CN102633647A - Environment-friendly preparation method of tert-butylamine - Google Patents
Environment-friendly preparation method of tert-butylamine Download PDFInfo
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- CN102633647A CN102633647A CN2012100844877A CN201210084487A CN102633647A CN 102633647 A CN102633647 A CN 102633647A CN 2012100844877 A CN2012100844877 A CN 2012100844877A CN 201210084487 A CN201210084487 A CN 201210084487A CN 102633647 A CN102633647 A CN 102633647A
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Abstract
The invention discloses an environment-friendly preparation method of tert-butylamine. Isobutylene and liquid ammonia are directly subjected to amination under the action of a catalyst to prepare the tert-butylamine. The catalyst uses a Y-type zeolite molecular sieve as the matrix, and the active component elements and modifying elements account for 10-30%. The Y-type zeolite molecular sieve is modified by the following steps: exchanging the Y-type zeolite molecular sieves with an NH4Cl aqueous solution, washing, drying in a nitrogen or argon atmosphere, and carrying out heat treatment by roasting to obtain an H-type zeolite molecular sieve; and carrying out dipping treatment on the H-type molecular sieve with metal salt, drying in a nitrogen or argon atmosphere, roasting to obtain the modified Y-type zeolite molecular sieve. The modified Y-type zeolite molecular sieve catalyst must be activated before use. The invention has the advantages of mild reaction conditions, high selectivity, high yield, environment friendliness and low catalyst modifying cost, and is suitable for industrial production.
Description
Technical field
The present invention relates to a kind of preparation method of TERTIARY BUTYL AMINE, say that more specifically a kind of isobutene aminating legal system is equipped with the method for TERTIARY BUTYL AMINE, belong to chemosynthesis technical field.
Background technology
TERTIARY BUTYL AMINE is widely used in flat synthetic of welfare, viton accelerator NS, pharmacy sterilant and dye coloring agent.TERTIARY BUTYL AMINE made in 1985 first, along with the increase of TERTIARY BUTYL AMINE market demand, had developed the compound method of tens of kinds TERTIARY BUTYL AMINE for many years, can realize that industrialized method mainly contains tert-butylalcohol method, iso-butylene-HCN method, MTBE-HCN, iso-butylene ammoniation process.Wherein, mainly there is following shortcoming in the technology method of the synthetic TERTIARY BUTYL AMINE of first three tradition: tert-butylalcohol method arts demand uses a large amount of strong acid and strong bases, and is serious and environmental pollution is big to equipment corrosion.The HCN that uses in iso-butylene-HCN method receive very big restriction and toxicity very big.The MTBE-HCN legal system is equipped with TERTIARY BUTYL AMINE also need use highly toxic product HCN, and has by product such as methyl-formiate to generate, and separating difficulty is bigger.
Existing iso-butylene ammoniation process prepares TERTIARY BUTYL AMINE, is raw material with iso-butylene and liquefied ammonia, under catalyst action, under certain temperature, pressure, input speed, reacts, and can directly prepare TERTIARY BUTYL AMINE, and atom utilization can reach 100%.In the above-mentioned reaction, require temperature of reaction up to 350 ℃ in the early stage technology, reaction pressure has very high requirement up to 30Mpa to equipment, and power and energy consumption is big.Along with the improvement to catalyzer, the reaction pressure of isobutene aminating obviously descends to some extent.For example, U.S. Pat 5648546 is reported employing Y-type zeolite (HZSM-5) as the Preparation of Catalyst TERTIARY BUTYL AMINE, and required temperature is 300 ℃, and pressure is 20Mpa, and the yield of TERTIARY BUTYL AMINE can reach 11.95%.Mainly adopted the Ru of precious metal in the patent, Os, one or more among Pb or the Pt have carried out modification to Y-type zeolite.To the modification of catalyzer, make the condition of reaction make moderate progress, but catalyzer uses a large amount of precious metals in the above-mentioned reaction, the unit cost of production increases greatly, is unfavorable for suitability for industrialized production.
Summary of the invention
To the problems referred to above, the problem that quasi-solution of the present invention is determined provides that a kind of reaction conditions is gentle relatively, the selectivity of reaction and yield is higher and the cheap relatively preparation TERTIARY BUTYL AMINE method of Preparation of Catalyst cost used.This method relatively is fit to suitability for industrialized production through practical proof.
For achieving the above object, the present invention has adopted following technical scheme: a kind of environmentally friendly method for preparing TERTIARY BUTYL AMINE makes TERTIARY BUTYL AMINE by iso-butylene and liquefied ammonia direct amination under the effect of catalyzer; Its temperature of reaction is 180～270 ℃, and reaction pressure is at 0.1～1.0Mpa, and the ratio of liquefied ammonia and iso-butylene is at 1.2:1～2.0:1; Define with iso-butylene; Input speed is 10～210g/h, and said catalyzer is a parent with Y-type zeolite molecular sieve, SiO in the said Y-type zeolite molecular sieve
2/ Al
2O
3>=4.8, said Y-type zeolite molecules mesh size is 0.1～1.0nm, and the silica alumina ratio of said Y-type zeolite molecular sieve is 10～50, and the specific surface area of said Y-type zeolite molecular sieve is at 500～850m
2/ g, 70～90% of the shared catalyzer of Y-shaped molecular sieve, its activeconstituents element and modifying element account for 10-30%;
Said Y-type zeolite molecular sieve is handled through following modification:
A) earlier with above-mentioned Y-type zeolite molecular sieve NH
4The exchange of the Cl aqueous solution, washing detect to the Silver Nitrate with the 0.01mol/L for preparing in advance exceeds, after carrying out drying, roasting under the atmosphere of nitrogen or argon gas, obtains then H-type zeolite molecular sieve less than the existence of cl ions; Said NH
4Cl aqueous solution mass percentage concentration is 3～4%;
B) then H-type molecular sieve with metal-salt dip treating 10～20 hours; And under the atmosphere of nitrogen or argon gas, carry out the Y-type zeolite molecular sieve that drying, roasting can obtain modification; The percentage concentration of said metal-salt is 8-76%; Said metal-salt is any one or a two or more mixture of highly basic metal-salt, heavy metallic salt, rare earth metal salt, in the said Y-type zeolite molecular sieve in the metal in the metal-salt, its quality percentage composition 1～9%;
C) the Y-type zeolite [molecular sieve of modification need carry out activation before use, in the presence of nitrogen, argon gas or other mixed gass, is 100～500 ℃ in temperature promptly, and pressure-controlling is activation 20～60h under 0.01～0.5Mpa.
Said an alkali metal salt is saltpetre or SODIUMNITRATE; Said heavy metallic salt is an iron nitrate, and rare earth metal salt is cadmium carbonate or nitric acid molybdenum or Lanthanum trinitrate.
Because adopt technique scheme: what selected for use in the patent of the present invention is with the parent of Y-type zeolite as catalyzer; And through overbased metal; Alkaline rare earth metal, one or more in heavy metal or the precious metal carry out modification, and the gained catalyzer can use through after the simple activation again.It is simple and convenient to prepare this catalyzer, and catalyzer is longer work-ing life.Simultaneously, use the TERTIARY BUTYL AMINE temperature of reaction of this Preparation of Catalyst lower, reaction pressure is near normal pressure, and conversion for isobutene can reach 11.6%, and the selectivity of TERTIARY BUTYL AMINE is near 100%.Compared with prior art; The Preparation of Catalyst raw material that the present invention selected for use all is easy to get and low price; Preparation technology is simple; Not only catalytic activity is high, long service life to handle the catalyzer obtain through modification, and with prepare with class methods that TERTIARY BUTYL AMINE is compared its selectivity and per pass conversion has significantly improved.Compare with the Preparation of Catalyst TERTIARY BUTYL AMINE that relates among the patent US5648546; Adopt the Catalyst Production TERTIARY BUTYL AMINE of the inventive method preparation; Reaction conditions gentleness, selectivity and transformation efficiency relatively is high, and particularly the Preparation of Catalyst cost reduces greatly, relatively is fit to suitability for industrialized production.
In addition; The present invention's favourable this thought of low temperature amination process on thermodynamics; Through the Si/Al proportioning of regulating catalyst, add aforesaid methods such as active ingredient, the acid matter on modulation molecular sieve surface; Make it the absorption and the desorb of reactant and product are formed good coupling the active solid acid catalyst of structure tool low temperature amination.The exploitation of low-temperature catalyzed amination operational path is to realize that alkene, the direct amination of aromatic hydrocarbons are shaped on the basis of machine aminate.Low temperature amination reaction with the direct amination system TERTIARY BUTYL AMINE of iso-butylene is a target, for alkene, the direct aminating environmentally friendly operational path of aromatic hydrocarbons provide theory and experimental basis.
