EP0039032A2 - Utilisation d'amides de l'acide 3,5,5-triméthylhexanoique comme agents parfumants et compositions parfumées les contenant - Google Patents

Utilisation d'amides de l'acide 3,5,5-triméthylhexanoique comme agents parfumants et compositions parfumées les contenant Download PDF

Info

Publication number: EP0039032A2
Authority: EP; European Patent Office
Prior art keywords: trimethylhexanoic acid; acid amides; perfuming agents; compositions containing; trimethylhexanoic
Prior art date: 1980-04-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP81102990A

Other languages

German (de)

English (en)

Other versions

EP0039032A3 (fr

Inventor

Hinrich Dr. Möller

Ulf Armin Dr. Schaper

Klaus Dr. Bruns

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-04-28

Filing date

1981-04-18

Publication date

1981-11-04

1981-04-18 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

1981-11-04 Publication of EP0039032A2 publication Critical patent/EP0039032A2/fr

1982-09-15 Publication of EP0039032A3 publication Critical patent/EP0039032A3/fr

Status Withdrawn legal-status Critical Current

Links

SBSCDYTYNSHRIX-UHFFFAOYSA-N 3,5,5-trimethylhexanamide Chemical class NC(=O)CC(C)CC(C)(C)C SBSCDYTYNSHRIX-UHFFFAOYSA-N 0.000 title claims abstract description 13
239000000203 mixture Substances 0.000 title claims abstract description 11
239000002304 perfume Substances 0.000 title abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
239000003205 fragrance Substances 0.000 claims description 10
DPBOCZZMRUVIDT-UHFFFAOYSA-N n,n,3,5,5-pentamethylhexanamide Chemical compound CC(C)(C)CC(C)CC(=O)N(C)C DPBOCZZMRUVIDT-UHFFFAOYSA-N 0.000 claims description 4
CCLQXUKDUFZQCC-UHFFFAOYSA-N n,n-diethyl-3,5,5-trimethylhexanamide Chemical compound CCN(CC)C(=O)CC(C)CC(C)(C)C CCLQXUKDUFZQCC-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
GEKPNPPFAYJZRD-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl chloride Chemical compound ClC(=O)CC(C)CC(C)(C)C GEKPNPPFAYJZRD-UHFFFAOYSA-N 0.000 description 2
XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
235000016623 Fragaria vesca Nutrition 0.000 description 2
235000011363 Fragaria x ananassa Nutrition 0.000 description 2
235000011034 Rubus glaucus Nutrition 0.000 description 2
244000235659 Rubus idaeus Species 0.000 description 2
235000009122 Rubus idaeus Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
244000307700 Fragaria vesca Species 0.000 description 1
240000009088 Fragaria x ananassa Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012459 cleaning agent Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

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
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom

Definitions

3,5,5-trimethylhexanoic acid amides have the general formula in which R 1 and R 2 independently of one another stand for hydrogen, a .Lower alkyl radical having 1 to 6 carbon atoms or together with the nitrogen atom for a heterocyclic ring, can advantageously be used as fragrances with a fruity or floral odor note.
the 3,5,5-trimethylhexanoic acid amides to be used according to the invention are prepared by customary organic chemistry methods by reacting the 3,5,5-trimethylhexanoic acid chloride or the lower esters of 3,5,5-trimethylhexanoic acid with the corresponding amines.
the 3,5,5-trimethylhexanoic acid used as starting material is obtained by hydroformylation of diisobutylene with subsequent oxidation of the intermediate product obtained.
the mixture of the acids produced in this way is a commercial product under the name "isononanoic acid" and generally contains about 90% of 3,5,5-trimethylhexanoic acid.
3,5,5-Trimethylhexanoic acid amides to be used according to the invention include, for example, 3,5,5-trimethylhexanoic acid amide, -methylamide, -dimethylamide, -methylethylamide, -diethylamide, -dipropylamide, -pyrolidide, -piperidide.
3,5,5-trimethylhexanoic acid amides to be used according to the invention are valuable fragrances with characteristic fruity fragrance notes. A great advantage is their very good ability to combine with fine fruity odor nuances. 3,5,5-Trimethylhexanoic acid dimethylamide is of particular importance here.
the 3,5,5-trimethylhexanoic acid amides to be used according to the invention can be mixed with other fragrances in a wide variety of proportions to give new fragrance compositions.
the proportion of the 3,5,5-trimethylhexanoic acid amides to be used according to the invention in the fragrance compositions will range from 1 to 50 percent by weight, based on the overall composition.
Such compositions can be used directly as perfume or also for perfuming cosmetics such as creams, lotions, fragrant waters, aerosols, toilet soaps, etc. However, they can also be used to improve the smell of technical products such as washing and cleaning agents, disinfectants, textile treatment agents, etc.
the preparation was carried out in accordance with the above information using diethylamine as the starting material.
the 3,5,5-trimethylhexanoic acid diethylamide obtained has a boiling point of 68 ° C. at 0 , 0 8 mbar and a refractive index 1.4499.
Smell Raspberry note.

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)
Cosmetics (AREA)

EP81102990A 1980-04-28 1981-04-18 Utilisation d'amides de l'acide 3,5,5-triméthylhexanoique comme agents parfumants et compositions parfumées les contenant Withdrawn EP0039032A3 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3016288		1980-04-28
DE19803016288 DE3016288A1 (de)	1980-04-28	1980-04-28	Verwendung von 3,5,5,-trimethylhexansaeureamiden als richstoffe sowie diese enthaltende richstoffkompositionen

Publications (2)

Publication Number	Publication Date
EP0039032A2 true EP0039032A2 (fr)	1981-11-04
EP0039032A3 EP0039032A3 (fr)	1982-09-15

Family

ID=6101133

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP81102990A Withdrawn EP0039032A3 (fr)	1980-04-28	1981-04-18	Utilisation d'amides de l'acide 3,5,5-triméthylhexanoique comme agents parfumants et compositions parfumées les contenant

Country Status (4)

Country	Link
EP (1)	EP0039032A3 (fr)
JP (1)	JPS56169661A (fr)
BR (1)	BR8102535A (fr)
DE (1)	DE3016288A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5143900A (en) *	1989-05-19	1992-09-01	Colgate-Palmolive Company	Perfumes containing N-lower alkyl neoalkanamide (s)
WO2016156075A1 (fr) *	2015-03-31	2016-10-06	Basf Se	Composition comprenant un pesticide et du n,n-diméthyl amide d'acide isononanoïque

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1572332A (fr) *	1968-04-05	1969-06-27
DE2757559C2 (de) *	1977-12-23	1986-10-30	Henkel KGaA, 4000 Düsseldorf	Verwendung der 3,5,5-Trimethylhexansäureester als Riechstoffe sowie diese enthaltende Riechstoffkompositionen
FR2452921A1 (fr) *	1979-04-02	1980-10-31	Rhone Poulenc Ind	Procede d'obtention de compositions parfumantes et de produits parfumes et compositions et produits ainsi obtenus

1980
- 1980-04-28 DE DE19803016288 patent/DE3016288A1/de not_active Withdrawn
1981
- 1981-04-18 EP EP81102990A patent/EP0039032A3/fr not_active Withdrawn
- 1981-04-27 BR BR8102535A patent/BR8102535A/pt unknown
- 1981-04-28 JP JP6511381A patent/JPS56169661A/ja active Pending

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5143900A (en) *	1989-05-19	1992-09-01	Colgate-Palmolive Company	Perfumes containing N-lower alkyl neoalkanamide (s)
WO2016156075A1 (fr) *	2015-03-31	2016-10-06	Basf Se	Composition comprenant un pesticide et du n,n-diméthyl amide d'acide isononanoïque
US10463040B2 (en)	2015-03-31	2019-11-05	Basf Se	Composition comprising a pesticide and isononanoic acid N,N-dimethyl amide
AU2016239537B2 (en) *	2015-03-31	2020-02-06	Basf Se	Composition comprising a pesticide and isononanoic acid N,N-dimethyl amide
RU2723035C2 (ru) *	2015-03-31	2020-06-08	Басф Се	Композиция, содержащая пестицид и n,n-диметиламид изононановой кислоты

Also Published As

Publication number	Publication date
DE3016288A1 (de)	1981-11-12
EP0039032A3 (fr)	1982-09-15
JPS56169661A (en)	1981-12-26
BR8102535A (pt)	1982-01-05

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Legal Events

Date	Code	Title	Description
1981-09-04	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1981-11-04	AK	Designated contracting states	Designated state(s): CH DE FR GB IT NL
1982-07-12	PUAL	Search report despatched	Free format text: ORIGINAL CODE: 0009013
1982-09-15	AK	Designated contracting states	Designated state(s): CH DE FR GB IT NL
1983-04-20	17P	Request for examination filed	Effective date: 19830204
1984-03-26	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN
1984-05-30	18D	Application deemed to be withdrawn	Effective date: 19831201
2007-08-08	RIN1	Information on inventor provided before grant (corrected)	Inventor name: BRUNS, KLAUS, DR. Inventor name: SCHAPER, ULF ARMIN, DR. Inventor name: MOELLER, HINRICH, DR.