-N-烷基葡糖酰胺、水解蛋白(特别是小麦基植物产品)、多元醇脂肪酸酯、糖酯、脱水山梨糖醇酯、聚山梨酸酯和胺氧化物。如果非离子表面活性剂包含聚乙二醇醚链,则它们可具有常规同系物分布,尽管它们优选具有窄范围同系物分布。
两性离子表面活性剂为分子中包含至少一个季铵基团和至少一个–COO(-)或–SO3 (-)基团的表面活性化合物。特别合适的两性离子表面活性剂为所谓的甜菜碱,例如N-烷基-N,N-二甲基甘氨酸铵,例如椰油烷基二甲基甘氨酸铵,N-酰氨基丙基-N,N-二甲基甘氨酸铵,例如椰油酰氨基丙基二甲基甘氨酸铵,和烷基或酰基中包含8-18个碳原子的2-烷基-3-羧甲基-3-羟乙基咪唑啉,和椰油酰氨基乙基羟乙基羧甲基甘氨酸盐。特别优选以Cocamidopropyl Betaine的CTFA名已知的脂肪酸酰胺。
两性表面活性剂也特别适用作助表面活性剂。两性表面活性剂为除C8-C18烷基或酰基外,分子中还包含至少一个游离氨基和至少一个-COOH-或–SO3H-基团且能够形成内盐的表面活性化合物。合适的两性表面活性剂的实例为烷基中包含约8-18个碳原子的N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚氨基二丙酸、N-羟乙基-N-烷基酰氨基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸。特别优选的两性表面活性剂为N-椰油烷基氨基丙酸酯、椰油酰氨基乙基氨基丙酸酯和酰基肌氨酸。
阴离子表面活性剂的特征是水溶性阴离子基团,例如羧酸酯、硫酸酯、磺酸酯或磷酸酯基团和亲脂性基团。皮肤安全的阴离子表面活性剂大量由从业人员由相关教课书中已知并且为市售的。它们特别是碱金属、铵或链烷醇铵盐形式的烷基硫酸盐、烷基醚硫酸盐、烷基醚羧酸盐、酰基硫氰酸盐、酰基肌氨酸盐、包含线性C12-C8烷基或酰基的酰基牛磺酸,以及碱金属或铵盐形式的磺基琥珀酸盐和酰基谷氨酸盐。
特别合适的阳离子表面活性剂为季铵化合物,优选铵卤化物,更尤其是氯化物和溴化物,例如烷基三甲基铵氯化物、二烷基二甲基铵氯化物和三烷基甲基铵氯化物,例如鲸蜡基三甲基氯化铵、硬脂基三甲基氯化铵、二硬脂基二甲基氯化铵、月桂基二甲基氯化铵、月桂基二甲基苄基氯化铵和三鲸蜡基甲基氯化铵。另外,容易生物降解的季酯化合物,例如以Stepantexe名出售二烷基铵甲硫酸盐和甲基羟烷基二烷酰氧基烷基铵甲硫酸盐和系列的相应产品可作为阳离子表面活性剂使用。“Esterquats”通常应当理解为季铵化脂肪酸三乙醇胺酯盐。它们可向组合物提供特定柔软度。它们是通过有机化学的相关方法制备的已知物质。根据本发明适用的其它阳离子表面活性剂为季铵化水解蛋白。
本发明一个实施方案涉及包含至少一种式(I)化合物、其立体异构体或其立体异构体的混合物和至少一种油组分的组合物。
油组分通常以基于组合物0.1-80,优选0.5-70,更优选1-60,甚至更优选1-50重量%,特别是1-40重量%,更特别是5-25重量%,尤其是5-15重量%的总量存在。
油组分可例如选自基于包含6-18,优选8-10个碳原子的脂肪醇的格尔伯特醇,和其它酯,例如肉豆蔻醇肉豆蔻酸酯、肉豆蔻醇棕榈酸酯、肉豆蔻醇硬脂酸酯、肉豆蔻醇异硬脂酸酯、肉豆蔻醇油酸酯、肉豆蔻醇山酸酯、肉豆蔻醇芥酸酯、鲸蜡醇肉豆蔻酸酯、鲸蜡醇棕榈酸酯、鲸蜡醇硬脂酸酯、鲸蜡醇异硬脂酸酯、鲸蜡醇油酸酯、鲸蜡醇山酸酯、鲸蜡醇芥酸酯、硬脂醇肉豆蔻酸酯、硬脂醇棕榈酸酯、硬脂醇硬脂酸酯、硬脂醇异硬脂酸酯、硬脂醇油酸酯、硬脂醇山酸酯、硬脂醇芥酸酯、异硬脂醇肉豆蔻酸酯、异硬脂醇棕榈酸酯、异硬脂醇硬脂酸酯、异硬脂醇异硬脂酸酯、异硬脂醇油酸酯、异硬脂醇山酸酯、异硬脂醇油酸酯、油醇肉豆蔻酸酯、油醇棕榈酸酯、油醇硬脂酸酯、油醇异硬脂酸酯、油醇油酸酯、油醇山酸酯、油醇芥酸酯、山醇肉豆蔻酸酯、山醇棕榈酸酯、山醇硬脂酸酯、山醇异硬脂酸酯、山醇油酸酯、山醇山酸酯、山醇芥酸酯、瓢儿菜醇肉豆蔻酸酯、瓢儿菜醇棕榈酸酯、瓢儿菜醇硬脂酸酯、瓢儿菜醇异硬脂酸酯、瓢儿菜醇油酸酯、瓢儿菜醇山酸酯和瓢儿菜醇芥酸酯、合适的还有C18-C38烷基-羟基羧酸与线性或支化C6-C22脂肪醇的酯,更尤其是苹果酸二辛酯,线性和/或支化脂肪酸与多元醇(例如丙二醇、二聚二醇或三聚三醇)的酯,基于C6-C10脂肪酸的甘油三酯,基于C6-C18脂肪酸的液体单-、二-和三甘油酯混合物,C6-C22脂肪醇和/或格尔伯特醇与芳族羧酸,更特别是苯甲酸的酯,二羧酸与包含2-10个碳原子和2-6个羟基的多元醇的酯,植物油,支化伯醇,取代环己烷,线性和支化C6-C22脂肪醇碳酸酯,例如碳酸二辛酯(Cetiol@CC),基于包含6-18,优选8-10个碳原子的脂肪醇的格尔伯特碳酸酯,苯甲酸与线性和/或支化C6-C22醇的酯(例如TN),每个烷基包含6-22个碳原子的线性或支化、对称或不对称二烷基醚,例如二辛醚(OE),环氧化脂肪酸酯与多元醇和烃的开环产物,或其混合物。
制备方法:
本发明的另一实施方案涉及制备加香即用组合物的方法,其包括将至少一种如上文所定义的式(I)化合物、其立体异构体或其立体异构体的混合物结合到即用组合物中。
该方法包括将至少一种式(I)化合物、其立体异构体或其立体异构体的混合物结合到不具有或者具有不显著的感觉性能的即用组合物中,以提供给该即用组合物特殊气味和/或特殊香味。另外,该方法还包括通过将至少一种式(I)化合物、其立体异构体或其立体异构体的混合物结合到所述即用组合物中而改进已经具有显著感觉性能的即用组合物的气味和/或香味。
优选的即用组合物为上述那些。
结合到即用组合物中的至少一种式(I)化合物、其立体异构体或其立体异构体的混合物的总量高度取决于意欲的用途或意欲的应用,因此可经宽范围变化。结合到即用组合物中的至少一种式(I)化合物、其立体异构体或其立体异构体的混合物的典型量为如上文关于组合物定义的那些。
根据本发明使用的式(I)化合物、其立体异构体或其立体异构体的混合物、可通过以上本发明方法得到的组合物以及包含它们的本发明芳香化学品组合物也可以为微胶囊形式、喷雾干燥形式、包合物形式或压出产品形式。性能可通过所谓的用对香味的更目标性释放而言合适的材料“涂覆”进一步最佳化,为此优选使用蜡质合成物质,例如聚乙烯醇。
微胶囊化可例如通过所谓的凝聚方法借助例如由聚氨酯类物质或软明胶制成的胶囊材料进行。喷雾干燥芳香油可例如通过将包含式(I)化合物、其立体异构体或其立体异构体的混合物的乳液或分散体喷雾干燥而制备,其中可使用的载体物质为改性淀粉、蛋白质、环糊精和植物胶。包合物可例如通过将芳香剂组合物和环糊精或脲衍生物的分散体引入合适的溶剂如水中而制备。可通过用合适的蜡质物质将式(I)化合物、其立体异构体或其立体异构体的混合物熔融并用随后的固化,任选在合适的溶剂如异丙醇中挤出而制备。
本发明的另一实施方案涉及通式(I.a)化合物、其立体异构体或其立体异构体的混合物:
其中:
R1a为C2-C4烷基,且
R2a为氢或C2-C4烷基。
本发明的优选实施方案涉及通式(I.a)二醚化合物,即其中R1a和R2a相互独立地选自C2-C4烷基的通式(I.a)化合物。
进一步优选其中基团R1a和R2a为相同的通式(I.a)二醚化合物。
优选的通式(I.a)化合物的实例为:
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二异丙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二异丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二异丙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷,
2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,
2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在,
2,4-二异丁氧基-1,1,3,3-四甲基-环丁烷,
2,4-二异丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,和
2,4-二异丁氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在。
更优选通式(I.a)化合物,其中基团R1a和R2a选自乙基、正丙基和异丙基。
甚至更优选通式(I.a)化合物,其中基团R1a和R2a为相同的且选自乙基、正丙基和异丙基。
特别优选的化合物(1.a)为:
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其顺式异构体的形式存在,和
2,4-二乙氧基-1,1,3,3-四甲基-环丁烷,其基本以其反式异构体的形式存在。
通式(I.a)化合物可以以顺式/反式异构体混合物的形式存在或者可分别基本以其顺式异构体或其反式异构体的形式存在。
关于表述“顺式/反式异构体混合物”和“基本存在”,参考上文关于通式(I)化合物给出的论述。
优选,通式(I.a)化合物以顺式/反式异构体混合物的形式存在。
通式(I.a)化合物可如关于通式(I)化合物所述制备。
因此,本发明还涉及制备如上文所定义的式(I.a)化合物、其立体异构体或其立体异构体的混合物的方法,其包括:
(i)使2,2,4,4-四甲基环丁烷-1,3-二醇与烷基化试剂R1a-X以及任选与烷基化试剂R2a-X在碱的存在下反应以得到粗产物混合物,其中R1a和R2a具有以上给出的含义之一,且X表示离去基团,其选自卤素,例如Cl、Br、I,和磺酸根,例如甲苯磺酸根、甲磺酸根、三氟甲磺酸根或全氟丁基磺酸根,和
(ii)使步骤(i)中所得粗产物混合物经受提纯步骤。
步骤(i)中的烷基化反应在技术人员熟知的常规烷基化反应条件下进行。
可用于烷基化反应中的合适碱如上文所定义。
为制备单醚通式(I.a)化合物,通常使2,2,4,4-四甲基环丁烷-1,3-二醇与亚等摩尔或几乎等摩尔量,例如0.7、0.8、0.9或0.95当量的烷基化试剂R1a-X反应以得到单取代化合物(I.a-OH):
其中R1a具有上文给出的含义之一,
使其进一步经受如上文所定义的提纯步骤,以除去不想要的副产物或杂质,例如残余原料或相应的二取代化合物。
基团R1a和R2a为相同的通式(I.a)二醚化合物的制备通常通过使2,2,4,4-四甲基环丁烷-1,3-二醇分别与至少2当量,例如2.0、2.1、2.5或3.0当量的烷基化试剂R1a-X或R2a-X反应而进行,其中基团R1a、R2a和X具有以上给出的含义之一,随后使所得粗产物经受如上文所定义的提纯步骤。
其中基团R1a和R2a不同的通式(I)二醚化合物的制备通常通过首先使2,2,4,4-四甲基环丁烷-1,3-二醇与亚等摩尔或几乎等摩尔量,例如0.7、0.8、0.9或0.95当量的烷基化试剂R1-X反应以得到单取代化合物(I.-a-OH),在提纯步骤以后,使其进一步与第二烷基化试剂R2a-X反应而进行。
一般而言,原料2,2,4,4-四甲基环丁烷-1,3-二醇作为顺式/反式异构体混合物应用。因此,化合物I.a通常作为顺式/反式异构体的混合物得到。
在制备式(I.a)化合物的方法的步骤(ii)中,使步骤(i)中所得粗产物混合物经受提纯步骤,以除去不想要的副产物或杂质,例如残余单取代化合物(I.a-OH),以及如果需要的话分离顺式/反式异构体。
一般而言,步骤(ii)中的提纯可通过使用常规提纯方法,例如结晶、蒸馏或色谱法,例如柱色谱或高效液相色谱进行。如果仅次要量的杂质和副产物存在于粗产物混合物中,则提纯步骤也可借助简单的萃取后处理进行。如果需要的话,顺式/反式异构体可通过分馏结晶、柱色谱或高效液相色谱分离。作为选择,顺式/反式异构体也可通过使用如US 3,227,764所述的方法分离。
本发明另一实施方案涉及通式(I.b)化合物、其立体异构体或其立体异构体的混合物:
其中:
R1b为-(C=O)-R3,
R2b为氢或-(C=O)-R4,且
R3和R4相互独立地选自氢和C1-C4烷基,条件是如果存在的话,R3和R4是不同的。
本发明的一个优选实施方案涉及通式(I.b)的二醚化合物,即其中R2b为-(C=O)-R4的通式(I.b)化合物。
进一步优选通式(I.b)化合物,其中R3和R4选自氢和C1-C3烷基,特别是选自氢、甲基和乙基。
通式(I.b)化合物可如关于通式(I)的酯化合物所述制备。
因此,本发明还涉及制备如上文所定义的式(I.b)化合物、其立体异构体或其立体异构体的混合物的方法,其包括:
(i)使2,2,4,4-四甲基环丁烷-1,3-二醇与羧酸R3-COOH或其酐或者与酸性卤化物R3-(C=O)X'在有机碱的存在下以及任选与羧酸R4-COOH或其酐,或者与酸性卤化物R4-(C=O)X'反应以得到粗产物混合物,其中R3和R4具有以上给出的含义之一,且X'表示卤素,例如Cl、Br或I,和
(ii)使步骤(i)中所得粗产物混合物经受提纯步骤。
实施例
分析:
产物的纯度通过气相色谱法(面积%)测定:
对于酯:
GC体系:Agilent 7890B;
GC柱:CP-SIL 13(50m(长度)、0.32mm(ID)、1.2μm(膜));
温度程序:以3°/min从120℃至200℃,以20°/min从200℃至250℃。
对于醚:
GC体系:Agilent 6890N;
GC柱:DB1(30m(长度)、0.25mm(ID)、0.25μm(膜));
温度程序:在10℃下注射,以3°/min从50℃至120℃,以20°/min从120℃至200℃。
1.制备实施例
1.1甲酸(3-甲酰氧基-2,2,4,4-四甲基-环丁基)酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 10g | 0.069 |
甲酸 | 46.03 | 22.3g | 0.485 |
乙酸酐 | 102.09 | 42.5g | 0.416 |
N,N'-二甲基氨基吡啶 | 122.17 | 0.17g | 0.001 |
四氢呋喃 | 70mL |
在0℃下,将甲酸缓慢地加入乙酸酐中。在55℃下将混合物搅拌2小时。然后将混合物冷却至0℃并加入20mL THF,在该温度下,缓慢地加入醇在50mL THF中的溶液。在添加以后,将DMAP加入混合物中。将反应在室温下搅拌3.5小时,并通过GC观察完全转化。将60mL甲苯加入混合物中并将有机相用30mL水洗涤3次。将有机相用硫酸钠干燥,并在实验室蒸发器中除去溶剂以得到9.7g的包含96%二-甲酸酯(根据GC面积%)的粗产物。通过硅胶色谱法将粗产物提纯。相应二-甲酸酯以99.2%(GC面积%)的纯度得到。NMR表明产物作为比55:45的顺式:反式异构体存在。
产物的表征:
GC:99.2%纯度(GC面积%)
13C-NMR:
1.2乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 75g | 0.520 |
乙酸酐 | 102.09 | 146g | 1.430 |
N,N‘-二甲基氨基吡啶 | 122.17 | 1.906g | 0.016 |
四氢呋喃 | 350mL |
在RF下将DMAP加入二醇的THF溶液中。将混合物设置至回流(53℃),并在该温度下缓慢地加入乙酸酐(2.25当量)。在2小时以后,观察到99%二醇转化率。然而,在混合物中发现约15%单乙酸酯,为此,将0.5当量乙酸酐加入反应中。在3小时以后,在回流下,通过GC观察到97%的至二乙酸酯的转化率。将反应降至室温并用150mL水缓慢地骤冷,加入300mL乙酸乙酯和200mL水。将有机相分离,并用NaHCO3和盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,得到102.2g的包含>97%二乙酸酯(根据GC面积%)的粗产物。通过蒸馏将产物提纯。相应的二乙酸酯以99.6%(GC面积%)的纯度得到。NMR表明产物作为比55:45的顺式:反式异构体存在。
