JPS62164656A - シアノイソホロンの製造法 - Google Patents
シアノイソホロンの製造法Info
- Publication number
- JPS62164656A JPS62164656A JP435786A JP435786A JPS62164656A JP S62164656 A JPS62164656 A JP S62164656A JP 435786 A JP435786 A JP 435786A JP 435786 A JP435786 A JP 435786A JP S62164656 A JPS62164656 A JP S62164656A
- Authority
- JP
- Japan
- Prior art keywords
- cyanoisophorone
- acetal
- solvent
- acid catalyst
- reaction
- 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
- 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 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 polymethylene Polymers 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 239000003377 acid catalyst Substances 0.000 claims abstract description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 5
- 239000000126 substance Substances 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000004593 Epoxy Substances 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011527 polyurethane coating Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000005977 Ethylene Substances 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- 239000003054 catalyst Substances 0.000 description 2
- 230000008034 disappearance Effects 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
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
- JJDFVIDVSCYKDS-UHFFFAOYSA-N 1,3,3-trimethyl-5-oxocyclohexane-1-carbonitrile Chemical compound CC1(C)CC(=O)CC(C)(C#N)C1 JJDFVIDVSCYKDS-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
- 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
- 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
- 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
- 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 true JPS62164656A (ja) | 1987-07-21 |
| JPH0584305B2 JPH0584305B2 (enrdf_load_stackoverflow) | 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 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5179221A (en) * | 1991-03-05 | 1993-01-12 | Nippon Chemicals Co., Ltd. | Method for production of 3-cyano-3,5,5-trimethyl cyclohexanone |
| WO2012171830A1 (de) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Verfahren zur herstellung von 3-cyano-3,5,5-trimethylcyclohexanon |
| CN105985260A (zh) * | 2015-03-19 | 2016-10-05 | 赢创德固赛有限公司 | 由异佛尔酮腈产物混合物分离阳离子的方法 |
-
1986
- 1986-01-14 JP JP435786A patent/JPS62164656A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5179221A (en) * | 1991-03-05 | 1993-01-12 | Nippon Chemicals Co., Ltd. | Method for production of 3-cyano-3,5,5-trimethyl cyclohexanone |
| WO2012171830A1 (de) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Verfahren zur herstellung von 3-cyano-3,5,5-trimethylcyclohexanon |
| DE102011077681A1 (de) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 3-Cyano-3,5,5-trimethylcyclohexanon |
| CN105985260A (zh) * | 2015-03-19 | 2016-10-05 | 赢创德固赛有限公司 | 由异佛尔酮腈产物混合物分离阳离子的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0584305B2 (enrdf_load_stackoverflow) | 1993-12-01 |
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