CN1285565C - Method for refining 1-nitroanthraquinone by using mixed nitroanthraquinone - Google Patents
Method for refining 1-nitroanthraquinone by using mixed nitroanthraquinone Download PDFInfo
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- CN1285565C CN1285565C CN 200410041198 CN200410041198A CN1285565C CN 1285565 C CN1285565 C CN 1285565C CN 200410041198 CN200410041198 CN 200410041198 CN 200410041198 A CN200410041198 A CN 200410041198A CN 1285565 C CN1285565 C CN 1285565C
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- nitroanthraquinone
- auxiliary agent
- solvent
- refining
- mixing
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- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 238000007670 refining Methods 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 32
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 20
- 238000001953 recrystallisation Methods 0.000 claims abstract description 16
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004202 carbamide Substances 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims description 25
- 239000005864 Sulphur Substances 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract description 10
- 150000004056 anthraquinones Chemical class 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 3
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000012065 filter cake Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- XVMVHWDCRFNPQR-UHFFFAOYSA-N 1,5-dinitroanthracene-9,10-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O XVMVHWDCRFNPQR-UHFFFAOYSA-N 0.000 description 5
- UQKJUEALIQRECQ-UHFFFAOYSA-N 1,6-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)C2=C1C=CC=C2[N+]([O-])=O UQKJUEALIQRECQ-UHFFFAOYSA-N 0.000 description 5
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 description 5
- QCVMOSGPTRRUQZ-UHFFFAOYSA-N 2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 QCVMOSGPTRRUQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- -1 propionic acid ketone Chemical class 0.000 description 2
- OJLABXSUFRIXFL-UHFFFAOYSA-N (2-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 OJLABXSUFRIXFL-UHFFFAOYSA-N 0.000 description 1
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for refining 1-nitroanthraquinone by using mixed nitroanthraquinone, which is characterized in that a solvent and an auxiliary agent are simultaneously added into the mixed nitroanthraquinone with the 1-nitroanthraquinone content of 70-90% for primary recrystallization, the 1-nitroanthraquinone content reaches 97-99%, and the refining yield reaches 80-90%; the solvent is one or two of dimethylformamide or chlorobenzene; the auxiliary agent is one or more of sulfur, sodium nitrite and urea, and the dosage of the auxiliary agent is 0.5-3.0% of the weight of the mixed nitroanthraquinone. Low production cost, high one-time refining rate and simple operation, and is especially suitable for refining 1-nitroanthraquinone from mixed anthraquinone obtained by nitrating anthraquinone in solvent with mixed acid.
Description
Technical field
The present invention relates to a kind of with the method for mixing the refining 1-nitroanthraquinone of nitroanthraquinone.
Background technology
The 1-nitroanthraquinone is important dyestuff intermediate, and the 1-aminoanthraquinone of producing with it can be used for making vat dyes, dispersed dye, reactive dyestuffs and matching stain, also can be used for the synthetic dyestuff intermediate.The 1-nitroanthraquinone also can be directly used in the production dyestuff simultaneously.What adopt usually at present is raw material with the anthraquinone, and with the nitrated preparation 1-nitroanthraquinone of nitration mixture (nitric acid and sulfuric acid), in the resulting mixing nitroanthraquinone, the content of 1-nitroanthraquinone is generally about 80% in solvent medium.Therefore, improve the content that mixes 1-nitroanthraquinone in the nitroanthraquinone, preparation high purity 1-nitroanthraquinone is very necessary.Adopt the method for solvent crystallization in the actual production at present mostly, solvent for use is dimethyl formamide (hereinafter to be referred as DMF), this method does not have waste water and produces, also can obtain high purity 1-nitroanthraquinone, still, because DMF is to mixing 1 in the nitroanthraquinone, 5-dinitroanthraquinone and 1, the solubleness of 6-dinitroanthraquinone is very little, seek out high purity 1-nitroanthraquinone, must be through recrystallization repeatedly.Like this, not only running cost increases, and has also reduced the yield of 1-nitroanthraquinone simultaneously.For improving refining effect, someone has adopted the method that adds auxiliary agent when refining, 1974-55655 has adopted the method for using the mixing nitroanthraquinone in the alkaline purification organic solvent in the presence of catalyst as day disclosure special permission, used catalyst has nitrite, thiocyanate-, iodide, bromide and fluorochemical etc., and used auxiliary agent is a triethylamine; Day disclosure special permission 1974-76853 has adopted the process for purification of making auxiliary agent under the situation that adds initiator in the solvent treatment process with the carbonyl compound more than or two, initiator has Sodium Nitrite or sodium sulfocynanate etc., and used auxiliary agent has metacetone, cyclooctanone, cyclohexanone, propionic acid ketone, acetylacetic ester, diethyl malonate, butanone, methyl phenyl ketone, 3-methyl isophthalic acid-benzene pyrazolone, benzoyl benzophenone, pentanone, diacetylmethane etc.; United States Patent (USP) 3868395 has adopted when solvent treatment and to have added auxiliary agent primary amine, secondary amine or the mixture of the two and carry out the purified method, and the auxiliary agent of choosing has morpholine, diethanolamine etc.; But the amount of auxiliary that above several process for purification adds is too big, and generally between 10～25%, used auxiliary agent price makes production cost higher all than higher.
Summary of the invention
The objective of the invention is to, provide a kind of and make with extra care the method for 1-nitroanthraquinone with mixing nitroanthraquinone, production cost is low, and once refining rate height is easy and simple to handle.
Realize the technical scheme of the object of the invention: a kind of with the method for mixing the refining 1-nitroanthraquinone of nitroanthraquinone, in 1-nitroanthraquinone content is 70～90% mixing nitroanthraquinone, add solvent and auxiliary agent simultaneously and carry out recrystallization one time, 1-nitroanthraquinone content reaches 97～99%, and refining yield reaches 80～90%; Solvent for use is one or both in dimethyl formamide or the chlorobenzene; Adjuvant used is in sulphur, Sodium Nitrite, the urea one or more, and its consumption is for mixing 0.5～3.0% of nitroanthraquinone weight.
In the aforesaid method, add solvent and auxiliary agent simultaneously and carry out secondary recrystallization, 1-nitroanthraquinone content reaches 99.0～99.8%.The 1-nitroanthraquinone that the purity that is obtained is higher like this can satisfy the demand of special purpose.
Above-mentioned when adopting secondary recrystallization to make with extra care the 1-nitroanthraquinone, use the secondary recrystallization mother liquor, as the solvent of a recrystallization, add auxiliary agent simultaneously and carry out recrystallization one time, then, add solvent and auxiliary agent more simultaneously and carry out secondary recrystallization, its refining yield reaches 80～90%.So not only improved the content of 1-nitroanthraquinone but also refining yield is reduced, production cost can not increase yet.
When recrystallizing and refining 1-nitroanthraquinone, add solvent and auxiliary agent simultaneously after, be warming up to 120～150 ℃ and insulated and stirred 1～3 hour.
In aforesaid method, solvent for use and auxiliary agent are commercially available industrial goods.
Aforesaid method is specially adapted to the mixing nitroanthraquinone that obtained with mixed acid nitrification by anthraquinone in solvent.
Technique effect of the present invention: after adopting technical solution of the present invention, mix the dinitroanthraquinone in the nitroanthraquinone, under the synergy of selected solvent of the present invention and auxiliary agent, its solubleness in liquid phase is improved, when crystallisation by cooling, separate with the 1-nitroanthraquinone more thorough, thereby improved the content of 1-nitroanthraquinone, refining yield is also more suitable.Because the determined solvent of technical solution of the present invention and auxiliary agent are commercially available industrial goods, and be cheap, and auxiliary dosage 0.5～3.0% is far below 10～25% consumption in the known technology, and production cost is low.Equipment used and operation all do not have unique requirement during actual making with extra care, and easily grasp easily industrialization.
Embodiment
Below in conjunction with embodiment the present invention is further described in detail, but is not limited to this.
Used mixing nitroanthraquinone is made with mixed acid nitrification in solvent by anthraquinone by processes well known in following examples.
Embodiment 1
In the there-necked flask of 500ml, add and contain 1-nitroanthraquinone 80%, 2-nitroanthraquinone 5%, anthraquinone 2%, 1,5-dinitroanthraquinone 3%, 1,8-dinitroanthraquinone 2%, 1,6-dinitroanthraquinone 4%, 1, the mixing nitroanthraquinone 150g of 7-dinitroanthraquinone 4%, add solvent dimethyl formamide (DMF) 200g, auxiliary agent Sodium Nitrite 2g is warmed up to 140 ℃ of insulated and stirred 3 hours, be cooled to 50 ℃ of filtrations, filter cake is cleaned with DMF again, gets 1-nitroanthraquinone 103g, and its content is 98.5%, refining yield 84.55%, auxiliary dosage is for mixing 1.33% of nitroanthraquinone.
Embodiment 2
In the there-necked flask of 500ml, add and contain 1-nitroanthraquinone 80%, 2-nitroanthraquinone 5%, anthraquinone 2%, 1,5-dinitroanthraquinone 3%, 1,8-dinitroanthraquinone 2%, 1,6-dinitroanthraquinone 4%, 1, the mixing nitroanthraquinone 150g of 7-dinitroanthraquinone 4%, add solvent dimethyl formamide (DMF) 200g, auxiliary agent urea 3g and sulphur 1g are warmed up to 140 ℃ of insulated and stirred 3 hours, be cooled to 50 ℃ of filtrations, filter cake is cleaned with DMF again, gets 1-nitroanthraquinone 108g, and its content is 97.8%, refining yield 88.02%, auxiliary dosage is for mixing 2.67% of nitroanthraquinone.
Embodiment 3
In the there-necked flask of 500ml, add and contain 1-nitroanthraquinone 83%, 2-nitroanthraquinone 5%, anthraquinone 1.5%, 1,5-dinitroanthraquinone 2.5%, 1,8-dinitroanthraquinone 2%, 1,6-dinitroanthraquinone 3%, 1, the mixing nitroanthraquinone 150g of 7-dinitroanthraquinone 3%, add solvent dimethyl formamide (DMF) 100g and chlorobenzene 150g, auxiliary agent Sodium Nitrite 2.5g is warmed up to 140 ℃ of insulated and stirred 3 hours, be cooled to 50 ℃ of filtrations, filter cake is cleaned with DMF again, gets 1-nitroanthraquinone 102g, and its content is 99%, refining yield 81.10%, auxiliary dosage is for mixing 2.0% of nitroanthraquinone.
Embodiment 4
In the there-necked flask of 500ml, add and contain 1-nitroanthraquinone 80%, 2-nitroanthraquinone 5%, anthraquinone 2%, 1,5-dinitroanthraquinone 3%, 1,8-dinitroanthraquinone 2%, 1,6-dinitroanthraquinone 4%, 1, the mixing nitroanthraquinone 150g of 7-dinitroanthraquinone 4% adds solvent dimethyl formamide (DMF) 150g, auxiliary agent Sodium Nitrite 2g, be warmed up to 140 ℃ of insulated and stirred 2 hours, be cooled to 45 ℃ of filtrations, and wash with an amount of DMF, carry out secondary recrystallization in the there-necked flask of the filter cake adding 500ml that obtains, add solvent DMF 100g, auxiliary agent Sodium Nitrite 1g is warmed up to 135 ℃ of insulated and stirred 2 hours, be cooled to 50 ℃ of filtrations, filter cake is cleaned with DMF, gets 1-nitroanthraquinone 94g, and its content is 99.6%, refining yield 78%, the total consumption of auxiliary agent is for mixing 2.0% of nitroanthraquinone.
Embodiment 5
In the there-necked flask of 500ml, add and contain 1-nitroanthraquinone 80%, 2-nitroanthraquinone 5%, anthraquinone 2%, 1,5-dinitroanthraquinone 3%, 1,8-dinitroanthraquinone 2%, 1,6-dinitroanthraquinone 4%, 1, the mixing nitroanthraquinone 150g of 7-dinitroanthraquinone 4%, the two smart mother liquor 150g that add among the embodiment 4 make solvent, auxiliary agent Sodium Nitrite 2g, be warmed up to 140 ℃ of insulated and stirred 2 hours, be cooled to 50 ℃ of filtrations, and wash with an amount of DMF, the filter cake that obtains adds in the there-necked flask of 500ml, add solvent DMF 100g, auxiliary agent Sodium Nitrite 1g is warmed up to 120～150 ℃ of insulated and stirred 2 hours, be cooled to 45 ℃ of filtrations, filter cake is cleaned with DMF, gets 1-nitroanthraquinone 106g, and content is greater than 99.5%, refining yield 87.89%, the total consumption of auxiliary agent is for mixing 2.0% of nitroanthraquinone.
The present invention makes with extra care the method for 1-nitroanthraquinone with mixing nitroanthraquinone, and cost is low, and the high and refining yield height of 1-nitroanthraquinone content is easy and simple to handle, practical.
Claims (4)
1, a kind of with the method for mixing the refining 1-nitroanthraquinone of nitroanthraquinone, it is characterized in that: in 1-nitroanthraquinone content is 70～90% mixing nitroanthraquinone, add solvent and auxiliary agent simultaneously and carry out recrystallization one time, 1-nitroanthraquinone content reaches 97～99%, and refining yield reaches 80～90%; Solvent for use is one or both in dimethyl formamide or the chlorobenzene; Adjuvant used is in sulphur, Sodium Nitrite, the urea one or more, and its consumption is for mixing 0.5～3.0% of nitroanthraquinone weight.
2, method according to claim 1 is characterized in that: add solvent and auxiliary agent simultaneously and carry out secondary recrystallization, 1-nitroanthraquinone content reaches 99.0～99.8%.
3, method according to claim 2 is characterized in that: use the secondary recrystallization mother liquor, as the solvent of a recrystallization, add auxiliary agent simultaneously and carry out recrystallization one time, then, add solvent and auxiliary agent more simultaneously and carry out secondary recrystallization, its refining yield reaches 80～90%.
4, method according to claim 1 and 2 is characterized in that: after adding solvent and auxiliary agent simultaneously, be warming up to 120～150 ℃ and insulated and stirred 1～3 hour.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200410041198 CN1285565C (en) | 2004-07-05 | 2004-07-05 | Method for refining 1-nitroanthraquinone by using mixed nitroanthraquinone |
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| CN 200410041198 CN1285565C (en) | 2004-07-05 | 2004-07-05 | Method for refining 1-nitroanthraquinone by using mixed nitroanthraquinone |
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| CN1594440A CN1594440A (en) | 2005-03-16 |
| CN1285565C true CN1285565C (en) | 2006-11-22 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101391963B (en) * | 2008-10-15 | 2012-04-25 | 山东大学 | Method for comprehensively utilizing 1-nitroanthraquinone waste residue |
| CN102320979B (en) * | 2011-05-25 | 2014-01-29 | 盐城市瓯华化学工业有限公司 | Resource utilization method of waste residues generated by 1-nitroanthraquinone production by solvent method |
| CN103435492B (en) * | 2013-07-30 | 2015-04-08 | 南京理工大学 | Method for synthesizing 1-nitroanthraquinone by nitration of nitrogen pentoxide |
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Owner name: JIANGSU YABANG DYE CO., LTD. Free format text: FORMER OWNER: GUANGZHOU YABANG FINE CHEMICALS CO., LTD. Effective date: 20061201 |
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Effective date of registration: 20061201 Address after: 213163, No. 105, Renmin West Road, Niu Tong Town, Wujin District, Jiangsu, Changzhou Patentee after: Jiangsu Yabang Dye Co.,Ltd. Address before: 213163 Jiangsu city in Changzhou Province, the South Gate Bridge in Changzhou Niutang Yabang Fine Chemical Co. Patentee before: GUANGZHOU YABANG FINE CHEMICAL |
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Granted publication date: 20061122 |