产物的表征:
GC:99.6%纯度(GC面积%)
13C-NMR:
1.3丙酸(3-丙酰氧基-2,2,4,4-四甲基-环丁基)酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 8g | 0.055 |
丙酰氯 | 92.52 | 12.83g | 0.139 |
N,N‘-二甲基氨基吡啶 | 122.17 | 0.120g | 0.001 |
三乙胺 | 101.19 | 14g | 0.139 |
己烷 | 100mL |
将醇、三乙胺和DMAP在己烷(50mL)中的溶液冷却至0℃。在该温度下,缓慢地加入丙酰氯。将反应在室温下搅拌1小时,加入50mL己烷,并将反应在回流(67℃)下搅拌1小时。在该时间以后,通过GC观察完全转化。将反应降至室温,并用30mL水缓慢地骤冷,加入50mL己烷,并将有机相用NaHCO3和盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,得到13g的包含64%二丙酸酯(根据GC面积%)和25%单丙酸酯(GC面积%)的粗产物。通过硅胶色谱法将产物提纯。相应的二丙酸酯以94%(GC面积%)的纯度得到。NMR表明产物作为比1:1的顺式:反式异构体存在。
产物的表征:
GC:94%纯度(GC面积%)
13C-NMR:
1.4 2,2-二甲基丙酸[3-(2,2-二甲基丙酰氧基)-2,2,4,4-四甲基-环丁基]酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 50g | 0.347 |
新戊酰氯 | 120.58 | 156.754g | 1.3 |
N,N‘-二甲基氨基吡啶 | 122.17 | 2.118g | 0.017 |
三乙胺 | 101.19 | 87.710g | 0.867 |
THF | 250mL |
将醇、三乙胺和DMAP在THF中的溶液冷却至0℃。在该温度下,缓慢地加入新戊酰氯(2.5)。将反应在室温下搅拌0.5小时,并在回流下搅拌4小时。在该时间以后,观察到96%转化率,然而,通过GC仅检测到49%二新戊酸酯,其余为单衍生物。因此,进一步加入1.25当量新戊酰氯,并将反应在RF下搅拌21小时。将反应降至室温并用200mL水缓慢地骤冷,加入200mL乙酸乙酯并将有机相用NaHCO3和盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,得到110.8g的包含88%二新戊酸酯(根据GC面积%)和11%单新戊酸酯(GC面积%)的粗产物。通过蒸馏将产物提纯。相应的二新戊酸酯以99.8%(GC面积%)的纯度得到。NMR表明产物作为比55:45的顺式:反式异构体存在。
产物的表征:
GC:99.8%纯度(GC面积%)
13C-NMR:
1.5 2-甲基丙酸[3-(2-甲基丙酰氧基)-2,2,4,4-四甲基-环丁基]酯
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 10g | 0.069 |
异丁酸酐 | 158.19 | 24.68g | 0.156 |
N,N‘-二甲基氨基吡啶 | 122.17 | 0.254g | 0.03 |
四氢呋喃 | 50mL |
在RF下将DMAP加入二醇的THF溶液中。将混合物设置至回流(60℃),并在该温度下缓慢地加入异丁酸酐(2.25当量)。在2.5小时以后,观察到99%二醇转化率。然而,在混合物中发现约8%单异丁酸酯。将反应降至室温并用20mL水、50mL乙酸乙酯缓慢地骤冷。将有机相分离,并用NaHCO3和盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,得到19.6g的包含>91%二异丁酸酯(根据GC面积%)的粗产物。通过蒸馏将产物提纯。相应的二异丁酸酯以97.4%(GC面积%)的纯度得到。NMR表明产物作为比55:45的顺式:反式异构体存在。
产物的表征:
GC:97.4%纯度(GC面积%)
13C-NMR:
1.6丁酸(3-丁酰氧基-2,2,4,4-四甲基-环丁基)酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 10g | 0.069 |
正丁酸酐 | 158.19 | 24.68g | 0.156 |
N,N‘-二甲基氨基吡啶 | 122.17 | 0.254g | 0.03 |
四氢呋喃 | 50mL |
在RF下将DMAP加入二醇的THF溶液中。将混合物设置至回流(60℃)并在该温度下缓慢地加入正丁酸酐(2.25当量)。在2.5小时以后,观察到99%二醇转化率。然而,在混合物中发现约10%单-正丁酸酯。将反应降至室温并用20mL水、50mL乙酸乙酯缓慢地骤冷。将有机相分离,并用NaHCO3和盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,得到18.8g的包含>88%二-正丁酸酯(根据GC面积%)的粗产物。通过蒸馏将产物提纯。相应的二-正丁酸酯以99.7%(GC面积%)的纯度得到。NMR表明产物作为比55:45的顺式:反式异构体存在。
产物的表征:
