DE2405782C3 - Verfahren zur Herstellung von l-Amino^-alkoxy^-hydroxy-anthrachinonen - Google Patents
Verfahren zur Herstellung von l-Amino^-alkoxy^-hydroxy-anthrachinonenInfo
- Publication number
- DE2405782C3 DE2405782C3 DE2405782A DE2405782A DE2405782C3 DE 2405782 C3 DE2405782 C3 DE 2405782C3 DE 2405782 A DE2405782 A DE 2405782A DE 2405782 A DE2405782 A DE 2405782A DE 2405782 C3 DE2405782 C3 DE 2405782C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- amino
- reaction
- hours
- potash
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 62
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 22
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- -1 aliphatic alcohols Chemical class 0.000 claims description 15
- 150000003138 primary alcohols Chemical class 0.000 claims description 14
- 229920001223 polyethylene glycol Polymers 0.000 claims description 13
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- MSSQDESMUMSQEN-UHFFFAOYSA-N 1-amino-2-bromo-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Br)=C2N MSSQDESMUMSQEN-UHFFFAOYSA-N 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 105
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 68
- 229940072033 potash Drugs 0.000 description 51
- 235000015320 potassium carbonate Nutrition 0.000 description 51
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 37
- 239000000975 dye Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 229910000027 potassium carbonate Inorganic materials 0.000 description 27
- 235000011181 potassium carbonates Nutrition 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 9
- 229920000151 polyglycol Polymers 0.000 description 9
- 239000010695 polyglycol Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- MFAVJLWGAQYYNX-UHFFFAOYSA-N 1-amino-2-chloro-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Cl)=C2N MFAVJLWGAQYYNX-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- WSPPHHAIMCTKNN-UHFFFAOYSA-N 1-amino-4-hydroxy-2-methoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(O)=C3C(=O)C2=C1 WSPPHHAIMCTKNN-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
- 239000012084 conversion product Substances 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- OMNKOGMRWWOOFR-UHFFFAOYSA-N 5-methoxypentan-1-ol Chemical compound COCCCCCO OMNKOGMRWWOOFR-UHFFFAOYSA-N 0.000 description 2
- CROLBRYGLOVQCD-UHFFFAOYSA-N 6-methoxyhexan-1-ol Chemical compound COCCCCCCO CROLBRYGLOVQCD-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- KMHIOVLPRIUBGK-UHFFFAOYSA-N butane-1,4-diol;hexane-1,6-diol Chemical compound OCCCCO.OCCCCCCO KMHIOVLPRIUBGK-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229960005323 phenoxyethanol Drugs 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WMRZILBVZQDQNQ-UHFFFAOYSA-N 1-amino-2-(2-ethylhexoxy)-4-hydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCC(CC)CCCC)=CC(O)=C3C(=O)C2=C1 WMRZILBVZQDQNQ-UHFFFAOYSA-N 0.000 description 1
- KXTXJBJDBWXSEX-UHFFFAOYSA-N 1-amino-2-[2-ethyl-2-(hydroxymethyl)hexoxy]-4-hydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCC(CC)(CO)CCCC)=CC(O)=C3C(=O)C2=C1 KXTXJBJDBWXSEX-UHFFFAOYSA-N 0.000 description 1
- RPNPABHCHFGIPJ-UHFFFAOYSA-N 1-amino-2-dodecoxy-4-hydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCCCCCCCCCCCC)=CC(O)=C3C(=O)C2=C1 RPNPABHCHFGIPJ-UHFFFAOYSA-N 0.000 description 1
- YNSMMVQJQULRFZ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(2-hydroxyethoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(OCCO)=C2N YNSMMVQJQULRFZ-UHFFFAOYSA-N 0.000 description 1
- DZOOLKFVBAJJGQ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(2-phenylethoxy)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OCCC1=CC=CC=C1 DZOOLKFVBAJJGQ-UHFFFAOYSA-N 0.000 description 1
- WRPOHHBXCRBNMK-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(3-hydroxy-2,2-dimethylhexoxy)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCC(C)(C)C(O)CCC)=CC(O)=C3C(=O)C2=C1 WRPOHHBXCRBNMK-UHFFFAOYSA-N 0.000 description 1
- ZNJYHPGKRWKHJT-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(3-hydroxy-5,5-dimethylhexoxy)anthracene-9,10-dione Chemical compound NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)O)OCCC(CC(C)(C)C)O ZNJYHPGKRWKHJT-UHFFFAOYSA-N 0.000 description 1
- MNLOKIGKRGKOIF-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(5-hydroxypentoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(OCCCCCO)=C2N MNLOKIGKRGKOIF-UHFFFAOYSA-N 0.000 description 1
- RQLMZSLFKGNXTO-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(6-hydroxyhexoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(OCCCCCCO)=C2N RQLMZSLFKGNXTO-UHFFFAOYSA-N 0.000 description 1
- LGEKCCSOHUOMBO-UHFFFAOYSA-N 1-amino-4-hydroxy-2-[2-(hydroxymethyl)-2-methylpentoxy]anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCC(C)(CO)CCC)=CC(O)=C3C(=O)C2=C1 LGEKCCSOHUOMBO-UHFFFAOYSA-N 0.000 description 1
