CN109573967A - A kind of preparation method of hydroxylamine hydrochloride - Google Patents
A kind of preparation method of hydroxylamine hydrochloride Download PDFInfo
- Publication number
- CN109573967A CN109573967A CN201811502067.XA CN201811502067A CN109573967A CN 109573967 A CN109573967 A CN 109573967A CN 201811502067 A CN201811502067 A CN 201811502067A CN 109573967 A CN109573967 A CN 109573967A
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- Prior art keywords
- hydroxylamine hydrochloride
- butanone
- diacetylmonoxime
- preparation
- condensation
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/14—Hydroxylamine; Salts thereof
- C01B21/1409—Preparation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
Abstract
The present invention relates to hydroxylamine salt preparation fields, and in particular to a kind of preparation method of hydroxylamine hydrochloride.Using the butanone oxime hydrochloride and water of certain mass hydrolysis and crystallizing and drying occur for the present invention, the butanone of generation and the impurity diacetylmonoxime in raw material pass through condensation and oil water separator, finally by the alkali cleaning of alkali cleaning knockout tower and rectifying column rectifying recycling butanone and diacetylmonoxime material.In advance mixer mixing is added in butanone oxime hydrochloride and water by the present invention, it mixes well, later period butanone oxime hydrochloride is facilitated to react more complete with water, addition catalyst accelerates reaction process during the reaction, other products are reacted to recycle after three-level condensation, oil water separator and alkali cleaning knockout tower, energy-efficient, product yield is high.
Description
Technical field
The present invention relates to hydroxylamine salt preparation fields, particularly, are related to a kind of preparation method of hydroxylamine hydrochloride.
Background technique
Hydroxylamine hydrochloride is a kind of colourless crystallization, is easily deliquesced, and white chemical substance is mainly used as reducing agent and imaging agent,
It is used to prepare oxime in organic synthesis, also serves as synthesis anticarcinogen, sulfa drug and pesticide, therefore hydroxylamine hydrochloride is a kind of important change
Work raw material, at present it is more largely to there is complex technical process, by-product in the method for industrial synthetic hydrochloric acid azanol, and yield is low, three
The problems such as useless discharge amount is big, environmental pollution is serious.Therefore, market demand one kind is energy-efficient, product yield is high and environmental-friendly
Hydroxylamine hydrochloride Novel synthesis technology.During preparing methyl tributanoximo silane, using methyl trichlorosilane and butanone
Oxime is carried out as raw material, and butanone oxime hydrochloride, and diacetylmonoxime can be also generated while generating methyl tributanoximo silane
Hydrochloride yield is larger, and this case is using the butanone oxime hydrochloride generated in the preparation process as raw material.
Summary of the invention
The technical problems to be solved by the present invention are: providing a kind of salt energy-efficient, product yield is high and environmental-friendly
The preparation method of sour azanol.
The present invention solves its technical problem technical solution to be taken: a kind of preparation method of hydroxylamine hydrochloride, step
It is rapid as follows:
1) will butanone oxime hydrochloride and water mix after in 40~45 DEG C, keep the temperature as 1~2h, obtain premixed liquid；The diacetylmonoxime
The molar ratio of hydrochloride and water are as follows: 1:7~16；
2) premixed liquid in step 1) and catalyst Ti-si molecular sieves are after mixing after 75~85 DEG C of 7~9h of reaction,
Obtain hydroxylamine hydrochloride and by-product butanone；
3) by hydroxylamine hydrochloride in step 2) go in crystallization cylinder and crystallized to obtain the final product.
Contain least a portion of diacetylmonoxime impurity in the raw material butanone oxime hydrochloride that the present invention uses.
Reaction in the step 2) carries out under the conditions of pressure is 45~55KPa.
Further, benefit is recycled after the impurity diacetylmonoxime in the butanone and raw material in step 2) is condensed by condenser
With.
Further, the condenser is condensed into three-level condensation cooling, the condition of the three-level condensation are as follows: first order condensation
Using 30~34 DEG C of condensed waters, second level condensation uses 6~8 DEG C of condensed waters, -13~-16 DEG C of condensed waters of third level use.
Further, the impurity diacetylmonoxime in the butanone and raw material enters oil water separator after condensation, described
The water phase that oil water separator is isolated includes water, is back to use in the process of step 1), the oily phase that the grease current divider is isolated
Part includes butanone and diacetylmonoxime, the upper layer aqueous solution by alkali cleaning knockout tower alkali cleaning, after the alkali cleaning knockout tower alkali cleaning
In diacetylmonoxime send to diacetylmonoxime recycle station arrangement, butanone and remaining diacetylmonoxime after the alkali cleaning knockout tower alkali cleaning are sent
It is separated to rectifying column rectifying.
Further, the temperature of the rectifying column is 105~115 DEG C, and pressure is 4900~5100Pa, rectifying in rectifying column
Time is 1.5~2.5h.
Further, the temperature in the step 3) in crystallization cylinder is controlled at 38-42 DEG C, reaction pressure 45-55KPa,
Crystallization time is 9-11h.
Further, solid hydrochloric acid hydroxyl is made in the drying technique after crystallization of the hydroxylamine hydrochloride in the step 3)
Amine.
Further, the drying process uses pneumatic conveying drying, and temperature is 100-120 DEG C in drier.
Further, the lye in the alkali cleaning knockout tower is NaOH lye.
The beneficial effects of the present invention are:
In advance mixer mixing is added in butanone oxime hydrochloride and water by the present invention, is mixed well, is facilitated subsequent butanone oximate
Hydrochlorate reacts more complete with water, adds catalyst during the reaction and accelerates reaction process, and the hydroxylamine hydrochloride for reacting generation passes through
Crystallization, drying are made；Impurity diacetylmonoxime in reaction product butanone and raw material enters oil water separator, oil after three-level condenses
The aqueous portion that separator is isolated recycles, and the oil phase part lease making that oil water separator is isolated is crossed after alkali cleaning knockout tower again
Diacetylmonoxime is recycled by rectifying column rectifying, is made the higher butanone of purity, process conditions are simple, high income, and the by-product produced
Object recycles, energy-efficient, reduces cost.
Specific embodiment
Embodiment one
The preparation method of the hydroxylamine hydrochloride of the present embodiment the following steps are included:
1) water of the butanone oxime hydrochloride of 122g and 126g are added in mixer and keep the temperature 40 DEG C, heat preservation 1h is sufficiently mixed
It is even, premixed liquid is made；
2) it takes the Titanium Sieve Molecular Sieve of 20g to be put into reaction kettle, the premixed liquid being uniformly mixed by step 1) is put into reaction
Kettle is warming up to 80 DEG C, reaction pressure 50KPa, reacts 8h, obtains hydroxylamine hydrochloride and by-product butanone；
3) it will be gone in crystallization cylinder by the hydroxylamine hydrochloride in step 2), crystallize the temperature in cylinder and control the reaction at 40 DEG C
Pressure is 50KPa, after crystallizing 10h, is separated by solid-liquid separation, is squeezed into closed filter with charge pump, by solid hydrochloric acid hydroxyl after cooling
Amine separation, the solid hydroxylamine hydrochloride isolated use pneumatic conveying drying, and drying temperature is 110 DEG C.The dust of pneumatic conveying drying passes through cloth
Bag dust collector dedusting, the dedusting product (hydroxylamine hydrochloride) that gets off return to product packaging process.
Wherein, the impurity diacetylmonoxime in the butanone and raw material after step 2) reaction by three-level condensation, (adopt by first order condensation
With 32 DEG C of condensed waters, second level condensation uses 7 DEG C of condensation water condensations, and the third level condenses -15 DEG C of condensation water condensations of use), condensation
Material afterwards enters in oil water separator, includes the process that water is back to use step 1) by the aqueous portion that oil water separator separates
In, the oil phase part separated point (butanone and diacetylmonoxime) in NaOH lye circulation in alkali cleaning knockout tower through 30% concentration and
Overflow is to alkali cleaning liquid bath afterwards, and upper layer aqueous solution (diacetylmonoxime) send to diacetylmonoxime and recycles station arrangement, by the alkali cleaning knockout tower alkali
Butanone and remaining diacetylmonoxime material after washing are sent to rectifying column rectifying, and rectifying column is by the way of steam jacket heating, temperature
It is 110 DEG C, pressure is 5000Pa in rectifying column, and rectifying 2h, the butanone that rectifying is isolated by three-level condensation, (adopt by first order condensation
With 32 DEG C of condensed waters, second level condensation uses 7 DEG C of condensation water condensations, and the third level condenses -15 DEG C of condensation water condensations of use) it is used for afterwards
Diacetylmonoxime is produced, the diacetylmonoxime isolated is distilled and sends to diacetylmonoxime recyclable device, fixed gas discharge, materials at bottom of tower passes through oxime water pump
It is delivered to oxime water recovery device.
In addition, the catalyst (Titanium Sieve Molecular Sieve) in step 2) is periodically added in reaction kettle, one section of catalyst circulation
Time after, will generate a certain amount of catalyst from the bottom of reaction kettle be discharged.
In step 2), in terms of butanone oxime hydrochloride, reaction conversion ratio 100%, hydroxylamine hydrochloride is selectively 99.17%,
End reaction yield is 99.17% (product decomposes 0.83%), and side reaction is selectively 0.83%.
After step 3) is dry, the total recovery of solid hydroxylamine hydrochloride is 98.62%.
Embodiment two
The preparation method of the hydroxylamine hydrochloride of the present embodiment the following steps are included:
1) water of the butanone oxime hydrochloride of 122g and 180g are added in mixer and keep the temperature 42 DEG C, heat preservation 1.5h, sufficiently
It mixes, premixed liquid is made；
2) it takes the Titanium Sieve Molecular Sieve of 25g to be put into reaction kettle, the premixed liquid being uniformly mixed by step 1) is put into reaction
Kettle is warming up to 75 DEG C, reaction pressure 45KPa, reacts 7h, obtains hydroxylamine hydrochloride and by-product butanone；
3) it will be gone in crystallization cylinder by the hydroxylamine hydrochloride in step 2), crystallize the temperature in cylinder and control the reaction at 38 DEG C
Pressure is 45KPa, after crystallizing 9h, is separated by solid-liquid separation, is squeezed into closed filter with charge pump, by solid hydroxylamine hydrochloride after cooling
Separation, the solid hydroxylamine hydrochloride isolated use pneumatic conveying drying, and drying temperature is 100 DEG C.The dust of pneumatic conveying drying passes through cloth bag
Deduster dedusting, the dedusting product (hydroxylamine hydrochloride) that gets off return to product packaging process.
Wherein, the impurity diacetylmonoxime in the butanone and raw material after step 2) reaction by three-level condensation, (adopt by first order condensation
With 30 DEG C of condensed waters, second level condensation uses 6 DEG C of condensation water condensations, and the third level condenses -13 DEG C of condensation water condensations of use), condensation
Material afterwards enters in oil water separator, includes the process that water is back to use step 1) by the aqueous portion that oil water separator separates
In, the oil phase part separated point (butanone and diacetylmonoxime) in NaOH lye circulation in alkali cleaning knockout tower through 30% concentration and
Overflow is to alkali cleaning liquid bath afterwards, and upper layer aqueous solution (diacetylmonoxime) send to diacetylmonoxime and recycles station arrangement, by the alkali cleaning knockout tower alkali
Butanone and remaining diacetylmonoxime material after washing are sent to rectifying column rectifying, and rectifying column is by the way of steam jacket heating, temperature
It is 105 DEG C, pressure is 4900Pa, rectifying 1.5h in rectifying column.The butanone that rectifying is isolated condenses (first order condensation by three-level
Using 30 DEG C of condensed waters, second level condensation uses 6 DEG C of condensation water condensations, and the third level condenses -13 DEG C of condensation water condensations of use) it uses afterwards
In production diacetylmonoxime, distills the diacetylmonoxime isolated and send to diacetylmonoxime recyclable device, fixed gas discharge, materials at bottom of tower passes through oxime water
Pump is delivered to oxime water recovery device.
In addition, the catalyst (Titanium Sieve Molecular Sieve) in step 2) reaction tower is periodically added in reaction kettle, catalyst is followed
After the time that one of ring, a certain amount of catalyst will be generated and be discharged from the bottom of reaction kettle.
In step 2), in terms of butanone oxime hydrochloride, reaction conversion ratio 100%, hydroxylamine hydrochloride is selectively 99.37%,
End reaction yield is 99.32% (product decomposes 0.68%), and side reaction is selectively 0.68%.
After step 3) is dry, the total recovery of solid hydroxylamine hydrochloride is 98.82%.
Embodiment three
The preparation method of the hydroxylamine hydrochloride of the present embodiment the following steps are included:
1) water of the butanone oxime hydrochloride of 122g and 288g are added in mixer and keep the temperature 45 DEG C, heat preservation 2h is sufficiently mixed
It is even, premixed liquid is made；
2) it takes the Titanium Sieve Molecular Sieve of 28g to be put into reaction kettle, the premixed liquid being uniformly mixed by step 1) is put into reaction
Kettle is warming up to 85 DEG C, reaction pressure 55KPa, reacts 9h, obtains hydroxylamine hydrochloride and by-product butanone；
3) it will be gone in crystallization cylinder by the hydroxylamine hydrochloride in step 2), crystallize the temperature in cylinder and control the reaction at 42 DEG C
Pressure is 55KPa, after crystallizing 11h, is separated by solid-liquid separation, is squeezed into closed filter with charge pump, by solid hydrochloric acid hydroxyl after cooling
Amine separation, the solid hydroxylamine hydrochloride isolated use pneumatic conveying drying, and drying temperature is 120 DEG C.The dust of pneumatic conveying drying passes through cloth
Bag dust collector dedusting, the dedusting product (hydroxylamine hydrochloride) that gets off return to product packaging process.
Wherein, the impurity diacetylmonoxime in the butanone and raw material after step 2) reaction by three-level condensation, (adopt by first order condensation
With 34 DEG C of condensed waters, second level condensation uses 8 DEG C of condensation water condensations, and the third level condenses -16 DEG C of condensation water condensations of use), condensation
Material afterwards enters in oil water separator, includes the process that water is back to use step 1) by the aqueous portion that oil water separator separates
In, the oil phase part separated point (butanone and diacetylmonoxime) in NaOH lye circulation in alkali cleaning knockout tower through 30% concentration and
Overflow is to alkali cleaning liquid bath afterwards, and upper layer aqueous solution (diacetylmonoxime) send to diacetylmonoxime and recycles station arrangement, by the alkali cleaning knockout tower alkali
Butanone and remaining diacetylmonoxime material after washing are sent to rectifying column rectifying, and rectifying column is by the way of steam jacket heating, temperature
It is 115 DEG C, pressure is 5100Pa, rectifying 2.5h in rectifying column.The butanone that rectifying is isolated condenses (first order condensation by three-level
Using 34 DEG C of condensed waters, second level condensation uses 8 DEG C of condensation water condensations, and the third level condenses -16 DEG C of condensation water condensations of use) it uses afterwards
In production diacetylmonoxime, distills the diacetylmonoxime isolated and send to diacetylmonoxime recyclable device, fixed gas discharge, materials at bottom of tower passes through oxime water
Pump is delivered to oxime water recovery device.
In addition, the catalyst (Titanium Sieve Molecular Sieve) in step 2) reaction tower is periodically added in reaction kettle, catalyst is followed
After the time that one of ring, a certain amount of catalyst will be generated and be discharged from the bottom of reaction kettle.
In step 2), in terms of butanone oxime hydrochloride, reaction conversion ratio 100%, hydroxylamine hydrochloride is selectively 99.27%,
End reaction yield is 99.27% (product decomposes 0.73%), and side reaction is selectively 0.73%.
After step 3) is dry, the total recovery of solid hydroxylamine hydrochloride is 98.73%.
Taking the above-mentioned ideal embodiment according to the present invention as inspiration, through the above description, relevant staff
Various changes and amendments can be carried out without departing from the scope of the present invention completely.The technical scope of this invention is not
The content being confined on specification, it is necessary to which the technical scope thereof is determined according to the scope of the claim.
Claims (10)
1. a kind of preparation method of hydroxylamine hydrochloride, which is characterized in that itself the following steps are included:
1) in 40~45 DEG C of 1~2h of heat preservation after mixing butanone oxime hydrochloride and water, premixed liquid is obtained；The butanone oxime hydrochloride with
The molar ratio of water are as follows: 1:7~16；
2) premixed liquid in step 1) and catalyst Ti-si molecular sieves obtain after mixing after 75~85 DEG C of 7~9h of reaction
Hydroxylamine hydrochloride and by-product butanone；
3) by hydroxylamine hydrochloride in step 2) go in crystallization cylinder and crystallized to obtain the final product.
2. the preparation method of hydroxylamine hydrochloride as described in claim 1, it is characterised in that: reaction in step 2) is 45 in pressure
It is carried out under conditions of~55KPa.
3. the preparation method of hydroxylamine hydrochloride as described in claim 1, it is characterised in that: in the butanone and raw material in step 2)
Impurity diacetylmonoxime by condenser condense after recycle.
4. the preparation method of hydroxylamine hydrochloride as claimed in claim 3, it is characterised in that: the condenser is condensed into three-level condensation
It is cooling, the condition of the three-level condensation are as follows: first order condensation uses 30~34 DEG C of condensed waters, and second level condensation is cold using 6~8 DEG C
Condensate, -13~-16 DEG C of condensed waters of third level use.
5. the preparation method of hydroxylamine hydrochloride as claimed in claim 3, it is characterised in that: the impurity in the butanone and raw material
Diacetylmonoxime enters oil water separator after condensation, and the water phase that the oil water separator is isolated includes water, is back to use step 1)
Process in；The oil phase part that the grease current divider is isolated point includes butanone and diacetylmonoxime, by alkali cleaning knockout tower alkali cleaning, on
Diacetylmonoxime in layer aqueous solution send to diacetylmonoxime and recycles station arrangement, butanone after the alkali cleaning knockout tower alkali cleaning and remaining
Diacetylmonoxime send to rectifying column rectifying and separates.
6. the preparation method of hydroxylamine hydrochloride as claimed in claim 5, it is characterised in that: the temperature of the rectifying column be 105~
115 DEG C, pressure is 4900~5100Pa in rectifying column, and the rectifying time is 1.5~2.5h.
7. hydroxylamine hydrochloride as described in claim 1, it is characterised in that: the temperature control in the step 3) in crystallization cylinder exists
38-42 DEG C, reaction pressure 45-55KPa, crystallization time 9-11h.
8. the preparation method of hydroxylamine hydrochloride as described in claim 1, it is characterised in that: the hydroxylamine hydrochloride warp in the step 3)
Solid hydroxylamine hydrochloride is made in drying technique after crossing crystallization.
9. the preparation method of hydroxylamine hydrochloride as claimed in claim 8, it is characterised in that: the drying process is dry using air-flow
Dry, temperature is 100-120 DEG C in drier.
10. the preparation method of hydroxylamine hydrochloride as claimed in claim 5, it is characterised in that: the lye in the alkali cleaning knockout tower
For NaOH lye.
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| CN201811502067.XA CN109573967A (en) | 2018-12-10 | 2018-12-10 | A kind of preparation method of hydroxylamine hydrochloride |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111056970A (en) * | 2019-12-23 | 2020-04-24 | 浙江锦华新材料股份有限公司 | Method for removing residual methyl tributyroximo silane in butanone oxime hydrochloride |
| CN111116411A (en) * | 2019-12-23 | 2020-05-08 | 浙江锦华新材料股份有限公司 | Method for removing residual methyl tributyroximo silane in butanone oxime hydrochloride |
| CN111204722A (en) * | 2020-03-12 | 2020-05-29 | 浙江锦华新材料股份有限公司 | Preparation method of solid hydroxylamine hydrochloride |
| CN113023693A (en) * | 2019-12-24 | 2021-06-25 | 江苏长青农化股份有限公司 | Processing method for improving purity of hydroxylamine hydrochloride |
| CN113620494A (en) * | 2021-08-18 | 2021-11-09 | 江苏艾科维科技有限公司 | Low COD treatment of waste water and method for recovering hexahydropyridine in waste water |
-
2018
- 2018-12-10 CN CN201811502067.XA patent/CN109573967A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111056970A (en) * | 2019-12-23 | 2020-04-24 | 浙江锦华新材料股份有限公司 | Method for removing residual methyl tributyroximo silane in butanone oxime hydrochloride |
| CN111116411A (en) * | 2019-12-23 | 2020-05-08 | 浙江锦华新材料股份有限公司 | Method for removing residual methyl tributyroximo silane in butanone oxime hydrochloride |
| CN111116411B (en) * | 2019-12-23 | 2022-10-18 | 浙江锦华新材料股份有限公司 | Method for removing residual methyl tributyrinoxime silane in butanone oxime hydrochloride |
| CN111056970B (en) * | 2019-12-23 | 2022-10-18 | 浙江锦华新材料股份有限公司 | Method for removing residual methyl tributyroximo silane in butanone oxime hydrochloride |
| CN113023693A (en) * | 2019-12-24 | 2021-06-25 | 江苏长青农化股份有限公司 | Processing method for improving purity of hydroxylamine hydrochloride |
| CN111204722A (en) * | 2020-03-12 | 2020-05-29 | 浙江锦华新材料股份有限公司 | Preparation method of solid hydroxylamine hydrochloride |
| CN111204722B (en) * | 2020-03-12 | 2021-04-02 | 浙江锦华新材料股份有限公司 | Preparation method of solid hydroxylamine hydrochloride |
| CN113620494A (en) * | 2021-08-18 | 2021-11-09 | 江苏艾科维科技有限公司 | Low COD treatment of waste water and method for recovering hexahydropyridine in waste water |
| CN113620494B (en) * | 2021-08-18 | 2023-06-13 | 江苏艾科维科技股份有限公司 | Method for reducing COD in wastewater and recovering piperidine in wastewater |
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Application publication date: 20190405 |