CN101565556B - Preparation method for solvent orange 60 - Google Patents
Preparation method for solvent orange 60 Download PDFInfo
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- CN101565556B CN101565556B CN200910301060A CN200910301060A CN101565556B CN 101565556 B CN101565556 B CN 101565556B CN 200910301060 A CN200910301060 A CN 200910301060A CN 200910301060 A CN200910301060 A CN 200910301060A CN 101565556 B CN101565556 B CN 101565556B
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- solvent orange
- polar organic
- organic solvent
- solvent
- hydrochloric acid
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- XFYQEBBUVNLYBR-UHFFFAOYSA-N O=C(c1ccccc1C1=N2)N1c1cccc3c1c2ccc3 Chemical compound O=C(c1ccccc1C1=N2)N1c1cccc3c1c2ccc3 XFYQEBBUVNLYBR-UHFFFAOYSA-N 0.000 description 1
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention discloses a preparation method for solvent orange 60, belonging to chemical industry field, manufactured by: mixing phthalic anhydride and 1, 8-naphthylenediamine with the mass ratio of 1:1 with 1-5% by mass of hydrochloric acid solution, polar organic solvent miscible with water and non-ionic active catalyst, stirring and heating to the refluxing state for reacting 8-15 hours, filtering, washing the filter cake with water till the pH value of the filtrate is neutral, drying to obtain the solvent orange 60, wherein the dosage of the hydrochloric acid solution is 10-20 times of the 1, 8-naphthylenediamine; the dosage of the polar organic solvent is 1-50% of the total amount of the reaction medium and the dosage of the catalyst is 0.01-2% of the total amount of the reaction medium. The method combines the advantages of good quality and low cost of water phase method.
Description
Technical field
The present invention relates to a kind of preparation method of solvent orange 60, belong to chemical field.
Background technology
Solvent orange 60, English name Solvent Orange 60, molecular formula: C18H10N2O, molecular weight: 270.29, CAS number: 6925-69-5.Outward appearance is the safran powder, and is water insoluble, is slightly soluble in organic solvents such as ethanol, benzene,toluene,xylene.Be mainly used in PS, ABS resin.Its structural formula is:
Difference according to used reaction medium in the preparation process of existing solvent orange 60 is divided into solvent method and water method.Solvent method is to be a kind of method that reaction medium is produced solvent orange 60 with the polar organic solvent; The product vividness that this method is produced is high; Quality product is higher, but because solvent orange 60 has certain solubleness in organic solvent, so product separation is difficult relatively; Add that solvent needs to reclaim, so production cost is higher.The water method is to be a kind of method that reaction medium is produced the solvent orange with the aqueous hydrochloric acid, only just need filter and can realize product separation, and reaction medium need not to reclaim; Only need neutralizing treatment; Therefore production cost is lower, but the product vividness that this method is produced is relatively low, and quality product is relatively poor.
Summary of the invention
The purpose of this invention is to provide a kind of good product quality, the preparation method of the solvent orange 60 that production cost is low.
Technical scheme of the present invention: a kind of preparation method of solvent orange 60; Band stir and the reaction unit of refluxing unit in be 1: 1 Tetra hydro Phthalic anhydride and 1 with the amount of substance ratio; 8-naphthylene diamine and mass concentration are 1～5% hydrochloric acid soln, can mix with miscible polar organic solvent and the nonionic active catalyst of water; Open and stir and heating, be warming up under the reflux state and reacted 8～15 hours, filter then; Filter cake use clear water be washed till filtrating pH value be neutrality, final drying promptly gets solvent orange 60; The consumption of said hydrochloric acid soln is 1,10～20 times of 8-naphthylene diamine; The consumption of said polar organic solvent is 1～50% of a reaction medium total amount; Said catalyst levels is 0.01～2% of a reaction medium total amount.
Said polar organic solvent is acetic acid or N (DMF) or alcohol or N-Methyl pyrrolidone.
Said nonionic active catalyst is AEO or TX10.
Said TX10 is a polyoxyethylene nonylphenol.
Reaction equation of the present invention is following:
AEO of the present invention belongs to nonionogenic tenside, and its chemical general formula is RO (CH
2CH
2O)
nH, wherein, R is generally the alkyl of 10～15 carbon, and n can be 2～30 integer.
TX10 of the present invention belongs to nonionogenic tenside, and its general structure does
Wherein, R is generally the alkyl of 8～12 carbon, and n can be 2～50 integer, and the present invention has adopted modal polyoxyethylene nonylphenol as the nonionic active catalyst, and its chemistry is C
9H
19C
6H
4O (CH
2CH
2O) nH, wherein n is 5 to 20 a integer.
AEO and TX10 belong to nonionogenic tenside together; Has similar performance; According to its HLB value of adjustable size joint of n value, thereby make it have good emulsifying property, wettability, dispersiveness, lyotropy, soil removability and penetrating power.In the present invention, AEO and TX10 are as catalyzer.
The present invention combines original solvent method with the water method; Both avoided the deficiency that difficulty, solvent need to reclaim relatively, production cost is high of product separation in the solvent method; Also avoided relatively low, the second-rate shortcoming of product vividness in the water method; But reached the best result that the product vividness is high, production cost is low, promoted the lifting of product specification greatly and reduced the enterprise production cost.
Embodiment
Embodiment 1
In the there-necked flask of band stirring and reflux condensing tube, add 200g 3% aqueous hydrochloric acid, 30g alcohol, 10g Tetra hydro Phthalic anhydride, 10.7g 1 successively; 8-naphthylene diamine, 0.3g AEO; Open and stir, be warming up to the little reflux state of reaction system, react 8 hours after-filtration; Filter cake is washed till filtrating with clear water and is neutral, dry product 17.5g (be theoretical yield 95.9%).Product is compared coloured light approximate (specifically seeing table 1) with standard substance, intensity is 99.0%.
Table 1
(wherein: Δ E-aberration, Δ H-tonal difference, Δ L-luminosity equation, Δ C-chroma is poor,
The green degree of the red degree of Δ a-is poor, and Δ b-Huang degree indigo plant degree is poor, and more for a short time product coloured light and the standard substance of showing of Δ E are approaching more.Usually, Δ E promptly meets the demands less than 3, if requirement is more strict, then Δ E should be less than 1.)
Embodiment 2
In the 2000L enamel reaction still of stirring of band frame and reflux exchanger, add 1000kg 5% aqueous hydrochloric acid, 100kg N (DMF), 100kg Tetra hydro Phthalic anhydride, 107kg 1 successively; 8-naphthylene diamine, 5kg polyoxyethylene nonylphenol; Open and stir, be warming up under the little reflux state of reaction system, react 12 hours after-filtration; Filter cake is washed till filtrating with clear water and is neutral, dry product 177kg (be theoretical yield 96.8%).Product is compared approximate (specifically seeing table 2) with standard substance, intensity is 101.0%.
Table 2
| Light source | ΔE * | ΔH * | ΔC * | ΔL * | Δa * | Δb * |
| D65/10 | 0.32 | 0.22 | -0.12 | -0.20 | -0.25 | 0.01 |
| A/10 | 0.34 | 0.20 | -0.15 | -0.23 | -0.25 | -0.05 |
| F2/10 | 0.30 | 0.21 | -0.05 | -0.21 | -0.22 | 0.01 |
Embodiment 3
The hydrochloric acid soln, 60kg acetic acid, 20kg Tetra hydro Phthalic anhydride, the 21.4kg1 that in the 500L enamel reaction still of stirring of band frame and reflux exchanger, add 300kg 1% successively; 8-naphthylene diamine, 5kg polyoxyethylene nonylphenol; Open and stir, be warming up under the little reflux state of reaction system, react 8 hours after-filtration; Filter cake is washed till filtrating with clear water and is neutral, dry product 35kg (be theoretical yield 95.7%).Product is compared approximate (specifically seeing table 3) with standard substance, intensity is 98.9%.
Table 3
| Light source | ΔE * | ΔH * | ΔC * | ΔL * | Δa * | Δb * |
| D65/10 | 0.45 | 0.35 | -0.07 | -0.27 | -0.34 | 0.11 |
| A/10 | 0.47 | 0.34 | -0.11 | -0.31 | -0.36 | 0.04 |
| F2/10 | 0.42 | 0.33 | 0.04 | -0.26 | -0.30 | 0.13 |
Embodiment 4
The hydrochloric acid soln, 20kgN-SL 1332,20kg Tetra hydro Phthalic anhydride, the 21.4kg1 that in the 500L enamel reaction still of stirring of band frame and reflux exchanger, add 300kg 3% successively; 8-naphthylene diamine, 1kg polyoxyethylene nonylphenol; Open and stir, be warming up under the little reflux state of reaction system, react 10 hours after-filtration; Filter cake is washed till filtrating with clear water and is neutral, dry product 36kg (be theoretical yield 95.7%).Product is compared approximate (specifically seeing table 3) with standard substance, intensity is 101.8%.
Table 4
| Light source | ΔE * | ΔH * | ΔC * | ΔL * | Δa * | Δb * |
| D65/10 | 0.68 | -0.23 | 0.45 | 0.45 | 0.42 | 0.28 |
| A/10 | 0.77 | -0.23 | 0.53 | 0.51 | 0.43 | 0.39 |
| F2/10 | 0.65 | -0.20 | 0.40 | 0.47 | 0.31 | 0.32 |
Claims (2)
1. the preparation method of a solvent orange 60; It is characterized in that: band stir and the reaction unit of refluxing unit in amount of substance than be the Tetra hydro Phthalic anhydride of 1:1 and 1,8-naphthylene diamine and mass concentration are 1～5% hydrochloric acid soln, can mix with miscible polar organic solvent and the nonionic active catalyst of water, the unlatching stirring is also heated; Be warming up under the reflux state and reacted 8～15 hours; Filter then, filter cake uses clear water to be washed till filtrating pH value to be neutrality, and final drying promptly gets solvent orange 60; The consumption of said hydrochloric acid soln is 1,10 ~ 20 times of 8-naphthylene diamine; The consumption of said polar organic solvent is 1 ~ 50% of a reaction medium total amount; Said catalyst levels is 0.01 ~ 2% of a reaction medium total amount; Said polar organic solvent is acetic acid or N (DMF) or alcohol or N-Methyl pyrrolidone; Said nonionic active catalyst is AEO or TX10.
2. the preparation method of a kind of solvent orange 60 according to claim 1 is characterized in that said TX10 is a polyoxyethylene nonylphenol.
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| CN200910301060A CN101565556B (en) | 2009-03-23 | 2009-03-23 | Preparation method for solvent orange 60 |
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|---|---|---|---|
| CN200910301060A CN101565556B (en) | 2009-03-23 | 2009-03-23 | Preparation method for solvent orange 60 |
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| CN101565556B true CN101565556B (en) | 2012-10-17 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103275515B (en) * | 2013-06-18 | 2014-10-29 | 海宁市现代化工有限公司 | Orange naphtocyclinon dye and preparation method thereof |
| CN107474053B (en) * | 2017-08-28 | 2019-06-11 | 宁波龙欣精细化工有限公司 | The preparation method of Yi Zhong piceneketone type solvent dye |
| CN109762362A (en) * | 2019-01-22 | 2019-05-17 | 南通龙翔新材料科技股份有限公司 | The preparation method of pyrene ketones solvent dyestuff |
| CN111019542A (en) * | 2019-10-28 | 2020-04-17 | 深圳昌茂粘胶新材料有限公司 | Mute black mobile phone internal explosion-proof membrane material and preparation method thereof |
| CN112592603A (en) * | 2020-12-22 | 2021-04-02 | 安徽清科瑞洁新材料有限公司 | Green method for preparing solvent orange 60 with low pollution |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0639624A1 (en) * | 1993-08-19 | 1995-02-22 | Bayer Ag | Phthaloperinone dyestuffs |
| DE19548411A1 (en) * | 1995-12-22 | 1997-06-26 | Bayer Ag | Preparation of poly:cyclic N=heterocyclic compounds of perinone type with high productivity and selectivity |
| US5830931A (en) * | 1995-12-22 | 1998-11-03 | Bayer Aktiengesellschaft | Process for the preparation of polycyclic compounds |
| CN1379064A (en) * | 2001-03-29 | 2002-11-13 | 拜尔公司 | New crystal shape of dyestuff peri-ketone |
-
2009
- 2009-03-23 CN CN200910301060A patent/CN101565556B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0639624A1 (en) * | 1993-08-19 | 1995-02-22 | Bayer Ag | Phthaloperinone dyestuffs |
| DE19548411A1 (en) * | 1995-12-22 | 1997-06-26 | Bayer Ag | Preparation of poly:cyclic N=heterocyclic compounds of perinone type with high productivity and selectivity |
| US5830931A (en) * | 1995-12-22 | 1998-11-03 | Bayer Aktiengesellschaft | Process for the preparation of polycyclic compounds |
| CN1379064A (en) * | 2001-03-29 | 2002-11-13 | 拜尔公司 | New crystal shape of dyestuff peri-ketone |
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| CN101565556A (en) | 2009-10-28 |
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