CN104725897B - A kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate - Google Patents
A kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate Download PDFInfo
- Publication number
- CN104725897B CN104725897B CN201310718981.9A CN201310718981A CN104725897B CN 104725897 B CN104725897 B CN 104725897B CN 201310718981 A CN201310718981 A CN 201310718981A CN 104725897 B CN104725897 B CN 104725897B
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- dyestuff intermediate
- ecological
- nitroanilines
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000975 dye Substances 0.000 title claims abstract description 69
- 230000007613 environmental effect Effects 0.000 title claims abstract description 12
- 230000001681 protective effect Effects 0.000 title claims abstract description 10
- 238000003672 processing method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000000967 suction filtration Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
- BVWCFOXBDSMXEP-UHFFFAOYSA-N 1-(5-acetyl-2-methoxyphenyl)-3-methylbutan-1-one Chemical compound COC1=CC=C(C(C)=O)C=C1C(=O)CC(C)C BVWCFOXBDSMXEP-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 3
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical group NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 claims description 3
- -1 hexamethylene Alkane Chemical class 0.000 claims description 3
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical class ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 claims description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical class [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 235000012544 Viola sororia Nutrition 0.000 claims description 2
- 241001106476 Violaceae Species 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- WZWSOGGTVQXXSN-UHFFFAOYSA-N cyclohexanone;toluene Chemical compound CC1=CC=CC=C1.O=C1CCCCC1 WZWSOGGTVQXXSN-UHFFFAOYSA-N 0.000 claims description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 2
- RTQPWAMKFSLHMT-UHFFFAOYSA-N n-bromo-4-nitroaniline Chemical class [O-][N+](=O)C1=CC=C(NBr)C=C1 RTQPWAMKFSLHMT-UHFFFAOYSA-N 0.000 claims 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical class BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 claims 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical class NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims 1
- GHKHTBMTSUEBJD-UHFFFAOYSA-N 5,6-dichloro-1,3-benzothiazol-2-amine Chemical class ClC1=C(Cl)C=C2SC(N)=NC2=C1 GHKHTBMTSUEBJD-UHFFFAOYSA-N 0.000 claims 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 claims 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 claims 1
- IILAFGOJFGBAGC-UHFFFAOYSA-N n-bromo-2,4-dinitroaniline Chemical class [O-][N+](=O)C1=CC=C(NBr)C([N+]([O-])=O)=C1 IILAFGOJFGBAGC-UHFFFAOYSA-N 0.000 claims 1
- UTDPIIKQXMQXNC-UHFFFAOYSA-N n-chloro-2,4-dinitroaniline Chemical class [O-][N+](=O)C1=CC=C(NCl)C([N+]([O-])=O)=C1 UTDPIIKQXMQXNC-UHFFFAOYSA-N 0.000 claims 1
- KPFGGEHCIZEMTD-UHFFFAOYSA-N n-chloro-4-nitroaniline Chemical class [O-][N+](=O)C1=CC=C(NCl)C=C1 KPFGGEHCIZEMTD-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 abstract description 48
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 23
- 150000003613 toluenes Chemical class 0.000 abstract description 15
- 150000001555 benzenes Chemical class 0.000 abstract description 12
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 239000004744 fabric Substances 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000004043 dyeing Methods 0.000 abstract description 5
- 230000007423 decrease Effects 0.000 abstract description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000004753 textile Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 1
- QEORVDCGZONWCJ-UHFFFAOYSA-N 2-[[4-[2-cyanoethyl(ethyl)amino]phenyl]diazenyl]-5-nitrobenzonitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N QEORVDCGZONWCJ-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- KHZRTXVUEZJYNE-UHFFFAOYSA-N 3-[4-[(2,6-dichloro-4-nitrophenyl)diazenyl]-n-ethylanilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl KHZRTXVUEZJYNE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
The invention provides the ecological, environmental protective processing method of a kind of dyestuff or dyestuff intermediate, methods described includes：Added water and alkaline agent in toward dyestuff or dyestuff intermediate, reaction system normal pressure, 50~90 DEG C or under the conditions of 0.1~0.5MPa, 100~150 DEG C, stirring reaction 3~5 hours, reaction terminates dyestuff or intermediate after rear suction filtration washing is handled；Wherein the ratio between dyestuff or dyestuff intermediate, the mole dosage of alkaline agent are 1:0.2~6.Dyestuff or dyestuff intermediate are after ecological, environmental protective of the present invention processing, tetrachlorophenol（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and toluenes）Decline to a great extent, tetrachlorophenol on fabric after the dyeing of this dyestuff or the synthesis of this dyestuff intermediate（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and toluenes）Meet the limitation requirement in Oeko Tex Standard100.
Description
（One）Technical field
The present invention relates to the ecological, environmental protective processing method of a kind of dyestuff or dyestuff intermediate.
（Two）Background technology
As long as the past is not it is considered that dyestuff contains disabling azo, without carcinogenic/sensitization dye, without point directly disabled
Huang 23, disperse orange 149, disperse orange 76 etc. are dissipated, can meet these requirements can be referred to as environment-friendly dye, and these disabling projects are one
Compare basic environmental requirement a bit.But recently as safety and environmental requirement more and more higher of the public to textile, especially
It is Oeko-Tex Standard100, also has tetrachlorophenol in addition to above-mentioned project（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene
With containing chlorotoluene（Chlorinated benzenes and toluenes）Limitation requirement.Benzene Chloride and chlorinated toluenes and four
Chlorophenol and pentachlorophenol are not easily decomposed, during the textile that dress is remained containing it, can be entered human body by skin and be produced biology
Savings, the health to human body causes potential threat；And have serious harm to environment, water body, soil and air can be caused
Pollution is a kind of with persistence and highly toxic compound.Tetrachlorophenol（PCP）, pentachlorophenol（TeCP）On the textile
Regulation limitation only 0.05~0.5ppm；Containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and toluenes）
Regulation limitation on the textile is 1.0ppm.
The tetrachlorophenol of current most of dyestuffs or dyestuff intermediate（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene and chloride
Toluene（Chlorinated benzenes and toluenes）Tetrachlorophenol on fabric after severe overweight, dyeing
（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and toluenes）Content
Oeko-Tex Standard100 limitation requirement is not met.
（Three）The content of the invention
To solve the above problems, the present invention provides the ecological, environmental protective processing method of a kind of dyestuff or dyestuff intermediate, dyestuff
Or dyestuff intermediate is after processing, the tetrachlorophenol after the dyeing of this dyestuff or the synthesis of this dyestuff intermediate on fabric
（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and toluenes）Content
Meet the limitation requirement in Oeko-Tex Standard100.
The technical solution adopted by the present invention is：
A kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate, methods described includes：Toward in the middle of dyestuff or dyestuff
Add suitable quantity of water and alkaline agent in body, the reaction system is stirred under the conditions of normal pressure, 50~90 DEG C or 0.1~0.5MPa, 100~150 DEG C
Mix reaction 3~5 hours, reaction terminates dyestuff or intermediate after rear suction filtration washing is handled；Wherein in the middle of dyestuff or dyestuff
The ratio between body, mole dosage of alkali are 1:0.2~6, preferably 1:3~6.The above-mentioned water mole individually added is dyestuff or dyestuff
15~60 times of intermediate mole, alkaline agent can be added directly, can also mass concentration 20~40% the aqueous solution form addition.
The dyestuff is the conventional azo dyes in this area, and such as C.I. Red-1 200s 53, C.I. Red-1 200s 52, C.I. disperse
Red 73, C.I. disperse blues 291：1st, the dyestuff such as C.I. disperse blues 291, C.I. disperse violets 93；The dyestuff intermediate is this area
Conventional aromatic amine dyestuff intermediate, including aniline, the aryl primary amine or heterocyclic amine of substitution, such as by halogen（Such as chlorine, bromine）, nitro,
The aniline of cyano group substitution, particularly 2,6- dichloros（Or bromine）- 4- nitroanilines, 6- chlorine（Or bromine）- 2,4- dinitroanilines, 3,4-
Dichloro（Or bromine）Aniline, 2- chlorine（Or bromine）- 4- nitroanilines, 2- amino -5,6（6,7）- dichlorobenzothiazole, adjacent cyanogen are to nitro
Aniline, 2,4- dinitroanilines or paranitroanilinum etc..
Described dyestuff or dyestuff intermediate can be obtained by synthetic method well known to those skilled in the art, can also adopt
Use commercially available prod.
The alkaline agent be conventional inorganic bases or organic base, inorganic base for example sodium carbonate, sodium acid carbonate, potassium carbonate, saleratus,
Ammoniacal liquor, sodium hydroxide, ammonium hydroxide, potassium hydroxide, lithium hydroxide, aluminium hydroxide etc.；Organic base such as methylamine, ethamine, triethylamine
Deng.
It may further be enriched with machine solvent in the reaction system, the middle dyestuff or dyestuff intermediate, alkali, organic solvent rub
The ratio between your consumption is 1:0.2~6:1~6, preferably 1:1~3:4~6.The organic solvent is one of following or two of which
Mixture above：N,N-dimethylformamide, methanol, ethanol, ethylene glycol, polyethylene glycol, isopropanol, acetone, espeleton,
Methylisobutylketone, acetonitrile, styrene, triethanolamine, chloroethanes, dichloroethanes, trichloroethanes, tetrachloroethanes, benzene, toluene, two
Toluene, pentane, hexane, octane, hexamethylene, cyclohexanone, toluene cyclohexanone.The organic solvent of addition, reaction can normal pressure after terminating
Its organic solvent is reclaimed in distillation or vacuum distillation, and recyclable is applied mechanically.
It is preferred that, the reaction is carried out under the conditions of normal pressure, 50~80 DEG C.
The beneficial effects are mainly as follows：Dyestuff or dyestuff intermediate are by ecological, environmental protective of the present invention
After reason, tetrachlorophenol（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and
toluenes）Decline to a great extent, tetrachlorophenol on fabric after the dyeing of this dyestuff or the synthesis of this dyestuff intermediate（PCP）, five
Chlorophenol（TeCP）, containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and toluenes）Meet Oeko-Tex
Limitation requirement in Standard100.
（Four）Embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This：
Embodiment 1：
Water 135g is added in 500ml three-necked flask, 2,6- Dichloro-4-nitroanilines are added（Paranitroanilinum is passed through
Superchlorination reaction synthesis is obtained）40g（Percentage amount, 0.19mol）With 30% sodium hydroxide solution 25g（0.19mol）, normal pressure heating
To 60 DEG C, and stirring reaction 3 hours at this temperature, it is obtained that reaction terminates rear suction filtration washing.
Embodiment 2：
Water 85g is added in 500ml three-necked flask, 2,6- Dichloro-4-nitroanilines are added（Commercially available prod）50g
（Percentage amount, 0.24mol）, 20% ammoniacal liquor 75g（0.43mol）With dichloroethanes 100g（1mol）, normal pressure is warming up to 75 DEG C, and
Stirring reaction 4 hours at a temperature of this, mixing time reclaims organic solvent dichloroethanes after arriving in 60~95 DEG C of air-distillations, reclaims
Dichloroethanes can continue next time to apply mechanically, then by reaction solution suction filtration wash be made.
Embodiment 3~17：
By the method described in above-described embodiment, by dyestuff or dyestuff intermediate, water, alkaline agent and organic solvent according to the form below 1
Ratio（The consumption of table reclaimed water is the water individually added）It is small further according to respective reaction condition stirring reaction 3~5 after mixing
When, if addition organic solvent, then organic solvent is reclaimed in 60~95 DEG C of vacuum distillations after reaction terminates, finally will reaction
The washing of liquid suction filtration is made.
Table 1
Detect embodiment 9：
Respectively by without PROCESS FOR TREATMENT of the present invention and above-described embodiment obtain dyestuff or dyestuff intermediate synthesis
Dyestuff, by ISO17070：2006、US EPA8081B：Method described in 2007 or the like is determined after dyeing four on fabric
Chlorophenol（PCP）, pentachlorophenol（TeCP）, containing chlorobenzene and containing chlorotoluene（Chlorinated benzenes and
toluenes）Content, as a result see the table below 2：
Table 2
From upper table 2, after dyestuff or dyestuff intermediate are handled through ecological, environmental protective of the present invention, whether dyestuff or
The dyestuff of dyestuff intermediate synthesis, it is dyed after tetrachlorophenol on fabric（PCP）, pentachlorophenol（TeCP）, Benzene Chloride and
Chlorinated toluenes（Chlorinated benzenes and toluenes）Content meets tetrachloro in Oeko-Tex Standard100
Phenol（PCP）0.05ppm, pentachlorophenol（TeCP）0.05~0.5ppm, Benzene Chloride and chlorinated toluenes（Chlorinated
benzenes and toluenes）1.0ppm limitation requirement.
Claims (3)
1. a kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate, methods described includes：Toward dyestuff or dyestuff intermediate
In add water and alkaline agent and organic solvent, the dyestuff be azo dyes, the dyestuff intermediate be aromatic amine dyestuff intermediate, instead
System is answered under the conditions of normal pressure, 50~90 DEG C or 0.1~0.5MPa, 100~150 DEG C, stirring reaction 3~5 hours, reaction terminates
Dyestuff or intermediate after suction filtration washing is handled afterwards；The dyestuff or dyestuff intermediate, alkaline agent, organic solvent mole with
The ratio between amount is 1:0.2~6:1~6；The organic solvent is mixture more than one of following or two of which：N, N- dimethyl
Formamide, methanol, ethanol, ethylene glycol, polyethylene glycol, isopropanol, acetone, espeleton, methylisobutylketone, acetonitrile, styrene,
Triethanolamine, chloroethanes, dichloroethanes, trichloroethanes, tetrachloroethanes, benzene,toluene,xylene, pentane, hexane, octane, hexamethylene
Alkane, cyclohexanone, toluene cyclohexanone；
The azo dyes is C.I. Red-1 200s 53, C.I. Red-1 200s 52, C.I. disperse red 73s, C.I. disperse blues 291：1、
C.I. disperse blue 291 or C.I. disperse violets 93；The aromatic amine dyestuff intermediate is 2,6- Dichloro-4-nitroanilines, 2,6- bis-
The chloro- 2,4- dinitroanilines of bromo- 4- nitroanilines, 6-, the bromo- 2,4- dinitroanilines of 6-, 3,4- dichloroanilines, 3,4- dibromobenzenes
The chloro- 4- nitroanilines of amine, 2-, the bromo- 4- nitroanilines of 2-, 2- amino -5,6- dichlorobenzothiazoles, 2- amino -6,7- dichloro-benzenes
And thiazole, adjacent cyanogen paranitroanilinum, 2,4- dinitroanilines or paranitroanilinum.
2. the method as described in claim 1, it is characterised in that the alkaline agent is one of following：Sodium carbonate, sodium acid carbonate, carbonic acid
Potassium, saleratus, ammoniacal liquor, sodium hydroxide, ammonium hydroxide, potassium hydroxide, lithium hydroxide, aluminium hydroxide, methylamine, ethamine, three second
Amine.
3. method as claimed in claim 1 or 2, it is characterised in that the reaction is carried out under the conditions of normal pressure, 50~80 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310718981.9A CN104725897B (en) | 2013-12-23 | 2013-12-23 | A kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310718981.9A CN104725897B (en) | 2013-12-23 | 2013-12-23 | A kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104725897A CN104725897A (en) | 2015-06-24 |
| CN104725897B true CN104725897B (en) | 2017-08-25 |
Family
ID=53450344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310718981.9A Active CN104725897B (en) | 2013-12-23 | 2013-12-23 | A kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104725897B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106800798B (en) * | 2016-12-30 | 2019-12-06 | 浙江闰土研究院有限公司 | Disperse dye composition and preparation method and application thereof |
| CN106752080B (en) * | 2016-12-30 | 2020-09-01 | 浙江闰土研究院有限公司 | Disperse dye composition and preparation method and application thereof |
| CN106748810B (en) * | 2016-12-30 | 2021-04-27 | 浙江闰土研究院有限公司 | Treatment method of disperse dye intermediate |
| CN106590027B (en) * | 2016-12-30 | 2020-05-01 | 浙江闰土研究院有限公司 | Disperse dye composition and preparation method and application thereof |
| CN108191672B (en) * | 2017-12-19 | 2021-06-11 | 浙江龙盛集团股份有限公司 | Synthetic method of 2, 4-dinitro-6-chloroaniline |
| CN112011194A (en) * | 2019-05-30 | 2020-12-01 | 浙江闰土研究院有限公司 | Disperse dye composition, preparation method thereof and treatment method of dye intermediate of disperse dye composition |
| CN113527909A (en) * | 2021-07-23 | 2021-10-22 | 杭州吉华江东化工有限公司 | Synthesis process of environment-friendly dye |
| CN114316629A (en) * | 2021-12-23 | 2022-04-12 | 江苏格罗瑞化学有限公司 | Green and environment-friendly disperse dye intermediate treatment method |
| CN115651422B (en) * | 2022-10-25 | 2024-02-09 | 杭州吉华江东化工有限公司 | Synthesis method of environment-friendly heterocyclic disperse red dye |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0948924A (en) * | 1995-08-07 | 1997-02-18 | Minolta Co Ltd | Production of trisazo pigment |
| CN1251377A (en) * | 1998-10-15 | 2000-04-26 | 拜尔公司 | Metal matches pigment |
| CN1688658A (en) * | 2002-10-25 | 2005-10-26 | 科莱恩有限公司 | Method and device for carrying out chemical and physical methods |
| CN1771297A (en) * | 2003-04-10 | 2006-05-10 | 科莱恩有限公司 | Methanesulfomide azo dye |
| CN1957043A (en) * | 2004-05-19 | 2007-05-02 | 巴斯福股份公司 | Method for producing a liquid formulation of salts of sulphonic-acid azo dyes |
| CN101627090A (en) * | 2007-06-22 | 2010-01-13 | 科莱恩金融(Bvi)有限公司 | The preparation method of pure C.I. pigment orange 74 |
| CN103275518A (en) * | 2013-05-30 | 2013-09-04 | 鞍山七彩化学股份有限公司 | Method for preparing high-transparency high-strength pigment yellow 155 for water-based ink and water-based paint |
-
2013
- 2013-12-23 CN CN201310718981.9A patent/CN104725897B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0948924A (en) * | 1995-08-07 | 1997-02-18 | Minolta Co Ltd | Production of trisazo pigment |
| CN1251377A (en) * | 1998-10-15 | 2000-04-26 | 拜尔公司 | Metal matches pigment |
| CN1688658A (en) * | 2002-10-25 | 2005-10-26 | 科莱恩有限公司 | Method and device for carrying out chemical and physical methods |
| CN1771297A (en) * | 2003-04-10 | 2006-05-10 | 科莱恩有限公司 | Methanesulfomide azo dye |
| CN1957043A (en) * | 2004-05-19 | 2007-05-02 | 巴斯福股份公司 | Method for producing a liquid formulation of salts of sulphonic-acid azo dyes |
| CN101627090A (en) * | 2007-06-22 | 2010-01-13 | 科莱恩金融(Bvi)有限公司 | The preparation method of pure C.I. pigment orange 74 |
| CN103275518A (en) * | 2013-05-30 | 2013-09-04 | 鞍山七彩化学股份有限公司 | Method for preparing high-transparency high-strength pigment yellow 155 for water-based ink and water-based paint |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104725897A (en) | 2015-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104725897B (en) | A kind of ecological, environmental protective processing method of dyestuff or dyestuff intermediate | |
| BR112018011030A2 (en) | ? compound, mixture, composition, vulcanizable elastomeric formulation, vulcanized elastomeric article, and vehicle tire? | |
| CN105541674B (en) | A kind of compound and preparation method thereof and the application in terms of dyestuff | |
| CN106752079A (en) | A kind of disperse dye composition and its production and use | |
| CN105254575B (en) | A kind of synthetic method of sulphadiazine | |
| CN102219704A (en) | Improved method for synthesizing 1,4-diamino-2,3-dichloroanthraquinone | |
| CN106833023B (en) | Disperse dye composition and preparation method and application thereof | |
| CN106748810A (en) | A kind of processing method of disperse dyes intermediate | |
| CN102807765B (en) | 5-chloronitroaniline-containing dye | |
| CN106752081A (en) | A kind of disperse dye composition and its production and use | |
| CN106496199A (en) | His Wei of Dacca and its preparation method of intermediate | |
| CN103059367B (en) | Production method of brominated butadiene styrene rubber | |
| CN106187814B (en) | A kind of synthetic method of disperse dyes diazol | |
| GB1589454A (en) | Cationic dyes the production thereof and their use | |
| TW200704723A (en) | 1-phenoxy-2-propanol as a formulating aid for dyes | |
| CN102433030A (en) | Active yellow dye composition | |
| CN110028429A (en) | A kind of preparation method of paratoluensulfonyl chloride | |
| CN106349105B (en) | A kind of preparation method of benzyl cyanide | |
| CN105481624B (en) | The catalysis oxidation synthetic method of Arneel SD | |
| CN106966922A (en) | A kind of synthetic method of the dicyanoethylene class compound of functionalization substitution | |
| CN102786492A (en) | Preparation method of 3-isothiazolinone compound | |
| CN107892824B (en) | A kind of preparation method of environment-friendly type azo dispersion dyes | |
| CN105295425B (en) | Environment-friendly weak acid red dye and preparation method thereof | |
| CN103992265B (en) | Two three bromo 1,3-bis-pyridine alkali propane and preparation method thereof, using method, recovery method and application | |
| CN105295423A (en) | Weak acid violet-red dye and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |