JPH0584305B2 - - Google Patents
Info
- Publication number
- JPH0584305B2 JPH0584305B2 JP435786A JP435786A JPH0584305B2 JP H0584305 B2 JPH0584305 B2 JP H0584305B2 JP 435786 A JP435786 A JP 435786A JP 435786 A JP435786 A JP 435786A JP H0584305 B2 JPH0584305 B2 JP H0584305B2
- Authority
- JP
- Japan
- Prior art keywords
- cyanoisophorone
- acetal
- reaction
- solvent
- ethylene
- 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.)
- Expired - Lifetime
Links
- NSGLXUMORGEZEF-UHFFFAOYSA-N 2,4,4-trimethyl-6-oxocyclohexene-1-carbonitrile Chemical compound CC1=C(C#N)C(=O)CC(C)(C)C1 NSGLXUMORGEZEF-UHFFFAOYSA-N 0.000 claims description 38
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 18
- -1 polymethylene group Polymers 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-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
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZLMHETMAEHQFHK-UHFFFAOYSA-N 2,2-dimethylheptan-3-one Chemical compound CCCCC(=O)C(C)(C)C ZLMHETMAEHQFHK-UHFFFAOYSA-N 0.000 description 1
- ROSFUFIOLRQOON-UHFFFAOYSA-N 2,4-Dimethyl-1,3-dioxolane Chemical compound CC1COC(C)O1 ROSFUFIOLRQOON-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP435786A JPS62164656A (ja) | 1986-01-14 | 1986-01-14 | シアノイソホロンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP435786A JPS62164656A (ja) | 1986-01-14 | 1986-01-14 | シアノイソホロンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62164656A JPS62164656A (ja) | 1987-07-21 |
| JPH0584305B2 true JPH0584305B2 (en]) | 1993-12-01 |
Family
ID=11582140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP435786A Granted JPS62164656A (ja) | 1986-01-14 | 1986-01-14 | シアノイソホロンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62164656A (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04279559A (ja) * | 1991-03-05 | 1992-10-05 | Nippo Kagaku Kk | ３−シアノ−３，５，５−トリメチルシクロヘキサノンの製造方法 |
| DE102011077681A1 (de) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 3-Cyano-3,5,5-trimethylcyclohexanon |
| ES2647495T3 (es) * | 2015-03-19 | 2017-12-21 | Evonik Degussa Gmbh | Procedimiento para la separación de cationes a partir de una mezcla de productos de isoforonanitrilo |
-
1986
- 1986-01-14 JP JP435786A patent/JPS62164656A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62164656A (ja) | 1987-07-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU198437B (en) | Process for producing mono- or bis-carbonyl-compounds | |
| KR101223949B1 (ko) | １,４-부탄디올의 정제 방법 | |
| JP2020090492A (ja) | トリアセトンアミンの改良製造法 | |
| KR20060132860A (ko) | 1,3-부틸렌 글라이콜의 제조 방법 | |
| JPS62246529A (ja) | １，３−ブチレングリコ−ルの製造方法 | |
| JPH0584305B2 (en]) | ||
| JPS5935904B2 (ja) | 新規な化合物の製造方法 | |
| US6166225A (en) | Processes for producing dialdehyde monoacetals | |
| JP2830210B2 (ja) | α，β―不飽和ケトン類の合成法 | |
| JPH0791264B2 (ja) | Ｎ−（２−アミノ−３−ヒドロキシベンゾイル）−ｌ−プロリナ−ルアセタ−ルおよびその製造方法 | |
| JP3795970B2 (ja) | α，β−不飽和アルデヒドの製造方法 | |
| US3287372A (en) | Process and intermediates for manufacture of 2-(dialkylmethyl)-5-alkyl-2-cyclohexen-1-ones | |
| JPH0273033A (ja) | ４，４―ジメチル―１―（ｐ―クロロフエニル）ペンタン―３―オンの製造方法 | |
| US4532082A (en) | Preparation of 3-cyano-2-alkylalkanals | |
| JPH0250101B2 (en]) | ||
| JP2921054B2 (ja) | アルコキシ―α，β―不飽和ケトンの合成法 | |
| JP4216042B2 (ja) | シクロプロピルアセトニトリルの製造方法 | |
| JPS5819665B2 (ja) | サクシニルコハクサンジエステルノ セイゾウホウ | |
| JP3227020B2 (ja) | ケタール類及びその製造法 | |
| CN119528959A (zh) | 一种1-癸炔-5-醇及其衍生物的制备方法 | |
| JPH08109170A (ja) | ヘキサヒドロピリダジンの製造方法 | |
| US20050020846A1 (en) | Processes for preparation of cyclopropylethanol, cyclo-propylacetonitrile and intermediates of both | |
| JPH09124532A (ja) | グリセリルエーテルの製造方法 | |
| JPS647982B2 (en]) | ||
| JP2000038384A (ja) | グルタルアルデヒドモノアセタールの製造方法 |