GC:99.7%纯度(GC面积%)
13C-NMR:
1.7 2,4-二甲氧基-1,1,3,3-四甲基-环丁烷的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 30g | 0.208 |
甲基碘 | 141.94 | 73.82g | 0.520 |
氢化钠 | 23.99 | 12.476g | 0.520 |
四氢呋喃 | 300mL |
在0℃下,向氢化钠(2.5当量)在150mL THF中的分散体中加入笼状二醇在150mLTHF中的溶液。将混合物在0℃下搅拌1小时。在该时间以后,在RT下缓慢地加入2.5当量甲基碘。在添加以后,将混合物在40℃下搅拌21小时。此时,将反应用150mL水缓慢地骤冷。将有机相用150mL MTBE萃取3次。将有机萃取物结合,并用150mL NH3溶液和150mL盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下将溶剂蒸发以后,得到18.8g的具有54%二甲醚(根据GC面积%),其余为单甲基化醇(30%)和未反应笼状二醇(10%)的粗产物。通过硅胶色谱法将二甲醚产物提纯。相应的二甲醚以99.8%(GC面积%)的纯度得到。NMR表明产物作为比4:1的顺式:反式异构体存在。
产物的表征:
GC:99.8%纯度(GC面积%)
13C-NMR:
1.8 3-甲氧基-2,2,4,4-四甲基-环丁醇的制备
在实施例1.7中的2,4-二甲氧基-1,1,3,3-四甲基-环丁烷提纯期间,将相应单甲醚的两种异构体分离。1.4g的3-甲氧基-2,2,4,4-四甲基-环丁醇的高反式异构体(高反式)以纯度94%(94%反式,GC面积%,RT:20.70分钟)得到。NMR证明存在高含量的反式异构体。
产物(高反式)的表征:
GC:94%纯度(94%反式(根据GC面积%);RT:20.70分钟)
13C-NMR:
0.5g的3-甲氧基-2,2,4,4-四甲基-环丁醇的高顺式异构体以98%(98%顺式,GC面积%,RT:20.30分钟)的纯度很好地分离。与3-甲氧基-2,2,4,4-四甲基-环丁醇的顺式/反式异构体混合物相比,GC证明高顺式异构体的存在。
产物(高顺式)的表征:
GC:98%纯度(98%顺式(根据GC面积%);RT:20.30分钟)。
1.9 2,4-二乙氧基-1,1,3,3-四甲基-环丁烷的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2244-四甲基-环丁烷-13-二醇 | 144.21 | 20g | 0.139 |
乙基碘 | 155.97 | 82.25g | 0.527 |
氢化钠 | 23.99 | 12.65g | 0.527 |
四氢呋喃 | 200mL |
在0℃下,向7.65g氢化钠(2.3当量)在100mL THF中的分散体中,缓慢地加入笼状二醇在150mL THF中的溶液。在0℃下将混合物搅拌1小时。在该时间以后,在RT下缓慢地加入2.3当量乙基碘(49.75g)。在添加以后,将混合物在40℃下搅拌21小时。此时,观察到约90%醇转化率。然而,仅检测到35%二***,其余(56%)为单醚衍生物。因此,将反应冷却至0℃,并加入5g氢化钠。在该温度下15分钟以后,缓慢地加入32.5g乙基碘。在40℃下在22小时期间搅拌混合物。然后将反应用100mL水缓慢地骤冷。将有机相用100mL MTBE萃取3次。将有机萃取物结合,并用100mL NH3溶液和100mL盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下将溶剂蒸发以后,得到22.8g的具有61.5%二***(根据GC面积%),其余为单乙基化醇(29%)和未反应笼状二醇的粗产物。通过硅胶色谱法将产物提纯。相应的二***以99.8%(GC面积%)的纯度得到。NMR表明产物作为比3:1的顺式:反式异构体存在。
产物的表征:
GC:99.8%纯度(GC面积%)
13C-NMR:
1.10 3-乙氧基-2,2,4,4-四甲基-环丁醇的制备
在实施例1.9的2,4-二乙氧基-1,1,3,3-四甲基-环丁烷的提纯期间,2.9g单***(3-乙氧基-2,2,4,4-四甲基-环丁醇)还以79%(GC面积%)的纯度分离,其余为20.5%二***衍生物(2,4-二乙氧基-1,1,3,3-四甲基-环丁烷)。NMR信息表明关于3-乙氧基-2,2,4,4-四甲基-环丁醇的55:45的反式:顺式比,和关于2,4-二乙氧基-1,1,3,3-四甲基-环丁烷的3:1的顺式/反式比。
产物的表征:
GC:79%纯度(GC面积%)
13C-NMR:
1.11 2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 10g | 0.069 |
1-碘丙烷 | 169.99 | 27.11g | 0.159 |
氢化钠 | 23.99 | 3.83g | 0.159 |
四氢呋喃 | 105mL |
