CN115073935A - Synthesis method of C.I. pigment orange 61 - Google Patents
Synthesis method of C.I. pigment orange 61 Download PDFInfo
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- CN115073935A CN115073935A CN202210818369.8A CN202210818369A CN115073935A CN 115073935 A CN115073935 A CN 115073935A CN 202210818369 A CN202210818369 A CN 202210818369A CN 115073935 A CN115073935 A CN 115073935A
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- acid
- methylazobenzene
- solvent
- pigment orange
- reaction
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- 239000000049 pigment Substances 0.000 title claims abstract description 52
- 238000001308 synthesis method Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 37
- -1 4-amino-4 ' -nitro-3-methylazobenzene Chemical compound 0.000 claims abstract description 33
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 30
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 30
- XYQXGZLLGNQFSL-UHFFFAOYSA-N methyl 2,3,4,5-tetrachloro-6-cyanobenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C#N XYQXGZLLGNQFSL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 238000005859 coupling reaction Methods 0.000 claims abstract description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 16
- PQOCJJXGVAFTQU-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C=CC(N)=CC=2)=C1 PQOCJJXGVAFTQU-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 13
- 230000008878 coupling Effects 0.000 claims abstract description 9
- 238000010168 coupling process Methods 0.000 claims abstract description 9
- 239000012043 crude product Substances 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011734 sodium Substances 0.000 claims abstract description 7
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 7
- 238000004381 surface treatment Methods 0.000 claims abstract description 7
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012954 diazonium Substances 0.000 claims abstract description 6
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 6
- 230000019612 pigmentation Effects 0.000 claims abstract description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 4
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 32
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 24
- 238000001914 filtration Methods 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 239000012065 filter cake Substances 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 235000010288 sodium nitrite Nutrition 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 230000002194 synthesizing effect Effects 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000003801 milling Methods 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 238000006462 rearrangement reaction Methods 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004576 sand Substances 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- 239000003021 water soluble solvent Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 3
- ULVDMKRXBIKOMK-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2,3-dihydroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C2CNC(=O)C2=C1Cl ULVDMKRXBIKOMK-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 238000000498 ball milling Methods 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005077 polysulfide Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Polymers [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 claims description 2
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 claims description 2
- 230000008961 swelling Effects 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000975 dye Substances 0.000 abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZWWOYERTGZZDMF-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3,3-dimethoxy-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(OC)(OC)NC2=O ZWWOYERTGZZDMF-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 4
- 238000004537 pulping Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 3
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 3
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MMVDLMPGBRLTSO-UHFFFAOYSA-N 1-(diazonioamino)-4-nitrobenzene Chemical class [O-][N+](=O)C1=CC=C(N[N+]#N)C=C1 MMVDLMPGBRLTSO-UHFFFAOYSA-N 0.000 description 1
- IGSKVMQALPYWSB-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-cyanobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C#N IGSKVMQALPYWSB-UHFFFAOYSA-N 0.000 description 1
- CUVAUYUUVFGQAI-UHFFFAOYSA-N 3,3,4,5,6,7-hexachloro-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(Cl)(Cl)C2=C1Cl CUVAUYUUVFGQAI-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- ALHBMUPPYBACCH-UHFFFAOYSA-N azanium;2,3,4,5-tetrachloro-6-cyanobenzoate Chemical compound [NH4+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C#N ALHBMUPPYBACCH-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QNCMDFVHPFYZNK-UHFFFAOYSA-N butan-1-ol;2-methylpropan-1-ol Chemical compound CCCCO.CC(C)CO QNCMDFVHPFYZNK-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C09B56/00—Azo dyes containing other chromophoric systems
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of C.I. pigment orange 61, which belongs to the technical field of organic dyes, wherein tetrachlorophthalic anhydride is subjected to chlorination reaction, and then the chlorination solution is reacted with a methanol solution of ammonia water to obtain 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester; carrying out diazotization reaction on paranitroaniline in dilute hydrochloric acid, coupling and rearranging the obtained diazonium salt with m-aminotoluene to obtain 4-amino-4 ' -nitro-3-methylazobenzene, and reducing the nitro of the 4-amino-4 ' -nitro-3-methylazobenzene to obtain 4,4 ' -diamino-3-methylazobenzene; then, reacting 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester with sodium alkoxide to obtain 3, 3-dimethyl-oxyalkyl-4, 5,6, 7-tetrachloroisoindolinone, then directly adding 4, 4' -diamino-3-methyl azobenzene into a reaction system for condensation reaction to obtain a C.I. pigment orange 61 crude product, and finally performing pigmentation and surface treatment to obtain a C.I. pigment orange 61 product; the invention solves the problem of complicated synthesis steps of the C.I. pigment orange 61, and ensures that the synthesis process and the operation environment are simpler, safer and more environment-friendly.
Description
Technical Field
The invention relates to the technical field of organic dyes, in particular to a method for synthesizing C.I. pigment orange 61.
Background
The isoindolinone pigments are high-grade colorants, the light and weather fastness of the isoindolinone pigments is 7-8 (the highest 8), and the heat stability of the isoindolinone pigments is above 300 ℃ (detailed data thereof is found in the world dye variety universe). Such pigments currently marketed are mainly based on c.i. pigment yellow 109, c.i. pigment yellow 110 and c.i. pigment orange 61. The C.I. pigment orange 61 is yellow orange powder, is suitable for coloring PVC (soft plastic, hard plastic), PP, PE, PS/ABS, synthetic fiber raw stock and the like, and is also suitable for industrial coatings (such as automobile paint, exterior wall coating and the like).
The method adopted for synthesizing the C.I. pigment orange 61 at present comprises the following steps: boiling 3,3,4,5,6, 7-hexachloroisoindolinone and intermediate 4, 4' -diamino-3-methylazobenzene in a high boiling point solvent to remove HCl to prepare a crude pigment product, and grinding the crude pigment product to obtain a finished product. The method adopted by the invention is that 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester is converted into 3, 3-dialkoxy-4, 5,6, 7-tetrachloroisoindolinone, and then the 3, 3-tetrachloroisoindolinone is condensed with 4, 4' -diamino-3-methylazobenzene, so that the problems that a high-boiling point solvent is difficult to recover and the high temperature of an operation environment is avoided can be solved.
The methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate is used as an important intermediate of isoindolinone pigments, and the current main production scheme is as follows: the catalyst is prepared by taking 2,3,4, 5-tetrachloro-6-cyanobenzoic acid ammonium salt as a raw material and taking dimethyl sulfate as a methylating agent in different catalysts and solvents. The process has long synthesis route, uses highly toxic dimethyl sulfate, and generates a large amount of waste sulfate which is difficult to treat. The invention designs and implements a brand new synthetic route to solve the production problem, so that the synthesis of the intermediate becomes simpler, more environment-friendly and safer.
Another intermediate for 4, 4' -diamino-3-methylazobenzene to c.i. pigment orange 61 is currently synthesized by: the amino of the paranitroaniline is protected, and then the product is obtained through the procedures of reduction, diazotization, coupling, rearrangement, hydrolysis and alkali regulation in sequence.
Disclosure of Invention
The present invention aims to provide a method for synthesizing c.i. pigment orange 61, so as to solve the problems proposed in the background art.
In order to achieve the purpose, the invention provides the following technical scheme:
a method for synthesizing c.i. pigment orange 61, comprising the steps of:
s1, synthesis of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate: performing chlorination reaction on tetrachlorophthalic anhydride to obtain light green chlorination liquid; then slowly dripping the chlorination solution into a methanol solution of ammonia water for reaction to obtain a crude product, dissolving the crude product in a first solvent, filtering out insoluble substances while the crude product is hot, and recrystallizing mother liquor to obtain 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester;
synthesis of S2, 4-amino-4' -nitro-3-methylazobenzene: adding nitroaniline into hydrochloric acid, stirring until the material is grey white slurry, then adding an ice water mixture into the mixture, cooling the mixture to below 5 ℃, then dropwise adding a sodium nitrite aqueous solution to perform diazotization reaction to obtain a diazonium salt aqueous solution, using sulfamic acid to destroy excessive sodium nitrite in the system, dissolving m-aminotoluene in a second solvent in advance, controlling the temperature, dropwise adding the diazonium salt to perform coupling reaction, finally using a deacidification agent to adjust the pH value so that the coupling reaction continues to the end point, filtering to obtain a coupling material filter cake, dissolving the coupling filter cake in a third solvent, using acid to adjust the pH value, heating up the solution to perform rearrangement reaction to obtain 4-amino-4' -nitro-3-methylazobenzene;
synthesis of S3, 4' -diamino-3-methylazobenzene: mixing the 4-amino-4 '-nitro-3-methylazobenzene with a solvent, adding a catalyst, and reducing the 4, 4' -diamino-3-methylazobenzene by using a reducing agent;
synthesis of S4, 3-dialkoxy-4, 5,6, 7-tetrachloroisoindolinone: dispersing 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester into a solvent IV, then adding sodium alkoxide, controlling the reaction temperature, and reacting until the materials are completely dissolved;
s5, c.i. crude synthesis of pigment orange 61: dissolving or dispersing 4, 4' -diamino-3-methylazobenzene in a solvent, adding the solution into a 3, 3-dialkoxy 4,5,6, 7-tetrachloroisoindolinone solution, controlling the reaction temperature to ensure that the solution reacts completely, adjusting the pH value to be acidic by using acid, precipitating the material, filtering, washing and drying to obtain a crude pigment product;
s6, pigmentation and surface treatment: and performing pigment treatment on the crude pigment to obtain C.I. pigment orange 61 with different formulations, performing surface treatment on the crude pigment with an auxiliary agent, and filtering, drying and crushing to obtain a finished product of the C.I. pigment orange 61.
As a further scheme of the invention: in step S1, substances involved in the chlorination of tetrachlorophthalic anhydride include, but are not limited to, phosphorus pentachloride, phosphorus trichloride, gaseous and liquid chlorine, wherein phosphorus trichloride is used as a solvent, and gaseous chlorine is preferred.
As a further scheme of the invention: in the step S1, the concentration of the methanol solution of ammonia gas is 0.5% to 15%, preferably 3% to 8%.
As a further scheme of the invention: in step S1, the solvent used for refining the crude methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate includes, but is not limited to, one of aliphatic alcohols such as methanol, ethanol, propanol, isobutanol, butanol and isobutanol, preferably methanol and isobutanol.
As a further scheme of the invention: in step S2, the second solvent for dissolving m-aminotoluene includes, but is not limited to, water-soluble solvents such as acid water mixture, DMF and DMSO, and aliphatic alcohols such as methanol, ethanol, propanol, isobutanol and butanol isobutanol, and organic solvents with good water solubility such as methanol, ethanol, DMF and DMSO are preferred.
As a further scheme of the invention: in step S2, the acid-removing agent used in the coupling reaction includes, but is not limited to, one of organic acid salts such as acetate and oxalate, and inorganic acid salts such as carbonic acid and phosphoric acid, and acetate is preferred.
As a further scheme of the invention: in the step S2, the pH value of the coupling reaction is 1-10, and the preferable pH value is 3-4.
As a further scheme of the invention: in step S2, the third solvent for the rearrangement reaction includes, but is not limited to, water-soluble solvents such as DMF and DMSO, and one of aliphatic alcohols such as methanol, ethanol, propanol, isobutanol and butanolisobutanol, and preferably water-soluble aliphatic alcohols such as methanol and ethanol.
As a further scheme of the invention: in the step S2, the pH value of the rearrangement reaction is 1-10, preferably less than or equal to 2.
As a further scheme of the invention: in the step S3, the catalyst includes, but is not limited to, Fe 2+ 、Fe(OH) 3 C, Raney nickel, palladium carbon with different contents and platinum carbon.
As a further scheme of the invention: in the S3 step, the reducing agent includes, but is not limited to, one of iron powder, zinc powder, sodium sulfide, hydrosulfide, polysulfide, and hydrogen gas, preferably hydrogen gas, sodium hydrosulfide, and sodium disulfide.
As a further scheme of the invention: in step S4, the sodium alkoxide includes, but is not limited to, one of fatty sodium alkoxides such as sodium methoxide, sodium ethoxide, and sodium propoxide, and sodium methoxide is preferred.
As a further scheme of the invention: in the step S6, the pigmenting treatment method includes, but is not limited to, one of conventional and unconventional treatment methods such as an acid swelling method, an acid dissolution precipitation method, a solvent treatment method, a sand milling method, a salt milling method, and a ball milling method, and preferably a method of high-temperature treatment in a DMF phase.
As a further scheme of the invention: in the S6 step, the auxiliary agent includes, but is not limited to, one of an anionic surfactant, a cationic surfactant and a nonionic surfactant, preferably a nonionic surfactant such as rosin amine and AE-6.
The synthetic route of the c.i. pigment orange 61 is as follows:
compared with the prior art, the invention has the beneficial effects that: the invention opens the synthesis process of redesigning and optimizing 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester and 4, 4' -diamino-3-methylazobenzene, solves the problem of complicated synthesis steps of C.I. pigment orange 61, and ensures that the synthesis process and the operation environment are simpler, safer and more environment-friendly.
Detailed Description
Example 1
Synthesis of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate: adding 300 parts of tetrachlorophthalic anhydride and 275 parts of phosphorus pentachloride into a reaction kettle, slowly heating to 130 ℃ for chlorination reaction, keeping the temperature for 4 hours after the materials are slowly changed from solid to light green solution, and recovering a byproduct POCl by reduced pressure distillation 3 Then, the prepared chlorination liquid is kept at the temperature of more than 80 ℃ for standby.
And (3) cooling 1200 parts of 5% ammonia methanol solution to below-5 ℃, slowly dropwise adding the chlorination solution into the solution, controlling the temperature below-5 ℃ all the time, and continuing to perform heat preservation reaction for 4 hours after the chlorination solution is completely added.
Adding a catalyst TS into a reaction system, heating and refluxing until the materials are basically completely dissolved, cooling to below 0 ℃, filtering to obtain a filter cake, rectifying the mother liquor to recover methanol, adding the filter cake into 3000 parts of methanol solution, heating to 55 ℃, stirring for 2 hours, filtering while hot, collecting hot filtered mother liquor, cooling to below 0 ℃, filtering, and drying the filter cake to obtain the catalyst.
And then slowly dropwise adding the chlorination solution into a methanol solution of ammonia water for reaction to obtain a crude product, dissolving the crude product in a hot alcohol solution, filtering out insoluble substances while the solution is hot, and recrystallizing the mother solution to obtain 285 parts of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate with the content of 99.23%.
Synthesis of 4-amino-4' -nitro-3-methylazobenzene: 310 parts of 32% hydrochloric acid is added to 500 parts of water, 150 parts of flaky p-nitroaniline is slowly added thereto with stirring, and stirring is continued until the material is an off-white slurry. Then adding an ice-water mixture into the mixture, cooling the mixture to below-5 ℃, and then slowly dropwise adding a sodium nitrite aqueous solution prepared in advance (80 parts of sodium nitrite is added into 300 parts of water and stirred until the sodium nitrite aqueous solution is completely dissolved) into the reaction system, wherein the temperature is kept below 5 ℃ all the time. After the sodium nitrite is added, the positive is detected by KI-starch test paper and kept for 0.5 hour. Excess sodium nitrite in the system was destroyed with 15% aqueous sulfamic acid (microscopic blue to colorless as detected by KI-starch paper).
In a further reactor 117 parts of m-aminotoluene and 500 parts of methanol are added and stirred until dissolved, and the solution is then slowly added dropwise to an aqueous solution of the diazonium salt, while the temperature is maintained below 5 ℃. After the addition was completed, the pH was slowly adjusted to 3 with sodium acetate, and the coupling reaction was continued to the end point (the reaction system was checked by ring-permeation with 0.5% aqueous H acid until the detection was negative). Filtering, and washing a filter cake to be neutral by water.
The whole of the coupling cake was added to 4500 parts of methanol, stirred for 0.5 hours, then added with 90 parts of 32% hydrochloric acid, and then heated under reflux for 3 hours. Cooling and filtering to obtain a filter cake, pulping the filter cake by using a sodium carbonate aqueous solution, and filtering to obtain 240 parts (dry weight) of 4-amino-4' -nitro-3-methylazobenzene with the liquid chromatography content of 98.82%.
Synthesis of 4, 4' -diamino-3-methylazobenzene: 200 parts (dry weight) of 4-amino-4 '-nitro-3-methyl azobenzene is added into 2600 parts of methanol, 5 parts of 2% palladium carbon is added as a catalyst, air in a kettle is replaced by nitrogen for three times, then the temperature is slowly increased to 80 ℃, hydrogen is slowly introduced into a reaction system until the pressure is 2PMa, after no hydrogen absorption phenomenon exists in a hydrogenation reaction kettle, the temperature is decreased to 60 ℃, the catalyst is filtered out when the temperature is hot, mother liquor is decreased, filter cakes are filtered, and the filter cakes are sealed and stored to obtain 152 parts (dry weight) of 4, 4' -diamino-3-methyl azobenzene.
Synthesis of 3, 3-dimethoxy-4, 5,6, 7-tetrachloroisoindolinone: 275 parts of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate are added to 2000 parts of methanol, stirred for 0.5 hour, 170 parts of 30% sodium methoxide methanol solution are then added, the mixture is slowly warmed to 40 ℃ and reacted at this temperature until the material is completely dissolved.
C.i. crude synthesis of pigment orange 61: 104 parts (by dry weight) of a cake of 4, 4' -diamino-3-methylazobenzene are added. Adding the mixture into 500 parts of methanol, pulping uniformly, slowly adding the mixture into the methanol solution of the 3, 3-dimethoxy-4, 5,6, 7-tetrachloroisoindolinone, after adding, slowly heating to reflux for 7 hours, adjusting the pH to 3 by using glacial acetic acid, filtering, washing and drying to obtain 365 parts of crude pigment.
Pigmentation and surface treatment: 200 parts of the crude pigment product is added into 1600 parts of DMF, added into a sand mill for circular sand milling for 8 hours, heated to 90 ℃ for treatment for 4 hours, filtered and washed with water. Putting the filter cake into 2000 parts of water, adding 8 parts of rosin amine, heating to 85 ℃, preserving heat for 1 hour, filtering, drying and crushing to obtain 205 parts of finished C.I. pigment orange 61.
Example 2
Synthesis of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate: adding 300 parts of tetrachlorophthalic anhydride and 180 parts of phosphorus pentachloride into a reaction kettle, slowly heating to 70 ℃ under stirring, introducing 95 parts of chlorine into the reaction kettle for chlorination reaction for about 6 hours, slowly heating to 130 ℃,after the materials slowly change from solid to light green solution, reduced pressure distillation is carried out to recover by-product POCl 3 The prepared chlorination liquid is kept at the temperature of more than 80 ℃ for standby.
The other steps in this example are the same as in example 1. 287 parts of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate are obtained, having a liquid chromatography content of 98.76%.
Example 3
The procedure was as in example 1 except that the coupling and rearrangement were carried out in a different manner from that in example 1.
Synthesis of 4-amino-4' -nitro-3-methylazobenzene: 310 parts of 32% hydrochloric acid is added to 500 parts of water, 150 parts of p-nitroaniline in flakes are slowly added thereto with stirring, and stirring is continued until the material is an off-white slurry. Then adding an ice-water mixture into the mixture, cooling the mixture to below-5 ℃, and then slowly dropwise adding a sodium nitrite aqueous solution prepared in advance (80 parts of sodium nitrite is added into 300 parts of water and stirred until the sodium nitrite aqueous solution is completely dissolved) into the reaction system, wherein the temperature is kept below 5 ℃ all the time. After the sodium nitrite is added, KI-starch test paper is used for detecting positive, and the positive is kept for 0.5 hour. The excess sodium nitrite in the system was destroyed with 15% sulfamic acid aqueous solution and detected with KI-starch paper as a bluish to colorless test.
Adding 117 parts of m-aminotoluene, 1300 parts of water and 126 parts of 32% hydrochloric acid into another reactor, stirring until the m-aminotoluene and the water are dissolved, slowly dropwise adding the p-nitroaniline diazonium salt prepared in advance into the reactor, keeping the temperature below 10 ℃ during the process, and continuously adjusting the pH value to 3-5 by using a sodium acetate aqueous solution during the process. After the addition, the coupling reaction was slowly continued to the end point, and the reaction system was subjected to a loop-permeation test with a 0.5% aqueous solution of H acid until the test was negative. Filtering, and washing a filter cake to be neutral by water.
And adding all the coupling filter cakes into 1600 parts of water, pulping for 0.5 hour, adding 130 parts of 32% hydrochloric acid, and heating to 80-85 ℃ for heat preservation for 4-6 hours. And (3) cooling, adjusting the pH value to 8-9 by using a sodium carbonate aqueous solution, and filtering to obtain 244 parts (dry weight) of 4-amino-4' -nitro-3-methylazobenzene, wherein the content of the liquid chromatography is 97.61%.
Example 4
The procedure of this example was the same as example 1 except that the nitro group was reduced in a different manner from example 1.
Synthesis of 4, 4' -diamino-3-methylazobenzene: 120 parts of 60% sodium sulfide is added to 600 parts of water, the temperature is raised to 85 ℃, and 26 parts of sulfur powder is slowly added at the temperature. Heating to 90 ℃, preserving the temperature until the sulfur powder is completely dissolved, cooling to 60 ℃, and filtering to remove insoluble substances to obtain an Na2S2 aqueous solution.
Adding 200 parts (dry weight) of 4-amino-4' -nitro-3-methylazobenzene into 1400 parts of water, slowly heating to 60 ℃ while stirring, then dropwise adding the prepared Na2S2 aqueous solution, releasing heat, controlling the temperature below 70 ℃, slowly heating to 90 ℃ after adding, and keeping the temperature for 6 hours. The temperature is reduced to below 40 ℃, and 163 parts (by dry weight) of 4, 4' -diamino-3-methyl azobenzene are obtained by filtering and washing.
Example 5:
c.i. synthesis of pigment yellow 109: 275 parts of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate prepared in example 1 were added to 2000 parts of methanol, stirred for 0.5 hour, then 170 parts of 30% sodium methoxide methanol solution were added, the batch was slowly warmed to 40 ℃ and reacted at this temperature until the batch was completely dissolved.
56 parts of 2-methyl-1, 3-phenylenediamine is added into the methanol solution of the 3, 3-dimethoxy-4, 5,6, 7-tetrachloroisoindolinone, the mixture is stirred at low temperature until the mixture is completely dissolved, the temperature is slowly increased to reflux for 4 hours, and the mixture is cooled and filtered.
Pigmentation and surface treatment: adding the crude pigment product into 2000 parts of dichlorobenzene, pulping uniformly, and adjusting the pH value to 3-4 by using acetic acid. Heating to 120 deg.C, treating for 4 hr, cooling to below 40 deg.C, and filtering. The filter cake was washed with 500 parts of methanol, and then washed with water, dried and pulverized to obtain 283 parts of c.i. pigment yellow 109 as a finished product.
Example 6
C.i. synthesis of pigment yellow 110: 275 parts of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate prepared in example 1 were added to 2000 parts of methanol, stirred for 0.5 hour, then 170 parts of 30% sodium methoxide methanol solution were added, the mixture was slowly warmed to 40 ℃ and reacted at this temperature until the whole of the mixture was dissolved.
Adding 50 parts of 2-methyl-1, 3-phenylenediamine into the methanol solution of the 3, 3-dimethoxy-4, 5,6, 7-tetrachloroisoindolinone, stirring at low temperature until the mixture is completely dissolved, slowly heating to reflux for 4 hours, cooling, adjusting the pH value to 3-4 with acetic acid, and filtering. And then, the mixture is washed, dried and crushed to obtain 278 parts of C.I. pigment yellow 110 finished product.
In summary, the following steps: the invention provides a synthesis process for redesigning and optimizing 2,3,4, 5-tetrachloro-6-cyanobenzoate and 4, 4' -diamino-3-methylazobenzene, and solves the problem of complicated synthesis steps of C.I. pigment orange 61.
The present invention is not limited to the above-described embodiments, and various changes and modifications of the present invention are intended to be included within the scope of the claims and the equivalent technology of the present invention if they do not depart from the spirit and scope of the present invention.
Claims (12)
1. A method for synthesizing c.i. pigment orange 61, comprising the steps of:
s1, synthesis of methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate: performing chlorination reaction on tetrachlorophthalic anhydride to obtain light green chlorination liquid; and then slowly dropwise adding the chlorinated solution into a methanol solution of ammonia water for reaction to obtain a crude product, dissolving the crude product in a first solvent, filtering out insoluble substances while the crude product is hot, and recrystallizing mother liquor to obtain 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester, wherein the molecular structure of the 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester is as follows:
synthesis of S2, 4-amino-4' -nitro-3-methylazobenzene: adding nitroaniline into hydrochloric acid, stirring until the material is grey white slurry, then adding an ice water mixture into the mixture, cooling the mixture to below 5 ℃, then dropwise adding a sodium nitrite aqueous solution to perform diazotization reaction to obtain a diazonium salt aqueous solution, using sulfamic acid to destroy excessive sodium nitrite in the system, dissolving m-aminotoluene in a second solvent in advance, controlling the temperature, dropwise adding the diazonium salt to perform coupling reaction, finally using a deacidification agent to adjust the pH value so that the coupling reaction continues to the end point, filtering to obtain a coupling material filter cake, dissolving the coupling filter cake in a third solvent, using acid to adjust the pH value, heating up the solution to perform rearrangement reaction to obtain 4-amino-4' -nitro-3-methylazobenzene;
synthesis of S3, 4' -diamino-3-methylazobenzene: mixing the 4-amino-4 ' -nitro-3-methylazobenzene with a solvent, adding a catalyst, and reducing the 4,4 ' -diamino-3-methylazobenzene by using a reducing agent, wherein the molecular structure of the 4,4 ' -diamino-3-methylazobenzene is as follows:
synthesis of S4, 3-dialkoxy-4, 5,6, 7-tetrachloroisoindolinone: dispersing 2,3,4, 5-tetrachloro-6-cyanobenzoic acid methyl ester into a solvent IV, then adding sodium alkoxide, controlling the reaction temperature, and reacting until the materials are completely dissolved;
s5, c.i. crude synthesis of pigment orange 61: dissolving or dispersing 4, 4' -diamino-3-methylazobenzene in a solvent, adding the solution into a 3, 3-dialkoxy 4,5,6, 7-tetrachloroisoindolinone solution, controlling the reaction temperature to ensure that the solution reacts completely, adjusting the pH value to be acidic by using acid, precipitating the material, filtering, washing and drying to obtain a crude pigment product;
s6, pigmentation and surface treatment: and performing pigment treatment on the crude pigment to obtain C.I. pigment orange 61 with different formulations, performing surface treatment on the crude pigment with an auxiliary agent, and filtering, drying and crushing to obtain a finished product of the C.I. pigment orange 61.
2. The method as claimed in claim 1, wherein in step S1, the substances involved in the chlorination of tetrachlorophthalic anhydride include, but are not limited to, phosphorus pentachloride, phosphorus trichloride, gaseous and liquid chlorine, and phosphorus trichloride is used as the solvent.
3. The method for synthesizing c.i. pigment orange 61 as claimed in claim 1, wherein the concentration of the methanol solution of ammonia gas is 0.5% -15% in the step of S1.
4. The method of claim 1, wherein in step S1, the solvent used for refining the crude methyl 2,3,4, 5-tetrachloro-6-cyanobenzoate includes, but is not limited to, one of aliphatic alcohols such as methanol, ethanol, propanol, isobutanol, butanol and isobutanol.
5. The method of claim 1, wherein in step S2, the m-aminotoluene-dissolving solvent ii comprises one of water-soluble solvents such as acid water mixture, DMF and DMSO, and aliphatic alcohols such as methanol, ethanol, propanol, isobutanol and butanolisobutanol.
6. The method as claimed in claim 1, wherein the acid-removing agent used in the coupling reaction in step S2 comprises one of organic acid salts such as acetate and oxalate, and inorganic acid salts such as carbonic acid and phosphoric acid.
7. The method of claim 1, wherein in step S2, the rearrangement reaction solvent iii includes but is not limited to water, water-soluble solvents such as DMF and DMSO, and aliphatic alcohols such as methanol, ethanol, propanol, isobutanol and butanolisobutanol.
8. Synthesis of c.i. pigment orange 61 according to claim 1The method is characterized in that in the step S3, the catalyst comprises Fe without limitation 2+ 、Fe(OH) 3 C, Raney nickel, palladium carbon with different contents and platinum carbon.
9. The method of claim 1, wherein in step S3, the reducing agent comprises one of iron powder, zinc powder, sodium sulfide, hydrosulfide, polysulfide and hydrogen.
10. The method as claimed in claim 1, wherein in step S4, the sodium alkoxide includes, but is not limited to, one of sodium alkoxides such as sodium methoxide, sodium ethoxide, and sodium propoxide.
11. The method of claim 1, wherein in step S6, the pigmentation process comprises, without limitation, one of conventional and non-conventional processes such as acid swelling, acid dissolution, solvent treatment, sand milling, salt milling and ball milling.
12. The method for synthesizing c.i. pigment orange 61 as claimed in claim 1, wherein in step S6, the auxiliary agent includes one of, but not limited to, anionic surfactant, cationic surfactant and nonionic surfactant.
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Citations (4)
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BE789266A (en) * | 1971-09-27 | 1973-03-26 | Ciba Geigy | AZOIC COLORANTS |
CN109722260A (en) * | 2017-10-31 | 2019-05-07 | 捷恩智株式会社 | Light orientation aligning agent for liquid crystal, liquid crystal orientation film and its application and azobenzene derivatives, diamines and polymer |
CN110818591A (en) * | 2019-11-15 | 2020-02-21 | 彩客化学(沧州)有限公司 | Preparation method of methyl 3,4,5, 6-tetrachloro-2-cyanobenzoate |
CN114196227A (en) * | 2021-12-29 | 2022-03-18 | 百合花集团股份有限公司 | Process for the preparation of isoindolinone pigments |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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BE789266A (en) * | 1971-09-27 | 1973-03-26 | Ciba Geigy | AZOIC COLORANTS |
CN109722260A (en) * | 2017-10-31 | 2019-05-07 | 捷恩智株式会社 | Light orientation aligning agent for liquid crystal, liquid crystal orientation film and its application and azobenzene derivatives, diamines and polymer |
CN110818591A (en) * | 2019-11-15 | 2020-02-21 | 彩客化学(沧州)有限公司 | Preparation method of methyl 3,4,5, 6-tetrachloro-2-cyanobenzoate |
CN114196227A (en) * | 2021-12-29 | 2022-03-18 | 百合花集团股份有限公司 | Process for the preparation of isoindolinone pigments |
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