CN1108644A - 1-苯基-1-氰基-c5-c7烷烃及其制造方法和用途 - Google Patents
1-苯基-1-氰基-c5-c7烷烃及其制造方法和用途 Download PDFInfo
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- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
- C11B9/0065—Nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/33—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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Abstract
本发明涉及1-苯基-1-氰基C5-C7烷烃,其结构为上式,R1和R2各别代表氢和甲氧基。如果R1是氢,则R2是甲氧基,反之,R1是甲氧基则R2是氢,X代表C3-C5的烷烃直链或烷烃分枝链。此物品用于增强或修正香水成分、香物品、及刮须香水。并叙述制造此1-苯基-1-氰基C5-C7烷烃的过程中以苯甲基氰与醛或酮作用,以钯为催化剂,然后进行氢化作用而得的产品。
Description
本发明涉及1-苯基-1-氰基-C5-C7烷烃,其结构通式为:
R1和R2各别代表氢和甲氧基。如果R1是氢,则R2是甲氧基,反之,R1是甲氧基则R2是氢,X代表C3-C5的直烷烃链或支链烷烃。此物品用于增强或修正香水成分、香物品、及刮须香水。此新颖的合化物,较佳的结构式如下:
它们是用于加强或增进香水成分,刮须香水及香物品的芳香气。香物品包括但不限于香聚合物,化妆粉,阴离子的、阳离子的、非离子的或两性离子的清洁剂,布料软化剂成分、布料软化剂包括用于烘干机的软化剂。(比如,BOUNCE是由俄亥俄州,辛辛那提市的Procter & Gamble公司出品)。
此化合物的结构通式如下:
以下将涉及本发明的1-苯基-1-氰基-C5-C7烷烃。本发明的1-苯基-1-氰基-C5-C7烷烃,具有赋于、加强或增进花香、玫瑰香、铃兰香、药草香、青草香、水果香、似夙梨香、水杨醛酸酯香、紫苏香、甜香、生橙花香、杏仁香、樱桃香、麝香、香脂香、柏木香、及山艾香偕同甜味、割草香、花香、钤兰香、玫瑰香、水杨酸酯香、茴香脑、香芹酮香、木香等留香,其立时发放的香气为,甜味香、木香、水果香、酒香、割草香、水杨酸酯香、似动物气味、似蜂蜜味、花香、玫瑰香、似松脂香、玫瑰木香。当用于香水成分,刮须香水和其它香物品如肥皂、漂白剂、和任何阴离子的,阳离子的,非离子的,两性离子的清洁剂、布料软化剂等等香物品时,常有清洁的效果。
本发明第一步的制造过程,涉及到以苯甲基氰,其结构式如下:
和如下结构式的醛类或酮类:
互相作用。
此处的R3和R4是相同或不同的氢或低级烷烃,其条件是,
R3和R4不是同时为氢,根据下面的反应式:
所得的产物,其结构式如下:
然后以钯为催化剂,(钯附于碳上)进行氢化作用,其反应式如下:
如此形成的产品,其结构式如下:
定名为本发明的1-苯基-1-氰基-C5-C7烷烃的结构通式如下:
制造本发明的反应式如下:
此反应进行时,温度保持在35°-90℃之间,以酒精基且无水的碱性金属的氢氧化物为催化剂。所用的酒精可以是甲醇或乙醇。碱性氢氧化物金属可以是氢氧化钾或氢氧化钠。(醛或酮)∶(苯甲基氰的衍生物)的摩尔比例,约为0.5∶1至1∶0.5不等,但摩尔比例以1∶1为宜。(碱性氢氧化物金属)∶(酒精)的摩尔比例,约为每公升含40克至每公升含120克不等。
下面的化合物,其结构式如下:
与酒精(甲醇或乙醇)的摩尔比例,约为每公升含二摩尔至每公升含六摩尔不等。反应时间约五至三十小时不等。
进行氢化作用的反应式
反应温度约80°-100℃,压力约300-600psig。催化剂以钯附于碳上,钯的含量约占3%-10%不等,但以占5%为宜。
反应结束后,反应总体经过滤并以蒸馏柱分馏。再引述其反应式如下:
反应到后最时,反应总体加弱酸如醋酸来停止反应,然后用水洗。此反应总体,在进行氢化作用之前,采用蒸馏柱分馏。
以下的表格表明各种成分的不同香性质,其一般结构式如下:
它在香精上用途很广。
表1
本发明的化学物用于下列的柏木香配方:
成分 重量比例
A部分 B部分 C部分
黄葵 40 40 40
麝香酮 60 60 60
香豆素 30 30 30
香柠檬油 150 150 150
柠檬油 100 100 100
甲基紫罗桐 50 50 50
己基肉桂醛 100 100 100
羟基香茅醛 100 100 100
欧薄荷 50 50 50
德州柏木油 85 85 85
维州柏木油 30 30 30
檀香木油(东印度) 40 40 40
丁子香粉 10 10 10
苯乙酸酯 30 30 30
α-苯基-乙醇 40 40 40
β-苯基-乙醇 30 30 30
橡树苔净油 30 30 30
岩兰草油(委内瑞拉) 25 25 25
含结构式如下的化合物:
赋予此柏木香配方以花香、钤兰香、割草香、水杨醛酸酯香、茴香脑香和似香芹酮等留香,并发放出花香、玫瑰香、钤兰香、割草香、水果香、夙梨香、水杨醛酸酯香。根据例子A柏木香配方,可叙述为“是一种柏木芳香物,发散出花香、玫瑰香、钤兰香、割草香、水果香、夙梨香、水杨醛酸酯香并以花香、钤兰香、割草香、水杨醛酸酯香、茴香脑、香芹酮等留香。”
含结构式如下的化合物:
赋予此柏木香配方以木香、甜味香和杏仁味等留香,并发散出杏仁味和樱桃香。根据例子B柏木香配方,可叙述为“是一种柏木芳香物,以木香、甜味香和杏仁味等留香,并发散出杏仁味和樱桃香。”
含结构式如下的化合物:
赋予此柏木香配方以割草香、木香、雪茄烟盒香味、水杨醛酸酯香和龙涎香之留香,并发散出割草香和木香。根据例子C柏木香配方,可叙述为“是一种柏木芳香物,有割草香、木香、似雪茄烟盒香味、水杨醛酸酯香盒龙涎香等留香,并发散出割草香和木香。”
Claims (14)
3、如权利要求1所述的程序中的消费品,其特征在于是一种香料混合物。
4、如权利要求1所述的程序中的消费品,其特征在于是一种香物品,此香物品是一种固态或液态的阴离子的,阳离子的,非离子、两性离子的清洁剂。
5、如权利要求1所述的程序中的消费品,其特征在于是一种香物品,同时也是一种香聚合物。
14、一种制造1-苯基-1-氰基-C5-C7烷烃的方法,其烷烃的结构式如下:
此处的R1和R2各别为氢和甲氧基,其条件为,若中R1为甲氧基,则R2为氢,若是R1为氢,则R2为甲氧基;X代表C3-C5的直链或分枝链烷烃。
其特征包括(1)实际进行的反应式如下:
即将此结构式
的化合物,与结构式:
的化合物,
温度保持在35°-90℃之间,置于酒精而无水之碱性金属的氢氧化物的存在状况下反应,而形成如下的化合物:
此处的R3和R4各别代表低级烷基或氢,附带的条件是R3和R4不能同时为氢,以及
(2)将结构式如下的化合物:
与氢作用时,温度保持在80°-100℃之间,压力保持在300-600psog进行反应。其反应式如下:
(3)将化合物从反应整体中分离出来,此化合物的结构式如下:
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US241,725 | 1994-05-12 | ||
US08/241,725 US5389608A (en) | 1994-05-12 | 1994-05-12 | 1-phenyl-1-cyano-C5 -C7 alkanes, organoleptic uses thereof and process for preparing same |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1108644A true CN1108644A (zh) | 1995-09-20 |
CN1131852C CN1131852C (zh) | 2003-12-24 |
Family
ID=22911919
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN94118425.0A Expired - Lifetime CN1131852C (zh) | 1994-05-12 | 1994-12-16 | 1-苯基-1-氰基-c5-c7烷烃及其用途 |
Country Status (4)
Country | Link |
---|---|
US (1) | US5389608A (zh) |
EP (1) | EP0682010B1 (zh) |
CN (1) | CN1131852C (zh) |
DE (1) | DE69506944T2 (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004528289A (ja) * | 2001-01-26 | 2004-09-16 | クエスト・インターナショナル・ビー・ブイ | 芳香性化合物 |
EP1637581B1 (en) | 2004-09-16 | 2008-07-09 | Firmenich S.A. | Nitrile derivatives as perfuming ingredients |
JP5248114B2 (ja) * | 2004-12-08 | 2013-07-31 | ジボダン エス エー | 有機化合物 |
GB0518558D0 (en) * | 2005-09-12 | 2005-10-19 | Givaudan Sa | Improvements in or related to organic compounds |