- FWIHJNNCNRANGQ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-octoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCCCCCCCC)=CC(O)=C3C(=O)C2=C1 FWIHJNNCNRANGQ-UHFFFAOYSA-N 0.000 description 1
- UZHMMSBDIXSBOW-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenylmethoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OCC1=CC=CC=C1 UZHMMSBDIXSBOW-UHFFFAOYSA-N 0.000 description 1
- UBPITMWKFIAENS-UHFFFAOYSA-N 1-amino-4-hydroxy-2-propoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCCC)=CC(O)=C3C(=O)C2=C1 UBPITMWKFIAENS-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- JAOJIOKHVNIXSI-UHFFFAOYSA-N 2,2-dimethylhexane-1,1-diol Chemical compound CCCCC(C)(C)C(O)O JAOJIOKHVNIXSI-UHFFFAOYSA-N 0.000 description 1
- OIJIFUUFCFXEFW-UHFFFAOYSA-N 2,4-diphenylpentan-1-ol Chemical compound C=1C=CC=CC=1C(C)CC(CO)C1=CC=CC=C1 OIJIFUUFCFXEFW-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- RNDNSYIPLPAXAZ-UHFFFAOYSA-N 2-Phenyl-1-propanol Chemical compound OCC(C)C1=CC=CC=C1 RNDNSYIPLPAXAZ-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- DNHNBMQCHKKDNI-UHFFFAOYSA-N 2-phenylbutan-1-ol Chemical compound CCC(CO)C1=CC=CC=C1 DNHNBMQCHKKDNI-UHFFFAOYSA-N 0.000 description 1
- HICVLDGMWDLPEH-UHFFFAOYSA-N 2-phenylhexan-1-ol Chemical compound CCCCC(CO)C1=CC=CC=C1 HICVLDGMWDLPEH-UHFFFAOYSA-N 0.000 description 1
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 description 1
- SQGBBDFDRHDJCJ-UHFFFAOYSA-N 3-phenylbutan-1-ol Chemical compound OCCC(C)C1=CC=CC=C1 SQGBBDFDRHDJCJ-UHFFFAOYSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- XAZAHJGDOHGFBV-UHFFFAOYSA-N 7-hydroxyheptanenitrile Chemical compound OCCCCCCC#N XAZAHJGDOHGFBV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- IGGPPYMUTYUYAR-UHFFFAOYSA-N [1-(hydroxymethyl)-2,3-dihydroinden-1-yl]methanol Chemical compound C1=CC=C2C(CO)(CO)CCC2=C1 IGGPPYMUTYUYAR-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AZJXQVRPBZSNFN-UHFFFAOYSA-N octane-3,3-diol Chemical compound CCCCCC(O)(O)CC AZJXQVRPBZSNFN-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229950009195 phenylpropanol Drugs 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2405782A DE2405782C3 (de) | 1974-02-07 | 1974-02-07 | Verfahren zur Herstellung von l-Amino^-alkoxy^-hydroxy-anthrachinonen |
| CH133775A CH620234A5 (en) | 1974-02-07 | 1975-02-04 | Process for the preparation of anthraquinone compounds |
| IT48045/75A IT1029498B (it) | 1974-02-07 | 1975-02-06 | Procedimento per la produzione di i ammino 2 alcossi 4 idrrossian trachinoni |
| GB5053/75A GB1492852A (en) | 1974-02-07 | 1975-02-06 | Manufacture of 1-amino-2-alkoxy-4-hydroxyanthraquinones |
| FR7503886A FR2260562B3 (en, 2012) | 1974-02-07 | 1975-02-07 | |
| JP1550675A JPS547019B2 (en, 2012) | 1974-02-07 | 1975-02-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2405782A DE2405782C3 (de) | 1974-02-07 | 1974-02-07 | Verfahren zur Herstellung von l-Amino^-alkoxy^-hydroxy-anthrachinonen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2405782A1 DE2405782A1 (de) | 1975-08-28 |
| DE2405782B2 DE2405782B2 (de) | 1979-02-01 |
| DE2405782C3 true DE2405782C3 (de) | 1979-10-04 |
Family
ID=5906826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2405782A Expired DE2405782C3 (de) | 1974-02-07 | 1974-02-07 | Verfahren zur Herstellung von l-Amino^-alkoxy^-hydroxy-anthrachinonen |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS547019B2 (en, 2012) |
| CH (1) | CH620234A5 (en, 2012) |
| DE (1) | DE2405782C3 (en, 2012) |
| FR (1) | FR2260562B3 (en, 2012) |
| GB (1) | GB1492852A (en, 2012) |
| IT (1) | IT1029498B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4485043A (en) * | 1981-07-30 | 1984-11-27 | Ciba-Geigy Ag | Process for producing 1-amino-4-hydroxy-anthraquinones |
| US4510088A (en) * | 1981-08-28 | 1985-04-09 | Ciba Geigy Corporation | Dye mixtures of anthraquinone dyes |
| DE3726983A1 (de) * | 1987-08-13 | 1989-02-23 | Basf Ag | Verfahren zur herstellung von 1-amino-4-hydroxy-2-(6'-hydroxyhexoxy)-anthrachinon |
-
1974
- 1974-02-07 DE DE2405782A patent/DE2405782C3/de not_active Expired
-
1975
- 1975-02-04 CH CH133775A patent/CH620234A5/de not_active IP Right Cessation
- 1975-02-06 GB GB5053/75A patent/GB1492852A/en not_active Expired
- 1975-02-06 IT IT48045/75A patent/IT1029498B/it active
- 1975-02-07 JP JP1550675A patent/JPS547019B2/ja not_active Expired
- 1975-02-07 FR FR7503886A patent/FR2260562B3/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS547019B2 (en, 2012) | 1979-04-03 |
| GB1492852A (en) | 1977-11-23 |
| FR2260562B3 (en, 2012) | 1977-10-21 |
| CH620234A5 (en) | 1980-11-14 |
| IT1029498B (it) | 1979-03-10 |
| DE2405782B2 (de) | 1979-02-01 |
| JPS50109924A (en, 2012) | 1975-08-29 |
| FR2260562A1 (en, 2012) | 1975-09-05 |
| DE2405782A1 (de) | 1975-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete disclaimer |