DE132607C - - Google Patents

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Publication number

DE132607C

DE132607C DENDAT132607D DE132607DA DE132607C DE 132607 C DE132607 C DE 132607C DE NDAT132607 D DENDAT132607 D DE NDAT132607D DE 132607D A DE132607D A DE 132607DA DE 132607 C DE132607 C DE 132607C

Authority

DE

Germany

Prior art keywords

acid

autoclave

heated

catechol

sodium

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.)

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• ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims description 18
• YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
• -1 pyrocatechol monoethyl sulfonic acid Chemical compound 0.000 claims description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
• 239000007864 aqueous solution Substances 0.000 claims description 4
• HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
• QDRCGSIKAHSALR-UHFFFAOYSA-N 4-hydroxy-3-methoxybenzene-1-sulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1O QDRCGSIKAHSALR-UHFFFAOYSA-N 0.000 claims description 3
• 239000002253 acid Substances 0.000 claims description 3
• 239000003518 caustics Substances 0.000 claims description 3
• 229940057818 guaiacolsulfonic acid Drugs 0.000 claims description 3
• 238000010438 heat treatment Methods 0.000 claims description 3
• 238000005987 sulfurization reaction Methods 0.000 claims description 3
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
• 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
• LULCPJWUGUVEFU-UHFFFAOYSA-N Phthiocol Natural products C1=CC=C2C(=O)C(C)=C(O)C(=O)C2=C1 LULCPJWUGUVEFU-UHFFFAOYSA-N 0.000 claims description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
• 230000008030 elimination Effects 0.000 claims description 2
• 238000003379 elimination reaction Methods 0.000 claims description 2
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• 239000011591 potassium Substances 0.000 claims description 2
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
• 239000000047 product Substances 0.000 claims description 2
• 238000000926 separation method Methods 0.000 claims description 2
• 150000003460 sulfonic acids Chemical class 0.000 claims description 2
• 239000011734 sodium Substances 0.000 claims 4
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
• 229910052708 sodium Inorganic materials 0.000 claims 3
• QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 claims 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
• 239000013078 crystal Substances 0.000 claims 2
• 238000005185 salting out Methods 0.000 claims 2
• 159000000000 sodium salts Chemical class 0.000 claims 2
• 239000000243 solution Substances 0.000 claims 2
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
• FOLDWDMBUATQRL-UHFFFAOYSA-N benzene-1,2-diol;methanesulfonic acid Chemical compound CS(O)(=O)=O.OC1=CC=CC=C1O FOLDWDMBUATQRL-UHFFFAOYSA-N 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 claims 1
• 238000003776 cleavage reaction Methods 0.000 claims 1
• 238000001816 cooling Methods 0.000 claims 1
• 238000002425 crystallisation Methods 0.000 claims 1
• 230000008025 crystallization Effects 0.000 claims 1
• 238000000605 extraction Methods 0.000 claims 1
• 229940072033 potash Drugs 0.000 claims 1
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
• 235000015320 potassium carbonate Nutrition 0.000 claims 1
• 239000002244 precipitate Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 claims 1
• 230000007017 scission Effects 0.000 claims 1
• 229910052709 silver Inorganic materials 0.000 claims 1
• 239000004332 silver Substances 0.000 claims 1
• ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims 1
• 235000002639 sodium chloride Nutrition 0.000 claims 1
• 239000011780 sodium chloride Substances 0.000 claims 1
• 235000011121 sodium hydroxide Nutrition 0.000 claims 1
• 239000007858 starting material Substances 0.000 claims 1
• 229910021653 sulphate ion Inorganic materials 0.000 claims 1
• 239000006188 syrup Substances 0.000 claims 1
• 235000020357 syrup Nutrition 0.000 claims 1
• LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 16
• 229960001867 guaiacol Drugs 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 230000011987 methylation Effects 0.000 description 1
• 238000007069 methylation reaction Methods 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• 230000000630 rising effect Effects 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 238000010025 steaming Methods 0.000 description 1