GB733650A - Isophorone and its homologues - Google Patents
Isophorone and its homologuesInfo
- Publication number
- GB733650A GB733650A GB22531/52A GB2253152A GB733650A GB 733650 A GB733650 A GB 733650A GB 22531/52 A GB22531/52 A GB 22531/52A GB 2253152 A GB2253152 A GB 2253152A GB 733650 A GB733650 A GB 733650A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isophorone
- products
- cycled
- fractionated
- ketones
- 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
Links
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 title abstract 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 150000002576 ketones Chemical class 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises a process for the preparation of isophorone and its homologues from ketones of 3-6 C atoms by condensing the ketone or a mixture of such ketones with alkali hydroxide dissolved in an aliphatic, alicyclic or aromatic alcohol, with or without water present, and recycling higher condensation products, optionally with water for hydrolysis to isophorone and acetone. The products may be fractionated and part re-cycled. In examples, acetone is heated in an autoclave with 1/2 N-methanolic sodium or potassium hydroxide, or lithium hydroxide, under various conditions to give isophorone, mesityl oxide and other products, some fractionated and re-cycled; methyl ethyl ketone similarly gives methyl-3-heptene-3-one-4 and an isophorone of 12 C. Other alcoholic solvents specified include cyclohexanol and benzyl alcohol. Specification 524,151 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR733650X | 1951-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB733650A true GB733650A (en) | 1955-07-13 |
Family
ID=9126328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22531/52A Expired GB733650A (en) | 1951-09-08 | 1952-09-08 | Isophorone and its homologues |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB733650A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337633A (en) * | 1960-12-31 | 1967-08-22 | Hibernia Chemie G M B H | Production of isophorone |
| US3337632A (en) * | 1960-12-23 | 1967-08-22 | Hibernia Chemic G M B H | Process for recovering isophorone in high purity |
| EP0295361A3 (en) * | 1987-06-16 | 1990-01-24 | Union Camp Corporation | Preparation of pseudoionones |
| DE102010062603A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine |
| DE102010062587A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for the preparation of isophorone |
| CN102775287A (en) * | 2011-05-13 | 2012-11-14 | 赢创德固赛有限责任公司 | Process for preparing isophorone in the presence of at least one defoamer in the wastewater column in the workup section |
| CN108658737A (en) * | 2018-03-19 | 2018-10-16 | 江苏焕鑫新材料股份有限公司 | A kind of the deep pyrolytic resource utilization process and its device of ketone polymer waste liquid |
-
1952
- 1952-09-08 GB GB22531/52A patent/GB733650A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337632A (en) * | 1960-12-23 | 1967-08-22 | Hibernia Chemic G M B H | Process for recovering isophorone in high purity |
| US3337633A (en) * | 1960-12-31 | 1967-08-22 | Hibernia Chemie G M B H | Production of isophorone |
| EP0295361A3 (en) * | 1987-06-16 | 1990-01-24 | Union Camp Corporation | Preparation of pseudoionones |
| WO2012076317A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine |
| DE102010062587A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for the preparation of isophorone |
| WO2012076314A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Method for producing isophorone |
| DE102010062603A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine |
| CN102775287A (en) * | 2011-05-13 | 2012-11-14 | 赢创德固赛有限责任公司 | Process for preparing isophorone in the presence of at least one defoamer in the wastewater column in the workup section |
| DE102011075777A1 (en) | 2011-05-13 | 2012-11-15 | Evonik Degussa Gmbh | Process for the preparation of isophorone in the presence of at least one defoamer in the wastewater column in the workup part |
| WO2012156187A1 (en) | 2011-05-13 | 2012-11-22 | Evonik Degussa Gmbh | Process for preparing isophorone in the presence of at least one defoamer in the wastewater column in the workup section |
| US20140107379A1 (en) * | 2011-05-13 | 2014-04-17 | Evonik Degussa Gmbh | Process for preparing isophorone in the presence of at least one defoamer in the wastewater column in the workup section |
| US8884066B2 (en) * | 2011-05-13 | 2014-11-11 | Evonik Degussa Gmbh | Process for preparing isophorone in the presence of at least one defoamer in the wastewater column in the workup section |
| CN102775287B (en) * | 2011-05-13 | 2016-07-27 | 赢创德固赛有限责任公司 | The method preparing isophorone in post processing part in waste water tower in the case of there is at least one defoamer |
| CN108658737A (en) * | 2018-03-19 | 2018-10-16 | 江苏焕鑫新材料股份有限公司 | A kind of the deep pyrolytic resource utilization process and its device of ketone polymer waste liquid |
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