CN106032360A - Preparation method of thiamine propyl disulfide - Google Patents
Preparation method of thiamine propyl disulfide Download PDFInfo
- Publication number
- CN106032360A CN106032360A CN201510105651.1A CN201510105651A CN106032360A CN 106032360 A CN106032360 A CN 106032360A CN 201510105651 A CN201510105651 A CN 201510105651A CN 106032360 A CN106032360 A CN 106032360A
- Authority
- CN
- China
- Prior art keywords
- prosultiamine
- preparation
- sodium
- solution
- high speed
- 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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Links
- UDCIYVVYDCXLSX-SDNWHVSQSA-N n-[(4-amino-2-methylpyrimidin-5-yl)methyl]-n-[(e)-5-hydroxy-3-(propyldisulfanyl)pent-2-en-2-yl]formamide Chemical compound CCCSS\C(CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N UDCIYVVYDCXLSX-SDNWHVSQSA-N 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 13
- 229950007142 prosultiamine Drugs 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000000839 emulsion Substances 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 11
- 239000004133 Sodium thiosulphate Substances 0.000 claims description 10
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 10
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 9
- GJNRIGCZVXQSHN-UHFFFAOYSA-M sodium;oxido-oxo-propoxy-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].CCCOS([O-])(=O)=S GJNRIGCZVXQSHN-UHFFFAOYSA-M 0.000 claims description 7
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims description 6
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000001099 ammonium carbonate Substances 0.000 claims description 6
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 6
- 238000005119 centrifugation Methods 0.000 claims description 6
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000012047 saturated solution Substances 0.000 claims description 6
- 229930003270 Vitamin B Natural products 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000011720 vitamin B Substances 0.000 claims description 3
- 235000019156 vitamin B Nutrition 0.000 claims description 3
- 239000011691 vitamin B1 Substances 0.000 claims description 3
- SNDJGKIVHKOEHY-UHFFFAOYSA-M S(=S)(=O)(O)O.S[Na] Chemical compound S(=S)(=O)(O)O.S[Na] SNDJGKIVHKOEHY-UHFFFAOYSA-M 0.000 claims 2
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000001804 emulsifying effect Effects 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 230000002860 competitive effect Effects 0.000 abstract 1
- 238000010008 shearing Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 150000003722 vitamin derivatives Chemical class 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a preparation method of thiamine propyl disulfide. According to the preparation method, a high speed shearing and emulsifying reactor is adopted to replace the conventional phase transfer catalyst so as to make solid raw materials and liquid raw materials carry out reactions fully. The cost is reduced, and the production efficiency is improved. The preparation of thiamine propyl disulfide becomes simpler and feasible, and the competitive capacity of enterprises is improved.
Description
Technical field
The present invention relates to field of medicine and chemical technology, the concrete preparation method about a kind of prosultiamine.
Background technology
At present, in the preparation process of prosultiamine, need first to prepare sodium n-propyl thiosulfate, and prepare
Sodium n-propyl thiosulfate be then have employed phase transfer catalyst PEG400 to accelerate solid-liquid biphase between
Reaction, simultaneously need to average reaction time is 3 hours.But the phase transfer catalyst price in the method
Costliness, significantly increases production cost, when using the reaction that phase transfer catalyst also add raw material simultaneously
Between, the most indirectly reduce production efficiency.
Summary of the invention
It is an object of the invention to provide a kind of can reduce cost, improve efficiency, simple prosultiamine
Preparation method.
For solving above-mentioned technical problem, present invention employs following technical scheme: the system of a kind of prosultiamine
Preparation Method, comprises the following steps that
Step one, Sodium Thio Sulphate(Anhydrous) and n-Propyl Bromide are put in high speed shear emulsion reaction device, adjust
The rotating speed of joint high speed shear emulsion reaction device is 8000～10000r/min, then heats, and carries out backflow anti-
Should, filter to obtain sodium n-propyl thiosulfate filtrate；
Step 2, add vitamin B in a kettle.1, add pure water stirring and dissolving, and be maintained at 15～
It is passed through sodium hydroxide solution at a temperature of 20 DEG C, reaches 11～12 to pH value, continue insulated and stirred 1.5 hours
After, it is filtrated to get open loop solution by centrifuge；
Step 3, the open loop solution obtained in step 2 is passed through in reactor, then will step one obtain
Solution is slowly added dropwise to reactor, and stirring is to separating out solids；
After step 4, by centrifugation machine filter, the hydrochloric acid adding excess makes solids fully dissolve, mistake again
After filter, filtrate add ammonium carbonate saturated solution to precipitation no longer produce, after sucking filtration, by filtration cakes torrefaction,
To prosultiamine crude product；
Step 5, by prosultiamine crude product dehydrated alcohol recrystallization 2 times, obtain prosultiamine essence after drying
Product.
As the preferred version of prosultiamine preparation method of the present invention, wherein said reflux time is 2
Hour.
As the preferred version of prosultiamine preparation method of the present invention, wherein said high speed shear emulsifying is anti-
The rotating speed answering device is 9000r/min.
As the preferred version of prosultiamine preparation method of the present invention, wherein said pure water is distilled water.
As the preferred version of prosultiamine preparation method of the present invention, wherein said Sodium Thio Sulphate(Anhydrous)
With vitamin B1Mass ratio be 1:2～1:2.5.
As the preferred version of prosultiamine preparation method of the present invention, wherein said Sodium Thio Sulphate(Anhydrous)
It is 1:1～1.5:1 with the mass ratio of n-Propyl Bromide.
Compared with prior art, there is advantages that
One, reduce cost, not in use by expensive phase transfer catalyst, reduce cost, knock down price, carry
High competitiveness.
Two, improve production efficiency, drastically reduce the area the response time of raw material, shorten preparation time, from
And improve production efficiency.
Three, simple, the function of phase transfer catalyst is replaced with high speed shear emulsion reaction device, it is not necessary to
Add water as carrier, allow direct reaction between raw material.
Detailed description of the invention
For technological means that the present invention use and the technique effect that reach are expanded on further, below in conjunction with concrete real
Execute example the present invention is described in detail.Wherein r/min represents rev/min.
The invention provides the preparation method of a kind of prosultiamine, it comprises the following steps that
Step one, Sodium Thio Sulphate(Anhydrous) and n-Propyl Bromide are put in high speed shear emulsion reaction device, adjust
The rotating speed of joint high speed shear emulsion reaction device is 8000～10000r/min, then heats, and carries out backflow anti-
Should, it is filtrated to get solution；
Step 2, add vitamin B in a kettle.1, add pure water stirring and dissolving, and be maintained at 15～
It is passed through sodium hydroxide solution at a temperature of 20 DEG C, reaches 11～12 to pH value, continue insulated and stirred 1.5 hours
After, it is filtrated to get open loop solution by centrifuge；
Step 3, the open loop solution obtained in step 2 is passed through in reactor, then will step one obtain
Solution is slowly added dropwise to reactor, and stirring is to separating out solids；
After step 4, by centrifugation machine filter, the hydrochloric acid adding excess makes solids fully dissolve, mistake again
After filter, filtrate add ammonium carbonate saturated solution to precipitation no longer produce, after sucking filtration, by filtration cakes torrefaction,
To prosultiamine crude product；
Step 5, by prosultiamine crude product dehydrated alcohol recrystallization 2 times, obtain prosultiamine essence after drying
Product.
Reflux time in above-mentioned steps one is 2 hours, and the rotating speed of high speed shear emulsion reaction device is
9000r/min.Pure water in step 2 uses distilled water.Sodium Thio Sulphate(Anhydrous) and the quality of n-Propyl Bromide
Ratio is 1:1～1.5:1.Sodium Thio Sulphate(Anhydrous) and vitamin B1Mass ratio be 1:2～1:2.5.
Embodiment one
The Sodium Thio Sulphate(Anhydrous) of 46.5 grams and the positive bromine third of 45 grams is put in high speed shear emulsion reaction device
Alkane, rotational speed regulation is 9000r/min, is heated to reflux, after reacting 1.5 hours, filter n-pro-pyl sulfur for sulfur
Acid sodium filtrate.
Add 89.5 grams of vitamin Bs in a kettle.1, it is passed through distilled water stirring and dissolving, logical at 15～20 DEG C
Entering sodium hydroxide solution, reach 11～12 to pH value, continuation insulated and stirred, after 1.5 hours, passes through centrifuge
It is filtrated to get open loop solution.
Being injected in reactor by open loop solution, sodium n-propyl thiosulfate filtrate is slowly added dropwise to reactor,
Stirring is to separating out solids.After machine filters by centrifugation, add excessive hydrochloric acid dissolved solid thing, after again filtering,
Add ammonium carbonate saturated solution no longer to produce to precipitation.Then sucking filtration, be dried, obtain prosultiamine crude product 68.2
Gram.With obtaining 62.6 grams of prosultiamine fine work after dehydrated alcohol recrystallization.
Embodiment two
The Sodium Thio Sulphate(Anhydrous) of 46.5 grams and the positive bromine third of 45 grams is put in high speed shear emulsion reaction device
Alkane, rotational speed regulation is 9000r/min, is heated to reflux, and after reacting 2 hours, filters to obtain n-pro-pyl thiosulfuric acid
Sodium filtrate.
Add 89.5 grams of vitamin Bs in a kettle.1, it is passed through distilled water stirring and dissolving, logical at 15～20 DEG C
Entering sodium hydroxide solution, reach 11～12 to pH value, continuation insulated and stirred, after 1.5 hours, passes through centrifuge
It is filtrated to get open loop solution.
Being injected in reactor by open loop solution, sodium n-propyl thiosulfate filtrate is slowly added dropwise to reactor,
Stirring is to separating out solids.After machine filters by centrifugation, add excessive hydrochloric acid dissolved solid thing, after again filtering,
Add ammonium carbonate saturated solution no longer to produce to precipitation.Then sucking filtration, be dried, obtain prosultiamine crude product 71.5
Gram.With obtaining 65.4 grams of prosultiamine fine work after dehydrated alcohol recrystallization.
Embodiment three
The Sodium Thio Sulphate(Anhydrous) of 46.5 grams and the positive bromine third of 45 grams is put in high speed shear emulsion reaction device
Alkane, rotational speed regulation is 9000r/min, is heated to reflux, after reacting 2.5 hours, filter n-pro-pyl sulfur for sulfur
Acid sodium filtrate.
Add 89.5 grams of vitamin Bs in a kettle.1, it is passed through distilled water stirring and dissolving, logical at 15～20 DEG C
Entering sodium hydroxide solution, reach 11～12 to pH value, continuation insulated and stirred, after 1.5 hours, passes through centrifuge
It is filtrated to get open loop solution.
Being injected in reactor by open loop solution, sodium n-propyl thiosulfate filtrate is slowly added dropwise to reactor,
Stirring is to separating out solids.After machine filters by centrifugation, add excessive hydrochloric acid dissolved solid thing, after again filtering,
Add ammonium carbonate saturated solution no longer to produce to precipitation.Then sucking filtration, be dried, obtain prosultiamine crude product 70.2
Gram.With obtaining 64.3 grams of prosultiamine fine work after dehydrated alcohol recrystallization.
It should be noted that above example only in order to technical scheme to be described and unrestricted, although ginseng
According to preferred embodiment, the present invention is described in detail, it will be understood by those within the art that, can
Technical scheme is modified or equivalent, without deviating from the essence of technical solution of the present invention
God and scope, it all should be contained in the middle of scope of the presently claimed invention.
Claims (6)
1. the preparation method of a prosultiamine, it is characterised in that: include following steps,
Step one, Sodium Thio Sulphate(Anhydrous) and n-Propyl Bromide are put in high speed shear emulsion reaction device, adjust
The rotating speed of joint high speed shear emulsion reaction device is 8000～10000r/min, then heats, and carries out backflow anti-
Should, filter to obtain sodium n-propyl thiosulfate filtrate；
Step 2, add vitamin B in a kettle.1, add pure water stirring and dissolving, and be maintained at 15～
It is passed through sodium hydroxide solution at a temperature of 20 DEG C, reaches 11～12 to pH value, continue insulated and stirred 1.5 hours
After, it is filtrated to get open loop solution by centrifuge；
Step 3, the open loop solution obtained in step 2 is passed through in reactor, then will step one obtain
Solution is slowly added dropwise to reactor, and stirring is to separating out solids；
After step 4, by centrifugation machine filter, the hydrochloric acid adding excess makes solids fully dissolve, mistake again
After filter, filtrate add ammonium carbonate saturated solution to precipitation no longer produce, after sucking filtration, by filtration cakes torrefaction,
To prosultiamine crude product；
Step 5, by prosultiamine crude product dehydrated alcohol recrystallization 2 times, obtain prosultiamine essence after drying
Product.
The preparation method of prosultiamine the most according to claim 1, it is characterised in that: described backflow is anti-
It is 2 hours between Ying Shi.
The preparation method of prosultiamine the most according to claim 1, it is characterised in that: described high speed is cut
The rotating speed cutting emulsion reaction device is 9000r/min.
The preparation method of prosultiamine the most according to claim 1, it is characterised in that: described pure water
For distilled water.
The preparation method of prosultiamine the most according to claim 1, it is characterised in that: described anhydrous sulfur
Sodium thiosulfate and vitamin B1Mass ratio be 1:2～1:2.5.
The preparation method of prosultiamine the most according to claim 1, it is characterised in that: described anhydrous sulfur
Sodium thiosulfate is 1:1～1.5:1 with the mass ratio of n-Propyl Bromide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510105651.1A CN106032360A (en) | 2015-03-10 | 2015-03-10 | Preparation method of thiamine propyl disulfide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510105651.1A CN106032360A (en) | 2015-03-10 | 2015-03-10 | Preparation method of thiamine propyl disulfide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106032360A true CN106032360A (en) | 2016-10-19 |
Family
ID=57150394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510105651.1A Pending CN106032360A (en) | 2015-03-10 | 2015-03-10 | Preparation method of thiamine propyl disulfide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106032360A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308075A (en) * | 2001-01-09 | 2001-08-15 | 北京工商大学 | Preparation of propyl-2-methyl-3-furan dithioether |
| RU2175317C1 (en) * | 2000-12-01 | 2001-10-27 | Соболев Дмитрий Владимирович | Poly-(para-dihydroxy-para-phenylene)-thiosulfoacid sodium salt eliciting superoxidase activity and method of its synthesis |
| CN102304076A (en) * | 2011-07-05 | 2012-01-04 | 江苏兄弟维生素有限公司 | Preparation method of sodium n-propyl thiosulfate |
| CN104119259A (en) * | 2014-07-11 | 2014-10-29 | 江苏兄弟维生素有限公司 | A synthetic process of sodium n-propyl thiosulfate |
-
2015
- 2015-03-10 CN CN201510105651.1A patent/CN106032360A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2175317C1 (en) * | 2000-12-01 | 2001-10-27 | Соболев Дмитрий Владимирович | Poly-(para-dihydroxy-para-phenylene)-thiosulfoacid sodium salt eliciting superoxidase activity and method of its synthesis |
| CN1308075A (en) * | 2001-01-09 | 2001-08-15 | 北京工商大学 | Preparation of propyl-2-methyl-3-furan dithioether |
| CN102304076A (en) * | 2011-07-05 | 2012-01-04 | 江苏兄弟维生素有限公司 | Preparation method of sodium n-propyl thiosulfate |
| CN104119259A (en) * | 2014-07-11 | 2014-10-29 | 江苏兄弟维生素有限公司 | A synthetic process of sodium n-propyl thiosulfate |
Non-Patent Citations (1)
| Title |
|---|
| 韩光等: "丙硫硫胺的合成", 《中国药学杂志》 * |
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| C06 | Publication | ||
| PB01 | Publication | ||
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| CB02 | Change of applicant information | ||
| CB02 | Change of applicant information |
Address after: 224100 Southern District of Yancheng City Dafeng Marine Economic Development Zone, Jiangsu Applicant after: Jiangsu Brother Vitamins Co., Ltd. Address before: 224145 Jiangsu province Yancheng City Jiangsu province Dafeng Marine Economic Development Zone Southern District Applicant before: Jiangsu Brother Vitamins Co., Ltd. |
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Application publication date: 20161019 |