DE1518876C3 - Verfahren zur oxydativen Umwandlung von Olefinen in der flüssigen Phase in Gegenwart einer Palladiumsalze enthaltenden Katalysatorlösung - Google Patents
Verfahren zur oxydativen Umwandlung von Olefinen in der flüssigen Phase in Gegenwart einer Palladiumsalze enthaltenden KatalysatorlösungInfo
- Publication number
- DE1518876C3 DE1518876C3 DE1518876A DE1518876A DE1518876C3 DE 1518876 C3 DE1518876 C3 DE 1518876C3 DE 1518876 A DE1518876 A DE 1518876A DE 1518876 A DE1518876 A DE 1518876A DE 1518876 C3 DE1518876 C3 DE 1518876C3
- Authority
- DE
- Germany
- Prior art keywords
- palladium
- weight
- chloride
- copper
- olefins
- 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
- 238000006243 chemical reaction Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 11
- 150000002940 palladium Chemical class 0.000 title claims 10
- 239000003054 catalyst Substances 0.000 title claims 9
- 150000001336 alkenes Chemical class 0.000 title claims 7
- 230000001590 oxidative effect Effects 0.000 title claims 4
- 239000007791 liquid phase Substances 0.000 title claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000008262 pumice Substances 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 11
- -1 palladium salt chloride Chemical class 0.000 claims 8
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 7
- 229910052763 palladium Inorganic materials 0.000 claims 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 230000002787 reinforcement Effects 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000005995 Aluminium silicate Substances 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 235000012211 aluminium silicate Nutrition 0.000 claims 1
- 239000010425 asbestos Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 229910052914 metal silicate Inorganic materials 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 229910052895 riebeckite Inorganic materials 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 150000004760 silicates Chemical class 0.000 claims 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims 1
- 229910010271 silicon carbide Inorganic materials 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 229910052596 spinel Inorganic materials 0.000 claims 1
- 239000011029 spinel Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 229920001567 vinyl ester resin Polymers 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0047365 | 1965-10-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1518876A1 DE1518876A1 (de) | 1969-07-31 |
| DE1518876B2 DE1518876B2 (de) | 1974-02-28 |
| DE1518876C3 true DE1518876C3 (de) | 1974-10-03 |
Family
ID=7101583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1518876A Expired DE1518876C3 (de) | 1965-10-07 | 1965-10-07 | Verfahren zur oxydativen Umwandlung von Olefinen in der flüssigen Phase in Gegenwart einer Palladiumsalze enthaltenden Katalysatorlösung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS507051B1 (enExample) |
| AT (1) | AT266804B (enExample) |
| BE (1) | BE687943A (enExample) |
| CH (1) | CH503677A (enExample) |
| DE (1) | DE1518876C3 (enExample) |
| ES (1) | ES331874A1 (enExample) |
| FR (1) | FR1496043A (enExample) |
| GB (1) | GB1158706A (enExample) |
| NL (1) | NL6613753A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57122043A (en) * | 1981-01-23 | 1982-07-29 | Ube Ind Ltd | Preparation of oxalic acid diester |
-
1965
- 1965-10-07 DE DE1518876A patent/DE1518876C3/de not_active Expired
-
1966
- 1966-09-29 NL NL6613753A patent/NL6613753A/xx unknown
- 1966-10-04 CH CH1427766A patent/CH503677A/de not_active IP Right Cessation
- 1966-10-04 ES ES0331874A patent/ES331874A1/es not_active Expired
- 1966-10-05 AT AT933966A patent/AT266804B/de active
- 1966-10-06 GB GB44635/66A patent/GB1158706A/en not_active Expired
- 1966-10-06 JP JP41065454A patent/JPS507051B1/ja active Pending
- 1966-10-07 FR FR79152A patent/FR1496043A/fr not_active Expired
- 1966-10-07 BE BE687943D patent/BE687943A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1518876B2 (de) | 1974-02-28 |
| GB1158706A (en) | 1969-07-16 |
| DE1518876A1 (de) | 1969-07-31 |
| CH503677A (de) | 1971-02-28 |
| ES331874A1 (es) | 1967-10-01 |
| JPS507051B1 (enExample) | 1975-03-20 |
| NL6613753A (enExample) | 1967-04-10 |
| FR1496043A (fr) | 1967-09-22 |
| BE687943A (enExample) | 1967-04-07 |
| AT266804B (de) | 1968-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |