CN113105336A - Preparation method of 1, 2-propane diamine - Google Patents
Preparation method of 1, 2-propane diamine Download PDFInfo
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- CN113105336A CN113105336A CN202110404866.9A CN202110404866A CN113105336A CN 113105336 A CN113105336 A CN 113105336A CN 202110404866 A CN202110404866 A CN 202110404866A CN 113105336 A CN113105336 A CN 113105336A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/888—Tungsten
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
Abstract
The invention relates to the technical field of preparation of propane diamine, and discloses a preparation method of 1, 2-propane diamine, which comprises the following raw materials in parts by weight: 10-15 parts of 1, 2-dichloropropane, 3-6 parts of catalyst, 17-20 parts of solvent water, 5-9 parts of liquid ammonia, 3-6 parts of sodium hydroxide and 2-5 parts of auxiliary agent. According to the preparation method of the 1, 2-propane diamine, the carrier of the selected catalyst for preparing the propane diamine is Al2O3, crystalline aluminosilicate or a mixture thereof, the powdery catalyst is prepared by a precipitation method, drying, roasting and reduction, and in the preparation process of the 1, 2-propane diamine, the catalyst generates less impurity waste liquid, so that the phenomenon that a finished product of the 1, 2-propane diamine contains a large amount of impurities after preparation is completed is avoided, the preparation efficiency of the 1, 2-propane diamine and the quality of the finished product are further improved, and the neutralization efficiency can be improved by adding sodium hydroxide in the preparation process of the 1, 2-propane diamine.
Description
Technical Field
The invention relates to the technical field of preparation of propane diamine, and particularly relates to a preparation method of 1, 2-propane diamine.
Background
1, 2-propane Diamine (DAP) is an important fine chemical intermediate and has wide application in the fields of organic synthesis, medicines, dyes, pesticides, chemical auxiliaries, rubber plastic auxiliaries, epoxy resin curing agents and the like. The catalyst is used for organic synthesis, pharmacy and synthetic dyes, is used as a cellosolve, a rubber vulcanization accelerator and the like, is commonly used for producing mineral dressing reagents, metal passivators, boat air resin curing agents and rubber vulcanization accelerators, and is also used for dyes, electroplating and analytical reagents (mercury, copper and silver detection). The product is used in medicine industry to produce 1, 2-propane diamine tetraacetic acid as intermediate of anticancer drug propane imine. Meanwhile, the product is used as a manufacturing raw material in the aspects of aviation resin curing agent, rubber vulcanization accelerator, mineral dressing agent, metal passivator, dye, electroplating and the like, and is also used as an analysis reagent. Used as solvents for cellulose nitrate, paints, vegetable oils, rosin, and the like.
In the existing production and preparation process of 1, 2-propane diamine, the selected catalyst is easy to cause excessive impurities in the finished product of 1, 2-propane diamine, so that the impurity removal time in the later period is too long, and the production and preparation efficiency of 1, 2-propane diamine is influenced.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides the preparation method of the 1, 2-propane diamine, which has the advantages of less impurities of the 1, 2-propane diamine in a finished product and the like, and solves the problem of overlong impurity removal time in the later period.
(II) technical scheme
In order to achieve the purpose, the invention provides the following technical scheme: a preparation method of 1, 2-propane diamine comprises the following raw materials in parts by weight: 10-15 parts of 1, 2-dichloropropane, 3-6 parts of catalyst, 17-20 parts of solvent water, 5-9 parts of liquid ammonia, 3-6 parts of sodium hydroxide and 2-5 parts of auxiliary agent.
The preparation method of the 1, 2-propane diamine comprises the following steps:
s1, weighing the raw materials for later use
Raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia, sodium hydroxide and an auxiliary agent which are required to be prepared for preparing the 1, 2-propane diamine are weighed by corresponding weighing equipment, and the weighed raw materials are respectively placed into related storage containers for storage and standby.
S2, high-pressure mixing reaction
Weighing 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia and an auxiliary agent which are used for later use, adding the weighed raw materials into a high-pressure reaction kettle, introducing hydrogen into the high-pressure reaction kettle to replace and discharge air in the reaction kettle, starting the high-pressure reaction kettle after the completion of the reaction, heating and pressurizing the high-pressure reaction kettle, mixing and stirring the mixed solution, and cooling the high-pressure reaction kettle to normal temperature after the mixing and stirring.
S3, neutralization of solution
And adding the sodium hydroxide weighed in the first step into the cooled high-pressure reaction kettle, and neutralizing the mixed solution in the high-pressure reaction kettle to make the mixed solution alkaline.
S4, filtering and concentrating
And filtering and removing reactants generated by the catalyst in the obtained reaction liquid by corresponding filtering equipment, and concentrating the reaction liquid by concentrating equipment.
S5 desalting and rectifying
And (3) desalting the concentrated reaction solution, heating and rectifying the reaction solution by using a distillation device after the desalting is finished, and distilling and dehydrating the water to obtain the finished product of the 1, 2-propane diamine.
Preferably, the catalyst carrier is Al2O3, crystalline aluminosilicate or a mixture thereof, wherein the active component is CuO, WO3 and Sb2O3, and the powdery catalyst is prepared by a precipitation method, drying, roasting and reducing.
Preferably, the auxiliary agent is one or a combination of two or more of hydroxides of alkali metals, hydroxides of alkaline earth metals, carbonates of alkali metals and carbonates of alkaline earth metals.
Preferably, in the step S2, the heating temperature of the high-pressure reaction kettle is 150 to 180 ℃, and the pressurizing value range is 3 to 5 MPa.
Preferably, the stirring reaction time of the high-pressure reaction kettle in the step S2 is 3-5 hours.
Preferably, the stirring neutralization time of the reaction solution in the high-pressure reaction kettle in the step S3 is 40-60 minutes.
Preferably, the concentration time of the reaction solution by the concentration device in the step S4 is 30-50 minutes.
Preferably, in the step S5, the distillation temperature is 120-150 ℃, and the distillation time is 2-3 hours.
(III) advantageous effects
Compared with the prior art, the invention provides a preparation method of 1, 2-propane diamine, which has the following beneficial effects:
the preparation method of the 1, 2-propane diamine is characterized in that the carrier of the selected catalyst for preparing the propane diamine is Al2O3, crystalline aluminosilicate or a mixture thereof, wherein the active components are WO3 and Sb2O3, and the powdery catalyst is prepared by a precipitation method, drying, roasting and reduction, in the process of preparing the 1, 2-propane diamine, the catalyst generates less impurity waste liquid, so that the impurity content in the finished product of the 1, 2-propane diamine is lower, the phenomenon that the finished product of the 1, 2-propane diamine contains a large amount of impurities after the preparation is finished is avoided, the time for screening and removing the impurities of the finished product of the 1, 2-propane diamine is shortened, the preparation efficiency of the 1, 2-propane diamine and the quality of the finished product are further improved, and the neutralization efficiency can be improved by adding sodium hydroxide in the process of preparing the 1, 2-propane diamine.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
a preparation method of 1, 2-propane diamine comprises the following raw materials in parts by weight: 10 parts of 1, 2-dichloropropane, 3 parts of catalyst, 17 parts of solvent water, 5 parts of liquid ammonia, 3 parts of sodium hydroxide and 2 parts of auxiliary agent.
The preparation method of the 1, 2-propane diamine comprises the following steps:
s1, weighing the raw materials for later use
Raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia, sodium hydroxide and an auxiliary agent which are required to be prepared for preparing the 1, 2-propane diamine are weighed by corresponding weighing equipment, and the weighed raw materials are respectively placed into related storage containers for storage and standby.
S2, high-pressure mixing reaction
Adding the weighed and standby raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia and an auxiliary agent into a high-pressure reaction kettle, introducing hydrogen into the high-pressure reaction kettle to replace and discharge air in the reaction kettle, starting the high-pressure reaction kettle after the completion of the reaction, heating and pressurizing the high-pressure reaction kettle, mixing and stirring the mixed solution, cooling the high-pressure reaction kettle to normal temperature after the mixing and stirring are carried out, wherein the heating temperature of the high-pressure reaction kettle is 150-180 ℃, the pressurizing numerical range is 3-5 MPa, and the stirring reaction time is 3-5 hours.
S3, neutralization of solution
And adding the sodium hydroxide weighed in the first step into the cooled high-pressure reaction kettle, and neutralizing the mixed solution in the high-pressure reaction kettle to be alkaline, wherein the stirring neutralization time of the reaction liquid in the high-pressure reaction kettle is 40-60 minutes.
S4, filtering and concentrating
And filtering the obtained reaction liquid by corresponding filtering equipment to remove reactants generated by the catalyst in the reaction liquid, and concentrating the reaction liquid by concentrating equipment, wherein the concentrating time of the concentrating equipment on the reaction liquid is 30-50 minutes.
S5 desalting and rectifying
And (3) desalting the concentrated reaction solution, heating and rectifying the reaction solution by using a distillation device after the desalting is finished, and distilling and drying the water to obtain the finished product of the 1, 2-propane diamine, wherein the distillation temperature is 120-150 ℃, and the distillation time is 2-3 hours.
The catalyst carrier is Al2O3, crystalline aluminosilicate or a mixture thereof, wherein the active component is CuO, WO3 and Sb2O3, and the powdery catalyst is prepared by a precipitation method, drying, roasting and reducing.
The auxiliary agent is one or a composition of more than two of alkali metal hydroxide, alkaline earth metal hydroxide, alkali metal carbonate and alkaline earth metal carbonate.
Example two:
a preparation method of 1, 2-propane diamine comprises the following raw materials in parts by weight: 13 parts of 1, 2-dichloropropane, 5 parts of catalyst, 18 parts of solvent water, 7 parts of liquid ammonia, 4 parts of sodium hydroxide and 3 parts of auxiliary agent.
The preparation method of the 1, 2-propane diamine comprises the following steps:
s1, weighing the raw materials for later use
Raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia, sodium hydroxide and an auxiliary agent which are required to be prepared for preparing the 1, 2-propane diamine are weighed by corresponding weighing equipment, and the weighed raw materials are respectively placed into related storage containers for storage and standby.
S2, high-pressure mixing reaction
Adding the weighed and standby raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia and an auxiliary agent into a high-pressure reaction kettle, introducing hydrogen into the high-pressure reaction kettle to replace and discharge air in the reaction kettle, starting the high-pressure reaction kettle after the completion of the reaction, heating and pressurizing the high-pressure reaction kettle, mixing and stirring the mixed solution, cooling the high-pressure reaction kettle to normal temperature after the mixing and stirring are carried out, wherein the heating temperature of the high-pressure reaction kettle is 150-180 ℃, the pressurizing numerical range is 3-5 MPa, and the stirring reaction time is 3-5 hours.
S3, neutralization of solution
And adding the sodium hydroxide weighed in the first step into the cooled high-pressure reaction kettle, and neutralizing the mixed solution in the high-pressure reaction kettle to be alkaline, wherein the stirring neutralization time of the reaction liquid in the high-pressure reaction kettle is 40-60 minutes.
S4, filtering and concentrating
And filtering the obtained reaction liquid by corresponding filtering equipment to remove reactants generated by the catalyst in the reaction liquid, and concentrating the reaction liquid by concentrating equipment, wherein the concentrating time of the concentrating equipment on the reaction liquid is 30-50 minutes.
S5 desalting and rectifying
And (3) desalting the concentrated reaction solution, heating and rectifying the reaction solution by using a distillation device after the desalting is finished, and distilling and drying the water to obtain the finished product of the 1, 2-propane diamine, wherein the distillation temperature is 120-150 ℃, and the distillation time is 2-3 hours.
The catalyst carrier is Al2O3, crystalline aluminosilicate or a mixture thereof, wherein the active component is CuO, WO3 and Sb2O3, and the powdery catalyst is prepared by a precipitation method, drying, roasting and reducing.
The auxiliary agent is one or a composition of more than two of alkali metal hydroxide, alkaline earth metal hydroxide, alkali metal carbonate and alkaline earth metal carbonate.
Example three:
a preparation method of 1, 2-propane diamine comprises the following raw materials in parts by weight: 15 parts of 1, 2-dichloropropane, 6 parts of catalyst, 20 parts of solvent water, 9 parts of liquid ammonia, 6 parts of sodium hydroxide and 5 parts of auxiliary agent.
The preparation method of the 1, 2-propane diamine comprises the following steps:
s1, weighing the raw materials for later use
Raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia, sodium hydroxide and an auxiliary agent which are required to be prepared for preparing the 1, 2-propane diamine are weighed by corresponding weighing equipment, and the weighed raw materials are respectively placed into related storage containers for storage and standby.
S2, high-pressure mixing reaction
Adding the weighed and standby raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia and an auxiliary agent into a high-pressure reaction kettle, introducing hydrogen into the high-pressure reaction kettle to replace and discharge air in the reaction kettle, starting the high-pressure reaction kettle after the completion of the reaction, heating and pressurizing the high-pressure reaction kettle, mixing and stirring the mixed solution, cooling the high-pressure reaction kettle to normal temperature after the mixing and stirring are carried out, wherein the heating temperature of the high-pressure reaction kettle is 150-180 ℃, the pressurizing numerical range is 3-5 MPa, and the stirring reaction time is 3-5 hours.
S3, neutralization of solution
And adding the sodium hydroxide weighed in the first step into the cooled high-pressure reaction kettle, and neutralizing the mixed solution in the high-pressure reaction kettle to be alkaline, wherein the stirring neutralization time of the reaction liquid in the high-pressure reaction kettle is 40-60 minutes.
S4, filtering and concentrating
And filtering the obtained reaction liquid by corresponding filtering equipment to remove reactants generated by the catalyst in the reaction liquid, and concentrating the reaction liquid by concentrating equipment, wherein the concentrating time of the concentrating equipment on the reaction liquid is 30-50 minutes.
S5 desalting and rectifying
And (3) desalting the concentrated reaction solution, heating and rectifying the reaction solution by using a distillation device after the desalting is finished, and distilling and drying the water to obtain the finished product of the 1, 2-propane diamine, wherein the distillation temperature is 120-150 ℃, and the distillation time is 2-3 hours.
The catalyst carrier is Al2O3, crystalline aluminosilicate or a mixture thereof, wherein the active component is CuO, WO3 and Sb2O3, and the powdery catalyst is prepared by a precipitation method, drying, roasting and reducing.
The auxiliary agent is one or a composition of more than two of alkali metal hydroxide, alkaline earth metal hydroxide, alkali metal carbonate and alkaline earth metal carbonate.
The invention has the beneficial effects that: the catalyst is prepared from a powdery catalyst by a precipitation method, drying, roasting and reducing, wherein the active components are WO3 and Sb2O3, and the powdery catalyst is prepared by drying, roasting and reducing the catalyst by a precipitation method, so that impurity waste liquid generated by the catalyst is less in the preparation process of the 1, 2-propane diamine, the impurity content of the finished product 1, 2-propane diamine is lower, the phenomenon that the finished product 1, 2-propane diamine contains a large amount of impurities after preparation is avoided, the time for screening and removing the impurities of the finished product 1, 2-propane diamine is shortened, the preparation efficiency of the 1, 2-propane diamine and the quality of the finished product are further improved, and the neutralization efficiency can be improved by adding sodium hydroxide in the preparation process of the 1, 2-propane diamine.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (8)
1. The preparation method of the 1, 2-propane diamine is characterized by comprising the following raw materials in parts by weight: 10-15 parts of 1, 2-dichloropropane, 3-6 parts of catalyst, 17-20 parts of solvent water, 5-9 parts of liquid ammonia, 3-6 parts of sodium hydroxide and 2-5 parts of auxiliary agent;
the preparation method of the 1, 2-propane diamine comprises the following steps:
s1, weighing the raw materials for later use
Raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia, sodium hydroxide and an auxiliary agent which are required to be prepared for preparing the 1, 2-propane diamine are weighed by corresponding weighing equipment, and the weighed raw materials are respectively placed into related storage containers for storage and standby application;
s2, high-pressure mixing reaction
Adding the weighed and standby raw materials 1, 2-dichloropropane, a catalyst, solvent water, liquid ammonia and an auxiliary agent into a high-pressure reaction kettle, introducing hydrogen into the high-pressure reaction kettle to replace and discharge air in the reaction kettle, starting the high-pressure reaction kettle after the completion of the reaction, heating and pressurizing the high-pressure reaction kettle, mixing and stirring the mixed solution, and cooling the high-pressure reaction kettle to normal temperature after the mixing and stirring;
s3, neutralization of solution
Adding the sodium hydroxide weighed in the first step into the cooled high-pressure reaction kettle, and neutralizing the mixed solution in the high-pressure reaction kettle to make the mixed solution alkaline;
s4, filtering and concentrating
Filtering and removing reactants generated by a catalyst in the obtained reaction liquid through corresponding filtering equipment, and concentrating the reaction liquid through concentrating equipment;
s5 desalting and rectifying
And (3) desalting the concentrated reaction solution, heating and rectifying the reaction solution by using a distillation device after the desalting is finished, and distilling and dehydrating the water to obtain the finished product of the 1, 2-propane diamine.
2. The method of claim 1, 2-propanediamine of claim 1, wherein said catalyst support is Al2O3, crystalline aluminosilicate or mixtures thereof, wherein the active component is CuO, WO3, Sb2O3, and the catalyst is prepared by precipitation, drying, calcining, and reducing to obtain a powdered catalyst.
3. The method of claim 1, 2-propanediamine according to claim 1, characterized in that said auxiliary agent is one or a combination of two or more of an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal carbonate and an alkaline earth metal carbonate.
4. The method of claim 1, 2-propanediamine, according to claim 1, characterized in that, in said step S2, the heating temperature of its autoclave is 150-180 ℃ and its pressurization value is in the range of 3-5 MPa.
5. The method according to claim 1, wherein the reaction time of the autoclave in step S2 is 3-5 hours.
6. The method according to claim 1, wherein the reaction solution in the autoclave of step S3 is stirred for 40 to 60 minutes.
7. The method according to claim 1, wherein the concentration time of the reaction solution by the concentration device in step S4 is 30-50 minutes.
8. The method for preparing 1, 2-propanediamine according to claim 1, characterized in that, in said step S5, the distillation temperature is 120-150 ℃ and the distillation time is 2-3 hours.
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| CN202110404866.9A CN113105336A (en) | 2021-04-15 | 2021-04-15 | Preparation method of 1, 2-propane diamine |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012158A (en) * | 2012-11-28 | 2013-04-03 | 张家港市大伟助剂有限公司 | Preparation method of 1,2-propane diamine |
| CN103664634A (en) * | 2012-09-06 | 2014-03-26 | 济南大学 | Supported catalyst for preparation of 1, 2-propane diamine |
| CN112121812A (en) * | 2020-09-16 | 2020-12-25 | 万华化学集团股份有限公司 | Catalyst for preparing propane diamine, preparation method of catalyst and method for preparing propane diamine |
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2021
- 2021-04-15 CN CN202110404866.9A patent/CN113105336A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103664634A (en) * | 2012-09-06 | 2014-03-26 | 济南大学 | Supported catalyst for preparation of 1, 2-propane diamine |
| CN103012158A (en) * | 2012-11-28 | 2013-04-03 | 张家港市大伟助剂有限公司 | Preparation method of 1,2-propane diamine |
| CN112121812A (en) * | 2020-09-16 | 2020-12-25 | 万华化学集团股份有限公司 | Catalyst for preparing propane diamine, preparation method of catalyst and method for preparing propane diamine |
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Application publication date: 20210713 |