CN101157617A - Method for synthesizing 1,2-propane diamine - Google Patents
Method for synthesizing 1,2-propane diamine Download PDFInfo
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- CN101157617A CN101157617A CNA2007101340918A CN200710134091A CN101157617A CN 101157617 A CN101157617 A CN 101157617A CN A2007101340918 A CNA2007101340918 A CN A2007101340918A CN 200710134091 A CN200710134091 A CN 200710134091A CN 101157617 A CN101157617 A CN 101157617A
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- propylene diamine
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Abstract
The invention relates to a synthetic method for 1, 2-propylene diamine which is produced by taking isopropyl alcohol as raw materials and filling catalyst for pressurizing and heating reaction under the hydrogen condition. The method comprises the steps as follows: firstly, isopropyl alcohol and catalyst are filled inside a reaction device; secondly, hydrogen is used for replacing the air inside the reaction device; thirdly, hydrogen and ammonia are continuously filled in for reaction under the temperature of 150 to 240 DEG C and the pressure of 10MPa to 13MPa, water is distilled through normal pressure after finishing the reaction, and then 1, 2-propylene diamine is obtained through vacuum distillation. The invention has the advantages that: (1) the technique process is clean with high product purity; (2) the cheap isopropyl alcohol is adopted as the raw materials, thereby decreasing the cost; (3) the whole compound process can be operated continuously, thereby increasing the use rate of the device, satisfying the industrial demand and further decreasing the production cost; (4) the invention can apply the catalyst mechanically.
Description
Technical field
The invention belongs to relate to a kind of 1, the synthetic method of 2-propylene diamine.
Background technology
Propylene diamine is as a kind of important meticulous organic chemical industry's intermediate, and its industrial application is extensive, and demand is big.Be widely used in medical fuel and organic synthesis.Propylene diamine is a low-grade aliphatic amine, and two isomerss are arranged, 1, and 2-propylene diamine and 1,3-propylene diamine.Propylene diamine is the same with other lipid acid to be polar compound, can form hydrogen bond, and not share electron pair is arranged on the nitrogen-atoms because this has nucleophilicity to share electron pair not, easily and some Electron Affinities compounds react.As it is that a kind of organic bases can generate corresponding inorganic salt, organic salt with mineral acid, organic acid effect; With alkylating reagent effects such as halohydrocarbon, alcohol; With organic acid, acyl chlorides, ester and acid anhydrides generation acylation; Generate unsettled Schiff alkali with the carbonyl compound reaction, Schiff alkali hydrogenating reduction can be produced the propylene diamine that alkyl replaces; Can also and unsaturated compound, effects such as prussiate, nitrile, sulfide, epoxy compounds phosphide.
The propylene diamine purposes is very extensive; can be used for dressing agent, metal passivator, bio protective agent, oil fuel and lubricating oil additive, be used for dyestuff, plating and analytical reagent (calibrating of mercury, copper and silver), also can be used as aviation with resin curing agent, thiofide and beneficiation reagent etc.
Propylene diamine is important organic synthesis raw material, is widely used in medicine, agricultural chemicals, dyestuff, petroleum refining industry's additive and polymkeric substance.For example, 1, the 2-propylene diamine can be as the solvent of digestion fiber, coating, vegetables oil and rosin etc., the manufacturing raw material of medicine, gasoline dope etc.By 1, the 2-propylene diamine synthesizes 1 in the medicine industry, and the 2-trimethylenedinitrilo-tertraacetic acid is the intermediate of anticarcinogen tetrahydroform.By 1,2-propylene diamine synthetic 2-methyl-4-rubigan imidazoles is good copper product corrosion inhibitor in addition.By 1,3-propylene diamine synthetic 1-amino-3-methylamino-propane and 1-amino-3-dimethylamino-propane are the components of Resins, epoxy.By 1, the compound that 3-propylene diamine synthetic contains triazine is a kind of chemically-reactive dyes.Propylene diamine can also Synthetic 2, and 3, the 5-trimethylpyrazine is one of most widely used general, kind that consumption is maximum in the pyrazine class spices; Corresponding chirality propylene diamine can synthesizing antitumor medicine dexrazoxane (claiming dexrazoxane again).
Along with society and development of science and technology, propylene diamine especially 1, the range of application of 2-propylene diamine is in continuous expansion, the document that is used for organic synthesis, dyestuff, petroleum refining industry's additive and polymkeric substance is a lot, be a kind of organic chemical industry with broad prospects for development and fine chemicals, therefore cause people's attention day by day.According to the knowledge of the applicant, present 1, the chemical synthesis process of 2-propylene diamine mainly is to be raw material with haloalkane (1, the 2-propylene dichloride), through amination production.This reaction is still formula intermittent reaction, and equipment corrosion is more serious, and the three wastes are many, and raw material consumption is big.
Summary of the invention
The technical problem to be solved in the present invention is existing exactly to be that raw material is synthetic 1 with the haloalkane, and the existing equipment corrosion of the method for 2-propylene diamine is serious, and the three wastes are many, and the shortcoming that raw material consumption is big provides a kind of synthetic method of the propylene diamine with industrial value of cleaning.
For solving the problems of the technologies described above, the present invention adopts following technical scheme
With the Yi Bingchunan is raw material, adds catalyzer and pressurize and reacting by heating generation 1 under the hydrogen condition, and the 2-propylene diamine specifically comprises the steps:
The first step adds Yi Bingchunan and catalyzer in the reactor;
Second step is with the air in the hydrogen exchange reactor;
The 3rd step continue to feed hydrogen and ammonia, reacted 10h～15h under 150 ℃～240 ℃, the condition of 10MPa～13Mpa;
In the 4th step, after reaction finished, air distillation removed and anhydrates, and vacuum distilling obtains 1 then, the pure product of 2-propylene diamine.
Separate out target product 1, the structural formula of 2-propylene diamine is as follows:
In the first step, entry can be added as solvent, and the 2-5% emulsifying agent of Yi Bingchunan quality can be added, to increase the contact area of Yi Bingchunan and ammonia, aforementioned emulsifying agent is selected from Yelkin TTS, sodium stearate or oleic acid.
In the first step, catalyst consumption is 3%～10% of a Yi Bingchunan quality, and aforementioned catalyzer is the metal catalyst that has load, is selected from metal catalysts such as Ni, Pa, Ru or Co.
In the 3rd step, the ratio of the amount of substance of Yi Bingchunan and ammonia is 1-1.5.
The present invention compared with prior art has following advantage: (1) synthesis process cleaning, product purity height; (2) adopting cheap Yi Bingchunan is raw material, has reduced cost; (3) entire synthesis process can realize operate continuously, has improved the rate of utilization of equipment, satisfies industrialized needs, makes production cost further reduce; (4) can realize applying mechanically of catalyzer.
Embodiment
The invention will be further described below in conjunction with embodiment.
Embodiment 1: the preparation of propylene diamine.
With the 10mol Yi Bingchunan, 22.5gRaney Ni catalyzer joins in the reactor, and with the air in the hydrogen exchange reactor, 12mol anhydrous ammonia, logical a little hydrogen is warming up to 150 ℃, continues to feed hydrogen to 10MPa, keep-ups pressure at 10MPa reaction 10h.Reaction finishes the postcooling reaction solution, and first normal pressure steams moisture, and vacuum distilling gets the pure product 6.8mol of propylene diamine then.
Embodiment 2: the preparation of propylene diamine.
With the 10mol Yi Bingchunan, 22.5g Pd/C catalyzer joins in the reactor, and with the air in the hydrogen exchange reactor, 12mol anhydrous ammonia, logical a little hydrogen is warming up to 150 ℃, continues to feed hydrogen to 10MPa, keep-ups pressure at 10MPa reaction 10h.Reaction finishes the postcooling reaction solution, and first normal pressure steams moisture, and vacuum distilling gets the pure product 6.6mol of propylene diamine then.
Embodiment 3: the preparation of propylene diamine.
With the 10mol Yi Bingchunan, 22.5gRaney Ni catalyzer and 0.5mol water join in the reactor, with the air in the hydrogen exchange reactor, the 13mol anhydrous ammonia, logical a little hydrogen is warming up to 180 ℃, continue to feed hydrogen to 11MPa, keep-up pressure, reaction 12h at 11MPa.Reaction finishes the postcooling reaction solution, and first normal pressure steams moisture, and vacuum distilling gets the pure product 6.4mol of propylene diamine then.
Embodiment 4: the preparation of propylene diamine.
With the 10mol Yi Bingchunan, 25gRaney Ni catalyzer joins in the reactor, and with the air in the hydrogen exchange reactor, 13mol anhydrous ammonia, logical a little hydrogen is warming up to 200 ℃, continues to feed hydrogen to 12MPa, keep-ups pressure at 12MPa reaction 10h.Reaction finishes the postcooling reaction solution, and first normal pressure steams moisture, and vacuum distilling gets the pure product 7.1mol of propylene diamine then.
Embodiment 5: the preparation of propylene diamine.
With the 10mol Yi Bingchunan, 25gRaney Ni catalyzer, 15g oleic acid join in the reactor, with the air in the hydrogen exchange reactor, the 15mol anhydrous ammonia, logical a little hydrogen is warming up to 240 ℃, continue to feed hydrogen to 12MPa, keep-up pressure, reaction 15h at 12MPa.Reaction finishes the postcooling reaction solution, and first normal pressure steams moisture, and vacuum distilling gets the pure product 7.2mol of propylene diamine then.
Claims (9)
1. one kind 1, the synthetic method of 2-propylene diamine is characterized in that with the Yi Bingchunan being raw material, adds catalyzer and pressurize and reacting by heating generation 1 under the hydrogen condition, and the 2-propylene diamine specifically comprises the steps:
The first step adds Yi Bingchunan and catalyzer in the reactor;
Second step is with the air in the hydrogen exchange reactor;
The 3rd step continue to feed hydrogen and ammonia, reacted under 150 ℃～240 ℃, the condition of 10MPa～13Mpa;
In the 4th step, after reaction finished, air distillation removed and anhydrates, and vacuum distilling obtains 1 then, the pure product of 2-propylene diamine.
2. according to claim 11, the synthetic method of 2-propylene diamine is characterized in that: add entry as solvent in the first step.
3. according to claim 11, the synthetic method of 2-propylene diamine is characterized in that: catalyst consumption is 3%～10% of a Yi Bingchunan quality in the first step.
4. according to claim 1 or 3 described 1, the synthetic method of 2-propylene diamine is characterized in that: the catalyzer in the first step is the metal catalyst that has load.
5. according to claim 41, the synthetic method of 2-propylene diamine is characterized in that described metal catalyst is selected from Ni, Pa, Ru or Co metal catalyst.
6. according to claim 11, the synthetic method of 2-propylene diamine is characterized in that: add the 2-5% emulsifying agent of Yi Bingchunan quality in the first step, to increase the contact area of Yi Bingchunan and ammonia.
7. according to claim 61, the synthetic method of 2-propylene diamine is characterized in that: described emulsifying agent is selected from Yelkin TTS, sodium stearate or oleic acid.
8. according to claim 11, the synthetic method of 2-propylene diamine is characterized in that: the ratio of the amount of substance of Yi Bingchunan and ammonia is 1-1.5.
9. according to claim 11, the synthetic method of 2-propylene diamine is characterized in that: the reaction times in the 3rd step is 10h～15h;
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CNA2007101340918A CN101157617A (en) | 2007-10-19 | 2007-10-19 | Method for synthesizing 1,2-propane diamine |
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2007101340918A CN101157617A (en) | 2007-10-19 | 2007-10-19 | Method for synthesizing 1,2-propane diamine |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101891628A (en) * | 2010-07-19 | 2010-11-24 | 张家港市大伟助剂有限公司 | Preparation method of 1,2-propane diamine |
| CN102557961A (en) * | 2011-12-29 | 2012-07-11 | 南通天泽化工有限公司 | Process for producing 1,2-propanediamine |
| CN103626664A (en) * | 2013-11-01 | 2014-03-12 | 西安近代化学研究所 | Method for synthesizing 2-methyl-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 |
| CN103664635A (en) * | 2012-09-06 | 2014-03-26 | 济南大学 | Method for preparing 1,2-propane diamine through phase-transfer catalysis |
| CN103819344A (en) * | 2013-12-18 | 2014-05-28 | 西安近代化学研究所 | Synthesis method of 1,2-propane diamine |
| CN110327931A (en) * | 2019-07-26 | 2019-10-15 | 山东达民化工股份有限公司 | The trimethylene amine production technology of catalyst and preparation method thereof and application catalyst |
| CN111433183A (en) * | 2017-11-30 | 2020-07-17 | 巴斯夫欧洲公司 | Process for the continuous preparation of 1, 2-propanediamine (1,2-PDA) and dimethyldiethylenetriamine (DMDETA) |
-
2007
- 2007-10-19 CN CNA2007101340918A patent/CN101157617A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101891628B (en) * | 2010-07-19 | 2013-02-27 | 张家港市大伟助剂有限公司 | Preparation method of 1,2-propane diamine |
| CN101891628A (en) * | 2010-07-19 | 2010-11-24 | 张家港市大伟助剂有限公司 | Preparation method of 1,2-propane diamine |
| CN102557961A (en) * | 2011-12-29 | 2012-07-11 | 南通天泽化工有限公司 | Process for producing 1,2-propanediamine |
| CN103664634B (en) * | 2012-09-06 | 2017-06-16 | 济南大学 | For loaded catalyst prepared by 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 |
| CN103664635A (en) * | 2012-09-06 | 2014-03-26 | 济南大学 | Method for preparing 1,2-propane diamine through phase-transfer catalysis |
| CN103664635B (en) * | 2012-09-06 | 2017-06-16 | 济南大学 | A kind of method that phase transfer catalysis (PTC) prepares 1,2 propane diamine |
| CN103626664A (en) * | 2013-11-01 | 2014-03-12 | 西安近代化学研究所 | Method for synthesizing 2-methyl-1,2-propane diamine |
| CN103819344B (en) * | 2013-12-18 | 2016-04-27 | 西安近代化学研究所 | A kind of synthetic method of 1,2-propylene diamine |
| CN103819344A (en) * | 2013-12-18 | 2014-05-28 | 西安近代化学研究所 | Synthesis method of 1,2-propane diamine |
| CN111433183A (en) * | 2017-11-30 | 2020-07-17 | 巴斯夫欧洲公司 | Process for the continuous preparation of 1, 2-propanediamine (1,2-PDA) and dimethyldiethylenetriamine (DMDETA) |
| CN111433183B (en) * | 2017-11-30 | 2023-12-22 | 巴斯夫欧洲公司 | Method for continuously preparing 1, 2-propylene diamine and dimethyl diethylenetriamine |
| CN110327931A (en) * | 2019-07-26 | 2019-10-15 | 山东达民化工股份有限公司 | The trimethylene amine production technology of catalyst and preparation method thereof and application catalyst |
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Owner name: NANJING BAOCHUN CHEMICAL INDUSTRY CO., LTD. Free format text: FORMER OWNER: HONGBAOLI CO. LTD., NANJING Effective date: 20091218 |
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Effective date of registration: 20091218 Address after: 1-C18-1, No. 210047, Nanjing chemical industry park, Jiangsu, Nanjing Applicant after: Nanjing Baochun Chemical Co., Ltd. Address before: Gaochun County, Nanjing City, Jiangsu Province, Taian Road No. 128 post encoding: 211300 Applicant before: Hongbaoli Co., Ltd., Nanjing |
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Open date: 20080409 |