在0℃下,向3.83g氢化钠(2.3当量)在75mL THF中的分散体中,缓慢地加入笼状二醇在30mL THF中的溶液。在0℃下将混合物搅拌30分钟。在该时间以后,在RT下缓慢地加入2.3当量1-碘丙烷(27.11g)。在添加以后,将混合物在50℃下搅拌4小时。此时观察到约80%醇转化率。然而,仅检测到12%二-正丙醚,其余(约65%)为单醚衍生物。因此,将反应冷却至0℃,并加入1.67g氢化钠。在该温度下30分钟以后,缓慢地加入11.8g1-碘丙烷。在50℃下在18小时期间搅拌混合物。然后将反应用50mL水缓慢地骤冷。将有机相用50mL MTBE萃取3次。将有机萃取物结合,并用50mL NH3溶液和30mL盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下将溶剂蒸发以后,粗产物包含22%二-正丙醚(根据GC面积%),其余为单-正丙基化醇(67%)和未反应笼状二醇。通过硅胶色谱法将产物提纯。相应的二-正丙醚(0.7g)以99.4%(GC面积%)的纯度得到。NMR表明产物作为比85:15的顺式:反式异构体存在。
产物的表征:
GC:99.4%纯度(GC面积%)
13C-NMR:
1.12 3-丙氧基-2,2,4,4-四甲基-环丁醇的制备
在实施例1.11的2,4-二-正丙氧基-1,1,3,3-四甲基-环丁烷的提纯期间,0.6g单-正丙醚(3-丙氧基-2,2,4,4-四甲基-环丁醇)还以99%(GC面积%)的纯度分离。NMR表明3:2反式:顺式比。
产物的表征:
GC:99%纯度(GC面积%)
13C-NMR:
1.13 2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷的制备
在0℃下,向3.83g氢化钠(2.3当量)在75mL THF中的分散体中缓慢地加入笼状二醇在30mL THF中的溶液。在0℃下将混合物搅拌30分钟。在该时间以后,在RT下缓慢地加入2.3当量1-碘丁烷(29.35g)。在添加以后,将混合物在50℃下搅拌22小时。此时,观察到约75%醇转化率。然而,仅检测到12%二-正丁醚,其余(约65%)为单醚衍生物(根据GC面积%)。然后将反应用50mL水缓慢地骤冷。将有机相用50mL MTBE萃取3次。将有机萃取物结合,并用50mL NH3溶液和30mL盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,通过硅胶色谱法将粗产物提纯。相应的二-正丁醚(1.6g)以96%(GC面积%)的纯度提供。NMR表明产物作为比85:15的顺式:反式异构体存在。
产物的表征:
GC:96%纯度(GC面积%)
13C-NMR:
原子数 | 测量的<sup>13</sup>C位移(多次) |
C1/C3 | 84.99/86.84(d) |
C2/C4 | 42.37/40.86(s) |
C5/C8/C6/C7 | 15.72(顺式)/23.60(反式)/30.91(顺式)(q) |
C9/C13 | 72.66/70.18(t) |
C10/C14 | 32.10/32.18(t) |
C11/C15 | 19.44/19.41(t) |
C12/C16 | 14.04/13.97(q) |
1.14 3-丁氧基-2,2,4,4-四甲基-环丁醇的制备
在实施例1.13中的2,4-二-正丁氧基-1,1,3,3-四甲基-环丁烷提纯期间,2g单-正丁醚(3-丁氧基-2,2,4,4-四甲基-环丁醇)还以99%(GC面积%)的纯度分离。NMR表明60:40顺式/反式比。
产物的表征:
GC:GC:99%纯度(GC面积%)
13C-NMR:
原子数 | 测量的<sup>13</sup>C位移(多次) |
C1 | 79.74/78.37(d) |
C2/C4 | 42.76/40.87(s) |
C3 | 86.74(反式)/85.02(顺式)(d) |
C5/C6/C7/C8 | 29.87(顺式)/22.84(反式)/23.13(反式)/15.33(顺式)(q) |
C11 | 70.55/70.31(t) |
C12 | 32.12/32.09(t) |
C13 | 19.44(t) |
C14 | 14.03(q) |
1.15 2,4-二-叔丁氧基-1,1,3,3-四甲基-环丁烷的制备
将10g笼状二醇溶于140mL甲基叔丁醚(MTBE)中,并加入10g分子筛4A。在25℃下,向该分散体中缓慢地加入硫酸。将反应在40℃下搅拌6小时。此后,观察到约90%二醇转化率。将分子筛过滤并向反应中缓慢地加入50mL NaHCO3。在相分离以后,将水相用30mL MTBE萃取两次。将有机萃取物结合,用50mL NaHCO3洗涤并用硫酸钠干燥。在降低的压力下将溶剂蒸发以后,通过硅胶色谱法将粗产物提纯。相应的2,4-二-叔丁氧基-1,1,3,3-四甲基-环丁烷(0.9g)以90%(GC面积%)的纯度得到。NMR表明产物作为比2:1的顺式:反式异构体存在。
产物的表征:
GC:GC:90%纯度(GC面积%)
13C-NMR:
原子数 | 测量的<sup>13</sup>C位移(多次) |
C1/C3 | 78.27(d) |
C2/C4 | 43.63/41.36(s) |
C5/C6/C7/C8 | 29.83(顺式)/23.29(反式)/16.71(顺式)(q) |
C11 | 71.69/71.35(s) |
C12/C13/C14/C15/C16/C17/C18 | 28.74(q) |
