CH629739A5 - Process for the preparation of 4,8-dimethylnonan-8-ol-1-al - Google Patents
Process for the preparation of 4,8-dimethylnonan-8-ol-1-al Download PDFInfo
- Publication number
- CH629739A5 CH629739A5 CH208677A CH208677A CH629739A5 CH 629739 A5 CH629739 A5 CH 629739A5 CH 208677 A CH208677 A CH 208677A CH 208677 A CH208677 A CH 208677A CH 629739 A5 CH629739 A5 CH 629739A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethylnonan
- rhodium
- catalyst
- compound
- formula
- Prior art date
Links
Classifications
-
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von 4,8-Dimethylnonan-8-ol-l-al, das dadurch gekennzeichnet ist, dass man 3,7-Dimethyloct-l-en-7-ol mit Wasserstoff und Kohlenmonoxid in Gegenwart einer Rhodium- oder Kobaltverbindung als Katalysator umsetzt. The invention relates to a process for the preparation of 4,8-dimethylnonan-8-ol-l-al, which is characterized in that 3,7-dimethyloct-l-en-7-ol with hydrogen and carbon monoxide in the presence of a rhodium - or reacting cobalt as a catalyst.
Als Katalysator im erfindungsgemässen Verfahren bevorzugt ist ein Rhodium- oder Kobaltcarbonylderivat, insbesondere ein Rhodiumcarbonylderivat, das ausser einer oder mehreren Carbonylgruppen eine Hydridgruppe und/ oder einen oder mehrere Phosphor enthaltende Liganden enthält. Der Katalysator kann homogen sein, wie die Verbindungen der Formeln HRh(CO)(P(C6H5)3)3 oder C02(C0)s, oder heterogen, z.B. eine dieser Verbindungen auf einem festen Träger, wie Kieselgel, enthalten. Preferred as the catalyst in the process according to the invention is a rhodium or cobalt carbonyl derivative, in particular a rhodium carbonyl derivative, which, in addition to one or more carbonyl groups, contains a hydride group and / or one or more phosphorus-containing ligands. The catalyst may be homogeneous, such as the compounds of the formulas HRh (CO) (P (C6H5) 3) 3 or CO 2 (CO), or heterogeneous, e.g. contain one of these compounds on a solid support, such as silica gel.
Die erfindungsgemässe Hydroformylierung erfolgt vorzugsweise bei einer Temperatur von 50 bis 200 °C und bei einem Druck von vorzugsweise bis zu 150 bar. Man kann das Verfahren auch in einem organischen Lösungsmittel durchführen, z.B. in einem aromatischen Kohlenwasserstoff, wie Benzol. The hydroformylation according to the invention is preferably carried out at a temperature of 50 to 200 ° C. and at a pressure of preferably up to 150 bar. The process can also be carried out in an organic solvent, e.g. in an aromatic hydrocarbon such as benzene.
Die Verbindung der Formel I hat einen frischen blumigen Geruch mit einem maiglöckchenähnlichen Duft. In gewissen Beziehungen ähnelt die erfindungsgemässe Verbindung dem bekannten homologen Hydroxy-citronellal (3,7-Dimethyloctan-7-ol-l-al), sie ist jedoch milder und hat nicht die Schärfe von Hydroxy-citronellal. Der Duft der erfindungsgemässen Verbindung verbreitet sich leichter und hält länger an als der von Hydroxy-citronellal. The compound of formula I has a fresh floral smell with a lily of the valley fragrance. In certain respects, the compound according to the invention is similar to the known homologous hydroxy-citronellal (3,7-dimethyloctan-7-ol-l-al), but it is milder and does not have the sharpness of hydroxy-citronellal. The scent of the compound according to the invention spreads more easily and lasts longer than that of hydroxy-citronellal.
Es ist in der Parfümerie allgemein bekannt, dass man aus einer chemischen Beziehung zwischen zwei Verbindungen, wie der erfindungsgemässen Verbindung und ihrem niedrigeren Homologen Hydroxy-citronellal, keine Aussagen über die Geruchseigenschaften der einen oder anderen Verbindung machen kann. Man würde jedoch annehmen, dass beide Verbindungen in ihren chemischen Eigenschaften gleich sind, z.B. in der Stabilität in verschiedenen Medien. It is generally known in perfumery that a chemical relationship between two compounds, such as the compound according to the invention and its lower homologue hydroxy-citronellal, cannot be used to make any statements about the odor properties of one or the other compound. However, one would assume that both compounds have the same chemical properties, e.g. in stability in different media.
Erstaunlicherweise wurde festgestellt, dass die Verbindung der Formel I stabiler ist, insbesondere in alkalischen Medien, wie Oberflächenreinigungsmittel und Grobwaschmittel, als Hydroxy-citronellal. Surprisingly, it has been found that the compound of the formula I is more stable than hydroxycitronellal, in particular in alkaline media, such as surface cleaning agents and heavy duty detergents.
Diese Verbindung kann als solche als Aromastoff oder in Kombination mit anderen Verbindungen oder Gemischen, z.B. ätherischen Ölen, für parfümierte Produkte verwendet werden. This compound can be used as a flavoring or in combination with other compounds or mixtures, e.g. essential oils, can be used for perfumed products.
Unter «parfümiertes Produkt» ist hier ein Gemisch von Aromastoffen und anderen Hilfsmitteln gemeint, das in einem geeigneten Lösungsmittel gelöst oder gegebenenfalls mit einem geeigneten gepulverten Substrat vermischt und dazu verwendet wird, verschiedenen Produkten den gewünschten Geruch zu verleihen. Beispiele für derartige Produkte sind Seifen, Reinigungsmittel, Waschmittel, Kosmetika und Raumdesodorantien. “Perfumed product” here means a mixture of flavors and other auxiliaries which is dissolved in a suitable solvent or, if appropriate, mixed with a suitable powdered substrate and used to impart the desired odor to various products. Examples of such products are soaps, cleaning agents, detergents, cosmetics and room deodorants.
Die Menge an Verbindung der Formel I in derartigen Produkten hängt von dem gewünschten Geruch ab und kann innerhalb weiter Grenzen schwanken. Bevorzugt sind Mengen von 0,1 Gewichtsprozent oder darüber in konzentrierten parfümierten Produkten, wobei sich diese Menge bei der Verdünnung oder bei der Verwendung in zu parfümierenden Produkten proportional verringert. The amount of compound of formula I in such products depends on the desired smell and can vary within wide limits. Amounts of 0.1 percent by weight or above are preferred in concentrated perfumed products, this amount being reduced proportionally when diluted or when used in products to be perfumed.
Die Beispiele erläutern die Erfindung. The examples illustrate the invention.
Beispiel 1 example 1
18,0 g 3,7-Dimethyloct~l-en-7-ol, 0,20 g Tris-(triphenyl-phospin)-hydridocarbonylrhodium(I) und 20 ml Benzol werden in einen 100 ml fassenden Autoklaven aus rostfreiem Stahl, der mit einem Magnetrührer ausgerüstet ist, eingefüllt. Der Autoklav wird mit einem Gemisch aus gleichen Volumina Wasserstoff und Kohlenmonoxid bis zu einem Druck von 85 bar beaufschlagt und dann 2 Stunden auf 100 °C gehalten. Nach dem Abkühlen auf 20 °C und Druckausgleich wird das Gemisch unter vermindertem Druck fraktioniert destilliert. Man erhält 15,4 g der gewünschten Verbindung mit einem Kp./0,8 mm Hg von 105 bis 106 °C. Dieses Rohprodukt wird durch Drehband-Kolonnen-Destillation gereinigt. 18.0 g of 3,7-dimethyloct ~ l-en-7-ol, 0.20 g of tris (triphenyl-phosphine) hydridocarbonylrhodium (I) and 20 ml of benzene are placed in a 100 ml stainless steel autoclave, the equipped with a magnetic stirrer. A mixture of equal volumes of hydrogen and carbon monoxide is applied to the autoclave up to a pressure of 85 bar and then kept at 100 ° C. for 2 hours. After cooling to 20 ° C and pressure equalization, the mixture is fractionally distilled under reduced pressure. 15.4 g of the desired compound with a boiling point / 0.8 mm Hg of 105 to 106 ° C. are obtained. This crude product is purified by rotating column distillation.
Das NRM-Spektrum des erfindungsgemässen 4,8-Di-methylnonan-8-ol-l-al wird bei 60 MHz in deuteriertem Chloroform gemessen und mit einem Tetramethylsilan-Stan-dard verglichen. The NRM spectrum of the 4,8-dimethylnonan-8-ol-l-al according to the invention is measured at 60 MHz in deuterated chloroform and compared with a tetramethylsilane standard.
8ppm: 9,81 (Triplett, CHO), 2,42 (doppeltes Triplett, 8ppm: 9.81 (triplet, CHO), 2.42 (double triplet,
O O
II II
-CH2-C) 2,08 (Singulett, OH), 1,21 (Singulett, (CH3)2C), 0,88 (ÇH3CH), 1,0 bis 1,7 (9H). -CH2-C) 2.08 (singlet, OH), 1.21 (singlet, (CH3) 2C), 0.88 (ÇH3CH), 1.0 to 1.7 (9H).
Das Produkt hat einen frischen blumigen Geruch mit einem maiglöckchenähnlichen Duft. The product has a fresh floral scent with a lily of the valley fragrance.
Beispiel 2 Example 2
Ein Parfum mit Maiglöckchenduft wird aus den folgenden Bestandteilen hergestellt: A lily of the valley fragrance is made from the following ingredients:
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
Bestandteile Components
Menge amount
(Gewichtsteile) (Parts by weight)
4,8-Dimethylnonan-8-ol-l-al 350 4,8-dimethylnonan-8-ol-l-al 350
Citronellol 200 Citronellol 200
Linalool 100 Linalool 100
Citronellylacetat 30 Citronelly acetate 30
Benzylacetat 20 Benzyl acetate 20
Terpineol 30 Terpineol 30
Linalylacetat 50 Linalyl acetate 50
3-(p-tert.-Butylphenyl)-2 -methylpropanal 20 3- (p-tert-butylphenyl) -2-methylpropanal 20
Phenyläthylalkohol 50 Phenylethyl alcohol 50
a-Hexylcinnamaldehyd 20 a-Hexylcinnamaldehyde 20
3-Phenylpropenol 10 3-phenylpropenol 10
Indol1 20 Indole1 20
a-Ionon1 50 a-Ionon1 50
Parfum12 30 Perfume 12 30
Äthyl-linalyl-acetaldehydacetal13 10 Ethyl-linalyl-acetaldehyde acetal 13 10
cis-Hex-3-en-l-yl-acetat1 10 cis-hex-3-en-l-yl acetate 1 10
lÖÖÖ LÖÖÖ
1 lOprozentige Lösung in Diäthylphthalat 10% solution in diethyl phthalate
2 Parfum der Firma Naarden International N.V. 2 perfumes by Naarden International N.V.
3 GB-PS 1 371 727 3 GB PS 1 371 727
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB686876A GB1554461A (en) | 1976-02-20 | 1976-02-20 | Hydroxy-aldehyde and a perfume composition or product containing said aldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629739A5 true CH629739A5 (en) | 1982-05-14 |
Family
ID=9822245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH208677A CH629739A5 (en) | 1976-02-20 | 1977-02-18 | Process for the preparation of 4,8-dimethylnonan-8-ol-1-al |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6031812B2 (en) |
| CH (1) | CH629739A5 (en) |
| DE (1) | DE2707108C2 (en) |
| FR (1) | FR2341550A1 (en) |
| GB (1) | GB1554461A (en) |
| NL (1) | NL7701674A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5981399A (en) * | 1982-11-02 | 1984-05-11 | 川研ファインケミカル株式会社 | Natural essential oil fragrance modifying method |
-
1976
- 1976-02-20 GB GB686876A patent/GB1554461A/en not_active Expired
-
1977
- 1977-02-17 NL NL7701674A patent/NL7701674A/en not_active Application Discontinuation
- 1977-02-18 JP JP1630077A patent/JPS6031812B2/en not_active Expired
- 1977-02-18 FR FR7704733A patent/FR2341550A1/en active Granted
- 1977-02-18 CH CH208677A patent/CH629739A5/en not_active IP Right Cessation
- 1977-02-18 DE DE19772707108 patent/DE2707108C2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2341550A1 (en) | 1977-09-16 |
| GB1554461A (en) | 1979-10-24 |
| FR2341550B1 (en) | 1978-10-20 |
| JPS52100409A (en) | 1977-08-23 |
| NL7701674A (en) | 1977-08-23 |
| DE2707108A1 (en) | 1977-08-25 |
| DE2707108C2 (en) | 1985-11-14 |
| JPS6031812B2 (en) | 1985-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |