CN115010627A - Catalytic synthesis method of pentamethyldicarbamate - Google Patents
Catalytic synthesis method of pentamethyldicarbamate Download PDFInfo
- Publication number
- CN115010627A CN115010627A CN202210791881.8A CN202210791881A CN115010627A CN 115010627 A CN115010627 A CN 115010627A CN 202210791881 A CN202210791881 A CN 202210791881A CN 115010627 A CN115010627 A CN 115010627A
- Authority
- CN
- China
- Prior art keywords
- molecular sieve
- nickel
- values
- synthesis method
- treatment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
- B01J29/14—Iron group metals or copper
- B01J29/146—Y-type faujasite
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a catalytic synthesis method of pentanedicarbamic acid ester, which comprises the following steps: diethyl carbonate, alcohol, pentanediamine and Ni-HY molecular sieve catalyst are mixed and stirred for reaction to obtain the pentanedicarbamate. The method has the advantages of high pentamethylene diamine conversion rate up to 100%, high pentamethylene dicarbamate yield higher than 90%, mild reaction conditions, short reaction time, no pollution, low equipment requirement and suitability for industrial production.
Description
Technical Field
The invention belongs to the field of organic synthesis, relates to a synthesis method of pentanedicarbamic acid ester, and particularly relates to a catalytic synthesis method of pentanedicarbamic acid ester.
Background
Pentamethylene Diisocyanate (PDI) is a special aliphatic isocyanate, and compared with aromatic phenyl isocyanate, diphenylmethane diisocyanate and other linear alkane structures, the PDI endows the polyurethane derivative with excellent glossiness, yellowing resistance and weather resistance, and has wide application in the directions of automobile coatings, refinishing paints, high-grade furniture paints and light-resistant adhesives.
Currently, PDI can be synthesized by a traditional phosgene method, but the phosgene method has limitation on a synthetic route due to severe toxicity, complex process route, high equipment maintenance cost and large environmental risk. The non-phosgene process has therefore become the main direction of research. The pyrolytic synthesis of PDI from Pentanedicarbamate (PDC) has attracted extensive attention because of its mild conditions and recyclable by-products. Thus, the preparation of PDC is a key step of the technology.
CN108689884A adopts zinc compounds such as zinc oxalate to catalyze urea and PDA extract liquid to carry out carbamate synthesis in an autoclave so as to further synthesize PDI, but the synthesized butyl carbamate has low yield.
Therefore, there is a need to find a process that is milder, simple to operate and capable of efficiently synthesizing PDC.
Disclosure of Invention
In order to solve the technical problems, the invention provides a catalytic synthesis method of the pentanedicarbamic acid ester, the conversion rate of the pentanediamine in the synthesis method reaches 100%, the yield of the pentanedicarbamic acid ester is more than 90%, the reaction condition is mild, the reaction time is short, no pollution is caused, the requirement on equipment is low, and the method is suitable for industrial production.
In order to achieve the technical effect, the invention adopts the following technical scheme:
the invention provides a catalytic synthesis method of pentanedicarbamic acid ester, which comprises the following steps: diethyl carbonate, alcohol, pentanediamine and Ni-HY molecular sieve catalyst are mixed and stirred for reaction to obtain the pentanedicarbamate.
According to the invention, the Ni-HY catalyst is selected, the structure of the molecular sieve enables Ni to be highly dispersed, the improvement of catalytic activity is facilitated, the generation of byproducts is reduced, the yield of the glutaraldehyde ester is greatly improved, and meanwhile, the Ni-HY catalyst has the advantages of high stability, easiness in recovery, low price, reusability and the like. In addition, the invention adopts diethyl carbonate as the carbonylation agent, which can avoid the azeotropic problem of dimethyl carbonate and solvent methanol, and ethanol is easier to separate from the reaction system, thereby reducing the separation energy consumption and the synthesis cost.
In a preferred embodiment of the present invention, the mole of the pentamethylene diamine and diethyl carbonate is 1 (4-8), such as 1:4.5, 1:5, 1:5.5, 1:6, 1:6.5, 1:7 or 1:7.5, but the present invention is not limited to the above-mentioned values, and other values not shown in the above-mentioned range are also applicable.
Preferably, the molar ratio of pentamethylene diamine to alcohol is 1 (15-45), such as 1:20, 1:25, 1:30, 1:35 or 1:40, but not limited to the values listed, and other values not listed within this range are equally applicable.
Preferably, the mass ratio of the Ni-HY molecular sieve catalyst to diamine is (0.05-0.2):1, such as 0.06:1, 0.08:1, 0.1:1, 0.12:1, 0.15:1, or 0.18:1, and the like, but is not limited to the recited values and other values not recited within this range are equally applicable.
As a preferred embodiment of the present invention, the reaction temperature is 160-200 ℃, such as 165 ℃, 170 ℃, 175 ℃, 180 ℃, 185 ℃, 190 ℃ or 195 ℃, but is not limited to the values listed, and other values not listed within the range of values are also applicable.
Preferably, the reaction pressure is 1.5 to 2.2MPa, such as 1.6MPa, 1.7MPa, 1.8MPa, 1.9MPa, 2.0MPa or 2.1MPa, but not limited to the recited values, and other values not recited within the range of values are equally applicable.
Preferably, the reaction incubation time is from 5 to 12 hours, such as 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, or 11 hours, but is not limited to the recited values, and other values not recited within the range of values are equally applicable.
As a preferable technical scheme of the invention, the Ni-HY catalyst is prepared by adopting the following preparation method:
(1) stirring and mixing soluble salt of nickel and solvent water to obtain a mixed solution;
(2) adding an HY molecular sieve into the mixed solution in the step (1) under stirring, performing ultrasonic dispersion, and then sequentially performing drying and roasting treatment to obtain a solid product;
(3) and (3) carrying out reduction treatment on the solid product obtained in the step (2) to obtain the Ni-HY catalyst.
As a preferred embodiment of the present invention, the soluble salt of nickel in step (1) comprises any one or at least two combinations of nickel nitrate, nickel chloride, nickel sulfate or nickel acetate, and the combinations are exemplified by, but not limited to: a combination of nickel nitrate and nickel chloride, a combination of nickel chloride and nickel sulfate, a combination of nickel sulfate and nickel acetate, a combination of nickel acetate and nickel nitrate, a combination of nickel nitrate, nickel chloride and nickel acetate, and the like.
Preferably, the mass ratio of soluble salt to water is 1 (8-16), such as 1:9, 1:10, 1:11, 1:12, 1:13, 1:14, or 1:15, but not limited to the recited values, and other values not recited within this range are equally applicable.
In a preferred embodiment of the present invention, the mass ratio of the soluble salt of nickel to the HY molecular sieve in the mixed solution in step (2) is 0 to 20:100, excluding 0, such as 1:100, 2:100, 3:100, 4:100, 5:100, 6:100, 7:100, 8:100, 9:100, 10:100, 11:100, 12:100, 13:100, 14:100, 15:100, 16:100, 17:100, 18:100, or 19:100, but not limited to the above-mentioned values, and other values not listed in the above-mentioned value range are also applicable.
Preferably, the stirring rate in step (2) is 500-1000r/min, such as 550r/min, 600r/min, 650r/min, 700r/min, 750r/min, 800r/min, 850r/min, 900r/min or 950r/min, etc., but is not limited to the recited values, and other non-recited values in the range are also applicable.
Preferably, the ultrasonic dispersion time in step (2) is 30-90min, such as 40min, 50min, 60min, 70min or 80min, but not limited to the recited values, and other values not recited in the range of the values are also applicable.
As a preferred embodiment of the present invention, the temperature of the drying treatment in the step (2) is 80 to 120 ℃, for example, 85 ℃, 90 ℃, 95 ℃, 100 ℃, 105 ℃, 110 ℃ or 115 ℃, but not limited to the recited values, and other values not recited in the range of the values are also applicable.
Preferably, the drying time in step (2) is 6-10h, such as 6.5h, 7h, 7.5h, 8h, 8.5h, 9h or 9.5h, etc., but not limited to the recited values, and other values not recited in the range of the values are also applicable.
As a preferred embodiment of the present invention, the temperature of the calcination treatment in step (2) is 350-600 deg.C, such as 400 deg.C, 450 deg.C, 500 deg.C or 550 deg.C, but not limited to the values listed, and other values not listed in the range of the values are also applicable.
Preferably, the time of the roasting treatment in the step (2) is 3-8h, such as 3.5h, 4h, 4.5h, 5h, 5.5h, 6h, 6.5h, 7h or 7.5h, etc., but is not limited to the recited values, and other values not recited in the range of the values are also applicable.
As a preferable technical scheme of the invention, the reduction treatment method in the step (3) is to introduce H into a tube furnace 2 And (4) roasting the sample.
As a preferred embodiment of the present invention, the temperature of the reduction treatment in step (3) is 350-600 deg.C, such as 400 deg.C, 450 deg.C, 500 deg.C or 550 deg.C, but not limited to the values listed, and other values not listed in the range of the values are also applicable.
Preferably, the reduction of the treated H of step (3) 2 The flow rate is 30-150mL/min, such as 40mL/min, 50mL/min, 60mL/min, 70mL/min, 80mL/min, 90mL/min, 100mL/min, 110mL/min, 120mL/min, 130mL/min, 140mL/min, etc., and the mL/min, preferably the reduction treatment time of step (3), is 2-4h, such as 2.2h, 2.5h, 2.8h, 3h, 3.2h, 3.5h, or 3.8h, etc., but is not limited to the recited values, and other values not recited in the range of values are equally applicable.
In the invention, the Ni-HY molecular sieve prepared has Ni loading of 0-5 wt%, excluding 0, such as 0.5 wt%, 1 wt%, 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt%, 3.5 wt%, 4 wt% or 4.5 wt%, but is not limited to the recited values, and other values not recited in the numerical range are also applicable.
Compared with the prior art, the invention has at least the following beneficial effects:
the invention provides a catalytic synthesis method of pentanedicarbamic acid ester, the conversion rate of pentanediamine in the synthesis method reaches 100%, the yield of the pentanedicarbamic acid ester is more than 90%, the reaction condition is mild, the reaction time is short, no pollution is caused, the requirement on equipment is low, and the method is suitable for industrial production.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
This example provides a catalytic synthesis method of pentamethylene dicarbamate, including:
mixing diethyl carbonate, pentanediamine, a Ni-HY molecular sieve catalyst and ethanol, and then reacting to obtain the pentanedicarbamate;
the mole ratio of the pentamethylene diamine to the diethyl carbonate is 1:8, the mole ratio of the pentamethylene diamine to the ethanol is 1:45, and the mass ratio of the Ni-HY molecular sieve catalyst to the diamine is 0.2: 1;
the reaction temperature is 190 ℃, the pressure is 1.5MPa, and the heat preservation time is 5 h;
the preparation method of the Ni-HY molecular sieve catalyst comprises the following steps:
(1) stirring and mixing nickel nitrate hexahydrate and solvent water, wherein the mass ratio of soluble salt of nickel to water is 1:8 to obtain a mixed solution;
(2) adding an HY molecular sieve into the mixed solution obtained in the step (1) under stirring of 500rpm, wherein the mass ratio of soluble salt of nickel to the HY molecular sieve in the mixed solution is 1:40, performing ultrasonic dispersion for 30min, drying at 80 ℃ for 10h, and roasting at 350 ℃ for 8h to obtain a solid product;
(3) reducing the solid product obtained in the step (2) to obtain the Ni-HY molecular sieve;
the reduction treatment method comprises the step of introducing H into a tube furnace 2 Stream, H 2 The flow rate was 30mL/min and the samples were calcined at 350 ℃ for 4 h.
The Ni loading rate of the prepared Ni-HY molecular sieve catalyst is 0.5 wt%.
Example 2
This example provides a catalytic synthesis method of pentamethylene dicarbamate, including:
mixing diethyl carbonate, pentanediamine, an HY molecular sieve and methanol, and reacting to obtain the pentanedicarbamate;
the mole ratio of the pentamethylene diamine to the diethyl carbonate is 1:7, the mole ratio of the pentamethylene diamine to the methanol is 1:20, and the mass ratio of the HY molecular sieve catalyst to the pentamethylene diamine is 0.09: 1;
the reaction temperature is 175 ℃, the pressure is 2.0MPa, and the heat preservation time is 5 h;
the preparation method of the Ni-HY molecular sieve catalyst comprises the following steps:
(1) stirring and mixing nickel nitrate hexahydrate and solvent water, wherein the mass ratio of soluble salt of nickel to water is 1:10 to obtain a mixed solution;
(2) adding an HY molecular sieve into the mixed solution in the step (1) under stirring at 800rpm, wherein the mass ratio of soluble salt of nickel in the mixed solution to the HY molecular sieve is 10:65, ultrasonically dispersing for 60min, drying at 100 ℃ for 8h, and roasting at 500 ℃ for 5h to obtain a solid product;
(3) reducing the solid product obtained in the step (2) to obtain the Ni-HY molecular sieve catalyst;
the reduction treatment method comprises the step of introducing H into a tube furnace 2 Stream, H 2 The flow rate was 100mL/min, and the samples were calcined at 500 ℃ for 3 h.
The Ni loading rate of the prepared Ni-HY molecular sieve catalyst is 3 wt%.
Example 3
This example provides a catalytic synthesis method of pentamethylene dicarbamate, including:
mixing diethyl carbonate, pentanediamine, an HY molecular sieve catalyst and ethanol, and reacting to obtain the pentanedicarbamate;
the mole ratio of the pentamethylene diamine to the diethyl carbonate is 1:7, the mole ratio of the pentamethylene diamine to the ethanol is 1:20, and the mass ratio of the HY molecular sieve catalyst to the diamine is 0.05: 1;
the reaction temperature is 190 ℃, the pressure is 2.2MPa, and the heat preservation time is 5 h;
(1) stirring and mixing nickel sulfate hexahydrate and solvent water, wherein the mass ratio of soluble salt of nickel to water is 1:16 to obtain a mixed solution;
(2) adding an HY molecular sieve into the mixed solution in the step (1) under the stirring of 1000rpm, wherein the mass ratio of soluble salts of nickel to the HY molecular sieve in the mixed solution is 25:100, ultrasonically dispersing for 90min, drying at 120 ℃ for 6h, and roasting at 600 ℃ for 3h to obtain a solid product;
(3) reducing the solid product obtained in the step (2) to obtain the Ni-HY molecular sieve;
the reduction treatment method comprises the step of introducing H into a tube furnace 2 Stream, H 2 The flow rate was 150mL/min and the samples were calcined at 600 ℃ for 2 h.
The Ni loading rate of the prepared Ni-HY molecular sieve catalyst is 5 wt%.
Example 4
The conditions in this example were the same as those in example 3 except that the amount of the HY molecular sieve added was adjusted so that the loading rate of Ni in the prepared Ni-HY molecular sieve catalyst was 4 wt%.
Example 5
The conditions in this example were the same as those in example 3 except that the amount of the HY molecular sieve added was adjusted so that the loading rate of Ni in the prepared Ni-HY molecular sieve catalyst was 3 wt%.
Example 6
The conditions in this example were the same as those in example 3 except that the amount of the HY molecular sieve added was adjusted so that the loading rate of Ni in the prepared Ni-HY molecular sieve catalyst was 2 wt%.
Example 7
The conditions in this example were the same as those in example 3 except that the amount of the HY molecular sieve added was adjusted so that the loading rate of Ni in the prepared Ni-HY molecular sieve catalyst was 1 wt%.
Comparative example 1
This comparative example was conducted under the same conditions as in example 4 except that no Ni-HY molecular sieve catalyst was used.
Comparative example 2
This comparative example except that the Ni-HY molecular sieve catalyst was replaced with TiO 2 Otherwise, the other conditions were the same as in example 4.
Comparative example 3
The comparative example was carried out under the same conditions as in example 3 except that dimethyl carbonate was used instead of diethyl carbonate and methanol was used instead of ethanol.
The yield of pentamethylenedicarbamate and the conversion of pentamethylenediamine of examples 1 to 7 and comparative examples 1 to 3 were measured, and the results are shown in table 1.
TABLE 1
From the test results in table 1, it can be seen that the conversion rate of pentamethylene diamine can reach 100% and the yield of pentamethylene diamine can reach 94.2% in the catalytic synthesis method of pentamethylene diamine provided in examples 1-7 of the present invention. Comparative example 1 had a yield of pentamethylenedicarbamate of only 16.3% due to no catalyst added, while comparative example 2 had a yield of pentamethylenedicarbamate of only 61.0% using titanium dioxide as the catalyst. In comparative example 3, dimethyl carbonate was used as the carbonylating agent, and the yield thereof reached 81.3%, but there was a problem that DMC azeotroped with methanol and the subsequent separation was difficult.
The applicant states that the present invention is illustrated by the above examples to show the detailed process equipment and process flow of the present invention, but the present invention is not limited to the above detailed process equipment and process flow, i.e. it does not mean that the present invention must rely on the above detailed process equipment and process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A catalytic synthesis method of pentanedicarbamate is characterized by comprising the following steps:
diethyl carbonate, alcohol, pentanediamine and Ni-HY molecular sieve catalyst are mixed and stirred for reaction to obtain the pentanedicarbamate.
2. The catalytic synthesis method according to claim 1, wherein the mole ratio of the pentamethylene diamine and the diethyl carbonate is 1 (4-8);
preferably, the molar ratio of the pentamethylene diamine to the alcohol is 1 (15-45);
preferably, the mass ratio of the Ni-HY molecular sieve catalyst to diamine is (0.05-0.2): 1.
3. The synthesis method according to claim 1 or 2, wherein the reaction temperature is 160-200 ℃;
preferably, the reaction pressure is 1.5-2.2 MPa;
preferably, the reaction incubation time is 5-12 h.
4. The catalytic synthesis method according to any one of claims 1 to 3, wherein the Ni-HY catalyst is prepared by the following preparation method:
(1) stirring and mixing soluble salt of nickel and solvent water to obtain a mixed solution;
(2) adding an HY molecular sieve into the mixed solution in the step (1) under stirring, performing ultrasonic dispersion, and then sequentially performing drying and roasting treatment to obtain a solid product;
(3) and (3) carrying out reduction treatment on the solid product obtained in the step (2) to obtain the Ni-HY catalyst.
5. The preparation method according to claim 4, wherein the soluble salt of nickel in step (1) comprises any one or at least two of nickel nitrate, nickel chloride, nickel sulfate or nickel acetate;
preferably, the mass ratio of the soluble salt to the water is 1 (8-16).
6. The preparation method according to claim 4 or 5, wherein the mass ratio of the soluble salt of nickel to the HY molecular sieve in the mixed solution in the step (2) is 0-20: 100, excluding 0;
preferably, the stirring speed in the step (2) is 500-1000 r/min;
preferably, the time for ultrasonic dispersion in step (2) is 30-90 min.
7. The method according to any one of claims 4 to 6, wherein the temperature of the drying treatment in the step (2) is 80 to 120 ℃;
preferably, the drying treatment time in the step (2) is 6-10 h.
8. The method according to any one of claims 4 to 7, wherein the temperature of the roasting treatment in step (2) is 350-600 ℃;
preferably, the roasting treatment time in the step (2) is 3-8 h.
9. The production method according to any one of claims 4 to 8, wherein the reduction treatment in step (3) is performed by introducing H in a tube furnace 2 And (4) roasting the sample.
10. The method as claimed in claim 9, wherein the temperature of the reduction treatment in step (3) is 350-600 ℃;
preferably, the step of(3) The reduction-treated H 2 The flow rate is 30-150 mL/min;
preferably, the time of the reduction treatment in the step (3) is 2-4 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210791881.8A CN115010627B (en) | 2022-07-05 | 2022-07-05 | Catalytic synthesis method of glutarimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210791881.8A CN115010627B (en) | 2022-07-05 | 2022-07-05 | Catalytic synthesis method of glutarimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115010627A true CN115010627A (en) | 2022-09-06 |
| CN115010627B CN115010627B (en) | 2023-07-25 |
Family
ID=83079269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210791881.8A Active CN115010627B (en) | 2022-07-05 | 2022-07-05 | Catalytic synthesis method of glutarimide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115010627B (en) |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002212159A (en) * | 2001-01-18 | 2002-07-31 | National Institute Of Advanced Industrial & Technology | Method for producing carbamic acid ester |
| CN101792404A (en) * | 2010-03-22 | 2010-08-04 | 哈尔滨理工大学 | Method for synthesizing methyl N-phenyl carbamate via microwave assistance |
| CN101928238A (en) * | 2008-12-19 | 2010-12-29 | 中国科学院兰州化学物理研究所 | Method for catalytic synthesis of hexamethylene dicarbamate from hexamethylene diamine and small molecular alkyl carbamate |
| CN102782146A (en) * | 2010-03-01 | 2012-11-14 | 三井化学株式会社 | Method for producing 1,5-pentamethylene diamine, 1,5-pentamethylene diamine, 1,5-pentamethylene diisocyanate, method for producing 1,5-pentamethylene diisocyanate, polyisocyanate composition, and polyurethane resin |
| CN102964272A (en) * | 2012-11-09 | 2013-03-13 | 中国科学院过程工程研究所 | Method for preparing hexamethylene-1,6-diisocyanate (HDI) by heterocatalytic pyrolysis in liquid phase |
| CN105728033A (en) * | 2016-04-19 | 2016-07-06 | 安徽华荣高科新材料股份有限公司 | Application of catalyst for thermal decomposition of aliphatic or cycloaliphatic dicarbamate |
| EP3279185A1 (en) * | 2016-08-04 | 2018-02-07 | Taminco bvba | Improved process for the preparation of carbamates |
| CN113603613A (en) * | 2021-04-14 | 2021-11-05 | 中国科学院过程工程研究所 | Catalytic synthesis method of pentanedicarbamic acid ester |
| CN113731398A (en) * | 2020-05-27 | 2021-12-03 | 中国科学院过程工程研究所 | Catalyst for preparing dicarbamate and application thereof |
| JP2021191734A (en) * | 2020-06-05 | 2021-12-16 | 国立研究開発法人産業技術総合研究所 | Method for producing urea derivative |
| CN114105825A (en) * | 2020-08-27 | 2022-03-01 | 中国科学院过程工程研究所 | Preparation method of 1, 5-pentamethylene diisocyanate |
-
2022
- 2022-07-05 CN CN202210791881.8A patent/CN115010627B/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002212159A (en) * | 2001-01-18 | 2002-07-31 | National Institute Of Advanced Industrial & Technology | Method for producing carbamic acid ester |
| CN101928238A (en) * | 2008-12-19 | 2010-12-29 | 中国科学院兰州化学物理研究所 | Method for catalytic synthesis of hexamethylene dicarbamate from hexamethylene diamine and small molecular alkyl carbamate |
| CN102782146A (en) * | 2010-03-01 | 2012-11-14 | 三井化学株式会社 | Method for producing 1,5-pentamethylene diamine, 1,5-pentamethylene diamine, 1,5-pentamethylene diisocyanate, method for producing 1,5-pentamethylene diisocyanate, polyisocyanate composition, and polyurethane resin |
| CN101792404A (en) * | 2010-03-22 | 2010-08-04 | 哈尔滨理工大学 | Method for synthesizing methyl N-phenyl carbamate via microwave assistance |
| CN102964272A (en) * | 2012-11-09 | 2013-03-13 | 中国科学院过程工程研究所 | Method for preparing hexamethylene-1,6-diisocyanate (HDI) by heterocatalytic pyrolysis in liquid phase |
| CN105728033A (en) * | 2016-04-19 | 2016-07-06 | 安徽华荣高科新材料股份有限公司 | Application of catalyst for thermal decomposition of aliphatic or cycloaliphatic dicarbamate |
| EP3279185A1 (en) * | 2016-08-04 | 2018-02-07 | Taminco bvba | Improved process for the preparation of carbamates |
| CN113731398A (en) * | 2020-05-27 | 2021-12-03 | 中国科学院过程工程研究所 | Catalyst for preparing dicarbamate and application thereof |
| JP2021191734A (en) * | 2020-06-05 | 2021-12-16 | 国立研究開発法人産業技術総合研究所 | Method for producing urea derivative |
| CN114105825A (en) * | 2020-08-27 | 2022-03-01 | 中国科学院过程工程研究所 | Preparation method of 1, 5-pentamethylene diisocyanate |
| CN113603613A (en) * | 2021-04-14 | 2021-11-05 | 中国科学院过程工程研究所 | Catalytic synthesis method of pentanedicarbamic acid ester |
Non-Patent Citations (1)
| Title |
|---|
| 刘耀宗等: "1,5-戊二异氰酸酯合成研究进展", 《广东化工》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115010627B (en) | 2023-07-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2022041502A1 (en) | Preparation method for 1,5-pentane diisocyanate | |
| CN113603613B (en) | Catalytic synthesis method of pentanedicarbamic acid ester | |
| CN111423326B (en) | Method for preparing dimethyl carbonate by alkaline ionic liquid catalysis one-step method | |
| Wang et al. | Important Green Chemistry and Catalysis: Non‐phosgene Syntheses of Isocyanates–Thermal Cracking Way | |
| CN111389401B (en) | For the efficient catalytic conversion of CO2Preparation method of microorganism coupling catalytic system | |
| CN106279094B (en) | A kind of method of Thiourea preparing cyclic carbonate by catalyzing with ionic liquid | |
| CN114507161A (en) | Method for synthesizing isophorone diisocyanate | |
| CN106478586B (en) | Synthesis process of ethylene carbonate | |
| CN115010627A (en) | Catalytic synthesis method of pentamethyldicarbamate | |
| CN115073325B (en) | Synthetic method for preparing glutarimide by adopting dimethyl carbonate | |
| CN111393402B (en) | N & lt/EN & gt acid/quaternary ammonium salt composite catalytic CO 2 Method for preparing cyclic carbonate by cycloaddition with epoxide | |
| CN108117474B (en) | Method for preparing JP-10 aviation fuel from furfuryl alcohol | |
| JP5827756B2 (en) | Process for producing polymethylene polyphenyl polycarbamate | |
| CN114644576A (en) | 1, 3-cyclohexanedimethylene dicarbamate and preparation method and application thereof | |
| CN111234890B (en) | Synthesis method of aviation kerosene | |
| CN110172029B (en) | Method for continuously synthesizing 2-amino-2-methyl-1-propanol | |
| CN110683951A (en) | Method for directly preparing dimethyl carbonate by low-temperature high-efficiency catalysis of reaction of urea and methanol | |
| Cao et al. | Synthesis of dimethyl carbonate (dmc) from co 2, ethylene oxide and methanol using heterogeneous anion exchange resins as catalysts | |
| CN114989042B (en) | Catalytic synthesis method of glutarimide | |
| CN110961141B (en) | Vanadium-silicon molecular sieve, synthesis method and application thereof, and phenol oxidation method | |
| CN115055196A (en) | Heteropolyacid salt catalyst and preparation method and application thereof | |
| CN113289662B (en) | Catalyst for preparing cyclohexylamine by aniline hydrogenation, preparation method and application | |
| CN111848475B (en) | Preparation method of cyclohexyltriamine and preparation method of cyclohexyl triisocyanate | |
| CN116693425A (en) | Method for synthesizing glutarimide by one-step catalysis of pentanediamine and carbon dioxide | |
| CN102649758A (en) | Method for preparing ethylene carbonate by using CO gas phase method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |