GB601922A - Improvements in and relating to the preparation of methyl vinyl ketone - Google Patents
Improvements in and relating to the preparation of methyl vinyl ketoneInfo
- Publication number
- GB601922A GB601922A GB2688445A GB2688445A GB601922A GB 601922 A GB601922 A GB 601922A GB 2688445 A GB2688445 A GB 2688445A GB 2688445 A GB2688445 A GB 2688445A GB 601922 A GB601922 A GB 601922A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silicate
- aluminium
- levulinic acid
- preparation
- passing
- 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
- FUSUHKVFWTUUBE-UHFFFAOYSA-N Methyl vinyl ketone Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- JLDSOYXADOWAKB-UHFFFAOYSA-N Aluminium nitrate Chemical compound [Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JLDSOYXADOWAKB-UHFFFAOYSA-N 0.000 abstract 4
- JOOXCMJARBKPKM-UHFFFAOYSA-N Levulinic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 abstract 4
- 229940040102 levulinic acid Drugs 0.000 abstract 4
- 239000000377 silicon dioxide Substances 0.000 abstract 4
- 239000005995 Aluminium silicate Substances 0.000 abstract 3
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 abstract 3
- 235000012211 aluminium silicate Nutrition 0.000 abstract 3
- 229910000323 aluminium silicate Inorganic materials 0.000 abstract 3
- 229910052911 sodium silicate Inorganic materials 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- QOTQFLOTGBBMEX-UHFFFAOYSA-N α-angelica lactone Chemical compound CC1=CCC(=O)O1 QOTQFLOTGBBMEX-UHFFFAOYSA-N 0.000 abstract 3
- 239000004115 Sodium Silicate Substances 0.000 abstract 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N Sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K Aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 abstract 1
- 229940001007 aluminium phosphate Drugs 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052593 corundum Inorganic materials 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000011259 mixed solution Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008262 pumice Substances 0.000 abstract 1
- 229910052904 quartz Inorganic materials 0.000 abstract 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N silicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 235000019795 sodium metasilicate Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
- BGLUXFNVVSVEET-UHFFFAOYSA-N β-angelica lactone Chemical compound CC1OC(=O)C=C1 BGLUXFNVVSVEET-UHFFFAOYSA-N 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
- C07C45/673—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 change of size of the carbon skeleton
- C07C45/676—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 change of size of the carbon skeleton by elimination of carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The Provisional Specification describes the preparation of aluminium silicate comprising mixing solutions of sodium hydroxide and sodium silicate in amounts such that the silicate conforms to Na2SiO3 and adding the mixture to a solution of aluminium nitrate in amounts such that the ratio of Al2O3 to SiO2 is 1 : 1. The compound is a catalyst for the conversion of levulinic acid or its esters to methyl vinyl ketone (see Group IV (b)).ALSO:Methyl vinyl ketone is produced by heating alpha or beta angelica lactone or levulinic acid or an ester thereof in the vapour phase at a temperature of from 450 DEG to 650 DEG C. The reaction may be carried out in a vessel packed with filling bodies such as silica chips or pumice, in the presence of a dehydrating or cracking catalyst such as aluminium silicate or in an unpacked vessel. If desired, angelica lactone may be prepared in situ and the process then carried out in several stages. In examples, the ketone is prepared (1) by passing alpha angelica lactone or levulinic acid over silica chips at 570 DEG C.; (2) by passing levulinic acid over basic aluminium phosphate at 350 DEG -360 DEG C. and then passing the exit vapours over heated silica chips as in (1). Specification 453,518 is referred to. The processes described in the Provisional Specifications are not limited to the use of the above temperatures; both Specifications describe the preparation of the abovementioned aluminium silicate comprising heating a mixed solution of sodium hydroxide and sodium silicate with a solution of aluminium nitrate (see Group III).
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB601922A true GB601922A (en) | 1948-05-14 |
Family
ID=1740287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2688445A Expired GB601922A (en) | 1945-10-15 | Improvements in and relating to the preparation of methyl vinyl ketone |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB601922A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7960592B1 (en) * | 2010-01-12 | 2011-06-14 | Wisconsin Alumni Research Foundation | Production of methyl-vinyl ketone from levulinic acid |
| WO2015144994A1 (en) | 2014-03-26 | 2015-10-01 | Neste Oil Oyj | Method for thermal conversion of ketoacids and hydrotreatment to hydrocarbons |
| US10538473B2 (en) | 2014-03-26 | 2020-01-21 | Neste Oyj | Method for catalytic conversion of ketoacids and hydrotreament to hydrocarbons |
-
1945
- 1945-10-15 GB GB2688445A patent/GB601922A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7960592B1 (en) * | 2010-01-12 | 2011-06-14 | Wisconsin Alumni Research Foundation | Production of methyl-vinyl ketone from levulinic acid |
| WO2011087962A1 (en) * | 2010-01-12 | 2011-07-21 | Wisconsin Alumni Research Foundation | Production of methyl-vinyl ketone from levulinic acid |
| CN102686549A (en) * | 2010-01-12 | 2012-09-19 | 威斯康星旧生研究基金会 | Production of methyl-vinyl ketone from levulinic acid |
| CN102686549B (en) * | 2010-01-12 | 2015-06-17 | 威斯康星旧生研究基金会 | Production of methyl-vinyl ketone from levulinic acid |
| WO2015144994A1 (en) | 2014-03-26 | 2015-10-01 | Neste Oil Oyj | Method for thermal conversion of ketoacids and hydrotreatment to hydrocarbons |
| EP3132005A4 (en) * | 2014-03-26 | 2018-03-14 | Neste Oil Oyj | Method for thermal conversion of ketoacids and hydrotreatment to hydrocarbons |
| US10364396B2 (en) | 2014-03-26 | 2019-07-30 | Neste Oyj | Method for thermal conversion of ketoacids and hydrotreament to hydrocarbons |
| US10538473B2 (en) | 2014-03-26 | 2020-01-21 | Neste Oyj | Method for catalytic conversion of ketoacids and hydrotreament to hydrocarbons |
| US10550062B2 (en) | 2014-03-26 | 2020-02-04 | Neste Oyj | Method for catalytic conversion of ketoacids and hydrotreament to hydrocarbons |
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