CA1178893A - Nitriles aliphatiques - Google Patents

Nitriles aliphatiques

Info

Publication number: CA1178893A
Authority: CA; Canada
Prior art keywords: nitriles; nitrile; methyl; perfume; floral
Prior art date: 1981-09-03
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.): Expired

Application number

CA000452016A

Other languages

English (en)

Inventor

Charles S. Sell

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.)

Givaudan Nederland Services BV

Original Assignee

Unilever PLC

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.)

1981-09-03

Filing date

1984-04-13

Publication date

1984-12-04

1982-08-30 Priority claimed from CA000410404A external-priority patent/CA1174694A/fr

1984-04-13 Application filed by Unilever PLC filed Critical Unilever PLC

1984-04-13 Priority to CA000452016A priority Critical patent/CA1178893A/fr

1984-12-04 Application granted granted Critical

1984-12-04 Publication of CA1178893A publication Critical patent/CA1178893A/fr

Status Expired legal-status Critical Current

Links

-1 Aliphatic nitriles Chemical class 0.000 title abstract description 7
239000000203 mixture Substances 0.000 claims abstract description 18
239000002304 perfume Substances 0.000 claims abstract description 17
150000002825 nitriles Chemical class 0.000 claims description 23
229920006395 saturated elastomer Polymers 0.000 abstract description 2
238000000034 method Methods 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000002904 solvent Substances 0.000 description 5
ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 4
ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 4
VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
241000207199 Citrus Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
235000010254 Jasminum officinale Nutrition 0.000 description 3
240000005385 Jasminum sambac Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
KYWIYKKSMDLRDC-UHFFFAOYSA-N methyl n-nonyl ketone Natural products CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 3
239000000344 soap Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Chemical compound CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
244000297179 Syringa vulgaris Species 0.000 description 2
235000004338 Syringa vulgaris Nutrition 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000020971 citrus fruits Nutrition 0.000 description 2
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 2
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
BGCIAWBDYRWKEK-UHFFFAOYSA-N (1-butylcyclohexyl) acetate Chemical group CCCCC1(OC(C)=O)CCCCC1 BGCIAWBDYRWKEK-UHFFFAOYSA-N 0.000 description 1
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
XPCSGXMQGQGBKU-UHFFFAOYSA-N 2-methyldecanenitrile Chemical compound CCCCCCCCC(C)C#N XPCSGXMQGQGBKU-UHFFFAOYSA-N 0.000 description 1
ADJWCDXUXUVWNV-UHFFFAOYSA-N 2-methyldodecanenitrile Chemical compound CCCCCCCCCCC(C)C#N ADJWCDXUXUVWNV-UHFFFAOYSA-N 0.000 description 1
YZBWLYWBKFUJNQ-UHFFFAOYSA-N 2-methylnonanenitrile Chemical compound CCCCCCCC(C)C#N YZBWLYWBKFUJNQ-UHFFFAOYSA-N 0.000 description 1
KOVZMYUXIJOHCD-UHFFFAOYSA-N 2-methyloctanenitrile Chemical compound CCCCCCC(C)C#N KOVZMYUXIJOHCD-UHFFFAOYSA-N 0.000 description 1
MIKYASNSDCJESJ-UHFFFAOYSA-N 3-methyldecanenitrile Chemical compound CCCCCCCC(C)CC#N MIKYASNSDCJESJ-UHFFFAOYSA-N 0.000 description 1
ZKCZXPOYIUVRIV-UHFFFAOYSA-N 3-methyldodecanenitrile Chemical compound CCCCCCCCCC(C)CC#N ZKCZXPOYIUVRIV-UHFFFAOYSA-N 0.000 description 1
FKZSSFLBNYYIDS-UHFFFAOYSA-N 3-methylnonanenitrile Chemical compound CCCCCCC(C)CC#N FKZSSFLBNYYIDS-UHFFFAOYSA-N 0.000 description 1
BEEDZKVDQYSTPC-UHFFFAOYSA-N 3-methyloctanenitrile Chemical compound CCCCCC(C)CC#N BEEDZKVDQYSTPC-UHFFFAOYSA-N 0.000 description 1
YBGLYNKRMUZVLM-UHFFFAOYSA-N 3-methylundecanenitrile Chemical compound CCCCCCCCC(C)CC#N YBGLYNKRMUZVLM-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
244000144730 Amygdalus persica Species 0.000 description 1
240000007087 Apium graveolens Species 0.000 description 1
235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
235000010591 Appio Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000006040 Prunus persica var persica Nutrition 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
230000003190 augmentative effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
229960000956 coumarin Drugs 0.000 description 1
235000001671 coumarin Nutrition 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008266 hair spray Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940116411 terpineol Drugs 0.000 description 1
CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1

Landscapes

Fats And Perfumes (AREA)

CA000452016A 1981-09-03 1984-04-13 Nitriles aliphatiques Expired CA1178893A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000452016A CA1178893A (fr)	1981-09-03	1984-04-13	Nitriles aliphatiques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB8126748		1981-09-03
GB8126748		1981-09-03
CA000410404A CA1174694A (fr)	1981-09-03	1982-08-30	Nitriles aliphatiques
CA000452016A CA1178893A (fr)	1981-09-03	1984-04-13	Nitriles aliphatiques

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000410404A Division CA1174694A (fr)	1981-09-03	1982-08-30	Nitriles aliphatiques

Publications (1)

Publication Number	Publication Date
CA1178893A true CA1178893A (fr)	1984-12-04

Family

ID=27167279

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000452016A Expired CA1178893A (fr)	1981-09-03	1984-04-13	Nitriles aliphatiques

Country Status (1)

Country	Link
CA (1)	CA1178893A (fr)

1984
- 1984-04-13 CA CA000452016A patent/CA1178893A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-12-05	MKEC	Expiry (correction)
2002-08-30	MKEX	Expiry

Publication	Publication Date	Title
JPS6055484B2 (ja)	1985-12-05	オクタヒドロ−テトウメチルアセトナフトンの有効な芳香量を必須成分として含有している香料組成物
US3296080A (en)	1967-01-03	Linalool homologues
US3716498A (en)	1973-02-13	Novel fragrance compositions
US3669908A (en)	1972-06-13	Alkadienyl pyridines and pyrazines as perfumes
CA1174694A (fr)	1984-09-18	Nitriles aliphatiques
EP0694605B1 (fr)	1999-10-13	Diester cyclique et son utilisation à titre d'ingrédient parfumant
US4338458A (en)	1982-07-06	Cyclopentane derivatives useful as perfuming agents
US4208297A (en)	1980-06-17	Use of novel oxyhydrocarbylnorbornane derivatives for augmenting or enhancing the aroma of detergents
EP0016650A2 (fr)	1980-10-01	2-Cyclopentyl-cyclopentanone, compositions parfumantes ou aromatiques la contenant et leur utilisation
CA1178893A (fr)	1984-12-04	Nitriles aliphatiques
US4341666A (en)	1982-07-27	Perfuming with oxygen containing derivatives of tricyclo[6.2.1.02,7 ]un
US3996169A (en)	1976-12-07	Perfume uses of tricyclic alcohols and processes
US4081481A (en)	1978-03-28	1-Butanoyl-3,3-dimethylcyclohexane
US5358930A (en)	1994-10-25	2-ethoxy-4-formyl phenyl ester of propionic acid and use in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles
US4147727A (en)	1979-04-03	1-Butenoyl-3,3-dimethylcyclohexane mixtures
US4223168A (en)	1980-09-16	Method for preparing oxyhydrocarbylnorbornane derivatives
EP2168940A9 (fr)	2010-06-09	6,8,10-undécatrién-(3 ou 4)-one et composition de parfum
JPH04266865A (ja)	1992-09-22	３−（ヘキセニルオキシ）−プロパン−ニトリル、その製造方法及び香料或いは香料組成物
US4601851A (en)	1986-07-22	Cyclododec-2-enyl ethers in fragrance compositions
JP4138403B2 (ja)	2008-08-27	香料成分としての第三アルコールまたはエステルの使用
US4040987A (en)	1977-08-09	2-Alkyl-substituted-4,5-dimethyl thiazoline perfume and cologne compositions
US6410504B1 (en)	2002-06-25	Nitriles and aldehydes derived from 3-isopropenyl-1,2-dimethyl-1-cyclopentanol and their use in perfumery
US6008186A (en)	1999-12-28	Perfuming ingredients of woody, fruity odor
JPH023440B2 (fr)	1990-01-23
US4392993A (en)	1983-07-12	Alicyclic unsaturated compounds, their preparation and use of same as perfume ingredients