CN110256335A - A kind of vitamin B6Synthesis technology - Google Patents
A kind of vitamin B6Synthesis technology Download PDFInfo
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- CN110256335A CN110256335A CN201910407552.7A CN201910407552A CN110256335A CN 110256335 A CN110256335 A CN 110256335A CN 201910407552 A CN201910407552 A CN 201910407552A CN 110256335 A CN110256335 A CN 110256335A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/04—Seven-membered rings not condensed with other rings
- C07D321/06—1,3-Dioxepines; Hydrogenated 1,3-dioxepines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a kind of vitamin Bs6Synthesis technology, comprising the following steps: cis-2-butene-Isosorbide-5-Nitrae glycol, hexamethylene and sodium form cation exchange resin are added in reactor, hexamethylene reflux is warming up to, toward n-butanal is added dropwise in reactor, to the end of dividing water, filtering removes resin；Buck is added, adjusts pH to 8.0-9.0 stratification, separates buck layer, distillation organic layer recycling hexamethylene simultaneously obtains seven ring of n-propyl dioxy and 4- methyl 5- ethyoxyl oxazole；It is added in reactor, reacts to obtain addition product with seven ring of n-propyl dioxy, then vitamin B is made through aromatisation and hydrolysis6.The present invention has changed the feeding mode of n-butanal, reduces the generation of side reaction, improves the yield of product.Being not required to rectifying purifying directly can obtain addition product with the generation Diels-Alder addition of 4- methyl -5- ethyoxyl oxazole, simplify technique, shorten process cycle, energy conservation and environmental protection reduces production cost.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of vitamin B6Synthesis technology.
Background technique
Vitamin B6The necessary material of body fat and glycometabolism, mainly act on the blood of human body, muscle, nerve,
Skin etc., participate in the synthesis of antibody, in digestive system gastric acid manufacture, maintain sodium-potassium balance etc..Synthesize vitamin B6Mainly have
Pyridone method, alkynyl ether, microbial method and oxazole method.The many and diverse yield of pyridone method step is lower, the reaction condition of alkynyl ether method
Harshness, microbial method is due to production restriction industrialized production.Therefore, oxazole method is generallyd use, industrially with 4- methyl 5- ethoxy
Base oxazole and seven ring of n-propyl dioxy are raw material, synthesize vitamin B through Diels-Alder addition, aromatisation, hydrolysis6。
Seven ring of n-propyl dioxy (2-propyl-4,7-dihydro-1,3-dioxepine), chemical name: 2- n-propyl-
4,7- dihydro -1,3- dioxy, seven ring, by the pure and mild n-butanal of cis-2-butene-Isosorbide-5-Nitrae-two, dehydrating condensation is made in acid condition.Mesh
Before, it produces in seven ring technique of n-propyl dioxy, is fed intake by the way of " treating different things alike ", through air-distillation and continuously after reflux water-dividing
Rectification under vacuum obtains.In this process, intramolecular and intermolecular easily occurs in acid condition for cis-2-butene-Isosorbide-5-Nitrae-glycol
Dehydration generates ether, and Aldol condensation easily occurs under acid catalysis and generates hydroxy aldehyde for n-butanal.It is mentioned in high temperature continuous still
Pure seven ring of propyl dioxy energy consumption height and long processing period.The by-product that the technique production cost is higher, feed stock conversion is low, generates
Object is more, and the discharge of waste water can cause environmental pollution.
Therefore, how the problem of a kind of economical and efficient and easy synthesis technology are as urgent need to resolve is provided.
Summary of the invention
Present invention aims at for defect present in above-mentioned prior art, a kind of vitamin B is provided6Synthesis work
Skill, the mild reaction condition, easy to operate, environmentally protective, obtained finished product purity and yield is all higher, is suitable for industry
Change application, has high economic benefit.
To achieve the above object, The technical solution adopted by the invention is as follows:
A kind of vitamin B6Synthesis technology, comprising the following steps:
1) cis-2-butene-Isosorbide-5-Nitrae-glycol, hexamethylene and sodium form cation exchange resin are added in reactor, are warming up to
N-butanal is added dropwise in hexamethylene reflux in reactor, and reflux water-dividing, to the end of dividing water, filtering removes sodium form cation exchange tree
Rouge；
2) buck is added into reaction solution, adjusts pH to 8.0-9.0, stratification separates buck layer, distillation organic layer recycling
Hexamethylene simultaneously obtains seven ring of n-propyl dioxy；
3) 4- methyl -5- ethyoxyl oxazole is added in reactor, reacts and is added with resulting seven ring of n-propyl dioxy
Vitamin B is made at object, then through aromatisation and hydrolysis6。
According to the above scheme, the molar ratio of cis-2-butene-Isosorbide-5-Nitrae-glycol and n-butanal described in step 1 is 1:(1.1-
1.3)；, the mass ratio of the cis-2-butene-Isosorbide-5-Nitrae-glycol and hexamethylene, sodium form cation exchange resin is 1:(1.0-1.2):
(0.1-0.2)。
According to the above scheme, the sodium form cation exchange resin is using preceding needing to pre-process, in 10.0wt% sodium chloride solution
Middle immersion 4h impregnates 4h in the hydrochloric acid solution of 2mol/L, is rinsed with water after filtering after filtering, until water outlet pH is 5.0 or so to be
Only.
According to the above scheme, sodium form cation exchange resin as catalyst is used in step 1；By cis-2-butene -1,4- two
Alcohol, hexamethylene, the mixing of sodium form cation exchange resin, are warming up to 75-80 DEG C, n-butanal are slowly added dropwise, use point when being added dropwise
Hydrophone reflux water-dividing is taken out of until anhydrous, and reaction was completed, filters out sodium form cation exchange resin.
According to the above scheme, the alkali in buck described in step 2 is sodium bicarbonate, in saleratus, sodium carbonate, potassium carbonate
It is one or more.
According to the above scheme, buck described in the water and step 2 separated in step 1 recycles, when the pH of buck is lower than 8.0
When, supplement solute；Step 1 filtering removal sodium form cation exchange resin recycles.
According to the above scheme, organic layer described in step 2 distills under normal pressure, recycles hexamethylene and unreacted feedstock circulation
It uses.
According to the above scheme, the mass ratio of seven ring of n-propyl dioxy described in step 3 and the 4- methyl -5- ethyoxyl oxazole
For (8.5-10.0): 1.
The effect that buck is added in the present invention is to neutralize excessive acid, oxazole easy open loop in acid condition.
Synthetic route of the present invention is as follows:
Compared with prior art, the beneficial effects of the present invention are:
The present invention has changed the feeding mode of n-butanal, reduces the generation of side reaction, improves the yield of product.Sodium form
Cation exchange resin can recycle after regeneration, and can recycle after water and buck the supplement solute that water segregator separates makes
With the hexamethylene distilled can be with cycle applications.Process stream high recycling rate after optimization will not generate waste water, to ring
Border is friendly.Seven ring yield of gained n-propyl dioxy and purity are higher after solvent distillation, be not required to rectifying purifying can directly with 4- first
Base -5- ethyoxyl oxazole occurs Diels-Alder addition and obtains addition product, then vitamin is made through aromatisation and hydrolysis
B6, technique is simplified, process cycle is shortened, is more energy-saving and environmentally friendly, production cost is reduced.
Detailed description of the invention
Fig. 1: synthesis process flow diagram of the present invention.
Specific embodiment
Following embodiment further illustrates technical solution of the present invention, but not as limiting the scope of the invention.
Embodiment 1
A kind of vitamin B6Synthesis technology, process route referring to Fig.1 shown in, the specific steps are as follows:
In tri- mouthfuls of reaction flasks of 500mL equipped with blender and thermometer, 50.0g (567.4mmol) cis- 2- fourth is added
Alkene-Isosorbide-5-Nitrae-glycol, 50.0g hexamethylene and the pretreated sodium form cation exchange resin of 5.6g, reaction system are warming up to 75-80
N-butanal DEG C is slowly added dropwise, controls temperature at 75-80 DEG C, use water segregator reflux water-dividing when being added dropwise, taken out of until anhydrous, knot
Shu Fanying filters out sodium form cation exchange resin.Saturated sodium bicarbonate solution is added into reaction flask to pH 8.0 or so,
Stratification.After separating water layer, it is warming up to 110 DEG C of air-distillation organic layers recycling hexamethylenes and the complete n-butanal of unreacted, drop
Temperature is to 80-85 DEG C of vacuum distillation 20min.Slightly yellowish seven ring 74.5g of residue n-propyl dioxy, yield are obtained after distillation
=(74.5g/ (567.4mmol × 0.001 × 142.19)) × 100%=92.4%, through gas chromatographic analysis, by area normalization
Method meter content is 95.9%.Be added 7.5g (59.0mmol) 4- methyl -5- ethyoxyl oxazole be warming up to 150 DEG C and keep the temperature 15h into
Row Diels-Alder reaction cools to 130 DEG C of vacuum distillations and recycles excessive seven ring of n-propyl dioxy, Zhi Daowu after having reacted
Distillate obtains addition product.The dissolution of 20mL ethyl alcohol is added, is cooled to 30 DEG C, is added 0.1% hydrochloric acid solution of 60mL, 25-30 DEG C
15h is kept the temperature, 60 DEG C of heat preservation 2h is warming up to and carries out aromatization.Be recovered under reduced pressure after having reacted Diluted Alcohol until material in the pasty state,
With 3mol/L hydrochloric acid solution tune pH to 1.0-1.5, it is warming up to 78-80 DEG C of hydrolysis 1h.Material is concentrated under reduced pressure to be evaporated substantially, residue
Continue decompression dehydration after adding 95% ethyl alcohol of 20mL to dissolve to doing, add 95% ethyl alcohol of 10mL, be cooled to 20 DEG C, filtering is washed
It washs, obtains 10.2g yellow-brown solid, yield=(10.2g/ (59.0mmol × 0.001 × 205.6)) × 100%=after dry
84.1%, through efficient liquid phase chromatographic analysis, by external standard method, content is 98.3% in terms of peak area.
Embodiment 2
A kind of vitamin B6Synthesis technology, process route referring to Fig.1 shown in, the specific steps are as follows:
In tri- mouthfuls of reaction flasks of 1000mL equipped with blender and thermometer, 100.0g (1134.9mmol) cis- 2- is added
Butene-1,4- glycol, 110.0g hexamethylene and the pretreated sodium form cation exchange resin of 9.4g, reaction system are warming up to
75-80 DEG C is slowly added dropwise n-butanal, controls temperature at 75-80 DEG C, uses water segregator reflux water-dividing when being added dropwise, until anhydrous band
Out, reaction was completed, filters out sodium form cation exchange resin.Saturated sodium bicarbonate solution is added into reaction flask to pH 8.0
Left and right, stratification.After separating water layer, it is warming up to 110 DEG C of air-distillation organic layers recycling hexamethylenes and the complete positive fourth of unreacted
Aldehyde.It is cooled to 80-85 DEG C of vacuum distillation 25min, obtains slightly yellowish seven ring 146.6g of residue n-propyl dioxy, yield
=(146.6g/ (1134.9mmol × 0.001 × 142.19)) × 100%=90.8% is returned through gas chromatographic analysis by area
One method meter content is 96.8%.14.7g (115.6mmol) 4- methyl -5- ethyoxyl oxazole is added to be warming up to 150 DEG C and keep the temperature
15h carries out Diels-Alder reaction, and 130 DEG C of vacuum distillations are cooled to after having reacted and recycle excessive seven ring of n-propyl dioxy, directly
To no distillate, addition product is obtained.The dissolution of 40mL ethyl alcohol is added, is cooled to 30 DEG C, 0.1% hydrochloric acid solution of 100mL, 25- is added
30 DEG C of heat preservation 15h are warming up to 60 DEG C of heat preservation 2h and carry out aromatization.Diluted Alcohol is recovered under reduced pressure after having reacted until material is in paste
Shape is warming up to 78-80 DEG C of hydrolysis 1h with 3mol/L hydrochloric acid solution tune pH to 1.0-1.5.Material is concentrated under reduced pressure to be evaporated substantially, it is residual
Excess continues decompression dehydration to doing after adding 95% ethyl alcohol of 20mL to dissolve, add 95% ethyl alcohol of 20mL, be cooled to 20 DEG C, mistake
Filter, washing obtain 19.8g yellow-brown solid after dry, and yield=(19.8g/ (115.6mmol × 0.001 × 205.6)) ×
100%=83.3%, through efficient liquid phase chromatographic analysis, by external standard method, content is 98.1% in terms of peak area.
Embodiment 3
A kind of vitamin B6Synthesis technology, process route referring to Fig.1 shown in, the specific steps are as follows:
In tri- mouthfuls of reaction flasks of 1000mL equipped with blender and thermometer, 150.0g (1702.4mmol) cis- 2- is added
Butene-1,4- glycol, 170.0g hexamethylene and the pretreated sodium form cation exchange resin of 19.5g, reaction system are warming up to
75-80 DEG C is slowly added dropwise n-butanal, controls temperature at 75-80 DEG C, uses water segregator reflux water-dividing when being added dropwise, until anhydrous band
Out, reaction was completed, filters out sodium form cation exchange resin.Saturated sodium bicarbonate solution is added into reaction flask to pH 8.0
Left and right, stratification.After separating water layer, it is warming up to 110 DEG C of air-distillation organic layers recycling hexamethylenes and the complete positive fourth of unreacted
Aldehyde.It is cooled to 80-85 DEG C of vacuum distillation 30min, obtains slightly yellowish seven ring 216.8g of residue n-propyl dioxy, yield
=(216.8g/ (1702.4mmol × 0.001 × 142.19)) × 100%=89.6% is returned through gas chromatographic analysis by area
One method meter content is 97.5%.21.6g (169.9mmol) 4- methyl -5- ethyoxyl oxazole is added to be warming up to 150 DEG C and keep the temperature
15h carries out Diels-Alder addition, and 130 DEG C of vacuum distillations are cooled to after having reacted and recycle excessive seven ring of n-propyl dioxy, directly
To no distillate, addition product is obtained.The dissolution of 60mL ethyl alcohol is added, is cooled to 30 DEG C, 0.1% hydrochloric acid solution of 150mL, 25- is added
30 DEG C of heat preservation 15h are warming up to 60 DEG C of heat preservation 2h and carry out aromatization.Diluted Alcohol is recovered under reduced pressure after having reacted until material is in paste
Shape is warming up to 78-80 DEG C of hydrolysis 1h with 3mol/L hydrochloric acid solution tune pH to 1.0-1.5.Material is concentrated under reduced pressure to be evaporated substantially, it is residual
Excess continues decompression dehydration to doing after adding 95% ethyl alcohol of 60mL to dissolve, add 95% ethyl alcohol of 30mL, be cooled to 20 DEG C, mistake
Filter, washing obtain 29.2g yellow-brown solid after dry, and yield=(29.2g/ (169.9mmol × 0.001 × 205.6)) ×
100%=83.6%, through efficient liquid phase chromatographic analysis, by external standard method, content is 98.0% in terms of peak area.
Claims (8)
1. a kind of vitamin B6Synthesis technology, it is characterised in that the following steps are included:
1) cis-2-butene-Isosorbide-5-Nitrae-glycol, hexamethylene and sodium form cation exchange resin are added in reactor, are warming up to hexamethylene
N-butanal is added dropwise in alkane reflux in reactor, and reflux water-dividing, to the end of dividing water, filtering removes sodium form cation exchange resin；
2) buck is added into reaction solution, adjusts pH to 8.0-9.0, stratification separates buck layer, and distillation organic layer recycles hexamethylene
Alkane simultaneously obtains seven ring of n-propyl dioxy；
3) 4- methyl -5- ethyoxyl oxazole is added in reactor, reacts to obtain addition product with seven ring of n-propyl dioxy, then through virtue
Vitamin B is made in structure and hydrolysis6。
2. vitamin B as described in claim 16Synthesis technology, it is characterised in that cis-2-butene-Isosorbide-5-Nitrae-two described in step 1
The molar ratio of alcohol and n-butanal is 1:(1.1-1.3)；, the cis-2-butene-Isosorbide-5-Nitrae-glycol and hexamethylene, sodium form cation are handed over
The mass ratio for changing resin is 1:(1.0-1.2): (0.1-0.2).
3. vitamin B as described in claim 16Synthesis technology, it is characterised in that before the sodium form cation exchange resin use
It needs to pre-process, 4h is impregnated in 10.0wt% sodium chloride solution, 4h is impregnated in the hydrochloric acid solution of 2mol/L after filtering, after filtering
It is rinsed with water, until water outlet pH is 5.0 or so.
4. vitamin B as described in claim 16Synthesis technology, it is characterised in that in step 1 use sodium form cation exchange tree
Rouge makees catalyst；Cis-2-butene-Isosorbide-5-Nitrae-glycol, hexamethylene, sodium form cation exchange resin are mixed, are warming up to 75-80 DEG C,
N-butanal is slowly added dropwise, uses water segregator reflux water-dividing when being added dropwise, is taken out of until anhydrous, reaction was completed, filters out sodium form sun
Ion exchange resin.
5. vitamin B as described in claim 16Synthesis technology, it is characterised in that alkali in buck described in step 2 is carbonic acid
One of hydrogen sodium, saleratus, sodium carbonate, potassium carbonate are a variety of.
6. vitamin B as described in claim 16Synthesis technology, it is characterised in that described in the water and step 2 separated in step 1
Buck recycles, and when the pH of buck is lower than 8.0, supplements solute；Step 1 filtering removal sodium form cation exchange resin circulation
It utilizes.
7. vitamin B as described in claim 16Synthesis technology, it is characterised in that organic layer described in step 2 steams under normal pressure
It evaporates, recycles hexamethylene and unreacted feedstock circulation uses.
8. vitamin B as described in claim 16Synthesis technology, it is characterised in that seven ring of n-propyl dioxy described in step 3 with
The mass ratio of the 4- methyl 5- ethyoxyl oxazole is (8.5-10.0): 1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112778196A (en) * | 2021-01-06 | 2021-05-11 | 安徽泰格维生素发展有限公司 | Preparation method of vitamin B6 |
| CN114349761A (en) * | 2021-12-21 | 2022-04-15 | 新发药业有限公司 | Vitamin B6 impurity A and preparation method and application thereof |
| CN114349692A (en) * | 2021-12-10 | 2022-04-15 | 江西天新药业股份有限公司 | Vitamin B6And refining method thereof |
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| CN103524479A (en) * | 2012-07-06 | 2014-01-22 | 江西天新药业有限公司 | Preparation method of 2-alkyl-4,7-dihydro-1,3-2-propyl-1,3-dioxocyclo-5-pentene |
| CN104710351A (en) * | 2013-12-13 | 2015-06-17 | 大丰海嘉诺药业有限公司 | Continuous preparation method of vitamin B6 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112778196A (en) * | 2021-01-06 | 2021-05-11 | 安徽泰格维生素发展有限公司 | Preparation method of vitamin B6 |
| CN114349692A (en) * | 2021-12-10 | 2022-04-15 | 江西天新药业股份有限公司 | Vitamin B6And refining method thereof |
| CN114349692B (en) * | 2021-12-10 | 2023-12-19 | 江西天新药业股份有限公司 | Vitamin B 6 And a method for refining the same |
| CN114349761A (en) * | 2021-12-21 | 2022-04-15 | 新发药业有限公司 | Vitamin B6 impurity A and preparation method and application thereof |
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