DE19944524A1 - Verfahren zur Herstellung von Alkyl-substituierten Butenolen - Google Patents
Verfahren zur Herstellung von Alkyl-substituierten ButenolenInfo
- Publication number
- DE19944524A1 DE19944524A1 DE19944524A DE19944524A DE19944524A1 DE 19944524 A1 DE19944524 A1 DE 19944524A1 DE 19944524 A DE19944524 A DE 19944524A DE 19944524 A DE19944524 A DE 19944524A DE 19944524 A1 DE19944524 A1 DE 19944524A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- aldehydes
- carbon atoms
- substituted
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000008569 process Effects 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 230000009467 reduction Effects 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 20
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 9
- -1 2,2,3-trimethylcyclopent-3-en-1-yl Chemical group 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003205 fragrance Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- OGCGGWYLHSJRFY-VIFPVBQESA-N 2-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]acetaldehyde Chemical compound CC1=CC[C@@H](CC=O)C1(C)C OGCGGWYLHSJRFY-VIFPVBQESA-N 0.000 description 4
- 240000009101 Sandoricum indicum Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000010671 sandalwood oil Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000009419 refurbishment Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- ZFYIQPIHXRFFCZ-QMMMGPOBSA-N (2s)-2-(cyclohexylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC1CCCCC1 ZFYIQPIHXRFFCZ-QMMMGPOBSA-N 0.000 description 1
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- MDHYNKOGDVNPJZ-UHFFFAOYSA-N 2-methyl-3-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal Chemical compound O=CC(C)=C(C)C1CC=C(C)C1(C)C MDHYNKOGDVNPJZ-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
- 229910017518 Cu Zn Inorganic materials 0.000 description 1
- 229910017752 Cu-Zn Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 229910017943 Cu—Zn Inorganic materials 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- XHHVGWIXNLQBHK-UHFFFAOYSA-N N-methylmethanamine pyridin-2-yl acetate Chemical compound CNC.CC(=O)OC1=CC=CC=N1 XHHVGWIXNLQBHK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical class [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- MIJRUQYZDSEMBD-UHFFFAOYSA-N acetic acid;morpholine Chemical compound CC(O)=O.C1COCCN1 MIJRUQYZDSEMBD-UHFFFAOYSA-N 0.000 description 1
- MQFIKAWTCOXAAY-UHFFFAOYSA-N acetic acid;n-butylbutan-1-amine Chemical compound CC([O-])=O.CCCC[NH2+]CCCC MQFIKAWTCOXAAY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011217 control strategy Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate trihydrate Substances [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- HMSINBTULZNZRC-UHFFFAOYSA-N n-acetyl-n-(2-aminoethyl)acetamide Chemical compound CC(=O)N(C(C)=O)CCN HMSINBTULZNZRC-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- HAGVWBQWCRHRRA-UHFFFAOYSA-N piperidin-1-yl acetate Chemical compound CC(=O)ON1CCCCC1 HAGVWBQWCRHRRA-UHFFFAOYSA-N 0.000 description 1
- PQAOZIUSXRFFSR-UHFFFAOYSA-N piperidin-1-yl formate Chemical compound O=CON1CCCCC1 PQAOZIUSXRFFSR-UHFFFAOYSA-N 0.000 description 1
- DULUTFPZVOEDKZ-UHFFFAOYSA-N piperidin-1-yl propanoate Chemical compound CCC(=O)ON1CCCCC1 DULUTFPZVOEDKZ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- NCHPDGCQTUJYKK-UHFFFAOYSA-N pyrrolidin-1-ium;acetate Chemical compound CC(O)=O.C1CCNC1 NCHPDGCQTUJYKK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- JGPSMWXKRPZZRG-UHFFFAOYSA-N zinc;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O JGPSMWXKRPZZRG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C45/74—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 combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19944524A DE19944524A1 (de) | 1999-09-17 | 1999-09-17 | Verfahren zur Herstellung von Alkyl-substituierten Butenolen |
| EP00964140A EP1212272B1 (de) | 1999-09-17 | 2000-09-08 | Verfahren zur herstellung von alkyl-substituierten butenolen |
| JP2001524949A JP2004513871A (ja) | 1999-09-17 | 2000-09-08 | アルキル置換ブテノールの製造方法 |
| AT00964140T ATE256098T1 (de) | 1999-09-17 | 2000-09-08 | Verfahren zur herstellung von alkyl- substituierten butenolen |
| US10/088,385 US7169749B1 (en) | 1999-09-17 | 2000-09-08 | Method for producing alkyl-substituted butenols |
| IL14868600A IL148686A0 (en) | 1999-09-17 | 2000-09-08 | Method for producing alkyl-substituted butenols |
| ES00964140T ES2209991T3 (es) | 1999-09-17 | 2000-09-08 | Procedimiento para la obtencion de butenoles alquil-substituidos. |
| PCT/EP2000/008772 WO2001021568A1 (de) | 1999-09-17 | 2000-09-08 | Verfahren zur herstellung von alkyl-substituierten butenolen |
| DE50004746T DE50004746D1 (de) | 1999-09-17 | 2000-09-08 | Verfahren zur herstellung von alkyl-substituierten butenolen |
| IL148686A IL148686A (en) | 1999-09-17 | 2002-03-14 | Method for producing alkyl-substituted butenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19944524A DE19944524A1 (de) | 1999-09-17 | 1999-09-17 | Verfahren zur Herstellung von Alkyl-substituierten Butenolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19944524A1 true DE19944524A1 (de) | 2001-03-22 |
Family
ID=7922313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19944524A Withdrawn DE19944524A1 (de) | 1999-09-17 | 1999-09-17 | Verfahren zur Herstellung von Alkyl-substituierten Butenolen |
| DE50004746T Expired - Lifetime DE50004746D1 (de) | 1999-09-17 | 2000-09-08 | Verfahren zur herstellung von alkyl-substituierten butenolen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50004746T Expired - Lifetime DE50004746D1 (de) | 1999-09-17 | 2000-09-08 | Verfahren zur herstellung von alkyl-substituierten butenolen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7169749B1 (enExample) |
| EP (1) | EP1212272B1 (enExample) |
| JP (1) | JP2004513871A (enExample) |
| AT (1) | ATE256098T1 (enExample) |
| DE (2) | DE19944524A1 (enExample) |
| ES (1) | ES2209991T3 (enExample) |
| IL (2) | IL148686A0 (enExample) |
| WO (1) | WO2001021568A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4886283B2 (ja) * | 2005-12-01 | 2012-02-29 | 花王株式会社 | α，β−不飽和アルデヒド化合物の製造方法 |
| JP5001549B2 (ja) * | 2005-12-06 | 2012-08-15 | 花王株式会社 | α−アルキルシンナムアルデヒド類の製造方法 |
| DE102007027371A1 (de) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | Verfahren zur Herstellung einer Verbindung aufweisend mindestens eine Ester-Gruppe |
| DE102007027372A1 (de) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | Verfahren zur Hydrierung von Glycerin |
| CN103804146A (zh) * | 2012-11-15 | 2014-05-21 | 国际香料和香精公司 | 2-烷基-4-(2,2,3-三甲基-环戊-3-烯基)-丁-2-烯-1-醇及其制备方法 |
| CN108383700A (zh) * | 2018-03-15 | 2018-08-10 | 江苏馨瑞香料有限公司 | 一种甲基壬乙醛的合成方法 |
| JP7709461B2 (ja) * | 2020-05-29 | 2025-07-16 | ダウ グローバル テクノロジーズ エルエルシー | 非水性アルドール縮合のための有機触媒 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072720A (en) * | 1971-01-19 | 1978-02-07 | Mobil Oil Corporation | Production of alcohol |
| JPS5536423A (en) | 1978-09-08 | 1980-03-14 | Taiyo Koryo Kk | Perfume compound, its preparation, and perfumery composition |
| DE4242466C2 (de) | 1992-12-16 | 2003-07-03 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von Fettalkoholen |
| DE19520103A1 (de) * | 1995-06-01 | 1996-12-05 | Henkel Kgaa | Verfahren zur Herstellung von Alkyl-substituierten Butenolen |
| JP3400291B2 (ja) * | 1996-09-17 | 2003-04-28 | 高砂香料工業株式会社 | （ｅ）−（ｒ）−２−アルキル−４−（２，２，３−トリメチルシクロペント−３−エン−１−イル）−２−ブテン−１−オール誘導体、その製造方法および用途 |
-
1999
- 1999-09-17 DE DE19944524A patent/DE19944524A1/de not_active Withdrawn
-
2000
- 2000-09-08 WO PCT/EP2000/008772 patent/WO2001021568A1/de not_active Ceased
- 2000-09-08 DE DE50004746T patent/DE50004746D1/de not_active Expired - Lifetime
- 2000-09-08 EP EP00964140A patent/EP1212272B1/de not_active Expired - Lifetime
- 2000-09-08 ES ES00964140T patent/ES2209991T3/es not_active Expired - Lifetime
- 2000-09-08 JP JP2001524949A patent/JP2004513871A/ja not_active Withdrawn
- 2000-09-08 US US10/088,385 patent/US7169749B1/en not_active Expired - Fee Related
- 2000-09-08 AT AT00964140T patent/ATE256098T1/de not_active IP Right Cessation
- 2000-09-08 IL IL14868600A patent/IL148686A0/xx active IP Right Grant
-
2002
- 2002-03-14 IL IL148686A patent/IL148686A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001021568A1 (de) | 2001-03-29 |
| ES2209991T3 (es) | 2004-07-01 |
| IL148686A (en) | 2006-12-31 |
| WO2001021568A9 (de) | 2003-11-27 |
| US7169749B1 (en) | 2007-01-30 |
| JP2004513871A (ja) | 2004-05-13 |
| ATE256098T1 (de) | 2003-12-15 |
| EP1212272B1 (de) | 2003-12-10 |
| DE50004746D1 (de) | 2004-01-22 |
| EP1212272A1 (de) | 2002-06-12 |
| IL148686A0 (en) | 2002-09-12 |
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