CN105693604A - Production technique of halquinol - Google Patents
Production technique of halquinol Download PDFInfo
- Publication number
- CN105693604A CN105693604A CN201610194337.XA CN201610194337A CN105693604A CN 105693604 A CN105693604 A CN 105693604A CN 201610194337 A CN201610194337 A CN 201610194337A CN 105693604 A CN105693604 A CN 105693604A
- Authority
- CN
- China
- Prior art keywords
- halquinol
- halogenation
- obtains
- temperature
- hydrochloric acid
- 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.)
- Pending
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- XCQBENAYFZFNAR-UHFFFAOYSA-N 5-chloroquinolin-8-ol;7-chloroquinolin-8-ol;5,7-dichloroquinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1.C1=CN=C2C(O)=C(Cl)C=CC2=C1.C1=CN=C2C(O)=C(Cl)C=C(Cl)C2=C1 XCQBENAYFZFNAR-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000026030 halogenation Effects 0.000 claims abstract description 12
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 12
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 6
- 238000010298 pulverizing process Methods 0.000 claims abstract description 5
- 238000004806 packaging method and process Methods 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims abstract description 4
- 238000001291 vacuum drying Methods 0.000 claims abstract description 4
- 238000005516 engineering process Methods 0.000 claims description 12
- 230000008014 freezing Effects 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000006386 neutralization reaction Methods 0.000 abstract 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 abstract 2
- 229960002163 hydrogen peroxide Drugs 0.000 abstract 2
- 229960003540 oxyquinoline Drugs 0.000 abstract 2
- 238000005057 refrigeration Methods 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UZSGWJQJDLCCFN-UHFFFAOYSA-N 2-acetylbenzonitrile Chemical compound CC(=O)C1=CC=CC=C1C#N UZSGWJQJDLCCFN-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000008738 huangbai Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003248 quinolines Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a production technique of halquinol. The method comprises the following steps: halogenation: adding 8-hydroxyquinoline and 30 wt% hydrochloric acid into a reaction kettle, dropwisely adding oxydol while controlling the temperature at 60 DEG C or below, and keeping the temperature for 2 hours after finishing the dropwise addition, thereby obtaining a halogenation solution, wherein the mass ratio of the 8-hydroxyquinoline, 30 wt% hydrochloric acid and oxydol is 2:3:1; neutralization: dropwisely adding liquid caustic soda into the halogenation solution to regulate the pH value to 7, thereby obtaining a neutralization solution; refrigeration and centrifugation: cooling the neutralization solution to 3-6 DEG C to perform crystallization, and centrifuging to obtain a wet product; drying: carrying out vacuum drying on the wet product at 60 DEG C or below until the water content is less than 0.5%; and pulverization: pulverizing the dried solid, and packaging to obtain the finished product halquinol. By adding the refrigeration and centrifugation process, the technique is simplified, and the energy consumption is saved.
Description
Technical field
The present invention relates to medicine synthesis technical field, particularly relate to the production technology of a kind of halquinol。
Background technology
Halquinol, English name is Halquinol, and molecular formula is C9H7NO.Cln, it is HUANGBAI(sic) to yellow-gray powder。Halquinol is a kind of feed additive, it it is quinolines, antibiotic antibacterial is taken through what chlorination synthesized for oxine, there is nonspecific chelation, the metal ion making antibacterial cannot utilize necessity can be combined, thus reaching the effect of bacteria growing inhibiting and breeding with important metallic；Halquinol may interfere with the synthesis of fungal cell wall, it is suppressed that fungus growth, breeding。
Summary of the invention
The technical problem that present invention mainly solves is to provide the production technology of a kind of halquinol, adds frozen centrifugation technology, simplifies technique, save energy consumption。
For solving above-mentioned technical problem, the technical scheme that the present invention adopts is:
The production technology of a kind of halquinol is provided, comprises the steps:
1) halogenation, adds the hydrochloric acid of oxine and 30% mass fraction in reactor, controls temperature and drips hydrogen peroxide below 60 DEG C, is incubated 2h, obtains halogenation liquid after dripping off；Oxine, the hydrochloric acid of 30% mass fraction and the mass ratio of hydrogen peroxide are 2:3:1；
2) neutralizing, drip liquid caustic soda in step 1) gained halogenation liquid, regulating pH value is 7, obtains neutralizer；
3) freezing, centrifugal, by step 2) temperature of neutralizer that obtains is reduced to 3 ~ 6 DEG C of crystallizes, centrifugal, obtains wet product；
4) dry, the wet product that step 3) is obtained below 60 DEG C vacuum drying to wherein moisture less than 0.5%；
5) pulverizing, after being pulverized by solid dried for step 4), packaging, obtains finished product halquinol。
In a preferred embodiment of the present invention, step 2) in the mass fraction of described liquid caustic soda be 30 ~ 35%。
In a preferred embodiment of the present invention, the temperature at neutralizer described in step 3) is reduced to 5 DEG C and carries out crystallize。
The invention has the beneficial effects as follows: the production technology of a kind of halquinol of the present invention, add frozen centrifugation technology, simplify technique, save energy consumption, improve yield。
Accompanying drawing explanation
Fig. 1 is the technological process of production sketch of a preferred embodiment of the present invention。
Detailed description of the invention
Below in conjunction with accompanying drawing, presently preferred embodiments of the present invention is described in detail, so that advantages and features of the invention can be easier to be readily appreciated by one skilled in the art, thus protection scope of the present invention being made apparent clear and definite defining。
The production technology of a kind of halquinol, comprises the steps:
1) halogenation, adds the hydrochloric acid of oxine and 30% mass fraction in reactor, controls temperature and drips hydrogen peroxide below 60 DEG C, is incubated 2h, obtains halogenation liquid after dripping off；Oxine, the hydrochloric acid of 30% mass fraction and the mass ratio of hydrogen peroxide are 2:3:1；
2) neutralizing, dripping mass fraction in step 1) gained halogenation liquid is the liquid caustic soda of 32%, and regulating pH value is 7, obtains neutralizer；
3) freezing, centrifugal, by step 2) temperature of neutralizer that obtains is reduced to 5 DEG C of crystallizes, centrifugal, obtains wet product；
4) dry, the wet product that step 3) is obtained below 60 DEG C vacuum drying to wherein moisture less than 0.5%；
5) pulverizing, after being pulverized by solid dried for step 4), packaging, obtains finished product halquinol。
The yield of the finished product halquinol that the present invention is last reaches more than 76%。
The foregoing is only embodiments of the invention; not thereby the scope of the claims of the present invention is limited; every equivalent structure utilizing description of the present invention and accompanying drawing content to make or equivalence flow process conversion; or directly or indirectly it is used in other relevant technical fields, all in like manner include in the scope of patent protection of the present invention。
Claims (3)
1. the production technology of a halquinol, it is characterised in that comprise the steps:
1) halogenation, adds the hydrochloric acid of oxine and 30% mass fraction in reactor, controls temperature and drips hydrogen peroxide below 60 DEG C, is incubated 2h, obtains halogenation liquid after dripping off；Oxine, the hydrochloric acid of 30% mass fraction and the mass ratio of hydrogen peroxide are 2:3:1；
2) neutralizing, drip liquid caustic soda in step 1) gained halogenation liquid, regulating pH value is 7, obtains neutralizer；
3) freezing, centrifugal, by step 2) temperature of neutralizer that obtains is reduced to 3 ~ 6 DEG C of crystallizes, centrifugal, obtains wet product；
4) dry, the wet product that step 3) is obtained below 60 DEG C vacuum drying to wherein moisture less than 0.5%；
5) pulverizing, after being pulverized by solid dried for step 4), packaging, obtains finished product halquinol。
2. the production technology of halquinol according to claim 1, it is characterised in that step 2) in the mass fraction of described liquid caustic soda be 30 ~ 35%。
3. the production technology of halquinol according to claim 1, it is characterised in that the temperature at neutralizer described in step 3) is reduced to 5 DEG C and carries out crystallize。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610194337.XA CN105693604A (en) | 2016-03-31 | 2016-03-31 | Production technique of halquinol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610194337.XA CN105693604A (en) | 2016-03-31 | 2016-03-31 | Production technique of halquinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105693604A true CN105693604A (en) | 2016-06-22 |
Family
ID=56218092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610194337.XA Pending CN105693604A (en) | 2016-03-31 | 2016-03-31 | Production technique of halquinol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105693604A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115784985A (en) * | 2022-12-01 | 2023-03-14 | 郑州原理生物科技有限公司 | A kind of preparation method of halquinol |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1405155A (en) * | 2002-11-04 | 2003-03-26 | 卢宪春 | 5-chloro-8-hydroxyquinoline preparation method |
-
2016
- 2016-03-31 CN CN201610194337.XA patent/CN105693604A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1405155A (en) * | 2002-11-04 | 2003-03-26 | 卢宪春 | 5-chloro-8-hydroxyquinoline preparation method |
Non-Patent Citations (2)
| Title |
|---|
| 张珍明 等: "氧氯化法制备5 -氯-8 -羟基喹啉的研究", 《化工时刊》 * |
| 蔡敏 等: "HPLC法测定哈喹诺中5,7-二氯-8-羟基喹啉、5-氯-8-羟基喹啉和7-氯-8-羟基喹啉的含量", 《中国畜牧兽医学会动物药品学分会2008学术年会论文集》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115784985A (en) * | 2022-12-01 | 2023-03-14 | 郑州原理生物科技有限公司 | A kind of preparation method of halquinol |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160622 |