CN102618063A - Method for preparing water-soluble azo dye continuously by chaos mixing of spiral tube - Google Patents
Method for preparing water-soluble azo dye continuously by chaos mixing of spiral tube Download PDFInfo
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Abstract
The invention provides a method for preparing a water-soluble azo dye continuously by the chaos mixing of a spiral tube. The core is that a spiral tube sudden-expansion and sudden-contraction structure is adopted; compared with pure straight tube sudden-expansion and sudden-contraction mixed reaction, the method has the advantages that a mixed effect of a transverse secondary flow generated by fluid in a curved pipeline is far stronger than that of pure diffusion of a straight tube part; compared with the conventional spiral tube, the sudden-expansion and sudden-contraction part has the advantages that the motion trail of the fluid can be changed, the superficial area of a mixed interface can be increased and a chaos mixing effect can be enhanced; and the mixer has the advantages of quick and uniform mixing, stirring prevention, short retention time, high quality stability of the product, high speed of removing reaction heat by a tube wall and the like of a microreactor, and also overcomes the defects of small internal diameter and high possibility of blockage of the microreactor, so that the dye can be produced quickly and continuously, and the method is wide in industrial prospect.
Description
Technical field
The present invention relates to a kind of continuous preparation method of spiral tube chaotic mixing of soluble azo dyes.
Background technology
The azoic dyestuff kind is numerous, comprise acidity, directly, classifications such as activity and dispersed dye, its YO accounts for the over half of world's dyestuff, is one type of extremely important dye class.Relate to the coupled reaction course in process of production, promptly coupling components such as diazonium salt and arylamine or phenol generate the reaction of azo cpd, are the important steps of producing azoic dyestuff.But coupled reaction is thermopositive reaction, and diazonium salt is to thermally labile, and therefore conventional intermittent type synthesis technique all will carry out under the refrigerative situation; Generally all with the ice-water bath cooling, temperature maintenance is carried out coupled reaction at 0～5 ℃, causes energy dissipation; And in the coupled reaction process; Because cold operation, coupling speed is slow, long reaction time.Therefore intermittent reaction exists that production capacity is low, energy consumption is big, is badly in need of the coupling serialization production technology of exploitation azoic dyestuff, and this promotes quality product and have important industrial application value for the energy-saving and emission-reduction that realize that azoic dyestuff is produced.
The serialization preparation is meant that material carries out short mix and reaction in flowing, and has the advantage that the reaction times is short, production capacity is high, in chemosynthesis, occupies and consequence, mainly comprises two types of microreactor and tubular reactors.Human diazonium salt of aniline such as Robert C.R.Wootton and beta naphthal carry out the coupled reaction serialization in microreactor, synthesized corresponding azoic dyestuff (Lab Chip, 2002,2,5-7).But the complex manufacturing technology of microreactor, in case and the passage obstruction, be difficult to clean, and the material treatment capacity of microreactor is little, is difficult to be used for extensive DYE PRODUCTION.And that tubular reactor has is simple in structure, easy to process, throughput big, realize control automatically easily, save power, heat transfer area is big, be fit to the characteristics of strong thermopositive reaction; Be to use the more higher spiral cast reactor drum of a kind of continuous manipulation reactor, especially mixing efficiency.Because action of centrifugal force is identical, can not produce the fluctuation back and forth of mixed interface.But for common spiral tube; The secondary stream whirlpool a pair of in the opposite direction that fluid produces at the volley has been divided into two enclosed areas with fluid; Be unfavorable for uniform mixing (A.Yamagishi; T.Inaba, Y Yamaguchi.International Journal of Heat and Mass Transfer.50 (2007), 1238-1247).
And have a prominent chaos mixer (forming sudden expansion sudden contraction structure) of putting the sudden contraction function through the cross-sectional area that changes the fluid channel; Can produce chaotic mixing; Can significantly improve mixed performance (Arjun P.Sudarsan, Victor M.Ugaz.Lab Chip.6 (2006), 74-82.But chaos mixer is mainly straight pipe type sudden expansion sudden contraction structure at present, does not see that the reactor drum of spiral cast sudden expansion sudden contraction structure reaches the relevant report of in this reactor drum, carrying out the coupling continuous reaction.
Summary of the invention
The invention provides the spiral tube chaotic mixing reaction method that a kind of serialization prepares soluble azo dyes.The following technical scheme of concrete employing:
A kind of continuous preparation method of spiral tube chaotic mixing of soluble azo dyes: diazonium salt solution is through volume pump I input spiral tube chaotic mixing unit, and coupling component solution is through volume pump II input spiral tube chaotic mixing unit; Diazonium salt solution and coupling component solution flow in spiral tube chaotic mixing unit, and the abundant coupling of two components makes soluble azo dyes solution; Said method need not cooled off or heated.
Spiral tube chaotic mixing according to the invention unit is alternately to be formed by connecting pinion head pipe and thin spiral tube, and its linking number is 1～500.
In the preferred scheme, the internal diameter of pinion head pipe is that 1-100mm, radius-of-curvature are that 5-500mm, pitch are 1-100mm in the said reactor drum.
In the preferred another scheme, the internal diameter of thin spiral tube is that 0.5-30mm, radius-of-curvature are that 5-500mm, pitch are 1-100mm in the said reactor drum.
The continuous preparation method of the spiral tube chaotic mixing of soluble azo dyes provided by the invention; Utilize the high efficient mixed and the sudden expansion sudden contraction of the horizontal secondary stream that fluid produces in dog leg(ged)piping can change the liquid motion track, increase the mixed interface surface-area; Strengthen the characteristic of chaotic mixing effect; Make that the diazonium salt component fully contacts with the coupling component, short mix and coupled reaction, and reaction heat removed through pipeline fast, realize the quick and continuous production of dyestuff; Have the characteristic simple fast, that energy consumption is low, have broad application prospects.
Method provided by the invention, according to the difference of pH value in the coupled reaction process, the coupling process is divided under the acidic conditions two kinds of processes of coupling under the coupling and alkaline condition.
(1) coupling under the acidic conditions: the coupling component (transferring its pH value) soluble in water that will contain the arylamine structure below 7; Utilize constant flow pump, the aqueous solution and the diazonium salt solution of coupling component is transported to respectively in the spiral tube chaos continuous reaction device, mix and coupling; The control flow velocity; When the volume logistics of reactant was correct, the pH value of the product solution of reactor exit obtained soluble azo dyes solution less than 5.
(2) coupling under the alkaline condition: the coupling component (transferring its pH value) soluble in water that will contain active methylene radical or phenolic hydroxyl group more than 9; Utilize constant flow pump, the aqueous solution and the diazonium salt solution of coupling component is transported to respectively in the spiral tube chaos continuous reaction device, mix and coupling; The control flow velocity; When the volume logistics of reactant was correct, the pH value of the product solution of reactor exit obtained soluble azo dyes solution greater than 7.
The spiral tube chaotic mixing continuous preparation method of quick preparation soluble azo dyes provided by the invention, its core with adopted spiral cast sudden expansion sudden contraction structure.It is compared with simple straight tube sudden expansion sudden contraction type mixing tank, and the mixed effect of the horizontal secondary stream that fluid produces in dog leg(ged)piping far is better than the mixing of the simple dependence diffusion of straight-tube portion; Compare with the spiral tube of routine; Sudden expansion sudden contraction part can change the liquid motion track again, increase the mixed interface surface-area; Strengthen the chaotic mixing effect, and this mixing tank both kept microreactor the mixing rapid and uniform, need not stir, the residence time is short, constant product quality property is high, reaction heat advantage such as removes fast through tube wall, has overcome that the microreactor internal diameter is too small, the shortcoming of easy blocking simultaneously again; Realize the quick and continuous production of dyestuff, have wide industrial prospect.
Description of drawings
The synoptic diagram of Fig. 1 spiral tube chaos continuous reaction;
Fig. 2 spiral tube chaotic mixing cell schematics.
Among the figure, 1, the diazonium salt solution input unit, 2, coupling component solution input unit, 3, volume pump I, 4, volume pump II; 5, spiral tube chaotic mixing unit; D, curvature diameter, d, bore, b, pitch.
Embodiment
Following embodiment can make those of ordinary skill in the art more fully understand the present invention, but does not limit the present invention in any way.
Embodiment 1
The preparation of coupling component solution: in the 250ml flask that fills 20ml water; Add 3.41g 1-amino-8-hydroxyl-3, the 6-naphthalene disulfonic acid under agitation adds concentration and is 20% sodium carbonate solution; Adjusting pH is 6.0-6.5; Thin up coupling component solution to TV 200ml, pH be 6.0-6.5, obtain containing 1-amino-8-hydroxyl-3, the solution for standby of 6-naphthalene disulfonic acid coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 30ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 10 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 3mm, radius-of-curvature are that 8mm, pitch are 5mm; The internal diameter of thin spiral tube is that 2mm, radius-of-curvature are that 8mm, pitch are 5mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 2-22
With P-nethoxyaniline diazonium salt solution, Ortho-Chloro aniline diazonium salt solution, naphthalidine diazonium salt solution, aniline 2; 5 disulfonic acid diazonium salt solutions, p-Nitroaniline diazonium salt solution, m-nitraniline diazonium salt solution, o-Nitraniline diazonium salt solution, itrile group diazonium salt of aniline solution, Sulphanilic Acid diazonium salt solution, ORTHO AMINO PHENOL SULPHONIC diazonium salt solution, 1-amino-4-naphthene sulfonic acid diazonium salt solution and structure be respectively the diazonium salt solution of 1-10#; Replace diazonium salt of aniline solution; In spiral tube chaos continuous reaction device respectively with 1-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid solution reaction; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 1.
Embodiment 23-33
With naphthalidine-6-sulfonic acid, 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; The coupling component solution that 4-naphthalene disulfonic acid, 1-anilino-8-naphthene sulfonic acid solution and structure are respectively 11-14# replaces 1-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device, with the diazonium salt of aniline solution reaction, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 1.
Embodiment 34-44
With naphthalidine-6-sulfonic acid, 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; The coupling component solution that 4-naphthalene disulfonic acid, 1-anilino-8-naphthene sulfonic acid solution and structure are respectively 11-14# replaces 1-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device, with the reaction of p-Nitroaniline diazonium salt solution, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 1.
Embodiment 45-55
With naphthalidine-6-sulfonic acid, 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; The coupling component solution that 4-naphthalene disulfonic acid, 1-anilino-8-naphthene sulfonic acid solution and structure are respectively 11-14# replaces 1-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device, with the reaction of Sulphanilic Acid diazonium salt solution, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 1.
Embodiment 56-66
With naphthalidine-6-sulfonic acid, 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; The coupling component solution that 4-naphthalene disulfonic acid, 1-anilino-8-naphthene sulfonic acid solution and structure are respectively 11-14# replaces 1-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device, be the diazonium salt solution reaction of 10# with structure, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 1.
Embodiment 67-77
With naphthalidine-6-sulfonic acid, 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; The coupling component solution that 4-naphthalene disulfonic acid, 1-anilino-8-naphthene sulfonic acid solution and structure are respectively 11-14# replaces 1-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device, be the diazonium salt solution reaction of 8# with structure, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 1.
Embodiment 78-88
With naphthalidine-6-sulfonic acid, 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; The coupling component solution that 4-naphthalene disulfonic acid, 1-anilino-8-naphthene sulfonic acid solution and structure are respectively 11-14# replaces 1-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device, be the diazonium salt solution reaction of 6# with structure, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 1
Embodiment 89
The preparation of coupling component solution: in the 250ml flask that fills 40ml water, add 3.18g 1-amino-8-hydroxyl-3; The 6-naphthalene disulfonic acid; Under agitation add concentration and be 20% sodium carbonate solution, adjusting pH is 9.5-9.9, and it is 200ml that last water forms TV.
Utilize the p-Nitroaniline diazonium salt solution in atomizing-pipeline coupling flow reactor with 1-aminophenyl-8-hydroxyl-3, (the pinion head pipe is 10 with the linking number of thin spiral tube to 6-naphthalene disulfonic acid solution in this reactor drum in spiral tube chaos continuous reaction device reaction; The internal diameter of pinion head pipe is that 3mm, radius-of-curvature are that 8mm, pitch are 5mm; The internal diameter of thin spiral tube is that 2mm, radius-of-curvature are that 8mm, pitch are 5mm), the pH value of the product solution of reactor exit is 7.0-8.0, obtains soluble azo dyes solution.
Embodiment 90-101
Utilize 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; 4-naphthalene disulfonic acid, 1-benzoyl amino-8-hydroxyl-3,6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3,6-naphthalene disulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-6-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 5-hydroxyl-7-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-4-naphthene sulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-2; 4-naphthalene disulfonic acid solution replaces 1-amino-8-hydroxyl-3, and 6-naphthalene disulfonic acid solution reacts with the p-Nitroaniline diazonium salt solution in spiral tube chaos continuous reaction device; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 102-113
Utilize 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; 4-naphthalene disulfonic acid, 1-benzoyl amino-8-hydroxyl-3,6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3,6-naphthalene disulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-6-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 5-hydroxyl-7-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-4-naphthene sulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-2; 4-naphthalene disulfonic acid solution replaces 1-amino-8-hydroxyl-3,6-naphthalene disulfonic acid solution, in spiral tube chaos continuous reaction device with the diazonium salt of aniline solution reaction; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 114-125
Utilize 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; 4-naphthalene disulfonic acid, 1-benzoyl amino-8-hydroxyl-3,6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3,6-naphthalene disulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-6-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 5-hydroxyl-7-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-4-naphthene sulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-2; 4-naphthalene disulfonic acid solution replaces 1-amino-8-hydroxyl-3, and 6-naphthalene disulfonic acid solution reacts with the Sulphanilic Acid diazonium salt solution in spiral tube chaos continuous reaction device; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 126-137
Utilize 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; 4-naphthalene disulfonic acid, 1-benzoyl amino-8-hydroxyl-3,6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3,6-naphthalene disulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-6-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 5-hydroxyl-7-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-4-naphthene sulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-2; 4-naphthalene disulfonic acid solution replaces 1-amino-8-hydroxyl-3, and 6-naphthalene disulfonic acid solution is the diazonium salt reaction of 2# with structure in spiral tube chaos continuous reaction device; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 138-149
Utilize 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; 4-naphthalene disulfonic acid, 1-benzoyl amino-8-hydroxyl-3,6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3,6-naphthalene disulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-6-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 5-hydroxyl-7-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-4-naphthene sulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-2; 4-naphthalene disulfonic acid solution replaces 1-amino-8-hydroxyl-3, and 6-naphthalene disulfonic acid solution is the diazonium salt reaction of 7# with structure in spiral tube chaos continuous reaction device; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 150-161
Utilize 2-amino-8-hydroxyl-6-naphthene sulfonic acid, 2-amino-5-hydroxyl-7-naphthene sulfonic acid, 2-amino-8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-amino-8-hydroxyl-4-naphthene sulfonic acid, 1-amino-8-hydroxyl-2; 4-naphthalene disulfonic acid, 1-benzoyl amino-8-hydroxyl-3,6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3,6-naphthalene disulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-6-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 5-hydroxyl-7-naphthene sulfonic acid, 2-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-3; 6-naphthalene disulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-4-naphthene sulfonic acid, 1-acetylaminohydroxyphenylarsonic acid 8-hydroxyl-2; 4-naphthalene disulfonic acid solution replaces 1-amino-8-hydroxyl-3, and 6-naphthalene disulfonic acid solution is the diazonium salt reaction of 9# with structure in spiral tube chaos continuous reaction device; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 162-183
The preparation of coupling component solution: in the 250ml flask that fills 40ml water, add 2.54g 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone; Under agitation add concentration and be 20% sodium carbonate solution; Adjusting pH is 9.5-9.9, and it is 200ml that last water forms TV.
(the pinion head pipe is 10 with the linking number of thin spiral tube in this reactor drum in the reaction of spiral tube chaos continuous reaction device with 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone solution in spraying gun-pipeline coupling flow reactor to utilize diazonium salt solution among the instance 1-22 respectively; The internal diameter of pinion head pipe is that 3mm, radius-of-curvature are that 8mm, pitch are 5mm; The internal diameter of thin spiral tube is that 2mm, radius-of-curvature are that 8mm, pitch are 5mm), the pH value of the product solution of reactor exit is 7.0-8.0, makes soluble azo dyes solution.
Embodiment 184-185
Utilize 15-16# coupling component solution to replace 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone solution; In spiral tube chaos continuous reaction device, be the diazonium salt reaction of 1# with structure; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 162.
Embodiment 186-187
Utilize 15-16# coupling component solution to replace 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone solution; In spiral tube chaos continuous reaction device, react with the Sulphanilic Acid diazonium salt; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 162.
Embodiment 188-189
Utilize 15-16# coupling component solution to replace 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone solution; In spiral tube chaos continuous reaction device, be the diazonium salt reaction of 7# with structure; Make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 162.
Embodiment 190-207
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#; 6-naphthalene disulfonic acid solution; At spiral tube chaos continuous reaction device and structure is the diazonium salt reaction of 1#, makes corresponding soluble azo dyes solution, and other conditions are consistent with embodiment 89.
Embodiment 208-225
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device and the reaction of p-Nitroaniline diazonium salt, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 226-243
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#, 6-naphthalene disulfonic acid solution in spiral tube chaos continuous reaction device and diazonium salt of aniline reaction, makes corresponding soluble azo dyes solution, and other conditions are consistent with embodiment 89.
Embodiment 244-261
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#; 6-naphthalene disulfonic acid solution; In spiral tube chaos continuous reaction device and the reaction of Sulphanilic Acid diazonium salt, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 262-279
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 3#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 280-297
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 5#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 298-315
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 7#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 316-333
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 17-34#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 9#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 334-359
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 35-60#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 10#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 360-385
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 35-60#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 8#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 386-411
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 35-60#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 6#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 412-437
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 35-60#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 4#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 438-463
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 35-60#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of 2#, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 464-489
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 35-60#; 6-naphthalene disulfonic acid solution; Spiral tube chaos continuous reaction device with to structure be the diazonium salt reaction of p-Nitroaniline, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 490-515
Utilize structure to replace 1-amino-8-hydroxyl-3 for the coupling component solution of 35-60#; 6-naphthalene disulfonic acid solution; React at spiral tube chaos continuous reaction device and to the diazonium salt with aniline, make corresponding soluble azo dyes solution, other conditions are consistent with embodiment 89.
Embodiment 516
The preparation of coupling component solution: in the flask that fills 2000ml water; Add 341g 1-amino-8-hydroxyl-3, the 6-naphthalene disulfonic acid under agitation adds concentration and is 20% sodium carbonate solution; Adjusting pH is 6.0-6.5; Thin up coupling component solution to TV 20000ml, pH be 6.0-6.5, obtain containing 1-amino-8-hydroxyl-3, the solution for standby of 6-naphthalene disulfonic acid coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 100ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 100 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 10mm, radius-of-curvature are that 20mm, pitch are 50mm; The internal diameter of thin spiral tube is that 5mm, radius-of-curvature are that 20mm, pitch are 50mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 517
The preparation of coupling component solution: in the flask that fills 2000ml water; Add 341g 1-amino-8-hydroxyl-3, the 6-naphthalene disulfonic acid under agitation adds concentration and is 20% sodium carbonate solution; Adjusting pH is 6.0-6.5; Thin up coupling component solution to TV 20000ml, pH be 6.0-6.5, obtain containing 1-amino-8-hydroxyl-3, the solution for standby of 6-naphthalene disulfonic acid coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 300ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 400 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 30mm, radius-of-curvature are that 100mm, pitch are 80mm; The internal diameter of thin spiral tube is that 15mm, radius-of-curvature are that 100mm, pitch are 80mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 518
The preparation of coupling component solution: in the flask that fills 2000ml water; Add 341g 1-amino-8-hydroxyl-3, the 6-naphthalene disulfonic acid under agitation adds concentration and is 20% sodium carbonate solution; Adjusting pH is 6.0-6.5; Thin up coupling component solution to TV 20000ml, pH be 6.0-6.5, obtain containing 1-amino-8-hydroxyl-3, the solution for standby of 6-naphthalene disulfonic acid coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 500ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 450 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 60mm, radius-of-curvature are that 200mm, pitch are 90mm; The internal diameter of thin spiral tube is that 30mm, radius-of-curvature are that 200mm, pitch are 90mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 519
The preparation of coupling component solution: in the flask that fills 2000ml water; Add 341g 1-amino-8-hydroxyl-3, the 6-naphthalene disulfonic acid under agitation adds concentration and is 20% sodium carbonate solution; Adjusting pH is 9.5-9.9; Thin up coupling component solution to TV 20000ml, adjusting pH be 9.5-9.9, obtain containing 1-amino-8-hydroxyl-3, the solution for standby of 6-naphthalene disulfonic acid coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 100ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 100 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 10mm, radius-of-curvature are that 20mm, pitch are 50mm; The internal diameter of thin spiral tube is that 5mm, radius-of-curvature are that 20mm, pitch are 50mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 520
The preparation of coupling component solution: in the flask that fills 2000ml water; Add 341g 1-amino-8-hydroxyl-3, the 6-naphthalene disulfonic acid under agitation adds concentration and is 20% sodium carbonate solution; Adjusting pH is 9.5-9.9; Thin up coupling component solution to TV 20000ml, adjusting pH be 9.5-9.9, obtain containing 1-amino-8-hydroxyl-3, the solution for standby of 6-naphthalene disulfonic acid coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 300ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 400 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 30mm, radius-of-curvature are that 100mm, pitch are 80mm; The internal diameter of thin spiral tube is that 15mm, radius-of-curvature are that 100mm, pitch are 80mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 521
The preparation of coupling component solution: in the flask that fills 2000ml water; Add 341g 1-amino-8-hydroxyl-3, the 6-naphthalene disulfonic acid under agitation adds concentration and is 20% sodium carbonate solution; Adjusting pH is 9.5-9.9; Thin up coupling component solution to TV 20000ml, adjusting pH be 9.5-9.9, obtain containing 1-amino-8-hydroxyl-3, the solution for standby of 6-naphthalene disulfonic acid coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 500ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 450 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 60mm, radius-of-curvature are that 200mm, pitch are 90mm; The internal diameter of thin spiral tube is that 30mm, radius-of-curvature are that 200mm, pitch are 90mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 522
The preparation of coupling component solution: in the flask that fills 4000ml water, add 254g 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone; Under agitation add concentration and be 20% sodium carbonate solution; Adjusting pH is 9.5-9.9; It is that 20000ml, adjusting pH are 9.5-9.9 that last water forms TV, obtains containing the solution for standby of 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 100ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 100 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 10mm, radius-of-curvature are that 20mm, pitch are 50mm; The internal diameter of thin spiral tube is that 5mm, radius-of-curvature are that 20mm, pitch are 50mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 523
The preparation of coupling component solution: in the flask that fills 4000ml water, add 254g 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone; Under agitation add concentration and be 20% sodium carbonate solution; Adjusting pH is 9.5-9.9; It is that 20000ml, adjusting pH are 9.5-9.9 that last water forms TV, obtains containing the solution for standby of 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 300ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 400 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 30mm, radius-of-curvature are that 100mm, pitch are 80mm; The internal diameter of thin spiral tube is that 15mm, radius-of-curvature are that 100mm, pitch are 80mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Embodiment 524
The preparation of coupling component solution: in the flask that fills 4000ml water, add 254g 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone; Under agitation add concentration and be 20% sodium carbonate solution; Adjusting pH is 9.5-9.9; It is that 20000ml, adjusting pH are 9.5-9.9 that last water forms TV, obtains containing the solution for standby of 1-p-sulfonic acid phenyl-3-methyl-5-pyrazolone coupling component.Prepare the diazonium salt of aniline solution for standby identical with coupling component solution volumetric molar concentration.
Utilize the calibration constant flow pump; The flow of regulating diazonium salt of aniline solution and coupling component solution is 500ml/min, diazonium salt of aniline solution and above-mentioned coupling component solution is conveyed into respectively in the spiral tube chaos continuous reaction device (the pinion head pipe is 450 with the linking number of spiral tube carefully in this reactor drum; The internal diameter of pinion head pipe is that 60mm, radius-of-curvature are that 200mm, pitch are 90mm; The internal diameter of thin spiral tube is that 30mm, radius-of-curvature are that 200mm, pitch are 90mm), the product pH value of solution value of reactor exit is 2-3, obtains soluble azo dyes solution.
Claims (4)
1. the continuous preparation method of the spiral tube chaotic mixing of soluble azo dyes; It is characterized in that; Diazonium salt solution is through volume pump I (3) input spiral tube chaotic mixing unit (5), and coupling component solution is through volume pump II (4) input spiral tube chaotic mixing unit (5); Diazonium salt solution and coupling component solution flow in spiral tube chaotic mixing unit, and the abundant coupling of two components makes soluble azo dyes solution; Said method need not cooled off or heated.
2. method according to claim 1 is characterized in that, said spiral tube chaotic mixing unit (5) is alternately to be formed by connecting pinion head pipe and thin spiral tube, and its linking number is 1～500.
3. spiral tube chaotic mixing according to claim 1 unit, the internal diameter that it is characterized in that pinion head pipe in this reactor drum are that 1-100mm, radius-of-curvature are that 5-500mm, pitch are 1-100mm.
4. spiral tube chaotic mixing according to claim 1 unit is characterized in that the internal diameter of thin spiral tube in this reactor drum is that 0.5-30mm, radius-of-curvature are that 5-500mm, pitch are 1-100mm.
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| CN103949190A (en) * | 2014-04-11 | 2014-07-30 | 浙江通源材料科技有限公司 | Industrial preparation apparatus for noble metal catalysts |
| CN104193030A (en) * | 2014-08-11 | 2014-12-10 | 中国石油大学(华东) | Device for flocculating and separating calcium-magnesium precipitate in formation water through alkaline flooding |
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| CN110787747A (en) * | 2019-10-16 | 2020-02-14 | 天津大学 | Tubular micro mixer and continuous preparation method of azo pigment by using same |
| CN114437842A (en) * | 2020-10-20 | 2022-05-06 | 中国石油化工股份有限公司 | Gas continuous separation system of hydrate method combined membrane method and disturbance device thereof |
| CN112500713A (en) * | 2020-12-03 | 2021-03-16 | 浙江龙盛染料化工有限公司 | Continuous preparation method of azo disperse dye |
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