JPS5846509B2 - 新規２−メチレン−３−置換ブタナ−ル及びその製法 - Google Patents

新規２−メチレン−３−置換ブタナ−ル及びその製法

Info

Publication number: JPS5846509B2
Authority: JP; Japan
Prior art keywords: butanal; methylene; formaldehyde; enyl; methylcyclohex
Prior art date: 1979-05-28
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.): Expired

Application number

JP55070231A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55157563A (en

Inventor

ヘルムート・シユプリンガー

ユールゲン・ヴエーバー

ヴオルフガング・ベルンハーゲン

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.)

Ruhrchemie AG

Original Assignee

Ruhrchemie AG

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.)

1979-05-28

Filing date

1980-05-28

Publication date

1983-10-17

1980-05-28 Application filed by Ruhrchemie AG filed Critical Ruhrchemie AG

1980-12-08 Publication of JPS55157563A publication Critical patent/JPS55157563A/ja

1983-10-17 Publication of JPS5846509B2 publication Critical patent/JPS5846509B2/ja

Status Expired legal-status Critical Current

Links

-1 2-methylene-3-substituted butanal Chemical class 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title claims description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 43
150000001875 compounds Chemical class 0.000 claims description 9
YZFPDESEFZSBIN-UHFFFAOYSA-N 3-(4-methylcyclohexyl)butanal Chemical compound O=CCC(C)C1CCC(C)CC1 YZFPDESEFZSBIN-UHFFFAOYSA-N 0.000 claims description 4
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 2
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
150000001299 aldehydes Chemical class 0.000 description 11
239000003054 catalyst Substances 0.000 description 10
VJYFMQREUJXCQV-UHFFFAOYSA-N Limonene aldehyde Chemical compound O=CCC(C)C1CCC(C)=CC1 VJYFMQREUJXCQV-UHFFFAOYSA-N 0.000 description 7
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 5
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 5
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 description 4
YIAJIVSUDZUUOG-UHFFFAOYSA-N 3-(4-methylcyclohexyl)-2-methylidenebutanal Chemical compound O=CC(=C)C(C)C1CCC(C)CC1 YIAJIVSUDZUUOG-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
239000012043 crude product Substances 0.000 description 3
239000002904 solvent 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
238000009835 boiling Methods 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004821 distillation Methods 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
229940087305 limonene Drugs 0.000 description 2
235000001510 limonene Nutrition 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 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
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 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
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000007037 hydroformylation reaction 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
238000002955 isolation Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
238000005822 methylenation reaction Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
GFAQQAUTKWCQHA-UHFFFAOYSA-N n-propylpentan-1-amine Chemical compound CCCCCNCCC GFAQQAUTKWCQHA-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
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-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

Landscapes

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

JP55070231A 1979-05-28 1980-05-28 新規２−メチレン−３−置換ブタナ−ル及びその製法 Expired JPS5846509B2 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2921619A DE2921619C3 (de)	1979-05-28	1979-05-28	2-Methylen-3-(4-methylcyclohex-3-enyl)-butanal und 2-Methylen-3-(4-methylcyclohexyl)-butanal und Verfahren zu ihrer Herstellung

Publications (2)

Publication Number	Publication Date
JPS55157563A JPS55157563A (en)	1980-12-08
JPS5846509B2 true JPS5846509B2 (ja)	1983-10-17

Family

ID=6071862

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP55070231A Expired JPS5846509B2 (ja)	1979-05-28	1980-05-28	新規２−メチレン−３−置換ブタナ−ル及びその製法

Country Status (7)

Country	Link
JP (1)	JPS5846509B2 (de)
CH (1)	CH643525A5 (de)
DE (1)	DE2921619C3 (de)
FR (1)	FR2457850A1 (de)
GB (1)	GB2054557B (de)
IT (1)	IT1147084B (de)
SE (1)	SE8003798L (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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
DE19820657A1 (de)	1998-05-08	1999-11-11	Henkel Kgaa	Riechstoff-Zusammensetzungen
DE10205835B4 (de) *	2002-02-13	2004-11-11	Celanese Chemicals Europe Gmbh	Verfahren zur Herstellung von Terpinolenaldehyd
GB2529901A (en) *	2014-09-08	2016-03-09	Givaudan Sa	Organic compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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/de not_active Expired
1980
- 1980-05-14 GB GB8015991A patent/GB2054557B/en not_active Expired
- 1980-05-19 CH CH388480A patent/CH643525A5/de not_active IP Right Cessation
- 1980-05-20 FR FR8011260A patent/FR2457850A1/fr not_active Withdrawn
- 1980-05-21 SE SE8003798A patent/SE8003798L/xx not_active Application Discontinuation
- 1980-05-27 IT IT48810/80A patent/IT1147084B/it active
- 1980-05-28 JP JP55070231A patent/JPS5846509B2/ja not_active Expired

Also Published As

Publication number	Publication date
JPS55157563A (en)	1980-12-08
DE2921619A1 (de)	1980-12-04
IT1147084B (it)	1986-11-19
CH643525A5 (de)	1984-06-15
DE2921619B2 (de)	1981-05-07
IT8048810A0 (it)	1980-05-27
DE2921619C3 (de)	1982-05-19
GB2054557B (en)	1983-03-16
FR2457850A1 (fr)	1980-12-26
SE8003798L (sv)	1980-11-29
GB2054557A (en)	1981-02-18

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