CN105189425B - 制备3,7-二甲基壬-1-醇的方法 - Google Patents
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Abstract
本发明涉及新的经改进的制备3,7‑二甲基壬‑1‑醇的方法。
Description
本发明涉及新的经改进的制备3,7-二甲基壬-1-醇的方法。
3,7-二甲基壬-1-醇(式(I)的化合物)又名乙基四氢香叶醇(E-THGOL),其可用于香味和香料应用领域中。
3,7-二甲基壬-1-醇是已知的化合物(CAS 86414-50-8),即,其被描述于Biosci.Biotechol.Biochem.,66(2),2002,P.582-587。
本发明的目标是找到更简单(即更少步骤)且导致很好产率和高转化率的合成。
新发现的制备E-THGOL的方法是从3,7-二甲基壬-6-烯基-1-炔基-3-醇(式(II)的化合物)开始经由3,7-二甲基壬-2,6-二烯醛(式(III)的化合物)的两步法。
起始材料3,7-二甲基壬-6-烯基-1-炔基-3-醇(式(II)的化合物)是已知的化合物且可商购。其还可以根据现有技术(即WO2004/018400)中所述的方法来生产。
3,7-二甲基壬-2,6-二烯醛又名E-柠檬醛,其也可用于香味和香料应用领域中。
两个步骤的产物的产率和转化率都很好。式(II)的化合物的E/Z异构性(几何异构性)和式(III)的化合物的E/Z异构性(几何异构性)对反应并不关键。式(II)的化合物和式(III)的化合物可以是单一的异构形式以及异构形式的混合物。
根据本发明的新方法是以下所列:
步骤(i):
该反应是使用催化剂的重排反应。所述重排在现有技术(即Helvetica ChimicaActa,Vol.59.Fasc.4,P.1233-1243(1976))中是已知的。
该反应在作为溶剂的脂族烃和/或芳族烃中进行。可以使用单一的溶剂以及溶剂的混合物。优选使用高沸点烃。
所述溶剂的例子是石蜡油、己烷、二甲苯。
步骤(i)的反应通常在提高的温度下进行。通常在至少50℃的温度下进行。步骤(i)的反应优选在50-200℃的温度下进行。
步骤(i)的反应通常在常压下进行。其也可以在较低或较高压力下进行。
步骤(i)的反应通常在催化剂存在下进行。优选的催化剂是式(IV)的化合物
其中,R1、R2和R3彼此独立地为直链的或支化的C1-C10-烷基基团(moiety)或Si(R4)3,其中每个R4彼此独立地为直链的或支化的C1-C10-烷基基团或者被取代的或未被取代的的苯基。
优选的是式(IV)的催化剂,其中R1、R2和R3具有完全相同的含义。
更优选的是式(IV)的催化剂,其中R1、R2和R3具有完全相同的含义并且其中R1、R2和R3为直链的或支化的C1-C4-烷基基团或Si(R4)3,其中每个R4为直链的或支化的C1-C4-烷基基团或者被取代的或未被取代的的苯基。
作为催化剂,最优选的是式(IV’)的催化剂
在反应结束时,通过蒸馏将产物从反应混合物中除去。通常使用真空蒸馏。
步骤(ii):
该步骤是氢化反应。
通常通过使用H2-气体来进行氢化。
可以(且优选)使用纯净的H2-气体,但也可以使用包含H2的气体混合物。
因此,本发明涉及如上所述的方法,其中通过使用(纯净的)H2-气体来进行氢化。
氢化通常在压力下进行。压强优选地为至少1.5bar。通常使用不高于50bar的压强。压强的优选范围是1.5-40bar,更优选地2-30bar。
氢化通常在适合耐受压力的容器中进行。
氢化在金属催化剂存在下进行,优选在镍催化剂存在下进行。
根据本发明的方法中所使用的镍催化剂是非均相催化剂。
优选的催化剂是镍合金催化剂。这类催化剂又名“骨架催化剂”或“海绵金属催化剂”。
这类催化剂可商购,例如,来自BASF的商品名为的催化剂(即ActimetM)或来自Evonik的产品名为B 111W、B 112、B 113W、B 113Z的催化剂或来自JohnsonMatthey Catalysts的JM A4000、JM A40A9、JM A2000或来自CatAlloy的(即Acticat 1000、Acticat 1100、Acticat 1200、Acticat 1600)。
催化剂可被重复用于进一步的氢化反应且催化剂还可容易地回收。
通常,催化剂无需进一步处理即可使用。因此,可以分批或连续进行氢化。
氢化反应混合物中E-柠檬醛与催化剂的比率(与重量相关)通常为至少5∶1。
E-柠檬醛的氢化在溶剂(或溶剂混合物)中进行或不使用任何溶剂进行。
换言之,本申请的一种实施方式是在步骤(ii)中无溶剂氢化。无溶剂表示没有通常量的这类化合物。这表示:起始材料中没有加入溶剂。
但氢化中所使用的一些材料可包含痕量溶剂,这些痕量溶剂可源自它们的生产。但这类杂质的量很少,少于10%且一般少于2%。
对于步骤(ii)中的氢化,也可以使用溶剂或溶剂的混合物。合适的溶剂是直链的、支化的或环状的具有5-10个碳原子的脂族烃、具有5-10个碳原子的芳族烃、酯、醚和醇。
优选使用在常规条件(normal conditions)下是液体的溶剂,这允许容易的操作。
优选的溶剂是THF、正己烷、正庚烷、2-丙醇、甲苯和乙酸乙酯。
因此,本发明涉及制备3,7-二甲基壬-1-醇(式(I)的化合物)的方法(A),
其特征在于:在第一步骤(i)中,
使式(II)的化合物
经受重排反应,其中获得式(III)的化合物
且在第二步骤(ii)中,
通过使用金属催化剂来将式(III)的化合物还原为式(I)的化合物。
本发明还涉及方法(B),其是方法(A),其中在步骤(i)中使用式(IV)的催化剂
其中,R1、R2和R3彼此独立地为直链的或支化的C1-C10-烷基基团或Si(R4)3,其中每个R4彼此独立地为直链的或支化的C1-C10-烷基基团或者被取代的或未被取代的的苯基。
本发明还涉及方法(B’),其是方法(B),其中在步骤(i)中使用式(IV)的催化剂,其中R1、R2和R3具有完全相同的含义,且其中,R1、R2和R3为直链的或支化的C1-C4-烷基基团或Si(R4)3,其中每个R4为直链的或支化的C1-C4-烷基基团或者被取代的或未被取代的的苯基。
本发明还涉及方法(B”),其是方法(B),其中在步骤(i)中使用式(IV’)的催化剂
本发明还涉及方法(C),其是方法(A)、(B)、(B’)或(B”),其中在步骤(i)中,反应在作为溶剂的至少一种烃中进行。
本发明还涉及方法(D),其是方法(A)、(B)、(B’)、(B”)或(C),其中在步骤(i)中,反应在至少一种烃中进行,所述烃选自由石蜡油、己烷和二甲苯组成的组。
本发明还涉及方法(E),其是方法(A)、(B)、(B’)、(B”)、(C)或(D),其中在步骤(i)中,反应在50-200℃的温度下进行。
本发明还涉及方法(F),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)或(E),其中在步骤(i)中,反应在常压下进行。
本发明还涉及方法(G),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)或(F),其中在步骤(ii)中,使用纯净的H2-气体或包含H2的气体混合物。
本发明还涉及方法(H),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)、(F)或(G),其中在步骤(ii)中,氢化在1.5-40bar、更优选地2-30bar的压强下进行。
本发明还涉及方法(I),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)、(F)、(G)或(H),其中步骤(ii)在镍催化剂存在下进行。
本发明还涉及方法(J),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)、(F)、(G)、(H)或(I),其中步骤(ii)在非均相镍催化剂存在下进行。
本发明还涉及方法(K),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)、(F)、(G)、(H)、(I)或(J),其中不使用任何溶剂来进行步骤(ii)。
本发明还涉及方法(L),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)、(F)、(G)、(H)、(I)或(J),其中步骤(ii)在溶剂或溶剂混合物中进行。
本发明还涉及方法(M),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)、(F)、(G)、(H)、(I)、(J)或(L),其中步骤(ii)在至少一种溶剂中进行,所述溶剂选自由直链的、支化的或环状的具有5-10个碳原子的脂族烃、具有5-10个碳原子的芳族烃、酯、醚、醇组成的组。
本发明还涉及方法(N),其是方法(A)、(B)、(B’)、(B”)、(C)、(D)、(E)、(F)、(G)、(H)、(I)、(J)、(L)或(M),其中步骤(ii)在至少一种溶剂中进行,所述溶剂选自由THF、正己烷、正庚烷、2-丙醇、甲苯和乙酸乙酯组成的组。
此外,本发明还涉及式(I)的化合物在香味和/或香料应用中的用途。
此外,本发明还涉及式(II)的化合物在香味和/或香料应用中的用途。
下列实施例有助于阐释本发明。除非另有说明,所有部分均关于重量给出且温度以℃给出。
实施例
实施例1-制备3,7-二甲基壬-2,6-二烯醛
将乙基-脱氢芳樟醇(3,7-二甲基壬-6-烯基-1-炔基-3-醇,27.4g)、硬脂酸(465mg)、三苯基硅醇(5.87g)、三-(三苯基硅氧烷基)-氧化钒(2.95g)和石蜡油(163g)放置在350ml四颈烧瓶中。在轻微的氩溢出下,利用油浴(温度为145℃)加热混合物。达到~138℃的内部温度并搅拌反应混合物总计5小时。将反应混合物冷却至~70℃的TI并将蒸馏设备安装在反应烧瓶上。在0.05-0.08mbar、最高59℃的头温度下蒸馏包含未转化的乙基-脱氢芳樟醇的产物。约1小时之后,蒸馏完成。通过GC利用内标(十六烷)分析产物。
分离清澈的淡黄色油(28.1g)。
GC分析显示出0.96w%的未转化的乙基-脱氢芳樟醇和88.9w%的四种乙基-柠檬醛异构体。转化率为99.0%,产率为92.2%。
实施例2a-制备3,7-二甲基壬-1-醇
将镍催化剂(Johnson Matthey A4000,250mg)加入到配备有气体夹带搅拌器的100ml反应器中。用3×无水乙醇和2×庚烷洗涤催化剂。加入3,7-二甲基壬-2,6-二烯醛(5.0g)和庚烷(40g)并密封高压釜。反应器用氮气净化5次并用氢气净化5次。将反应器加热至80℃,然后利用氢气增压至20bar。搅拌反应混合物20小时。在反应结束时,将反应器冷却至室温,释放压力并用氮气净化一次。过滤反应混合物并通过GC分析转化率和选择性。产率:5.0g无色油,转化率>99%,产物98.5%。
1H NMR:3.77-3.61(2H,m),1.70-1.48(2H,m),1.47-1.00,11H,m)和0.94-0.81(9h,m)
质谱:154(M-H2O),139,125,97,83,70,55,41,29
IR(cm-1):3324(br),2957,2925,2872,1461,1377
实施例2b-制备3,7-二甲基壬-1-醇
以与实施例2a相似的方式,使3,7-二甲基壬-2,6-二烯醛(5.0g)、乙酸乙酯(40g)和镍催化剂(Johnson Matthey A4000,250mg)在80℃、20bar氢气下反应20小时。产率:5.00g无色油,转化率>99%,产物为98.9%。
实施例3-制备3,7-二甲基壬-1-醇,无溶剂
将镍催化剂(1g)加入到配备有气体夹带搅拌器的100ml反应器中。用无水乙醇和乙酸乙酯洗涤催化剂。加入E-柠檬醛(3,7-二甲基壬-2,6-二烯醛,40g)并密封高压釜。反应器用氮气净化5次并用氢气净化5次。将反应器加热至80℃,然后利用氢气增压至20bar。搅拌反应混合物30小时。在反应结束时,将反应器冷却至室温,释放压力并用氮气净化一次。过滤反应混合物并通过GC分析转化率和选择性。产率:39.29g无色油,转化率>99%,产物98.6%。
Claims (9)
1.生产式(I)的化合物的方法,
其特征在于:在第一步骤(i)中,
使式(II)的化合物
经受重排反应,其中获得式(III)的化合物
且在第二步骤(ii)中,
通过使用金属催化剂来将式(III)的化合物还原为式(I)的化合物,
其中在步骤(i)中使用式(IV)的催化剂
其中,R1、R2和R3彼此独立地为Si(R4)3,其中每个R4彼此独立地为直链的或支化的C1-C10-烷基基团或者被取代的或未被取代的苯基;
其中不使用任何溶剂来进行步骤(ii),或者步骤(ii)在溶剂或溶剂混合物中进行,所述溶剂选自由酯和直链的具有5-10个碳原子的脂族烃组成的组。
2.根据权利要求1的方法,其中在步骤(i)中使用式(IV’)的催化剂。
3.根据权利要求1或2的方法,其中在步骤(i)中,反应在作为溶剂的至少一种烃中进行。
4.根据权利要求1或2的方法,其中在步骤(i)中,反应在50-200℃的温度下进行。
5.根据权利要求1或2的方法,其中在步骤(i)中,反应在常压下进行。
6.根据权利要求1或2的方法,其中在步骤(ii)中,使用纯净的H2-气体或包含H2的气体混合物。
7.根据权利要求1或2的方法,其中在步骤(ii)中,氢化在1.5-40bar的压强下进行。
8.根据权利要求1或2的方法,其中在步骤(ii)中,氢化在2-30bar的压强下进行。
9.根据权利要求1或2的方法,其中步骤(ii)在镍催化剂存在下进行。
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JPS595566B2 (ja) * | 1974-10-18 | 1984-02-06 | 株式会社クラレ | フホウワカルボニルカゴウブツノ セイゾウホウ |
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JPH02167239A (ja) * | 1988-09-28 | 1990-06-27 | Nitto Denko Corp | 3,7−ジメチルノナノールの製造方法及びその前駆中間体 |
US6198006B1 (en) * | 1998-03-30 | 2001-03-06 | Roche Vitamins Inc. | Process for the manufacture of citral |
DE10160142A1 (de) * | 2001-12-07 | 2003-06-18 | Basf Ag | Verfahren zur Herstellung von Tetrahydrogeraniol |
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