CN107216273B - A kind of method that transfer hydrogenation method prepares amino naphthol sulfonic acid - Google Patents
A kind of method that transfer hydrogenation method prepares amino naphthol sulfonic acid Download PDFInfo
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- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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Abstract
The present invention provides a kind of method that transfer hydrogenation method prepares amino naphthol sulfonic acid, and this method is that nitroso or nitronaphthol sulfonic acid are carried out transfer hydrogenation reduction to prepare amino naphthol sulfonic acid；The preparation method is the following steps are included: S110: sequentially adding nitroso or nitronaphthol sulfonic acid, atent solvent, catalyst and hydrogen source in reaction vessel, transfer hydrogenation reduction reaction, 0.5~10h of hydrogenation reaction time are carried out at -20~120 DEG C；S120: being separated by solid-liquid separation after fully reacting, after the liquid concentration isolated, carries out amino naphthol sulfonic acid needed for obtaining after acidification is separated with product.It is easy that transfer hydrogenation method prepares amino naphthol sulfonic acid technological operation, good product quality obtains product after being separated by filtration catalyst after the reaction was completed, and catalysts and solvents can be recycled through simple process, pollution problem is avoided, is a kind of environmentally friendly green production process.
Description
Technical field
The present invention relates to technical field of organic synthesis, and in particular to a kind of transfer hydrogenation method prepares the side of amino naphthol sulfonic acid
Method.
Background technique
2- amino -1-naphthol-5-sulfonic acid and 2- amino-Neville acid are to prepare 2- diazonium -1- naphthoquinones -5- sulphonyl
The intermediate of chlorine and 2- diazonium -1- naphthoquinones -4- sulfonic acid chloride.2- diazonium -1- naphthoquinones -5- sulfonic acid chloride and 2- diazonium -1- naphthoquinones -4- sulphur
Acyl chlorides is mainly used for the light sensitive layer of pre-coating sensitive lithographic (abbreviation PS editions) and the photoresist of integrated circuit, printed circuit, external
Also exploitation is for household appliances, toleware, precision machinery drawing, color TV, solarization mutually duplication, photosensitive ink etc. again.
2- amino -1-naphthol-5-sulfonic acid is prepared in the prior art and 2- amino-Neville acid is using sodium hydrosulfite
The process of nitroso or nitro is restored with hydrochloric acid.Such method is seriously polluted, generates a large amount of waste residue and waste liquid, seriously
Environment is polluted, there are a large amount of environmental issues.
Invention (Publication No.: CN105777588A) filed in applicant of the present invention on April 2nd, 2016, discloses
" a kind of method that catalytic hydrogenation prepares amino naphthol sulfonic acid ", using hydrogen as hydrogen source in the preparation method of the disclosure of the invention,
And hydrogen needs dedicated equipment (autoclave) and corresponding safety measure, preparation condition is harsh, complex process.
Summary of the invention
It is dirty in order to overcome corrosion She Bei ﹑ technological operation Fan Za ﹑ existing for existing sodium hydrosulfite reducing process to generate a large amount of waste residues
The problem of contaminating environment, and need when use catalytic hydrogenation using special equipment, while the problem of preparation condition harshness, this hair
It is bright to be designed to provide a kind of method that transfer hydrogenation method prepares amino naphthol sulfonic acid, this method be under the action of catalyst,
Using transfer hydrogenation reduction reaction, this green reducing process prepares amino naphthol sulfonic acid, and wherein nitroso or nitro are in naphthols knot
Position in structure is 2 or 4, and position of the sulfonic group in naphthols is 5 or 4.The reaction condition of this method is relatively warm
Be suitable for industrialized production.
To achieve the above object, technical scheme is as follows:
A kind of method that transfer hydrogenation method prepares amino naphthol sulfonic acid, this method be by nitroso or nitronaphthol sulfonic acid into
Row transfer hydrogenation reduction prepares amino naphthol sulfonic acid；
The preparation method the following steps are included:
S110: sequentially adding nitroso or nitronaphthol sulfonic acid, atent solvent, catalyst and hydrogen source in reaction vessel,
Transfer hydrogenation reduction reaction, 0.5~10h of hydrogenation reaction time are carried out at -20~120 DEG C；
S120: being separated by solid-liquid separation after fully reacting, after the liquid concentration isolated, obtain after acidification is separated with product
Amino naphthol sulfonic acid needed for obtaining.
Further, the hydrogen source includes hydrazine hydrate, anhydrous hydrazine or ammonium formate；
The usage amount for seemingly stating hydrogen source is 0.5~5 times of amount of nitroso or nitronaphthol sulfonic acid species.
Further, the additional amount of the atent solvent is 0.5~20 that nitroso or nitronaphthol sulfonic acid weight is added
Times；
The additional amount of the catalyst is 0.5%~20% that nitroso or nitronaphthol sulfonic acid weight is added.
Further, after the separation of solid and liquid, defeated time reaction system continues to use the solid catalyst isolated again.
Further, the catalyst is the catalyst of metal or metal oxide or Metal Supported；
The metal is Raney's nickel, Pt/C or Pd/C；
Wherein: nickel content is 40~60wt.% in the Raney's nickel catalyst, in Pt/C catalyst Pt content be 0.5~
Pd content is 0.5~10wt.% in 5wt.%, Pd/C catalyst；
The metal oxide include iron oxide and with iron oxide similar catalyst.
Further, when the catalyst is Raney's nickel, the additional amount of Raney's nickel is that nitroso or nitronaphthol sulphur is added
The 1%~10% of sour weight；In the transfer hydrogenation reduction reaction, reaction temperature -20~120 DEG C, 0.5~10h of reaction time.
Further, when the catalyst is Pt/C, the additional amount of Pt/C is that nitroso or nitronaphthol sulfonic acid weight is added
The 0.1%~10% of amount, in the transfer hydrogenation reduction reaction, reaction temperature -20~120 DEG C, 0.5~10h of reaction time.
Further, when the catalyst is Pd/C, the additional amount of Pd/C is that nitroso or nitronaphthol sulfonic acid weight is added
The 0.1%~10% of amount, in the transfer hydrogenation reduction reaction, reaction temperature -20~120 DEG C, 0.5~10h of reaction time.
Further, the atent solvent include alcohols solvent and/or halogenated hydrocarbon, arene, ethers and esters with
And at least one of N,N-dimethylformamide, dimethylsulfoxide solvent；
The alcohols solvent includes methanol, ethyl alcohol or isopropanol.
Further, in amino naphthol sulfonic acid prepared by this method, the position of raw material nitroso or nitro in naphthols
It is 2 or 4, position of the sulfonic group in naphthols is 5 or 4.
The method for preparing amino naphthol sulfonic acid using transfer hydrogenation method provided by the invention, has the advantage that transfer hydrogen
Change method prepares amino naphthol sulfonic acid new process and sodium hydrosulfite or iron powder reducing nitroso or nitronaphthol sulfonic acid prepares aminonaphthol
Sulfonic acid common process is compared, and technological operation that the present invention develops is easy, and reaction condition is mild, without being added water, good product quality,
Product is obtained after being separated by filtration catalyst after the reaction was completed, catalysts and solvents can be recycled through simple process, avoid
Pollution problem, is a kind of environmentally friendly green production process.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described, it should be apparent that, the accompanying drawings in the following description is this hair
Bright some embodiments for those of ordinary skill in the art without any creative labor, can be with
It obtains other drawings based on these drawings.
Fig. 1 is the HPLC map of 1- naphthols -2- amino -5- sulfonic acid prepared by embodiment 1.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention
In attached drawing, technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is
A part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art
Every other embodiment obtained without creative efforts, shall fall within the protection scope of the present invention.
The present invention provides a kind of method that transfer hydrogenation method prepares amino naphthol sulfonic acid, and this method is by nitroso or nitro
Naphtholsulfonic acid carries out transfer hydrogenation method and prepares amino naphthol sulfonic acid, this method detailed process are as follows: first in reaction vessel successively
Nitroso or nitronaphthol sulfonic acid, atent solvent, catalyst and hydrogen source is added, the additional amount of the atent solvent is that nitrous is added
0.5~20 times of base or nitronaphthol sulfonic acid weight, the additional amount of the catalyst are that nitroso or nitronaphthol sulfonic acid is added
The 0.5%~20% of weight, the hydrogen source include hydrazine hydrate or anhydrous hydrazine or ammonium formate etc., and the usage amount of hydrogen source substance is to be added
0.5~5 times of the amount of the substance of nitroso or nitronaphthol sulfonic acid, then under the conditions of -20~120 DEG C (preferably 10~80 DEG C)
Carry out transfer hydrogenation reduction reaction, 0.5~10h of reaction time (preferably 0.5~5h)；It is separated by solid-liquid separation after fully reacting, point
After the liquid concentration separated out, amino naphthol sulfonic acid needed for obtaining after acidification is separated with product, the solid catalysis isolated are carried out
Agent defeated time reaction system can continue to use again, and the solvent distilled out is concentrated defeated time reaction system can also continue to use again.It is dense
Contracting is to be evaporated solvent using air-distillation or vacuum distillation.Acidification is to be added excessively in the residue obtained after being evaporated to concentration
Acid, used acid includes hydrochloric acid, sulfuric acid, phosphoric acid or other inorganic and organic acids, is then stirred, and is translated into corresponding
The salt of acid, the salt of generation are precipitated from acid, are filtered separation later.
During transfer hydrogenation reduction reaction of the present invention, temperature is excessively high temperature an important factor for influencing reaction yield
More by-product can be generated, preferable product content and yield can not be obtained；Temperature is too low, and reaction is not thorough, and reacts
Time extends, and mother-liquor quality is influenced, to influence subsequent reactions.In above-mentioned reaction, suitable temperature is -20~120
DEG C, preferably 10~80 DEG C.
In transfer hydrogenation reduction reaction provided by the invention, catalyst and hydrogen source are acted on, and pass through the activity of catalyst surface
Site activates the hydrogen on hydrogen source, forms reactive hydrogen and participates in reduction reaction.
In above-mentioned reaction process, the time of transfer hydrogenation reduction reaction is 0.5~10h, preferably 1~5h, it is ensured that former
Expect fully reacting, is tracked in practical operation using liquid chromatogram and determine reaction end.
In above-mentioned reaction, used hydrogen source includes hydrazine hydrate or anhydrous hydrazine or ammonium formate etc.；The usage amount of hydrogen source substance
For 0.5~5 times that nitroso or nitronaphthol sulfonic acid object weight is added.
In above-mentioned reaction, used atent solvent includes alcohols solvent such as methanol, ethyl alcohol or isopropanol etc. and/or halogenated
One or more of hydro carbons, arene, ethers and esters and N,N-dimethylformamide, dimethyl sulfoxide equal solvent.
This method used catalyst be Raney's nickel catalyst, Pt/C catalyst, Pd/C catalyst or Ru/C catalyst and
The catalyst of other metals or metal oxide or Metal Supported, above-mentioned catalyst is in this reaction system to nitroso or nitro
Hydrogenating reduction all has good catalytic activity, and can be recycled.Raney's nickel catalyst Ni content used be 40%~
60% (weight), Pt content is 0.5%~5% (weight) in Pt/C catalyst, in Pd/C catalyst Pd content be 0.5%~
10% (weight) is advisable.The catalyst formed using different Lei Xing ﹑ difference, dosage and corresponding reaction condition are female to reduction
The content and yield of liquid have a direct impact.
When the catalyst is Raney's nickel catalyst: the additional amount of catalyst is that nitroso or nitronaphthol sulfonic acid weight is added
Amount 1%~10% when, can be obtained the preferable mother-liquor of content.Combined reaction condition and economic factor and reduction are female
The content requirement that liquid directly applies to subsequent reactions considers that Raney's nickel catalyst dosage is preferably with nitroso or nitro-naphthalene-monosulfonic acid
The 1%~10% of weight calculating is advisable；When using Raney's nickel catalyst, in the transfer hydrogenation, reaction temperature -20~
120 DEG C, the reaction time 0.5~5 hour.
When the catalyst is Pt/C catalyst: the additional amount of catalyst is that nitroso or nitronaphthol sulfonic acid weight is added
0.1%~10%, can be obtained the preferable mother-liquor of content.Combined reaction condition and economic factor and mother-liquor
The content requirement for directly applying to subsequent reactions considers that Pt/C catalyst amount is preferably with nitroso or nitro-naphthalene-monosulfonic acid weight
0.5%~7% calculated is advisable.When using Pt/C catalyst, in the hydrogenation reaction, reaction temperature -20~120 DEG C, reaction
Time 0.5~10 hour.
When the catalyst is Pd/C catalyst: the additional amount of catalyst is that nitroso or nitronaphthol sulfonic acid weight is added
0.1%~10%, combined reaction condition and economic factor and mother-liquor directly apply to the content requirement of subsequent reactions
Consider, Pd/C catalyst amount is preferably to be advisable with the 1%~8% of nitroso or the calculating of nitro-naphthalene-monosulfonic acid weight.Using Pd/C
When catalyst, in the hydrogenation reaction, reaction temperature -20~120 DEG C, the reaction time 0.5~10 hour.
Above-mentioned three kinds of catalyst can be met the requirements, and can be recycled more than five times.Other metals or carried metal
And metal oxide catalyst also can satisfy above-mentioned requirements, later, can conventionally recycle.Three kinds of catalyst phases
Than Raney's nickel, the transfer hydrogenation reduction yield of Pt/C with Pd/C catalyst are similar, and the cost of Raney's nickel catalyst is low, more passes through
Ji is applicable in.
Through the invention in amino naphthol sulfonic acid prepared by the above method, the position of nitroso or nitro in naphthols is
2 or 4, position of the sulfonic group in naphthols is 5 or 4 or 7.The purity of gained amino naphthol sulfonic acid product can
Up to 98% or more (liquid chromatography area normalization method), yield is up to 90% or more.
The method that transfer hydrogenation method provided by the invention prepares amino naphthol sulfonic acid has the advantage that transfer hydrogenation legal system
It is normal that standby amino naphthol sulfonic acid new process with sodium hydrosulfite or iron powder reducing nitroso or nitronaphthol sulfonic acid prepares amino naphthol sulfonic acid
Rule technique is compared, and the technological operation that the present invention develops is easy, and reaction condition is mild, and it is not necessary that water is added, good product quality has reacted
Product is obtained after being separated by filtration catalyst after, catalysts and solvents can be recycled through simple process, avoid pollution
Problem is a kind of environmentally friendly green production process.
By following embodiment, the present invention is further described in detail, but this invention is by no means limited to this.
Embodiment 1:
25.3g (0.1mol) 1- naphthols -2- nitroso -5- sulfonic acid is first added in the reaction vessel, adds 1- naphthols -2-
80% hydrazine hydrate 9.0g (0.144mol) is added in 50% ethyl alcohol of nitroso -5- sulfonic acid weight, and it is sub- to add 1- naphthols -2-
5% Raney's nickel catalyst of nitro -5- sulfonic acid weight is stirred at room temperature uniformly, controls 30 DEG C of reaction temperature, be stirred to react 3h,
Feed stock conversion reaches 98.0% or more.Catalyst is filtered out at room temperature, is obtained the solution of product, is produced after concentrated acidification
Object.
Fig. 1 is the present embodiment product HPLC map, HPLC testing conditions are as follows: instrument parameter: Agilent high performance liquid chromatography
Instrument 1100, diode array detector, chromatographic column: C18 46 × 250mm, 5 μm, mobile phase: V methanol: V water: V acetic acid: tri- second of V
Amine=14:85.1:0.6:0.3, flow velocity: 1mL/min, Detection wavelength: 254nm.
Liquid phase analysis the present embodiment product content 99.2%, yield 91%.
Embodiment 2:
25.3g (0.1mol) 1- naphthols -2- nitroso -5- sulfonic acid is first added in autoclave, 80% hydrazine hydrate is added
9.0g (0.144mol) adds 5 times of ethyl alcohol of 1- naphthols -2- nitroso -5- sulfonic acid weight, and it is sub- to add 1- naphthols -2-
5% Pt/C catalyst of nitro -5- sulfonic acid weight is stirred at room temperature uniformly, controls 20 DEG C of reaction temperature, be stirred to react 3h, former
Material conversion ratio reaches 98.2% or more.Catalyst is filtered out at room temperature, is obtained the solution of product, is produced after concentrated acidification
Object.
Liquid phase analysis product content 98.6%, yield 85%.
Embodiment 3:
25.3g (0.1mol) 1- naphthols -2- nitroso -5- sulfonic acid is first added in autoclave, 80% hydrazine hydrate is added
6.26g (0.1mol) adds 2 times of ethyl alcohol of 1- naphthols -2- nitroso -5- sulfonic acid weight, adds 1- naphthols -2- nitrous
5% Pd/C catalyst of base -5- sulfonic acid weight is stirred at room temperature uniformly, controls 40 DEG C of reaction temperature, be stirred to react 4h, raw material
Conversion ratio reaches 98.4% or more.Catalyst is filtered out at room temperature, is obtained the solution of product, is obtained product after concentrated acidification.
Liquid phase analysis product content 98.2%, yield 80%.
Embodiment 4:
25.3g (0.1mol) 1- naphthols -2- nitroso -5- sulfonic acid is first added in the reaction vessel, adds 1- naphthols -2-
80% hydrazine hydrate 9.0g (0.144mol) is added in 50% methanol of nitroso -5- sulfonic acid weight, and it is sub- to add 1- naphthols -2-
5% Raney's nickel catalyst of nitro -5- sulfonic acid weight is stirred at room temperature uniformly, controls 40 DEG C of reaction temperature, be stirred to react 2h,
Feed stock conversion reaches 98.0% or more.Catalyst is filtered out at room temperature, is obtained the solution of product, is produced after concentrated acidification
Object.
Liquid phase analysis product content 98.4%, yield 88%.
Embodiment 5:
25.3g (0.1mol) 1- naphthols -2- nitroso -5- sulfonic acid is first added in the reaction vessel, adds 1- naphthols -2-
50% methanol of nitroso -5- sulfonic acid weight is added anhydrous hydrazine 7.2g (0.144mol), adds 1- naphthols -2- nitroso -
8% Raney's nickel catalyst of 5- sulfonic acid weight is stirred at room temperature uniformly, controls 40 DEG C of reaction temperature, is stirred to react 3h, and raw material turns
Rate reaches 98.0% or more.Catalyst is filtered out at room temperature, is obtained the solution of product, is obtained product after concentrated acidification.
Liquid phase analysis product content 98.6%, yield 92%.
Embodiment 6:
25.3g 1- naphthols -2- nitroso -5- sulfonic acid (0.1mol) first is added in the reaction vessel, adds 1- naphthols -
The ethyl alcohol of 2- nitroso -5- 2 times of weight of sulfonic acid is added anhydrous formic acid ammonium 12.6g (0.2mol), adds 1- naphthols -2- nitrous
5% Pd/C catalyst of base -5- sulfonic acid weight is stirred at room temperature uniformly, controls 40 DEG C of reaction temperature, be stirred to react 3h, raw material
Conversion ratio reaches 95.0% or more.Catalyst is filtered out at room temperature, is obtained the solution of product, is obtained product after concentrated acidification.
Liquid phase analysis product content 97.3%, yield 89%.
Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Pipe present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: its according to
So be possible to modify the technical solutions described in the foregoing embodiments, or to some or all of the technical features into
Row equivalent replacement；And these are modified or replaceed, various embodiments of the present invention technology that it does not separate the essence of the corresponding technical solution
The range of scheme.
Claims (6)
1. a kind of method that transfer hydrogenation method prepares amino naphthol sulfonic acid, it is characterised in that: this method is by nitroso or nitro
Naphtholsulfonic acid carries out transfer hydrogenation reduction and prepares amino naphthol sulfonic acid；
The preparation method the following steps are included:
S110: nitroso or nitronaphthol sulfonic acid, atent solvent, catalyst and hydrogen source are sequentially added in reaction vessel, -20
Transfer hydrogenation reduction reaction, 0.5~10h of hydrogenation reaction time are carried out at~120 DEG C；
S120: being separated by solid-liquid separation after fully reacting, after the liquid concentration isolated, carries out obtaining institute after acidification is separated with product
Need amino naphthol sulfonic acid；
The hydrogen source is hydrazine hydrate, anhydrous hydrazine or ammonium formate；
The usage amount of the hydrogen source is 0.5~5 times of the amount of nitroso or nitronaphthol sulfonic acid species；
The catalyst is Raney's nickel, Pt/C or Pd/C；
Wherein: nickel content is 40~60wt.% in the Raney's nickel catalyst, in Pt/C catalyst Pt content be 0.5~
Pd content is 0.5~10wt.% in 5wt.%, Pd/C catalyst；
The atent solvent is methanol or ethyl alcohol；
In amino naphthol sulfonic acid prepared by this method, the position of raw material nitroso or nitro in naphthols is 2 or 4, sulphur
Position of the acidic group in naphthols is 5 or 4 or 7.
2. the method that transfer hydrogenation method according to claim 1 prepares amino naphthol sulfonic acid, it is characterised in that: the inertia
The additional amount of solvent is 0.5~20 times that nitroso or nitronaphthol sulfonic acid weight is added；
The additional amount of the catalyst is 0.5%~20% that nitroso or nitronaphthol sulfonic acid weight is added.
3. the method that transfer hydrogenation method according to claim 1 prepares amino naphthol sulfonic acid, it is characterised in that: the solid-liquid
After separation, defeated time reaction system continues to use the solid catalyst isolated again.
4. the method that transfer hydrogenation method according to claim 1 prepares amino naphthol sulfonic acid, it is characterised in that: the catalysis
When agent is Raney's nickel, the additional amount of Raney's nickel is 1%~10% that nitroso or nitronaphthol sulfonic acid weight is added；The transfer
In hydro-reduction reaction, reaction temperature -20~120 DEG C, 0.5~10h of reaction time.
5. the method that transfer hydrogenation method according to claim 1 prepares amino naphthol sulfonic acid, it is characterised in that: the catalysis
When agent is Pt/C, the additional amount of Pt/C is 0.1%~10% that nitroso or nitronaphthol sulfonic acid weight is added, the transfer hydrogen
Change in reduction reaction, reaction temperature -20~120 DEG C, 0.5~10h of reaction time.
6. the method that transfer hydrogenation method according to claim 1 prepares amino naphthol sulfonic acid, it is characterised in that: the catalysis
When agent is Pd/C, the additional amount of Pd/C is 0.1%~10% that nitroso or nitronaphthol sulfonic acid weight is added, the transfer hydrogen
Change in reduction reaction, reaction temperature -20~120 DEG C, 0.5~10h of reaction time.
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| CN105777588A (en) * | 2016-04-02 | 2016-07-20 | 田菱精细化工（大连）有限公司 | Method for preparing amino-naphthol-sulfonic acid through catalytic hydrogenation |
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