DE1240854B - Verfahren zur Herstellung von 3-Cyan-3, 5, 5-trimethylcyclohexanon aus Isophoron undBlausaeure - Google Patents
Verfahren zur Herstellung von 3-Cyan-3, 5, 5-trimethylcyclohexanon aus Isophoron undBlausaeureInfo
- Publication number
- DE1240854B DE1240854B DESCH36014A DESC036014A DE1240854B DE 1240854 B DE1240854 B DE 1240854B DE SCH36014 A DESCH36014 A DE SCH36014A DE SC036014 A DESC036014 A DE SC036014A DE 1240854 B DE1240854 B DE 1240854B
- Authority
- DE
- Germany
- Prior art keywords
- isophorone
- hydrocyanic acid
- reaction
- trimethylcyclohexanone
- cyano
- 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.)
- Pending
Links
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 14
- 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 title claims description 4
- 239000002253 acid Substances 0.000 title description 7
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- GMUGIWXUJVZLBQ-UHFFFAOYSA-N 3,5,5-trimethylcyclohex-2-en-1-one;hydrate Chemical compound O.CC1=CC(=O)CC(C)(C)C1 GMUGIWXUJVZLBQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- -1 alicyclic olefin ketones Chemical class 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- IJDSUFQMYUARCQ-QZTJIDSGSA-N diisophorone Chemical class C([C@@](C1)(C)C2)C(C)(C)C[C@]1(O)C1=C2CC(C)(C)CC1=O IJDSUFQMYUARCQ-QZTJIDSGSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 108090000935 Antithrombin III Proteins 0.000 description 1
- 102100022977 Antithrombin-III Human genes 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000006838 isophorone group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- 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
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
- C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
- C07C49/737—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having three rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH36014A DE1240854B (de) | 1964-10-24 | 1964-10-24 | Verfahren zur Herstellung von 3-Cyan-3, 5, 5-trimethylcyclohexanon aus Isophoron undBlausaeure |
| AT925465A AT262963B (de) | 1964-10-24 | 1965-10-13 | Verfahren zur Herstellung von 3-Cyan-3,5,5-trimethylcyclohexanon aus Isophoron und Blausäure |
| CH1450365A CH475206A (de) | 1964-10-24 | 1965-10-19 | Verfahren zur Herstellung von 3-Cyan-3.5.5-trimethyl-cyclohexanon aus Isophoron und Blausäure |
| LU49660A LU49660A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-10-24 | 1965-10-19 | |
| GB44660/65A GB1047920A (en) | 1964-10-24 | 1965-10-21 | Production of 3-cyano-3,5,5-trimethyl-1-cyclohexanone |
| ES0318745A ES318745A1 (es) | 1964-10-24 | 1965-10-21 | Procedimiento para la preparacion de 3-cian-3-5-5-trimetilciclohexanona de isoforona y acido cianhidrico. |
| NO160185A NO118795B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-10-24 | 1965-10-22 | |
| BE671300D BE671300A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-10-24 | 1965-10-22 | |
| SE13694/65A SE327978B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-10-24 | 1965-10-22 | |
| NL656513694A NL152253B (nl) | 1964-10-24 | 1965-10-22 | Werkwijze voor het bereiden van 3-cyaan-3,5,5-trimethylcyclohexanon uit isoforon en blauwzuur. |
| FR36023A FR1452374A (fr) | 1964-10-24 | 1965-10-23 | Procédé pour la fabrication du nitrile de l'acide dihydroisophoroncarboxylique, àpartir d'isophoron et d'acide cyanhydrique, et produits conformes à ceux ainsi obtenus ou similaire |
| DK545165AA DK134515B (da) | 1964-10-24 | 1965-10-23 | Fremgangsmåde til fremstilling af 3-cyan-3,5,5-trimethylcyclohexanon ud fra isophoron og hydrogencyanid. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH36014A DE1240854B (de) | 1964-10-24 | 1964-10-24 | Verfahren zur Herstellung von 3-Cyan-3, 5, 5-trimethylcyclohexanon aus Isophoron undBlausaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1240854B true DE1240854B (de) | 1967-05-24 |
Family
ID=7433704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH36014A Pending DE1240854B (de) | 1964-10-24 | 1964-10-24 | Verfahren zur Herstellung von 3-Cyan-3, 5, 5-trimethylcyclohexanon aus Isophoron undBlausaeure |
Country Status (12)
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011968A (en) * | 1990-02-06 | 1991-04-30 | W. R. Grace & Co.-Conn. | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| EP0433615A1 (de) * | 1989-12-21 | 1991-06-26 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von 1,3,3-Trimethyl-5-oxo-cyclohexan-carbonitril |
| US5179221A (en) * | 1991-03-05 | 1993-01-12 | Nippon Chemicals Co., Ltd. | Method for production of 3-cyano-3,5,5-trimethyl cyclohexanone |
| US5235089A (en) * | 1992-02-27 | 1993-08-10 | Hampshire Chemical Corp. | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| EP0554786A1 (de) * | 1992-02-07 | 1993-08-11 | BASF Aktiengesellschaft | Verfahren zur kontinuierlichen Herstellung von 3-Cyano-3,5,5-trimethylcyclohexanon |
| EP0757980A1 (de) | 1994-03-04 | 1997-02-12 | Basf Aktiengesellschaft | Verfahren zur Herstellung von 3-Aminomethyl-3,5,5-trimethylcyclohexylamin |
| EP1418172A3 (de) * | 2002-11-07 | 2004-10-06 | Basf Aktiengesellschaft | Verfahren zur CaO-katalysierten Herstellung von Isophoronnitril |
| US7652165B2 (en) | 2002-12-19 | 2010-01-26 | Basf Aktiengesellschaft | Neutralization of isophorone nitrile synthesis products |
| DE102010062603A1 (de) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 3-Aminomethyl-3,5,5-trimethylcyclohexylamin |
| DE102011077681A1 (de) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 3-Cyano-3,5,5-trimethylcyclohexanon |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2468584A1 (fr) | 1979-10-26 | 1981-05-08 | Ugine Kuhlmann | Procede de preparation de cyano-3-trimethyl-3,5,5-cyclohexanone |
| DE3640306A1 (de) * | 1986-11-26 | 1988-06-09 | Huels Chemische Werke Ag | Verfahren zur herstellung von 4.4.8.8.10-pentamethyl-10-cyano-bicyclo-(4.4.0)-decen-(1,6)-on-(2) |
| IT1236969B (it) * | 1989-11-02 | 1993-05-07 | Caffaro Spa Societa Per L Indu | Procedimento di preparazione di 3-ciano-3,5,5'-trimetil-1-cicloesanone. |
| US5183915A (en) * | 1992-03-05 | 1993-02-02 | Elf Atochem North America, Inc. | Catalyst and process for the production of 3-cyano-3,5,5-trialkylcyclohexanone |
| EP3392237B1 (de) | 2017-04-21 | 2019-10-02 | Evonik Degussa GmbH | Verfahren zur herstellung von acroleincyanhydrinen |
-
1964
- 1964-10-24 DE DESCH36014A patent/DE1240854B/de active Pending
-
1965
- 1965-10-13 AT AT925465A patent/AT262963B/de active
- 1965-10-19 CH CH1450365A patent/CH475206A/de not_active IP Right Cessation
- 1965-10-19 LU LU49660A patent/LU49660A1/xx unknown
- 1965-10-21 GB GB44660/65A patent/GB1047920A/en not_active Expired
- 1965-10-21 ES ES0318745A patent/ES318745A1/es not_active Expired
- 1965-10-22 NL NL656513694A patent/NL152253B/xx unknown
- 1965-10-22 SE SE13694/65A patent/SE327978B/xx unknown
- 1965-10-22 BE BE671300D patent/BE671300A/xx unknown
- 1965-10-22 NO NO160185A patent/NO118795B/no unknown
- 1965-10-23 FR FR36023A patent/FR1452374A/fr not_active Expired
- 1965-10-23 DK DK545165AA patent/DK134515B/da unknown
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0433615A1 (de) * | 1989-12-21 | 1991-06-26 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von 1,3,3-Trimethyl-5-oxo-cyclohexan-carbonitril |
| US5091554A (en) * | 1989-12-21 | 1992-02-25 | Degussa Ag | Method of preparing 1,3,3-trimethyl-5-oxo-cyclohexane carbonitrile |
| US5011968A (en) * | 1990-02-06 | 1991-04-30 | W. R. Grace & Co.-Conn. | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| US5179221A (en) * | 1991-03-05 | 1993-01-12 | Nippon Chemicals Co., Ltd. | Method for production of 3-cyano-3,5,5-trimethyl cyclohexanone |
| JP3241472B2 (ja) | 1992-02-07 | 2001-12-25 | ビーエーエスエフ アクチェンゲゼルシャフト | ３−シアノ−３，５，５−トリメチルシクロヘキサノンの連続的製造方法 |
| EP0554786A1 (de) * | 1992-02-07 | 1993-08-11 | BASF Aktiengesellschaft | Verfahren zur kontinuierlichen Herstellung von 3-Cyano-3,5,5-trimethylcyclohexanon |
| US5254711A (en) * | 1992-02-07 | 1993-10-19 | Basf Aktiengesellschaft | Continuous preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| US5235089A (en) * | 1992-02-27 | 1993-08-10 | Hampshire Chemical Corp. | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| EP0558332A1 (en) * | 1992-02-27 | 1993-09-01 | Hampshire Chemical Corporation | Process for the preparation of 3-cyano-3,5,5- trimethylcyclohexanone |
| EP0757980A1 (de) | 1994-03-04 | 1997-02-12 | Basf Aktiengesellschaft | Verfahren zur Herstellung von 3-Aminomethyl-3,5,5-trimethylcyclohexylamin |
| EP1418172A3 (de) * | 2002-11-07 | 2004-10-06 | Basf Aktiengesellschaft | Verfahren zur CaO-katalysierten Herstellung von Isophoronnitril |
| US7652165B2 (en) | 2002-12-19 | 2010-01-26 | Basf Aktiengesellschaft | Neutralization of isophorone nitrile synthesis products |
| DE102010062603A1 (de) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 3-Aminomethyl-3,5,5-trimethylcyclohexylamin |
| WO2012076317A1 (de) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Verfahren zur herstellung von 3-aminomethyl-3,5,5-trimethylcyclohexylamin |
| US9085506B2 (en) | 2010-12-08 | 2015-07-21 | Evonik Degussa Gmbh | Process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine |
| DE102011077681A1 (de) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 3-Cyano-3,5,5-trimethylcyclohexanon |
| WO2012171830A1 (de) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Verfahren zur herstellung von 3-cyano-3,5,5-trimethylcyclohexanon |
Also Published As
| Publication number | Publication date |
|---|---|
| NL152253B (nl) | 1977-02-15 |
| AT262963B (de) | 1968-07-10 |
| NL6513694A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-04-25 |
| NO118795B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-02-16 |
| DK134515C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-18 |
| CH475206A (de) | 1969-07-15 |
| DK134515B (da) | 1976-11-22 |
| BE671300A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-02-14 |
| SE327978B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-09-07 |
| GB1047920A (en) | 1966-11-09 |
| FR1452374A (fr) | 1966-02-25 |
| ES318745A1 (es) | 1966-05-01 |
| LU49660A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-20 |
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