CN109485583A - The preparation method of N, N '-diisopropylcarbodiimide - Google Patents
The preparation method of N, N '-diisopropylcarbodiimide Download PDFInfo
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- CN109485583A CN109485583A CN201811180796.8A CN201811180796A CN109485583A CN 109485583 A CN109485583 A CN 109485583A CN 201811180796 A CN201811180796 A CN 201811180796A CN 109485583 A CN109485583 A CN 109485583A
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- diisopropylcarbodiimide
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C267/00—Carbodiimides
Abstract
The invention belongs to technical field of organic synthesis, are specifically related to a kind of N, the preparation method of N '-diisopropylcarbodiimide.First N, N '-di-isopropyl thiourea are synthesized in a solvent with isopropylamine and carbon disulfide；To N, N '-di-isopropyl thiourea carries out once oxidation after being filtered, being dried；Secondary oxidation reaction is carried out, catalyst and oxidant is added, is reacted 1 hour at 60-65 DEG C；Desulfurization process is carried out, sodium sulfide solution is added into oxidation solution, is warming up to 70-75 DEG C, is reacted 1-2 hours；Add piece alkali neutralization, wash, branch vibration layer adds desiccant dryness, steams solvent, and rectification under vacuum obtains N, N '-diisopropylcarbodiimide.The waste water of the preparation method of N of the present invention, N '-diisopropylcarbodiimide, generation can be recycled, no discharge, no pollution to the environment；It feeds intake and post-processes simply, production cost is low, high income, purity is high.
Description
Technical field
The invention belongs to technical field of organic synthesis, are specifically related to a kind of N, the preparation of N '-diisopropylcarbodiimide
Method.
Background technique
Diisopropylcarbodiimide is a kind of chemical substance, and molecular formula is C7H14N2.N, N- diisopropylcarbodiimide
(DIC), character: colourless transparent liquid；Appearance: colourless to weak yellow liquid；Main content >=99.0%；Boiling point: 145-148 DEG C；
Density: 20 DEG C of 0.815g/mL at；93 °F of flash-point；Sensibility: water imbibition；Purposes: the condensation being mainly used as in Peptide systhesis
Agent.
At present carbodiimide compound be widely used in polymeric material additive, the synthesis of heterocyclic compound, biochemical industry,
Pharmacy, the manufacture of industrial dye intermediate and new type functional (insulation, fire-retardant) material, meanwhile, it is also industry and experiment
Room commonly synthesizes the low temperature dewatering agent of the compounds such as aldehyde, ketone, amino acid, acid anhydrides, ester, is that carboxylic acid and amine (or alcohol) are acylated
Mostly important one of reagent is reacted, is also played in synthesizing valuable and rare source macrolide and Macrocyclic lactams reaction
Unique effect.
N, N '-diisopropylcarbodiimide (DIC) are a kind of important fine chemical products, have biggish molecular weight,
Higher boiling point and lower vapour pressure have the performance of general carbodiimide compound, and under the conditions of non-catalytic very
Stablize, and show very strong reactivity under catalytic condition, is a kind of good organic reagent.
In the prior art for synthesizing N, the method for N '-diisopropylcarbodiimide mainly include the following types:
(1) using industrial isopropylamine, carbon disulfide as raw material, the hydrogen sulfide of a molecule is removed by being heated to reflux, and synthesizes N,
N '-di-isopropyl thiourea；Again using chloro diethylamine as oxidant, the hydrogen sulfide of another molecule of oxidation removal prepares N, and N '-two is different
Propyl carbodiimide, the H generated in this method synthesis process2S has very strong toxicity, and directly human body can be interfered to oxygen
Intake and transport, cause intracellular respiratory enzyme to lose vigor, and then cause cell hypoxia death by suffocation；What the method generated simultaneously is useless
Water is larger, and risk is high；
(2) with N, N '-di-isopropyl thiourea is reacted with lead oxide, and removing hydrogen sulfide is made.Except lead compound is to environment
Pollution is outer, and this method generates H2S has very strong toxicity, thus this method only in the lab a small amount of preparation when use.
(3) using isopropylamine, formaldehyde contracting isopropylamine and excessive sulphur as raw material, N is obtained by a series of processing, N '-two is different
Propyl carbodiimide, big using this method quantity of three wastes, industrial production is difficult.
There is the disadvantages of yield is low, risk is high, effect on environment is big in these methods, be not suitable for big to some extent
The industrialized production of scale.
Summary of the invention
The purpose of the present invention is overcome the deficiencies of the prior art and provide a kind of N, the preparation of N '-diisopropylcarbodiimide
Method.The waste water that the preparation method generates can be recycled, no discharge, no pollution to the environment；Feed intake and post-process simple, life
At low cost, high income is produced, purity is high.
The preparation method of N of the present invention, N '-diisopropylcarbodiimide, specifically includes the following steps:
(1) N is first synthesized in a solvent with isopropylamine and carbon disulfide, N '-di-isopropyl thiourea, and meanwhile it is molten with sodium hydroxide
The hydrogen sulfide gas generated during liquid absorbing reaction, the sodium sulfide solution of generation are used for the desulphurization reaction of secondary oxidation；
(2) to the N of step (1) preparation, N '-di-isopropyl thiourea filtered, dry after carry out once oxidation, together with piece
Alkali, catalyst, solvent sequentially add in primary first-order equation kettle, are warming up to 55-60 DEG C, and oxidant is added, anti-at 55 DEG C~65 DEG C
It answers 2 hours, stands 20-25min, discard lower layer's water phase, the preparation of next oxidation solution is used for after water phase filtering, not outlet；
(3) secondary oxidation reaction is carried out, catalyst and oxidant is added, is reacted 1 hour at 60-65 DEG C；
(4) desulfurization process is carried out, sodium sulfide solution is added into oxidation solution, is warming up to 70-75 DEG C, is reacted 1-2 hours；
(5) plus piece alkali neutralization, washing, branch vibration layer add desiccant dryness, steam solvent, and rectification under vacuum obtains N, N '-two
Diisopropylcarbodiimide.
Wherein:
The mass fraction of sodium hydroxide solution described in step (1) is 30%.
Solvent described in step (1) is toluene or dimethylbenzene.
Solvent described in step (2) is one of benzene, dimethylbenzene or methylene chloride；Catalyst is polyethylene glycol or benzyl
One of triethylammonium chloride.
Oxidant described in step (2) and step (3) is the liquor natrii hypochloritis of 26% mass concentration, and oxidant is to drip
The mode added is added, and controls and drip off in 3 hours.
The amount that catalyst is added in step (3) is N, the 1.5%-3% of N '-di-isopropyl thiourea quality.
Desiccant described in step (5) is one of calcium chloride, sulfate or potassium carbonate.
The mass ratio 1:0.5-0.8 of isopropylamine described in step (1) and carbon disulfide.
Once oxidation described in step (2), the amount of the oxidant of addition are N, 6 times of N '-di-isopropyl thiourea quality.
It is N, the 5%-10% of N '-di-isopropyl thiourea quality that the quality of piece alkali is added described in step (2)；Addition is urged
The quality of agent is N, the 15%-20% of N '-di-isopropyl thiourea quality.
As a preferred technical solution, N of the present invention, the preparation method of N '-diisopropylcarbodiimide, tool
Body the following steps are included:
(1) N is first synthesized in a solvent with isopropylamine and carbon disulfide, N '-di-isopropyl thiourea, while with 30% hydrogen-oxygen
Change the hydrogen sulfide gas generated during sodium solution absorbing reaction, desulfurization of the sodium sulfide solution of generation for secondary oxidation is anti-
It answers；
(2) to the N after filtering, drying, N '-di-isopropyl thiourea carries out once oxidation, together with piece alkali, catalyst, solvent
It sequentially adds in primary first-order equation kettle, is warming up to 55 DEG C, the hypochlorous acid of pre-configured 26% concentration of oxidant was dripped off with 3 hours
Sodium solution reacts 2 hours at 55 DEG C -65 DEG C, static 20 minutes, lower layer's water phase is discarded, for oxidation next time after water phase filtering
The preparation of liquid, not outlet；
(3) secondary oxidation reaction is carried out, adds catalyst, quantitative sodium hypochlorite is added dropwise, reacted 1 hour at 60 DEG C；
(4) desulfurization process is carried out, sodium sulfide solution is added into oxidation solution, is warming up to 70 DEG C, is reacted 1 hour；
(5) plus piece alkali neutralization, washing, branch vibration layer add desiccant dryness, steam solvent, and rectification under vacuum obtains N, N '-two
Diisopropylcarbodiimide.
Compared with the prior art, the present invention has the following beneficial effects:
The waste water of the preparation method of N of the present invention, N '-diisopropylcarbodiimide, generation can be recycled, nothing
Discharge, no pollution to the environment；It feeds intake and post-processes simply, production cost is low, high income, purity is high.
Detailed description of the invention
Fig. 1 is N of the present invention, N '-diisopropylcarbodiimide preparation method process flow chart.
Specific embodiment
The invention will be further described with reference to embodiments.
Embodiment 1
First 140Kg isopropylamine and 400Kg toluene are put into reaction kettle, 70Kg carbon disulfide, temperature is added dropwise in starting stirring
Degree control at 35 DEG C hereinafter, insulation reaction 1 hour, while with during the sodium hydroxide solution absorbing reaction of 30% mass fraction
The hydrogen sulfide gas of generation, the sodium sulfide solution of generation are used for the desulphurization reaction of secondary oxidation；Cooling filters, and drying obtains N,
N '-di-isopropyl thiourea.
By 100Kg N, N '-di-isopropyl thiourea, 400Kg benzene are added in another reaction kettle, add 5Kg piece alkali, and 15Kg is urged
Kettle temperature is raised to 60 DEG C by agent polyethylene glycol, and 600Kg sodium hypochlorite is added dropwise, and temperature controls between 55-65 DEG C, and reaction 2 is small
When, 20 minutes are stood, lower layer's water phase is discarded；The preparation of next oxidation solution is used for after water phase filtering, not outlet.
The complete oxidation solution of once oxidation is transferred in another kettle, 2Kg catalyst is added, 100L sodium hypochlorite, temperature control is added dropwise
System is reacted 1 hour at 65 DEG C or so.
150L sodium sulfide solution is added into kettle, is warming up to 70 DEG C, reacts 1 hour.
Add alkali 5Kg, water 300Kg, stir half an hour, stand 20 minutes, branch vibration layer adds 10Kg potassium carbonate dry, boils off
Solvent, rectification under vacuum obtain N, N '-diisopropylcarbodiimide.Yield 93%, 99.5% or more purity.
Embodiment 2
First 140Kg isopropylamine and 400Kg toluene are put into reaction kettle, 80Kg carbon disulfide, temperature is added dropwise in starting stirring
Degree control at 30 DEG C hereinafter, insulation reaction 1 hour, while with during the sodium hydroxide solution absorbing reaction of 30% mass fraction
The hydrogen sulfide gas of generation is warming up to 110 DEG C, insulation reaction 1 hour, cools down, filter, drying obtains N, N '-diisopropyl sulphur
Urea.
By N, N '-di-isopropyl thiourea 100Kg, 400Kg benzene is added in another reaction kettle, adds 5Kg piece alkali, 15Kg catalysis
Kettle temperature is raised to 60 DEG C by agent benzyltriethylammoinium chloride, and 600Kg sodium hypochlorite is added dropwise, and temperature controls between 55-65 DEG C, instead
It answers 2 hours, stands 20 minutes, discard lower layer's water phase.
The complete oxidation solution of once oxidation is transferred in another kettle, 2Kg catalyst is added, 100L sodium hypochlorite, temperature control is added dropwise
System is reacted 1 hour at 65 DEG C or so.
150L sodium sulfide solution is added into kettle, is warming up to 70 DEG C, reacts 1 hour.
Add alkali 5Kg, water 300Kg, stir half an hour, stand 20 minutes, branch vibration layer adds 10Kg potassium carbonate dry, boils off
Solvent, rectification under vacuum obtain N, N '-diisopropylcarbodiimide.Yield 94%, 99.5% or more purity.
Embodiment 3
First 140Kg isopropylamine and 400Kg toluene are put into reaction kettle, 70Kg carbon disulfide, temperature is added dropwise in starting stirring
Degree control at 35 DEG C hereinafter, insulation reaction 1 hour, while with during the sodium hydroxide solution absorbing reaction of 30% mass fraction
The hydrogen sulfide gas of generation cools down, and filters, and drying obtains N, N '-di-isopropyl thiourea.
By N, N '-di-isopropyl thiourea 120Kg, 400Kg benzene is added in another reaction kettle, adds 10Kg piece alkali, 20Kg is urged
Kettle temperature is raised to 60 DEG C by agent polyethylene glycol, and 600Kg sodium hypochlorite is added dropwise, and temperature controls between 55-65 DEG C, and reaction 2 is small
When, 20 minutes are stood, lower layer's water phase is discarded.
The complete oxidation solution of once oxidation is transferred in another kettle, 2Kg catalyst is added, 100L sodium hypochlorite, temperature control is added dropwise
System is reacted 1 hour at 65 DEG C or so.
150L sodium sulfide solution is added into kettle, is warming up to 70 DEG C, reacts 1 hour.
Add alkali 5Kg, water 300Kg, stir half an hour, stand 20 minutes, branch vibration layer adds 10Kg potassium carbonate dry, boils off
Solvent, rectification under vacuum obtain N, N '-diisopropylcarbodiimide.Yield 92%, 99.3% or more purity.
Claims (9)
1. the preparation method of a kind of N, N '-diisopropylcarbodiimide, it is characterised in that: specifically includes the following steps:
(1) N, N '-di-isopropyl thiourea are first synthesized in a solvent with isopropylamine and carbon disulfide, while being inhaled with sodium hydroxide solution
The hydrogen sulfide gas generated in reaction process is received, the sodium sulfide solution of generation is used for the desulphurization reaction of secondary oxidation；
(2) to the N of step (1) preparation, N '-di-isopropyl thiourea filtered, dry after carry out once oxidation, together with piece alkali,
Catalyst, solvent sequentially add in primary first-order equation kettle, are warming up to 55-60 DEG C, and oxidant is added, reacts 2 at 55 DEG C~65 DEG C
Hour, 20-25min is stood, lower layer's water phase is discarded, the preparation of next oxidation solution is used for after water phase filtering, not outlet；
(3) secondary oxidation reaction is carried out, catalyst and oxidant is added, is reacted 1 hour at 60-65 DEG C；
(4) desulfurization process is carried out, sodium sulfide solution is added into oxidation solution, is warming up to 70-75 DEG C, is reacted 1-2 hours；
(5) plus piece alkali neutralization, washing, branch vibration layer add desiccant dryness, steam solvent, and rectification under vacuum obtains N, N '-diisopropyl
Base carbodiimide.
2. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: in step (1)
The mass fraction of the sodium hydroxide solution is 30%；Solvent described in step (1) is toluene or dimethylbenzene.
3. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: in step (2)
The solvent is one of benzene, dimethylbenzene or methylene chloride；Catalyst is in polyethylene glycol or benzyltriethylammoinium chloride
One kind.
4. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: step (2) and
Oxidant described in step (3) is the liquor natrii hypochloritis of 26% mass concentration, and oxidant is added in a manner of being added dropwise, and is controlled
System drips off in 3 hours.
5. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: in step (3)
The amount that catalyst is added is N, the 1.5-3% of N '-di-isopropyl thiourea quality.
6. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: in step (5)
The desiccant is one of calcium chloride, sulfate or potassium carbonate.
7. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: in step (1)
The mass ratio of the isopropylamine and carbon disulfide is 1:0.5-0.8.
8. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: in step (2)
The once oxidation, the amount of the oxidant of addition are N, 6 times of N '-di-isopropyl thiourea quality.
9. the preparation method of N according to claim 1, N '-diisopropylcarbodiimide, it is characterised in that: in step (2)
The quality of the addition piece alkali is N, the 5%-10% of N '-di-isopropyl thiourea quality；The quality that catalyst is added is N, N '-
The 15%-20% of di-isopropyl thiourea quality.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112142625A (en) * | 2020-10-20 | 2020-12-29 | 山东汇海医药化工有限公司 | Method for reducing waste residues of N, N' -diisopropylcarbodiimide product |
| CN112142624A (en) * | 2020-10-19 | 2020-12-29 | 山东汇海医药化工有限公司 | Method for synthesizing N, N' -diisopropylcarbodiimide by using oxygen as oxidant |
| CN112250600A (en) * | 2020-10-20 | 2021-01-22 | 山东汇海医药化工有限公司 | Process method for improving yield of N, N' -diisopropylcarbodiimide product |
| CN115925582A (en) * | 2022-11-18 | 2023-04-07 | 山东汇海医药化工有限公司 | Preparation method of N, N' -diisopropylcarbodiimide |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4815824B1 (en) * | 1970-02-05 | 1973-05-17 | ||
| CN101096349A (en) * | 2006-06-26 | 2008-01-02 | 山东金城医药化工有限公司 | Production technique of N,N'-dicyclo hexylcar bodiimide |
| CN103288681A (en) * | 2013-07-04 | 2013-09-11 | 山西省化工研究所 | Process for producing N, N'-diisopropylbenzene carbodiimide by thiourea method |
| CN103382168A (en) * | 2013-07-31 | 2013-11-06 | 浙江普康化工有限公司 | Synthetic method for N,N'-diisopropyl carbodiimide |
| WO2015122216A1 (en) * | 2014-02-12 | 2015-08-20 | 公立大学法人大阪市立大学 | Method for producing carbodiimide compound |
| CN108084055A (en) * | 2017-12-27 | 2018-05-29 | 山东汇海医药化工有限公司 | A kind of method of N, N '-di-isopropyl thiourea oxidative synthesis N, N '-diisopropylcarbodiimide |
-
2018
- 2018-10-09 CN CN201811180796.8A patent/CN109485583A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4815824B1 (en) * | 1970-02-05 | 1973-05-17 | ||
| CN101096349A (en) * | 2006-06-26 | 2008-01-02 | 山东金城医药化工有限公司 | Production technique of N,N'-dicyclo hexylcar bodiimide |
| CN103288681A (en) * | 2013-07-04 | 2013-09-11 | 山西省化工研究所 | Process for producing N, N'-diisopropylbenzene carbodiimide by thiourea method |
| CN103382168A (en) * | 2013-07-31 | 2013-11-06 | 浙江普康化工有限公司 | Synthetic method for N,N'-diisopropyl carbodiimide |
| WO2015122216A1 (en) * | 2014-02-12 | 2015-08-20 | 公立大学法人大阪市立大学 | Method for producing carbodiimide compound |
| CN108084055A (en) * | 2017-12-27 | 2018-05-29 | 山东汇海医药化工有限公司 | A kind of method of N, N '-di-isopropyl thiourea oxidative synthesis N, N '-diisopropylcarbodiimide |
Non-Patent Citations (3)
| Title |
|---|
| 吕也博编: "《肥皂生产基本知识》", 31 October 1978, 轻工业出版社 * |
| 石得中，黄洪周主编: "《世界精细化工产品技术经济手册》", 31 December 1988, 化学工业部科学技术情报研究所 * |
| 赵丽华和延锦丽: "N, N′-二异丙基碳二亚胺的合成", 《齐鲁药事》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112142624A (en) * | 2020-10-19 | 2020-12-29 | 山东汇海医药化工有限公司 | Method for synthesizing N, N' -diisopropylcarbodiimide by using oxygen as oxidant |
| CN112142625A (en) * | 2020-10-20 | 2020-12-29 | 山东汇海医药化工有限公司 | Method for reducing waste residues of N, N' -diisopropylcarbodiimide product |
| CN112250600A (en) * | 2020-10-20 | 2021-01-22 | 山东汇海医药化工有限公司 | Process method for improving yield of N, N' -diisopropylcarbodiimide product |
| CN112250600B (en) * | 2020-10-20 | 2023-06-16 | 山东汇海医药化工有限公司 | Technological method for improving yield of N, N' -diisopropylcarbodiimide product |
| CN115925582A (en) * | 2022-11-18 | 2023-04-07 | 山东汇海医药化工有限公司 | Preparation method of N, N' -diisopropylcarbodiimide |
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