DE2050991A1 - Verfahren zur Herstellung von 2,2 Methylen bis (3,4,6 tnchlorophenol) - Google Patents
Verfahren zur Herstellung von 2,2 Methylen bis (3,4,6 tnchlorophenol)Info
- Publication number
- DE2050991A1 DE2050991A1 DE19702050991 DE2050991A DE2050991A1 DE 2050991 A1 DE2050991 A1 DE 2050991A1 DE 19702050991 DE19702050991 DE 19702050991 DE 2050991 A DE2050991 A DE 2050991A DE 2050991 A1 DE2050991 A1 DE 2050991A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- solution
- hexachlorophene
- mole
- formaldehyde
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 2,2 methylene Chemical group 0.000 title claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 claims description 6
- 229960004068 hexachlorophene Drugs 0.000 claims description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 3
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 230000001180 sulfating effect Effects 0.000 claims 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- XTRQTTPULQZHJH-UHFFFAOYSA-N chloro phenyl sulfate Chemical compound ClOS(=O)(=O)OC1=CC=CC=C1 XTRQTTPULQZHJH-UHFFFAOYSA-N 0.000 claims 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 3
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
- 241001155433 Centrarchus macropterus Species 0.000 description 1
- MWJLDBVTCZLCCG-UHFFFAOYSA-N S(=O)(=O)(O)OC1=C(C(=C(C=C1)Cl)Cl)Cl Chemical compound S(=O)(=O)(O)OC1=C(C(=C(C=C1)Cl)Cl)Cl MWJLDBVTCZLCCG-UHFFFAOYSA-N 0.000 description 1
- WCTKUENARPWTAY-UHFFFAOYSA-N ac1l9mss Chemical compound OS(Cl)=O WCTKUENARPWTAY-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/115—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using acetals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1787070A | 1970-03-09 | 1970-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2050991A1 true DE2050991A1 (de) | 1971-09-23 |
Family
ID=21784993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702050991 Pending DE2050991A1 (de) | 1970-03-09 | 1970-10-16 | Verfahren zur Herstellung von 2,2 Methylen bis (3,4,6 tnchlorophenol) |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2050991A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2083879A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1258550A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0745575B1 (en) * | 1995-06-02 | 2000-09-06 | Fuji Photo Film Co., Ltd. | Method of synthesizing polyphenol compound and positive working photoresist composition comprising polyphenol compound |
-
1970
- 1970-10-13 GB GB1258550D patent/GB1258550A/en not_active Expired
- 1970-10-16 DE DE19702050991 patent/DE2050991A1/de active Pending
-
1971
- 1971-01-26 FR FR7102529A patent/FR2083879A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2083879A5 (enrdf_load_stackoverflow) | 1971-12-17 |
| GB1258550A (enrdf_load_stackoverflow) | 1971-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69214889T2 (de) | Verfahren zur Herstellung von Bisphenol A | |
| DE2326784B2 (de) | Verfahren zur Herstellung von Chinoxalin, insbesondere aus nicht gereinigten Rohstoffen | |
| DE2727345C2 (de) | Verfahren zur Herstellung von 8-Amino-1-naphthol-3,6-disulfonsäure | |
| DE69013061T2 (de) | Verfahren zur Herstellung von Kohlensäureestern. | |
| DE1543637C3 (de) | Verfahren zur Herstellung farbloser kristalliner Diphenylsulfone | |
| DE2419455A1 (de) | Verfahren zur herstellung von pnitrotoluol-2-sulfonsaeure | |
| DE1942459A1 (de) | Kontinuierliches Verfahren zur Herstellung von Methylendianilin | |
| DE2050991A1 (de) | Verfahren zur Herstellung von 2,2 Methylen bis (3,4,6 tnchlorophenol) | |
| DE2319493C3 (de) | Verfahren zur Gewinnung von optisch aktivem a -Phenylglycin-benzolsulfonat durch optische Aufspaltung von DL- a -Phenylglycinbenzolsulfonat | |
| DE2027599A1 (de) | Verfahren zur Herstellung von substi tuierten Acrylsaureamiden | |
| DE659729C (de) | Verfahren zur Herstellung von Methacrylsaeure und deren Estern | |
| DE3873983T2 (de) | Verfahren zur herstellung von halogenierten imiden. | |
| DE3875545T2 (de) | Verfahren zur herstellung von substituierten phthalsaeureanhydriden. | |
| DE572723C (de) | Verfahren zur Darstellung von Chlor- und Bromderivaten der 2-Aminonaphthalin-1-sulfonsaeure | |
| DE3236144A1 (de) | Verfahren zur herstellung von vinkaminsaeureestern | |
| DE68924323T2 (de) | Verfahren zur Herstellung von 2-Thiocyanatomethylthiobenzthiazol. | |
| DE836039C (de) | Verfahren zur Chlorierung von Essigsaeure | |
| DE1076669B (de) | Verfahren zur Herstellung von 2-Chlorbutadien-1, 3 | |
| DE881039C (de) | Verfahren zur Herstellung des Pentaerythrit-dichlorhydrin-monoschwefligsaeureesters | |
| DE404175C (de) | Verfahren zur Herstellung von Sulfocyanverbindungen | |
| DE2403664C3 (de) | Verfahren zur Reindarstellung von Naphthalin | |
| DE245892C (enrdf_load_stackoverflow) | ||
| WO1991007383A1 (de) | VERFAHREN ZUR HYDROLYSE VON α-NAPHTHALINSULFONSÄURE IN EINEM NAPHTHALIN-SULFONIERGEMISCH | |
| DE2612504A1 (de) | Verfahren zur herstellung von basischen aluminiumloesungen und verwendung dieser loesungen | |
| DE636259C (de) | Verfahren zur Herstellung von Schwefelsaeureverbindungen aus polymerisierten ungesaettigten Oxyfettsaeuren |