Embodiment
A kind ofly be used for the catalyzer that the direct amination of iso-butylene prepares TERTIARY BUTYL AMINE: as parent, the aperture is 0.1～1.0nm to this catalyzer with Y-type zeolite, and the silica alumina ratio of molecular sieve is 10～50, and specific surface area is 500～850m
2/ g.The modification of molecular sieve elder generation becomes the H-molecular sieve, and then for improving activity of such catalysts and life-span, we have selected for use in highly basic metal, heavy metal, the rare earth metal one or more that catalyzer has been carried out modification.Modifying element content in the catalyzer is 1～9%.
The preparation process of recommending is following:
With Y-type zeolite and γ-Al
2O
3Mixed grinding is even, tackiness agent γ-Al
2O
3Consumption be 10-50% (wt.).Add 5% (wt.) HNO
3The mud shape that the aqueous solution grinds, extrusion molding, the moulding after drying, roasting obtains Y-property zeolite [molecular sieve.
Then above-mentioned catalyzer is used the NH of mass percentage concentration as 3-4%
4Cl aqueous solution exchange (NH
4Cl aqueous solution mass percentage concentration may be selected to be 3%, 3.54%, 4% etc.), washing, drying and roasting obtain required H-type molecular sieve.
H-type molecular sieve can obtain the Y-type zeolite catalyst of modification with the metal-salt dip treating.
The Y-type zeolite catalyst of gained modification need carry out activation before use; Promptly in the presence of nitrogen, argon gas or other mixed gass, be that 100～500 ℃ (can select 100 ℃, 200 ℃, 300 ℃, 400 ℃, 500 ℃ etc.), pressure-controlling are in 0.01-0.5Mpa (can select 0.01Mpa, 0.5Mpa, 0.05Mpa, 0.08Mpa etc.) activation 20～60 hours (may command 20h, 30h, 40h, 50h, 60h) down in temperature.Within 24 hours, use this activity of such catalysts the highest.
Utilize above-mentioned prepared catalyzer; By the direct amination system TERTIARY BUTYL AMINE of iso-butylene: temperature of reaction is 180～270 ℃; Reaction pressure is 0.1～1.0Mpa, and the mol ratio of liquefied ammonia and iso-butylene is 1.2:1～2.0:1, with iso-butylene define, input speed is 10～210g/ h.
The raw material iso-butylene of being selected for use in the reaction can be that purity is higher, also can be that the carbon four behind the extracting divinyl mixes gas, and liquefied ammonia is getting final product of technical grade.
Preparation of catalysts
Get the former powder (SiO of Y-type zeolite molecular sieve
2/ Al
2O
3>=4.8, the aperture is that the silica alumina ratio of 0.1～1.0nm, molecular sieve is 10～50, specific surface area is 500～850m
2/ g) with tackiness agent γ-Al
2O
3Mixed grinding is even, tackiness agent γ-Al
2O
3Consumption be 10～50% (wt.).Add 5% (wt.) HNO
3The mud shape that the aqueous solution grinds, extrusion molding 300～500 ℃ of following roastings 2～10 hours, can obtain Y-type zeolite molecular sieve behind the moulding after drying.
Then above-mentioned Y-type zeolite [molecular sieve is used NH
4Cl aqueous solution exchange, washing to pre-configured silver nitrate solution detection less than the existence of cl ions, under the atmosphere of nitrogen or argon gas, carry out drying then, roasting can obtain H-type zeolite molecular sieve.H-type molecular sieve carries out the Y-type zeolite molecular sieve that drying, roasting can obtain modification with above-mentioned one or more metal-salt dip treating that are mentioned to 10～20 hours (can select 10 hours, 15 hours, 20 hours etc.) back under the atmosphere of nitrogen or argon gas.
Each embodiment specifically is used to exchange material and finished catalyst modifying element and the content thereof of modification and sees table 1.
Table 1.