1.16 3-叔丁氧基-2,2,4,4-四甲基-环丁醇的制备
在实施例1.15中的2,4-二-叔丁氧基-1,1,3,3-四甲基-环丁烷提纯期间,1.1g单叔丁基醚(3-叔丁氧基-2,2,4,4-四甲基-环丁醇)还以90%(GC面积%)的纯度分离。NMR表明3:2反式:顺式比。
产物的表征:
GC:GC:90%纯度(GC面积%)
13C-NMR:
1.17具有9:1的顺式/反式异构体的乙酸(3-乙酰氧基-2,2,4,4-四甲基-环丁基)酯的制备
将68.5g的实施例1.2中制备的纯二乙酸酯试样在冰箱中设定两分钟,并观察结晶如何开始。因此,将试样在冷冻室中保持30分钟。此时试样完全为固体。此后,将试样保持在RT下,并观察晶体如何缓慢地变成液体。将10mL的该二元混合物部分过滤,并通过GC分析两个部分。液体部分包含顺式:反式混合物52:48(根据GC面积%)。然而,晶体为9:1顺式:反式混合物(根据GC面积%和NMR)。
产物的表征:
GC:9:1顺式/反式异构体混合物
13C-NMR:
1.18乙酸(3-羟基-2,2,4,4-四甲基-环丁基)酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇 | 144.21 | 10g | 0.069 |
乙酸酐 | 102.09 | 7.08g | 0.069 |
N,N‘-二甲基氨基吡啶 | 122.17 | 0.254g | 0.002 |
四氢呋喃 | 50mL |
在RF下将DMAP加入二醇的THF溶液中。将混合物设置至40℃并在该温度下缓慢地加入乙酸酐(1当量)。在3小时以后,将反应降至室温并用50mL水、50mL乙酸乙酯缓慢地骤冷。将有机相分离,并用NaHCO3和盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,得到7.2g的包含17.4%笼状二醇、46.7%单乙酸酯和35.7%二乙酸酯(根据GC面积%)的粗产物。通过硅胶色谱法将产物提纯。相应单乙酸酯以99%(GC面积%)的纯度作为比1:1的顺式:反式异构体混合物(GC分析)得到。
1.19乙酸(3-甲酰氧基-2,2,4,4-四甲基-环丁基)酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇的单乙酸酯 | 186.25 | 7g | 0.025 |
甲酸 | 46.03 | 7.98g | 0.173 |
乙酸酐 | 102.09 | 15.17g | 0.149 |
N,N‘-二甲基氨基吡啶 | 122.17 | 0.061g | 0.0005 |
四氢呋喃 | 40mL |
在0℃下,将甲酸缓慢地加入乙酸酐中。在55℃下将混合物搅拌2小时。然后将混合物冷却至0℃并加入20mL THF,在该温度下,缓慢地加入粗单乙酸酯衍生物(如前文所述制备)在20mL THF中的溶液。在添加以后,将DMAP加入混合物中。将反应在室温下搅拌3.5小时。将50mL甲苯加入混合物中,并将有机相用50mL水洗涤三次。将有机相用硫酸钠干燥,并在实验室蒸发器中除去溶剂以得到6.8g的包含19.12%单甲酸酯、43%单乙酸酯-单甲酸酯和33%二乙酸酯(根据GC面积%)的粗产物。通过硅胶色谱法将粗产物提纯。相应单乙酸酯-单甲酸酯以52%(GC面积%)的纯度与28%单甲酸酯和18%二乙酸酯(根据GC面积%)一起分离。所有化合物具有约1:1顺式/反式比(根据GC面积%)。
1.20乙酸(3-甲氧基-2,2,4,4-四甲基-环丁基)酯的制备
化合物 | MW | 质量/体积 | 摩尔数 |
2,2,4,4-四甲基-环丁烷-1,3-二醇的单甲醚 | 158.24 | 7g | 0.033 |
乙酸酐 | 102.09 | 3.387g | 0.033 |
N,N‘-二甲基氨基吡啶 | 122.17 | 0.244g | 0.002 |
四氢呋喃 | 50mL |
在RT下将122mg DMAP加入2,2,4,4-四甲基-环丁烷-1,3-二醇的单甲醚衍生物的THF溶液中。用作原料的单甲醚衍生物如前文所述,用1.3当量MeI制备。该反应以后得到的原料具有约50%含量的单甲醚衍生物,并且不经进一步提纯而用于该合成中。
将混合物设置至40℃并在该温度下缓慢地加入乙酸酐(1当量)。在5小时以后,观察到醇的不完全转化,并将122mg DMAP加入混合物中。将反应在40℃下搅拌4小时更久。此后,将反应降至室温并用50mL水、50mL乙酸乙酯缓慢地骤冷。将有机相分离,并用NaHCO3和盐水溶液洗涤。将有机萃取物结合,并用硫酸钠干燥。在降低的压力下使溶剂蒸发以后,得到5.6g的包含32%混合醚-酯衍生物,其余为甲醚(21%)和二乙酸酯(30%)(根据GC面积%)的粗产物。通过硅胶色谱法将产物提纯。相应单甲醚-单乙酸酯以72%(GC面积%)的纯度作为比1:1的顺式:反式异构体混合物得到,其余为二甲醚。NMR也证明了产物分布。
2.嗅觉试验
为测试本发明化合物(I)的气味质量和强度,进行香水条试验。
为此,将吸收纸条浸入包含待测试化合物(I)的1-10重量%乙醇溶液的溶液中。在溶剂蒸发(约30秒)以后,由熟练调香师嗅觉评估香味印象。
香味试验结果汇总于表1中。
表1:香味试验结果
Claims (18)
2.根据权利要求1的用途,其中在式(I)中,
R1为C1-C4烷基,且
R2为氢或C1-C4烷基。
3.根据权利要求2的用途,其中式(I)化合物具有以下特征a)、b)、c)和/或d)中的至少一个:
a)R2为C1-C4烷基,
b)R1和R2为相同的,
c)R1和R2为C1-C3烷基,
d)R1和R2为甲基或乙基。
4.根据权利要求2的用途,其中在式(I)中,
R1为C1-C4烷基,且
R2为氢。
5.根据权利要求1的用途,其中在式(I)中,
R1为-(C=O)-R3,且
R2为氢或-(C=O)-R4。
6.根据权利要求5的用途,其中式(I)化合物具有以下特征e)、f)、g)、h)和/或i)中的至少一个:
e)R2为-(C=O)-R4,
f)R3和R4为相同的,
g)R3和R4选自氢和C1-C3烷基,
h)R3和R4选自氢、甲基和乙基,
i)R3和R4为甲基。
7.根据权利要求1的用途,其中在式(I)中,
R1为C1-C4烷基,且
R2为-(C=O)-R3。
8.根据前述权利要求中任一项的用途,用于选自香料组合物、化妆品组合物、身体护理组合物、口腔和牙齿卫生用产品、卫生制品、清洁组合物、织物洗涤剂组合物、器皿洗涤组合物、香水分配器用组合物、食品、食品增补剂、药物组合物和作物保护组合物的组合物中。
9.芳香化学品组合物,其包含至少一种根据权利要求1-7中任一项的式(I)化合物、其立体异构体或其立体异构体的混合物,和至少一种选自不同于化合物(I)的其它芳香化学品和非芳香化学品载体的其它化合物。
10.根据权利要求9的组合物,其选自香料组合物、化妆品组合物、身体护理组合物、口腔和牙齿卫生用产品、卫生制品、清洁组合物、织物洗涤剂组合物、器皿洗涤组合物、香水分配器用组合物、食品、食品增补剂、药物组合物和作物保护组合物。
11.一种制备加香即用组合物的方法,其包括将至少一种根据权利要求1-7中任一项的式(I)化合物、其立体异构体或其立体异构体的混合物结合到即用组合物中。
12.根据权利要求1-7中任一项的式(I)化合物、其立体异构体或其立体异构体的混合物在改进加香即用组合物的香味特征中的用途。
14.根据权利要求13的化合物,其中式(I.a)化合物具有以下特征j)、k)和/或l)中的至少一个:
j)R1a和R2a相互独立地选自C2-C4烷基,
k)R1a和R2a为相同的,
l)R1a和R2a选自乙基、正丙基和正丁基。
16.根据权利要求15的化合物,其中式(I.b)化合物具有以下特征m)、n)和/或o)中的至少一个:
m)R2b为-(C=O)-R4,
n)R3和R4选自氢和C1-C3烷基,
o)R3和R4选自氢、甲基和乙基。
17.一种制备根据权利要求13-14中任一项的式(I.a)化合物、其立体异构体或其立体异构体的混合物的方法,其包括:
(i)使2,2,4,4-四甲基环丁烷-1,3-二醇与烷基化试剂R1a-X以及任选与烷基化试剂R2a-X在碱的存在下反应以得到粗产物混合物,其中R1a和R2a具有以上给出的含义之一,且X表示离去基团,其选自卤素,例如Cl、Br、I,和磺酸根,例如甲苯磺酸根、甲磺酸根、三氟甲磺酸根或全氟丁基磺酸根,和
(ii)使步骤(i)中所得粗产物混合物经受提纯步骤。
18.一种制备根据权利要求15-16中任一项的式(I.b)化合物、其立体异构体或其立体异构体的混合物的方法,其包括:
(i)使2,2,4,4-四甲基环丁烷-1,3-二醇与羧酸R3-COOH或其酐,或者与酸性卤化物R3-(C=O)X'在有机碱的存在下以及任选与羧酸R4-COOH或其酐,或者与酸性卤化物R4-(C=O)X'反应以得到粗产物混合物,其中R3和R4具有以上给出的含义之一,且X'表示卤素,例如Cl、Br或I,
(ii)使步骤(i)中所得粗产物混合物经受提纯步骤。
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PCT/EP2018/074002 WO2019048544A1 (en) | 2017-09-06 | 2018-09-06 | 2,2,4,4-TETRAMETHYLCYCLOBUTANE -1,3-DIOL ESTERS AND ETHERS FOR USE AS AROMATIC CHEMICALS |
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DE1114811B (de) | 1959-04-13 | 1961-10-12 | Eastman Kodak Co | Verfahren zur Herstellung von als Schmiermittel geeigneten Estern von Cyclobutan-1, 3-diolen |
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US3043791A (en) | 1959-09-28 | 1962-07-10 | Eastman Kodak Co | Plastic composition comprising polyvinyl chloride and an ester of 2, 2, 4, 4-tetra alkyl cyclobutane-1, 3-diol |
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