DE2244872C3 - Verfahren zur Herstellung von niedrigmolekularen Carbonsäuren - Google Patents
Verfahren zur Herstellung von niedrigmolekularen CarbonsäurenInfo
- Publication number
- DE2244872C3 DE2244872C3 DE19722244872 DE2244872A DE2244872C3 DE 2244872 C3 DE2244872 C3 DE 2244872C3 DE 19722244872 DE19722244872 DE 19722244872 DE 2244872 A DE2244872 A DE 2244872A DE 2244872 C3 DE2244872 C3 DE 2244872C3
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- manganese
- oxygen
- carboxylic acids
- ppm
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000011572 manganese Substances 0.000 claims description 31
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 30
- 229910052748 manganese Inorganic materials 0.000 claims description 30
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 229910001882 dioxygen Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002697 manganese compounds Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 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 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 238000009835 boiling Methods 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 235000011054 acetic acid Nutrition 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002696 manganese Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 241000270295 Serpentes Species 0.000 description 1
- MOGGVIXWTIOANP-UHFFFAOYSA-N [O].OC=O Chemical compound [O].OC=O MOGGVIXWTIOANP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 aliphatic monocarboxylic acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4297071A GB1403196A (en) | 1971-09-15 | 1971-09-15 | Production of carboxylic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2244872A1 DE2244872A1 (de) | 1973-03-22 |
| DE2244872B2 DE2244872B2 (de) | 1979-12-13 |
| DE2244872C3 true DE2244872C3 (de) | 1980-08-21 |
Family
ID=10426771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722244872 Expired DE2244872C3 (de) | 1971-09-15 | 1972-09-13 | Verfahren zur Herstellung von niedrigmolekularen Carbonsäuren |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4836116A (enExample) |
| BE (1) | BE788783A (enExample) |
| CA (1) | CA976185A (enExample) |
| DE (1) | DE2244872C3 (enExample) |
| FR (1) | FR2152949B1 (enExample) |
| GB (1) | GB1403196A (enExample) |
| IT (1) | IT967473B (enExample) |
| NL (1) | NL7212456A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2961374D1 (en) * | 1978-01-27 | 1982-01-28 | Bp Chem Int Ltd | A method for increasing the selectivity to acetic acid in the production of a mixture of c1 to c3 monocarboxylic acids by oxidation of paraffinic hydrocarbons |
-
0
- BE BE788783D patent/BE788783A/xx unknown
-
1971
- 1971-09-15 GB GB4297071A patent/GB1403196A/en not_active Expired
-
1972
- 1972-09-13 DE DE19722244872 patent/DE2244872C3/de not_active Expired
- 1972-09-14 IT IT2920972A patent/IT967473B/it active
- 1972-09-14 FR FR7232543A patent/FR2152949B1/fr not_active Expired
- 1972-09-14 CA CA151,691A patent/CA976185A/en not_active Expired
- 1972-09-14 NL NL7212456A patent/NL7212456A/xx not_active Application Discontinuation
- 1972-09-14 JP JP9278872A patent/JPS4836116A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4836116A (enExample) | 1973-05-28 |
| IT967473B (it) | 1974-02-28 |
| BE788783A (fr) | 1973-03-13 |
| CA976185A (en) | 1975-10-14 |
| FR2152949A1 (enExample) | 1973-04-27 |
| GB1403196A (en) | 1975-08-28 |
| NL7212456A (enExample) | 1973-03-19 |
| FR2152949B1 (enExample) | 1976-05-21 |
| DE2244872B2 (de) | 1979-12-13 |
| DE2244872A1 (de) | 1973-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |