CN101812030A - High-pressure production method of 5-hydroxymethyl-tetrazole or 5-hydroxyethyl tetrazole - Google Patents
High-pressure production method of 5-hydroxymethyl-tetrazole or 5-hydroxyethyl tetrazole Download PDFInfo
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- CN101812030A CN101812030A CN 201010158944 CN201010158944A CN101812030A CN 101812030 A CN101812030 A CN 101812030A CN 201010158944 CN201010158944 CN 201010158944 CN 201010158944 A CN201010158944 A CN 201010158944A CN 101812030 A CN101812030 A CN 101812030A
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- tetrazole
- hydroxyethyl
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- methylol
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Abstract
The invention discloses a high-pressure production method of 5-hydroxymethyl-tetrazole or 5-hydroxyethyl tetrazole; and hydroxy-acetonitrile or hydroxypropanitrile and sodium azide, triethylamine and the like react to prepare the 5-hydroxymethyl-tetrazole or the 5-hydroxyethyl tetrazole under a high-pressure condition. The high-pressure production method of 5-hydroxymethyl-tetrazole or 5-hydroxyethyl tetrazole has simple process, is easy to operate, does not produce wastewater and waste gas, and the product yield reaches 85 percent.
Description
Technical field:
The present invention relates to the high pressure production method of a kind of 5-methylol tetrazole or 5-hydroxyethyl tetrazole.
Background technology:
5-methylol tetrazole or 5-hydroxyethyl tetrazole are a kind of key intermediates that offshore company such as BASF produces new drug, and it is synthetic mainly to be in short run at present.
5-methylol tetrazole or 5-hydroxyethyl tetrazole are produced, and existing U.S. Pat 333325 mainly is to react in the DMF solvent with hydroxyacetonitrile or hydroxypropionitrile, ammonium chloride and sodiumazide, and aftertreatment obtains product; US5284957 reacts in toluene solvant with hydroxyacetonitrile or hydroxypropionitrile, tributyltin chloride and sodiumazide, and aftertreatment obtains product; This complex process, yield is low, and the three wastes are many.
Summary of the invention:
The object of the present invention is to provide a kind of technology simple, yield height, the production method of the 5-methylol tetrazole of no waste water or 5-hydroxyethyl tetrazole.
Technical solution of the present invention is:
The high pressure production method of a kind of 5-methylol tetrazole or 5-hydroxyethyl tetrazole, it is characterized in that: by hydroxyacetonitrile or hydroxypropionitrile, sodiumazide, triethylamine 1: 0.8 according to a certain percentage～2.5: 0.8～50, its preferred molar ratio is 1: 1.0～1.5: 6～15; Being heated to 80-200 ℃ of preferred temperature is 100-160 ℃; Stirring reaction 2-60 hour its preferred stirring reaction time was 5-40 hour.Reaction finishes the back and adds the liquid caustic soda layering, and to PH1-2, pressure reducing and steaming water obtains solid phase prod to oil reservoir, and water and the solid sodium hydroxide that steams is used to prepare liquid caustic soda with hcl acidifying.This product solid is extracted the refining product that obtains with the vinyl acetic monomer heating.
Its reaction formula is as follows:
The advantage of technology of the present invention is simple, and easy to operate, product yield is up to 85%.
The invention will be further described below in conjunction with embodiment:
Embodiment:
Embodiment 1:
Molar ratio is a hydroxyacetonitrile: sodiumazide: triethylamine hydrochloric acid: triethylamine=1: 1: 2: 10.
After in having the autoclave of stirring, adding reaction mass according to top proportioning, the off-response still, heat to 145 ℃, reacted 6 hours, reaction finishes the back and adds the liquid caustic soda layering, to PH1-2, pressure reducing and steaming water obtains solid phase prod to oil reservoir, and water and the solid sodium hydroxide that steams is used to prepare liquid caustic soda with hcl acidifying.This product solid is extracted the refining product, content 99.6% molar yield 85% of obtaining with the vinyl acetic monomer heating.
Embodiment 2:
Molar ratio is a hydroxypropionitrile: sodiumazide: triethylamine hydrochloric acid: triethylamine=1: 1: 2: 10.
After in having the autoclave of stirring, adding reaction mass according to top proportioning, the off-response still, heat to 145 ℃, reacted 6 hours, reaction finishes the back and adds the liquid caustic soda layering, to PH1-2, pressure reducing and steaming water obtains solid phase prod to oil reservoir, and water and the solid sodium hydroxide that steams is used to prepare liquid caustic soda with hcl acidifying.This product solid is extracted the refining product, content 99.4% molar yield 88% of obtaining with the vinyl acetic monomer heating.
Embodiment 3:
Molar ratio is a hydroxyacetonitrile: sodiumazide: triethylamine hydrochloric acid: triethylamine=1: 1: 2: 10.
After in having the autoclave of stirring, adding reaction mass according to top proportioning, the off-response still, heat to 135 ℃, reacted 12 hours, reaction finishes the back and adds the liquid caustic soda layering, to PH1-2, pressure reducing and steaming water obtains solid phase prod to oil reservoir, and water and the solid sodium hydroxide that steams is used to prepare liquid caustic soda with hcl acidifying.This product solid is extracted the refining product, content 99.2% molar yield 87% of obtaining with the vinyl acetic monomer heating.
Embodiment 4:
Molar ratio is a hydroxypropionitrile: sodiumazide: triethylamine hydrochloric acid: triethylamine=1: 1: 2: 10.
After in having the autoclave of stirring, adding reaction mass according to top proportioning, the off-response still, heat to 135 ℃, reacted 12 hours, reaction finishes the back and adds the liquid caustic soda layering, to PH1-2, pressure reducing and steaming water obtains solid phase prod to oil reservoir, and water and the solid sodium hydroxide that steams is used to prepare liquid caustic soda with hcl acidifying.This product solid is extracted the refining product, content 99.5% molar yield 92% of obtaining with the vinyl acetic monomer heating.
Claims (7)
1. the high pressure production method of 5-methylol tetrazole or 5-hydroxyethyl tetrazole, it is characterized in that: react under condition of high voltage by hydroxyacetonitrile or hydroxypropionitrile, sodiumazide, triethylamine and generate 5-methylol tetrazole or 5-hydroxyethyl tetrazole, reaction formula:
2. the high pressure production method of a kind of 5-methylol tetrazole according to claim 1 or 5-hydroxyethyl tetrazole is characterized in that: reaction is to carry out under 80-200 ℃ of condition of heating.
3. the high pressure production method of a kind of 5 methylol tetrazoles according to claim 2 or 5-hydroxyethyl tetrazole, it is characterized in that: the preferred Heating temperature of described reaction is 100-160 ℃.
4. the high pressure production method of a kind of 5-methylol tetrazole according to claim 1 or 5-hydroxyethyl tetrazole is characterized in that: the mol ratio of hydroxyacetonitrile or hydroxypropionitrile, sodiumazide, triethylamine is hydroxyacetonitrile or hydroxypropionitrile: sodiumazide: triethylamine=1: 0.8～2.5: 0.8～50.
5. the high pressure production method of a kind of 5-methylol tetrazole according to claim 4 or 5 hydroxyethyl tetrazoles is characterized in that: the preferred molar ratio of hydroxyacetonitrile or hydroxypropionitrile, sodiumazide, triethylamine is hydroxyacetonitrile or hydroxypropionitrile: sodiumazide: triethylamine=1: 1.0～1.5: 6～15.
6. the high pressure production method of a kind of 5-methylol tetrazole according to claim 1 or 5-hydroxyethyl tetrazole is characterized in that: the reaction times is 2-60 hour.
7. the high pressure production method of a kind of 5-methylol tetrazole according to claim 6 or 5-hydroxyethyl tetrazole is characterized in that: the preferred time of described reaction is 5-40 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010158944 CN101812030A (en) | 2010-04-29 | 2010-04-29 | High-pressure production method of 5-hydroxymethyl-tetrazole or 5-hydroxyethyl tetrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010158944 CN101812030A (en) | 2010-04-29 | 2010-04-29 | High-pressure production method of 5-hydroxymethyl-tetrazole or 5-hydroxyethyl tetrazole |
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| CN101812030A true CN101812030A (en) | 2010-08-25 |
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| CN 201010158944 Pending CN101812030A (en) | 2010-04-29 | 2010-04-29 | High-pressure production method of 5-hydroxymethyl-tetrazole or 5-hydroxyethyl tetrazole |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4791210A (en) * | 1986-10-11 | 1988-12-13 | Dynamit Nobel Aktiengesellschaft | Process for the production of 5-methyltetrazole |
| CN101255141A (en) * | 2008-03-17 | 2008-09-03 | 江苏德峰医药化工有限公司 | Production technique for preparing 5-methyl tetrazole by high pressure method |
| CN101260084A (en) * | 2008-03-17 | 2008-09-10 | 江苏德峰医药化工有限公司 | Production technique for preparing 5-alkyltetranitrozole by high pressure method |
-
2010
- 2010-04-29 CN CN 201010158944 patent/CN101812030A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4791210A (en) * | 1986-10-11 | 1988-12-13 | Dynamit Nobel Aktiengesellschaft | Process for the production of 5-methyltetrazole |
| CN101255141A (en) * | 2008-03-17 | 2008-09-03 | 江苏德峰医药化工有限公司 | Production technique for preparing 5-methyl tetrazole by high pressure method |
| CN101260084A (en) * | 2008-03-17 | 2008-09-10 | 江苏德峰医药化工有限公司 | Production technique for preparing 5-alkyltetranitrozole by high pressure method |
Non-Patent Citations (1)
| Title |
|---|
| 《火炸药学报》 20090228 刘庆 等 5-乙烯基四唑的合成及表征 29-31 1-7 第32卷, 第1期 2 * |
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Open date: 20100825 |