CN114507160A - Method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method - Google Patents
Method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method Download PDFInfo
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- CN114507160A CN114507160A CN202111472974.6A CN202111472974A CN114507160A CN 114507160 A CN114507160 A CN 114507160A CN 202111472974 A CN202111472974 A CN 202111472974A CN 114507160 A CN114507160 A CN 114507160A
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- pentamethylene diisocyanate
- phosgene
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 11
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 28
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000007789 gas Substances 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 12
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 238000007670 refining Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims abstract description 6
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims abstract description 6
- JTXJZBMXQMTSQN-UHFFFAOYSA-N amino hydrogen carbonate Chemical compound NOC(O)=O JTXJZBMXQMTSQN-UHFFFAOYSA-N 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 6
- 238000006552 photochemical reaction Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 229940072049 amyl acetate Drugs 0.000 claims description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 3
- 229960001047 methyl salicylate Drugs 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 25
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- IDKXMGZRWKCTGA-UHFFFAOYSA-N chloroimino(oxo)methane Chemical compound ClN=C=O IDKXMGZRWKCTGA-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/04—Preparation of derivatives of isocyanic acid from or via carbamates or carbamoyl halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation, which comprises the following operation steps: (1) introducing hydrogen chloride or carbon dioxide gas into the 1, 5-pentanediamine solution to generate amino hydrochloride or amino carbonate until the reaction is finished; (2) heating to 70-100 ℃, and introducing phosgene to react to generate carbamoyl chloride; (3) heating to 100-200 ℃ for carrying out a thermo-optic reaction to remove hydrogen chloride from carbamoyl chloride to generate 1, 5-pentamethylene diisocyanate photochemical liquid; (4) and (3) carrying out phosgene removal, solvent removal and product refining on the photochemical solution to obtain the product. The method has simple and easily controlled operation process and is suitable for industrial production.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and relates to a method for synthesizing 1, 5-pentamethylene diisocyanate by a salifying phosgenation method.
Background
1, 5-Pentanediisocyanate (PDI), also known as pentamethylene diisocyanate, belongs to a novel aliphatic diisocyanate, and the product and related derivatives thereof have excellent performance, higher activity compared with HDI (hexamethylene diisocyanate), can replace HDI in HDI and derivatives thereof, and have better performance. Usually, 1, 5-Pentanediamine (PDA) is synthesized by phosgenation, PDI is prepared into PDI biuret or tripolymer for producing polyurethane coating and adhesive, and the coating has the characteristics of no yellowing, strong weather resistance and the like. Foreign manufacturers are mainly created by scientific thought, the product is PDI tripolymer (Desmodur eco N7300), the product is put into the European market, the technical requirements of the railway vehicle industry are met, and the gloss stability, the wear resistance and the like are superior to HDI products. The production of PDI and its manufacturers are reported in China.
PDA is produced by biosynthesis of lysine, decarboxylation of lysine to synthesize 1, 5-pentanediamine. Compared with HDA (HDI raw material for producing HDI), the method has obvious production cost advantage and sufficient domestic goods sources. Because the PDI is superior to HDI products in gloss stability, wear resistance and the like of downstream products, the HDI can be completely replaced, the shortage of domestic HDI products is relieved, and the requirements of downstream customers are met.
Due to the relatively fast reaction rate of aliphatic amine and phosgene, amine coating is easily caused to generate monochloro isocyanate by-product in the subsequent thermal photochemical process, and finally, the hydrolytic chlorine in the product is increased, so that the use of downstream products is influenced.
Disclosure of Invention
The invention aims to avoid the defects of the prior art and provides a method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation.
In order to achieve the purpose, the invention adopts the technical scheme that: a salifying phosgenation method for synthesizing 1, 5-pentamethylene diisocyanate is characterized in that 1, 5-pentamethylene diamine is used as raw material to prepare 1, 5-pentamethylene diisocyanate, and the method comprises the following operation steps:
(1) mixing 1, 5-pentanediamine and an inert solvent to form a 1, 5-pentanediamine solution, and introducing hydrogen chloride or carbon dioxide gas into the 1, 5-pentanediamine solution at the temperature of-10 to 40 ℃ under the control of flow rate to generate amino hydrochloride or amino carbonate until the reaction is finished, wherein the reaction time is 1 to 5 hours;
(2) heating the amino hydrochloride or the amino carbonate solution to 70-100 ℃, and simultaneously introducing phosgene at a controlled flow rate for reaction to generate carbamoyl chloride, wherein the reaction time is 1-5 hours;
(3) heating to 100-200 ℃ for thermo-photochemical reaction, removing hydrogen chloride from carbamoyl chloride to generate 1, 5-pentamethylene diisocyanate photochemical liquid until the photochemical liquid is clear and transparent, and finishing the reaction;
(4) and (3) performing phosgene removal, solvent removal and product refining on the 1, 5-pentamethylene diisocyanate photochemical solution to obtain a qualified product.
In the step (1), an inert solvent and 1, 5-pentamethylene diamine are mixed into a 1, 5-pentamethylene diamine solution according to the mass ratio of 20:1-3: 1.
In the step (1), the molar ratio of the introduced hydrogen chloride or carbon dioxide gas to the 1, 5-pentanediamine is 10:1-2: 1.
In the step (1), the hydrogen chloride or carbon dioxide gas is continuously or intermittently fed, the flow rate is 50-500ml/min, and the feeding time is 2-8 h.
In the step (2), phosgene is introduced to be fed in a liquid phase or a gas phase, and the flow rate is 50-500 ml/min; the mass ratio of the total amount of phosgene used in the reaction to the 1, 5-pentanediamine is 15:1-4: 1.
The inert solvent is any one of toluene, chlorobenzene, dichlorobenzene, diethyl isophthalate, amyl acetate and methyl salicylate.
The invention has the beneficial effects that: the 1, 5-pentanediamine solution is introduced into hydrogen chloride or carbon dioxide gas at a certain flow rate to generate amino hydrochloride or amino carbonate until the reaction is finished, so that the phenomenon that the amine is coated and cannot participate in the reaction is effectively prevented, the generation of hydrolysis chlorine in the PDI product is correspondingly reduced, and the use of downstream products is met. The method has simple and easily controlled operation process and is suitable for industrial production.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
6kg of amyl acetate was added to a 20L glass kettle reactor, 1kg of 1, 5-Pentanediamine (PDA) was added, and after mixing well, hydrogen chloride was introduced into the glass kettle reactor through a gas flow meter at a flow rate of 100 ml/min. Controlling the temperature of the system at 20-30 ℃, and stopping introducing the hydrogen chloride after introducing for 4 hours; and (3) heating the temperature of the reaction kettle to 85 ℃ for photochemical reaction, introducing phosgene at the same time, continuously heating the gaseous phosgene to 150 ℃ after the reaction is carried out for 3 hours, and continuously introducing the phosgene until the photochemical solution is clear and transparent, wherein the flow rate of the phosgene is 400L/h. And (3) performing phosgene removal, solvent removal and product refining on the PDI photochemical solution to obtain a qualified PDI product. The yield of the PDI product is 95.8 percent, and the hydrolysis chlorine is 42 ppm.
Example 2
8.5kg of o-dichlorobenzene and 1kg of PDA were added into a 20L glass kettle reactor, and after mixing them well, carbon dioxide was introduced into the glass kettle reactor through a gas flow meter at a flow rate of 150 ml/min. Controlling the temperature of the system at 10-20 ℃, and stopping introducing carbon dioxide after introducing for 5 hours; and (3) heating the temperature of the reaction kettle to 70 ℃ for photochemical reaction, introducing phosgene at the same time, continuously heating the gaseous phosgene to 130 ℃ after 4 hours of reaction at a flow rate of 500L/h, and continuously introducing the phosgene at a constant flow rate until the photochemical solution is clear and transparent, and finishing the reaction. And (3) performing phosgene removal, solvent removal and product refining on the PDI photochemical solution to obtain a qualified PDI product. The yield of PDI product is 97.4%, and the hydrolysis chlorine is 35 ppm.
Example 3
3kg of chlorobenzene was added into a 20L glass kettle reactor, 1kg of PDA was added and mixed uniformly, and then hydrogen chloride was introduced into the glass kettle through a gas flow meter at a flow rate of 200 ml/min. Controlling the temperature of the system at 20-30 ℃, and stopping introducing the hydrogen chloride after introducing for 3 hours; and (3) heating the temperature of the reaction kettle to 100 ℃ for photochemical reaction, introducing phosgene at the same time, wherein the flow rate of gaseous phosgene is 350L/h, continuously heating to 160 ℃ after 4h of reaction, and continuously introducing phosgene, wherein the flow rate is kept unchanged until photochemical solution is clear and transparent, and the reaction is finished. And (3) the PDI photochemical liquid is subjected to phosgene removal, solvent removal and product refining to obtain a qualified PDI product. The yield of the PDI product is 98.9 percent, and the hydrolysis chlorine is 29 ppm. .
Example 4
12kg of methyl salicylate was added into a 20L glass kettle reactor, 1kg of PDA was added, and after uniform mixing, carbon dioxide was introduced into the glass kettle through a gas flow meter at a flow rate of 150 ml/min. Controlling the temperature of the system at 20-30 ℃, and stopping introducing carbon dioxide after introducing for 4 hours; and (3) heating the temperature of the reaction kettle to 80 ℃ for photochemical reaction, introducing phosgene at the same time, continuously heating the gaseous phosgene to 170 ℃ after 4 hours of reaction at the flow rate of 400L/h, and continuously introducing the phosgene at the constant flow rate until the photochemical solution is clear and transparent, and finishing the reaction. And (3) the PDI photochemical liquid is subjected to phosgene removal, solvent removal and product refining to obtain a qualified PDI product. The yield of the PDI product is 96.7 percent, and the hydrolysis chlorine is 48 ppm. .
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that are within the spirit and principle of the present invention are intended to be included therein.
Claims (6)
1. A salifying phosgenation method for synthesizing 1, 5-pentamethylene diisocyanate is characterized in that 1, 5-pentamethylene diamine is used as raw material to prepare 1, 5-pentamethylene diisocyanate, and the method comprises the following steps:
(1) mixing 1, 5-pentanediamine and an inert solvent to form a 1, 5-pentanediamine solution, and introducing hydrogen chloride or carbon dioxide gas into the 1, 5-pentanediamine solution at the temperature of-10 to 40 ℃ under the control of flow rate to generate amino hydrochloride or amino carbonate until the reaction is finished, wherein the reaction time is 1 to 5 hours;
(2) heating the amino hydrochloride or the amino carbonate solution to 70-100 ℃, and simultaneously introducing phosgene at a controlled flow rate for reaction to generate carbamoyl chloride, wherein the reaction time is 1-5 hours;
(3) heating to 100-200 ℃ for thermo-photochemical reaction, removing hydrogen chloride from carbamoyl chloride to generate 1, 5-pentamethylene diisocyanate photochemical liquid until the photochemical liquid is clear and transparent, and finishing the reaction;
(4) and (3) performing phosgene removal, solvent removal and product refining on the 1, 5-pentamethylene diisocyanate photochemical solution to obtain a qualified product.
2. The method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation as claimed in claim 1, characterized in that: in the step (1), an inert solvent and 1, 5-pentamethylene diamine are mixed into a 1, 5-pentamethylene diamine solution according to the mass ratio of 20:1-3: 1.
3. The method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method as claimed in claim 1, characterized in that: in the step (1), the molar ratio of the introduced hydrogen chloride or carbon dioxide gas to the 1, 5-pentanediamine is 10:1-2: 1.
4. The method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method as claimed in claim 1, characterized in that: in the step (1), the hydrogen chloride or carbon dioxide gas is continuously or intermittently fed, the flow rate is 50-500ml/min, and the feeding time is 2-8 h.
5. The method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method as claimed in claim 1, characterized in that: in the step (2), phosgene is introduced to be fed in a liquid phase or a gas phase, and the flow rate is 50-500 ml/min; the mass ratio of the total amount of phosgene used in the reaction to the 1, 5-pentanediamine is 15:1-4: 1.
6. A process for the synthesis of pentane-1, 5-diisocyanate by salification phosgenation according to claim 1 or 2, wherein: the inert solvent is any one of toluene, chlorobenzene, dichlorobenzene, diethyl isophthalate, amyl acetate and methyl salicylate.
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| CN202111472974.6A CN114507160A (en) | 2021-12-06 | 2021-12-06 | Method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115850116A (en) * | 2022-11-30 | 2023-03-28 | 摩珈(上海)生物科技有限公司 | Method for synthesizing 1, 5-pentamethylene diisocyanate by solvent-free supercritical catalysis |
| CN115894296A (en) * | 2022-11-17 | 2023-04-04 | 万华化学集团股份有限公司 | Isocyanate composition, modified isocyanate, polyurethane resin and optical material |
| CN115894298A (en) * | 2022-12-14 | 2023-04-04 | 甘肃银光聚银化工有限公司 | Post-treatment method for reducing hydrolysis chlorine of 1, 5-pentamethylene diisocyanate |
| CN116239502A (en) * | 2022-12-14 | 2023-06-09 | 上海奕朗化工有限公司 | Method for synthesizing 1, 5-pentanediol by 1, 5-pentanediamine |
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| CN115894298A (en) * | 2022-12-14 | 2023-04-04 | 甘肃银光聚银化工有限公司 | Post-treatment method for reducing hydrolysis chlorine of 1, 5-pentamethylene diisocyanate |
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| CN116239502B (en) * | 2022-12-14 | 2024-06-07 | 上海奕朗化工有限公司 | Method for synthesizing 1, 5-pentanediol by 1, 5-pentanediamine |
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Application publication date: 20220517 |