CN105542146A - Continuous production process for polyetheramine - Google Patents

Continuous production process for polyetheramine Download PDF

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Publication number
CN105542146A
CN105542146A CN201510908445.4A CN201510908445A CN105542146A CN 105542146 A CN105542146 A CN 105542146A CN 201510908445 A CN201510908445 A CN 201510908445A CN 105542146 A CN105542146 A CN 105542146A
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China
Prior art keywords
polyetheramine
continuous production
reaction
liquefied ammonia
production technology
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Pending
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CN201510908445.4A
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Chinese (zh)
Inventor
宋明贵
颜吉校
金一丰
刘浩
王洪娟
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Zhejiang Huangma Technology Co Ltd
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Zhejiang Huangma Technology Co Ltd
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Priority to CN201510908445.4A priority Critical patent/CN105542146A/en
Publication of CN105542146A publication Critical patent/CN105542146A/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
    • C08G65/3255—Ammonia
    • 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
    • B01J23/84—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 arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/889—Manganese, technetium or rhenium
    • B01J23/8896—Rhenium
    • 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
    • B01J23/84—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 arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/889—Manganese, technetium or rhenium
    • B01J23/8898—Manganese, technetium or rhenium containing also molybdenum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C08G2650/10—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation characterized by the catalyst used in the post-polymerisation functionalisation step

Abstract

The invention relates to a continuous production process for polyetheramine, which belongs to the technical field of organic compounds. The continuous production process comprises the following steps: with polyoxypropylene alcohol, liquefied ammonia and hydrogen as raw materials, continuously conveying the materials into a tubular reactor filled with a catalyst and heated to 150 to 190 DEG C via a material pump for a reaction, wherein reaction pressure is maintained in a range of 4 to 8.0 Mpa; and after completion of the reaction, carrying out rectification twice to collect polyetheramine and recovering excess hydrogen and liquefied ammonia for repeated usage. The continuous production process for polyetheramine can realize continuous feeding and discharging; the retention time of polyether and liquefied ammonia is short; the number of side reactions is small; product stability is high; and production efficiency is improved.

Description

A kind of continuous production technology of polyetheramine
Technical field
The present invention relates to a kind of continuous production technology of polyetheramine, belong to organic compound technical field.
Background technology
Polyetheramine is by polyoxypropylene alcohol and liquefied ammonia under the condition of High Temperature High Pressure, two ends hydroxyl amination and obtaining.Market often it can be used as solidifying agent use, when polyetheramine adds in epoxy resin as Flexible Amine solidifying agent, himself intrinsic structure makes resin system present rigidity to go out curing network and flexible curing network structure, increase snappiness and the elongation at break of epoxy resin, and epoxy resin resistance toheat inherently can be maintained again, greatly increase the performances such as the cohesiveness of epoxy resin, mechanics, electrical isolation, be widely used in national defence.When as RIM polyurethane curing agent, adding of polyetheramine can extend its set time, makes solidifying product more soft and high resilience, and more general many amine curing agents more environmental protection, is extensively used to automotive interior material.When making high concentrations of toluene diisocyanate application of paints, polyetheramine add the snappiness improving coating, make its surface more glossy, color and luster is more firm.In textile printing and dyeing, polyetheramine can improve that nylon fiber material is antistatic, moisture permeability, but does not affect its mechanical strength, and the fabric after making it improve has more level and smooth feel.
At present, the patent of domestic report is mostly adopt interrupter method to prepare polyetheramine, and CN1546550A discloses under Raney's nickel metal catalyst action, prepares polyetheramine by batch reactor reaction, its temperature of reaction is 180 ~ 280 DEG C, and reaction pressure is 13.0 ~ 21.0MPa.CN101982482 discloses under the effect of amorphous alloy catalyst, pass through batch reactor, with polyether glycol synthesizing polyether amine, its catalyzer main component is nickel 40 ~ 50%, aluminium 40 ~ 50%, promotor is one or more in Mo, La, Cr, Mn, and its content is no more than 10%, and the add-on of polyether glycol is 3 ~ 10 times of liquefied ammonia add-on.Reaction pressure 3 ~ 7MPa, temperature of reaction 200 DEG C, severe reaction conditions.
Based on this, make the application.
Summary of the invention
In order to overcome the problems referred to above existed in the synthesis of existing polyetheramine, the invention provides a kind of continuous production technology of polyetheramine.
For achieving the above object, the technical scheme taked of the present invention is as follows:
A kind of continuous production technology of polyetheramine, with polyoxypropylene alcohol, liquefied ammonia, hydrogen for raw material, raw material is sent into catalyzer to be housed and to be warming up in the tubular reactor of 150 ~ 190 DEG C by product pump serialization and is reacted, reaction pressure remains within the scope of 4 ~ 8.0Mpa by the hydrogen of constantly circulation, hydrogen in whole technological process without the need to add, recycle; After completion of the reaction, collect and obtain polyetheramine after twice rectifying, unnecessary hydrogen and liquefied ammonia reclaim to be recycled.
Further, as preferably:
Described catalyzer is with γ-Al 2o 3for carrier, its active ingredient mass ratio is: the combination of any three kinds or more in nickel 5 ~ 15%, cobalt 5 ~ 10%, rhenium 2 ~ 10%, molybdenum 1 ~ 5%, lanthanum 1 ~ 5%.
The feeding rate (mol/min) of described polyoxypropylene alcohol is 1:3 ~ 10 with the ratio of the feeding rate (mol/min) of liquefied ammonia.
Described catalyst activity constituent mass ratio is: nickel 8.5%, cobalt 6.5%, rhenium 3.0%.
Principle of work and the beneficial effect of the application are as follows:
(1) the present invention adopts continuously feeding, discharging, the time that polyoxypropylene alcohol and liquefied ammonia stop in tubular reactor is very short, side reaction is few, product stability is high, production efficiency improves, the degree of wear of catalyzer reduces greatly, and improve the work-ing life of catalyzer, whole production process route is that serialization is carried out; Compared with batch tank high-pressure hydrogenation process, have processing safety high, process control is simple, and the large income of specific investment production capacity is high and operational path is clean rationally meets environmental protection theory, meets the production theory of environmental protection.
(2) production technique of continuously preparing poly ether amine of the present invention, be that the polyoxypropylene alcohol of 200 ~ 3000 is for raw material with molecular weight, reacting by heating under the existence condition of hydrogen, liquefied ammonia and catalyzer: material is sent into by product pump serialization and catalyzer is housed and has been warming up in the shell and tube reactor of 150 ~ 190 DEG C, hydrogen constantly circulates and makes pressure remain within the scope of 4 ~ 8.0Mpa in system, product is collected and is obtained polyetheramine after twice rectifying, unnecessary liquefied ammonia reclaims and recycles, and operational path is rationally clean.
(3) catalyzer in the application is with γ-Al 2o 3for carrier, active ingredient mass ratio is: nickel 5 ~ 15%, cobalt 5 ~ 10%, rhenium 2 ~ 10%, molybdenum 1 ~ 5%, lanthanum 1 ~ 5% three kinds or more, and the preparation technology of catalyzer is simple, with low cost; Meanwhile, in the application, the amount that hydrogen and liquefied ammonia all only need postreaction to consume in system, major part can be applied mechanically repeatedly, and production technique is rationally clean, meets environmental protection theory.
Accompanying drawing explanation
Fig. 1 is amidogen ether serialization synthesis technique schematic flow sheet in the present invention;
Fig. 2 is continuous prodution amidogen ether product process flow figure of the present invention.
Number in the figure: 1. liquid ammonia storage tank; 2. polyoxypropylene alcohol storage tank; 3. volume pump one; 4. volume pump two; 5. preheater; 6. tubular reactor; 7. rectifying tower one; 8. heat exchanger one; 9. surge tank one; 10. well heater; 11. transferpumps; 12. surge tanks two; 13. rectifying tower two; 14. heat exchangers two; 15. surge tanks three; 16. condensing equipments; 17. product transferpumps; 18. product storage tanks.
Embodiment
Embodiment 1
Adopt the production technique of continuously preparing poly ether amine, composition graphs 1 and Fig. 2, liquefied ammonia and polyoxypropylene alcohol are respectively by liquid ammonia storage tank 1, polyoxypropylene alcohol storage tank 2 is supplied, through volume pump 1, after volume pump 24 measures, after the steam preheating of preheater 5, send in tubular reactor 6, catalyzer is filled with in tubular reactor 6, control the feeding rate mol ratio 1:3 ~ 1:10 of polyoxypropylene alcohol storage tank 2 and liquid ammonia storage tank 1, simultaneously hydrogen constantly circulation maintenance system pressure at 4.0 ~ 8.0MPa, temperature of reaction 150 ~ 190 DEG C, after treating catalyzed reaction, intermediate product through product at rectifying tower 1, after rectifying tower 2 13 place completes twice rectifying successively, complete after decompression dehydration and filtration through condensing equipment 16, through product transferpump 17, the polyetheramine of synthesis is sent in product storage tank 18, hydrogen in reaction atmosphere is by surge tank 1, well heater 10, transferpump 11, surge tank 2 12 reclaims cycling and reutilization, liquefied ammonia is then by exchange 2 14, surge tank 3 15 Separation and Recovery cycling and reutilization.
This catalyzer is with γ-Al 2o 3for carrier, its active cost mainly comprises: nickel 5 ~ 15%, cobalt 5 ~ 10%, rhenium 2 ~ 10%, molybdenum 1 ~ 5%, lanthanum 1 ~ 5% three kinds or more; Raw materials used for molecular weight be 200 ~ 3000 polyoxypropylene alcohol, liquefied ammonia, hydrogen, concrete technology Parameter Conditions and effect are in table 1.
The different catalyst system of table 1 is on the impact preparing amidogen ether technique
As can be seen from Table 1, prepare in the technique of amidogen ether, catalyst body is that the amination rate of the polyetheramine of nickel 8.5% cobalt 6.5% rhenium 3.0% is the highest, and although the catalyzer effect of other system is slightly weaker than the catalyst system of nickel 8.5% cobalt 6.5% rhenium 3.0%, the polyetheramine synthesis of 90% amination rate all can be realized.
Embodiment 2
The present embodiment is identical with principle of work with the setting of embodiment 1, and difference is: prepare polyetheramine 1000 effect under different feeds speed processing condition in table 2.
Table 2 different feeds speed is on the impact of amidogen ether technique
As can be seen from Table 2: along with the increase of the feeding rate of liquefied ammonia, amination rate is also with extremely increasing, but after the ratio of speed reaches 1:6, amination rate maintains 97% substantially, therefore in the technique of polyetheramine (M=1000), the ratio of the feeding rate of polyethers and liquefied ammonia is preferably 1:6.
Embodiment 3
The present embodiment is identical with principle of work with the setting of embodiment 1, and difference is: prepare polyetheramine 2000 effect under differential responses temperature process condition in table 3.
Table 3 differential responses temperature is on the impact of amidogen ether technique
As can be seen from Table 3: along with the rising of temperature, amination rate also raises, and after temperature is increased to 180 DEG C, amination rate reaches maximum 98%, therefore to prepare polyetheramine (M=2000) preferable reaction temperature be 180 DEG C.
Embodiment 4
The present embodiment is identical with principle of work with the setting of embodiment 1, and difference is: prepare polyetheramine (M=3000) effect under differential responses temperature process condition in table four.
Table 4 differential responses pressure is on the impact of amidogen ether technique
As can be seen from Table 4: along with the rising of reaction system pressure, amination rate also raises, and after reaction pressure is increased to 6Mpa, amination rate reaches maximum 95%, and integrated equipment and efficiency are considered, select preferred reaction pressure 6Mpa to prepare polyetheramine (M=3000).Above content is the further description done provided technical scheme in conjunction with the preferred implementation of the invention; can not assert that the invention is specifically implemented to be confined to these explanations above-mentioned; for the invention person of an ordinary skill in the technical field; without departing from the concept of the premise of the invention; some simple deduction or replace can also be made, all should be considered as the protection domain belonging to the invention.

Claims (6)

1. the continuous production technology of a polyetheramine, it is characterized in that: with polyoxypropylene alcohol, liquefied ammonia, hydrogen for raw material, raw material is sent into continuously by product pump and is equipped with in the tubular reactor of catalyzer, in this tubular reactor, temperature is 150 ~ 190 DEG C, and reaction pressure remains within the scope of 4 ~ 8.0Mpa; After completion of the reaction, after twice rectifying, obtain polyetheramine, unnecessary hydrogen and liquefied ammonia reclaim to be recycled.
2. the continuous production technology of a kind of polyetheramine as claimed in claim 1, it is characterized in that: described catalyzer is made up of carrier and active ingredient, its active ingredient by mass ratio is: the combination of any three kinds or more in nickel 5 ~ 15%, cobalt 5 ~ 10%, rhenium 2 ~ 10%, molybdenum 1 ~ 5%, lanthanum 1 ~ 5%.
3. the continuous production technology of a kind of polyetheramine as claimed in claim 2, is characterized in that, described catalyst activity constituent mass ratio is: nickel 8.5%, cobalt 6.5%, rhenium 3.0%.
4. the continuous production technology of a kind of polyetheramine as described in claim 1,2 or 3, is characterized in that: described support of the catalyst is γ-Al 2o 3.
5. the continuous production technology of a kind of polyetheramine as claimed in claim 1, is characterized in that: the described input speed of polyoxypropylene alcohol is 1:3 ~ 10 with the ratio of the input speed of liquefied ammonia.
6. the continuous production technology of a kind of polyetheramine as claimed in claim 1, it is characterized in that: liquefied ammonia and polyoxypropylene alcohol are respectively by liquid ammonia storage tank, polyethers storage tank is supplied, through volume pump one, after volume pump two measures, after the steam preheating of preheater, send in tubular reactor, catalyzer is filled with in tubular reactor, the feeding rate mol ratio controlling polyoxypropylene alcohol storage tank and liquid ammonia storage tank is 1:3 ~ 1:10, simultaneously hydrogen constantly circulation maintenance system pressure at 4.0 ~ 8.0MPa, temperature of reaction 150 ~ 190 DEG C, after treating catalyzed reaction, intermediate product through product at rectifying tower one, after rectifying tower two place completes twice rectifying successively, complete after decompression dehydration and filtration through condensing equipment, through product transferpump, the polyetheramine of synthesis is sent in product storage tank, hydrogen in reaction atmosphere is by surge tank one, well heater, transferpump, surge tank two reclaims cycling and reutilization, liquefied ammonia is then by exchange two, surge tank three Separation and Recovery cycling and reutilization.
CN201510908445.4A 2015-12-10 2015-12-10 Continuous production process for polyetheramine Pending CN105542146A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106957420A (en) * 2017-03-30 2017-07-18 浙江皇马表面活性剂研究有限公司 A kind of method that Aethoxy Sklerol direct aminatin prepares polyetheramine
CN109503389A (en) * 2019-01-14 2019-03-22 南京师范大学 The method that primary amine in No. 200 polyetheramines is extracted using unilateral line rectification under vacuum and column chromatography
CN110590577A (en) * 2019-09-25 2019-12-20 山东省化工研究院 Device and method for continuously synthesizing ester quaternary ammonium compound
CN111218247A (en) * 2020-03-24 2020-06-02 Tcl华星光电技术有限公司 Frame glue material and liquid crystal display panel

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CN102336903A (en) * 2011-07-07 2012-02-01 中国石油化工集团公司 Production process of aliphatic polyetheramine
CN102634006A (en) * 2012-03-28 2012-08-15 浙江皇马科技股份有限公司 Polyether amine for textile printing and dyeing auxiliary and preparation method for polyether amine
CN103145974A (en) * 2011-12-06 2013-06-12 中国科学院大连化学物理研究所 Method of preparing primary amine by ammonification of alcoholic hydroxyl group
CN104119239A (en) * 2014-08-12 2014-10-29 无锡阿科力科技股份有限公司 Process of producing small molecular weight polyether amine by continuous method
CN104419002A (en) * 2013-08-20 2015-03-18 中国石油化工股份有限公司 Producing method of amine-terminated polyether
CN104693434A (en) * 2015-03-04 2015-06-10 扬州晨化新材料股份有限公司 Production method for continuously synthesizing polyether amine through static bed

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5003107A (en) * 1989-12-18 1991-03-26 Texaco Chemical Company Catalytic method for the reductive amination of poly(oxytetramethyle) glycols
CN101982482A (en) * 2010-10-29 2011-03-02 江苏钟山化工有限公司 Method for preparing polyether amine by adopting amorphous alloy catalyst
CN102336903A (en) * 2011-07-07 2012-02-01 中国石油化工集团公司 Production process of aliphatic polyetheramine
CN103145974A (en) * 2011-12-06 2013-06-12 中国科学院大连化学物理研究所 Method of preparing primary amine by ammonification of alcoholic hydroxyl group
CN102634006A (en) * 2012-03-28 2012-08-15 浙江皇马科技股份有限公司 Polyether amine for textile printing and dyeing auxiliary and preparation method for polyether amine
CN104419002A (en) * 2013-08-20 2015-03-18 中国石油化工股份有限公司 Producing method of amine-terminated polyether
CN104119239A (en) * 2014-08-12 2014-10-29 无锡阿科力科技股份有限公司 Process of producing small molecular weight polyether amine by continuous method
CN104693434A (en) * 2015-03-04 2015-06-10 扬州晨化新材料股份有限公司 Production method for continuously synthesizing polyether amine through static bed

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106957420A (en) * 2017-03-30 2017-07-18 浙江皇马表面活性剂研究有限公司 A kind of method that Aethoxy Sklerol direct aminatin prepares polyetheramine
CN109503389A (en) * 2019-01-14 2019-03-22 南京师范大学 The method that primary amine in No. 200 polyetheramines is extracted using unilateral line rectification under vacuum and column chromatography
CN109503389B (en) * 2019-01-14 2021-08-31 南京师范大学 Method for extracting primary amine in No. 200 polyetheramine by adopting single-side-line reduced pressure rectification and column chromatography
CN110590577A (en) * 2019-09-25 2019-12-20 山东省化工研究院 Device and method for continuously synthesizing ester quaternary ammonium compound
CN111218247A (en) * 2020-03-24 2020-06-02 Tcl华星光电技术有限公司 Frame glue material and liquid crystal display panel

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