JPS6072840A - 2−アルキリデンシクロヘキサノンの製造法 - Google Patents
2−アルキリデンシクロヘキサノンの製造法Info
- Publication number
- JPS6072840A JPS6072840A JP58179986A JP17998683A JPS6072840A JP S6072840 A JPS6072840 A JP S6072840A JP 58179986 A JP58179986 A JP 58179986A JP 17998683 A JP17998683 A JP 17998683A JP S6072840 A JPS6072840 A JP S6072840A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexanone
- reaction
- aliphatic aldehyde
- alkali
- water
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 71
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- -1 aliphatic aldehyde Chemical class 0.000 claims abstract description 26
- 239000010410 layer Substances 0.000 claims abstract description 21
- 239000012044 organic layer Substances 0.000 claims abstract description 18
- 239000003513 alkali Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 11
- 230000018044 dehydration Effects 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 238000010406 interfacial reaction Methods 0.000 claims description 17
- 230000005494 condensation Effects 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 239000007764 o/w emulsion Substances 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 3
- 239000000839 emulsion Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005882 aldol condensation reaction Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- MYSLPKPAMDRDGE-UHFFFAOYSA-N 2-butylidenecyclohexan-1-one Chemical compound CCCC=C1CCCCC1=O MYSLPKPAMDRDGE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000001715 Lentinula edodes Nutrition 0.000 description 1
- 240000000599 Lentinula edodes Species 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen 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
- C07C45/67—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
-
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58179986A JPS6072840A (ja) | 1983-09-28 | 1983-09-28 | 2−アルキリデンシクロヘキサノンの製造法 |
| DE3435003A DE3435003C2 (de) | 1983-09-28 | 1984-09-24 | Verfahren zur Herstellung von 2-Alkyliden-cyclohexanon |
| GB08424418A GB2146995B (en) | 1983-09-28 | 1984-09-27 | Process for preparing 2-(1-hydroxyalkyl) cyclohexanone and/or 2-alkylidene cyclohexanone |
| CH4643/84A CH662344A5 (de) | 1983-09-28 | 1984-09-27 | Verfahren zur herstellung von 2-(1-hydroxyalkyl)-cyclohexanon und/oder 2-alkyliden-cyclohexanon. |
| US06/825,787 US4668827A (en) | 1983-09-28 | 1986-02-04 | Process for preparing 2-(1-hydroxyalkyl) cyclohexanone and/or 2-alkylidene cyclohexanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58179986A JPS6072840A (ja) | 1983-09-28 | 1983-09-28 | 2−アルキリデンシクロヘキサノンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6072840A true JPS6072840A (ja) | 1985-04-24 |
| JPH0125732B2 JPH0125732B2 (enExample) | 1989-05-19 |
Family
ID=16075453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58179986A Granted JPS6072840A (ja) | 1983-09-28 | 1983-09-28 | 2−アルキリデンシクロヘキサノンの製造法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4668827A (enExample) |
| JP (1) | JPS6072840A (enExample) |
| CH (1) | CH662344A5 (enExample) |
| DE (1) | DE3435003C2 (enExample) |
| GB (1) | GB2146995B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004523472A (ja) * | 2000-09-20 | 2004-08-05 | コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト | 分岐アルコールおよび/または炭化水素の製造方法 |
| JP2005255646A (ja) * | 2004-03-15 | 2005-09-22 | Kao Corp | シクロアルカノン類含有組成物 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3707209A1 (de) * | 1987-03-06 | 1988-09-15 | Henkel Kgaa | 2-alkyliden-3,3,5(3,5,5)-trimethylcyclopentanone als riechstoffe |
| US7161041B2 (en) | 2002-12-26 | 2007-01-09 | Kao Corporation | Process for producing cycloalkanone derivatives |
Family Cites Families (2)
| 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 |
| US3942761A (en) * | 1971-01-04 | 1976-03-09 | Monsanto Company | 4-(2'-Norbornyl)-2-butanones |
-
1983
- 1983-09-28 JP JP58179986A patent/JPS6072840A/ja active Granted
-
1984
- 1984-09-24 DE DE3435003A patent/DE3435003C2/de not_active Expired - Fee Related
- 1984-09-27 GB GB08424418A patent/GB2146995B/en not_active Expired
- 1984-09-27 CH CH4643/84A patent/CH662344A5/de not_active IP Right Cessation
-
1986
- 1986-02-04 US US06/825,787 patent/US4668827A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004523472A (ja) * | 2000-09-20 | 2004-08-05 | コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト | 分岐アルコールおよび/または炭化水素の製造方法 |
| JP2005255646A (ja) * | 2004-03-15 | 2005-09-22 | Kao Corp | シクロアルカノン類含有組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2146995A (en) | 1985-05-01 |
| DE3435003C2 (de) | 1995-05-24 |
| GB8424418D0 (en) | 1984-10-31 |
| US4668827A (en) | 1987-05-26 |
| JPH0125732B2 (enExample) | 1989-05-19 |
| CH662344A5 (de) | 1987-09-30 |
| DE3435003A1 (de) | 1985-04-04 |
| GB2146995B (en) | 1986-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6383079A (ja) | 2−クロル−5−クロルメチルチアゾールの製造法 | |
| CN101605774B (zh) | 2-甲基-3-(3,4-亚甲二氧苯基)丙醛及其制造方法 | |
| HU185896B (en) | New process for producing 7-hydroxy-2,2-dimethyl-2,3-dihydro-bracket-benzo-furane-bracket closed | |
| JPH0336816B2 (enExample) | ||
| JPS6072840A (ja) | 2−アルキリデンシクロヘキサノンの製造法 | |
| JP2542683B2 (ja) | ベンゾトリフルオライドの製造方法 | |
| JPS6130659B2 (enExample) | ||
| JPS5899473A (ja) | α−アセチルラクトン類の製造方法 | |
| JP2000026356A (ja) | ヒドロキシピバルアルデヒドの製造方法 | |
| JPS62198637A (ja) | 1,1,3−トリクロルアセトンの製造方法 | |
| JPH0747557B2 (ja) | ヘプタフルオロイソブテニル低級アルキルエーテルの製造法 | |
| JPS597699B2 (ja) | インドリン類の製造方法 | |
| RU2796102C1 (ru) | Способ получения 1-(2-бромэтокси)-2-метоксибензола | |
| JPH1059892A (ja) | α,β−不飽和アルデヒドの製造方法 | |
| CA2268226A1 (en) | Process for preparing 3-methoxy-1-propanol | |
| JP2586949B2 (ja) | p―又はm―ヒドロキシベンズアルデヒドの製造法 | |
| JP3001626B2 (ja) | 2―クロロプロピオンアルデヒド三量体およびその製造方法 | |
| JPH07258246A (ja) | ピペロナールの製造法 | |
| JP2653138B2 (ja) | ハロアリルフランカルビノール類およびその製法 | |
| JP2001206883A (ja) | 3,4−メチレンジオキシマンデル酸の製造法 | |
| JPS5813532A (ja) | オルト−メタリルオキシフエノ−ルの製造方法 | |
| US4211704A (en) | Method for producing 2,3,3-trimethylindolenine | |
| JP3831975B2 (ja) | ピロガロールの製造方法 | |
| JP2002371046A (ja) | 2−ヒドロキシカルボン酸アミドの製法 | |
| JPS5858335B2 (ja) | アルフア − チカンアセトンノセイゾウホウ |