DE1112508B - Verfahren zur Aufrechterhaltung der katalytischen Wirksamkeit von Kobaltsalzen waehrend der Sauerstoff-oxydation von aromatischen Kohlen-wasserstoffen - Google Patents
Verfahren zur Aufrechterhaltung der katalytischen Wirksamkeit von Kobaltsalzen waehrend der Sauerstoff-oxydation von aromatischen Kohlen-wasserstoffenInfo
- Publication number
- DE1112508B DE1112508B DED27833A DED0027833A DE1112508B DE 1112508 B DE1112508 B DE 1112508B DE D27833 A DED27833 A DE D27833A DE D0027833 A DED0027833 A DE D0027833A DE 1112508 B DE1112508 B DE 1112508B
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- maintaining
- aqueous
- aromatic
- catalyst
- 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.)
- Pending
Links
- 230000003647 oxidation Effects 0.000 title claims description 30
- 238000007254 oxidation reaction Methods 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 11
- 239000001301 oxygen Substances 0.000 title claims description 11
- 229910052760 oxygen Inorganic materials 0.000 title claims description 11
- 230000003197 catalytic effect Effects 0.000 title claims description 5
- 150000001868 cobalt Chemical class 0.000 title claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- 239000012074 organic phase Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 235000010678 Paulownia tomentosa Nutrition 0.000 claims 1
- 240000002834 Paulownia tomentosa Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- 238000000605 extraction Methods 0.000 description 15
- 239000002574 poison Substances 0.000 description 12
- 231100000614 poison Toxicity 0.000 description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AXHVNJGQOJFMHT-UHFFFAOYSA-N 1-tert-butyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C(C)(C)C AXHVNJGQOJFMHT-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- BNGNANCNFVQZBM-UHFFFAOYSA-N cobalt;ethyl hexanoate Chemical compound [Co].CCCCCC(=O)OCC BNGNANCNFVQZBM-UHFFFAOYSA-N 0.000 description 2
- 229930007927 cymene Natural products 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- IQUZXHOQPNGXTM-UHFFFAOYSA-N 2,2-dimethylbutylbenzene Chemical compound CCC(C)(C)CC1=CC=CC=C1 IQUZXHOQPNGXTM-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 1
- 150000005199 trimethylbenzenes 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
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US816420XA | 1957-05-06 | 1957-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1112508B true DE1112508B (de) | 1961-08-10 |
Family
ID=22165440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED27833A Pending DE1112508B (de) | 1957-05-06 | 1958-04-08 | Verfahren zur Aufrechterhaltung der katalytischen Wirksamkeit von Kobaltsalzen waehrend der Sauerstoff-oxydation von aromatischen Kohlen-wasserstoffen |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1112508B (cs) |
| GB (1) | GB816420A (cs) |
| NL (2) | NL97742C (cs) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB757455A (en) * | 1953-07-20 | 1956-09-19 | Bataafsche Petroleum | A process for the separation of tertiary-alkyl-substituted benzoic acids from mixtures containing said acids |
| GB757658A (en) * | 1953-07-20 | 1956-09-19 | Bataafsche Petroleum | A process for separating tertiary-alkyl substituted benzoic acids from mixtures containing said acids |
-
0
- NL NL226688D patent/NL226688A/xx unknown
- NL NL97742D patent/NL97742C/xx active
-
1958
- 1958-03-05 GB GB7123/58A patent/GB816420A/en not_active Expired
- 1958-04-08 DE DED27833A patent/DE1112508B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB757455A (en) * | 1953-07-20 | 1956-09-19 | Bataafsche Petroleum | A process for the separation of tertiary-alkyl-substituted benzoic acids from mixtures containing said acids |
| GB757658A (en) * | 1953-07-20 | 1956-09-19 | Bataafsche Petroleum | A process for separating tertiary-alkyl substituted benzoic acids from mixtures containing said acids |
Also Published As
| Publication number | Publication date |
|---|---|
| NL226688A (cs) | |
| GB816420A (en) | 1959-07-15 |
| NL97742C (cs) |
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