CN103073461A - Method for preparing 2-nitro-4-methylsulfonylbenzoic acid by high-valence V (vanadium) complex catalytic system - Google Patents
Method for preparing 2-nitro-4-methylsulfonylbenzoic acid by high-valence V (vanadium) complex catalytic system Download PDFInfo
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- CN103073461A CN103073461A CN2013100114455A CN201310011445A CN103073461A CN 103073461 A CN103073461 A CN 103073461A CN 2013100114455 A CN2013100114455 A CN 2013100114455A CN 201310011445 A CN201310011445 A CN 201310011445A CN 103073461 A CN103073461 A CN 103073461A
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- nitryl
- nitro
- benzoic acid
- thiamphenicol benzoic
- vanadium
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- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 229910052720 vanadium Inorganic materials 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000003197 catalytic effect Effects 0.000 title abstract description 5
- QNOUABMNRMROSL-UHFFFAOYSA-N 110964-79-9 Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QNOUABMNRMROSL-UHFFFAOYSA-N 0.000 title abstract 8
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 74
- 229960003053 thiamphenicol Drugs 0.000 claims description 50
- 235000010233 benzoic acid Nutrition 0.000 claims description 48
- 239000005711 Benzoic acid Substances 0.000 claims description 37
- 238000010438 heat treatment Methods 0.000 claims description 12
- 229910017604 nitric acid Inorganic materials 0.000 claims description 11
- OXBDLEXAVKAJFD-UHFFFAOYSA-N 1-methyl-4-methylsulfonyl-2-nitrobenzene Chemical compound CC1=CC=C(S(C)(=O)=O)C=C1[N+]([O-])=O OXBDLEXAVKAJFD-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 6
- 230000004913 activation Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000011365 complex material Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- DFSXBQXKFMUNCI-UHFFFAOYSA-N CCC(C)OC(c1ccc(C)cc1[N+]([O-])=O)OC Chemical compound CCC(C)OC(c1ccc(C)cc1[N+]([O-])=O)OC DFSXBQXKFMUNCI-UHFFFAOYSA-N 0.000 description 1
- 0 CCOC(c1ccc(*(C)C)cc1[N+]([O-])=O)=O Chemical compound CCOC(c1ccc(*(C)C)cc1[N+]([O-])=O)=O 0.000 description 1
- NSCFGVZGQSHJKZ-UHFFFAOYSA-N CS(c1cc([N+]([O-])=O)c(C(O)O)cc1)(=O)=O Chemical compound CS(c1cc([N+]([O-])=O)c(C(O)O)cc1)(=O)=O NSCFGVZGQSHJKZ-UHFFFAOYSA-N 0.000 description 1
- CJVACYDFVBINGD-UHFFFAOYSA-N Cc(cc1)cc([N+]([O-])=O)c1C(OC)=O Chemical compound Cc(cc1)cc([N+]([O-])=O)c1C(OC)=O CJVACYDFVBINGD-UHFFFAOYSA-N 0.000 description 1
- 239000005578 Mesotrione Substances 0.000 description 1
- VFGRVPOWXBYJFQ-UHFFFAOYSA-N benzoic acid;vanadium Chemical compound [V].OC(=O)C1=CC=CC=C1 VFGRVPOWXBYJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006561 solvent free reaction Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000006273 synthetic pesticide Substances 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a method for preparing a 2-nitro-4-methylsulfonylbenzoic acid by a high-valence vanadium complex catalytic system. The method comprises steps as follows: dissolving V2O5 into a sulfuric acid solution, adding the 2-Nitro-4-methylsulfonylbenzoic acid for reaction, and obtaining a 2-Nitro-4-methylsulfonylbenzoic acid V complex; and dissolving the obtained 2-Nitro-4-methylsulfonylbenzoic acid V complex into a 2-Nitro-4-methylsulfonylbenzoic acid system, dropwise adding nitric acids for catalytic oxidation reaction, and preparing the 2-Nitro-4-methylsulfonylbenzoic acid. According to the method, as the high-valence V complex and raw materials form a Pi activation center more easily, the V catalytic activity is improved, the V usage amount is greatly reduced, the usage amount of the high-valence V is 0.2% to 1% of that of the raw materials, and solvent concentrated sulfuric acids are not used when the 2-Nitro-4-methylsulfonylbenzoic acid are oxidized, so that solvent-free synthesis is achieved.
Description
Technical field
The present invention relates to the method that a kind of high price vanadium complex catalyst system prepares the 2-nitryl-4-thiamphenicol benzoic acid, a kind of oxidation 2-nitro-4-methylsulfonyltoluene prepares the method for 2-nitryl-4-thiamphenicol benzoic acid.
Background technology
The 2-nitryl-4-thiamphenicol benzoic acid is a kind of important intermediate of synthetic pesticide mesotrione, and is widely used in dyestuff, medicine and other fields, has sizable using value.The production technique of 2-nitryl-4-thiamphenicol benzoic acid is take 2-nitro-4-methylsulfonyltoluene as raw material at present, makes through the strong oxidizer oxidation.Patent documentation US5424481 has introduced in the presence of Vanadium Pentoxide in FLAKES, prepares the method for 2-nitryl-4-thiamphenicol benzoic acid with nitric acid oxidation, and productive rate is more than 80%.This method uses vitriol oil as solvent, uses the poisonous reagent Vanadium Pentoxide in FLAKES to be catalyzer, and the consumption of Vanadium Pentoxide in FLAKES is about 5-10%, and there is the cost recovery height of Vanadium Pentoxide in FLAKES in this technique, and to problems such as environment are unfriendly, so industrial applications is restricted.
Summary of the invention
The present invention is intended to propose a kind of vitriol oil that do not need and makes solvent, and a kind of high price vanadium complex catalyst system prepares the method for 2-nitryl-4-thiamphenicol benzoic acid.
The method that this high price vanadium complex catalyst system prepares the 2-nitryl-4-thiamphenicol benzoic acid forms title complex with Vanadium Pentoxide in FLAKES and product 2-nitryl-4-thiamphenicol benzoic acid, title complex is dissolved in the 2-nitro of heating and melting-4-methylsulfonyltoluene makes catalyzer, use nitric acid as oxidant, make the 2-nitryl-4-thiamphenicol benzoic acid, the steps include:
(1) with V
2O
5Add 2-nitryl-4-thiamphenicol benzoic acid reacting by heating in hydrothermal reaction kettle after being dissolved in a small amount of concentrated sulfuric acid solution, obtain high price vanadium complex crystal;
(2) with the high price vanadium complex crystal of gained of upper step, be dissolved in the 2-nitro of melting-4-methylsulfonyltoluene, be added dropwise to again nitric acid and carry out oxidizing reaction, make the 2-nitryl-4-thiamphenicol benzoic acid.
Method of the present invention is because first with Vanadium Pentoxide in FLAKES and the synthetic high price of 2-nitryl-4-thiamphenicol benzoic acid vanadium complex, the high price vanadium complex is dissolved in the raw material 2-nitro of melting-4-methylsulfonyltoluene, use again concentrated nitric acid oxidation, preparation 2-nitryl-4-thiamphenicol benzoic acid, have the following advantages: 1, the title complex of high price vanadium is easier forms the π active center with raw material, the catalytic activity of vanadium is improved, and the consumption of vanadium descends greatly, and the consumption of high price vanadium complex is the 0.2-1% of raw material; 2, the high price vanadium complex can be dissolved in the 2-nitro of melting-4-methylsulfonyltoluene system, can not use solvent, realizes that solvent free is synthetic.
Embodiment
The method that this high price vanadium complex catalyst system prepares the 2-nitryl-4-thiamphenicol benzoic acid may further comprise the steps:
(1) with a certain amount of V
2O
5Be dissolved in a small amount of concentrated sulfuric acid solution, then add the 2-nitryl-4-thiamphenicol benzoic acid of corresponding proportioning, transfer in the water heating kettle behind the stirring 30min, temperature is controlled at 140-160 ℃ of reaction 5 days.After reaction finished, filtration drying obtained high price vanadium complex crystal.
(2) the above-mentioned high price vanadium complex crystal that makes is added in 2-nitro-4-methylsulfonyltoluene molten system as catalyzer, temperature is controlled at 150-160 ℃, drip nitric acid and carry out oxidizing reaction, thickening appears in 10h afterreaction liquid, stopped heating separates to get the 2-nitryl-4-thiamphenicol benzoic acid with the alkali-soluble acid analysis method.
When going on foot described method synthetic compound according to (1), change the proportioning (mol ratio) of vanadium pentoxide and 2-nitryl-4-thiamphenicol benzoic acid, be respectively 1: 3,1:4 or 1: 6, can obtain the vanadyl complex structure of different structure, the coordination of high price vanadium is generally 6, and possible structure is as follows:
The 1st kind of possibility structure, the proportioning of vanadium pentoxide and 2-nitryl-4-thiamphenicol benzoic acid (mol ratio) is 1: 3, and the acid of three molecules obtains three 2-nitryl-4-thiamphenicol benzoic acids with high price vanadium double coordination and closes vanadium (V), and ligancy is 6.Structural formula is as follows:
The 2nd kind of possibility structure, the proportioning of vanadium pentoxide and 2-nitryl-4-thiamphenicol benzoic acid (mol ratio) is 1: 4, dimolecular acid obtains four 2-nitryl-4-thiamphenicol benzoic acids with high price vanadium double coordination and closes vanadium (V), ligancy 6.Structural formula is as follows:
The 3rd kind may structure, and the proportioning of vanadium pentoxide and 2-nitryl-4-thiamphenicol benzoic acid (mol ratio) is 1: 6, and the acid of six molecules and vanadium at high price are monodentate ligand and obtain six 2-nitryl-4-thiamphenicol benzoic acids and close vanadium (V), ligancy 6.Structural formula is as follows:
The method that this high price vanadium complex catalyst system prepares the 2-nitryl-4-thiamphenicol benzoic acid has improved oxidation products yield, and the consumption of vanadium is descended greatly, has reduced cost recovery, easier realization industrialization.Oxidizing reaction does not use sulfuric acid to make solvent yet, becomes homogeneous phase with the high price vanadium complex after the raw material fusing, realizes the solvent free reaction, so that the production of 2-nitryl-4-thiamphenicol benzoic acid is cleaned more.Product purity is high, and yield can reach about 85%.
Embodiment 1:
(1) the 0.3636g Vanadium Pentoxide in FLAKES being dissolved in 5g concentration is in 70% the concentrated sulfuric acid solution, then to add the 2.9532g2-nitryl-4-thiamphenicol benzoic acid, transfers in the 30ml water heating kettle after stirring 30min, and temperature is controlled at 150 ℃, reacts 5 days.After reaction finished, filtration drying obtains title complex three 2-nitryl-4-thiamphenicol benzoic acids and closes vanadium 1.5g, and was for subsequent use as catalyzer.
(2) 43.0g raw material 2-nitro-4-methylsulfonyltoluene is added in the reactor, add simultaneously 1.3g title complex three 2-nitryl-4-thiamphenicol benzoic acids and close the vanadium crystal.Heat up and heat, make reactant be molten state, when temperature rises to 155 ℃, begin to drip 65% nitric acid 60ml, temperature control reaction 10h.Thickening appears in 10h afterreaction liquid, and stopped heating separates to get 2-nitryl-4-thiamphenicol benzoic acid 40.85g(yield 83% with the alkali-soluble acid analysis method).
Embodiment 2:
(1) the 0.3636g Vanadium Pentoxide in FLAKES being dissolved in 5g concentration is in 70% the concentrated sulfuric acid solution, then to add the 2.9532g2-nitryl-4-thiamphenicol benzoic acid, transfers in the 30ml water heating kettle after stirring 30min, and temperature is controlled at 150 ℃, reacts 5 days.After reaction finished, filtration drying obtains title complex three 2-nitryl-4-thiamphenicol benzoic acids and closes vanadium 1.5g, and was for subsequent use as catalyzer.
(2) 43.0g raw material 2-nitro-4-methylsulfonyltoluene is added in the reactor, add simultaneously 1.3g title complex three 2-nitryl-4-thiamphenicol benzoic acids and close the vanadium crystal.Heat up and heat, make reactant be molten state, when temperature rises to 155 ℃, begin to drip 65% nitric acid 60ml, temperature control reaction 10h.Thickening appears in 10h afterreaction liquid, and stopped heating separates to get 2-nitryl-4-thiamphenicol benzoic acid 41.8g(yield 84.8% with the alkali-soluble acid analysis method).
Embodiment 3:
(1) the 0.3636g Vanadium Pentoxide in FLAKES being dissolved in 5g concentration is in 70% the concentrated sulfuric acid solution, then to add the 3.9376g2-nitryl-4-thiamphenicol benzoic acid, transfers in the 30ml water heating kettle after stirring 30min, and temperature is controlled at 150 ℃, reacts 5 days.After reaction finished, filtration drying obtains title complex four 2-nitryl-4-thiamphenicol benzoic acids and closes vanadium 1.8g, and was for subsequent use as catalyzer.
(2) 43.0g raw material 2-nitro-4-methylsulfonyltoluene is added in the reactor, add simultaneously 1.4g title complex four 2-nitryl-4-thiamphenicol benzoic acids and close vanadium.Heat up and heat, make reactant be molten state, when temperature rises to 155 ℃, begin to drip 65% nitric acid 80ml, temperature control reaction 10h.After reaction finishes, the cooling reaction solution, the static solid of separating out, the suction filtration washing, drying gets 2-nitryl-4-thiamphenicol benzoic acid 42.3g(yield 86%).
Embodiment 4:
(1) the 0.3636g Vanadium Pentoxide in FLAKES being dissolved in 5g concentration is in 70% the concentrated sulfuric acid solution, then to add the 5.9064g2-nitryl-4-thiamphenicol benzoic acid, transfers in the 30ml water heating kettle after stirring 30min, and temperature is controlled at 150 ℃, reacts 5 days.After reaction finished, filtration drying obtains title complex six 2-nitryl-4-thiamphenicol benzoic acids and closes vanadium 2.85g, and was for subsequent use as catalyzer.
(2) 43.0g raw material 2-nitro-4-methylsulfonyltoluene is added in the reactor, add simultaneously 1.6g title complex six 2-nitryl-4-thiamphenicol benzoic acids and close vanadium.Heat up and heat, make reactant be molten state, when temperature rises to 155 ℃, begin to drip 65% nitric acid 70ml, temperature control reaction 10h.Thickening appears in 10h afterreaction liquid, and stopped heating separates to get 2-nitryl-4-thiamphenicol benzoic acid 41.3g(yield 84% with the alkali-soluble acid analysis method).
Claims (3)
1. a high price vanadium complex catalyst system prepares the method for 2-nitryl-4-thiamphenicol benzoic acid, the high price vanadium complex of making take Vanadium Pentoxide in FLAKES and 2-nitryl-4-thiamphenicol benzoic acid is as catalyzer, make the 2-nitryl-4-thiamphenicol benzoic acid with nitric acid oxidation 2-nitro-4-methylsulfonyltoluene, it is characterized in that the steps include:
(1) with V
2O
5Be dissolved in a small amount of concentrated sulfuric acid solution, add the 2-nitryl-4-thiamphenicol benzoic acid, reacting by heating obtains the high price vanadium complex;
(2) the high price vanadium complex of gained of upper step is dissolved in the 2-nitro of melting-4-methylsulfonyltoluene, drips again nitric acid and carry out oxidizing reaction, make the 2-nitryl-4-thiamphenicol benzoic acid.
2. high price vanadium complex catalyst system as claimed in claim 1 prepares the method for 2-nitryl-4-thiamphenicol benzoic acid, it is characterized in that temperature of reaction is 140-160 ℃ in (1) step, and the reaction times is 5 days; The add-on of high price vanadium complex is the 0.2-1Wt% of 2-nitro-4-methylsulfonyltoluene in (2) step, and temperature of reaction is 150-160 ℃.
3. high price vanadium complex catalyst system as claimed in claim 1 or 2 prepares the method for 2-nitryl-4-thiamphenicol benzoic acid, it is characterized in that the ratio that adds of vanadium pentoxide and 2-nitryl-4-thiamphenicol benzoic acid in (1) step is that mol was than 1: 3 or 1: 4 or 1: 6.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104059001A (en) * | 2013-03-18 | 2014-09-24 | 华中师范大学 | Preparation method of o-nitro sulfuryl benzoic acid |
| CN105669504A (en) * | 2016-03-07 | 2016-06-15 | 山东润博生物科技有限公司 | Preparation method of 2-nitro-4-methyl sulphonyl benzoic acid |
| CN114213202A (en) * | 2021-12-22 | 2022-03-22 | 石河子大学 | Preparation method of 2, 4-substituted benzoic acid |
| WO2023275677A1 (en) * | 2021-06-29 | 2023-01-05 | Gharda Chemicals Limited | A process for the preparation of 2-nitro-4-(methylsulfonyl)benzoic acid |
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| US5424481A (en) * | 1992-10-19 | 1995-06-13 | Basf Aktiengesellschaft | Preparation of methylsulfonylbenzoic acids |
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-
2013
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| US5424481A (en) * | 1992-10-19 | 1995-06-13 | Basf Aktiengesellschaft | Preparation of methylsulfonylbenzoic acids |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104059001A (en) * | 2013-03-18 | 2014-09-24 | 华中师范大学 | Preparation method of o-nitro sulfuryl benzoic acid |
| CN104059001B (en) * | 2013-03-18 | 2016-06-08 | 华中师范大学 | A kind of adjacent benzoic preparation method of nitro sulfuryl |
| CN105669504A (en) * | 2016-03-07 | 2016-06-15 | 山东润博生物科技有限公司 | Preparation method of 2-nitro-4-methyl sulphonyl benzoic acid |
| WO2023275677A1 (en) * | 2021-06-29 | 2023-01-05 | Gharda Chemicals Limited | A process for the preparation of 2-nitro-4-(methylsulfonyl)benzoic acid |
| CN114213202A (en) * | 2021-12-22 | 2022-03-22 | 石河子大学 | Preparation method of 2, 4-substituted benzoic acid |
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Effective date of registration: 20191227 Address after: 314201 room 318, building 1, south side of Zhongshan Road and west side of Washan Road, Jiaxing Port Area, Jiaxing City, Zhejiang Province Patentee after: Zhejiang Jiafu New Material Technology Co.,Ltd. Address before: 314001 Yuexiu South Road, Zhejiang, No. 56, No. Co-patentee before: ZHEJIANG JIAHUA ENERGY CHEMICAL INDUSTRY CO.,LTD. Patentee before: JIAXING University |
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Effective date of registration: 20241030 Address after: No. 2288, Zhapu Binhai Avenue, Jiaxing City, Zhejiang Province, 314201 Patentee after: ZHEJIANG JIAHUA ENERGY CHEMICAL INDUSTRY CO.,LTD. Country or region after: China Address before: 314201 room 318, building 1, south side of Zhongshan Road and west side of Washan Road, Jiaxing Port Area, Jiaxing City, Zhejiang Province Patentee before: Zhejiang Jiafu New Material Technology Co.,Ltd. Country or region before: China |