GB2054557A - Novel butanals - Google Patents
Novel butanals Download PDFInfo
- Publication number
- GB2054557A GB2054557A GB8015991A GB8015991A GB2054557A GB 2054557 A GB2054557 A GB 2054557A GB 8015991 A GB8015991 A GB 8015991A GB 8015991 A GB8015991 A GB 8015991A GB 2054557 A GB2054557 A GB 2054557A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butanal
- formaldehyde
- methylcyclohex
- process according
- enyl
- 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.)
- Granted
Links
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims abstract description 13
- YZFPDESEFZSBIN-UHFFFAOYSA-N 3-(4-methylcyclohexyl)butanal Chemical compound O=CCC(C)C1CCC(C)CC1 YZFPDESEFZSBIN-UHFFFAOYSA-N 0.000 claims abstract description 12
- VJYFMQREUJXCQV-UHFFFAOYSA-N Limonene aldehyde Chemical compound O=CCC(C)C1CCC(C)=CC1 VJYFMQREUJXCQV-UHFFFAOYSA-N 0.000 claims abstract description 11
- FFFSOJPRLLQQAA-UHFFFAOYSA-N 3-(4-methylcyclohex-3-en-1-yl)-2-methylidenebutanal Chemical compound O=CC(=C)C(C)C1CCC(C)=CC1 FFFSOJPRLLQQAA-UHFFFAOYSA-N 0.000 claims abstract description 9
- YIAJIVSUDZUUOG-UHFFFAOYSA-N 3-(4-methylcyclohexyl)-2-methylidenebutanal Chemical compound O=CC(=C)C(C)C1CCC(C)CC1 YIAJIVSUDZUUOG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229940087305 limonene Drugs 0.000 claims abstract description 6
- 235000001510 limonene Nutrition 0.000 claims abstract description 6
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- 150000003335 secondary amines Chemical class 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000007037 hydroformylation reaction Methods 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- MZKVNBGZOYBICO-UHFFFAOYSA-N 2-(4-methylcyclohex-3-en-1-yl)butanal Chemical compound CCC(C=O)C1CCC(C)=CC1 MZKVNBGZOYBICO-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- GFAQQAUTKWCQHA-UHFFFAOYSA-N n-propylpentan-1-amine Chemical compound CCCCCNCCC GFAQQAUTKWCQHA-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 8
- -1 Methylene aldehydes Chemical class 0.000 description 7
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000005822 methylenation reaction Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
Abstract
A process for preparing 2 -methylene- 3-(4-methylcyclohex-3-enyl)- butanal or 2-methylene-3-(4-methylcyclohexyl)- butanal comprises reacting 3-(4-methylcyclohex-3-enyl)-butanal or 3-(4-methylcyclohexyl)-butanal with formaldehyde or a formaldehyde- forming compound and in the presence of a catalytic amount of a secondary amine. The 3-(4-methylcyclohex-3-enyl)- butanal or 3-(4-methylcyclohexyl)- butanal may be prepared from limonene. 2-methylene-3-(4-methylcyclohex- 3-enyl)-butanal and 2-methylene-3- (4-methylcyclohexyl)-butanal are fragrant novel compounds.
Description
SPECIFICATION
Novel butanals
The present invention relates to two novel compounds, namely 2-methylene-3-(4-methylcyclohex-3-enyl)-butanal and 2-methylene-3 (4-methylcyclohexyl)-butanal.
Methylene aldehydes can be prepared in various ways.
The Mannich reaction may be used to prepare methylene aldehydes. According to the
Mannich reaction, ammonia or a primary or secondary amine, usually present as a salt e.g. the hydrochloride, is reacted with formaldehyde and a compound containing an active hydrogen atom. According to a process described in US Patent Specification No.
2,518,416 a mixture of an aldehyde having a
CH2 group on the oe-position relative to the carbonyl group and formaldehyde are passed through a melt of a salt of a primary or secondary amine and a strong acid to form a methylene aldehyde. Piperidine hydrochloride, morpholine hydrochloride or an ammonium salt, such as ammonium chloride, have also been used to condense aliphatic aldehydes with formaldehyde (cf. US Patent Specification No. 2,639,295).
In accordance with a new process described in German Patent Application P 28 55 505.7 aldehydes are reacted with formaldehyde in the presence of catalytic amounts of enamines to produce 2-methylenealdehydes. This process is found to be economically advantageous and technically simple to implement as compared with the known methods.
In accordance with a first aspect of the present invention, there is provided a process for preparing 2-methylene-3-(4-methylcyclohex-3-enyl)-butanal or 2-methylene-3-(4-methylcyclohexyl)-butanal, comprising reacting 3 (4-methylcyclohex-3-enyl)-butanal or 3q4-me- thylcyclohexyl)-butanal with formaldehyde or a formaldehyde-forming compound and in the presence of a catalytic amount of a secondary amine.
The reaction of the 3-(4-methylcyclohex-3enyl)-butanal or the 3-(4-methylcyclohexyl)-butanal with the formaldehyde or the formaldehyde-forming compound may be carried out in a known manner.
It will be appreciated that the reaction of the 3-(4-methylcyclohex-3-enyl)-butanal with the formaldehyde or the formaldehyde-forming compound yields 2-methylene-3-(4-methylcyclohex-3-enyl)-butanal whereas the reaction of the 3-(4-methylcyclohexyl)-butanal with the formaldehyde on the formaldehyde-forming compound yields 2-methylene-3-(4-methylcyclohexyl)-butanal.
Limonene (1 -methyl-4-isopropenyl-cyclohex- 1-ene) can easily be converted into 3-(4-methylcyclohex-3-enyl)-butanal by hydroformylation. Hydroformylation, i.e. the addition reaction of olefinically unsaturated compounds with carbon monoxide and hydrogen to form aldehydes, can be effected by various methods which basically differ in the type of catalyst employed. It is known to use as catalysts, cobalt carbonyl compounds containing trialkylphosphines or triaryl-phosphines, in addition to carbon monoxide, as ligands. It is also known to use as catalysts rhodium carbonyl complexes. It has proved particularly suitable to employ as catalysts rhodium carbonyls containing triphenyl-phosphines or trialkyl-phosphines as ligands, and to use pressures of 100 to 350 atmosperes and temperatures of 110 to 1 60 C (cf.German Patent Application p 28 37 480).
In preparing 2-methylene-3-(4-methylcyclohex-3-enyl)-butanal or 2-methylene-3-(4-methylcyclohexyl)-butanal, 3-(4-methylcyclohex3-enyl)-butanal or 3-(4-methylcyclohexyl)-butanal (as the first reactant) and formaldehyde or a formaldehyde-forming compound (as the second reactant) are preferably provided in a molar ratio of 1 mole of the first reactant to 1 mole of formaldehyde constituting or capable of being provided by the second reactant. A slight excess of one of the two reactants is not harmful but is not necessary. The formaldehyde may be used as the pure compound or as a solution in, for example, water. Instead of formaldehyde itself a compound which forms formaldehyde under certain conditions, e.g. a condensation product of formaldehyde, such as paraformaldehyde, can be used as the second reactant.
The catalyst is a secondary amine which may contain the same or different alkyl radicals. Examples are N-ethyl-n-butylamine, Npropyl-n-pentylamine and N-ethyl-cyclohexylamine. Di-n-butylamine has proved particularly suitable. Preferably 0.01 to 0.5 moles of secondary amine, more preferably 0.025 moles are present per mole of formaldehyde (or per mole of formaldehyde capable of being formed by the formaldehyde forming compound). The reaction is preferably carried out at a temperature of 60 to 1 20 C, more preferably 80 to 100"C.
In order to carry out the methylenation, the 3-(4-methylcyclohex-3-enyl)-butanal or the 3 (4-methylcyclohexyl)-butanal is reacted directly with the formaldehyde or the formaldehydeforming compound in the presence of the catalyst. The presence of a solvent such as water or an alcohol (e.g. isobutanol or 2ethylhexanol) is advantageous.
The desired reaction product can be separated by fractional distillation in a form which enables it to be used without further purification.
3-(4-methylcyclohexyl)-butanal can be obtained by partial hydrogenation of 3-(4-methylcyclohex-3-enyl)-butanal. The reaction is generally carried out with hydrogen in a pressurised vessel and in the presence of a cata
Cyst. Depending on the type of catalyst, pressures of 1 to 1 50 atmospheres and temperatures of 20 to 1 20 C are used. A noble metal, e.g. palladium or platinum can be used as the hydrogenation catalyst. Palladium catalysts have proved particularly suitable. The catalyst is conveniently used in a concentration of 0.5 to 2% by weight based on the weight of aldehyde. The hydrogenation can be carried out in the presence of a solvent although this is not absolutely necessary.In order to purify the 3-(4-methylcyclohexyl)-butanal, the crude product may be distilled after having separated the catalyst.
The novel -methylenealdehydes according to the invention are particularly useful as perfume constituents and have fragances that differentiate them in a characteristic manner from other perfumes available on the market.
A particular advantage of the aldehyde is that they can be prepared from a cheap starting material readily available in large quantities, namely limonene.
The invention is illustrated by the following examples.
EXAMPLE 1
Preparation of 2-methylene-3-(4-methylcyclo- hex-3-enyl)-butanal.
A mixture of 332 g of 3-(4-methylcyclohex3-enyl)-butanal, 210 g of a 30% aqueous formaldehyde solution and 1 3 g of di-n-butylamine was heated in a flash for 60 minutes at a maximum temperature of 70 C while stirring and under reflux cooling. After separating the aqueous phase, a crude product was isolated which is shown by gas chrornatographic analysis to contain 94% of 2-methylene 3-(4-methylcyclohex-3-enyl)-butanal in addition to about 1% of the initial aldehyde. 311 g of a 99.4% pure aldehyde was isolated by distillation (Boiling point: 112 1::/13 mm Hg).
EXAMPLE 2
Preparation of 2-methylene-3-(4-methylcyclohexyl)-butanal.
A mixture of 336 g of 3-(4-methylcyclo- hexyl)-butanal, 210 g of a 30% aqueous formaldehyde solution and 1 3 g of di-n-butylamine was reacted under the conditions specified in Example 1. According to gas chromatographic analysis, the crude product contained 95% of 2-methylene-3-(4-methylcyclohexyl)-butanal in addition to 1% of the initial aldehyde. 320 g of a 99.1% pure aldehyde was isolated by distillation (Boiling Point: 110"C/13 mm Hg).
Claims (14)
1. A process for preparing 2-methylene-3 (4-methylcyclohex-3-enyl)-butanal or 2-methylene-3-(4-methylcyclohexyl)-butanal, comprising reacting 3-(4-methylcyclohex-3-enyl)-bu- tanal or 3-(4-methylcyclohexyl)-butanal with formaldehyde or a formaldehyde-forming compound and in the presence of a catalytic amount of a secondary amine.
2. A method according to any preceding claim, wherein the 3-(4-methylcyclohex-3enyl)-butanal is prepared from limonene by hyd roformylation or the 3-(4-methylcyclo hexyl)-butanal is prepared from limonene by hydroformylation of the limonene to yield 3 (4-methylcyclohex-3-enyl)-butanal and partial hydrogenation of the 3-(4-methylcyclohex-3 enyl)-butanal.
3. A process according to any preceding claim, wherein the 3-(4-methylcyclohex-3enyl)-butanal or the 3-(4-methylcyclohexyl)-butanal (as the first reactant) and the formal dehyde4orming compound (as the second reactant) are provided in a molar ratio of substantially 1 mole of the first reactant to 1 mole of the formaldehyde constituting or capable of being formed by the second reactant.
4. A process according to any preceding claim, wherein the secondary amine contains different alkyl radicals.
5. A process according to Claim 4, wherein the secondary amine is N-ethyl-nbutylamine, N-propyl-n-pentylamine or Nethyl-cyclohexylamine.
6. A process according to any of Claims 1 to 3, wherein the secondary amine contains two like alkyl radicals.
7. A process according to Claim 6, wherein the secondary amine is d-n-butylamine.
8. A process according to any preceding claim, wherein the reaction is carried out in the presence of 0.01 to 0.05 moles of secondary amine per mole of formaldehyde or per mole of formaldehyde capable of being formed by the formaldehyde-forming compound.
9. A process according to any preceding claim, wherein the reaction is carried out within the temperature range of 60 to 1 20 C.
10. A process according to Claim 9, wherein the reaction is carried out within the temperature range of 80 to 100"C.
11. A process according to any preceding claim, wherein the reaction is carried out in the presence of water or an alcohol.
1 2. A process according to Claim 1, sub stantially as described herein in either of the examples.
1 3. '2:methylene-3-(4-methylcyclohex-3- enyl)-butanal.
14. 2-rnethylene-3-(4-methylcyclohexyl)- butanal.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2921619A DE2921619C3 (en) | 1979-05-28 | 1979-05-28 | 2-methylene-3- (4-methylcyclohex-3-enyl) butanal and 2-methylene-3- (4-methylcyclohexyl) butanal and processes for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2054557A true GB2054557A (en) | 1981-02-18 |
| GB2054557B GB2054557B (en) | 1983-03-16 |
Family
ID=6071862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8015991A Expired GB2054557B (en) | 1979-05-28 | 1980-05-14 | Butanals |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5846509B2 (en) |
| CH (1) | CH643525A5 (en) |
| DE (1) | DE2921619C3 (en) |
| FR (1) | FR2457850A1 (en) |
| GB (1) | GB2054557B (en) |
| IT (1) | IT1147084B (en) |
| SE (1) | SE8003798L (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4956481A (en) * | 1988-10-21 | 1990-09-11 | International Flavors & Fragrances Inc. | Adamantane derivatives, compositions of matter containing same, processes for preparing said adamantane derivatives and said compositions, and organoleptic and deodorancy uses of said adamantane derivatives and said compositions |
| US5021184A (en) * | 1988-10-21 | 1991-06-04 | International Flavors & Fragrances Inc. | Adamantane derivatives, compositions of matter containing same, processes for preparing said adamantane derivatives and said compositions, and organoleptic and deodorancy uses of said adamantane derivatives and said compositions |
| US6451758B1 (en) * | 1998-05-08 | 2002-09-17 | Cognis Deutschland Gmbh | Aldehyde mixtures, compositions containing the same and methods of providing fragrance using the same |
| GB2529901A (en) * | 2014-09-08 | 2016-03-09 | Givaudan Sa | Organic compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10205835B4 (en) * | 2002-02-13 | 2004-11-11 | Celanese Chemicals Europe Gmbh | Process for the preparation of terpinolenaldehyde |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519327A (en) * | 1947-01-13 | 1950-08-15 | Fmc Corp | Condensation of beta-(4-methyl-delta3-cyclohexenyl)-butyraldehyde with aldehydes andketones |
| US2639295A (en) * | 1948-07-16 | 1953-05-19 | Eastman Kodak Co | Manufacture of unsaturated aldehydes |
| US3676505A (en) * | 1969-12-29 | 1972-07-11 | Procter & Gamble | 4-(4-methylcyclohex-3-en-1-yl)pent-4-en-1-ol and a process for its synthesis |
-
1979
- 1979-05-28 DE DE2921619A patent/DE2921619C3/en not_active Expired
-
1980
- 1980-05-14 GB GB8015991A patent/GB2054557B/en not_active Expired
- 1980-05-19 CH CH388480A patent/CH643525A5/en not_active IP Right Cessation
- 1980-05-20 FR FR8011260A patent/FR2457850A1/en not_active Withdrawn
- 1980-05-21 SE SE8003798A patent/SE8003798L/en not_active Application Discontinuation
- 1980-05-27 IT IT48810/80A patent/IT1147084B/en active
- 1980-05-28 JP JP55070231A patent/JPS5846509B2/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4956481A (en) * | 1988-10-21 | 1990-09-11 | International Flavors & Fragrances Inc. | Adamantane derivatives, compositions of matter containing same, processes for preparing said adamantane derivatives and said compositions, and organoleptic and deodorancy uses of said adamantane derivatives and said compositions |
| US4985403A (en) * | 1988-10-21 | 1991-01-15 | International Flavors & Fragrances Inc. | Use of adamantane derivatives in augmenting or enhancing the aroma of consumable materials |
| US5021184A (en) * | 1988-10-21 | 1991-06-04 | International Flavors & Fragrances Inc. | Adamantane derivatives, compositions of matter containing same, processes for preparing said adamantane derivatives and said compositions, and organoleptic and deodorancy uses of said adamantane derivatives and said compositions |
| US6451758B1 (en) * | 1998-05-08 | 2002-09-17 | Cognis Deutschland Gmbh | Aldehyde mixtures, compositions containing the same and methods of providing fragrance using the same |
| GB2529901A (en) * | 2014-09-08 | 2016-03-09 | Givaudan Sa | Organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2921619A1 (en) | 1980-12-04 |
| FR2457850A1 (en) | 1980-12-26 |
| DE2921619C3 (en) | 1982-05-19 |
| IT1147084B (en) | 1986-11-19 |
| CH643525A5 (en) | 1984-06-15 |
| DE2921619B2 (en) | 1981-05-07 |
| IT8048810A0 (en) | 1980-05-27 |
| JPS5846509B2 (en) | 1983-10-17 |
| SE8003798L (en) | 1980-11-29 |
| JPS55157563A (en) | 1980-12-08 |
| GB2054557B (en) | 1983-03-16 |
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