CN105541648A - Synthetic method for precursor of anthraquinone reactive disperse dye used in supercritical CO2 - Google Patents

Synthetic method for precursor of anthraquinone reactive disperse dye used in supercritical CO2 Download PDF

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CN105541648A
CN105541648A CN201510918478.7A CN201510918478A CN105541648A CN 105541648 A CN105541648 A CN 105541648A CN 201510918478 A CN201510918478 A CN 201510918478A CN 105541648 A CN105541648 A CN 105541648A
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supercritical
reaction
reactive disperse
chloroanthraquinone
synthetic method
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CN105541648B (en
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龙家杰
章燕琴
於琴
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Suzhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Abstract

The invention specifically relates to a synthetic method for a precursor of an anthraquinone reactive disperse dye used in supercritical CO2, which belongs to the technical field of dyes. According to the method, 1-chloroanthraquinone and 2,5-diaminotoluene sulfate are used as raw materials, K2CO3 is used as an acid-binding agent, and CuI is used as a reaction catalyst, a heating reflux reaction is carried out at 80 to 140 DEG C for 6 to 14 h under the protection of nitrogen; and after completion of the reaction, post-treatment is carried out so as to obtain solid powder of the dye precursor. The method has the advantages of a low usage amount of the catalyst, mild reaction conditions, high yield and low cost, and the obtained precursor has good applicability; and the method is applicable to synthesis of the anthraquinone reactive disperse dye used in supercritical CO2 and to synthesis of reactive disperse dyes used in conventional water-bath dyeing.

Description

A kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma
Technical field
The invention belongs to technical field of dye, be specifically related to a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma.
Background technology
Appearance and the development of reactive disperse dyes can trace back to the sixties in last century five, but because its impact by working conditions is larger, be difficult to when dyeing to polyester/cotton blended fabric accomplish dye evenly, applicability is poor, thus encounter in evolution bottleneck (reference: the significant progress of reactive dyestuffs and fundamental research achievement [J] in ISUZU company. dyestuff and dyeing, 2008,2:1-9,44.).And utilize supercritical CO 2fluid staining technique can realize the dyeing of reactive disperse dyes to polyester/cotton blended fabric and natural fiber, for its development is filled with new vitality (reference: One-bathdyeingofpolyester/cottonblendswithreactivedisper sedyesinsupercriticalcarbondioxide [J] .TextileResearchJournal, 2004,74 (11): 989-994; Technical Progress in Modem Reactive Dyestuffs [J]. printing and dyeing, 2004,2:37-42; In supercritical co, reactive disperse dyes is to the dyeing [J] of natural fiber. Overseas Textile Industry technology: the dyeing and finishing of textile needle woven garment chemical fibre, 2003,9:22-27.).
In reactive disperse dyes synthesis, the report about anthraquinone ring is less, and method is also comparatively single, is generally introduce active group on the basis of existing dispersed dye, of less types.
Utilize Ullmann to react the synthesis carrying out dyestuff or dyestuff intermediate to have been reported before this, but the dyestuff related to mainly vat dyes, commonly aminoanthraquinone and chloroanthraquinone carry out condensation reaction under catalyst action, thus on anthraquinone core, introduce imino-generation anthraquinone group with imine moiety, or by generating C-C, prepare some condensed ring vat dyes; Ullmann reaction also has important application in matching stain, generally take bromamine acid as raw material, react with substituted aromatic amines in alkaline aqueous solution (reference: the application of ullmann reaction in Dyestuff synthesis [J]. dyestuffs industries, 1984,3:1-7.), and it did not have report in water-insoluble active dispersed dye.
Thus, how to make the synthetic method diversification of reactive disperse dyes, solve the problems such as reactive disperse dyes kind is few, applicability is not strong, become the key of breakthrough bottleneck, and can be supercritical CO 2in fluid, the non-aqueous dyeing of natural fiber provides more vast potential for future development.
Summary of the invention
For solving the problems of the technologies described above, the present invention by Ullmann reactive applications in supercritical CO 2with the synthesis of anthraquinone type reactive disperse dyes presoma, in reaction process, catalyst levels is few, reaction conditions is gentle, and productive rate is higher, and cost is lower, and the presoma applicability obtained is strong, except being suitable for supercritical CO 2with the synthesis of anthraquinone type reactive disperse dyes, be also suitable for the synthesis of conventional water-bath dyeing reactive disperse dyes.
A kind of supercritical CO that the present invention proposes 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, comprise the following steps:
(1) with 1-chloroanthraquinone and 2,5-diaminotoluene sulphate for raw material, K 2cO 3for acid binding agent, CuI is catalysts, under nitrogen protection condition in reaction medium reflux 6 ~ 14h, temperature of reaction is 80 ~ 140 DEG C, and wherein the mol ratio ratio of 2,5-diaminotoluene sulphates and 1-chloroanthraquinone is 1 ~ 2, acid binding agent K 2cO 3with the mol ratio ratio of 1-chloroanthraquinone be 1.5 ~ 4, Catalysts Cu I and the mol ratio ratio of 1-chloroanthraquinone be 0.056 ~ 0.333;
(2) after reaction terminates, the reaction solution of step (1) is cooled to 35 DEG C, add water and methylene dichloride that volume ratio is 2:1, use flocculating aids, pressure filtration, to remove the black flocks in mixed solution, then carry out extracting, wash, revolve steaming, vacuum-drying, thus obtain the pressed powder of dye precursor.
Further, the reaction medium in described step (1) is the one or both arbitrary proportion mixture in DMF, dimethyl sulfoxide (DMSO).
Further, the consumption of described reaction medium is 6mL/mmol1-chloroanthraquinone.
Further, the flocculating aids in described step (2) is neutral silica gel, specification 200 ~ 300 order.
The chemical equation that the present invention relates to is as follows:
Catalysts Cu I elder generation and 1-chloroanthraquinone generation oxidative addition in the present invention, generate the intermediate with [Cu], nucleophilic reagent 2,5-diaminotoluene sulphate is (at acid binding agent K subsequently 2cO 3under existent condition, nucleophilicity increases) with intermediate generation nucleophilic substitution reaction slough [Cu] (reference: CatalyticC-C, C-N, andC-OUllmann-TypeCouplingReactions [J] .AngewandteChemieInternationalEdition,, thus obtain dye precursor 2009,48 (38): 6954-6971.), operation steps is simple, is easy to control.
Above-mentioned explanation is only the general introduction of technical solution of the present invention, in order to better understand technique means of the present invention, and can be implemented according to the content of specification sheets, be below preferred embodiment of the present invention, and coordinate accompanying drawing, be described in detail as follows.
Accompanying drawing explanation
Fig. 1 is LC-MS spectrogram in the embodiment of the present invention 1;
Fig. 2 is hydrogen nuclear magnetic resonance spectrogram in the embodiment of the present invention 1;
Fig. 3 is FTIR spectrum figure in the embodiment of the present invention 1.
Embodiment
Below in conjunction with drawings and Examples, the specific embodiment of the present invention is described in further detail.Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.
Embodiment 1
Supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, comprise the steps:
(1) in 100mL there-necked flask (thermometer, prolong and dropping funnel being housed, with nitrogen protection device above prolong), 0.005mol2 is added, 5-diaminotoluene sulphate and 0.0075molK 2cO 3, pass into nitrogen, and add 0.556mmolCuI rapidly.Take 0.005mol1-chloroanthraquinone, add 30mLN, dinethylformamide dissolves (if there is trace solid insoluble, ultra-sonic oscillation can be adopted to being yellow transparent shape), and join rapidly in dropping funnel, open and stir and slowly drip (within about 10 minutes, dripping off), start timing when being warming up to 100 DEG C, reflux 12 hours.
(2) after reaction terminates, reaction solution is naturally cooled to 35 DEG C, add water and methylene dichloride (volume ratio is 2:1), take neutral silica gel as flocculating aids, pressure filtration, to remove the black flocks in mixed solution, then carries out extracting, washes, revolves the operations such as steaming, vacuum-drying, thus obtaining the pressed powder of dye precursor, productive rate is 44.34%.
Carry out purifying to the pressed powder of the dye precursor obtained in embodiment, and the structure of carrying out product characterizes, its method comprises:
1. with column layer chromatography silicone rubber (200 ~ 300 order) for stationary phase, methylene dichloride and normal hexane (volume ratio is 1:1) are moving phase, dry column-packing, pressurized operation; Tlc silica gel plate G-254, developping agent is acetone and normal hexane (volume ratio is 1:2).
2. utilize LC-MS (positive ion mode, ESI source), proton nmr spectra (400MHz, DMSO-d 6) and the measuring technology such as FTIR spectrum structural characterization is carried out to the product obtained in the present embodiment, its result is as shown in Figures 1 to 3.
Shown by Fig. 1, LC-MS (positive ion mode, ESI source) can detect molecular ion peak [M+H] +=329.1286, conform to the molecular weight of dye precursor.
In Fig. 2:
1HNMR(400MHz,DMSO-d 6):δ11.05,10.85(s,1H,8-NH,8’-NH),8.24(t,J＝6.5Hz,1H,Ar-1H,Ar-1’H),8.15(d,J＝7.3Hz,1H,Ar-4H,Ar-4’H),7.99-7.81(m,2H,Ar-2H,Ar-2’H,Ar-3H,Ar-3’H),7.56(dd,J＝10.6,5.0Hz,1H,Ar-6H,Ar-6’H),7.48(d,J＝7.0Hz,1H,Ar-5H,Ar-5’H),6.92(dd,J＝17.1,8.4Hz,2H,Ar-7H,Ar-7’H,Ar-11H,Ar-9’H),6.70(d,J＝8.2Hz,1H,Ar-9H,Ar-10’H),6.60-6.45(m,1H,Ar-10H,Ar-11’H),5.16,4.98(s,2H,12’-NH 2,12-NH 2),2.08(d,J＝11.9Hz，3H,13-CH 3,13’-CH 3)。Show in gained dye precursor and isometry body structure thereof thus, respectively 1the ownership of H and consistent in theoretical construct.
Fig. 3 shows, at 3465.43cm -1, 3373.64cm -1and 1624.42cm -1there is NH respectively in place 2antisymmetric stretching vibration peak, symmetrical stretching vibration peak and flexural vibration peak, at 3242.83cm -1there is the stretching vibration peak of secondary amine N-H in place, at 2920.94cm -1, 2856.30cm -1and 1368.50cm -1there is CH respectively in place 3antisymmetric stretching vibration peak, symmetrical stretching vibration peak and symmetric deformation vibration peak, at 1657.66cm -1there is the stretching vibration peak of C=O in place.Show that the chlorine atom on 1-chloroanthraquinone replaced by the amino in 2,5-diaminotoluene sulphate thus.
The detected result display of Fig. 1 ~ 3, the structure of gained dye precursor conforms to desired design structure.
Embodiment 2
The present embodiment provides a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, other steps of the method are with embodiment 1.Reaction medium wherein in step (1) is 30mL dimethyl sulfoxide (DMSO); In step (2), the productive rate of dye precursor is 37.03%.
Embodiment 3
The present embodiment provides a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, other steps of the method are with embodiment 1.Wherein 2,5-diaminotoluene sulphates and K in step (1) 2cO 3consumption be respectively 0.0075mol and 0.015mol, temperature of reaction is 110 DEG C, and the reaction times is 6h; In step (2), the productive rate of dye precursor is 38.79%.
Embodiment 4
The present embodiment provides a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, other steps of the method are with embodiment 3.Reaction times wherein in step (1) is 14h; In step (2), the productive rate of dye precursor is 67.84%.
Embodiment 5
The present embodiment provides a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, other steps of the method are with embodiment 1.Wherein 2,5-diaminotoluene sulphates, K in step (1) 2cO 3be respectively 0.0075mol, 0.020mol and 1.667mmol with the consumption of CuI, temperature of reaction is 80 DEG C, reaction times 10h; In step (2), the productive rate of dye precursor is 33.80%.
Embodiment 6
The present embodiment provides a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, other steps of the method are with embodiment 1.Wherein 2,5-diaminotoluene sulphates and K in step (1) 2cO 3consumption be respectively 0.0075mol and 0.015mol, temperature of reaction is 140 DEG C; In step (2), the productive rate of dye precursor is 62.67%.
Embodiment 7
The present embodiment provides a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, other steps of the method are with embodiment 1.Wherein 2,5-diaminotoluene sulphates and K in step (1) 2cO 3consumption be respectively 0.010mol and 0.0125mol; In step (2), the productive rate of dye precursor is 62.99%.
Embodiment 8
The present embodiment provides a kind of supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, other steps of the method are with embodiment 1.Wherein 2,5-diaminotoluene sulphates, K in step (1) 2cO 3be respectively 0.0075mol, 0.015mol and 0.278mmol with the consumption of CuI, temperature of reaction is 100 DEG C, and the reaction times is 8h; In step (2), the productive rate of dye precursor is 68.03%.
Shown by embodiments of the invention 1 ~ 8: each reaction conditions all has impact to dye precursor productive rate, wherein the effect of acid binding agent consumption is the most obvious, increases K 2cO 3consumption can make the nucleophilicity of 2,5-diaminotoluene sulphate increase, and be conducive to the carrying out reacted, the productive rate of dye precursor significantly improves; When the mol ratio ratio of Catalysts Cu I and 1-chloroanthraquinone is 0.056, control other reaction conditionss, can make productive rate more than 65%, catalyst levels is few, and cost is lower; When temperature of reaction is 110 DEG C, when return time is 8h, control the consumption of each reactant, productive rate can be made to reach more than 85%, reaction conditions is gentle, and productive rate is high, and applicability is strong.Meanwhile, detected result also demonstrate that the structure of gained dye precursor conforms to expected structure.
In sum, the present invention by Ullmann reactive applications in supercritical CO 2in synthesis with anthraquinone type reactive disperse dyes presoma, the synthesis for anthraquinone type reactive disperse dyes provides a kind of new way, and in reaction process, catalyst levels is few, reaction conditions is gentle, and productive rate is higher, and cost is lower, and applicability is strong.
The above is only the preferred embodiment of the present invention; be not limited to the present invention; should be understood that; for those skilled in the art; under the prerequisite not departing from the technology of the present invention principle; can also make some improvement and modification, these improve and modification also should be considered as protection scope of the present invention.

Claims (4)

1. a supercritical CO 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, it is characterized in that comprising the steps:
(1) with 1-chloroanthraquinone and 2,5-diaminotoluene sulphate for raw material, K 2cO 3for acid binding agent, CuI is catalysts, under nitrogen protection condition in reaction medium reflux 6 ~ 14 hours, temperature of reaction is 80 ~ 140 DEG C, and wherein the mol ratio ratio of 2,5-diaminotoluene sulphates and 1-chloroanthraquinone is 1 ~ 2, acid binding agent K 2cO 3with the mol ratio ratio of 1-chloroanthraquinone be 1.5 ~ 4, Catalysts Cu I and the mol ratio ratio of 1-chloroanthraquinone be 0.056 ~ 0.333;
(2) after reaction terminates, the reaction solution of step (1) is cooled to 35 DEG C, add water and methylene dichloride that volume ratio is 2:1, use flocculating aids, pressure filtration, to remove the black flocks in mixed solution, then carry out extracting, wash, revolve steaming, vacuum-drying, thus obtain the pressed powder of dye precursor.
2. a kind of supercritical CO according to claim 1 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, it is characterized in that: the reaction medium in described step (1) is the one or both arbitrary proportion mixture in DMF, dimethyl sulfoxide (DMSO).
3. a kind of supercritical CO according to claim 2 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, it is characterized in that: the consumption of described reaction medium is 6mL/mmol1-chloroanthraquinone.
4. a kind of supercritical CO according to claim 1 2by the synthetic method of anthraquinone type reactive disperse dyes presoma, it is characterized in that: the flocculating aids in described step (2) is neutral silica gel, specification 200 ~ 300 order.
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CN107057401A (en) * 2017-04-21 2017-08-18 苏州大学 Dichloro s-triazine type reactive disperse dyes based on anthraquinone and preparation method thereof
CN108586274A (en) * 2018-05-25 2018-09-28 苏州大学 A kind of presoma and preparation method thereof of blue anthraquinone reactive disperse dyes
WO2019223016A1 (en) * 2018-05-25 2019-11-28 苏州大学张家港工业技术研究院 Blue anthraquinone active disperse dye and preparation method therefor
WO2019223015A1 (en) * 2018-05-25 2019-11-28 苏州大学张家港工业技术研究院 Precursor of blue anthraquinone active disperse dye and preparation method therefor
CN111424444A (en) * 2020-05-21 2020-07-17 浙江爱利斯染整有限公司 Composition for supercritical dyeing and application thereof
WO2021248809A1 (en) * 2020-06-08 2021-12-16 浙江越新印染有限公司 Red dye composition and use thereof for supercritical carbon dioxide waterless dyeing

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107057401A (en) * 2017-04-21 2017-08-18 苏州大学 Dichloro s-triazine type reactive disperse dyes based on anthraquinone and preparation method thereof
CN107057401B (en) * 2017-04-21 2019-03-15 苏州大学 Dichloro s-triazine type reactive disperse dyes based on anthraquinone and preparation method thereof
CN108586274A (en) * 2018-05-25 2018-09-28 苏州大学 A kind of presoma and preparation method thereof of blue anthraquinone reactive disperse dyes
WO2019223016A1 (en) * 2018-05-25 2019-11-28 苏州大学张家港工业技术研究院 Blue anthraquinone active disperse dye and preparation method therefor
WO2019223015A1 (en) * 2018-05-25 2019-11-28 苏州大学张家港工业技术研究院 Precursor of blue anthraquinone active disperse dye and preparation method therefor
CN111424444A (en) * 2020-05-21 2020-07-17 浙江爱利斯染整有限公司 Composition for supercritical dyeing and application thereof
WO2021248809A1 (en) * 2020-06-08 2021-12-16 浙江越新印染有限公司 Red dye composition and use thereof for supercritical carbon dioxide waterless dyeing

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