GB662139A - Improvements relating to the oxidation of aromatic side-chain compounds - Google Patents
Improvements relating to the oxidation of aromatic side-chain compoundsInfo
- Publication number
- GB662139A GB662139A GB24877/48A GB2487748A GB662139A GB 662139 A GB662139 A GB 662139A GB 24877/48 A GB24877/48 A GB 24877/48A GB 2487748 A GB2487748 A GB 2487748A GB 662139 A GB662139 A GB 662139A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- oxidation
- compounds
- pressure
- atmospheres
- 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
- 230000003647 oxidation Effects 0.000 title abstract 6
- 238000007254 oxidation reaction Methods 0.000 title abstract 6
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 125000003118 aryl group Chemical group 0.000 title 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 229910017604 nitric acid Inorganic materials 0.000 abstract 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 2
- 229940078552 o-xylene Drugs 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 abstract 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 abstract 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical class OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 abstract 1
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical class OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 abstract 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 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
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C07C51/275—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of 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)
Abstract
Aromatic compounds are oxidized with nitric acid of 10 to 35 per cent strength above 150 DEG C., the side chains being converted into carboxyl groups, the pressure being at least 15 atmospheres for compounds with one oxidizable side-chain and at least 25 atmospheres for compounds with a plurality of oxidizable side-chains. The preferred temperature range is 165 DEG to 220 DEG C. and the preferred pressure ranges 30 to 50 and 50 to 100 atmospheres for the oxidation of one or more side chains respectively. The more dilute acid may be used in excess of the theoretical amount but with acid of higher concentration the quantity is preferably reduced to not more than theoretical. To avoid corrosion and formation of by-products, the nitric acid should be consumed as quickly as possible, e.g. by using excess of the aromatic compound and adding the necessary acid in portions at intervals. Alternatively, the mixture of reactants in the correct proportion may be introduced into the autoclave a portion at a time, and in this way the process may be operated continuously, the gases being discharged continuously or intermittently to maintain the pressure at a safe value. The process is applicable to aromatic hydrocarbons with one or more side-chains, and to their substitution derivatives, e.g. chloro and nitro compounds, which give chlorocarboxylic and nitrocarboxylic acids respectively. The examples describe the batchwise oxidation of p-xylene to terephthalic acid and the three nitrotoluenes to nitrobenzoic acids, some picric acid being obtained from o-nitrotoluene. The continuous oxidation of toluene is also described, the products being benzoic and p-nitrobenzoic acids; a method is given for the separation of these. Chlorotoluenes, o-xylene and p-cymene are also specified as starting materials. German Specification 216,091 and U.S.A. Specification 1,576,999 are referred to. In the Specification as open to inspection under Sect. 91, it is stated that concentrated nitric acid may be used in excess of the theoretical amount, when nitration occurs in addition to oxidation; the use of 50 per cent acid is mentioned. The operating pressure may be any superatmospheric pressure. Further examples are given of the oxidation of o-xylene to phthalic acid, p-cymene to terephthalic acid and the three chlorotoluenes to the corresponding chlorobenzoic acids. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE662139X | 1947-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB662139A true GB662139A (en) | 1951-12-05 |
Family
ID=20314366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24877/48A Expired GB662139A (en) | 1947-09-27 | 1948-09-23 | Improvements relating to the oxidation of aromatic side-chain compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB662139A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1035642B (en) * | 1954-10-06 | 1958-08-07 | California Research Corp | Process for the preparation of benzene polycarboxylic acids |
| DE1081878B (en) * | 1955-09-22 | 1960-05-19 | Wilhelm Schemuth | Process for the production of terephthalic acid by the oxidation of p-ethyltoluene |
| DE1136688B (en) * | 1957-02-09 | 1962-09-20 | Robert Sancier Aries | Process for the preparation of benzene dicarboxylic acids |
| US3299126A (en) * | 1962-09-04 | 1967-01-17 | Minnesota Mining & Mfg | Process for oxidizing quinodimethanes to form aromatic carboxylic acids |
| EP1205466A1 (en) * | 2000-11-13 | 2002-05-15 | Atofina | Process for the synthesis of carboxy-2-anthraquinone by nitric oxidation of ethyl-2-anthraquinone |
-
1948
- 1948-09-23 GB GB24877/48A patent/GB662139A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1035642B (en) * | 1954-10-06 | 1958-08-07 | California Research Corp | Process for the preparation of benzene polycarboxylic acids |
| DE1081878B (en) * | 1955-09-22 | 1960-05-19 | Wilhelm Schemuth | Process for the production of terephthalic acid by the oxidation of p-ethyltoluene |
| DE1136688B (en) * | 1957-02-09 | 1962-09-20 | Robert Sancier Aries | Process for the preparation of benzene dicarboxylic acids |
| US3299126A (en) * | 1962-09-04 | 1967-01-17 | Minnesota Mining & Mfg | Process for oxidizing quinodimethanes to form aromatic carboxylic acids |
| EP1205466A1 (en) * | 2000-11-13 | 2002-05-15 | Atofina | Process for the synthesis of carboxy-2-anthraquinone by nitric oxidation of ethyl-2-anthraquinone |
| FR2816615A1 (en) * | 2000-11-13 | 2002-05-17 | Atofina | PROCESS FOR THE SYNTHESIS OF CARBOXY-2-ANTHRAQUINONE BY NITRIC OXIDATION OF ALKYL-2-ANTHRAQUINONE |
| US6509486B2 (en) | 2000-11-13 | 2003-01-21 | Atofina | Process for the synthesis of 2-carboxyanthraquinone by oxidation of 2-ethylanthraquinone with nitric acid |
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