CN104447411B - The process for purification of n-butyl isocyanate - Google Patents
The process for purification of n-butyl isocyanate Download PDFInfo
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- CN104447411B CN104447411B CN201410692026.7A CN201410692026A CN104447411B CN 104447411 B CN104447411 B CN 104447411B CN 201410692026 A CN201410692026 A CN 201410692026A CN 104447411 B CN104447411 B CN 104447411B
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- butyl isocyanate
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- purification
- sodium hydroxide
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- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 title claims abstract description 99
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000000746 purification Methods 0.000 title claims abstract description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 78
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 20
- 239000012044 organic layer Substances 0.000 claims abstract description 13
- 239000012535 impurity Substances 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 55
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 24
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 21
- 230000006837 decompression Effects 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 239000012074 organic phase Substances 0.000 abstract description 2
- 238000013517 stratification Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 description 5
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Abstract
The present invention provides the process for purification of a kind of n-butyl isocyanate, comprises the following steps: provide n-butyl isocyanate solution to be refined；At 10 DEG C ~ 5 DEG C, n-butyl isocyanate solution to be refined toward described in while stirring adds aluminum chloride and dropping sodium hydroxide solution, reacts 0.5 ~ 1 hour, obtain mixed liquor；And described mixed liquor is stood, is layered, take upper organic layer and carry out separating-purifying, obtain n-butyl isocyanate.The process for purification of above-mentioned n-butyl isocyanate, utilize sodium hydroxide under the effect of aluminum chloride, neutralize the impurity acid in n-butyl isocyanate to be refined and poly-n-butyl isocyanate floccule, pass through stratification again, take upper organic phase and carry out separating-purifying, obtain n-butyl isocyanate, improve product quality.
Description
Technical field
The present invention relates to chemical field, particularly relate to the process for purification of a kind of n-butyl isocyanate.
Background technology
N-butyl isocyanate is a kind of important pesticide intermediate.With n-butyl isocyanate as catalyst when phosgenation prepares sulfonylurea herbicide, reacting balance can be made, improve yield；N-butyl isocyanate is additionally operable to the synthesis of agriculture chemicals fungicide benomyl.Benomyl is a kind of high-efficiency broad spectrum, systemic fungicide, has protection, roots out and therapeutical effect, can prevent and treat various crop disease.But there is the problems such as muddy, free acid is higher and is difficult to clean off in the n-butyl isocyanate that the synthetic method of traditional n-butyl isocyanate is produced, do not meet the i.e. auto polymerization of prescription, short term stored and form floccule, make subsequent reactions yield reduce, affect product quality.
Summary of the invention
Based on this, it is necessary to the n-butyl isocyanate produced for the synthetic method of traditional n-butyl isocyanate exist muddy, free acid is higher and the problem that is difficult to clean off, it is provided that the process for purification of a kind of n-butyl isocyanate.
The process for purification of a kind of n-butyl isocyanate, comprises the following steps:
N-butyl isocyanate solution to be refined is provided；
At-10 DEG C ~-5 DEG C, n-butyl isocyanate solution to be refined toward described in while stirring adds aluminum chloride and dropping sodium hydroxide solution, reacts 05 ~ 1 hour, obtain mixed liquor；And
Described mixed liquor is stood, is layered, take upper organic layer and carry out separating-purifying, obtain n-butyl isocyanate.
Wherein in an embodiment, the concentration of described sodium hydroxide solution is 0.2mol/L ~ 0.25mol/L.
Wherein in an embodiment, described in the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined be 1:0.05:5 ~ 6.
Wherein in an embodiment, described in the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined be 1:0.05:5.5.
Wherein in an embodiment, the time of described dropping sodium hydroxide solution is 0.5 ~ 1 hour.
In the step wherein in an embodiment, stood by described mixed liquor, being layered, the time of described standing is 30 ~ 60 minutes.
Wherein in an embodiment, described in take upper organic layer and carry out separating-purifying, obtain the step of n-butyl isocyanate particularly as follows: take upper organic layer to carry out decompression distillation, collect fraction, obtain n-butyl isocyanate.
Wherein in an embodiment, in the step of described decompression distillation, the vacuum≤-0.09MPa of decompression distillation.
Wherein in an embodiment, described in n-butyl isocyanate solution to be refined provided by following steps:
Dimethylbenzene and n-butylamine are mixed, drips hydrochloric acid, obtain the mixed solution containing n-butylamine hydrochlorate；
The described mixed solution containing n-butylamine hydrochlorate is heated, under reflux conditions azeotropic dehydration, until moisture takes off, obtain n-butylamine hydrochlorate dimethylbenzene material；
Described n-butylamine hydrochlorate dimethylbenzene material is carried out logical phosgene reaction, obtains the mixture containing n-butyl isocyanate；And
The described mixture containing n-butyl isocyanate is carried out rectification, obtain described in n-butyl isocyanate solution to be refined.
Wherein in an embodiment, described in n-butyl isocyanate solution to be refined, mass content >=99.0% of n-butyl isocyanate, mass content ＞ 0.5% of impurity free acid.
The process for purification of above-mentioned n-butyl isocyanate, utilize sodium hydroxide under the effect of aluminum chloride, neutralize the impurity acid in n-butyl isocyanate to be refined and poly-n-butyl isocyanate floccule, pass through stratification again, take upper organic phase and carry out separating-purifying, obtain n-butyl isocyanate, improve product quality.
Accompanying drawing explanation
Fig. 1 is the process for purification schematic flow sheet of the n-butyl isocyanate of an embodiment.
Detailed description of the invention
Understandable for enabling the above-mentioned purpose of the present invention, feature and advantage to become apparent from, below in conjunction with the accompanying drawings the detailed description of the invention of the present invention is described in detail.Elaborate a lot of detail in the following description so that fully understanding the present invention.But the present invention can implement to be much different from alternate manner described here, those skilled in the art can do similar improvement in the case of intension of the present invention, and therefore the present invention is not limited by following public being embodied as.
Refer to Fig. 1, be the process for purification of the n-butyl isocyanate of an embodiment, comprise the following steps:
S110, provide n-butyl isocyanate solution to be refined.
Above-mentioned n-butyl isocyanate solution to be refined is provided by following steps: dimethylbenzene and n-butylamine is mixed, drips hydrochloric acid, obtain the mixed solution containing n-butylamine hydrochlorate；The above-mentioned mixed liquor solution containing n-butylamine hydrochlorate is heated, under reflux conditions azeotropic dehydration, until moisture takes off, obtain n-butylamine hydrochlorate dimethylbenzene material；Above-mentioned n-butylamine hydrochlorate dimethylbenzene material is carried out logical phosgene reaction, obtains the mixture containing n-butyl isocyanate；Finally the above-mentioned mixture containing n-butyl isocyanate is carried out rectification, obtain n-butyl isocyanate solution to be refined.
Concrete, by dimethylbenzene, n-butylamine by measuring head tank, quantitatively putting into salt-forming reactor, drip hydrochloric acid in the cooling condition, produce the mixed solution containing n-butylamine hydrochlorate；Then by steam jacket heat temperature raising, azeotropic dehydration under counterflow condition, till being taken off by moisture, obtain n-butylamine hydrochlorate dimethylbenzene material；N-butylamine hydrochlorate dimethylbenzene material is pressed into photochemical reaction pot, under reflux conditions, carries out logical phosgene reaction, until n-butylamine hydrochlorate is completely converted into n-butyl isocyanate, then catch up with light, obtain the mixture containing n-butyl isocyanate and separate for rectification；Finally the above-mentioned mixture containing n-butyl isocyanate is added rectifying column, carry out infinite reflux to tower top with high temperature heat conductive oil heating, obtain n-butyl isocyanate solution to be refined.
In above-mentioned isocyanate solution to be refined, mass content >=99.0% of n-butyl isocyanate, mass content ＞ 0.5% of impurity free acid.
It is appreciated that, above-mentioned n-butyl isocyanate solution to be refined is not limited to above step to be provided, as long as mass content >=99.0% of the n-butyl isocyanate produced, mass content ＞ 0.5% of impurity free acid can use process for purification herein to refine.
S120, at-10 DEG C ~-5 DEG C, while stirring toward above-mentioned n-butyl isocyanate solution to be refined adds aluminum chloride and dropping sodium hydroxide solution, react 0.5 ~ 1 hour, obtain mixed liquor.
Wherein, the concentration of sodium hydroxide solution is 0.2mol/L ~ 0.25mol/L.
The time of dropping sodium hydroxide solution is 0.5 ~ 1 hour.
In the step s 120, the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined is 1:0.05:5 ~ 6.
Preferably, the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined is 1:0.05:5.5.
Owing to the catalytic action of aluminum chloride, impurity free acid and cotton-shaped muddy thing thoroughly react with sodium hydroxide, improve product quality.
S130, by above-mentioned mixed liquor stand, layering, take upper organic layer and carry out separating-purifying, obtain n-butyl isocyanate.
Wherein, the time of standing is 30 ~ 60 minutes.
Take upper organic layer and carry out separating-purifying, obtain the step of n-butyl isocyanate particularly as follows: take upper organic layer to carry out decompression distillation, collect fraction, obtain n-butyl isocyanate.
Wherein, the vacuum≤-0.09MPa of decompression distillation.
It should be noted that above-mentioned mixed liquor stands, layering, the lower floor's inorganic layer obtained passes through sewage plant harmless treatment, produces without waste water and gas, pollutes few, safety and environmental protection.
The process for purification of above-mentioned n-butyl isocyanate, under the effect of catalyst aluminum chloride, impurity free acid contained in n-butyl isocyanate solution to be refined and poly-n-butyl isocyanate floccule is neutralized with sodium hydroxide, can be by impurity free acid and floccule separating-purifying, and the normal-butyl cyanate steady quality after purifying, can long term storage never degenerate.
It it is below specific embodiment.
Embodiment 1
Thering is provided n-butyl isocyanate solution 500L to be refined, through analyzing, the mass content of n-butyl isocyanate is 99.1%, and the mass content of free acid is 0.69%, and there is a large amount of White Flocculus the inside.
At-8 DEG C, aluminum chloride and the sodium hydroxide solution of dropping 0.2mol/L is added while stirring toward above-mentioned n-butyl isocyanate solution to be refined, react 1 hour, obtaining mixed liquor, the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined is 1:0.05:5.5.
Above-mentioned mixed liquor is stood 60 minutes, takes upper organic layer and carry out decompression distillation, collect fraction, obtain 480L sample.Through analyzing, in sample, the mass content of n-butyl isocyanate is 99.63%, and the mass content of free acid is 0.09%, and clear appearance is transparent；The mass content of n-butyl isocyanate after 7 days placed by sample is 99.61%, and the mass content of free acid is 0.09%, and clear appearance is transparent, without flocculent substance.
Embodiment 2
Thering is provided n-butyl isocyanate solution 1000L to be refined, through analyzing, the mass content of n-butyl isocyanate is 99.21%, and the mass content of free acid is 0.75%, and there is a large amount of White Flocculus the inside.
At-10 DEG C, aluminum chloride and the sodium hydroxide solution of dropping 0.23mol/L is added while stirring toward above-mentioned n-butyl isocyanate solution to be refined, react 1 hour, obtaining mixed liquor, the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined is 1:0.05:5.
Above-mentioned mixed liquor is stood 30 minutes, takes upper organic layer and carry out decompression distillation, collect fraction, obtain 985L sample.Through analyzing, in sample, the mass content of n-butyl isocyanate is 99.7%, and the mass content of free acid is 0.06%, and clear appearance is transparent；The mass content of n-butyl isocyanate after 14 days placed by sample is 99.69%, and the mass content of free acid is 0.06%, and clear appearance is transparent, without flocculent substance.
Embodiment 3
Thering is provided n-butyl isocyanate solution 1500L to be refined, through analyzing, the mass content of n-butyl isocyanate is 99.23%, and the mass content of free acid is 0.72%, and there is a large amount of White Flocculus the inside.
At-7 DEG C, aluminum chloride and the sodium hydroxide solution of dropping 0.25mol/L is added while stirring toward above-mentioned n-butyl isocyanate solution to be refined, react 1 hour, obtaining mixed liquor, the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined is 1:0.05:5.5.
Above-mentioned mixed liquor is stood 45 minutes, takes upper organic layer and carry out decompression distillation, collect fraction, obtain 1480L sample.Through analyzing, in sample, the mass content of n-butyl isocyanate is 99.78%, and the mass content of free acid is 0.04%, and clear appearance is transparent；After placing 28 days, the mass content of n-butyl isocyanate is 99.75%, and the mass content of free acid is 0.05%, and clear appearance is transparent, without flocculent substance.
Embodiment described above only have expressed the several embodiments of the present invention, and it describes more concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that, for the person of ordinary skill of the art, without departing from the inventive concept of the premise, it is also possible to make some deformation and improvement, these broadly fall into protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (8)
1. the process for purification of a n-butyl isocyanate, it is characterised in that comprise the following steps:
N-butyl isocyanate solution to be refined is provided；
At-10 DEG C ~-5 DEG C, n-butyl isocyanate solution to be refined toward described in while stirring adds aluminum chloride and dropping sodium hydroxide solution, reacts 0.5 ~ 1 hour, obtain mixed liquor；And
Described mixed liquor is stood, is layered, take upper organic layer and carry out separating-purifying, obtain n-butyl isocyanate；
The concentration of described sodium hydroxide solution is 0.2mol/L ~ 0.25mol/L；
The mass ratio of described n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined is 1:0.05:5 ~ 6.
The process for purification of n-butyl isocyanate the most according to claim 1, it is characterised in that described in the mass ratio of n-butyl isocyanate solution, aluminum chloride and sodium hydroxide solution to be refined be 1:0.05:5.5.
The process for purification of n-butyl isocyanate the most according to claim 1, it is characterised in that the time of described dropping sodium hydroxide solution is 0.5 ~ 1 hour.
The process for purification of n-butyl isocyanate the most according to claim 1, it is characterised in that in the step stood by described mixed liquor, being layered, the time of described standing is 30 ~ 60 minutes.
The process for purification of n-butyl isocyanate the most according to claim 1, it is characterized in that, described in take upper organic layer and carry out separating-purifying, obtain the step of n-butyl isocyanate particularly as follows: take upper organic layer to carry out decompression distillation, collect fraction, obtain n-butyl isocyanate.
The process for purification of n-butyl isocyanate the most according to claim 5, it is characterised in that in the step of described decompression distillation, the vacuum≤-0.09MPa of decompression distillation.
The process for purification of n-butyl isocyanate the most according to claim 1, it is characterised in that described in n-butyl isocyanate solution to be refined provided by following steps:
Dimethylbenzene and n-butylamine are mixed, drips hydrochloric acid, obtain the mixed solution containing n-butylamine hydrochlorate；
The described mixed solution containing n-butylamine hydrochlorate is heated, under reflux conditions azeotropic dehydration, until moisture takes off, obtain n-butylamine hydrochlorate dimethylbenzene material；
Described n-butylamine hydrochlorate dimethylbenzene material is carried out logical phosgene reaction, obtains the mixture containing n-butyl isocyanate；And
The described mixture containing n-butyl isocyanate is carried out rectification, obtain described in n-butyl isocyanate solution to be refined.
The process for purification of n-butyl isocyanate the most according to claim 1, it is characterised in that described in n-butyl isocyanate solution to be refined, mass content >=99.0% of n-butyl isocyanate, mass content ＞ 0.5% of impurity free acid.
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| CN105384659A (en) * | 2015-10-26 | 2016-03-09 | 安徽广信农化股份有限公司 | Method for synthesizing n-butyl isocyanate |
| CN110218163A (en) * | 2019-05-20 | 2019-09-10 | 江苏蓝丰生物化工股份有限公司 | The synthetic method of n-butyl isocyanate |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094894A (en) * | 1977-03-23 | 1978-06-13 | E. I. Du Pont De Nemours And Company | Process of purifying aliphatic isocyanates |
| EP1046636A3 (en) * | 1999-03-30 | 2002-06-19 | Bayer Ag | Process for the reduction of chlorine content of organic isocyanates |
| CN1844091A (en) * | 2006-05-08 | 2006-10-11 | 江苏安邦电化有限公司 | Process for preparing butyl isocyanate |
| CN101084187A (en) * | 2004-12-22 | 2007-12-05 | 朗盛德国有限责任公司 | Method for the reduction of chlorine-containing components in organic isocyanates |
| CN103638688A (en) * | 2013-12-24 | 2014-03-19 | 湖南国发精细化工科技有限公司 | Recycling method for phosgene in tail gas generated in calorescence reaction for synthesizing normal-butyl isocyanate |
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- 2014-11-27 CN CN201410692026.7A patent/CN104447411B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094894A (en) * | 1977-03-23 | 1978-06-13 | E. I. Du Pont De Nemours And Company | Process of purifying aliphatic isocyanates |
| EP1046636A3 (en) * | 1999-03-30 | 2002-06-19 | Bayer Ag | Process for the reduction of chlorine content of organic isocyanates |
| CN101084187A (en) * | 2004-12-22 | 2007-12-05 | 朗盛德国有限责任公司 | Method for the reduction of chlorine-containing components in organic isocyanates |
| CN1844091A (en) * | 2006-05-08 | 2006-10-11 | 江苏安邦电化有限公司 | Process for preparing butyl isocyanate |
| CN103638688A (en) * | 2013-12-24 | 2014-03-19 | 湖南国发精细化工科技有限公司 | Recycling method for phosgene in tail gas generated in calorescence reaction for synthesizing normal-butyl isocyanate |
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Application publication date: 20150325 Assignee: Hunan Weimo New Material Co.,Ltd. Assignor: HUNAN GOFAR FINE CHEMICAL TECH. CO.,LTD. Contract record no.: X2023980047358 Denomination of invention: Refining method of n-butyl isocyanate Granted publication date: 20161005 License type: Common License Record date: 20231120 |