CN108084035A - A kind of method of adiponitrile direct hydrogenation preparing hexanediamine under the conditions of alkali-free - Google Patents
A kind of method of adiponitrile direct hydrogenation preparing hexanediamine under the conditions of alkali-free Download PDFInfo
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- CN108084035A CN108084035A CN201711305350.9A CN201711305350A CN108084035A CN 108084035 A CN108084035 A CN 108084035A CN 201711305350 A CN201711305350 A CN 201711305350A CN 108084035 A CN108084035 A CN 108084035A
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- earth oxide
- adiponitrile
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- direct hydrogenation
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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
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
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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
- B01J23/78—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 alkali- or alkaline earth metals
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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
- B01J23/83—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 rare earths or actinides
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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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0027—Powdering
- B01J37/0036—Grinding
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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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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Abstract
The invention discloses a kind of methods of adiponitrile direct hydrogenation preparing hexanediamine under the conditions of alkali-free, i.e. in the case where alkali or aqueous ammonia conditions need not be added, the alkaline earth oxide or rare earth oxide-modified alchlor carried metal Raney nickel prepared using coprecipitation, in 60-200 DEG C of temperature, the certain density adiponitrile ethanol solution of direct hydrogenation under pressure 3-8MPa, products obtained therefrom obtain high-quality essence hexamethylene diamine after vacuum distillation.This method batch tank reactor i.e. suitable for being also applied for carrying out in continuous fixed bed reactors.
Description
Technical field
The invention belongs to field of chemical technology, are related to one kind adiponitrile direct hydrogenation under the conditions of alkali-free and prepare oneself
The method of diamines.
Background technology
Two amido functional groups of hexamethylene diamine all have high activity, this can be used as chemical intermediate production many
Multi-chemistry.Its industrial value be mainly reflected in monomer condensation or with other raw materials react generation condensed products, such as and adipic acid
Or decanedioic acid polycondensation prepares nylon66 fiber and nylon 610, then synthesizes other nylon resins, nylon fiber, polyamide again
The important civil use material such as ink.In addition, hexamethylene diamine is also widely used in mineral products (oil field demulsifier), agricultural (pesticide), builds
It builds (concrete additive) etc..In addition, under ultraviolet light irradiation, it is different that hexamethylene diamine can prepare adiponitrile with phosgene reaction
Cyanate is further continued for carrying out the polyurethane material of polymerisation production, is widely used in space industry.The application range of hexamethylene diamine
Constantly expand, the demand of downstream product increasingly increases, it is achieved that hexamethylene diamine industrial mass production is now primary appoints
Business.China's nylon market rapid growth at present, raw material hexamethylene diamine gradually shows the trend that supply falls short of demand, so hexamethylene diamine
New, efficient, large-scale industrial production technology research and development be very it is necessary to.
CN 1139392 and CN 103977819 individually discloses Raney catalyst in nitrile compounds Hydrogenation for amine
Everyway performance is excellent in compound.But because poison resistance is poor, mechanical performance is poor, Raney catalyst lifes are short, anti-
Should stir and hydraulic shock during it is easily broken, cause post-processing filtration difficulty, it is industrial be difficult by its from solution it is complete
The shortcomings of full removing, the little particle of broken generation can also block reactor.
United States Patent (USP) US 515543 reports Rh complex compound catalysts and is very suitable for catalysis adipic dinitrile hydrogenation reaction.Ru2
(H) 4 (PPh3) 3 type catalyst is 75 DEG C in reaction temperature, under conditions of Hydrogen Vapor Pressure is 2.2MPa, just reaches adiponitrile conversion
Rate 100%, the effect of hexamethylene diamine selectivity 99%, catalyst performance are excellent.Although homogeneous catalyst possesses active center distribution
The advantages that homogeneous, kinetics is simple, and selectivity of product is high, and by-product is few, but the price of this kind of catalyst is generally held high
It is expensive, and be difficult to separate from product and turn one's head so that subsequent purification difficulty complicated for operation limits such catalyst on a large scale
The stage of commercial Application；
The amorphous alloy catalyst prepared disclosed in Chinese invention patent CN104001516 and CN1191231C is efficiently urged
Change adipic dinitrile hydrogenation and prepare hexamethylene diamine, it is very high that shortcoming is that high-temperature fusion prepares alloy energy consumption；
In conclusion the production scale of China's hexamethylene diamine and technology are difficult to meet its demand rapid growth at present.It is and traditional
Preparing the technology of hexamethylene diamine with adipic dinitrile hydrogenation method, but almost all is monopolized by external large enterprise, and China can only be from foreign countries
A full set is introduced.So the hexamethylene diamine preparation process for greatly developing China's independent research is imperative.Adiponitrile catalytic hydrogenation at present
Raney Ni types catalytic mechanical poor performance used, it is broken, separate difficulty with product；Thermal stability is poor, in air easily certainly
Combustion, is not easy to store；Preparation process has a large amount of lye to discharge, and pollutes environment；Addition alkali or ammonium hydroxide is needed to inhibit secondary amine in reaction process
Production with tertiary amine is to improve the selectivity of hexamethylene diamine, etching apparatus.Homogeneous catalyst recycling is difficult, amorphous alloy catalyst
Production cost is excessively high.Stablize so developing, at low cost, hexamethylene diamine is selectively good and environmental-friendly loaded catalyst has weight
The application value and research significance wanted.
The content of the invention
Technical scheme：
The invention discloses a kind of methods of adiponitrile direct hydrogenation preparing hexanediamine under the conditions of alkali-free.Alkali need not added
Or under aqueous ammonia conditions, the alkaline earth oxide or rare earth oxide-modified alchlor that are prepared using coprecipitation are loaded
MetalNicatalyst, the certain density adiponitrile ethanol solution of direct hydrogenation, gained at 60-200 DEG C of temperature, pressure 3-8MPa
Product obtains high-quality essence hexamethylene diamine after vacuum distillation.
Institute in the alkaline earth oxide or rare earth oxide-modified alchlor carried metal Raney nickel
The content for the metallic nickel being related to is the 15%-45% of catalyst gross mass.
Institute in the alkaline earth oxide or rare earth oxide-modified alchlor carried metal Raney nickel
The alkaline earth oxide being related to is that one or more kinds of mixing, content are total for catalyst in MgO, CaO, SrO, BaO
The 1%-10% of quality；Rare-earth oxide is La2O3、ZrO2、CeO2One or both of it is mixed above, content is
The 1%-10% of catalyst total amount.
The concentration of the certain density adiponitrile ethanol solution is weight percent 10%-40%.
The direct hydrogenation is carried out or carried out in continuous fixed bed reactors in batch tank reactor.
Description of the drawings
Fig. 1 is the process flow diagram of the present invention.
Specific embodiment
Below in conjunction with attached drawing and technical solution, the specific embodiment further illustrated the present invention.
1 NiLa/MgO-Al of embodiment2O3The preparation of catalyst
According to the metering of catalyst activity W metal and oxide carrier ratio, the nickel nitrate and aluminum nitrate of certain mass are taken,
It is dissolved in the magnesium nitrate and lanthanum nitrate of opposite metering ratio in deionized water, it is molten to be configured to the mixing that aluminium ion concentration is about 1mol/L
Liquid.The natrium carbonicum calcinatum of 1.1 times of stoichiometric ratios of opposing metallic ion is taken to be dissolved in a certain amount of deionized water again, is configured to pH=
11 sodium carbonate liquor.Then above two settled solution cocurrent is instilled to tri- mouthfuls of burnings of 250mL equipped with 5~10mL deionized waters
In bottle, drop speed is 1mL/min, i.e. 3s/ drops.45 DEG C of constant temperature, and violent stirring are kept with oil bath during dropwise addition, this
When can gradually appear jade-green precipitation.After dripping, pH=6~7 of test mixing thing, then adjusted and mixed with sodium carbonate liquor
Close object pH=8.When aging 8 is small, and keep 45 DEG C of constant temperature and violent stirring.Mixture is filtered after aging, first with 400mL with
On the washing of 75 DEG C of deionized waters be precipitated to cleaning solution and be in neutrality, then washed with the methanol room temperature of more than 100mL, in order to
The sodium ion in sediment is removed as far as possible.Then sediment is placed in electric drying oven with forced convection, dry 10 is small at 110 DEG C
When.It is to be precipitated be cooled to room temperature after, with mortar grinder into the powder of no granular sensation, be then placed in tube furnace and roasted.
Embodiment 2NiCe/BaO-Al2O3The preparation of catalyst
According to the metering of catalyst activity W metal and oxide carrier ratio, the nickel nitrate and aluminum nitrate of certain mass are taken,
It is dissolved in the barium nitrate and cerous nitrate of opposite metering ratio in deionized water, it is molten to be configured to the mixing that aluminium ion concentration is about 1mol/L
Liquid.The natrium carbonicum calcinatum of 1.1 times of stoichiometric ratios of opposing metallic ion is taken to be dissolved in a certain amount of deionized water again, is configured to pH=
11 sodium carbonate liquor.Then above two settled solution cocurrent is instilled to tri- mouthfuls of burnings of 250mL equipped with 5~10mL deionized waters
In bottle, drop speed is 1mL/min, i.e. 3s/ drops.45 DEG C of constant temperature, and violent stirring are kept with oil bath during dropwise addition, this
When can gradually appear jade-green precipitation.After dripping, pH=6~7 of test mixing thing, then adjusted and mixed with sodium carbonate liquor
Close object pH=8.When aging 8 is small, and keep 45 DEG C of constant temperature and violent stirring.Mixture is filtered after aging, first with 400mL with
On the washing of 75 DEG C of deionized waters be precipitated to cleaning solution and be in neutrality, then washed with the methanol room temperature of more than 100mL, in order to
The sodium ion in sediment is removed as far as possible.Then sediment is placed in electric drying oven with forced convection, dry 10 is small at 110 DEG C
When.It is to be precipitated be cooled to room temperature after, with mortar grinder into the powder of no granular sensation, be then placed in tube furnace and roasted.
Embodiment 3NiZr/SrO-Al2O3The preparation of catalyst
According to the metering of catalyst activity W metal and oxide carrier ratio, the nickel nitrate and aluminum nitrate of certain mass are taken,
It is dissolved in the zirconium nitrate and strontium nitrate of opposite metering ratio in deionized water, it is molten to be configured to the mixing that aluminium ion concentration is about 1mol/L
Liquid.The natrium carbonicum calcinatum of 1.1 times of stoichiometric ratios of opposing metallic ion is taken to be dissolved in a certain amount of deionized water again, is configured to pH=
11 sodium carbonate liquor.Then above two settled solution cocurrent is instilled to tri- mouthfuls of burnings of 250mL equipped with 5~10mL deionized waters
In bottle, drop speed is 1mL/min, i.e. 3s/ drops.45 DEG C of constant temperature, and violent stirring are kept with oil bath during dropwise addition, this
When can gradually appear jade-green precipitation.After dripping, pH=6~7 of test mixing thing, then adjusted and mixed with sodium carbonate liquor
Close object pH=8.When aging 8 is small, and keep 45 DEG C of constant temperature and violent stirring.Mixture is filtered after aging, first with 400mL with
On the washing of 75 DEG C of deionized waters be precipitated to cleaning solution and be in neutrality, then washed with the methanol room temperature of more than 100mL, in order to
The sodium ion in sediment is removed as far as possible.Then sediment is placed in electric drying oven with forced convection, dry 10 is small at 110 DEG C
When.It is to be precipitated be cooled to room temperature after, with mortar grinder into the powder of no granular sensation, be then placed in tube furnace and roasted.
Embodiment 4
The adiponitrile ethanol solution that mass fraction is 10% is added in reaction kettle, the NiLa/MgO-Al that will have been reduced2O3
Catalyst is added in reaction kettle.After completing sealing, with air in hydrogen displacement kettle, gas is then flushed with hydrogen to the reaction pressure set
6MPa is slowly heated reaction kettle.After reaching 110 DEG C of reaction temperature, open and stir and start timing, the rotating speed of stirring remains
800r/min.After certain reaction time, stirring and heating unit are closed, to room temperature, pressure release to normal pressure negates cooling reaction kettle
Mixture after answering is 99% through chromatography conversion ratio, and the selectivity of hexamethylene diamine is 95%.It is obtained after being evaporated under reduced pressure and refining high
The hexamethylene diamine of purity.
Embodiment 5
The adiponitrile ethanol solution that mass fraction is 40% is added in reaction kettle, the NiZr/SrO-Al that will have been reduced2O3
Catalyst is added in reaction kettle.After completing sealing, with air in hydrogen displacement kettle, gas is then flushed with hydrogen to the reaction pressure set
8MPa is slowly heated reaction kettle.After reaching 200 DEG C of reaction temperature, open and stir and start timing, the rotating speed of stirring remains
800r/min.After certain reaction time, stirring and heating unit are closed, to room temperature, pressure release to normal pressure negates cooling reaction kettle
Mixture after answering is 99% through chromatography conversion ratio, and the selectivity of hexamethylene diamine is 90%.It is obtained after being evaporated under reduced pressure and refining high
The hexamethylene diamine of purity.
Embodiment 6
By mass fraction be 20% adiponitrile ethanol solution through pump mixed with hydrogen after, into equipped with NiZr/SrO-
Al2O3In the fixed bed reactors of catalyst.In 60 DEG C, pressure 8MPa of reaction temperature, hydrogen-oil ratio 300, mass space velocity 1h-1Condition
Under, collection, which negates, answers rear mixture, is 99% through chromatography conversion ratio, and the selectivity of hexamethylene diamine is 97%.Through vacuum distillation
The hexamethylene diamine of high-purity is obtained after refined.
Embodiment 7
By mass fraction be 40% adiponitrile ethanol solution through pump mixed with hydrogen after, into equipped with NiCe/BaO-
Al2O3In the fixed bed reactors of catalyst.In 200 DEG C, pressure 3MPa of reaction temperature, hydrogen-oil ratio 300, mass space velocity 1h-1Item
Under part, collection, which negates, answers rear mixture, is 99% through chromatography conversion ratio, and the selectivity of hexamethylene diamine is 95%.It is steamed through decompression
Evaporate the hexamethylene diamine that high-purity is obtained after refining.
Claims (5)
1. a kind of method of adiponitrile direct hydrogenation preparing hexanediamine under the conditions of alkali-free, which is characterized in that alkali or ammonia need not added
Under water condition, the alkaline earth oxide or rare earth oxide-modified alchlor carried metal that are prepared using coprecipitation
Raney nickel, the certain density adiponitrile ethanol solution of direct hydrogenation, products obtained therefrom at 60-200 DEG C of temperature, pressure 3-8MPa
High-quality essence hexamethylene diamine is obtained after vacuum distillation.
2. according to the method described in claim 1, it is characterized in that, the alkaline earth oxide or rare-earth oxide
The content of involved metallic nickel is the 15%- of catalyst gross mass in modified alchlor carried metal Raney nickel
45%.
3. method according to claim 1 or 2, which is characterized in that the alkaline earth oxide or rare earth metal oxygen
Compound is modified alkaline earth oxide involved in alchlor carried metal Raney nickel as in MgO, CaO, SrO, BaO
One or more mixing, content are the 1%-10% of catalyst gross mass；Rare-earth oxide is La2O3、ZrO2、
CeO2One or both of it is mixed above, content be catalyst total amount 1%-10%.
4. method according to claim 1 or 2, which is characterized in that the certain density adiponitrile ethanol solution
Concentration is weight percent 10%-40%.
5. according to the method described in claim 3, it is characterized in that, the direct hydrogenation be in batch tank reactor into
Row carries out in continuous fixed bed reactors.
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| CN201711305350.9A CN108084035A (en) | 2017-12-11 | 2017-12-11 | A kind of method of adiponitrile direct hydrogenation preparing hexanediamine under the conditions of alkali-free |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109647419A (en) * | 2018-12-20 | 2019-04-19 | 大连理工大学 | A kind of rare earth oxide-modified adipic dinitrile hydrogenation preparing hexanediamine high-selectivity catalyst, preparation method and application |
| CN112337409A (en) * | 2020-11-25 | 2021-02-09 | 重庆华峰化工有限公司 | Production system of hexamethylene diamine |
| CN114797880A (en) * | 2022-06-23 | 2022-07-29 | 北京弗莱明科技有限公司 | Composite metal oxide catalyst and preparation method and application thereof |
| CN115894253A (en) * | 2022-11-10 | 2023-04-04 | 山东阳谷华泰化工股份有限公司 | Production process for synthesizing hexamethylene diamine by catalytic hydrogenation of adiponitrile |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109647419A (en) * | 2018-12-20 | 2019-04-19 | 大连理工大学 | A kind of rare earth oxide-modified adipic dinitrile hydrogenation preparing hexanediamine high-selectivity catalyst, preparation method and application |
| CN112337409A (en) * | 2020-11-25 | 2021-02-09 | 重庆华峰化工有限公司 | Production system of hexamethylene diamine |
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| CN114797880A (en) * | 2022-06-23 | 2022-07-29 | 北京弗莱明科技有限公司 | Composite metal oxide catalyst and preparation method and application thereof |
| CN115894253A (en) * | 2022-11-10 | 2023-04-04 | 山东阳谷华泰化工股份有限公司 | Production process for synthesizing hexamethylene diamine by catalytic hydrogenation of adiponitrile |
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Application publication date: 20180529 |