CN108558775A - A kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione - Google Patents
A kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione Download PDFInfo
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- CN108558775A CN108558775A CN201810577846.XA CN201810577846A CN108558775A CN 108558775 A CN108558775 A CN 108558775A CN 201810577846 A CN201810577846 A CN 201810577846A CN 108558775 A CN108558775 A CN 108558775A
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- Prior art keywords
- menadione
- dimethyl
- sulfurous acid
- preparation
- alcohol sulfurous
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- 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
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/174—Vitamins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/44—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing doubly-bound oxygen atoms bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
- C07C50/12—Naphthoquinones, i.e. C10H6O2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to Vitamin K3 processing preparation field more particularly to a kind of preparation methods of dimethyl pyrimidine alcohol sulfurous acid menadione.Including following effective procedure：A, Jiang Shui, menadione sodium bisulfite, 4,6 dimethyl, 2 hydroxy pyrimidine hydrochloride are added in reaction kettle, and between controlling 20 DEG C~40 DEG C of temperature, the time is between 1~2h；B, it and then is cooled between 10 DEG C~20 DEG C, filters, obtain filter cake；C, it will be dried after 5 10 DEG C of washings of filter cake, obtain the dimethyl pyrimidine alcohol sulfurous acid menadione finished product of white or off-white color.The present invention is using existing widely used menadione sodium bisulfite as raw material, by with 4, the reaction of 6 dimethyl, 2 hydroxy pyrimidine hydrochloride, dimethyl pyrimidine alcohol sulfurous acid menadione is made, and then solve the technical issues of existing shortage MPB systems, rational preparation method, meanwhile, preparation method provided by the present invention, simply, reliably, it is suitble to large-scale promotion to use.
Description
Technical field
The invention belongs to Vitamin K3 processing preparation field more particularly to a kind of dimethyl pyrimidine alcohol sulfurous acid menadiones
Preparation method.
Background technology
Vitamin K3 is 2- methyl-1s, 4 naphthalene elder brothers (abbreviation menadione) and its general designation for adding object.The function of Vitamin K3 is to promote
Into hemoglutination, the level of factor and the supply of Vitamin K3 are directly related in blood.Lack the animal of Vitamin K3,
Clotting time can significantly extend, there is a serious shortage of when, minor scratches will result in haemophilia and lead to death.Due to existing feeding
Hormone and antibiotic are often added in material, this results in the shortage of animal Vitamin K3, and therefore, it is necessary in feed, dimension is added
Raw element K3 is to supplement the content of Vitamin K3 in animal body.
Currently, the Vitamin K3 as feed addictive has sodium hydrogensulfite first naphthalenone (MSB), bisulfite niacinamide first
Naphthoquinones (MNB) and dimethyl pyrimidine alcohol sulfurous acid menadione (MPB).MSB stability is poor, the easy moisture absorption.MNB and MPB stability compared with
It is good, meanwhile, the synthesis report about MNB is more, but, preparation method about MPB is but rarely reported, and lacks system and rationally
Preparation method.
Invention content
The present invention lacks system, the technology of rational preparation method for above-mentioned dimethyl pyrimidine alcohol sulfurous acid menadione
Problem proposes a kind of reasonable design, the preparation method of the simple dimethyl pyrimidine alcohol sulfurous acid menadione of method.
In order to achieve the above object, the technical solution adopted by the present invention is that it is sub- that the present invention provides a kind of dimethyl pyrimidine alcohol
The preparation method of menadiol disulfate, including following effective procedure：
A, Jiang Shui, menadione sodium bisulfite, 4,6- dimethyl -2- hydroxy pyrimidine hydrochlorides are added in reaction kettle, control
Between 20 DEG C~40 DEG C of temperature processed, 1~2h of time, reaction is completed；
B, between feed liquid obtained by the reaction being cooled to 10 DEG C~20 DEG C, filtering obtains filter cake；
C, it will be dried after 5-10 DEG C of washing of filter cake, obtain the dimethyl pyrimidine alcohol sulfurous acid menadione of white or off-white color
Finished product.
As in the preferred a steps, the dosage of 4, the 6- dimethyl -2- hydroxy pyrimidine hydrochlorides is sodium hydrogensulfite
1~1.2 times of menadione mole.
As in the preferred a steps, the dosage of the water is 5~7 times of menadione sodium bisulfite weight.
Compared with prior art, the advantages and positive effects of the present invention are,
1, the present invention is made by providing a kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione using existing extensively
Diformazan is made by the reaction with 4,6- dimethyl -2- hydroxy pyrimidine hydrochlorides as raw material in the menadione sodium bisulfite used
Yl pyrimidines alcohol sulfurous acid menadione, and then solve the technical issues of existing shortage MPB systems, rational preparation method, meanwhile,
Preparation method provided by the present invention, it is simple, reliable, it is suitble to large-scale promotion to use.
Specific implementation mode
To better understand the objects, features and advantages of the present invention, with reference to embodiment to this hair
It is bright to be described further.It should be noted that in the absence of conflict, the feature in embodiments herein and embodiment can
To be combined with each other.
Many details are elaborated in the following description to facilitate a thorough understanding of the present invention, still, the present invention may be used also
With using implementing different from other modes described here, therefore, the present invention is not limited to the specific of specification is described below
The limitation of embodiment.
Embodiment 1, the present embodiment provides a kind of preparation methods of dimethyl pyrimidine alcohol sulfurous acid menadione
Required water, menadione sodium bisulfite, 4,6- dimethyl -2- hydroxy pyrimidine salt have been weighed first, in accordance with ratio
The dosage of hydrochlorate, 4,6- dimethyl -2- hydroxy pyrimidine hydrochlorides is consistent with menadione sodium bisulfite mole, and the dosage of water is
5 times of menadione sodium bisulfite weight, in above-mentioned raw materials, menadione sodium bisulfite be Vitamin K3 one kind, 4,6- bis-
Methyl -2- hydroxy pyrimidine hydrochlorides are a kind of material intermediates, mainly for the production of Nicarbazin, Nicarbazin be one efficiently,
Low toxicity, do not influence immune function, drug resistance worm pearl generates slow anticoccidial drug, 4,6- dimethyl -2- hydroxy pyrimidine hydrochlorides be system
One of the intermediate of standby Nicarbazin.
Raw material is existing matured product needed for above, therefore is not added with detailed description in the present embodiment.
Then, above-mentioned load weighted raw material is added in reaction kettle, controls 30 DEG C of temperature, the time is in 1.5h (by again
It is secondary to be added subject to a small amount of 4,6- dimethyl -2- hydroxy pyrimidine hydrochloride deposit-frees generation), obtain dimethyl pyrimidine alcohol sulfurous
Sour menadione solution；
Then, dimethyl pyrimidine alcohol sulfurous acid menadione solution obtained by the reaction is cooled to 15 DEG C or so (fluctuations up and down
± 1 DEG C), vacuum filtration is adopted, filter cake is obtained；
Finally, it will be dried after 10 DEG C of washings of filter cake, obtain the dimethyl pyrimidine alcohol sulfurous acid first naphthalene of white or off-white color
Quinone finished product.
Embodiment 2, the present embodiment provides a kind of preparation methods of dimethyl pyrimidine alcohol sulfurous acid menadione
Required water, menadione sodium bisulfite, 4,6- dimethyl -2- hydroxy pyrimidine salt have been weighed first, in accordance with ratio
The dosage of hydrochlorate, 4,6- dimethyl -2- hydroxy pyrimidine hydrochlorides is 1.1 times of menadione sodium bisulfite mole, the dosage of water
It is 6 times of menadione sodium bisulfite weight.
Then, above-mentioned load weighted raw material is added in reaction kettle, controls 20 DEG C of temperature, the time between 2h, obtains
Dimethyl pyrimidine alcohol sulfurous acid menadione solution；
Then, dimethyl pyrimidine alcohol sulfurous acid menadione solution obtained by the reaction is cooled to 20 DEG C of temperature to 15 DEG C or so
(± 1 DEG C of fluctuation up and down), adopts vacuum filtration, obtains filter cake；
Finally, it will be dried after 5 DEG C of washings of filter cake, obtain the dimethyl pyrimidine alcohol sulfurous acid menadione of white or off-white color
Finished product.
Embodiment 3, the present embodiment provides a kind of preparation methods of dimethyl pyrimidine alcohol sulfurous acid menadione
Required water, menadione sodium bisulfite, 4,6- dimethyl -2- hydroxy pyrimidine salt have been weighed first, in accordance with ratio
The dosage of hydrochlorate, 4,6- dimethyl -2- hydroxy pyrimidine hydrochlorides is 1.2 times of menadione sodium bisulfite mole, the dosage of water
It is 7 times of menadione sodium bisulfite weight.
Then, above-mentioned load weighted raw material is added in reaction kettle, controls temperature 50 C, the time between 2h, obtains
Dimethyl pyrimidine alcohol sulfurous acid menadione solution；
Then, dimethyl pyrimidine alcohol sulfurous acid menadione solution obtained by the reaction is cooled to 10 DEG C of temperature to 15 DEG C or so
(± 1 DEG C of fluctuation up and down), adopts vacuum filtration, obtains filter cake；
Finally, it will be dried after 8 DEG C of washings of filter cake, obtain the dimethyl pyrimidine alcohol sulfurous acid menadione of white or off-white color
Finished product.
Testing inspection：
1), test method：
According to national standards《Feed addictive dimethyl pyrimidine alcohol sulfurous acid menadione》It is detected.
2), testing result
Table 1：1~embodiment of embodiment, 3 testing result table
It to sum up detects, country is met using dimethyl pyrimidine alcohol sulfurous acid menadione made from method provided by the present invention
Standard, and method provided by the present invention is simple and reliable, and large-scale promotion is suitble to use.
The above described is only a preferred embodiment of the present invention, being not that the invention has other forms of limitations, appoint
What those skilled in the art changed or be modified as possibly also with the technology contents of the disclosure above equivalent variations etc.
It imitates embodiment and is applied to other fields, but it is every without departing from technical solution of the present invention content, according to the technical essence of the invention
To any simple modification, equivalent variations and remodeling made by above example, the protection domain of technical solution of the present invention is still fallen within.
Claims (3)
1. a kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione, which is characterized in that including following effective procedure：
A, Jiang Shui, menadione sodium bisulfite, 4,6- dimethyl -2- hydroxy pyrimidine hydrochlorides are added in reaction kettle, control temperature
Between 20 DEG C~40 DEG C of degree, the time is between 1~2h；
B, it and then is cooled between 10 DEG C~20 DEG C, filters, obtain filter cake；
C, will filter cake with 5-10 DEG C washing after dry, obtain white or off-white color dimethyl pyrimidine alcohol sulfurous acid menadione at
Product.
2. a kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione according to claim 1, which is characterized in that institute
State in a steps, the dosages of 4, the 6- dimethyl -2- hydroxy pyrimidine hydrochlorides be menadione sodium bisulfite mole 1~
1.2 again.
3. a kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione according to claim 2, which is characterized in that institute
It states in a steps, the dosage of the water is 5~7 times of menadione sodium bisulfite weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810577846.XA CN108558775A (en) | 2018-06-07 | 2018-06-07 | A kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810577846.XA CN108558775A (en) | 2018-06-07 | 2018-06-07 | A kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione |
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| CN108558775A true CN108558775A (en) | 2018-09-21 |
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| CN201810577846.XA Pending CN108558775A (en) | 2018-06-07 | 2018-06-07 | A kind of preparation method of dimethyl pyrimidine alcohol sulfurous acid menadione |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3328169A (en) * | 1962-11-09 | 1967-06-27 | Heterochemical Corp | Menadione bisulfite adducts of dicyanodiamidine-2, 4, 6-triamino-1, 3, 5-triazine and pyrimidines substituted at the two positions and feeds |
| DE2855851A1 (en) * | 1978-07-21 | 1980-01-31 | Stoppani Luigi Spa | ADDUCTS OF VITAMIN-K COMPOUNDS AND STABILIZING VITAMIN COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| CN105037125A (en) * | 2015-06-25 | 2015-11-11 | 泉州出入境检验检疫局综合技术服务中心 | Method for preparing vitamin K3 |
-
2018
- 2018-06-07 CN CN201810577846.XA patent/CN108558775A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3328169A (en) * | 1962-11-09 | 1967-06-27 | Heterochemical Corp | Menadione bisulfite adducts of dicyanodiamidine-2, 4, 6-triamino-1, 3, 5-triazine and pyrimidines substituted at the two positions and feeds |
| DE2855851A1 (en) * | 1978-07-21 | 1980-01-31 | Stoppani Luigi Spa | ADDUCTS OF VITAMIN-K COMPOUNDS AND STABILIZING VITAMIN COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| GB2025976B (en) * | 1978-07-21 | 1982-12-01 | Stoppani Luigi Spa | Adducts of k vitaminic compounds and stabilizing vitamins preparation thereof and stabilized adducts thus provided |
| CN105037125A (en) * | 2015-06-25 | 2015-11-11 | 泉州出入境检验检疫局综合技术服务中心 | Method for preparing vitamin K3 |
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Application publication date: 20180921 |