CN108892617A - A kind of preparation method of Isopropyl Nitrite - Google Patents
A kind of preparation method of Isopropyl Nitrite Download PDFInfo
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- CN108892617A CN108892617A CN201810933036.3A CN201810933036A CN108892617A CN 108892617 A CN108892617 A CN 108892617A CN 201810933036 A CN201810933036 A CN 201810933036A CN 108892617 A CN108892617 A CN 108892617A
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- CN
- China
- Prior art keywords
- preparation
- nitric acid
- isopropyl nitrite
- reaction
- isopropyl
- 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.)
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- SKRDXYBATCVEMS-UHFFFAOYSA-N isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 41
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 16
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 15
- 238000009413 insulation Methods 0.000 claims abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 32
- 229910017604 nitric acid Inorganic materials 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 10
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 235000010344 sodium nitrate Nutrition 0.000 claims description 3
- 239000004317 sodium nitrate Substances 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 11
- 238000003756 stirring Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 2
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 sodium nitrite-isopropanol-nitric acid Chemical group 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- QEBGRPQAKNUHIS-UHFFFAOYSA-N 2-bromo-1-iodopropane Chemical compound CC(Br)CI QEBGRPQAKNUHIS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000605122 Nitrosomonas Species 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QYAIYPDHHRBYRW-UHFFFAOYSA-N nitric acid;propan-2-ol Chemical compound CC(C)O.O[N+]([O-])=O QYAIYPDHHRBYRW-UHFFFAOYSA-N 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/04—Preparation of esters of nitrous acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation methods of Isopropyl Nitrite, and specific step is as follows：Isopropanol is added into reaction vessel, sodium nitrite is added while stirring, control reaction temperature is 20~50 DEG C, and dilution heat of sulfuric acid is slowly added dropwise, rear insulation reaction is added dropwise, separates to obtain the final product.Preparation method simple process of the invention, condition is easy to control, production cost is low, safety coefficient is high, convenient post-treatment, has very strong operability and repeatability, and synthetic method of the invention, product yield can reach 95% or more, be convenient for industrialized production, solve the problems such as difficult control of reaction conditions, high production cost existing for traditional handicraft, yield be low.
Description
Technical field
The present invention relates to a kind of synthetic methods, and in particular to a kind of preparation method of Isopropyl Nitrite.Belong to organic conjunction
At technical field.
Background technique
Isopropyl Nitrite genus nitrosomonas esters, stability is not high, explosive, hardly possible storage, for distending the blood vessels, blood pressure
Decline and tachycardia play an important role, and have in military, engineering technology and medicine and other fields and are widely applied.Meanwhile nitrous acid
Isopropyl ester or a kind of preferable diazo reagent.
The preparation method of traditional Isopropyl Nitrite has 3 kinds, one is by isopropanol-Nitrosation Process, using isopropanol,
Sodium nitrite, sulfuric acid be raw material, under dichloromethane solvent react be made, and sulfuric acid be raw material, by-product sodium sulphate added value compared with
Low, for sulfuric acid concentration within 40%, water consumption is larger, and reaction yield is lower (84%)；Another kind be 2- bromo (iodo) propane,
Silver nitrite is made for raw material；Not only reaction yield is low (52%), but also more demanding to operating condition, and wastewater flow rate is big, production
It is expensive；Still an alternative is that being prepared using benzophenone and isopropanol reaction, but by-product diformazan can be generated
Ketone, reaction are not easy to control.Therefore, there is an urgent need to the methods that one kind safe and efficient can prepare nitric acid isopropanol.
Summary of the invention
The purpose of the present invention is to overcome above-mentioned the deficiencies in the prior art, provide a kind of preparation side of Isopropyl Nitrite
Method, it is sodium nitrite-isopropanol-nitric acid reaction body that this method, which improves original technique sodium nitrite-ethyl alcohol-sulfuric acid reaction system,
System.
To achieve the above object, the present invention adopts the following technical solutions：
A kind of preparation method of Isopropyl Nitrite, specific step is as follows：By nitric acid solution agitation and dropping to sodium nitrite
In the mixed system of isopropanol composition, reaction temperature is controlled, rear insulation reaction is dripped, is collected since being added dropwise nitric acid solution
Liquid Isopropyl Nitrite obtains Isopropyl Nitrite, reaction equation is as follows until no liquid generates：
iPrOH+HNO3+NaNO2→iPrONO+NaNO3+H2O。
In the above method, esterification material sodium nitrite：Isopropanol：Nitric acid (molar ratio) is 1.0：1.05~1.20：
0.50~0.70；
Preferably, esterification material matches sodium nitrite：Isopropanol：Nitric acid (molar ratio)=1.0：1.05：0.50.
Preferably, the nitric acid solution concentration that the esterification of Isopropyl Nitrite uses is prepared as 30~68%；
It is further preferred that the concentration of the nitric acid solution is 40%~50%.
In the above method, 1.5~2h of preferred nitric acid solution time for adding, it is 25~40 DEG C that process reaction temperature, which is added dropwise,；
It is further preferred that it is 30~35 DEG C that process reaction temperature, which is added dropwise, in the nitric acid solution.
In the above method, the time of preferred insulation reaction is 0.5~2 hour, and the temperature of insulation reaction is 40~50 DEG C；
In the above method, reaction system is aqueous systems, with water as solvent.
In the above method, water is the reaction dissolvent of reaction system, and reaction system includes nitric acid solution, sodium nitrite, isopropyl
Alcohol.Wherein the mixed system of sodium nitrite and isopropanol composition is the aqueous isopropanol of sodium nitrite.
Beneficial effects of the present invention：
The present invention is using isopropanol, nitrous acid and dilute nitric acid solution as raw material, by under water phase nitric acidic environment, isopropanol
Isopropyl Nitrite is prepared with reacting at ester for nitrous acid, distillation obtains Isopropyl Nitrite.
Preparation method of the invention replaces dichloromethane solvent with water, and technique clean and environmental protection is provided with nitric acid substitution sulfuric acid
Acidic environment reacts milder, and condition is easy to control, and safety coefficient is high, and side reaction substantially reduces, and by-product sodium nitrate and tradition
Sodium sulphate is compared, and height is added, and cost reduces, and is had very strong operability and repeatability, and synthetic method of the invention, is produced
Product yield can reach 92% or more, be convenient for industrialized production, solve difficult control of reaction conditions, life existing for traditional handicraft
Produce many problems such as at high cost, yield is low.
Specific embodiment
Below with reference to embodiment, the present invention will be further elaborated, it should explanation, following the description merely to
It explains the present invention, its content is not defined.
Embodiment 1：
30% nitric acid solution 105ml (0.5mol) stirring is added to 69 grams of (1.0mol) sodium nitrites and 80.4ml
In the mixed system of (1.05mol) isopropanol composition, 25 DEG C of reactions are kept the temperature, 1.5h keeps the temperature 40 DEG C of reaction 0.5h again after dripping,
Liquid Isopropyl Nitrite is collected since being added dropwise nitric acid, until no longer receiving, obtains Isopropyl Nitrite 82.0g, this is anti-
Answering yield is 92.0%.
Embodiment 2：
30% nitric acid solution 105ml (0.5mol) stirring is added to 69 grams of (1.0mol) sodium nitrites and 80.4ml
In the mixed system of (1.05mol) isopropanol composition, 40 DEG C of reactions are kept the temperature, 2.0h keeps the temperature 50 DEG C of reaction 2.0h again after dripping,
Liquid Isopropyl Nitrite is collected since being added dropwise nitric acid, until no longer receiving, obtains Isopropyl Nitrite 85.6g, this is anti-
Answering yield is 96.0%.
Embodiment 3：
68% nitric acid solution 64.9ml (0.7mol) stirring is added to 69 grams of (1.0mol) sodium nitrites and 80.4ml
In the mixed system of (1.05mol) isopropanol composition, 25 DEG C of reactions are kept the temperature, 1.5h keeps the temperature 40 DEG C of reaction 2.0h again after dripping,
Liquid Isopropyl Nitrite is collected since being added dropwise nitric acid, until no longer receiving, obtains Isopropyl Nitrite 77.5g, this is anti-
Answering yield is 87.0%.
Embodiment 4：
40% nitric acid solution 78.8ml (0.5mol) stirring is added to 69 grams of (1.0mol) sodium nitrites and 91.9ml
In the mixed system of (1.2mol) isopropanol composition, 35 DEG C of reactions are kept the temperature, 1.5h keeps the temperature 50 DEG C of reaction 2.0h again after dripping, from
Nitric acid is added dropwise to start to collect liquid Isopropyl Nitrite, until no longer receiving, obtains Isopropyl Nitrite 86.2g, the reaction
Yield is 96.8%.
Embodiment 5：
30% nitric acid solution 105ml (0.5mol) stirring is added to 69 grams of (1.0mol) sodium nitrites and 80.4ml
In the mixed system of (1.05mol) isopropanol composition, 30 DEG C of reactions are kept the temperature, 1.5h keeps the temperature 40 DEG C of reaction 0.5h again after dripping,
Liquid Isopropyl Nitrite is collected since being added dropwise nitric acid, until no longer receiving, obtains Isopropyl Nitrite 84.2g, this is anti-
Answering yield is 94.6%.
Embodiment 6：
30% nitric acid solution 105ml (0.5mol) stirring is added to 69 grams of (1.0mol) sodium nitrites and 80.4ml
In the mixed system of (1.05mol) isopropanol composition, 25 DEG C of reactions are kept the temperature, 1.5h keeps the temperature 40 DEG C of reaction 0.5h again after dripping,
Liquid Isopropyl Nitrite is collected since being added dropwise nitric acid, until no longer receiving, obtains Isopropyl Nitrite 79.5g, this is anti-
Answering yield is 89.3%.
Above-mentioned, although specific embodiments of the present invention have been described, not to the limit of the scope of the present invention
System, based on the technical solutions of the present invention, those skilled in the art do not need to make the creative labor can make it is each
Kind modification or deformation are still within protection scope of the present invention.
Claims (9)
1. a kind of preparation method of Isopropyl Nitrite, which is characterized in that specific step is as follows：Nitric acid solution agitation and dropping is arrived
In the mixed system of sodium nitrite and isopropanol composition, reaction temperature is controlled, rear insulation reaction is dripped, from dropwise addition nitric acid solution
Start to collect liquid Isopropyl Nitrite, until no liquid generates, obtains Isopropyl Nitrite, reaction equation is as follows：
iPrOH+NHO3+NaNO2→iPrONO+NaNO3+H2O。
2. a kind of preparation method of Isopropyl Nitrite according to claim 1, which is characterized in that the isopropanol, Asia
The molar ratio of sodium nitrate and nitric acid is 1.0：1.05~1.20：0.50~0.70.
3. a kind of preparation method of Isopropyl Nitrite according to claim 2, which is characterized in that the isopropanol, Asia
The molar ratio of sodium nitrate and nitric acid is 1.0：1.05：0.50.
4. the preparation method of described in any item a kind of Isopropyl Nitrites according to claim 1~3, which is characterized in that described
Nitric acid solution concentration is 30~68%.
5. a kind of preparation method of Isopropyl Nitrite according to claim 4, which is characterized in that the nitric acid solution
Concentration is 40%~50%.
6. a kind of preparation method of Isopropyl Nitrite according to claim 1 or 2, which is characterized in that the nitric acid drop
It is 1.5~2h between added-time, the reaction temperature that process is added dropwise is 25~40 DEG C.
7. a kind of preparation method of Isopropyl Nitrite according to claim 6, which is characterized in that the nitric acid dropping mistake
Journey reaction temperature is 30~35 DEG C.
8. a kind of preparation method of Isopropyl Nitrite according to claim 1 or 2, which is characterized in that the heat preservation
Reaction time is 0.5~2 hour, and insulation reaction temperature is 40~50 DEG C.
9. a kind of preparation method of Isopropyl Nitrite according to claim 1 or 2, which is characterized in that reaction system is
Aqueous systems, with water as solvent.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810933036.3A CN108892617A (en) | 2018-08-16 | 2018-08-16 | A kind of preparation method of Isopropyl Nitrite |
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| CN201810933036.3A CN108892617A (en) | 2018-08-16 | 2018-08-16 | A kind of preparation method of Isopropyl Nitrite |
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| Country | Link |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980496A (en) * | 1989-12-05 | 1990-12-25 | Fruchey Olan S | Method for producing C1 to C5 alkyl nitrides |
| CN103570551A (en) * | 2012-07-25 | 2014-02-12 | 中国石油化工股份有限公司 | Device and method for synthesizing nitrite used for oxalate |
| CN106831439A (en) * | 2017-03-06 | 2017-06-13 | 西南化工研究设计院有限公司 | One kind prepares the method and device of C1 ~ C4 alkyl nitriteesters |
-
2018
- 2018-08-16 CN CN201810933036.3A patent/CN108892617A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980496A (en) * | 1989-12-05 | 1990-12-25 | Fruchey Olan S | Method for producing C1 to C5 alkyl nitrides |
| CN103570551A (en) * | 2012-07-25 | 2014-02-12 | 中国石油化工股份有限公司 | Device and method for synthesizing nitrite used for oxalate |
| CN106831439A (en) * | 2017-03-06 | 2017-06-13 | 西南化工研究设计院有限公司 | One kind prepares the method and device of C1 ~ C4 alkyl nitriteesters |
Non-Patent Citations (2)
| Title |
|---|
| 张奎 等: "改良Gomberg-Bachmann法合成2,4-二氟联苯的研究", 《杭州化工》 * |
| 徐娟娟，胡艾希: "氨噻肟酸的合成", 《精细化工》 * |
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