US7390772B2 (en) | 2006-05-18 | 2008-06-24 | International Flavor & Fragrances Inc. | 1-phenyl-spiro[2.5]octane-1-carbonitrile analogues their use in fragrance formulations |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2919274A (en) * | 1957-09-17 | 1959-12-29 | Sahyun Melville | Amidines |
NL169613C (nl) * | 1975-02-11 | 1982-08-02 | Naarden International Nv | Werkwijze ter bereiding van reukstofcomposities respectievelijk geparfumeerde produkten en aldus verkregen geparfumeerde voorwerpen. |
RO75279A2 (ro) * | 1976-12-31 | 1980-09-30 | Intreprinderea De Medicamente "Terapia",Ro | Procedeu de preparare a acizilor cicloalchilfenilacetici |
NL8101739A (nl) * | 1981-04-08 | 1982-11-01 | Naarden International Nv | Parfumcomposities en geparfumeerde voorwerpen en materialen, die alkylgesubstitueerde benzylcyaniden als reukstof bevatten. |
DE3139358C2 (de) * | 1981-10-02 | 1984-06-07 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Verwendung von 1,1-Di(C↓1↓-C↓6↓-alkyl)-2-phenyl-ethan-Derivaten als Riechstoffe |
US4985402A (en) * | 1990-04-25 | 1991-01-15 | International Flavors & Fragrances Inc. | 2-Methyl-1-nitrilo-2-methyl -1-hydroxylamino-3-(methoxyphenyl) propane, organoleptic uses thereof and processes for preparing same |
US5177250A (en) * | 1991-05-13 | 1993-01-05 | Ethyl Corporation | Hydrogenation of aromatic-substituted olefins using organoruthenium catalyst |
US5143899A (en) * | 1991-09-13 | 1992-09-01 | International Flavors & Fragrances Inc. | Process for preparing phenyl butyronitriles and perfumery use of 2,2-dimethyl-4-phenyl valeronitrile |
-
1994
- 1994-05-12 US US08/241,725 patent/US5389608A/en not_active Expired - Lifetime
- 1994-12-16 CN CN94118425.0A patent/CN1131852C/zh not_active Expired - Lifetime
-
1995
- 1995-04-28 EP EP95302896A patent/EP0682010B1/en not_active Expired - Lifetime
- 1995-04-28 DE DE69506944T patent/DE69506944T2/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE69506944T2 (de) | 1999-06-17 |
CN1131852C (zh) | 2003-12-24 |
EP0682010A1 (en) | 1995-11-15 |
DE69506944D1 (de) | 1999-02-11 |
EP0682010B1 (en) | 1998-12-30 |
US5389608A (en) | 1995-02-14 |
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