CN108659569A - A method of preparing solvent red 24 - Google Patents
A method of preparing solvent red 24 Download PDFInfo
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- CN108659569A CN108659569A CN201810526585.9A CN201810526585A CN108659569A CN 108659569 A CN108659569 A CN 108659569A CN 201810526585 A CN201810526585 A CN 201810526585A CN 108659569 A CN108659569 A CN 108659569A
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- added dropwise
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/068—Naphthols
Abstract
The invention discloses a kind of method preparing solvent red 24, step is：By ortho-aminotoluene, methanol is put into reactor, 30wt% hydrochloric acid is added dropwise at 20~25 DEG C, then cools down, at 2~5 DEG C, 40wt% sodium nitrite solutions are added dropwise, after dripping off, then keep the temperature 3 hours, rise to room temperature, 2 hours are kept the temperature again, and soft water, stirring, filtering is added, it washs to filtrate pH and is in neutrality, it is dry；By ortho-aminotoluene, soft water, above-mentioned single coupling material, puts into reactor, 30wt% hydrochloric acid is added dropwise at 20~25 DEG C, then cool down, at 2~5 DEG C, 20wt% sodium nitrite solutions are added dropwise, after dripping off, then 4 hours are kept the temperature, 2 naphthols and 5% liquid caustic soda mixed solution are then added dropwise at 2~5 DEG C, after dripping off, 2 hours are kept the temperature, adjusts pH value, heat preservation 5 hours, repetition measurement PH, filtering, filter cake are dry after cleaning repeatedly.Reaction time of the invention shortens, and more thoroughly, product yield improves nearly 30 percentage points to reaction ratio, almost no coupling product, and product coloured light, intensity are all good.
Description
Technical field
The present invention relates to a kind of preparation methods of solvent red 24, belong to the manufacturing technology field of chemical industry dye material.
Background technology
Entitled 1- (2- methyl -4- (2- methylphenylazos) the phenylazo)-beta naphthal of solvent red 24 chemistry, kind tool
There is good weathering light fastness, and bright in luster pure, is widely used in the transparent or opaque of various thermoplastics
Color；The various coloring plastics such as terylene, nylon, engineering material；Polystyrene, ABS resin, plexiglass, vinegar
The coloring of sour fiber and polyvinyl chloride etc.；The dope dyeing of polyester fiber is can also be used for, properties of product are stablized.Its molecular formula is
C24H20N4O, relative molecular mass 380.449.Solvent red 24 structural formula is：
It is produced on a small quantity though the kind has producer at home at present, the existing defects on application performance, i.e., in resin
Disperse poor performance when coloring, causes color spot.Thus cause product that can not be applied to high-end market, the blue production-scale expansion of limitation
Exhibition.International market is to this proposition active demand.Therefore, synthesize high quality, high application performance product, meet high-end market and want
It asks and has important practical significance.
Invention content
Product yield is low, the reaction time is long in order to overcome, and the present invention proposes a kind of synthesis technology of solvent red 24.
In order to solve the above-mentioned technical problem, technical scheme of the present invention is summarized as follows：A kind of synthetic method of solvent red 24,
It mainly includes the following steps that：
Step 1, single coupling reaction：By ortho-aminotoluene, methanol is put into reactor, and 30wt% hydrochloric acid is added dropwise, then drops
40wt% sodium nitrite solutions are added dropwise at a certain temperature in temperature, control temperature, after a few hours drip off, then keep the temperature a few hours, rise
To room temperature, then a few hours are kept the temperature, a certain amount of soft water is added, stirred a few hours, start to filter, with room temperature water washing to filtrate PH
It is in neutrality, dries, weigh；
Step 2, double coupling reactions：Single coupling material prepared by ortho-aminotoluene, soft water, step 1, puts into reactor, drop
Add 30wt% hydrochloric acid, then cool down, at a certain temperature, 20wt% sodium nitrite solutions is added dropwise, controls temperature, a few hours drip off
Afterwards, then 3 hours are kept the temperature, beta naphthal and 5% liquid caustic soda mixed solution is then added dropwise, control temperature, after a few hours drip off, heat preservation 2 is small
When, then with 5% liquid caustic soda tune pH value, a few hours are kept the temperature, repetition measurement PH, filtering, filter cake washs with hot water to neutrality, 1% liquid of filter cake
Alkali is beaten a few hours, filtering, and filter cake is washed with hot water to neutrality, and filter cake is beaten a few hours, filtering, filter cake with 1% hydrochloric acid again
It is washed to neutrality with hot water, drying is weighed.
In step 1, the mass ratio of the ortho-aminotoluene and methanol is 1：0.68~0.91；Ortho-aminotoluene and 30% hydrochloric acid
Mass ratio is 1：0.64；The mass ratio of ortho-aminotoluene and 40% sodium nitrite is 1：0.73~0.77,30% hydrochloric acid temperature is added dropwise
20~25 DEG C, 2~5 DEG C of 40% sodium nitrite temperature is added dropwise, is warming up to 20~25 DEG C.
In step 2, the mass ratio of single coupling material and ortho-aminotoluene is 1：0.025；The matter of single coupling material and 30wt% hydrochloric acid
Amount is than being 1：1.346；The mass ratio of single coupling material and 20wt% sodium nitrite solutions is 1：1.762；Single coupling material and beta naphthal
Mass ratio be 1：0.785；The mass ratio of single coupling material and 5% liquid caustic soda is 1：4.48,20~25 DEG C of 30% hydrochloric acid temperature is added dropwise,
2~5 DEG C of 20% sodium nitrite temperature is added dropwise, 2~5 DEG C of beta naphthal aqueous slkali temperature is added dropwise, 5% liquid caustic soda tune PH is equal to 8.
The present invention compared with prior art, has the advantages that notable：(1) reaction time shortens；(2) react more thorough
Bottom；(3) product yield improves nearly 30 percentage points；(4) almost no coupling product, product coloured light, intensity are all good.
Specific implementation mode
The following examples illustrate the present invention in more detail, rather than limitation of the invention further.
In this application, inventor has found, sodium nitrate solution has unique catalytic effect, under the catalyst, instead
Short between seasonable, reaction is thorough, and reaction process relatively cleans, and product yield is high, and coloured light intensity is all good, there is good application value.
A kind of to prepare solvent red 24 method, specific reaction step is as follows：
1, single coupling reaction：Ortho-aminotoluene 22g, 15~20g of methanol are put into reactor, control 20~25 DEG C of dropwise additions
30% hydrochloric acid 14g, 30min are dripped off, and are cooled to 2~5 DEG C, and 40% 16~17g of sodium nitrate solution, soaking time 3h, heating is added dropwise
To 20~25 DEG C of heat preservation 2h, adds 50ml soft water, stir 30min, start to filter, be in neutrality with room temperature water washing to filtrate PH, dry
It is dry, it weighs.
2, double coupling reactions：By ortho-aminotoluene 0.4g, soft water 150g, single coupling 15.6g, put into reactor, control 20
~25 DEG C are added dropwise 30% hydrochloric acid 21g, and 30min is dripped off, and are cooled to 2~5 DEG C, and 20% sodium nitrate solution 27.5g, soaking time is added dropwise
Then beta naphthal and 5% liquid caustic soda mixed solution 80.25g is added dropwise in 4h, control temperature, after 1 hour drips off, keeps the temperature 2 hours, then use
After 5% liquid caustic soda 20g tune PH, heat preservation 3~5h, repetition measurement PH=8, filtering, filter cake is washed with hot water to neutrality.1% liquid caustic soda of filter cake
Mashing 2 hours, filtering, filter cake are washed with hot water to neutrality, and filter cake is beaten 2 hours with 1% hydrochloric acid again, filtering, filter cake heat
Water washing is weighed to neutrality, drying.
Embodiment 1
The synthesis that step 1 is singly coupled
In the 200ml four-hole bottles with mechanical agitation, thermometer, ortho-aminotoluene 22g, methanol 15g is added, unlatching is stirred
It mixes, 25 DEG C are added dropwise 30% hydrochloric acid 14g, and 30min is dripped off, and are cooled to 5 DEG C, and 40% sodium nitrate solution 17g, soaking time 3h is added dropwise,
25 DEG C of heat preservation 2h are warming up to, adds 50ml soft water, stirs 30min, start to filter, be in neutrality with room temperature water washing to filtrate PH, dry
It is dry, obtain 18.66g, purity 96.21%, yield 91.2%.
Embodiment 2
The synthesis that step 1 is singly coupled
In the 200ml four-hole bottles with mechanical agitation, thermometer, ortho-aminotoluene 22g, methanol 18g is added, unlatching is stirred
It mixes, 22 DEG C are added dropwise 30% hydrochloric acid 14g, and 30min is dripped off, and are cooled to 2 DEG C, and 40% sodium nitrate solution 16g, soaking time 3h is added dropwise,
22 DEG C of heat preservation 2h are warming up to, adds 50ml soft water, stirs 30min, start to filter, be in neutrality with room temperature water washing to filtrate PH, dry
It is dry, obtain 18.92g, purity 95.89%, yield 92.47%.
Embodiment 3
The synthesis that step 1 is singly coupled
In the 200ml four-hole bottles with mechanical agitation, thermometer, ortho-aminotoluene 22g, methanol 20g is added, unlatching is stirred
It mixes, 25 DEG C are added dropwise 30% hydrochloric acid 14g, and 30min is dripped off, and are cooled to 3 DEG C, and 40% sodium nitrate solution 16.5g, soaking time is added dropwise
3h is warming up to 25 DEG C of heat preservation 2h, adds 50ml soft water, stir 30min, start to filter, be in neutrality with room temperature water washing to filtrate PH,
Drying, obtains 18.87g, purity 96.81%, yield 92.29%.
Embodiment 4
The synthesis that step 1 is singly coupled
In the 200ml four-hole bottles with mechanical agitation, thermometer, ortho-aminotoluene 22g, methanol 15g is added, unlatching is stirred
It mixes, 25 DEG C are added dropwise 30% hydrochloric acid 14g, and 30min is dripped off, and are cooled to 5 DEG C, and 40% sodium nitrate solution 17g, soaking time 3h is added dropwise,
25 DEG C of heat preservation 2h are warming up to, adds 50ml soft water, stirs 30min, start to filter, be in neutrality with room temperature water washing to filtrate PH, dry
It is dry, obtain 19.01g, purity 96.34%, yield 92.91%.
Embodiment 5
The synthesis of step 2 pair coupling
In the 500ml four-hole bottles with mechanical agitation, thermometer, the single coupling 15.6g for implementing 1 production, control is added
20 DEG C are added dropwise 30% hydrochloric acid 21g, and 30min is dripped off, and are cooled to 5 DEG C, 20% sodium nitrate solution 27.5g, soaking time 4h are added dropwise, so
Beta naphthal and 5% liquid caustic soda mixed solution 80.25g are added dropwise afterwards, controls temperature, after 1 hour drips off, keeps the temperature 2 hours, then with 5% liquid
After alkali 20g tune PH, heat preservation 5h, repetition measurement PH=8, filtering, filter cake is washed with hot water to neutrality.It is small that 1% liquid caustic soda of filter cake is beaten 2
When, filtering, filter cake washs with hot water to neutrality, and filter cake uses 1% hydrochloric acid to be beaten 2 hours again, filters, filter cake with hot water wash to
Neutrality dries to obtain 25.37g, purity 91.99%, yield 96.31%, 0.24 intensity 102.73 of DC 0.22, DH.
Embodiment 6
The synthesis of step 2 pair coupling
In the 500ml four-hole bottles with mechanical agitation, thermometer, the single coupling 15.6g for implementing 1 production, control is added
20 DEG C are added dropwise 30% hydrochloric acid 21g, and 30min is dripped off, and are cooled to 2 DEG C, 20% sodium nitrate solution 27.5g, soaking time 4h are added dropwise, so
Beta naphthal and 5% liquid caustic soda mixed solution 80.25g are added dropwise afterwards, controls temperature, after 1 hour drips off, keeps the temperature 2 hours, then with 5% liquid
After alkali 20g tune PH, heat preservation 5h, repetition measurement PH=8, filtering, filter cake is washed with hot water to neutrality.It is small that 1% liquid caustic soda of filter cake is beaten 2
When, filtering, filter cake washs with hot water to neutrality, and filter cake uses 1% hydrochloric acid to be beaten 2 hours again, filters, filter cake with hot water wash to
Neutrality dries to obtain 25.29g, purity 90.94%, yield 96.01%, 0.58 intensity 99.66 of DC0.61, DH.
Embodiment 7
The synthesis of step 2 pair coupling
In the 500ml four-hole bottles with mechanical agitation, thermometer, the single coupling 15.6g for implementing 1 production, control is added
20 DEG C are added dropwise 30% hydrochloric acid 21g, and 30min is dripped off, and are cooled to 3 DEG C, 20% sodium nitrate solution 27.5g, soaking time 4h are added dropwise, so
Beta naphthal and 5% liquid caustic soda mixed solution 80.25g are added dropwise afterwards, controls temperature, after 1 hour drips off, keeps the temperature 2 hours, then with 5% liquid
After alkali 20g tune PH, heat preservation 5h, repetition measurement PH=8, filtering, filter cake is washed with hot water to neutrality.It is small that 1% liquid caustic soda of filter cake is beaten 2
When, filtering, filter cake washs with hot water to neutrality, and filter cake uses 1% hydrochloric acid to be beaten 2 hours again, filters, filter cake with hot water wash to
Neutrality dries to obtain 25.11g, purity 92.36%, yield 97.23%, 0.11 intensity 96.91 of DC -0.03, DH.
Claims (3)
1. a kind of method preparing solvent red 24, which is characterized in that include the following steps：
Step 1, single coupling reaction：By ortho-aminotoluene, methanol is put into reactor, and 30wt% hydrochloric acid is added dropwise at 20~25 DEG C,
Then cool down, at 2~5 DEG C, 40wt% sodium nitrite solutions are added dropwise, after dripping off, then keeps the temperature 3 hours, rises to room temperature, then keep the temperature
2 hours, soft water is added, stirring, filtering, washing to filtrate pH is in neutrality, dry；
Step 2, double coupling reactions：Single coupling material prepared by ortho-aminotoluene, soft water, step 1, puts into reactor, in 20~
30wt% hydrochloric acid is added dropwise at 25 DEG C, then cools down, at 2~5 DEG C, 20wt% sodium nitrite solutions is added dropwise, after dripping off, then keep the temperature
4 hours, beta naphthal and 5% liquid caustic soda mixed solution are then added dropwise at 2~5 DEG C, after dripping off, keeps the temperature 2 hours, adjusts pH value, heat preservation 5
Hour, repetition measurement PH, filtering, drying after filter cake cleans repeatedly.
2. the as described in claim 1 method for preparing solvent red 24, which is characterized in that in step 1, ortho-aminotoluene and methanol
Mass ratio is 1：0.68~0.91；The mass ratio of ortho-aminotoluene and 30% hydrochloric acid is 1：0.64；Ortho-aminotoluene and 40wt% nitrous
The mass ratio of sour sodium is 1：0.73~0.77, it is warming up to 20~25 DEG C.
3. preparing 24 methods of solvent red as described in claim 1, which is characterized in that in step 2, single coupling material and adjacent toluene
The mass ratio of amine is 1：0.025；The mass ratio of single coupling material and 30wt% hydrochloric acid is 1：1.346；Single coupling material and 20wt% are sub-
The mass ratio of sodium nitrate solution is 1：1.762；The mass ratio of single coupling material and beta naphthal is 1：0.785；Single coupling material and 5% liquid
The mass ratio of alkali is 1：4.48,5% liquid caustic soda tune pH value to 8.
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| CN201810526585.9A CN108659569A (en) | 2018-05-25 | 2018-05-25 | A method of preparing solvent red 24 |
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| CN201810526585.9A CN108659569A (en) | 2018-05-25 | 2018-05-25 | A method of preparing solvent red 24 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116003292A (en) * | 2022-12-12 | 2023-04-25 | 沈阳化工研究院有限公司 | Method for synthesizing amino azobenzene |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1993428A (en) * | 2004-06-01 | 2007-07-04 | 联合色料制造公司 | Aliphatic hydrocarbon soluble red dyes |
-
2018
- 2018-05-25 CN CN201810526585.9A patent/CN108659569A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1993428A (en) * | 2004-06-01 | 2007-07-04 | 联合色料制造公司 | Aliphatic hydrocarbon soluble red dyes |
Non-Patent Citations (1)
| Title |
|---|
| 宋小平 等: "《实用化学品配方手册（十）》", 31 May 1997 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116003292A (en) * | 2022-12-12 | 2023-04-25 | 沈阳化工研究院有限公司 | Method for synthesizing amino azobenzene |
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Application publication date: 20181016 |