DE2343055A1 - Ungesaettigte nitrile - Google Patents
Ungesaettigte nitrileInfo
- Publication number
- DE2343055A1 DE2343055A1 DE19732343055 DE2343055A DE2343055A1 DE 2343055 A1 DE2343055 A1 DE 2343055A1 DE 19732343055 DE19732343055 DE 19732343055 DE 2343055 A DE2343055 A DE 2343055A DE 2343055 A1 DE2343055 A1 DE 2343055A1
- Authority
- DE
- Germany
- Prior art keywords
- nitrile
- trimethyl
- diene
- acid
- dodeca
- Prior art date
- 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- Withdrawn
Links
- 150000002825 nitriles Chemical class 0.000 title claims description 12
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 20
- -1 3,5,6-trimethyl-hepta-2,6-diene-nitrile Chemical compound 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003205 fragrance Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VBCIOOKAKHGVMI-UHFFFAOYSA-N 5-methylhex-5-en-2-one Chemical compound CC(=C)CCC(C)=O VBCIOOKAKHGVMI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BDMMRMHHMFKXRU-UHFFFAOYSA-N 4,5-dimethylhex-5-en-2-one Chemical compound CC(=C)C(C)CC(C)=O BDMMRMHHMFKXRU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- NOPLRNXKHZRXHT-YFVJMOTDSA-N beta-Sinensal Chemical compound O=CC(/C)=C/CCC(/C)=C/CCC(=C)C=C NOPLRNXKHZRXHT-YFVJMOTDSA-N 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229930014550 juvenile hormone Natural products 0.000 description 3
- 239000002949 juvenile hormone Substances 0.000 description 3
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 3
- 229930000308 sinensal Natural products 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 2
- ZDZHCIAFSISUHF-UHFFFAOYSA-N 6,10-dimethylundeca-5,10-dien-2-one Chemical compound CC(=C)CCCC(C)=CCCC(C)=O ZDZHCIAFSISUHF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229940043350 citral Drugs 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- SAFQZYRQIXIKDC-UHFFFAOYSA-N cyanomethylphosphonic acid Chemical class OP(O)(=O)CC#N SAFQZYRQIXIKDC-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 2
- 230000003054 hormonal effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- FDLVUUYKEFYJRU-YFHOEESVSA-N (2z)-3,7-dimethylocta-2,7-dienenitrile Chemical compound CC(=C)CCC\C(C)=C/C#N FDLVUUYKEFYJRU-YFHOEESVSA-N 0.000 description 1
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- FDFMOQYYMCVWEM-UHFFFAOYSA-N 2-cyanoethylphosphonic acid Chemical class OP(O)(=O)CCC#N FDFMOQYYMCVWEM-UHFFFAOYSA-N 0.000 description 1
- RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 1
- JAZNOVSTPNIFLR-UHFFFAOYSA-N 3,6-dimethylhept-6-en-2-one Chemical compound CC(=O)C(C)CCC(C)=C JAZNOVSTPNIFLR-UHFFFAOYSA-N 0.000 description 1
- FDLVUUYKEFYJRU-UHFFFAOYSA-N 3,7-dimethylocta-2,7-dienenitrile Chemical compound CC(=C)CCCC(C)=CC#N FDLVUUYKEFYJRU-UHFFFAOYSA-N 0.000 description 1
- NMOORMMUOSKTJJ-UHFFFAOYSA-N 3-ethyl-2-methylhex-1-ene Chemical compound CCCC(CC)C(C)=C NMOORMMUOSKTJJ-UHFFFAOYSA-N 0.000 description 1
- BDUFMAYMJLDPIH-UHFFFAOYSA-N 5,6-dimethylhept-6-en-2-one Chemical compound CC(=C)C(C)CCC(C)=O BDUFMAYMJLDPIH-UHFFFAOYSA-N 0.000 description 1
- FMCHGBFGIKQNCT-UHFFFAOYSA-N 6-methylhept-6-en-2-one Chemical compound CC(=C)CCCC(C)=O FMCHGBFGIKQNCT-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
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YMGXCWPUDLRMJZ-UHFFFAOYSA-N octa-2,7-dienenitrile Chemical compound C=CCCCC=CC#N YMGXCWPUDLRMJZ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732343055 DE2343055A1 (de) | 1973-08-25 | 1973-08-25 | Ungesaettigte nitrile |
| CH1142274A CH594611A5 (enrdf_load_stackoverflow) | 1973-08-25 | 1974-08-21 | |
| CH1142174A CH595329A5 (enrdf_load_stackoverflow) | 1973-08-25 | 1974-08-21 | |
| FR7429022A FR2241538B1 (enrdf_load_stackoverflow) | 1973-08-25 | 1974-08-23 | |
| GB3705374A GB1475163A (en) | 1973-08-25 | 1974-08-23 | Unsaturated nitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732343055 DE2343055A1 (de) | 1973-08-25 | 1973-08-25 | Ungesaettigte nitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2343055A1 true DE2343055A1 (de) | 1975-03-06 |
Family
ID=5890759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732343055 Withdrawn DE2343055A1 (de) | 1973-08-25 | 1973-08-25 | Ungesaettigte nitrile |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH595329A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2343055A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2241538B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1475163A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1534132A (en) * | 1975-12-11 | 1978-11-29 | Polak Frutal Works | Alpha beta-disubstituted conjugated nitriles for perfume use |
| FR2500447A1 (fr) * | 1981-02-24 | 1982-08-27 | Schmoller Bompard | Nitriles aliphatiques insatures utilisables en parfumerie et leur procede de preparation |
| US4497827A (en) * | 1982-08-30 | 1985-02-05 | Syntex (U.S.A.) Inc. | Arachidonic acid analogues as anti-inflammatory and anti-allergic agents |
-
1973
- 1973-08-25 DE DE19732343055 patent/DE2343055A1/de not_active Withdrawn
-
1974
- 1974-08-21 CH CH1142174A patent/CH595329A5/xx not_active IP Right Cessation
- 1974-08-21 CH CH1142274A patent/CH594611A5/xx not_active IP Right Cessation
- 1974-08-23 GB GB3705374A patent/GB1475163A/en not_active Expired
- 1974-08-23 FR FR7429022A patent/FR2241538B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2241538A1 (enrdf_load_stackoverflow) | 1975-03-21 |
| FR2241538B1 (enrdf_load_stackoverflow) | 1977-11-04 |
| GB1475163A (en) | 1977-06-01 |
| CH595329A5 (enrdf_load_stackoverflow) | 1978-02-15 |
| CH594611A5 (enrdf_load_stackoverflow) | 1978-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |