CN102002000A - Method for producing 5,5-dimethyl hydantoin - Google Patents
Method for producing 5,5-dimethyl hydantoin Download PDFInfo
- Publication number
- CN102002000A CN102002000A CN 201010548808 CN201010548808A CN102002000A CN 102002000 A CN102002000 A CN 102002000A CN 201010548808 CN201010548808 CN 201010548808 CN 201010548808 A CN201010548808 A CN 201010548808A CN 102002000 A CN102002000 A CN 102002000A
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- parts
- dimethyl hydantion
- heated
- stir
- minutes
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 title abstract 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000003756 stirring Methods 0.000 claims abstract description 24
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims abstract description 11
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 239000000047 product Substances 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 21
- 239000012043 crude product Substances 0.000 claims description 14
- 239000012452 mother liquor Substances 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000001939 inductive effect Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003337 fertilizer Substances 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract 3
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 abstract 3
- 239000001099 ammonium carbonate Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 238000007789 sealing Methods 0.000 abstract 1
- 230000001954 sterilising effect Effects 0.000 description 5
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000009182 swimming Effects 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- -1 halogen glycolylurea series Chemical class 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for producing 5,5-dimethyl hydantoin which is prepared from the following substances in parts by weight according to the steps as follows: adding water to ammonium bicarbonate and acetone cyanohydrin, stirring until the ammonium bicarbonate and the acetone cyanohydrin are fully dissolved, and sealing up while heating up to 10 DEG C; introducing ammonia to the mixture, heating slowly to 50-65 DEG C, stirring, heating up to 75-85 DEG C after keeping temperature constant for 1-2 hours, introducing air for 30-50 minutes, and filtering after cooling to a room temperature, thus obtaining crude dimethyl hydantoin and a mother liquid; and putting the crude dimethyl hydantoin into the mixture of water and the mother liquid while stirring, adding active carbon after heating up to 80-98 DEG C, decolouring, removing the active carbon by filtration, recooling, crystallizing, filtering centrifugally, and drying, thus obtaining the finished product of dimethyl hydantoin. The method has the advantages of simple technological reaction, low reaction temperature, short reaction time, less side reaction and high yield reaching 85%, and is easy to control; the raw material of ammonium bicarbonate applicable to the method belongs to chemical fertilizers, and is easy to obtain; and the filtrate produced by the technology can be used repeatedly, and no three wastes are discharged.
Description
Technical field
The present invention relates to a kind of 5, the production method of 5-dimethyl hydantion.
Background technology
5, the 5-dimethyl hydantion has another name called 5,5-T10 (to call DMH in the following text).
DMH is a kind of important organic synthesis intermediate of having many uses, and is the heterogeneous ring compound with certain rigid backbone.Can prepare a series of valuable derivatives by substitution reaction.As: C5H6Br2N2O2, two chlordantoins etc. is widely used in production fields such as organic synthesis, medicine, plastics, food, makeup, agricultural chemicals.
DMH abroad twentieth century seventies suitability for industrialized production just, the production equipment of producing thousands of tons of per year is all had in the U.S., Britain and Switzerland.Also there is production in Japan, but scale has only 600 tons of annual outputs.
China just begins to carry out the research of this respect the beginning of the nineties, and has realized suitability for industrialized production, is mainly used in the production of DMH derivative sterilizing agent.Research unit is by Hubei University, Institutes Of Technology Of Taiyuan, Shenyang Chemical Engineering Inst etc.There is Quzhou County, Hebei province synthetic glass factory (produce 100 tons of devices per year, built up in 1989) in factory, Hengshui Prefecture, Hebei province chemical industry pilot plant (producing 2000 tons of devices, nineteen ninety-fives per year builds up).In recent years, flourish along with the fine chemistry industry industry, acetone cyanohydrin output increase progressively increase in demand with DMH, built up a collection of production DMH factory at home, its synthesis technique generally adopts the cyclisation method, mainly contains interrupter method and continuous processing two lines.As in the patent No. being 200610038040.0 open source literature, a kind of preparation 5 is also disclosed, the production method of 5-dimethyl hydantion but yield be low, be not easy to control.
Summary of the invention
The present invention is intended to overcome the deficiencies in the prior art, developed a kind of 5, the production method of 5-dimethyl hydantion.
Of the present invention 5, the production method of 5-dimethyl hydantion is made by weight as follows by following material:
A, 500～700 parts in 600～800 parts in bicarbonate of ammonia, acetone cyanohydrin is added water stir fully dissolving, airtight when being heated to 10 ℃;
B, in the material that makes through a step, feed 30～50 parts of ammonias again, slowly heat to 50～65 ℃, constant temperature 1～2 hour, and stir;
C, will be heated to 75～85 ℃ through the material of b step system, air inducing 30～50 minutes is cooled to the room temperature after-filtration again, promptly makes dimethyl hydantion crude product and mother liquor;
D, will render in the mother liquor mixture of 150～300 parts water and 700～900 parts through 950～1150 parts of dimethyl hydantion crude products that the c step makes, stir while throwing in, add 3～8 parts of activated carbon after being heated to 80～98 ℃, decoloured 20～40 minutes, remove by filter activated carbon, crystallisation by cooling, centrifuging, oven dry more promptly makes the dimethyl hydantion finished product.
The market of DMH can be considered from purposes two aspects of water quality stabilizer and DMH derivative.China is the very not abundant country of a water resources, and in process water, the consumption of water coolant ranks first.Generally account for more than 60%.Therefore, recycling of water coolant is one of important channel of water saving.At this moment need add various medicaments such as inhibiter in the recirculated water.DMH can be directly used in the anti-stick mud agent of cooling water system.In addition, the multiple derivative of DMH can be done the sterilant of recirculated cooling water.
From the purposes aspect of DMH derivative, be mainly used in the engineering of water treatment sterilization, algae removal, deodorization and swimming sterilizing sterilization etc.Increasing rapidly at halogen glycolylurea series product consumption aspect U.S.'s swimming sterilizing sterilization.In addition, according to the demand of water treatment and entertainment industry, U.S. Zuo Long company produces in several reagent combinations of killing acquired immune deficiency syndrome (AIDS), also contains the halogenated hydantoin derivative.
Of the present invention 5, the production method technological reaction of 5-dimethyl hydantion is simple, temperature of reaction is low, the time is short, be easy to control, and side reaction is few, and yield can reach 85%; The raw material bicarbonate of ammonia that this method was suitable for belongs to fertilizer type, raw material is easy to get; The filtrate that is produced in this technology can recycle, and does not have the discharging of " three wastes ".
Embodiment
Embodiment 1
Of the present invention 5, the production method of 5-dimethyl hydantion is by following material, makes as follows by weight:
A, 500～700 parts in 600～800 parts in bicarbonate of ammonia, acetone cyanohydrin is added water stir fully dissolving, airtight when being heated to 10 ℃;
B, in the material that makes through a step, feed 30～50 parts of ammonias again, slowly heat to 50～65 ℃, constant temperature 1～2 hour, and stir;
C, will be heated to 75～85 ℃ through the material of b step system, air inducing 30～50 minutes is cooled to the room temperature after-filtration again, promptly makes dimethyl hydantion crude product and mother liquor;
D, will render in 150～300 parts of water and 700～900 parts of mother liquor mixtures through 950～1150 parts of dimethyl hydantion crude products that the c step makes, stir while throwing in, add 3～8 parts of activated carbon after being heated to 80～98 ℃, decoloured 20～40 minutes, remove by filter activated carbon, crystallisation by cooling, centrifuging, oven dry more promptly makes the dimethyl hydantion finished product.
Embodiment 2
Of the present invention 5, the production method of 5-dimethyl hydantion is by following material, makes as follows by weight:
A, 600 parts in 700 parts in bicarbonate of ammonia, acetone cyanohydrin is added water stir fully dissolving, airtight when being heated to 10 ℃;
B, in the material that makes through a step, feed 40 parts of ammonias again, slowly heat to 60 ℃, constant temperature 2 hours, and stir;
C, will be heated to 80 ℃ through the material of b step system, air inducing 40 minutes is cooled to the room temperature after-filtration again, promptly makes dimethyl hydantion crude product and mother liquor;
D, will render in the mixture of 800 parts in 200 parts in water and mother liquor through 1050 parts of dimethyl hydantion crude products that the c step makes, stir while throwing in, add 5 parts of activated carbon after being heated to 95 ℃, decoloured 30 minutes, remove by filter activated carbon, crystallisation by cooling, centrifuging, oven dry more promptly makes the dimethyl hydantion finished product.
Embodiment 3
Of the present invention 5, the production method of 5-dimethyl hydantion is by following material, makes as follows by weight:
A, 500 parts in 600 parts in bicarbonate of ammonia, acetone cyanohydrin is added water stir fully dissolving, airtight when being heated to 10 ℃;
B, in the material that makes through a step, feed 30 parts of ammonias again, slowly heat to 50 ℃, constant temperature 1.5 hours, and stir;
C, will be heated to 75 ℃ through the material of b step system, air inducing 30 minutes is cooled to the room temperature after-filtration again, promptly makes dimethyl hydantion crude product and mother liquor;
D, will render in the mixture of 700 parts in 150 parts in water and mother liquor through 950 parts of dimethyl hydantion crude products that the c step makes, stir while throwing in, add 3 parts of activated carbon after being heated to 90 ℃, decoloured 20 minutes, remove by filter activated carbon, crystallisation by cooling, centrifuging, oven dry more promptly makes the dimethyl hydantion finished product.
Embodiment 4
Of the present invention 5, the production method of 5-dimethyl hydantion is by following material, makes as follows by weight:
A, 700 parts in 800 parts in bicarbonate of ammonia, acetone cyanohydrin is added water stir fully dissolving, airtight when being heated to 10 ℃;
B, in the material that makes through a step, feed 50 parts of ammonias again, slowly heat to 65 ℃, constant temperature 2 hours, and stir;
C, will be heated to 85 ℃ through the material of b step system, air inducing 50 minutes is cooled to the room temperature after-filtration again, promptly makes dimethyl hydantion crude product and mother liquor;
D, will render in the mixture of 300 parts of water and 900 parts of mother liquors through 1150 parts of dimethyl hydantion crude products that the c step makes, stir while throwing in, add 8 parts of activated carbon after being heated to 95 ℃, decoloured 40 minutes, remove by filter activated carbon, crystallisation by cooling, centrifuging, oven dry more promptly makes the dimethyl hydantion finished product.
Claims (2)
1.5 the production method of 5-dimethyl hydantion is by following material, makes as follows by weight:
A, 500～700 parts in 600～800 parts in bicarbonate of ammonia, acetone cyanohydrin is added water stir fully dissolving, airtight when being heated to 10 ℃;
B, in the material that makes through a step, feed 30～50 parts of ammonias again, slowly heat to 50～65 ℃, constant temperature 1～2 hour, and stir;
C, will be heated to 75～85 ℃ through the material of b step system, air inducing 30～50 minutes is cooled to the room temperature after-filtration again, promptly makes dimethyl hydantion crude product and mother liquor;
D, will render in the mixture of 150～300 parts of water and 700～900 parts of mother liquors through 950～1150 parts of dimethyl hydantion crude products that the c step makes, stir while throwing in, add 3～8 parts of activated carbon after being heated to 80～98 ℃, decoloured 20～40 minutes, remove by filter activated carbon, crystallisation by cooling, centrifuging, oven dry more promptly makes the dimethyl hydantion finished product.
2. as claimed in claim 15, the production method of 5-dimethyl hydantion is by following material, makes as follows by weight:
A, 600 parts in 700 parts in bicarbonate of ammonia, acetone cyanohydrin is added water stir fully dissolving, airtight when being heated to 10 ℃;
B, in the material that makes through a step, feed 40 parts of ammonias again, slowly heat to 60 ℃, constant temperature 2 hours, and stir;
C, will be heated to 80 ℃ through the material of b step system, air inducing 40 minutes is cooled to the room temperature after-filtration again, promptly makes dimethyl hydantion crude product and mother liquor;
D, will render in the mixture of 200 parts of water and 800 parts of mother liquors through 1050 parts of dimethyl hydantion crude products that the c step makes, stir while throwing in, add 5 parts of activated carbon after being heated to 95 ℃, decoloured 30 minutes, remove by filter activated carbon, crystallisation by cooling, centrifuging, oven dry more promptly makes the dimethyl hydantion finished product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105488085A CN102002000B (en) | 2010-11-18 | 2010-11-18 | Method for producing 5,5-dimethyl hydantoin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105488085A CN102002000B (en) | 2010-11-18 | 2010-11-18 | Method for producing 5,5-dimethyl hydantoin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102002000A true CN102002000A (en) | 2011-04-06 |
| CN102002000B CN102002000B (en) | 2012-07-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010105488085A Expired - Fee Related CN102002000B (en) | 2010-11-18 | 2010-11-18 | Method for producing 5,5-dimethyl hydantoin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102002000B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104557721A (en) * | 2014-12-30 | 2015-04-29 | 沈阳化工研究院有限公司 | Method for producing 5,5-dimethylhydantoin |
| CN108148000A (en) * | 2018-03-20 | 2018-06-12 | 河北鑫淘源环保科技有限公司 | A kind of preparation method of 5,5 Dimethyl Hydan |
| CN115703743A (en) * | 2021-11-16 | 2023-02-17 | 吉林市吉化江城油脂化工有限责任公司 | Crystallization method of 5, 5-dimethylhydantoin |
| CN115703744A (en) * | 2021-11-16 | 2023-02-17 | 吉林市吉化江城油脂化工有限责任公司 | Preparation method of 5,5-dimethylhydantoin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1356321A (en) * | 2001-12-06 | 2002-07-03 | 天津大学 | Process for preparing 5,5-dimethyl-2,4-imidazolinedione by intermittent presurizing method |
| CN1803775A (en) * | 2006-01-23 | 2006-07-19 | 周新基 | Method for preparing 5,5-dimethylhydantion |
-
2010
- 2010-11-18 CN CN2010105488085A patent/CN102002000B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1356321A (en) * | 2001-12-06 | 2002-07-03 | 天津大学 | Process for preparing 5,5-dimethyl-2,4-imidazolinedione by intermittent presurizing method |
| CN1803775A (en) * | 2006-01-23 | 2006-07-19 | 周新基 | Method for preparing 5,5-dimethylhydantion |
Non-Patent Citations (2)
| Title |
|---|
| 《南京化工学院学报》 19950430 崔群等 改进Bucherer-Berg"s法合成乙内酰脲 125-129 1-2 第17卷, 第2期 2 * |
| 《山东化工》 20001231 王笑海 等 DMH的合成及应用 19-21,15 1-2 第29卷, 第4期 2 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104557721A (en) * | 2014-12-30 | 2015-04-29 | 沈阳化工研究院有限公司 | Method for producing 5,5-dimethylhydantoin |
| CN108148000A (en) * | 2018-03-20 | 2018-06-12 | 河北鑫淘源环保科技有限公司 | A kind of preparation method of 5,5 Dimethyl Hydan |
| CN115703743A (en) * | 2021-11-16 | 2023-02-17 | 吉林市吉化江城油脂化工有限责任公司 | Crystallization method of 5, 5-dimethylhydantoin |
| CN115703744A (en) * | 2021-11-16 | 2023-02-17 | 吉林市吉化江城油脂化工有限责任公司 | Preparation method of 5,5-dimethylhydantoin |
| CN115703743B (en) * | 2021-11-16 | 2024-05-10 | 吉林市吉化江城油脂化工有限责任公司 | Crystallization method of 5, 5-dimethyl hydantoin |
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| Publication number | Publication date |
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| CN102002000B (en) | 2012-07-25 |
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