CN116239502A - Method for synthesizing 1, 5-pentanediol by 1, 5-pentanediamine - Google Patents
Method for synthesizing 1, 5-pentanediol by 1, 5-pentanediamine Download PDFInfo
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- CN116239502A CN116239502A CN202211611952.8A CN202211611952A CN116239502A CN 116239502 A CN116239502 A CN 116239502A CN 202211611952 A CN202211611952 A CN 202211611952A CN 116239502 A CN116239502 A CN 116239502A
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
A method for synthesizing 1, 5-Pentanediisocyanate (PDI) from 1, 5-Pentanediamine (PDA), comprising: s1, dissolving 1, 5-pentanediamine into an inert solvent, and placing the solvent in a constant temperature device at 0-80 ℃; s2, introducing phosgene and hydrogen chloride gas, and reacting for 4-36 hours under the pressure of 0.1-0.2MPa to finish the cold light gasification reaction stage; s3, continuously introducing phosgene, heating the system to 150-200 ℃, and reacting for 8-20h under the pressure of 0.2-0.4 MPa; s4, after the temperature is restored to the room temperature, residual phosgene and hydrogen chloride gas are removed; s5, removing the inert solvent in vacuum, and rectifying to obtain a high-purity product. According to the invention, the molar ratio of phosgene to HCl to PDA is regulated by adding HCl gas into phosgene, so that the generation of urea compounds, particularly tar resin compounds, can be effectively reduced, and the yield and purification efficiency of PDI are improved.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a method for synthesizing 1, 5-Pentanediamine (PDI) through 1, 5-Pentanediamine (PDA).
Background
The diisocyanate and the dihydric alcohol can generate a polyurethane polymer compound. The polymer can be used for synthesizing pigments, resins, textile hydrophobing agents, plastics, detergents, foams, elastomers, adhesives, paints and the like, and in particular, aliphatic polyurethanes are widely used in the market due to their excellent durability. At present, besides the service life and performance improvement of polymer materials, the sustainability of material preparation raw materials is also concerned.
1, 5-Pentanediisocyanate (PDI) is the first biobased diisocyanate, and PDI has more advantages in downstream products than Hexamethylene Diisocyanate (HDI) which is currently widely used: such as relatively lower cost, better gloss stability, abrasion resistance, etc. In industry, PDI is obtained by phosgene synthesis of 1, 5-Pentanediamine (PDA), and biuret or trimer thereof has been used for producing polyurethane paint, adhesive and the like, and has the characteristics of no yellowing, strong weather resistance and the like. The key raw material 1, 5-Pentanediamine (PDA) is obtained by fermenting corn, starch in the corn is firstly hydrolyzed by glycosylase to produce glucose, and then lysine is formed by fermentation; finally, 1, 5-Pentanediamine (PDA) is produced from lysine by fermentative expression of lysine decarboxylase.
Although PDI has achieved some industrial production, there are still problems in the production process of PDA and phosgene liquid phase reaction, such as by-product generation and coating of raw materials due to the too fast reaction rate of the luminescence reaction stage. Particularly, urea compounds generated in the reaction process consume raw materials, so that the final yield is reduced, and the urea compounds can further react with phosgene to generate tar resin compounds, so that the post-treatment difficulty is increased, and the product purity is reduced.
The presence of tar resin compounds ultimately adversely affects the performance of the downstream product conversion process and the corresponding downstream product produced. For example, in the process of preparing polyurethane foaming materials, tar resin compounds can damage the uniformity of the materials, and finally the obtained materials have the problems of reduced buffering performance, reduced service life and the like; the tar resin compound can also have adverse effect on the movement of the high molecular chain of the polyurethane material, damage the mechanical properties of the corresponding elastomer material, reduce the strength and toughness of the material, and the like.
Therefore, optimizing the traditional liquid phase phosgenation method, inhibiting the production of byproduct tar resin compound has important significance for improving the yield and purity of PDI products, and even more for improving the performance and prolonging the service life of downstream products.
Chinese patent publication CN114507160a discloses a method for synthesizing 1, 5-pentanediisocyanate by salt phosgenation; and introducing hydrogen chloride or carbon dioxide gas before the cold light gas reaction stage to generate amino hydrochloride or amino carbonate. The method has the advantages of effectively slowing down the reaction rate of fatty amine and phosgene, inhibiting the generation of monochloroisocyanate, raw material amine (released by coating in the last stage) and product polymerization byproducts, and finally realizing the improvement of the product purity. However, this method requires a large amount of organic solvent for dispersion due to poor solubility of amine salt in the organic solvent, thereby extending the reaction time in the phosgenation reaction stage, and simultaneously requiring distillation for removing a large amount of solvent. As disclosed in uk patent publication GB1086782 a. Secondly, the amine salt precipitation process easily causes pipeline blockage, influences equipment use, and causes potential safety hazards in the preparation production process.
There have been a number of other studies attempting to optimize this from the salification process:
chinese CN200680022170.3 discloses a method for producing isocyanate, isocyanate obtained by the method and use thereof, in which the salt formation conversion rate and space-time efficiency are improved by increasing the temperature and reaction pressure to reduce the viscosity of hydrochloride; however, the high temperature limits the expansion of the reaction-like substrates and increases the reaction rate to adversely affect the reaction rate.
Chinese patent publication CN115093348A discloses a method for preparing isocyanate by a pipeline phosgene method, wherein an acyl chloride generating reaction and an acyl chloride decomposing reaction are performed in steps by a pipeline phosgenation method, so that side reactions of a target product and an intermediate product are effectively prevented, and phosgene is used as a reaction solvent, so that an organic solvent is avoided. However, this solution is highly demanding in terms of equipment and the overall high temperature not only makes the photochemical process less stable, but also is prone to carbonization products. Although the above patent documents all improve the disadvantages of the salt phosgenation method in different ways and can improve the product conversion to a certain extent, the existence of tar resin compounds which affect the performance of the product and downstream products thereof is not considered, and a strategy for effectively avoiding or reducing the generation of the byproducts is not proposed.
In summary, how to effectively utilize hydrochloride to reduce activity in the cold gasification reaction stage, stabilize the reaction, inhibit the formation of byproduct tar resin compound, and improve product conversion and purity, so as to avoid the drawbacks of the above method, and has important significance for efficiently preparing high-purity 1, 5-pentanediol and its corresponding downstream products (such as polyurethane materials).
Disclosure of Invention
In view of the above problems in the prior art, it is an object of the present invention to provide a method for synthesizing 1, 5-Pentanediol (PDI) from 1, 5-Pentanediamine (PDA), wherein the generation of urea compounds, particularly tar resin compounds, can be effectively reduced by adding HCl gas to phosgene and adjusting the molar ratio of phosgene to HCl to PDA, and the yield and purification efficiency of PDI can be improved.
In order to achieve the above object, the process steps of the method of the present invention comprise:
s1, dissolving 1, 5-pentanediamine into an inert solvent, rapidly stirring and uniformly mixing, and then placing the system into a constant temperature device with the temperature of 0-80 ℃;
s2, introducing phosgene and hydrogen chloride gas into the system at a constant speed, and reacting for 4-36 hours under the pressure of 0.1-0.2MPa to complete the cold light gasification reaction stage;
s3, continuously introducing phosgene, and heating the system to 150-200 ℃; after the system temperature is constant, reacting for 8-20 hours under the pressure of 0.2-0.4MPa until the photochemical liquid is clear and transparent;
s4, after the reaction is finished and the system is restored to room temperature, removing residual phosgene and hydrogen chloride gas under the vacuum degree (micro low pressure) of 50-100mmHg, and collecting and recycling;
s5, removing the inert solvent in vacuum, and rectifying the crude product to obtain a high-purity 1, 5-pentanediisocyanate product. The reaction formula (I) is as follows:
in the step S1, the inert solvent is alkyl substituted benzene such as toluene and xylene, halogenated benzene such as chlorobenzene, dichlorobenzene and trichlorphene, halogenated aryl derivative such as naphthalene chloride, diethyl isophthalate, amyl acetate or methyl salicylate; dichlorobenzene is preferred.
Further, in S1, the concentration of the inert solvent is selected taking into consideration the influence of the concentration on the reaction rate, and the case where the coating reactant may be salted out by the generated hydrochloric acid, so that a moderate concentration is selected. The concentration of the inert solvent is 1 to 10mol/L, preferably 3 to 7mol/L or preferably 4 to 6mol/L.
Further, in S1, the temperature is 20 to 60℃and preferably 30 to 50 ℃.
Further, in S2, a low temperature long-term reaction is employed to ensure the absence of the monosubstituted carbamoyl chloride intermediate. The duration of the cold light gasification reaction is 16-36h, preferably 25-30h; and/or the reaction time is not less than 16, 18 and 22 hours.
Further, in S2, the inflow rate of phosgene is controlled to be 20-500cm 3 Preferably 50-500 cm/min 3 /min or preferably 100-400cm 3 /min。
Further, in S2, the introduction of hydrogen chloride gas and the flow rate control thereof are used for suppressing the generation of urea byproducts. The inflow rate of hydrogen chloride gas is controlled to be 4-100cm 3 Preferably 10-50cm per minute 3 /min or preferably 10-20cm 3 /min。
Further, in S2, the ratio of the introduction rates of phosgene and hydrogen chloride is in the range of 5:1 to 50:1, preferably 10:1 to 20:1 or preferably 12:1 to 15:1.
Further, in S2, rapid agitation is maintained to prevent the coating of the starting materials with the possibly formed hydrochloride salt from affecting the reaction progress.
Further, in S2, the reaction pressure of the cold light gasification reaction is 0.12-0.18MPa or 0.15-0.17MPa. Further, in S3, the inflow rate of phosgene is 20-250cm 3 Preferably 50-500 cm/min 3 /min or preferably 100-300cm 3 /min。
Further, in S3, the system is warmed to 160-185℃or preferably 172℃173℃174℃175℃176 ℃.
Further, in S3, a slow temperature rise is employed to promote the reaction to proceed stably toward the product 1, 5-Pentanediisocyanate (PDI). The temperature rise rate is thus 10-20 deg.C/h, preferably 15-20 deg.C/h or preferably 15-18 deg.C/h.
Further, in S3, the reaction pressure is 0.12 to 0.18MPa, preferably 0.15 to 0.17MPa.
Further, in S4, the vacuum value at the time of removing phosgene or hydrogen chloride gas is 50 to 100mmHg, preferably 60 to 90mmHg.
Further, in S5, inert gas is removed in vacuum at a temperature of 50-70 ℃.
Compared with the prior art, the invention has the technical advantages that:
(1) Through the use of the mixed gas of phosgene and hydrogen chloride in the cold photochemical stage, the raw materials react with hydrochloric acid or phosgene to form competition, so that the overall reaction rate is reduced, the generation of byproducts caused by the excessively fast reaction is reduced, and the reaction is fast and stable to the direction of a carbamoyl chloride intermediate;
(2) The existence of phosgene enables hydrochloride to be carried out towards the direction of a product in a luminescence stage, so that the overall content of the hydrochloride in the reaction is reduced, the use amount of an organic solvent is reduced, and the risk of solid blockage is reduced;
(3) The hydrogen chloride gas can effectively inhibit the generation of urea compounds which are byproducts of consumed raw materials, and the reaction yield is improved;
(4) The urea compound further reacts with phosgene to generate tar resin compound with reduced content, so that the post-treatment and purification process of the product is effectively simplified, the purity of the product is improved, and finally the 1, 5-Pentanediol Diisocyanate (PDI) product with the purity of more than 99% can be obtained;
(5) In the stage of thermal phosgenation, the temperature is slowly increased to effectively promote the reaction to proceed towards the direction of the product, reduce the impurity content of the product and further improve the process efficiency.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the 1, 5-pentanediisocyanate product prepared in example 1.
Detailed Description
The invention will now be further described with reference to fig. 1.
Example 1:
PDA (2.5 kg) and dichlorobenzene (5L) as inert solvent are added into a 10L reaction kettle, and the gas in the nitrogen replacement device is blown into the system, and the system is stirred for 30min at a constant temperature of 30 ℃.
15cm was introduced into the system via a flow meter 3 Hydrogen chloride gas/min and 150cm 3 Phosgene/min, during which the rapid stirring reaction was maintained for 18h to complete the cold light reaction stage.
Continuously introducing 150cm 3 And (3) heating the system to 175 ℃ according to the heating rate of 15 ℃/h for carrying out a thermal-optical reaction stage by phosgene per minute, and continuing to react for 18 hours until the reaction is finished after the system temperature is stable. After the reaction solution was cooled to room temperature, residual phosgene and hydrogen chloride gas were collected under a vacuum of 50mmHg and treated. After that, dichlorobenzene in the reaction liquid is removed in vacuum at the temperature of 50 ℃, and the obtained crude product is rectified to obtain the product PDI (yield 95.3%).
Example 2:
PDA (2.5 kg) and chlorobenzene (5L) as inert solvent are added into a 10L reaction kettle, nitrogen is blown into the system to replace the gas in the device, and the system temperature is set to be constant at 0 ℃ and stirred for 30min.
15cm was introduced into the system via a flow meter 3 Hydrogen chloride gas/min and 150cm 3 Phosgene/min, during which the rapid stirring reaction was maintained for 20h to complete the cold light gas reaction stage.
Continuously introducing 150cm 3 And (3) heating the system to 175 ℃ according to the heating rate of 15 ℃/h for carrying out a thermal-optical reaction stage by phosgene per minute, and continuing to react for 12 hours until the reaction is finished after the system temperature is stable. After the reaction solution was cooled to room temperature, residual phosgene and hydrogen chloride gas were collected under a vacuum of 70mmHg and treated. After that, dichlorobenzene in the reaction liquid is removed in vacuum at the temperature of 65 ℃, and the obtained crude product is rectified to obtain the product PDI (yield 92.5%).
Example 3:
PDA (2.5 kg) and naphthalene chloride (5L) serving as an inert solvent are added into a 10L reaction kettle, and the gas in a nitrogen replacement device is blown into the system, so that the system temperature is set to be 30 ℃ and the system is stirred for 30min at constant temperature.
15cm was introduced into the system via a flow meter 3 Hydrogen chloride gas/min and 300cm 3 Phosgene/min, during which the rapid stirring reaction was maintained for 35h to complete the cold light gas reaction stage.
Continuously introducing 150cm 3 And (3) heating the system to 175 ℃ according to the heating rate of 15 ℃/h for carrying out a thermal-optical reaction stage by phosgene per minute, and continuing the reaction for 8 hours until the reaction is finished after the system temperature is stable. After the reaction solution was cooled to room temperature, residual phosgene and hydrogen chloride gas were collected under a vacuum of 95mmHg and treated. After that, dichlorobenzene in the reaction liquid is removed in vacuum at the temperature of 60 ℃, and the obtained crude product is rectified to obtain the product PDI (yield 95.2%).
Example 4:
PDA (2.5 kg) and toluene (5L) as inert solvents were added to a 10L reactor, and the gas in the nitrogen substitution device was purged into the system, and the system was stirred at a constant temperature of 30℃for 30 minutes.
15cm was introduced into the system via a flow meter 3 Hydrogen chloride gas/min and 150cm 3 Phosgene/min, during which the rapid stirring reaction was maintained for 35h to complete the cold light gas reaction stage.
Continuously introducing 150cm 3 And (3) heating the system to 175 ℃ according to the heating rate of 15 ℃/h for carrying out a thermal-optical reaction stage by phosgene per minute, and continuing to react for 20 hours until the reaction is finished after the system temperature is stable. After the reaction solution was cooled to room temperature, residual phosgene and hydrogen chloride gas were collected under a vacuum of 60mmHg and treated. After that, dichlorobenzene in the reaction liquid is removed in vacuum at the temperature of 70 ℃, and the obtained crude product is rectified to obtain the product PDI (yield 91.2%).
Comparative example 1:
PDA (2.5 kg) and dichlorobenzene (5L) as inert solvent are added into a 10L reaction kettle, and the gas in the nitrogen replacement device is blown into the system, and the system is stirred for 30min at a constant temperature of 30 ℃. 150cm was introduced into the system via a flow meter 3 Phosgene of/min, during which the rapid stirring reaction is kept for 12 hours to finish the cold light gas reaction stage; continuously introducing 150cm 3 Phosgene was added per minute, and the temperature of the system was raised to 1 at a temperature-raising rate of 15℃per hourAnd (3) carrying out a thermal-optical reaction stage at 75 ℃, and continuing the reaction for 12 hours until the reaction is finished after the system temperature is stable. After the reaction liquid is cooled to room temperature, collecting residual phosgene and hydrogen chloride gas under micro pressure and treating; after that, dichlorobenzene in the reaction liquid was removed in vacuo, and the obtained crude product was subjected to rectification to obtain the product PDI (yield 77.6%).
Comparative example 2:
PDA (2.5 kg) and dichlorobenzene (5L) as inert solvent are added into a 10L reaction kettle, and the gas in the nitrogen replacement device is blown into the system, and the system is stirred for 30min at a constant temperature of 30 ℃. 10cm was introduced into the system via a flow meter 3 Hydrogen chloride gas/min and 100cm 3 Phosgene in/min, during which the rapid stirring reaction is kept for 10 hours to finish the cold light gas reaction stage; continuously introducing 100cm 3 And (3) phosgene is added in every minute, the system is quickly heated to 175 ℃ (the process lasts for about 30 minutes) to carry out a thermal-photo-chemical reaction stage, and the reaction is continued for 16 hours until the reaction is finished after the system temperature is stable. After the reaction liquid is cooled to room temperature, collecting residual phosgene and hydrogen chloride gas under micro pressure and treating; after that, dichlorobenzene in the reaction liquid was removed in vacuo, and the obtained crude product was subjected to rectification to obtain the product PDI (yield 89.4%).
General experimental raw material names in the following table: toluene (Tol), o-xylene (o-DMB), chlorobenzene (PhCl), o-dichlorobenzene (o-DCB); hydrogen chloride (HCl), phosgene (COCl) 2 )。
Table 1: PDI synthetic experimental data table
The above examples were all conducted under the same experimental conditions except for the conditions shown; the temperature 1 is the maintaining temperature of the cold light gasification reaction stage, and the temperature 2 is the maintaining temperature of the hot light gasification reaction stage; the yield is the mole ratio of the pure product after filtration, solvent removal and rectification to the actual feeding.
By contrast, the embodiment of the invention utilizes the hydrogen chloride gas mixture in the cold light gasification reaction stage to inhibit the generation of urea byproducts, thereby improving the conversion rate of raw materials. The low-content urea compound and the slow heating rate in the thermal phosgenation reaction stage effectively reduce the content of tar resin compound, thereby being beneficial to reducing the difficulty of post-treatment purification after crude treatment and improving the purity of the DPI product.
The embodiments of the present invention have been described above with reference to the accompanying drawings and examples, which are not to be construed as limiting the invention, and those skilled in the art can make modifications as required, all of which are within the scope of the appended claims.
Claims (10)
1. A process for the synthesis of 1, 5-pentanediisocyanate from 1, 5-pentanediamine, characterized by:
s1, dissolving 1, 5-pentanediamine into an inert solvent, stirring and mixing uniformly, and then placing the system into a constant temperature device with the temperature of 0-80 ℃;
s2, introducing phosgene and hydrogen chloride gas into the system at a constant speed, and reacting for 4-36 hours under the pressure of 0.1-0.2MPa to complete the cold light gasification reaction stage;
s3, continuously introducing phosgene, and heating the system to 150-200 ℃; reacting for 8-20h under the pressure of 0.2-0.4MPa until the photochemical liquid is clear and transparent when the system temperature is constant;
s4, after the temperature is restored to the room temperature, residual phosgene and hydrogen chloride gas are removed, and the recycling treatment is carried out;
s5, removing the inert solvent, and rectifying to obtain the high-purity 1, 5-pentanediisocyanate product.
2. The method according to claim 1, characterized in that: in S1, the inert solvent is alkyl substituted benzene such as toluene and dimethylbenzene, halogenated benzene such as chlorobenzene, dichlorobenzene and trimesic benzene, halogenated aryl derivative such as naphthalene chloride, diethyl isophthalate, amyl acetate or methyl salicylate;
and/or the concentration of the inert solvent is 1-10mol/L, 3-7mol/L or 4-6mol/L.
And/or the temperature is 20-60 ℃ or 30-50 ℃.
3. The method according to claim 1, characterized in that: s2, the duration of cold light gasification reaction is 16-36 hours or 25-30 hours; and/or the reaction time is not less than 16, 18 and 22 hours.
4. The method according to claim 1, characterized in that: s2, controlling the phosgene inflow rate to be 20-500cm 3 /min、50-500cm 3 /min or 100-400cm 3 A/min; and/or the inflow rate of hydrogen chloride gas is 4-100cm 3 /min、10-50cm 3 /min or 10-20cm 3 /min。
5. The method according to claim 1, characterized in that: in S2, the ratio of the introducing rates of phosgene and hydrogen chloride is 5:1-50:1, 10:1-20:1 or 12:1-15:1.
6. The method according to claim 1, characterized in that: in S2, the reaction pressure of cold light gasification reaction is 0.12-0.18MPa or 0.15-0.17MPa.
7. The method according to claim 1, characterized in that: in S3, the inflow rate of phosgene is 20-250cm 3 /min、50-500cm 3 /min or 100-300cm 3 /min。
8. The method according to claim 1, characterized in that: s3, heating the system to 160-185 ℃ or 172 ℃, 173 ℃, 174 ℃, 175 ℃ and 176 ℃; and/or the heating rate is 10-20 ℃/h, 15-20 ℃/h or 15-18 ℃/h; and/or the reaction pressure is 0.12-0.18MPa or 0.15-0.17MPa.
9. The method according to claim 1, characterized in that: in S4, the vacuum value is 50-100 or 60-90mmHg when removing phosgene and hydrogen chloride gas.
10. The method according to claim 1, characterized in that: in S5, inert gas is removed in vacuum, and the temperature is 50-70 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1729167A (en) * | 2002-12-20 | 2006-02-01 | 巴斯福股份公司 | Method for the production of isocyanates |
| CN1956948A (en) * | 2004-05-25 | 2007-05-02 | 巴斯福股份公司 | Isocyanate production method |
| CN101671275A (en) * | 2009-09-18 | 2010-03-17 | 赛鼎工程有限公司 | Method for continuously manufacturing toluene di-isocyanate |
| CN102850239A (en) * | 2007-01-17 | 2013-01-02 | 巴斯夫欧洲公司 | Method for producing isocyanates |
| CN114507160A (en) * | 2021-12-06 | 2022-05-17 | 甘肃银光聚银化工有限公司 | Method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method |
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- 2022-12-14 CN CN202211611952.8A patent/CN116239502A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1729167A (en) * | 2002-12-20 | 2006-02-01 | 巴斯福股份公司 | Method for the production of isocyanates |
| CN1956948A (en) * | 2004-05-25 | 2007-05-02 | 巴斯福股份公司 | Isocyanate production method |
| CN102850239A (en) * | 2007-01-17 | 2013-01-02 | 巴斯夫欧洲公司 | Method for producing isocyanates |
| CN101671275A (en) * | 2009-09-18 | 2010-03-17 | 赛鼎工程有限公司 | Method for continuously manufacturing toluene di-isocyanate |
| CN114507160A (en) * | 2021-12-06 | 2022-05-17 | 甘肃银光聚银化工有限公司 | Method for synthesizing 1, 5-pentamethylene diisocyanate by salifying phosgenation method |
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