BE526830A

BE526830A -

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Publication number: BE526830A
Authority: BE; Belgium
Prior art keywords: sep; residue; dyes; parts; dye
Prior art date

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English (en)

French (fr)

Publication of BE526830A publication Critical patent/BE526830A/fr

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239000000975 dye Substances 0.000 claims description 61
239000011651 chromium Substances 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 24
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 22
229910052803 cobalt Inorganic materials 0.000 claims description 22
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 20
229910052804 chromium Inorganic materials 0.000 claims description 19
239000010941 cobalt Substances 0.000 claims description 19
230000001808 coupling Effects 0.000 claims description 18
238000010168 coupling process Methods 0.000 claims description 18
238000005859 coupling reaction Methods 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 9
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 7
238000004043 dyeing Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
125000000565 sulfonamide group Chemical group 0.000 claims description 6
125000004429 atoms Chemical group 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 4
239000000987 azo dye Substances 0.000 claims description 4
239000000463 material Substances 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 135
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 21
239000002253 acid Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
-1 sulfonic acid halides Chemical class 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
239000000843 powder Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000003085 diluting agent Substances 0.000 description 10
210000002268 Wool Anatomy 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
238000005917 acylation reaction Methods 0.000 description 7
239000011574 phosphorus Substances 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
229950011260 betanaphthol Drugs 0.000 description 6
238000009835 boiling Methods 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
238000001465 metallisation Methods 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229960000583 Acetic Acid Drugs 0.000 description 5
UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 5
FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000002585 base Substances 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
229940113083 morpholine Drugs 0.000 description 5
230000001264 neutralization Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
229960001663 sulfanilamide Drugs 0.000 description 5
238000005406 washing Methods 0.000 description 5
RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 4
229940093912 Gynecological Sulfonamides Drugs 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating Effects 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 4
229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
150000003018 phosphorus compounds Chemical class 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
150000003456 sulfonamides Chemical class 0.000 description 4
229940026752 topical Sulfonamides Drugs 0.000 description 4
PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000003701 inert diluent Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
239000012265 solid product Substances 0.000 description 3
230000001131 transforming Effects 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-Dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KTVIXTQDYHMGHF-UHFFFAOYSA-L Cobalt(II) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
150000001845 chromium compounds Chemical class 0.000 description 2
150000001869 cobalt compounds Chemical class 0.000 description 2
229940044175 cobalt sulfate Drugs 0.000 description 2
229910000361 cobalt sulfate Inorganic materials 0.000 description 2
230000000875 corresponding Effects 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
230000002140 halogenating Effects 0.000 description 2
238000002955 isolation Methods 0.000 description 2
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
DKZIEDUMSPGDCI-UHFFFAOYSA-N oxo(phenyl)methanesulfonyl chloride Chemical compound ClS(=O)(=O)C(=O)C1=CC=CC=C1 DKZIEDUMSPGDCI-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N triclene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
ODIGIKRIUKFKHP-UHFFFAOYSA-N (N-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
NZRLCYJRHKUVCV-UHFFFAOYSA-N 1-chloro-2-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=CC=C1Cl NZRLCYJRHKUVCV-UHFFFAOYSA-N 0.000 description 1
OZFUEQNYOBIXTB-VJOYVCHSSA-N 2-[(2E,5E)-5-[[4-[4-(2,2-diphenylethenyl)phenyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indol-7-yl]methylidene]-2-(3-ethyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)-4-oxo-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC)C(=S)S\C1=C(\S\1)N(CC(O)=O)C(=O)C/1=C\C1=CC=C(N(C2C3CCC2)C=2C=CC(C=C(C=4C=CC=CC=4)C=4C=CC=CC=4)=CC=2)C3=C1 OZFUEQNYOBIXTB-VJOYVCHSSA-N 0.000 description 1
SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 description 1
WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 1
ZSUDUDXOEGHEJR-UHFFFAOYSA-N 4-methylnaphthalen-1-ol Chemical compound C1=CC=C2C(C)=CC=C(O)C2=C1 ZSUDUDXOEGHEJR-UHFFFAOYSA-N 0.000 description 1
KEGNUIZNBCHWLZ-UHFFFAOYSA-N 5,8-dichloronaphthalen-1-ol Chemical compound C1=CC(Cl)=C2C(O)=CC=CC2=C1Cl KEGNUIZNBCHWLZ-UHFFFAOYSA-N 0.000 description 1
DYRDKSSFIWVSNM-UHFFFAOYSA-N Acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N Anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
WURBFLDFSFBTLW-UHFFFAOYSA-N Benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N Butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
MZPMHUVLWMEWJZ-UHFFFAOYSA-N COC=1C=C2C(=CC(=C(C2=CC1)N)O)S(=O)(=O)O Chemical compound COC=1C=C2C(=CC(=C(C2=CC1)N)O)S(=O)(=O)O MZPMHUVLWMEWJZ-UHFFFAOYSA-N 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N Chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
ASKVAEGIVYSGNY-UHFFFAOYSA-L Cobalt(II) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
229940117389 Dichlorobenzene Drugs 0.000 description 1
229940093915 Gynecological Organic acids Drugs 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
MVHWDVWOLCKUNF-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=C(C2=CC=CC=C12)S(=O)(=O)O)O Chemical compound [N+](=O)([O-])C1=C(C=C(C2=CC=CC=C12)S(=O)(=O)O)O MVHWDVWOLCKUNF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000003855 acyl compounds Chemical class 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000000240 adjuvant Effects 0.000 description 1
229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000011449 brick Substances 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000005591 charge neutralization Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009838 combustion analysis Methods 0.000 description 1
230000027326 copulation Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000001747 exhibiting Effects 0.000 description 1
230000002349 favourable Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000010985 leather Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
238000007747 plating Methods 0.000 description 1
230000001376 precipitating Effects 0.000 description 1
230000001737 promoting Effects 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000001047 purple dye Substances 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1