CN103420843A - Synthetic method for diiso-tridecylamine - Google Patents
Synthetic method for diiso-tridecylamine Download PDFInfo
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Abstract
The invention discloses a synthetic method for diiso-tridecylamine, which includes the following steps: firstly adding isotridecyl alcohol and copper and nickel supported catalyst in a high pressure reactor; then introducing nitrogen in to replace air, and then introducing liquid ammonia and hydrogen; increasing the temperature to 120-250 DEG C; reacting for 5-15 h under the reaction pressure of 3-10 Mpa, then keeping stirring during the reaction; gradually reducing the temperature to 50-100 DEG C, introducing hydrogen in continuously to replace ammonia gas in the high pressure reactor, keeping the reaction pressure inside the high pressure reactor to be 0.1-1 Mpa, and besides keeping stirring and reacting for 1-10 h after increasing the temperature to 180-240 DEG C, wherein during the reaction, hydrogen is continuously introduced in to replace ammonia gas and stir is kept; cooling and emptying to the ordinary pressure after the reaction is finished; discharging and filtering the catalyst; distilling filtrate to obtain the diiso-tridecylamine. The synthetic method has the advantages of simple technology, low cost and high yield.
Description
Technical field
The invention belongs to the field of chemical synthesis, be specifically related to the synthetic method of two different tridecyl amines.
Background technology
Two different tridecyl amines are a kind of special secondary amine series products, for colourless or micro-yellow has the fluid cpds of amine flavor.Be widely used as chemical intermediate, flotation agent, corrosion inhibitor, plasticizer, lubricating oil additive, noble metal extractant, tensio-active agent etc.Present stage, the domestic people of having of similar synthesis technique of two different tridecyl amines reports that take isomerous tridecanol and ammonia is raw material, take Raney's nickel as catalyzer, the two tridecyl amines of synthesising different structure.But this process catalyst can not be applied mechanically, and selectivity is low, only has 81.5%, and total recovery is low, is not suitable for industrialized production.Consult external pertinent literature also without the report of synthetic method, market outlook are more wide.
Summary of the invention
The purpose of this invention is to provide a kind of technique simple, low cost, high yield, the synthetic method of two different tridecyl amines of environmental protection.
For achieving the above object, the present invention has adopted following technical scheme: the synthetic method of described two different tridecyl amines comprises the following steps:
(1), first in autoclave, add different tridecanol, then add copper Ni type catalyzer, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again liquefied ammonia and hydrogen, then be warming up to 120～250 ℃, and react 5～15h under the reaction pressure of 3～10Mpa, remain stirring in above-mentioned reaction process;
(2), then be cooled to gradually 50～100 ℃, discharge hydrogen and ammonia in autoclave, and pass into continuously hydrogen ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.1～1Mpa, keep stirring simultaneously; Then be warming up to 180～240 ℃, and react 1～10h under this reaction pressure, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain stirring;
(3), after question response finishes, the reaction under high pressure temperature in the kettle is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate distillation obtains two different tridecyl amine finished products.
Further, the synthetic method of aforesaid two different tridecyl amines, wherein: the mol ratio of described different tridecanol and liquefied ammonia is 1:(1～10); The consumption of described copper Ni type catalyzer is 5～20% of different tridecanol quality; The hydrogen be filled with is 0.1-1Mpa.
Further, the synthetic method of aforesaid two different tridecyl amines, wherein: described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for the 5-20% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for the 5-20% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for the 1-10% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for the 1-10% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for the 1-10% of copper Ni type total catalyst weight.
Side of the present invention answers equation as follows:
Enforcement by technique scheme the invention has the beneficial effects as follows:
(1), raw material of the present invention is easy to get, technique is simple, easy to operate, environmental protection.
(2), this synthesis technique can complete in an autoclave, greatly reduced investment and the production efficiency of equipment.
(3), the present invention only need adopt a kind of catalyzer can complete whole reactions, after rectifying, the low fraction of gained can be applied mechanically as raw material again, the selectivity of product obtains larger raising, yield is high, total recovery surpasses 85%, product purity surpasses 99%.
Embodiment
Below by specific embodiment, the present invention is described in further detail.
Embodiment 1
(1), first in the autoclave of 1L, add 200g(1mol) different tridecanol, add 10g copper Ni type catalyzer again, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again 85g(5mol) anhydrous liquid ammonia and 0.3Mpa hydrogen, then be warming up to 210 ℃ and react 13h under the reaction pressure of 5Mpa, in above-mentioned reaction process, remain high-speed stirring;
(2), then be cooled to gradually 90 ℃, and discharge ammonia and hydrogen in autoclave, and pass into continuously hydrogen the ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.4Mpa, keep high-speed stirring simultaneously; Then be warming up to 220 ℃, and react 8h under the reaction pressure of 0.4Mpa, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain high-speed stirring;
(3), after question response finishes, the temperature in autoclave is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate rectifying obtains the two different tridecyl amine finished product 168g that purity is 99.2%, total recovery 88%.
Described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for 5% of copper Ni type total catalyst weight, carclazyte accounts for 55% of copper Ni type total catalyst weight.
Embodiment 2
(1), first in the autoclave of 1L, add 200g(1mol) different tridecanol, add 20g copper Ni type catalyzer again, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again 85g(5mol) anhydrous liquid ammonia and 0.3Mpa hydrogen, then be warming up to 190 ℃ and react 10h under the reaction pressure of 5Mpa, in above-mentioned reaction process, remain high-speed stirring;
(2), then be cooled to gradually 100 ℃, and discharge ammonia and hydrogen in autoclave, and pass into continuously hydrogen the ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.5Mpa, keep high-speed stirring simultaneously; Then be warming up to 210 ℃, and react 6h under the reaction pressure of 0.5Mpa, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain high-speed stirring;
(3), after question response finishes, the temperature in autoclave is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate rectifying obtains two different tridecyl amine finished product 175g of purity 99.1%, and total recovery is 91.6%.
Described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for 5% of copper Ni type total catalyst weight, carclazyte accounts for 55% of copper Ni type total catalyst weight.
Embodiment 3
(1), first in the autoclave of 1L, add 200g(1mol) different tridecanol, add 30g copper Ni type catalyzer again, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again 85g(5mol) anhydrous liquid ammonia and 0.3Mpa hydrogen, then be warming up to 240 ℃ and react 6h under the reaction pressure of 10Mpa, in above-mentioned reaction process, remain high-speed stirring;
(2), then be cooled to gradually 50 ℃, and discharge ammonia and hydrogen in autoclave, and pass into continuously hydrogen the ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.5Mpa, keep high-speed stirring simultaneously; Then be warming up to 210 ℃, and react 5h under the reaction pressure of 0.5Mpa, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain high-speed stirring;
(3), after question response finishes, the temperature in autoclave is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate rectifying obtains two different tridecyl amine finished product 180g of purity 99.3%, and total recovery is 94.2%.
Described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for 5% of copper Ni type total catalyst weight, carclazyte accounts for 55% of copper Ni type total catalyst weight.
Embodiment 4
(1), first in the autoclave of 1L, add 200g(1mol) different tridecanol, add 10g copper Ni type catalyzer again, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again 17g(1mol) anhydrous liquid ammonia and 0.3Mpa hydrogen, then be warming up to 230 ℃ and react 13h under the reaction pressure of 3Mpa, in above-mentioned reaction process, remain high-speed stirring;
(2), then be cooled to gradually 90 ℃, and discharge ammonia and hydrogen in autoclave, and pass into continuously hydrogen the ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.4Mpa, keep high-speed stirring simultaneously; Then be warming up to 240 ℃, and react 8h under the reaction pressure of 0.4Mpa, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain high-speed stirring;
(3), after question response finishes, the temperature in autoclave is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, it is 99.2% 2 different tridecyl amine finished product 163g that filtrate rectifying obtains purity, total recovery is 85.3%.
Described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for 5% of copper Ni type total catalyst weight, carclazyte accounts for 55% of copper Ni type total catalyst weight.
Embodiment 5
(1), first in the autoclave of 1L, add 200g(1mol) different tridecanol, add 40g copper Ni type catalyzer again, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again 17g(1mol) anhydrous liquid ammonia and 0.3Mpa hydrogen, then be warming up to 220 ℃ and under the reaction pressure of 3Mpa the reaction 9 hours, remain high-speed stirring in above-mentioned reaction process;
(2), then be cooled to gradually 90 ℃, and discharge ammonia and hydrogen in autoclave, and pass into continuously hydrogen the ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.4Mpa, keep high-speed stirring simultaneously; Then be warming up to 190 ℃, and react 5h under the reaction pressure of 0.4Mpa, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain high-speed stirring;
(3), after question response finishes, the temperature in autoclave is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate rectifying obtains the two different tridecyl amine finished product 165g that purity is 99.5%, and total recovery is 86.4%.
Described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for 1% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for 1% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for 1% of copper Ni type total catalyst weight, carclazyte accounts for 87% of copper Ni type total catalyst weight.
Embodiment 6
(1), first in the autoclave of 1L, add 200g(1mol) different tridecanol, add 10g copper Ni type catalyzer again, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again 170g(10mol) anhydrous liquid ammonia and 0.5Mpa hydrogen, then be warming up to 180 ℃ and react 11h under the reaction pressure of 10Mpa, in above-mentioned reaction process, remain high-speed stirring;
(2), then be cooled to gradually 90 ℃, and discharge ammonia and hydrogen in autoclave, and pass into continuously hydrogen the ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.4Mpa, keep high-speed stirring simultaneously; Then be warming up to 200 ℃, and react 7h under the reaction pressure of 0.4Mpa, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain high-speed stirring;
(3), after question response finishes, the temperature in autoclave is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate rectifying obtains the two different tridecyl amine finished product 178g that purity is 99.3%, and total recovery is 93.2%.
Described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for 15% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for 5% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for 5% of copper Ni type total catalyst weight, carclazyte accounts for 55% of copper Ni type total catalyst weight.
Embodiment 7
(1), first in the autoclave of 1L, add 200g(1mol) different tridecanol, add 40g copper Ni type catalyzer again, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again 170g(10mol) anhydrous liquid ammonia and 0.5Mpa hydrogen, then be warming up to 170 ℃ and react 6h under the reaction pressure of 10Mpa, in above-mentioned reaction process, remain high-speed stirring;
(2), then be cooled to gradually 90 ℃, and discharge ammonia and hydrogen in autoclave, and pass into continuously hydrogen the ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.4Mpa, keep high-speed stirring simultaneously; Then be warming up to 180 ℃, and react 5h under the reaction pressure of 0.4Mpa, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain high-speed stirring;
(3), after question response finishes, the temperature in autoclave is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate rectifying obtains two different tridecyl amine finished product 184g of purity 99.2%, and total recovery is 96.3%.
Described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for 20% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for 20% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for 10% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for 10% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for 10% of copper Ni type total catalyst weight, carclazyte accounts for 30% of copper Ni type total catalyst weight.
What more than exemplify is only some specific embodiments of the present invention; obviously the invention is not restricted to above embodiment; also have a lot of distortion, all distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention, all should belong to protection scope of the present invention.
Claims (3)
1. the synthetic method of two different tridecyl amines is characterized in that: comprise the following steps:
(1), first in autoclave, add different tridecanol, then add copper Ni type catalyzer, after then passing into nitrogen the air displacement in autoclave being gone out, pass into again liquefied ammonia and hydrogen, then be warming up to 120～250 ℃, and react 5～15h under the reaction pressure of 3～10Mpa, remain stirring in above-mentioned reaction process;
(2), then be cooled to gradually 50～100 ℃, discharge hydrogen and ammonia in autoclave, and pass into continuously hydrogen ammonia in autoclave is displaced, the reaction pressure in autoclave is maintained to 0.1～1Mpa, keep stirring simultaneously; Then be warming up to 180～240 ℃, and react 1～10h under this reaction pressure, continue to pass into the ammonia in the hydrogen exchange autoclave in above-mentioned reaction process, and remain stirring;
(3), after question response finishes, the reaction under high pressure temperature in the kettle is dropped to normal temperature, pressure-emptying to normal pressure, then discharging, filtering catalyst, filtrate distillation obtains two different tridecyl amine finished products.
2. the synthetic method of two different tridecyl amines according to claim 1, it is characterized in that: the mol ratio of described different tridecanol and liquefied ammonia is 1:(1～10); The consumption of described copper Ni type catalyzer is 5～20% of different tridecanol quality; The hydrogen be filled with is 0.1-1Mpa.
3. the synthetic method of two different tridecyl amines according to claim 1 and 2, it is characterized in that: described copper Ni type catalyzer is with cupric nitrate, nickelous nitrate is actives, take carclazyte as carrier, pass through coprecipitation method, dry, roasting and a kind of powder catalyst of preparing, in described copper Ni type catalyzer, Main Components copper accounts for the 5-20% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, Main Components nickel accounts for the 5-20% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition aluminium accounts for the 1-10% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition chromium accounts for the 1-10% of copper Ni type total catalyst weight, in described copper Ni type catalyzer, auxiliary composition iron accounts for the 1-10% of copper Ni type total catalyst weight.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110270279A (en) * | 2019-07-12 | 2019-09-24 | 江苏万盛大伟化学有限公司 | A kind of fixed bed reactors and its application for the different tridecyl amine of continuous production two |
| CN110776430A (en) * | 2018-07-31 | 2020-02-11 | 中国石油化工股份有限公司 | Preparation method of tri (2-aminoethyl) amine |
| CN111470972A (en) * | 2020-04-24 | 2020-07-31 | 安徽天择化工有限公司 | Isooctyl isotridecyl secondary amine and preparation method and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110776430A (en) * | 2018-07-31 | 2020-02-11 | 中国石油化工股份有限公司 | Preparation method of tri (2-aminoethyl) amine |
| CN110776430B (en) * | 2018-07-31 | 2022-10-14 | 中国石油化工股份有限公司 | Preparation method of tri (2-aminoethyl) amine |
| CN110270279A (en) * | 2019-07-12 | 2019-09-24 | 江苏万盛大伟化学有限公司 | A kind of fixed bed reactors and its application for the different tridecyl amine of continuous production two |
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| CN111470972A (en) * | 2020-04-24 | 2020-07-31 | 安徽天择化工有限公司 | Isooctyl isotridecyl secondary amine and preparation method and application thereof |
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Application publication date: 20131204 |