GB1259145A - - Google Patents
Info
- Publication number
- GB1259145A GB1259145A GB1259145DA GB1259145A GB 1259145 A GB1259145 A GB 1259145A GB 1259145D A GB1259145D A GB 1259145DA GB 1259145 A GB1259145 A GB 1259145A
- Authority
- GB
- United Kingdom
- Prior art keywords
- palladium
- butene
- oct
- contacting
- methyl ethyl
- 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- -1 halogen ion Chemical class 0.000 abstract 2
- 238000006317 isomerization reaction Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- 150000002941 palladium compounds Chemical class 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- 150000005309 metal halides Chemical class 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000002940 palladium Chemical class 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 235000011164 potassium chloride Nutrition 0.000 abstract 1
- 239000001103 potassium chloride Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
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)
Abstract
1,259,145. Methyl ethyl ketone. MARUZEN OIL CO. Ltd. 14 Oct., 1969 [14 Oct., 1968], No. 50541/69. Heading C2C. Methyl ethyl ketone is prepared by contacting a C 4 -hydrocarbon mixture containing 1-butene with an isomerization catalyst capable of producing double-bond migration, at a temperature of from 0‹ to 300‹ C. under a pressure of from atmospheric to 50 atmospheres and contacting the C 4 -hydrocarbon mixture rich in 2-butene so obtained with an aqueous catalytic solution containing a water-soluble palladium compound and ferric sulphate. The palladium compound is suitably an inorganic palladium salt such as the sulphate, nitrate or chloride or may be palladium potassium chloride, whereas the isomerization catalyst is suitably sodium, lithium, platinum, nickel or palladium, a portion of the latter preferably being sulphurized. The carbonyl reaction is preferably carried out at from room temperature to 200‹ C. under a pressure sufficient to maintain at least the aqueous solution in the liquid phase. The aqueous solution may additionally contain a halogen ion, e.g. chlorine supplied by, e.g. including a metal halide or a hydrogen halide in this solution. Examples describe the preparation of MEK, the principal by-product being t - butanol together with smaller amounts of see-butanol, n-butyraldehyde, acetone and 3-chlorobutanone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7483268 | 1968-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1259145A true GB1259145A (en) | 1972-01-05 |
Family
ID=13558685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1259145D Expired GB1259145A (en) | 1968-10-14 | 1969-10-14 |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1951759A1 (en) |
| GB (1) | GB1259145A (en) |
| NL (1) | NL6915556A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481373A (en) * | 1981-07-01 | 1984-11-06 | Toa Nenryo Kogyo Kabushiki Kaisha | Method of manufacturing ketones |
| US4720474A (en) * | 1985-09-24 | 1988-01-19 | Catalytica Associates | Olefin oxidation catalyst system |
| US4723041A (en) * | 1985-09-24 | 1988-02-02 | Catalytica Associates | Olefin oxidation catalyst system |
| CN109761841A (en) * | 2019-01-30 | 2019-05-17 | 上海阿拉丁生化科技股份有限公司 | A kind of preparation process of order of spectrum formamide |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102011075730A1 (en) | 2011-05-12 | 2012-11-15 | Schaeffler Technologies AG & Co. KG | radial bearings |
-
1969
- 1969-10-14 NL NL6915556A patent/NL6915556A/xx unknown
- 1969-10-14 GB GB1259145D patent/GB1259145A/en not_active Expired
- 1969-10-14 DE DE19691951759 patent/DE1951759A1/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481373A (en) * | 1981-07-01 | 1984-11-06 | Toa Nenryo Kogyo Kabushiki Kaisha | Method of manufacturing ketones |
| US4720474A (en) * | 1985-09-24 | 1988-01-19 | Catalytica Associates | Olefin oxidation catalyst system |
| US4723041A (en) * | 1985-09-24 | 1988-02-02 | Catalytica Associates | Olefin oxidation catalyst system |
| CN109761841A (en) * | 2019-01-30 | 2019-05-17 | 上海阿拉丁生化科技股份有限公司 | A kind of preparation process of order of spectrum formamide |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6915556A (en) | 1970-04-16 |
| DE1951759A1 (en) | 1970-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |