CN103642047B - A kind of preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine - Google Patents
A kind of preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine Download PDFInfo
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Abstract
The preparation method having invented a kind of double; two (alkyl polyoxy alkane alkene ether) secondary amine, belongs to field of chemical technology.The method is to hold primary amino radical polyoxy alkane alkene monoalky lether (R=C1-C4) for raw material, and Raney's nickel is catalyst, prepares double; two (alkyl polyoxy alkane alkene ether) secondary amine by the condensation of two molecule primary amine-denitrification coupling reaction in atmospheric conditions.The ammonification rate of end primary amino radical polyoxy alkane alkene monoalky lether is 40～100%, catalyst amount is the 0～20% of end primary amino radical polyoxy alkane alkene monoalky lether quality, hydrogen flow rate is every 100g end primary amino radical polyoxy alkane alkene monoalky lether 0～1000ml/min, reaction temperature 150～250 DEG C, reacts 2～20h.The present invention improve secondary amine content when, simplification of flowsheet, reduce cost, enable for industrial circle large-scale production.
Description
Technical field
The preparation method that the present invention relates to a kind of double; two (alkyl polyoxy alkane alkene ether) secondary amine, belongs to field of chemical technology.
Background technology
Amidogen ether compounds (etheramine) is the compound in molecule simultaneously with amido and ehter bond, and its special construction determines it and has the performance of uniqueness.Therefore as a class Functional Chemicals, amidogen ether compounds plays an important role in multiple field such as chemical industry, medicine, over nearly 30 years, the development that amidogen ether is whole world chemical industry is made that huge contribution, especially the polyetheramine (polyetheramine) in this compounds, is widely used in the multiple field of epoxy material, concrete additive, organic pigment, fuel, lube oil additive, plastics, medical material, composite, herbicide and agrochemical.
Comprehensive at present about the report of amine terminated polyether synthetic method, its Research Thinking mainly has two kinds:
The first is set about from the terminal hydroxyl of polyether polyol, replaces its terminal hydroxyl by ammonolysis reaction ammonia (amine) base, and this is also the main method of current amine terminated polyether commercial synthesis；
The active hydrogen from polyether polyol terminal hydroxyl is also had to set about, with easy leaving group or unsaturated group (-NCO ,-NO2,-CN etc.) compound terminate with active hydrogen effect, obtain amine terminated polyether after then passing through corresponding process, this class method includes Hydrolyze method, leaving group method, ammonia phenoxy group method, amino-butenate method, cyanoalkyl method etc..
US Patent No. 2888439 proposes, by amine and the polyether reactant containing leaving group (leavinggroups), to obtain ATPE, and less costly.Its step is first by polyether polyol and phosgene reaction, introduces chloroformate group at polyethers two ends, then reacts with diamine and polyethers chloro-formate.The mol ratio of amido and chloroformate group is 3, just can obtain the ATPE connected by amino-formate bond that viscosity is extremely low.Excessive diamine can as the absorbent of HCl.
It is worthy of note, in the forming process of first step chloro-formate, there may exist the nucleophilic displacement of fluorine side reaction of hydroxyl and chlorine, particularly when in reactant containing dimethylformamide (DMF), side reaction will become main reaction and generate end chloro alkyl, polyether.
Under HCl absorbent exists, end chloro alkyl, polyether can react with aliphatic unary primary amine, obtains the polyethers terminated by secondary amine.
Somebody finds later, and methylsulfonyl group is more more effective leaving group than chlorine, utilizes mesyl chloride that mesyl can introduce the two ends of polyethers easily, and the nucleophilic substitution of methylsulfonyl group and amine also can be well carried out.The synthesis of document polypropylene oxide polyamines, sign and Polyoxypropylene diol, tetrahydrochysene are barked by the toughening effect of epoxy resin is muttered and paratoluensulfonyl chloride puts in four-hole boiling flask, after stirring and dissolving, instills pyridine.Stirring reaction 24h when lower than 30 DEG C, obtains double; two sulfonylation polyethers.Then under nitrogen protection double; two sulfonylation polyethers are instilled in the four-hole boiling flask including ethylenediamine and toluene, at 110 DEG C, carry out aminolysis reaction, obtain lurid polypropylene oxide polyamines.
Chinese patent CN1092786 proposes to prepare amine terminated polyether for polyurethane and epoxy resin for raw material through over-churning, aminating reaction with end hydroxy polyether.In its patent, first end hydroxy polyether is reacted with chloroacetic chloride, benzyl chlorine or Butyltriphenylphosphonium chloride the corresponding ester of generation, then the ester produced is reacted with primary amine, ethylenediamine or trientine etc., generate corresponding amine terminated polyether.
Step of esterification uses polyether polyol and halogenating agent that the polyethers of end chlorine is synthesized, and adds aminating agent and carries out ammonification.After the study on the synthesis phosphorus tribromide of document W Amino Polyoxyalkylene is obtained by reacting the Polyethylene Glycol of bromo in carbon tetrachloride liquid, strong aqua ammonia heats ammonification synthesis ATPE, and determines the ammonification degree of Polyethylene Glycol with infrared spectrum analysis.
Nineteen eighty-two Bayer, the Rasschover et al. of company proposed the TDI prepolymer of polyethers or PEPA by reacting with alkaline aqueous solution, generated containing carbamic intermediate, the method then obtaining amino-compound again.This method it is critical only that first step reaction must carry out under low temperature (18-20 DEG C), to ensure carbamic being completely formed, second step, by raising temperature, makes Amino End Group formic acid radical decomposition, forms amino, and discharges CO2.
US Patent No. 5091582 proposes the method for ammonia phenoxy group (aminophenooy) legal system ATPE.Chloronitrobenzene is under the effect of highly basic (such as NaOH powder) and polar solvent (such as dimethyl sulfoxide), react with polyether polyol, obtain the intermediate product that polyethers is terminated by nitre phenoxy group, then again through hydrogenation reaction, nitre phenoxy compounds is made to be reduced to phenalgin oxo-compound.
US Patent No. 3691112 proposes to utilize amino-butenate (aminocrotonates) method to prepare ATPE, can extremely flexibly select the amino kind at polyethers two ends.First with dienone (diketen) or by the ester exchange reaction of ethyl acetoacetate with polyether polyol, acetoacetate groups is connected at the two ends of polyethers, then with unary primary amine, alkyl alcoholamine or binary primary amine, the polyethers terminated by acetoacetate groups being carried out amination, obtaining end group is the group with imine moiety that amino-butenate, viscosity are very low.
US Patent No. 4061678 polyether polyol carries out additive reaction with propylene cyanogen, then obtains product hydrogenating reduction to amine terminated polyether.
According to molecular weight, number of functional groups, polyether units structure etc., amidogen ether compounds can be divided into multiple series of products:
M-, D-, T-series can be divided in terms of functional group, and titled with molecular weight；Type according to terminal amido has and derives the product that end is secondary amine, titled with S before original series name；The ED product line containing ethylene oxide structure is also derived in chain according to polyether units structure.
Existing product also includes some product lines that some end alkyls are long-chain fat hydrocarbon or aromatic hydrocarbons:
But above-mentioned secondary amine be structurally characterized in that amido one section is connected with polyethers, the other end is ined succession lower alkyl, and this is to be determined by the method preparing amidogen ether at present.According to current existing amidogen ether preparation method, it is impossible to prepare double; two (alkyl polyoxy alkane alkene ether) secondary amine of secondary amine content height, constant product quality, therefore lack double; two (alkyl polyoxy alkane alkene ether) secondary amine in current product line.
Chinese patent CN1629132 provides a kind of with aniline for raw material, utilizes the method that condensation reaction and deamination are coupled to produce diphenylamines, with beta-zeolite molecular sieve for catalyst, and reaction pressure 1.5～3.0MPa, reaction temperature 260～400 DEG C.
The present invention is to hold primary amino radical polyoxy alkane alkene monoalky lether for raw material, double; two (alkyl polyoxy alkane alkene ether) secondary amine is prepared by the condensation of two molecule primary amine-denitrification coupling reaction, but the difference is that the present invention uses hydrogenation/dehydrogenation class catalysis Raney's nickel, reaction condition is normal pressure, reaction temperature only 150～250 DEG C, when improving secondary amine content, simplification of flowsheet, reduction cost, enable for industrial circle large-scale production.
Summary of the invention
The present invention develops one to hold primary amino radical polyoxy alkane alkene monoalky lether for raw material, and Raney's nickel is catalyst, the method preparing pair (alkyl polyoxy alkane alkene ether) secondary amine by the condensation of two molecule primary amine-denitrification coupling reaction in atmospheric conditions.
The technical scheme is that
A kind of preparation method of double, two (alkyl polyoxy alkane alkene ether) secondary amine, it is characterized in that: in end primary amino radical polyoxy alkane alkene monoalky lether, add a certain amount of catalyst, this catalyst is Raney's nickel, described catalyst amount is the 0～20% of end primary amino radical polyoxy alkane alkene monoalky lether quality, hydrogen is passed to the speed of every 100g end primary amino radical polyoxy alkane alkene monoalky lether 0～1000ml/min, it is warming up to 150～250 DEG C, after reaction 2～20h, it is down to room temperature, filter to obtain double, two (the alkyl polyoxy alkane alkene ether) secondary amine of product, the ammonification rate of described end primary amino radical polyoxy alkane alkene monoalky lether is 40～100%.
Described end primary amino radical polyoxy alkane alkene monoalky lether mean molecule quantity is 1000～3000, and its structure is as follows:
Wherein R is the alkyl of carbon number 1～4；R1 is H or CH3, its polyether segment is the single polymers of oxirane, expoxy propane, or both mixed polymers, block polymer；
The ammonification rate of end primary amino radical polyoxy alkane alkene monoalky lether is 60～100%；.When ammonification rate is relatively low, the amine number of product secondary amine can be on the low side, when ammonification rate is higher, can cause the increase of cost of material, and by selecting rational ammonification rate, the product quality index made is stable, cost-effective.
Catalyst is hydrogenation/dehydrogenation class catalyst Raney's nickel, and catalyst amount is the 5～8% of end primary amino radical polyoxy alkane alkene monoalky lether quality.When catalytic amount deficiency, reaction rate is relatively slow, and catalyst excess easily causes waste, and brings pressure can to follow-up filtration.
Reaction temperature is 180～200 DEG C.Temperature is too low, and response speed is relatively slow, is unfavorable for the carrying out of reaction, when temperature is too high, can accelerate the further condensation of secondary amine and generate the speed of tertiary amine so that in product, tertiary amine content raises.
Course of reaction continues pass to a certain amount of hydrogen, hydrogen flow rate every 100g end primary amino radical polyoxy alkane alkene monoalky lether 0～100ml/min.Product colour can be caused deeper when amounts of hydrogen deficiency.
Response time is 6～10h, and the response time is too short, and in product, primary amine content is higher, and the response time is long, then can be that in product, tertiary amine content raises, it is therefore desirable to select the suitable response time.
The thick product of gained of the present invention carries out post processing by the mode of sucking filtration, is connected with vacuum pump through woulfe safety flack with bottle,suction or Witt wide mouthed bottle with buchner funnel, separating catalyst.
Beneficial effect:
The present invention adopts the denitrification coupling reaction of primary amine to prepare secondary amine, and this reaction mechanism is similar to faces hydrogen aminating reaction, therefore has the advantage that side reaction is few, and this reaction condition is normal pressure simultaneously, the shortcoming overcoming again its severe reaction conditions；The present invention, with single reactant end primary amino radical polyoxy alkane alkene monoalky lether for raw material, the production made feeds intake conveniently during operation, simplifies technological process.
Therefore the present invention is when improving secondary amine content, simplification of flowsheet, reduction cost, enables for industrial circle large-scale production.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is expanded on further.
The invention is further illustrated by the following examples, but be not limited to for embodiment.
In an embodiment, secondary amine content (S%) is represented with the ratio of secondary amine value Yu total amine number:
In examination: S% is secondary amine content, %；ASFor the secondary amine value of product, mgKOH/g；A is total amine number of product, mgKOH/g；
End primary amino radical polyoxy alkane alkene monoalky lether raw material used in the present invention is provided by Yangzhou Chenhua New Materials Co., Ltd., and catalyst Raney's nickel is buied from Jiangsu You Lian metallic article company limited.
Example 1:
200g end primary amino radical polyoxy alkane alkene list n-butyl ether, 10g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene list n-butyl ether is 1646, n (EO): n (PO)=3:1, ammonification rate 70%.Pass to hydrogen with the flow velocity of 110ml/min, under the mixing speed of 300r/min, be warming up to 180 DEG C, and react 5h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 52%.
Example 2:
200g end primary amino radical polyoxy alkane alkene list n-butyl ether, 10g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene n-butyl ether is 1646, n (EO): n (PO)=3:1, ammonification rate 70%.Pass to hydrogen with the flow velocity of 100ml/min, under the mixing speed of 300r/min, be warming up to 180 DEG C, and react 5h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 59%.
Example 3:
1000g end primary amino radical polyoxy alkane alkene list n-butyl ether, 30g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 2000ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene list n-butyl ether is 1420, n (EO): n (PO)=3:1, ammonification rate 92%.Pass to hydrogen with the flow velocity of 200ml/min, under the mixing speed of 300r/min, be warming up to 200 DEG C, and react 10h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 54%.
Example 4:
200g end primary amino radical polyoxy alkane alkene list n-butyl ether, 10g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene list n-butyl ether is 1523, n (EO): n (PO)=3:1, ammonification rate 80%.Pass to hydrogen with the flow velocity of 100ml/min, under the mixing speed of 300r/min, be warming up to 200 DEG C, and react 6h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 76%.
Example 5:
200g end primary amino radical polyoxy alkane alkene list n-butyl ether, 10g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene list n-butyl ether is 1646, n (EO): n (PO)=3: 1, ammonification rate 58%.Pass to hydrogen with the flow velocity of 100ml/min, under the mixing speed of 300r/min, be warming up to 180 DEG C, and react 5h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 37%.
Example 6:
200g end primary amino radical polyoxy alkane alkene list n-butyl ether, 10g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene list n-butyl ether is 1646, n (EO): n (PO)=3:1, ammonification rate 58%.Pass to hydrogen with the flow velocity of 125ml/min, under the mixing speed of 300r/min, be warming up to 220 DEG C, and react 5h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 63%.
Example 7:
200g end primary amino radical polyoxy alkane alkene list n-butyl ether, 4g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene list n-butyl ether is 1592, n (EO): n (PO)=3:1, ammonification rate 99%.Pass to hydrogen with the flow velocity of 100ml/min, under the mixing speed of 300r/min, be warming up to 200 DEG C, and react 8h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 58%.
Example 8:
200g end primary amino radical polyoxy alkane alkene list n-butyl ether, 10g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxy alkane alkene list n-butyl ether is 1523, n (EO): n (PO)=3:1, ammonification rate 80%.Pass to hydrogen with the flow velocity of 100ml/min, under the mixing speed of 300r/min, be warming up to 200 DEG C, and react 6h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (normal-butyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 86%.
Example 9:
200g end primary amino radical polyoxypropylene monomethyl ether, 10g catalyst Raney's nickel are joined with agitator, thermometer, ventilation body canal, in the 500ml four-hole boiling flask of condenser west tube, the molecular weight of end primary amino radical polyoxypropylene monomethyl ether is 2050, ammonification rate 99%.Pass to hydrogen with the flow velocity of 100ml/min, under the mixing speed of 300r/min, be warming up to 200 DEG C, and react 6h.
Reaction is cooled to less than 100 DEG C after terminating, and stops logical hydrogen, removes catalyst double; two (methyl polyoxy alkane alkene ether) secondary amine namely by sucking filtration, and secondary amine content (S%) is 76%.
Should be understood that these embodiments are merely to illustrate the present invention rather than restriction the scope of the present invention.In addition, it is to be understood that after having read the content that the present invention lectures, the present invention can be made various changes or modifications by those skilled in the art, and these equivalent form of values fall within the application appended claims limited range equally.
Claims (7)
1. the preparation method of double, two (alkyl polyoxy alkane alkene ether) secondary amine, it is characterized in that: in end primary amino radical polyoxy alkane alkene monoalky lether, add a certain amount of catalyst, this catalyst is Raney's nickel, described catalyst amount is less than the 20% of end primary amino radical polyoxy alkane alkene monoalky lether quality, hydrogen is passed to the speed of every 100g end primary amino radical polyoxy alkane alkene monoalky lether 0～1000mL/min, it is warming up to 150～250 DEG C, after reaction 2～20h, it is down to room temperature, filter to obtain double, two (the alkyl polyoxy alkane alkene ether) secondary amine of product, the ammonification rate of described end primary amino radical polyoxy alkane alkene monoalky lether is 40～100%；Described end primary amino radical polyoxy alkane alkene monoalky lether mean molecule quantity is 1000～3000, and its structure is as follows:
Wherein R is the alkyl of carbon number 1～4；R1For H or CH3, its polyether segment is the single polymers of oxirane, expoxy propane, or both mixed polymers, block polymer；The structural formula of double; two (alkyl polyoxy alkane alkene ether) secondary amine is:
2. the preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine according to claim 1, it is characterised in that: the ammonification rate of end primary amino radical polyoxy alkane alkene monoalky lether is 50～100%.
3. the preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine according to claim 1, it is characterised in that: catalyst is hydrogenation/dehydrogenation class catalyst Raney's nickel, and catalyst amount is the 5～10% of end primary amino radical polyoxy alkane alkene monoalky lether quality.
4. the preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine according to claim 1, it is characterised in that: reaction temperature is 180～220 DEG C.
5. the preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine according to claim 1, it is characterised in that: course of reaction continues pass to a certain amount of hydrogen, hydrogen flow rate every 100g end primary amino radical polyoxy alkane alkene monoalky lether 0～200mL/min.
6. the preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine according to claim 1, it is characterised in that: the response time is 2～10h.
7. the preparation method of double; two (alkyl polyoxy alkane alkene ether) secondary amine according to claim 1, it is characterized in that: product carries out post processing by the mode of sucking filtration, it is connected with vacuum pump through woulfe safety flack with bottle,suction or Witt wide mouthed bottle with buchner funnel, separating catalyst.
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|---|---|---|---|---|
| US3654370A (en) * | 1970-08-28 | 1972-04-04 | Jefferson Chem Co Inc | Process for preparing polyoxyalkylene polyamines |
| CN1546550A (en) * | 2003-12-12 | 2004-11-17 | 江苏省化工研究所有限公司 | Fatty group end-amino polyether production method and special catalyzer preparation method |
| CN1629132A (en) * | 2004-09-03 | 2005-06-22 | 南京工业大学 | Method for preparing diphenylamine by aniline liquid phase condensation and denitrification coupling |
| CN1939890A (en) * | 2006-09-27 | 2007-04-04 | 浙江工业大学 | Production of secondary-amine compound |
| CN102002158A (en) * | 2010-11-10 | 2011-04-06 | 扬州晨化科技集团有限公司 | Preparation method of alkyl amino terminated polyether |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001342163A (en) * | 2000-06-02 | 2001-12-11 | Mitsui Chemicals Inc | Method for producing cyclohexanedione |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3654370A (en) * | 1970-08-28 | 1972-04-04 | Jefferson Chem Co Inc | Process for preparing polyoxyalkylene polyamines |
| CN1546550A (en) * | 2003-12-12 | 2004-11-17 | 江苏省化工研究所有限公司 | Fatty group end-amino polyether production method and special catalyzer preparation method |
| CN1629132A (en) * | 2004-09-03 | 2005-06-22 | 南京工业大学 | Method for preparing diphenylamine by aniline liquid phase condensation and denitrification coupling |
| CN1939890A (en) * | 2006-09-27 | 2007-04-04 | 浙江工业大学 | Production of secondary-amine compound |
| CN102002158A (en) * | 2010-11-10 | 2011-04-06 | 扬州晨化科技集团有限公司 | Preparation method of alkyl amino terminated polyether |
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