CN106977509B - The multiple water law method for crystallising of thiamine hydrochloride - Google Patents
The multiple water law method for crystallising of thiamine hydrochloride Download PDFInfo
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- CN106977509B CN106977509B CN201710195515.5A CN201710195515A CN106977509B CN 106977509 B CN106977509 B CN 106977509B CN 201710195515 A CN201710195515 A CN 201710195515A CN 106977509 B CN106977509 B CN 106977509B
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- filtrate
- thiamine hydrochloride
- filter residue
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- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 title claims abstract description 58
- 229960000344 thiamine hydrochloride Drugs 0.000 title claims abstract description 58
- 235000019190 thiamine hydrochloride Nutrition 0.000 title claims abstract description 58
- 239000011747 thiamine hydrochloride Substances 0.000 title claims abstract description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000000706 filtrate Substances 0.000 claims abstract description 64
- 238000005406 washing Methods 0.000 claims abstract description 31
- 238000002425 crystallisation Methods 0.000 claims abstract description 29
- 239000005457 ice water Substances 0.000 claims abstract description 29
- 230000008025 crystallization Effects 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 17
- 238000001914 filtration Methods 0.000 claims abstract description 13
- 239000008213 purified water Substances 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 5
- 238000004090 dissolution Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 239000000047 product Substances 0.000 claims description 30
- 239000002994 raw material Substances 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000908 ammonium hydroxide Substances 0.000 claims description 5
- 238000010583 slow cooling Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 2
- UQQCAXMSWRLMQP-UHFFFAOYSA-N Cl.[S] Chemical compound Cl.[S] UQQCAXMSWRLMQP-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 20
- WNCAVNGLACHSRZ-KAMYIIQDSA-N Allithiamine Chemical compound C=CCSSC(/CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N WNCAVNGLACHSRZ-KAMYIIQDSA-N 0.000 description 2
- WNCAVNGLACHSRZ-UHFFFAOYSA-N Allithiamine Natural products C=CCSSC(CCO)=C(C)N(C=O)CC1=CN=C(C)N=C1N WNCAVNGLACHSRZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 150000003544 thiamines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a kind of multiple water crystallization technique of thiamine hydrochloride, include the following steps: Temperature fall after thiamine hydrochloride crude product and purified water heating stirring to thiamine hydrochloride dissolution, cooled down again with ice water and keeps the temperature crystallization and filtration, filtrate I and filter residue I are obtained, filter residue I obtains thiamine hydrochloride with ethanol washing；Filtrate I is concentrated, stirs I Temperature fall of filtrate, then cooled down with ice water and keep the temperature crystallization and filtration, filter to get filtrate II and filter residue II, and filter residue II obtains thiamine hydrochloride with ethanol washing；Filtrate II is concentrated, stirs Temperature fall after filtrate I, then cooled down with ice water and keep the temperature crystallization and filtration, filter to get filtrate III and filter residue III, and filter residue III obtains thiamine hydrochloride with ethanol washing.The present invention replaces alcohol method to crystallize using the crystallization of multiple water law, improves the yield of thiamine hydrochloride；The natural deposited dry density of thiamine hydrochloride can also be promoted simultaneously from 0.20 to 0.56g/mL, dramatically improve the natural deposited dry density of thiamine hydrochloride.
Description
Technical field
The invention belongs to the method for crystallising of thiamine hydrochloride, are more particularly to a kind of side of the multiple water law crystallization of thiamine hydrochloride
Method.
Background technique
Existing thiamine hydrochloride alcohol crystal need to consume a large amount of ethyl alcohol, higher cost；And the hydrochloric acid for passing through alcohol crystal
Thiamines, natural deposited dry density is smaller, influences the quality of thiamine hydrochloride.
Summary of the invention
The object of the present invention is to provide one kind, cost is relatively low and the multiple water law of the higher thiamine hydrochloride of bulk density crystallizes
Method.
According to an aspect of the invention, there is provided a kind of multiple water crystallization technique of thiamine hydrochloride, which is characterized in that packet
Include following steps:
Temperature fall after thiamine hydrochloride crude product and purified water being stirred at a temperature of 60 DEG C~70 DEG C to thiamine hydrochloride dissolution
8 DEG C~12 DEG C are cooled to 25 DEG C~27 DEG C, then with ice water, 15min~25min crystallization and filtration is kept the temperature, obtains filtrate I and filter residue
I, filter residue I obtains thiamine hydrochloride with ethanol washing；
Filtrate I is concentrated, is naturally cooling to 20 DEG C~30 after stirring I 15min of filtrate~25min at a temperature of 45 DEG C~55 DEG C
DEG C, then be cooled to 8 DEG C~12 DEG C with ice water and keep the temperature 15min~25min crystallization and filtration, filter to get filtrate II and filter residue II,
Filter residue II obtains thiamine hydrochloride with ethanol washing；
Be concentrated filtrate II, at a temperature of 45 DEG C~55 DEG C stir I 15min of filtrate~25min after be naturally cooling to 20 DEG C~
30 DEG C, then be cooled to 8 DEG C~12 DEG C with ice water and keep the temperature 15min~25min crystallization and filtration, filter to get filtrate III and filter residue
III, filter residue III obtains thiamine hydrochloride with ethanol washing.
A kind of multiple water crystallization technique of thiamine hydrochloride, includes the following steps:
Temperature fall after thiamine hydrochloride crude product and purified water being stirred at a temperature of 60 DEG C~70 DEG C to thiamine hydrochloride dissolution
10 DEG C are cooled to 25 DEG C, then with ice water, is filtered after keeping the temperature 20min, obtains filtrate I and filter residue I, filter residue I obtains salt with ethanol washing
Allithiamine；
Filtrate I is concentrated, is naturally cooling to 25 DEG C after stirring I 20min of filtrate at 50 °C, then be cooled to 10 with ice water
DEG C and keep the temperature 20min, filter to get filtrate II and filter residue II, and filter residue II obtains thiamine hydrochloride with ethanol washing；
Filtrate II is concentrated, is naturally cooling to 25 DEG C after stirring I 20min of filtrate at 50 °C, then be cooled to ice water
10 DEG C and 20min is kept the temperature, filter to get filtrate III and filter residue III, and filter residue III obtains thiamine hydrochloride with ethanol washing.
In some embodiments, the filtrate III is for producing as subcrystalline raw material again, comprising:
Filtrate III is reacted with ammonium nitrate, ammonium hydroxide, is cooled to 8 DEG C after reaction, resulting filter residue first is filtered in filtering
Dry product I is dried to obtain after alcohol washing；
The dry product I is reacted with methanol, sour methanol, after reaction, slow cooling is cooled to 25 DEG C, then with ice water
15 DEG C, the raw material that resulting filter residue methanol washing and drying must be used to crystallize again is filtered in filtering.
In some embodiments, concentration filtrate I to solid-liquid mass ratio is 100:74~76.
In some embodiments, concentration filtrate II to solid-liquid mass ratio is 100:74~76.
It has the advantage that: the present invention replaces alcohol method to crystallize using the crystallization of multiple water law, the yield of thiamine hydrochloride is improved；
Filter residue is made to the raw material recrystallized, 20% cost is reduced on raw material；It is crystallized by multiple water law, it can also be by salt
The natural deposited dry density of allithiamine is promoted from 0.20 to 0.56g/mL, and the natural packing for dramatically improving thiamine hydrochloride is close
Degree.
Specific embodiment
Embodiment 1
200g thiamine hydrochloride is added in three-necked flask, three-necked flask is put into 60 DEG C~70 DEG C of water by 152g purified water
In bath, stirring is completely dissolved thiamine hydrochloride, closes the heater switch of water-bath, makes three-necked flask whole system with water-bath
Cool down slowly together.When temperature drops to 25 DEG C or so, 10 DEG C are down to ice water, and keep the temperature 20min.Filter to get filtrate I and filter
Slag I, filtrate I are stand-by, dried after the 30g ethanol washing of filter residue I weight be 72.43g thiamine hydrochloride, yield 36.22%,
Quality analysis is qualified, and the bulk density of finished product is promoted to 0.5g/mL by the 0.2g/mL of raw material.
It is 100:76 that filtrate I, which is concentrated into solid-liquid mass ratio by Rotary Evaporators at 50 DEG C, then is transferred to three mouthfuls
In flask, in the water-bath of 50 DEG C of merging, 20min is stirred, the heater switch of water-bath is closed, makes it with water-bath Temperature fall.
When temperature is reduced to 25 DEG C or so, 10 DEG C are cooled to ice water, keeps the temperature 20min.Filter to get filtrate II and filter residue II, filter residue II
With dried after 20g ethanol washing weight be 42.5g thiamine hydrochloride, yield 21.25%, quality analysis is qualified, finished product
Bulk density is promoted to 0.54g/mL by the 0.5g/mL of raw material.
It is 100:76 that filtrate II, which is concentrated into solid-liquid mass ratio by Rotary Evaporators at 50 DEG C, is being transferred to three mouthfuls
It in flask, is placed in 50 DEG C of water-bath, stirs 20min, close the heater switch of water-bath, make it with water-bath Temperature fall.
When temperature drops to 25 DEG C or so, 10 DEG C are down to ice water, and keep the temperature 20min.Filter to get filtrate III and filter residue III, and filter residue III is used
Thiamine hydrochloride of the weight for 20.84g is dried to obtain after 10g ethanol washing, yield 10.42%, quality analysis is qualified, the heap of finished product
Product density is promoted to 0.56g/mL by the 0.54g/mL of raw material.
The joint yield of three step water crystallizations is 67.89%.
By filtrate III and ammonium nitrate, ammonium hydroxide reaction, after reaction, 8 DEG C is cooled to, filters resulting filter residue IV and use 30g
It is dried after methanol washing, obtains 55.23g dry product I.
55.23g dry product and methanol, sour methanol are reacted, after reaction, when slow cooling is to 25 DEG C or so, then use ice
Water is cooled to 15 DEG C.The dry product II for the 55.78g that resulting filter residue is washed and dried with 30g methanol is filtered, quality analysis is qualified.
Raw material of the dry product II as water crystallization, repeating the above steps carries out three step water crystallization methods again and crystallizes to it,
The comprehensive utilization ratio of raw material is 95.8%.
Embodiment 2
200g thiamine hydrochloride is added in three-necked flask, three-necked flask is put into 60 DEG C~70 DEG C of water by 152g purified water
In bath, stirring is completely dissolved thiamine hydrochloride, closes the heater switch of water-bath, makes three-necked flask whole system with water-bath
Cool down slowly together.When temperature drops to 27 DEG C or so, 12 DEG C are down to ice water, and keep the temperature 25min.Filter to get filtrate I and filter
Slag I, filtrate I are stand-by, dried after the 30g ethanol washing of filter residue I weight be 73.56g thiamine hydrochloride, yield 36.78%,
Quality analysis is qualified, and the bulk density of finished product is promoted to 0.5g/mL by the 0.2g/mL of raw material.
It is 100:74 that filtrate I, which is concentrated into solid-liquid mass ratio by Rotary Evaporators at 50 DEG C, then is transferred to three mouthfuls
In flask, in the water-bath of 50 DEG C of merging, 15min is stirred, the heater switch of water-bath is closed, makes it with water-bath Temperature fall.
When temperature is reduced to 25 DEG C or so, 8 DEG C are cooled to ice water, keeps the temperature 15min.Filter to get filtrate II and filter residue II, filter residue II
With dried after 20g ethanol washing weight be 42.8g thiamine hydrochloride, yield 21.4%, quality analysis is qualified, the heap of finished product
Product density is promoted to 0.52g/mL by the 0.5g/mL of raw material.
It is 100:78 that filtrate II, which is concentrated into solid-liquid mass ratio by Rotary Evaporators at 50 DEG C, is being transferred to three mouthfuls
It in flask, is placed in 50 DEG C of water-bath, stirs 25min, close the heater switch of water-bath, make it with water-bath Temperature fall.
When temperature drops to 30 DEG C or so, 12 DEG C are down to ice water, and keep the temperature 25min.Filter to get filtrate III and filter residue III, and filter residue III is used
Thiamine hydrochloride of the weight for 22.04g is dried to obtain after 10g ethanol washing, yield 11.02%, quality analysis is qualified, the heap of finished product
Product density is promoted to 0.56g/mL by the 0.52g/mL of raw material.
The joint yield of three step water crystallizations is 69.2%.
By filtrate III and ammonium nitrate, ammonium hydroxide reaction, after reaction, 8 DEG C is cooled to, filters resulting filter residue IV and use 30g
It is dried after methanol washing, obtains 56.04g dry product I.
56.04g dry product and methanol, sour methanol are reacted, after reaction, when slow cooling is to 25 DEG C or so, then use ice
Water is cooled to 15 DEG C.The dry product II for the 55.18g that resulting filter residue is washed and dried with 30g methanol is filtered, quality analysis is qualified.
Raw material of the dry product II as water crystallization, repeating the above steps carries out three step water crystallization methods again and crystallizes to it,
The comprehensive utilization ratio of raw material is 96.5%.
Embodiment 1
200g thiamine hydrochloride is added in three-necked flask, three-necked flask is put into 60 DEG C~70 DEG C of water by 152g purified water
In bath, stirring is completely dissolved thiamine hydrochloride, closes the heater switch of water-bath, makes three-necked flask whole system with water-bath
Cool down slowly together.When temperature drops to 27 DEG C or so, 12 DEG C are down to ice water, and keep the temperature 25min.Filter to get filtrate I and filter
Slag I, filtrate I are stand-by, dried after the 30g ethanol washing of filter residue I weight be 72.02g thiamine hydrochloride, yield 36.01%,
Quality analysis is qualified, and the bulk density of finished product is promoted to 0.5g/mL by the 0.2g/mL of raw material.
It is 100:74 that filtrate I, which is concentrated into solid-liquid mass ratio by Rotary Evaporators at 50 DEG C, then is transferred to three mouthfuls
In flask, in the water-bath of 45 DEG C of merging, 15min is stirred, the heater switch of water-bath is closed, makes it with water-bath Temperature fall.
When temperature is reduced to 20 DEG C or so, 8 DEG C are cooled to ice water, keeps the temperature 15min.Filter to get filtrate II and filter residue II, filter residue II
With dried after 20g ethanol washing weight be 43.6g thiamine hydrochloride, yield 21.8%, quality analysis is qualified, the heap of finished product
Product density is promoted to 0.53g/mL by the 0.5g/mL of raw material.
It is 100:78 that filtrate II, which is concentrated into solid-liquid mass ratio by Rotary Evaporators at 50 DEG C, is being transferred to three mouthfuls
It in flask, is placed in 45 DEG C of water-bath, stirs 15min, close the heater switch of water-bath, make it with water-bath Temperature fall.
When temperature drops to 25 DEG C or so, 11 DEG C are down to ice water, and keep the temperature 20min.Filter to get filtrate III and filter residue III, and filter residue III is used
Thiamine hydrochloride of the weight for 21.24g is dried to obtain after 10g ethanol washing, yield 10.62%, quality analysis is qualified, the heap of finished product
Product density is promoted to 0.56g/mL by the 0.53g/mL of raw material.
The joint yield of three step water crystallizations is 68.43%.
By filtrate III and ammonium nitrate, ammonium hydroxide reaction, after reaction, 8 DEG C is cooled to, filters resulting filter residue IV and use 30g
It is dried after methanol washing, obtains 55.43g dry product I.
55.43g dry product and methanol, sour methanol are reacted, after reaction, when slow cooling is to 25 DEG C or so, then use ice
Water is cooled to 15 DEG C.The dry product II for the 56.87g that resulting filter residue is washed and dried with 30g methanol is filtered, quality analysis is qualified.
Raw material of the dry product II as water crystallization, repeating the above steps carries out three step water crystallization methods again and crystallizes to it,
The comprehensive utilization ratio of raw material is 96.7%.
Above-described is only some embodiments of the present invention.For those of ordinary skill in the art, it is not taking off
Under the premise of from the invention design, various modifications and improvements can be made, and these are all within the scope of protection of the present invention.
Claims (5)
1. the multiple water crystallization technique of thiamine hydrochloride, which comprises the steps of:
25 are naturally cooling to after thiamine hydrochloride crude product and purified water being stirred at a temperature of 60 DEG C~70 DEG C to thiamine hydrochloride dissolution
DEG C~27 DEG C, then 8 DEG C~12 DEG C are cooled to ice water, 15mi n~25mi n crystallization and filtration is kept the temperature, filtrate I and filter residue I are obtained,
Filter residue I obtains thiamine hydrochloride with ethanol washing；
Filtrate I is concentrated, is naturally cooling to 20 DEG C~30 after stirring I 15mi n~25mi n of filtrate at a temperature of 45 DEG C~55 DEG C
DEG C, then be cooled to 8 DEG C~12 DEG C with ice water and keep the temperature 15mi n~25mi n crystallization and filtration, filter to get filtrate II and filter residue
II, filter residue II obtains thiamine hydrochloride with ethanol washing；
Filtrate II is concentrated, is naturally cooling to 20 DEG C~30 after stirring I 15mi n~25mi n of filtrate at a temperature of 45 DEG C~55 DEG C
DEG C, then be cooled to 8 DEG C~12 DEG C with ice water and keep the temperature 15mi n~25mi n crystallization and filtration, filter to get filtrate III and filter residue
III, filter residue III obtains thiamine hydrochloride with ethanol washing.
2. the multiple water crystallization technique of thiamine hydrochloride according to claim 1, which comprises the steps of:
25 are naturally cooling to after thiamine hydrochloride crude product and purified water being stirred at a temperature of 60 DEG C~70 DEG C to thiamine hydrochloride dissolution
DEG C, then 10 DEG C are cooled to ice water, it is filtered after keeping the temperature 20mi n, obtains filtrate I and filter residue I, filter residue I obtains hydrochloric acid sulphur with ethanol washing
Amine；
Filtrate I is concentrated, is naturally cooling to 25 DEG C after stirring I 20mi n of filtrate at 50 °C, then be cooled to 10 DEG C with ice water
And 20mi n is kept the temperature, filter to get filtrate II and filter residue II, and filter residue II obtains thiamine hydrochloride with ethanol washing；
Filtrate II is concentrated, is naturally cooling to 25 DEG C after stirring I 20mi n of filtrate at 50 °C, then be cooled to 10 DEG C with ice water
And 20mi n is kept the temperature, filter to get filtrate III and filter residue III, and filter residue III obtains thiamine hydrochloride with ethanol washing.
3. the multiple water crystallization technique of thiamine hydrochloride according to claim 1, which is characterized in that the filtrate III is for making
It is taken as subcrystalline raw material again, comprising:
Filtrate III is reacted with ammonium nitrate, ammonium hydroxide, is cooled to 8 DEG C after reaction, filtering is filtered resulting filter residue and washed with methanol
Dry product I is dried to obtain after washing；
The dry product I is reacted with methanol, sour methanol, after reaction, slow cooling is cooled to 15 to 25 DEG C, then with ice water
DEG C, the raw material that resulting filter residue methanol washing and drying must be used to crystallize again is filtered in filtering.
4. the multiple water crystallization technique of thiamine hydrochloride according to claim 1, which is characterized in that concentration filtrate I to solid-liquid
Mass ratio is 100:74~78.
5. the multiple water crystallization technique of thiamine hydrochloride according to claim 1, which is characterized in that concentration filtrate II to solid-liquid
Mass ratio is 100:74~78.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102952126A (en) * | 2012-12-03 | 2013-03-06 | 华中药业股份有限公司 | Novel method for synthesizing vitamin B1 hydrochloride |
| CN104817551A (en) * | 2015-05-07 | 2015-08-05 | 常州大学 | New method of preparing vitamin B1 hydrochloride |
| CN105315272A (en) * | 2015-10-19 | 2016-02-10 | 天津大学 | Method for preparing thiamine hydrochloride crystal product |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102952126A (en) * | 2012-12-03 | 2013-03-06 | 华中药业股份有限公司 | Novel method for synthesizing vitamin B1 hydrochloride |
| CN104817551A (en) * | 2015-05-07 | 2015-08-05 | 常州大学 | New method of preparing vitamin B1 hydrochloride |
| CN105315272A (en) * | 2015-10-19 | 2016-02-10 | 天津大学 | Method for preparing thiamine hydrochloride crystal product |
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