| Embodiment | Raw material is used in modification | Modifying element | Modifying element content (wt.%) |
| Embodiment 1 | 8% saltpetre, 15% iron nitrate | K、Fe | Be respectively 1%, 2% |
| Embodiment 2 | 16% saltpetre, 20% iron nitrate | K、Fe | Be respectively 2%, 3% |
| Embodiment 3 | 16% saltpetre, 76% cadmium carbonate | K、Cr | Be respectively 2%, 8% |
| Embodiment 4 | 80% cadmium carbonate | Cr | 9% |
| Embodiment 5 | 16% saltpetre, 76% nitric acid molybdenum | K、Mo | Be respectively 4%, 6% |
| Embodiment 6 | 60% nitric acid molybdenum | Mo | 8% |
| Embodiment 7 | 16% Lanthanum trinitrate | Ce | 4% |
| Embodiment 8 | 8% saltpetre, 45% Lanthanum trinitrate | K、Mo | Be respectively 2%, 6% |
The preparation of TERTIARY BUTYL AMINE
In the stainless steel reactor of Φ 600*3000mm, (air speed is 400h to catalyzer at 300 ℃, nitrogen or argon gas with the y-type zeolite catalyst loading of above-mentioned preparation
-1) pre-treatment 10h, control the mol ratio of suitable reaction temperature, reaction pressure, iso-butylene air speed and iso-butylene and liquid amine well.Iso-butylene and ammonia are adjusted to required flow through under meter respectively, behind surge tank, preheater, interchanger, get into reactor drum.Reacted gas; After interchanger and cold burden carry out heat exchange, get into the ammonia rectifying tower, recovered overhead ammonia gets into the recycle system, and tower still gas mixture is carried and got into the iso-butylene regenerating column; The cat head iso-butylene gets into the recycle system, and tower still TERTIARY BUTYL AMINE entering rectifying tower is refining can to obtain desired product.Experimental data is connected on the analysis of line gas chromatographic detection through thief hole and obtains.Reaction process condition that each instance enforcement is concrete and result thereof are referring to table 2.
Table 2.
| Embodiment | Temperature of reaction (℃) | Reaction pressure (Mpa) | Liquefied ammonia/iso-butylene (mol ratio) | Define input speed (g/h) with iso-butylene | Isobutene conversion (%) | TERTIARY BUTYL AMINE selectivity (%) |
| Embodiment 1 | 180 | 0.1 | 1.2:1 | 150 | 3.4 | 100 |
| Embodiment 2 | 210 | 0.1 | 1.5:1 | 210 | 3.0 | 100 |
| Embodiment 3 | 190 | 0.1 | 1.8:1 | 110 | 6.0 | 100 |
| Embodiment 4 | 220 | 0.1 | 2.0:1 | 90 | 6.5 | 100 |
| Embodiment 5 | 230 | 0.1 | 1.3:1. | 10 | 6.8 | 100 |
| Embodiment 6 | 250 | 0.2 | 1.7:1 | 21 | 11.6 | 100 |
| Embodiment 7 | 240 | 0.2 | 1.6:1 | 50 | 10.2 | 100 |
| Embodiment 8 | 270 | 0.2 | 1.4:1 | 70 | 8.5 | 100 |
Claims (2)
1. an environmentally friendly method for preparing TERTIARY BUTYL AMINE makes TERTIARY BUTYL AMINE by iso-butylene and liquefied ammonia direct amination under the effect of catalyzer, it is characterized in that its temperature of reaction is 180～270 ℃; Reaction pressure is at 0.1～1.0Mpa; The ratio of liquefied ammonia and iso-butylene is 1.2:1-2.0:1, defines with iso-butylene, and input speed is 10～210g/h; Said catalyzer is a parent with Y-type zeolite molecular sieve, SiO in the said Y-type zeolite molecular sieve
2/ Al
2O
3>=4.8, said Y-type zeolite molecules mesh size is 0.1～1.0nm, and the silica alumina ratio of said Y-type zeolite molecular sieve is 10～50, and the specific surface area of said Y-type zeolite molecular sieve is 500-850m
2/ g, 70～90% of the shared catalyzer of Y-shaped molecular sieve, its activeconstituents element and modifying element account for 10～30%;
Said Y-type zeolite molecular sieve is handled through following modification:
A) earlier with above-mentioned Y-type zeolite molecular sieve NH
4Cl aqueous solution exchange, washing to Silver Nitrate with the 0.01mol/L for preparing in advance detect less than the existence of cl ions exceed, under the atmosphere of nitrogen or argon gas, carry out drying then, roasting can obtain H-type zeolite molecular sieve; Said NH
4Cl aqueous solution mass percentage concentration is 3～4%;
B) then H-type molecular sieve with metal-salt dip treating 10～20 hours; And under the atmosphere of nitrogen or argon gas, carry out the Y-type zeolite molecular sieve that drying, roasting can obtain modification; The percentage concentration of said metal-salt is 8～76%; Said metal-salt is any one or a two or more mixture of highly basic metal-salt, heavy metallic salt, rare earth metal salt, is 1～9% in the metal in the metal-salt, its quality percentage composition in the said Y-type zeolite molecular sieve;
C) the Y-type zeolite [molecular sieve of modification need carry out activation before use, in the presence of nitrogen, argon gas or other mixed gass, is 100～500 ℃ in temperature promptly, and pressure-controlling is activation 20-60h under 0.01-0.5Mpa.
2. the environmentally friendly method for preparing TERTIARY BUTYL AMINE according to claim 1 is characterized in that said an alkali metal salt is saltpetre or SODIUMNITRATE; Said heavy metallic salt is an iron nitrate, and rare earth metal salt is cadmium carbonate or nitric acid molybdenum or Lanthanum trinitrate.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107486236A (en) * | 2016-06-13 | 2017-12-19 | 中国科学院大连化学物理研究所 | A kind of catalyst for producing the propylamine of 2 methyl 2 and its preparation method and application |
| CN107899605A (en) * | 2017-11-22 | 2018-04-13 | 山东玉皇化工有限公司 | It is a kind of to be used to catalyze and synthesize catalyst of tert-butylamine and preparation method thereof |
| CN108067293A (en) * | 2016-11-08 | 2018-05-25 | 中国科学院大连化学物理研究所 | A kind of catalyst and preparation method of metering system amination production 2- methyl -2- propylamine |
| CN108654594A (en) * | 2017-03-27 | 2018-10-16 | 万华化学集团股份有限公司 | A kind of solid acid catalyst and preparation method thereof and purposes |
| CN112745223A (en) * | 2019-10-31 | 2021-05-04 | 中国石油化工股份有限公司 | Process for preparing tert-butylamine |
| CN114436853A (en) * | 2020-10-31 | 2022-05-06 | 中国石油化工股份有限公司 | Method for preparing tert-butylamine by amination of isobutene |
| CN114736125A (en) * | 2022-04-27 | 2022-07-12 | 浙江皇马科技股份有限公司 | Method for preparing tert-butylamine through direct amination of isobutene at lower temperature |
| CN115254181A (en) * | 2022-09-28 | 2022-11-01 | 淄博鲁华泓锦新材料集团股份有限公司 | Catalyst for producing tert-butylamine and preparation method and application thereof |
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| CN107486236A (en) * | 2016-06-13 | 2017-12-19 | 中国科学院大连化学物理研究所 | A kind of catalyst for producing the propylamine of 2 methyl 2 and its preparation method and application |
| CN108067293B (en) * | 2016-11-08 | 2021-01-29 | 中国科学院大连化学物理研究所 | Catalyst for producing 2-methyl-2-propylamine by amination of methyl propylene and preparation method thereof |
| CN108067293A (en) * | 2016-11-08 | 2018-05-25 | 中国科学院大连化学物理研究所 | A kind of catalyst and preparation method of metering system amination production 2- methyl -2- propylamine |
| CN108654594A (en) * | 2017-03-27 | 2018-10-16 | 万华化学集团股份有限公司 | A kind of solid acid catalyst and preparation method thereof and purposes |
| CN108654594B (en) * | 2017-03-27 | 2021-01-29 | 万华化学集团股份有限公司 | Solid acid catalyst, preparation method and application thereof |
| CN107899605A (en) * | 2017-11-22 | 2018-04-13 | 山东玉皇化工有限公司 | It is a kind of to be used to catalyze and synthesize catalyst of tert-butylamine and preparation method thereof |
| CN112745223A (en) * | 2019-10-31 | 2021-05-04 | 中国石油化工股份有限公司 | Process for preparing tert-butylamine |
| CN112745223B (en) * | 2019-10-31 | 2022-08-12 | 中国石油化工股份有限公司 | Process for preparing tert-butylamine |
| CN114436853A (en) * | 2020-10-31 | 2022-05-06 | 中国石油化工股份有限公司 | Method for preparing tert-butylamine by amination of isobutene |
| CN114736125A (en) * | 2022-04-27 | 2022-07-12 | 浙江皇马科技股份有限公司 | Method for preparing tert-butylamine through direct amination of isobutene at lower temperature |
| CN114736125B (en) * | 2022-04-27 | 2024-01-02 | 浙江皇马科技股份有限公司 | Method for preparing tert-butylamine by direct amination of isobutene at lower temperature |
| CN115254181A (en) * | 2022-09-28 | 2022-11-01 | 淄博鲁华泓锦新材料集团股份有限公司 | Catalyst for producing tert-butylamine and preparation method and application thereof |
| CN115254181B (en) * | 2022-09-28 | 2023-01-06 | 淄博鲁华泓锦新材料集团股份有限公司 | Method for producing tert-butylamine |
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Application publication date: 20120815 |