GB1298326A - Process for the production of 2-methylene-1,3-diacetoxypropane - Google Patents
Process for the production of 2-methylene-1,3-diacetoxypropaneInfo
- Publication number
- GB1298326A GB1298326A GB818170A GB818170A GB1298326A GB 1298326 A GB1298326 A GB 1298326A GB 818170 A GB818170 A GB 818170A GB 818170 A GB818170 A GB 818170A GB 1298326 A GB1298326 A GB 1298326A
- Authority
- GB
- United Kingdom
- Prior art keywords
- palladium
- acetate
- acetyl acetonate
- feb
- acetyl
- 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
- FKAKGSJLTBVQOP-UHFFFAOYSA-N 2-(acetyloxymethyl)prop-2-enyl acetate Chemical compound CC(=O)OCC(=C)COC(C)=O FKAKGSJLTBVQOP-UHFFFAOYSA-N 0.000 title abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000000377 silicon dioxide Substances 0.000 abstract 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 abstract 1
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 abstract 1
- IVKYUXHYUAMPMT-UHFFFAOYSA-N 2-methylprop-2-enyl acetate Chemical compound CC(=C)COC(C)=O IVKYUXHYUAMPMT-UHFFFAOYSA-N 0.000 abstract 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal acetate Chemical class 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052737 gold Inorganic materials 0.000 abstract 1
- 239000010931 gold Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 238000005470 impregnation Methods 0.000 abstract 1
- 229910052741 iridium Inorganic materials 0.000 abstract 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 abstract 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 235000011056 potassium acetate Nutrition 0.000 abstract 1
- 239000008262 pumice Substances 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 150000004760 silicates Chemical class 0.000 abstract 1
- 239000011949 solid catalyst Substances 0.000 abstract 1
- 229910052566 spinel group Inorganic materials 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
- 239000010937 tungsten Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8946—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali or alkaline earth metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691909964 DE1909964C3 (de) | 1969-02-27 | 1969-02-27 | Verfahren zur Herstellung von 2 Methylen 1,3 diacetoxy propan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1298326A true GB1298326A (en) | 1972-11-29 |
Family
ID=5726560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB818170A Expired GB1298326A (en) | 1969-02-27 | 1970-02-20 | Process for the production of 2-methylene-1,3-diacetoxypropane |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS54886B1 (enExample) |
| AT (1) | AT292654B (enExample) |
| BE (1) | BE746642A (enExample) |
| DE (1) | DE1909964C3 (enExample) |
| FR (1) | FR2033154A5 (enExample) |
| GB (1) | GB1298326A (enExample) |
| NL (1) | NL7002355A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110891928A (zh) * | 2017-07-24 | 2020-03-17 | 株式会社可乐丽 | 双酰氧基化外向亚甲基化合物的制造方法 |
| CN112341314A (zh) * | 2020-11-11 | 2021-02-09 | 北京水木滨华科技有限公司 | 一种由异丁烯制备2-甲基-1,3-丙二醇的方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3243545A1 (de) * | 1982-11-25 | 1984-05-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1,3-diacetoxy-2-methylenpropan |
| JP7291141B2 (ja) | 2018-07-27 | 2023-06-14 | 株式会社クラレ | １，３－ビスアシルオキシ－２－メチレンプロパンの製造方法 |
-
1969
- 1969-02-27 DE DE19691909964 patent/DE1909964C3/de not_active Expired
-
1970
- 1970-02-19 AT AT152470A patent/AT292654B/de not_active IP Right Cessation
- 1970-02-19 NL NL7002355A patent/NL7002355A/xx unknown
- 1970-02-20 GB GB818170A patent/GB1298326A/en not_active Expired
- 1970-02-25 JP JP1561570A patent/JPS54886B1/ja active Pending
- 1970-02-27 FR FR7007264A patent/FR2033154A5/fr not_active Expired
- 1970-02-27 BE BE746642D patent/BE746642A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110891928A (zh) * | 2017-07-24 | 2020-03-17 | 株式会社可乐丽 | 双酰氧基化外向亚甲基化合物的制造方法 |
| US10843998B2 (en) * | 2017-07-24 | 2020-11-24 | Kuraray Co., Ltd. | Method for producing bis-acyloxylated exomethylene compound |
| TWI781198B (zh) * | 2017-07-24 | 2022-10-21 | 日商可樂麗股份有限公司 | 雙醯氧基化外亞甲基化合物之製造方法 |
| CN112341314A (zh) * | 2020-11-11 | 2021-02-09 | 北京水木滨华科技有限公司 | 一种由异丁烯制备2-甲基-1,3-丙二醇的方法 |
| CN112341314B (zh) * | 2020-11-11 | 2021-11-02 | 北京水木滨华科技有限公司 | 一种由异丁烯制备2-甲基-1,3-丙二醇的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1909964B2 (de) | 1973-02-22 |
| BE746642A (fr) | 1970-08-27 |
| NL7002355A (enExample) | 1970-08-31 |
| FR2033154A5 (enExample) | 1970-11-27 |
| JPS54886B1 (enExample) | 1979-01-18 |
| DE1909964A1 (de) | 1970-09-17 |
| AT292654B (de) | 1971-09-10 |
| DE1909964C3 (de) | 1973-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 48S | Specification amended (sect. 8/1949) | ||
| SPA | Amended specification published | ||
| PCNP | Patent ceased through non-payment of renewal fee |