DE2314454C2 - Verfahren zur kontinuierlichen Herstellung von Carbonsäuren - Google Patents
Verfahren zur kontinuierlichen Herstellung von CarbonsäurenInfo
- Publication number
- DE2314454C2 DE2314454C2 DE2314454A DE2314454A DE2314454C2 DE 2314454 C2 DE2314454 C2 DE 2314454C2 DE 2314454 A DE2314454 A DE 2314454A DE 2314454 A DE2314454 A DE 2314454A DE 2314454 C2 DE2314454 C2 DE 2314454C2
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- oxidation
- carboxylic acids
- catalyst
- reaction
- 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 23
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 16
- 238000010924 continuous production Methods 0.000 title claims description 7
- 150000002009 diols Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 238000007254 oxidation reaction Methods 0.000 claims description 32
- 230000003647 oxidation Effects 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 229910001385 heavy metal Inorganic materials 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 4
- 229940070765 laurate Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000007248 oxidative elimination reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- -1 oxides Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003568 thioethers Chemical class 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
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
-
- 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
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/245—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of keto groups or secondary alcohol 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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2314454A DE2314454C2 (de) | 1973-03-23 | 1973-03-23 | Verfahren zur kontinuierlichen Herstellung von Carbonsäuren |
| NL7402466A NL7402466A (enExample) | 1973-03-23 | 1974-02-22 | |
| FR7409723A FR2222348B1 (enExample) | 1973-03-23 | 1974-03-21 | |
| IT67866/74A IT1009346B (it) | 1973-03-23 | 1974-03-21 | Procedimento per la produzione con tinua di acidi carbossilici |
| US05/453,505 US4006173A (en) | 1973-03-23 | 1974-03-21 | Process for continuous preparation of carboxylic acids |
| BE142259A BE812615A (fr) | 1973-03-23 | 1974-03-21 | Procede de preparation continue d'acides carboxyliques |
| GB1281174A GB1450248A (en) | 1973-03-23 | 1974-03-22 | Process for the contininuous preparation of carboxylic acids |
| JP49031597A JPS5756457B2 (enExample) | 1973-03-23 | 1974-03-22 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2314454A DE2314454C2 (de) | 1973-03-23 | 1973-03-23 | Verfahren zur kontinuierlichen Herstellung von Carbonsäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2314454A1 DE2314454A1 (de) | 1974-10-03 |
| DE2314454C2 true DE2314454C2 (de) | 1987-04-23 |
Family
ID=5875628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2314454A Expired DE2314454C2 (de) | 1973-03-23 | 1973-03-23 | Verfahren zur kontinuierlichen Herstellung von Carbonsäuren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4006173A (enExample) |
| JP (1) | JPS5756457B2 (enExample) |
| BE (1) | BE812615A (enExample) |
| DE (1) | DE2314454C2 (enExample) |
| FR (1) | FR2222348B1 (enExample) |
| GB (1) | GB1450248A (enExample) |
| IT (1) | IT1009346B (enExample) |
| NL (1) | NL7402466A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61244701A (ja) * | 1985-04-09 | 1986-10-31 | 財団法人 雑賀技術研究所 | 粉粒物の計量包装装置 |
| FR2994178B1 (fr) * | 2012-07-31 | 2015-08-07 | Interoleagineuse D Assistance Et De Dev S I A Soc | Procede de preparation d'un acide carboxylique ou d'un aldehyde |
| FR3015480A1 (fr) * | 2013-12-24 | 2015-06-26 | Interoleagineuse D Assistance Et De Dev S I A Soc | Procede de preparation d'un acide carboxylique. |
| EP4382529A1 (en) | 2022-12-07 | 2024-06-12 | Bayer Consumer Care AG | A process for preparing pure (3s)-pyrrolidin-3-ol and pure (3s)-pyrrolidin-3-ol hydrochloride |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2086521A5 (en) * | 1970-04-01 | 1971-12-31 | Air Liquide | Carboxylic acids prepn by oxidative cleavage of alpha-glycols |
| US3855257A (en) * | 1970-06-29 | 1974-12-17 | Procter & Gamble | Preparation of carboxylic acids by the oxidation of vicinal glycols |
| DE2038296A1 (de) * | 1970-08-01 | 1972-02-17 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Carbonsaeuren |
| US3711523A (en) * | 1970-09-04 | 1973-01-16 | Procter & Gamble | Oxidation of vicinal glycols in the presence of organic peroxides and cobaltous compounds |
| NL7109931A (enExample) * | 1970-10-28 | 1972-05-03 |
-
1973
- 1973-03-23 DE DE2314454A patent/DE2314454C2/de not_active Expired
-
1974
- 1974-02-22 NL NL7402466A patent/NL7402466A/xx not_active Application Discontinuation
- 1974-03-21 BE BE142259A patent/BE812615A/xx not_active IP Right Cessation
- 1974-03-21 IT IT67866/74A patent/IT1009346B/it active
- 1974-03-21 FR FR7409723A patent/FR2222348B1/fr not_active Expired
- 1974-03-21 US US05/453,505 patent/US4006173A/en not_active Expired - Lifetime
- 1974-03-22 GB GB1281174A patent/GB1450248A/en not_active Expired
- 1974-03-22 JP JP49031597A patent/JPS5756457B2/ja not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1009346B (it) | 1976-12-10 |
| JPS5756457B2 (enExample) | 1982-11-30 |
| JPS49135908A (enExample) | 1974-12-27 |
| BE812615A (fr) | 1974-09-23 |
| FR2222348A1 (enExample) | 1974-10-18 |
| FR2222348B1 (enExample) | 1976-06-25 |
| US4006173A (en) | 1977-02-01 |
| NL7402466A (enExample) | 1974-09-25 |
| GB1450248A (en) | 1976-09-22 |
| DE2314454A1 (de) | 1974-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |