CN1181036C - 2,3,5-tribromobenzoic acid as plant growth regulator and its preparing process - Google Patents
2,3,5-tribromobenzoic acid as plant growth regulator and its preparing process Download PDFInfo
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- CN1181036C CN1181036C CNB021041016A CN02104101A CN1181036C CN 1181036 C CN1181036 C CN 1181036C CN B021041016 A CNB021041016 A CN B021041016A CN 02104101 A CN02104101 A CN 02104101A CN 1181036 C CN1181036 C CN 1181036C
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- Prior art keywords
- tribromo
- diazotization
- solution
- acid
- anthranilic acid
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a novel plant growth regulator, namely 2, 3, 5-tribromobenzoic acid and a preparation method thereof, which belongs to the field of agricultural chemicals in chemical industry. Anthranilic acid is used as a basic raw material; in the presence of acidic medium, bromine is added for bromination, sodium nitrite is added for diazotization, nitrogen reacts with and hydrobromic acid or potassium bromide in the presence of a catalyst, and the products are obtained via washing, filtration and drying. The prepared 2, 3, 5-tribromobenzoic acid has the advantages of low raw material price, easy raw material acquirement, simple preparation process, moderate reaction condition and easy operation. The products also have the advantages of low toxicity, high efficiency, low preparation cost, little consumption and has obvious adjustment effects on plants, and yield is increased by 10 to 70%.
Description
Technical field
The present invention relates to one plant growth regulators-benzoic preparation method of 2.3.5-tribromo, belong to the chemical industry class.
Background technology
2.3.5-tribromo-benzene formic acid is a kind of of plant-growth regulator, belongs to the agricultural chemicals category.Be applied to farm crop, have characteristics such as efficient, low toxicity, adjusting plant growth, effect of increasing production be obvious.Be to be raw material with the anthranilic acid, through bromination, diazotization, put nitrogen and substitution reaction is prepared from.
Summary of the invention
The objective of the invention is to simple technology, prepare that a kind of toxicity is low, usage quantity is few, application cost is low, crop is had the plant-growth regulator-2.3.5-tribromo-benzene formic acid of obvious regulating effect and effect of increasing production.
The way of solution task is to be basic raw material with the anthranilic acid, with a kind of in hydrochloric acid soln or sulphuric acid soln or salpeter solution or the hydrobromic acid solution or by described any two kinds or the mixing of two or more solution is as acidic medium arbitrarily, transferring system PH is 2.0-6.8.By adding bromine bromination, separation, add Sodium Nitrite diazotization, heat up, put nitrogen, add Hydrogen bromide or Potassium Bromide carries out substitution reaction, separates, is drying to obtain 2.3.5-tribromo-benzene formic acid.
Benzoic preparation method is as follows for 2.3.5-tribromo of the present invention:
With the anthranilic acid is basic raw material, under the acidic medium condition, by bromination, diazotization, put nitrogen and carry out in the presence of catalyzer that substitution reaction makes;
Above-mentioned acidic medium can be the mixing of one or more solution in hydrochloric acid soln or sulphuric acid soln or hydrobromic acid solution or the salpeter solution, and its consumption is 2.0-6.8 for the pH value with the system of transferring to;
Above-mentioned bromination is under the acidic medium condition, controlled temperature-5 ℃--25 ℃, and add the simple substance bromine and carry out bromination reaction, the amount that adds bromine is the 60%-110% of anthranilic acid weight;
Above-mentioned diazotization is under the acidic medium condition, and controlled temperature adds sodium nitrite solution and carries out diazotization reaction at-5 ℃-20 ℃ in system, and the amount that adds Sodium Nitrite is the 50%-90% of anthranilic acid weight;
The above-mentioned nitrogen of putting is after diazotization system temperature to be risen to 0 ℃-80 ℃, emits nitrogen gradually;
Above-mentioned substitution reaction is when putting nitrogen, adds Hydrogen bromide or Potassium Bromide and catalyzer, carries out substitution reaction, and the amount that adds Hydrogen bromide or Potassium Bromide is the 20%-50% of anthranilic acid weight;
Above-mentioned catalyzer is the mixture of a kind of or any two kinds or arbitrarily two or more material in cuprous chloride or cuprous bromide or the cuprous bromide-hydrogen bromide solution: its add-on is the 0.5%-10.0% of anthranilic acid weight.
Adopt the product of manufacturing of the present invention, compare with other plant-growth regulator that to have usage quantity few, application cost is low, to characteristics such as the crop yield effect are remarkable.
Preparation method of the present invention has that technical process is simple, less investment, reaction conditions gentleness, easy handling, raw material are easily purchased, preparation cost is low etc., and this is a principal character of the present invention.
2.3.5-tribromo-benzene formic acid with the present invention's preparation with the purity difference, is dark yellow needle-like or yellow needle-like or dark yellow sheet or yellow plate crystal.
Preparation method of the present invention adopt anthranilic acid in acidic medium bromination, Sodium Nitrite diazotization, when putting nitrogen, with cuprous halide catalysis, add reactions such as Potassium Bromide or Hydrogen bromide replacement and carry out, and carry out purifying with steps such as dissolve with ethanol, recrystallization, washings.
Description of drawings
Figure of description is the technological process block-diagram of preparation method among the present invention.
Embodiment
2.3.5-tribromo-benzene formic acid and preparation method thereof embodiment
1, bromination reaction
Take by weighing anthranilic acid (C
7H
7O
2N) 5g--10g places the 300ml-500ml Erlenmeyer flask, and adding hydrochloric acid and hydrobromic mixed solution accent pH value is 2.5-5.0, adds bromine (Br slowly
2) 4.5ml-9.0ml, controlled temperature-5 ℃-25 ℃, question response finishes, the adjacent amino 3.5-dibromobenzoic acid of intermediate product.
2, diazotization reaction
In bromination reaction gained intermediate product, add the mixed solution of Hydrogen bromide and hydrochloric acid, hierarchy of control temperature adds 25% sodium nitrite solution 10ml-30ml below 15 ℃ with separating funnel, heats while stirring, and dropwises, and stirs to get the diazotization product in 5 minutes.
3, put nitrogen, substitution reaction
Heated up in the system limit of containing the diazotization product, it is 1.0-4.0 that limit adding cuprous bromide 0.1g--0.2g transfers the pH value of system with Hydrogen bromide, adds Potassium Bromide, is warming up to gradually below 80 ℃, leaves standstill 3 hours, promptly gets the product crude product solution.
4, refining
In the product crude product solution, add the 2M sodium hydroxide solution, in and the acid in the system, stir and make the product precipitation, with the dissolve with ethanol washing, filter and promptly get the product elaboration.
Claims (6)
1. benzoic preparation method of 2.3.5-tribromo, it is characterized in that: be basic raw material with the anthranilic acid, under the acidic medium condition, by bromination, diazotization, put nitrogen and carry out in the presence of catalyzer that substitution reaction makes, above-mentioned catalyzer is the mixture of a kind of or any two kinds or arbitrarily two or more material in cuprous chloride or cuprous bromide or the cuprous bromide-hydrogen bromide solution, and its add-on is the 0.5%-10.0% of anthranilic acid weight.
2. the benzoic preparation method of 2.3.5-tribromo as claimed in claim 1, it is characterized in that: said acidic medium can be the mixing of one or more solution in hydrochloric acid soln or sulphuric acid soln or hydrobromic acid solution or the salpeter solution, and its consumption is 2.0-6.8 for the pH value with the system of transferring to.
3. the benzoic preparation method of 2.3.5-tribromo as claimed in claim 1, it is characterized in that: said bromination is under the acidic medium condition, controlled temperature-5 ℃-25 ℃, add the simple substance bromine and carry out bromination reaction, the amount that adds bromine is the 60%-110% of anthranilic acid weight.
4. the benzoic preparation method of 2.3.5-tribromo as claimed in claim 1, it is characterized in that: said diazotization, be under the acidic medium condition, controlled temperature is at-5 ℃-20 ℃, add sodium nitrite solution and carry out diazotization reaction in system, the amount that adds Sodium Nitrite is the 50%-90% of anthranilic acid weight.
5. the benzoic preparation method of 2.3.5-tribromo as claimed in claim 1 is characterized in that: the said nitrogen of putting is after diazotization system temperature to be risen to 0 ℃-80 ℃, emits nitrogen gradually.
6. the benzoic preparation method of 2.3.5-tribromo as claimed in claim 1, it is characterized in that: said substitution reaction, be when putting nitrogen, add Hydrogen bromide or Potassium Bromide and catalyzer, carry out substitution reaction, the amount that adds Hydrogen bromide or Potassium Bromide is the 20%-50% of anthranilic acid weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021041016A CN1181036C (en) | 2002-03-04 | 2002-03-04 | 2,3,5-tribromobenzoic acid as plant growth regulator and its preparing process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021041016A CN1181036C (en) | 2002-03-04 | 2002-03-04 | 2,3,5-tribromobenzoic acid as plant growth regulator and its preparing process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1369474A CN1369474A (en) | 2002-09-18 |
| CN1181036C true CN1181036C (en) | 2004-12-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB021041016A Expired - Fee Related CN1181036C (en) | 2002-03-04 | 2002-03-04 | 2,3,5-tribromobenzoic acid as plant growth regulator and its preparing process |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20120135864A1 (en) * | 2009-04-07 | 2012-05-31 | Taminco, Naamloze Vennootschap | Pollination improver |
| CN113912487B (en) * | 2021-11-23 | 2024-05-28 | 山东研峰新材料科技有限公司 | Synthesis method of 2, 5-dihalobenzoic acid |
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2002
- 2002-03-04 CN CNB021041016A patent/CN1181036C/en not_active Expired - Fee Related
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| CN1369474A (en) | 2002-09-18 |
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Granted publication date: 20041222 Termination date: 20160304 |