CN100435947C - Catalyst for preparing fatty primary amine by fatty nitrile hydrogenation and application thereof - Google Patents
Catalyst for preparing fatty primary amine by fatty nitrile hydrogenation and application thereof Download PDFInfo
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- CN100435947C CN100435947C CNB200610102303XA CN200610102303A CN100435947C CN 100435947 C CN100435947 C CN 100435947C CN B200610102303X A CNB200610102303X A CN B200610102303XA CN 200610102303 A CN200610102303 A CN 200610102303A CN 100435947 C CN100435947 C CN 100435947C
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Abstract
The invention discloses a making method of hydrogenated primary fat amine, which comprises the following steps: setting the molar rate of nickel, cobalt, auxiliary catalyst and rare earth at 100:0.01-2.0:1-15:0.01-1; allocating soluble metal salt into composite solution with density at 0.1-1mol/L; heating to 60-80 deg.c; adding water and hydrazine/metal ion with molar rate at 1-5 and potassium borohydride/metal ion with molar rate at 0.01-0.5; stirring under 60-80 deg.c for 3-5 min; heating; stirring; washing until neutral; extracting into vacuum; drying; reserving in the anhydrous alcohol.
Description
Technical field
The present invention relates to catalyst and the method for making and the application of fatty primary amine by fatty nitrile hydrogenation.
Background technology
Announced a kind of preparation method of primary amine among the document CN 1088198A.In the document with the nickel of carrier and/or Co catalysts being arranged at 140 ℃, pressure 1MPa NH
3+ 2MPa H
2The selectivity of carrying out the nitrile hydrogenation primary amine under the condition is 85%.Announced a kind of manufacture method of ethamine class among the clear 53-50109 of document Japan Patent JP.Being raw material with the crude acetonitrile that contains hydrogen cyanide in the document, in the presence of organic solvent, is catalyst with the skeleton nickel, in the hydrogen dividing potential drop is 0.5～10.0MPa, temperature is under 40～200 ℃ of conditions, carries out hydrogenation reaction and generates ethamine, and wherein organic solvent is ethanol and toluene.As calculated, the yield of its ethamine is up to 95.4%, and is lower, in addition its reaction time longer, needed three hours just can finish reaction, catalyst amount is bigger, is generally 12% of acetonitrile raw material, catalyst activity is lower.
Summary of the invention:
It is short to the purpose of this invention is to provide a kind of reaction time, catalyst and the method for making and the application of the Arneel SD liquid-phase hydrogenatin primary amine by fatty that the primary amine yield is high.
Catalyst molar ratio of the present invention consists of:
Nickel: cobalt: co-catalyst: rare earth metal=100: 0.01～2.0: 1～15: 0.01～1
Aforesaid co-catalyst be in chromium, iron, copper or the molybdenum one or more
Catalyst molar ratio is formed preferable range:
Nickel: cobalt: co-catalyst: rare earth metal=100: 0.01～0.05: 8～11: 0.01～0.05.Method for preparing catalyst of the present invention is as follows:
The soluble metallic salt that catalyst is formed is made into the mixed aqueous solution that concentration is 0.1～1mol/L in proportion, be warming up to 60～80 ℃, adding is hydrazine hydrate and the potassium borohydride co-conducer that hydrazine hydrate/metal ion=1～5 and potassium borohydride/metal ion=0.01～0.5 is formed in molar ratio, under 60～80 ℃ of constant temperatures, stir 3-5min and stop heating and stirring, after be washed to neutrality, vacuumizing drying, be kept in the absolute ethyl alcohol.
Aforesaid soluble metallic salt is chlorate, sulfate or nitrate.
Application of Catalyst method of the present invention is as follows:
The present invention is when fatty primary amine by fatty nitrile hydrogenation, Hydrogen Vapor Pressure is that normal pressure is between the 5.0MPa, reaction temperature is 60～170 ℃, solvent selects ethanol, solvent load is 0～5 times of an Arneel SD raw material quality, it is 0.1%～5% of Arneel SD raw material quality that auxiliary agent is selected from the potash consumption, and catalyst amount is 0.1%～5% of an Arneel SD raw material quality.More preferably 110 ℃～130 ℃ scopes of reaction temperature, hydrogen pressure is 1.0～2.5MPa scope more preferably.
Aforesaid Arneel SD is RCN, R-NH-CH
2-CH
2CN, R-O-CH
2-CH
2CN, wherein R=C1～18.
The present invention compared with prior art has following advantage:
1, owing to nitrile catalyst hydrogenation process, the course of reaction of experience imines.The activity of imines is very high, in order to reaction intermediate and principal product further reaction taking place, generates the selectivity and the conversion ratio of accessory substances influence reactions such as secondary amine, tertiary amine by condensation, aminolysis, reaction such as crosslinked.The custom catalysts of nitrile hydrogenation is divided into nickel system and cobalt is two big classes, generally speaking the active height of the nickel catalyst catalyst selectivity height that cobalt is but selectivity is lower but activity is lower.The present invention is by introducing the selectivity that cobalt has greatly improved Raney nickel in Raney nickel, introduce the component of at least a Fe of being selected from, Cu, Mo, rare earth element simultaneously, be that catalyst and its main reaction adapt, strengthened the absorption of catalyst, thereby improved the activity of catalyst main reaction to unsaturated compounds such as imines.The reactivity height still keeps greater activity under the low pressure condition, pressure for 1.6MPa time reaction can in 1h～2h, finish.
2, reaction selectivity height, the selectivity of itrile group hydrogenation system primary amine reduce with carbochain and reduce, and the present invention also can reach 99% to the shortest acetonitrile selectivity of carbochain.
The specific embodiment
Implementation column 1:
In molar ratio for Ni: Co: Cr: La=100: above-mentioned metal nitrate was made into the mixed aqueous solution that concentration is 0.2mol/L in 0.01: 8: 0.03, be warming up to 70 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=2, potassium borohydride/metal ion=0.1 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 110 ℃ of reaction temperatures, hydrogen pressure 1.6MPa, with ethanol is solvent, 90g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 1g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 60 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 96%.
Embodiment 2
In molar ratio for Ni: Co: Fe: La=100: above-mentioned metal sulfate was made into the aqueous solution that concentration is 0.3mol/L in 0.01: 11: 0.05, be warming up to 80 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=5, potassium borohydride/metal ion=0.04 proportioning and potassium borohydride co-conducer reaction 4min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 130 ℃ of reaction temperatures, hydrogen pressure 1.8MPa, with ethanol is solvent, 120g ethanol, 30g acetonitrile, 1g catalyst, and other adds 1.5g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 70 minutes, the acetonitrile conversion ratio is 98%, and the ethamine yield is 97.1%.
Embodiment 3
In molar ratio for Ni: Co: Mo: La=100: above-mentioned metal chlorate was made into the aqueous solution that concentration is 0.5mol/L in 0.04: 9: 0.03, be warming up to 65 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=3.5, potassium borohydride/metal ion=0.03 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 2.1MPa, with ethanol is solvent, 70g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 0.3g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 60 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 97.3%.
Embodiment 4
In molar ratio for Ni: Co: Cu: La=100: above-mentioned metal nitrate was made into the aqueous solution that concentration is 0.5mol/L in 0.03: 9: 0.04, be warming up to 75 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=4, potassium borohydride/metal ion=0.4 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 2.5MPa, with ethanol is solvent, 100g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 1g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 60 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 97%.
Embodiment 5
In molar ratio for Ni: Co: Cr: Mo: La=100: 0.02: 3: 8: 0.02 is made into the aqueous solution that concentration is 0.8mol/L with above-mentioned metal nitrate, be warming up to 65 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=4, potassium borohydride/metal ion=0.5 proportioning and potassium borohydride co-conducer reaction 3min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 2.5MPa, with ethanol is solvent, 90g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 0.15g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 60 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 99.2%.
Embodiment 6
In molar ratio for Ni: Co: Cr: Cu: La=100: 0.02: 7: 1: 0.01 is made into the aqueous solution that concentration is 0.1mol/L with above-mentioned metal nitrate, be warming up to 80 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=3, potassium borohydride/metal ion=0.35 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 2.0MPa, with ethanol is solvent, 90g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 1.2g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 80 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 98.4%.
Embodiment 7
In molar ratio for Ni: Co: Cr: Fe: La=100: 0.02: 7: 4: 0.05 is made into the aqueous solution that concentration is 0.4mol/L with above-mentioned metal nitrate, be warming up to 70 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=1, potassium borohydride/metal ion=0.03 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 110 ℃ of reaction temperatures, hydrogen pressure 1.0MPa, with ethanol is solvent, 150g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 0.35g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 160 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 98.8%.
Embodiment 8
In molar ratio for Ni: Co: Cu: Fe: La=100: 0.02: 8: 1: 0.03 is made into the aqueous solution that concentration is 0.7mol/L with above-mentioned metal nitrate, be warming up to 75 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=1, potassium borohydride/metal ion=0.5 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 2.0MPa, with ethanol is solvent, 90g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 0.15g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 60 minutes, the acetonitrile conversion ratio is 98%, and the ethamine yield is 96%.
Embodiment 9
In molar ratio for Ni: Co: Mo: Fe: La=100: 0.02: 7: 2: 0.03 is made into the aqueous solution that concentration is 0.7mol/L with above-mentioned metal nitrate, be warming up to 70 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=3, potassium borohydride/metal ion=0.05 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 2.4MPa, with ethanol is solvent, 100g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 0.6g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 60 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 99.2%.
Embodiment 10
In molar ratio for Ni: Co: Mo: Cu: La=100: 0.05: 3: 6: 0.02 is made into the aqueous solution that concentration is 1mol/L with above-mentioned metal nitrate, be warming up to 60 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=5, potassium borohydride/metal ion=0.01 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 1.9MPa, with ethanol is solvent, 60g ethanol, 30g acetonitrile, 1.5g catalyst, and other adds 1.3g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 60 minutes, the acetonitrile conversion ratio is 100%, and the ethamine yield is 97%.
Embodiment 11
In molar ratio for Ni: Co: Mo: Cu: Ce=100: 0.02: 2: 9: 0.04 is made into the aqueous solution that concentration is 0.35mol/L with above-mentioned metal nitrate, be warming up to 75 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=4, potassium borohydride/metal ion=0.42 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 120 ℃ of reaction temperatures, hydrogen pressure 2.1MPa, 100g stearonitrile, 1.0g catalyst, other adds 4g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 110 minutes, the stearonitrile conversion ratio is 100%, and the octadecylamine yield is 99.4%.
Embodiment 12
In molar ratio for Ni: Co: Mo: Fe: Cu: Sm=100: 0.02: 3: 3: above-mentioned metal nitrate was made into the aqueous solution that concentration is 0.25mol/L in 4: 0.02, be warming up to 80 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=3, potassium borohydride/metal ion=0.35 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 110 ℃ of reaction temperatures, hydrogen pressure 1.8MPa, 100g palmitonitrile, 1.0g catalyst, other adds 3g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 90 minutes, the palmitonitrile conversion ratio is 100%, and the cetylamine yield is 99.1%.
Embodiment 13
In molar ratio for Ni: Co: Cr: Fe: Mo: Cu: Sm=100: 0.01: 3: 4: above-mentioned metal nitrate was made into the aqueous solution that concentration is 0.8mol/L in 2: 1: 0.01, be warming up to 80 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=2, potassium borohydride/metal ion=0.5 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 130 ℃ of reaction temperatures, hydrogen pressure 2.5MPa, 100g3-octadecyl propionitrile, 1.0g catalyst, other adds 5g potash is reaction promoter, low whipping speed is under 500 rev/mins, reacted 80 minutes, 3-octadecyl propionitrile conversion ratio is 100%, N-octadecyl-1, and 3-trimethylene diamines yield is 99%.
Embodiment 14
In molar ratio for Ni: Co: Cu: La=100: above-mentioned metal nitrate was made into the aqueous solution that concentration is 0.5mol/L in 0.05: 10: 0.02, be warming up to 75 ℃ after mixing, stop stirring after under intense stirring condition, adding the hydrazine hydrate formed by hydrazine hydrate/metal ion=3.5, potassium borohydride/metal ion=0.45 proportioning and potassium borohydride co-conducer reaction 5min, be washed to neutrality, be kept in the ethanolic solution after vacuumizing drying.
Use above-mentioned catalyst in the 0.5L autoclave, 110 ℃ of reaction temperatures, hydrogen pressure 2.0MPa, the different tridecane oxygen of 100g 3-base propionitrile, 1.0g catalyst, other adds 1.5g potash is reaction promoter, and low whipping speed is under 500 rev/mins, reacts 90 minutes, the different tridecane oxygen of 3-base propionitrile conversion ratio is 100%, and the different tridecane oxygen of 3-base propylamine yield is 99.2%.
Claims (7)
1, a kind of catalyst of fatty primary amine by fatty nitrile hydrogenation is characterized in that catalyst molar ratio consists of:
Nickel: cobalt: co-catalyst: the aforesaid co-catalyst in rare earth metal=100: 0.01～2.0: 1～15: 0.01～1 be in chromium, iron, copper or the molybdenum one or more
2, the catalyst of a kind of fatty primary amine by fatty nitrile hydrogenation as claimed in claim 1 is characterized in that catalyst molar ratio consists of:
Nickel: cobalt: co-catalyst: rare earth metal=100: 0.01～0.05: 8～11: 0.01～0.05.
3, the Preparation of catalysts method of a kind of fatty primary amine by fatty nitrile hydrogenation as claimed in claim 1 or 2 is characterized in that comprising the steps:
The soluble metallic salt that catalyst is formed is made into the mixed aqueous solution that concentration is 0.1～1mol/L in proportion, be warming up to 60～80 ℃, adding is hydrazine hydrate and the potassium borohydride co-conducer that hydrazine hydrate/metal ion=1～5 and potassium borohydride/metal ion=0.01～0.5 is formed in molar ratio, under 60～80 ℃ of constant temperatures, stir 3-5min and stop heating and stirring, after be washed to neutrality, vacuumizing drying, be kept in the absolute ethyl alcohol.
4, the Preparation of catalysts method of a kind of fatty primary amine by fatty nitrile hydrogenation as claimed in claim 3 is characterized in that described soluble metallic salt is chlorate, sulfate or nitrate.
5, the Application of Catalyst method of a kind of fatty primary amine by fatty nitrile hydrogenation as claimed in claim 1 or 2 is characterized in that comprising the steps:
When fatty primary amine by fatty nitrile hydrogenation, Hydrogen Vapor Pressure is that normal pressure is between the 5.0MPa, reaction temperature is 60～170 ℃, solvent selects ethanol, solvent load is 0～5 times of an Arneel SD raw material quality, it is 0.1%～5% of Arneel SD raw material quality that auxiliary agent is selected from the potash consumption, and catalyst amount is 0.1%～5% of an Arneel SD raw material quality.
6, the Application of Catalyst method of a kind of fatty primary amine by fatty nitrile hydrogenation as claimed in claim 5 is characterized in that described reaction temperature is 110 ℃～130 ℃, and Hydrogen Vapor Pressure is 1.0～2.5MPa.
7, the Application of Catalyst method of a kind of fatty primary amine by fatty nitrile hydrogenation as claimed in claim 5 is characterized in that described Arneel SD is RCN, R-NH-CH
2-CH
2CN, R-O-CH
2-CH
2CN, wherein R=C1～18.
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103965057B (en) * | 2014-04-25 | 2015-12-30 | 浙江普洛医药科技有限公司 | A kind of nitrile prepares the method for primary amine |
| CN113461539B (en) * | 2021-08-02 | 2023-11-21 | 江苏扬农化工集团有限公司 | Method for preparing organic diamine from amino nitrile organic matter |
| CN113651776B (en) * | 2021-08-06 | 2023-10-17 | 中触媒新材料股份有限公司 | Purifying agent for aldehyde impurity-containing compound and application thereof |
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| CN1035284A (en) * | 1988-02-25 | 1989-09-06 | 河南省科学院化学研究所 | The preparation method of fat primary amine |
| CN1088198A (en) * | 1992-04-13 | 1994-06-22 | 恩格尔哈德迪米恩公司 | The preparation method of primary amine and suitable catalyst system thereof |
| CN1215719A (en) * | 1997-09-29 | 1999-05-05 | 巴斯福股份公司 | Preparation of amines |
| CN1359560A (en) * | 1999-07-13 | 2002-07-17 | 三星电子株式会社 | Address generating device for use in multi-stage channel interleaver/deinterleaver |
| US6677486B2 (en) * | 2000-11-16 | 2004-01-13 | Basf Aktiengesellschaft | Hydrogenation of nitriles over Raney catalysts |
| CN1635991A (en) * | 2002-02-23 | 2005-07-06 | 科莱恩有限公司 | Method for the production of primary amines by hydrogenating nitriles |
| CN1792442A (en) * | 2006-01-06 | 2006-06-28 | 中国日用化学工业研究院 | Catalyst for preparing fatty tertiary amine, prepn. method and application thereof |
-
2006
- 2006-12-20 CN CNB200610102303XA patent/CN100435947C/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1035284A (en) * | 1988-02-25 | 1989-09-06 | 河南省科学院化学研究所 | The preparation method of fat primary amine |
| CN1088198A (en) * | 1992-04-13 | 1994-06-22 | 恩格尔哈德迪米恩公司 | The preparation method of primary amine and suitable catalyst system thereof |
| CN1215719A (en) * | 1997-09-29 | 1999-05-05 | 巴斯福股份公司 | Preparation of amines |
| CN1359560A (en) * | 1999-07-13 | 2002-07-17 | 三星电子株式会社 | Address generating device for use in multi-stage channel interleaver/deinterleaver |
| US6677486B2 (en) * | 2000-11-16 | 2004-01-13 | Basf Aktiengesellschaft | Hydrogenation of nitriles over Raney catalysts |
| CN1635991A (en) * | 2002-02-23 | 2005-07-06 | 科莱恩有限公司 | Method for the production of primary amines by hydrogenating nitriles |
| CN1792442A (en) * | 2006-01-06 | 2006-06-28 | 中国日用化学工业研究院 | Catalyst for preparing fatty tertiary amine, prepn. method and application thereof |
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