DE2109923A1 - Verfahren zur Herstellung von 1,1 -Peroxy dicy clohexy lamin - Google Patents
Verfahren zur Herstellung von 1,1 -Peroxy dicy clohexy laminInfo
- Publication number
- DE2109923A1 DE2109923A1 DE19712109923 DE2109923A DE2109923A1 DE 2109923 A1 DE2109923 A1 DE 2109923A1 DE 19712109923 DE19712109923 DE 19712109923 DE 2109923 A DE2109923 A DE 2109923A DE 2109923 A1 DE2109923 A1 DE 2109923A1
- Authority
- DE
- Germany
- Prior art keywords
- salt
- acid
- hydrogen peroxide
- cyclohexanone
- reaction
- 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 24
- 238000004519 manufacturing process Methods 0.000 title description 3
- 102000006835 Lamins Human genes 0.000 title 1
- 108010047294 Lamins Proteins 0.000 title 1
- 210000005053 lamin Anatomy 0.000 title 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 37
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- -1 alkaline earth metal salt Chemical class 0.000 claims description 3
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 229960004365 benzoic acid Drugs 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- 150000002978 peroxides Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MAYPHUUCLRDEAZ-UHFFFAOYSA-N chlorine peroxide Chemical compound ClOOCl MAYPHUUCLRDEAZ-UHFFFAOYSA-N 0.000 description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 description 1
- BURBNIPKSRJAIQ-UHFFFAOYSA-N 2-azaniumyl-3-[3-(trifluoromethyl)phenyl]propanoate Chemical compound OC(=O)C(N)CC1=CC=CC(C(F)(F)F)=C1 BURBNIPKSRJAIQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000000233 Melia azedarach Species 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229940090948 ammonium benzoate Drugs 0.000 description 1
- 229940063284 ammonium salicylate Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- KHIHBOPGYSBYJJ-UHFFFAOYSA-N azane;toluene Chemical compound N.CC1=CC=CC=C1 KHIHBOPGYSBYJJ-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GVARKRUZKAZPOZ-UHFFFAOYSA-L calcium;4-methylbenzenesulfonate Chemical compound [Ca+2].CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 GVARKRUZKAZPOZ-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1034370A GB1284181A (en) | 1970-03-04 | 1970-03-04 | Production of 1,1'-peroxydicyclohexylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2109923A1 true DE2109923A1 (de) | 1971-09-30 |
Family
ID=9966105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712109923 Pending DE2109923A1 (de) | 1970-03-04 | 1971-03-02 | Verfahren zur Herstellung von 1,1 -Peroxy dicy clohexy lamin |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE763810R (enExample) |
| DE (1) | DE2109923A1 (enExample) |
| FR (1) | FR2084116A6 (enExample) |
| GB (1) | GB1284181A (enExample) |
| IT (1) | IT986786B (enExample) |
| NL (1) | NL7102853A (enExample) |
-
1970
- 1970-03-04 GB GB1034370A patent/GB1284181A/en not_active Expired
-
1971
- 1971-03-02 DE DE19712109923 patent/DE2109923A1/de active Pending
- 1971-03-03 IT IT2127871A patent/IT986786B/it active
- 1971-03-03 NL NL7102853A patent/NL7102853A/xx unknown
- 1971-03-03 FR FR7107241A patent/FR2084116A6/fr not_active Expired
- 1971-03-04 BE BE763810A patent/BE763810R/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| BE763810R (fr) | 1971-09-06 |
| NL7102853A (enExample) | 1971-09-07 |
| GB1284181A (en) | 1972-08-02 |
| FR2084116A6 (enExample) | 1971-12-17 |
| IT986786B (it) | 1975-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE4310947A1 (de) | Oxidatives Quenchverfahren für 2-Perfluoralkylethylalkohole | |
| DE1942264C3 (de) | Polyfluorsulfonsäuren und deren Sulfonate, Verfahren zur Herstellung der Polyfluorsulfonate, sowie Verwendung der genannten Verbindungen als oberflächenaktive Mittel | |
| DE19503900C1 (de) | Verfahren zur Herstellung des Kaliumperoxomonosulfat-Tripelsalzes 2 KHSO¶5¶ . KHSO¶4¶ . K¶2¶SO¶4¶ | |
| DE68904760T2 (de) | Regeneration von erschoepften schwefelsaeuren mittels wasserstoffperoxyd. | |
| DE2109923A1 (de) | Verfahren zur Herstellung von 1,1 -Peroxy dicy clohexy lamin | |
| DE3013888A1 (de) | Verfahren zur herstellung von trichlorbenzolen | |
| EP0179223A1 (de) | Verfahren zur Herstellung stabilisierter substituierter Diperoxybernsteinsäuren | |
| DE2258530A1 (de) | Verfahren zur herstellung von 4.4'dinitrostilben-2.2'-disulphonsaeure | |
| DE2148597A1 (de) | Perfluoralkylsulfinsaeuren und verfahren zu ihrer herstellung | |
| DE870853C (de) | Verfahren zur Herstellung von Diisopropylbenzolhydroperoxyden | |
| DE2649744C3 (de) | Verfahren zur Herstellung von Indolin | |
| DE2044854C3 (de) | Verfahren zur Herstellung von CC-ungesättigten organischen Verbindungen durch Zersetzen der Xanthogenatester von entsprechenden Alkoholen | |
| DE3101650C2 (de) | Verfahren zur Herstellung von reinem, lagerbeständigem Acetoacetamid | |
| DE2202204A1 (de) | Verfahren zur kontinuierlichen herstellung von 2-mercaptobenzimidazol | |
| DE2062054A1 (enExample) | ||
| DE69314637T2 (de) | Verfahren zur herstellung und wiedergewinnung von halogennitroalkanen in hoher ausbeute | |
| DE1217947B (de) | Verfahren zur Herstellung von 2, 3-Dichlorbutadien-(1, 3) | |
| DE2015760A1 (de) | Verfahren zur Herstellung von Glucofuranosiden | |
| DE2049560C3 (de) | Verfahren zur Herstellung von I,T-Peroxydicyclohexylaniin | |
| DE1720519B2 (de) | Verfahren zur herstellung von polyestern | |
| DE1720519C3 (de) | Verfahren zur Herstellung von Polyestern | |
| DE1695503B2 (de) | Verfahren zur herstellung von 1,1'-peroxydicyclohexylamin | |
| DE2120248A1 (enExample) | ||
| DE2310744C2 (de) | Verfahren zur Herstellung von 2-Chlorbutadien-(l,3) | |
| DE171789C (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |