CN103664636A - Method for synthesizing 1,2-propane diamine - Google Patents
Method for synthesizing 1,2-propane diamine Download PDFInfo
- Publication number
- CN103664636A CN103664636A CN201310569859.XA CN201310569859A CN103664636A CN 103664636 A CN103664636 A CN 103664636A CN 201310569859 A CN201310569859 A CN 201310569859A CN 103664636 A CN103664636 A CN 103664636A
- Authority
- CN
- China
- Prior art keywords
- propylene
- propylene diamine
- synthetic method
- propylene dichloride
- dichloride
- 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.)
- Pending
Links
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract 5
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 31
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 238000010189 synthetic method Methods 0.000 claims description 8
- 239000003125 aqueous solvent Substances 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract 1
- 238000007599 discharging Methods 0.000 abstract 1
- 239000003344 environmental pollutant Substances 0.000 abstract 1
- 231100000719 pollutant Toxicity 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003295 industrial effluent Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 1,2-propane diamine. The method takes 1,2-propylene dichloride as a raw material and specifically comprises the following steps: (1) feeding a catalyst, a solvent water and 1,2-propylene dichloride into a high-pressure reaction kettle, and closing the high-pressure kettle; (2) introducing liquid ammonia into the reaction kettle; and (3) rapidly raising the temperature to be 160-180 DEG C, keeping the temperature to react for 250-300 minutes, cooling to be the room temperature, and slowly discharging redundant ammonia gas to be recycled within longer than 10 hours. The method is economic and environment-friendly, the utilization rate of 1,2-propylene dichloride is improved, the yield of the 1,2-propane diamine is improved, the cost is saved, and the emission of pollutant is reduced.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to a kind of 1, the synthetic method of 2-propylene diamine.
Background technology
1,2-propylene diamine is a kind of important fine-chemical intermediate, in fields such as organic synthesis, medicine, dyestuff, agricultural chemicals, chemical assistant, rubber plastic auxiliary agent and epoxy curing agents, has a wide range of applications.
1,2-propylene dichloride waste liquid is the by product in epoxy chloropropane and propylene oxide production process, approximately has every year tens thousand of tons; If insufficient utilization, not only causes the wasting of resources, and organochlorine compound can serious environment pollution.
Summary of the invention
In order to improve the utilization ratio of 1,2-propylene dichloride waste liquid, it is the synthetic method that raw material is produced 1,2-propylene diamine that the technical problem to be solved in the present invention is to provide a kind of industrial effluent with 1,2-propylene dichloride.
For addressing the above problem, the technical scheme that the present invention takes comprises following production stage:
(1) to autoclave, add catalyzer, aqueous solvent and 1,2-propylene dichloride, close autoclave;
(2) in reactor, pass into liquefied ammonia;
(3) be warming up to rapidly 160～180 ℃ and keep thermotonus 250～300min, be cooled to room temperature; To be greater than the slowly discharge excess of ammonia gas recovery use of time of 10h.
The catalyzer adding in step (1) refers to Cu
2o or CuO, the consumption of catalyzer is 2～5% of 1,2-propylene dichloride quality.
Step (2) passes into liquefied ammonia in reactor, and wherein 1, the mol ratio of 2-propylene dichloride and liquefied ammonia is 1:41～50.
The temperature of reaction of step (3) is further optimized for 165～175 ℃, and the reaction times is further optimized for 260～300 min.
Under reaction conditions after optimization, 1,2-propylene diamine yield surpasses 53%, simultaneously can many propylene of coproduction polyamines, and yield surpasses 48%.
Economy of the present invention, environmental protection, improved the utilization ratio of 1,2-propylene dichloride, also improved the productive rate of 1,2-propylene diamine, saved cost, reduced the discharge of pollutent.
Embodiment
Embodiment 1
(1) to autoclave, add aqueous solvent, 1,2-propylene dichloride and 2% Catalysts Cu
2o and CuO, Cu
2the ratio of O and CuO is 1:1, closes autoclave;
(2) proportionally 1,2-propylene dichloride: ammonia 1:41 passes into liquefied ammonia in still;
(3) be warming up to rapidly 165 ℃, and keep thermotonus 260 min, be cooled to room temperature; To be greater than the slowly discharge excess of ammonia gas recovery use of time of 10h.
Under the reaction conditions of embodiment 1,1,2-propylene diamine yield is 53%, simultaneously can many propylene of coproduction polyamines, and yield is 48%.
Embodiment 2
(1) to autoclave, add aqueous solvent, 1,2-propylene dichloride and 4% Catalysts Cu O, close autoclave;
(2) proportionally 1,2-propylene dichloride: ammonia 1:45 passes into liquefied ammonia in still;
(3) be warming up to rapidly 170 ℃, and keep thermotonus 280min, be cooled to room temperature; To be greater than the slowly discharge excess of ammonia gas recovery use of time of 10h.
Under the reaction conditions of embodiment 2,1,2-propylene diamine yield is 55%, simultaneously can many propylene of coproduction polyamines, and yield is 49%.
Embodiment 3
(1) to autoclave, add aqueous solvent, 1,2-propylene dichloride and 5% Catalysts Cu
2o and CuO, Cu
2o:CuO is 1:2, closes autoclave;
(2) according to mol ratio 1,2-propylene dichloride: ammonia 1:50 passes into liquefied ammonia in still;
(3) be warming up to rapidly 175 ℃, and keep thermotonus 290min, be cooled to room temperature; To be greater than the slowly discharge excess of ammonia gas recovery use of time of 10h.
Under this reaction conditions, 1,2-propylene diamine yield is 56%, simultaneously can many propylene of coproduction polyamines, and yield is 48%.
Claims (5)
1. a synthetic method for 2-propylene diamine, is characterized in that, the method for raw material, specifically comprises following production stage with 1,2-propylene dichloride:
(1) to autoclave, add catalyzer, aqueous solvent and 1,2-propylene dichloride, close autoclave;
(2) in reactor, pass into liquefied ammonia;
(3) be warming up to rapidly 160～180 ℃ and keep thermotonus 250～300min, be cooled to room temperature; To be greater than the slowly discharge excess of ammonia gas recovery use of time of 10h.
2. according to claim 1 a kind of 1, the synthetic method of 2-propylene diamine, is characterized in that, the catalyzer adding in step (1) refers to Cu
2o or CuO.
3. according to claim 1 a kind of 1, the synthetic method of 2-propylene diamine, is characterized in that, the consumption that adds catalyzer in step (1) is 2～5% of 1,2-propylene diamine quality.
4. according to claim 1 a kind of 1, the synthetic method of 2-propylene diamine, is characterized in that, step (2) passes into liquefied ammonia in reactor, wherein 1, and the mol ratio of 2-propylene dichloride and liquefied ammonia is 1:41～50.
5. according to claim 1 a kind of 1, the synthetic method of 2-propylene diamine, is characterized in that, the temperature of reaction of step (3) is 165～175 ℃, and the reaction times is 260～300 min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310569859.XA CN103664636A (en) | 2013-11-13 | 2013-11-13 | Method for synthesizing 1,2-propane diamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310569859.XA CN103664636A (en) | 2013-11-13 | 2013-11-13 | Method for synthesizing 1,2-propane diamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103664636A true CN103664636A (en) | 2014-03-26 |
Family
ID=50303527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310569859.XA Pending CN103664636A (en) | 2013-11-13 | 2013-11-13 | Method for synthesizing 1,2-propane diamine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103664636A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5137901A (en) * | 1988-07-28 | 1992-08-11 | Bayer Aktiengesellschaft | Substituted aminomethyltetralins and their heterocyclic analogues |
| 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 |
-
2013
- 2013-11-13 CN CN201310569859.XA patent/CN103664636A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5137901A (en) * | 1988-07-28 | 1992-08-11 | Bayer Aktiengesellschaft | Substituted aminomethyltetralins and their heterocyclic analogues |
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| 余章森等: "1,2-丙二胺合成工艺的研究", 《化学世界》, no. 4, 31 December 2009 (2009-12-31) * |
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| PB01 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20140326 |