DE1804068C3 - Verfahren zur Herstellung von Bromnitroalkoholen - Google Patents
Verfahren zur Herstellung von BromnitroalkoholenInfo
- Publication number
- DE1804068C3 DE1804068C3 DE19681804068 DE1804068A DE1804068C3 DE 1804068 C3 DE1804068 C3 DE 1804068C3 DE 19681804068 DE19681804068 DE 19681804068 DE 1804068 A DE1804068 A DE 1804068A DE 1804068 C3 DE1804068 C3 DE 1804068C3
- Authority
- DE
- Germany
- Prior art keywords
- magnesium
- alkaline earth
- solution
- formula
- alcohols
- 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 13
- 150000001298 alcohols Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 alkaline earth metal salt Chemical class 0.000 claims description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 13
- 229910052749 magnesium Inorganic materials 0.000 claims description 13
- 239000011777 magnesium Substances 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
- 229960002327 chloral hydrate Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LHQKXYCMFLDMDH-UHFFFAOYSA-N 2-bromo-2-nitropropane-1,1-diol Chemical compound OC(O)C(Br)(C)[N+]([O-])=O LHQKXYCMFLDMDH-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QHFQAJHNDKBRBO-UHFFFAOYSA-L calcium chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ca+2] QHFQAJHNDKBRBO-UHFFFAOYSA-L 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR96391D FR96391E (https=) | 1968-10-19 | ||
| DE19681804068 DE1804068C3 (de) | 1968-10-19 | 1968-10-19 | Verfahren zur Herstellung von Bromnitroalkoholen |
| NLAANVRAGE6909485,A NL170411C (nl) | 1968-07-19 | 1969-06-20 | Werkwijze voor het bereiden van broomnitroalcoholen. |
| CH1046969A CH537358A (de) | 1968-07-19 | 1969-07-09 | Verfahren zur Herstellung von Bromnitroalkoholen |
| IT19758/69A IT1031002B (it) | 1968-07-19 | 1969-07-17 | Procedimento per la preparazione de bromonitroalcooli |
| US842711A US3658921A (en) | 1968-07-19 | 1969-07-17 | Process for production of halonitro alcohols |
| GB36304/69A GB1277943A (en) | 1968-07-19 | 1969-07-18 | Improvements in the production of halonitroalcohols |
| JP44056978A JPS507577B1 (https=) | 1968-07-19 | 1969-07-18 | |
| BE740376D BE740376A (https=) | 1968-10-19 | 1969-10-16 | |
| AT983069A AT305961B (de) | 1968-10-19 | 1969-10-17 | Verfahren zur Herstellung von Bromnitroalkoholen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681804068 DE1804068C3 (de) | 1968-10-19 | 1968-10-19 | Verfahren zur Herstellung von Bromnitroalkoholen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1804068A1 DE1804068A1 (de) | 1970-09-17 |
| DE1804068B2 DE1804068B2 (de) | 1977-04-07 |
| DE1804068C3 true DE1804068C3 (de) | 1978-03-30 |
Family
ID=5710969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681804068 Expired DE1804068C3 (de) | 1968-07-19 | 1968-10-19 | Verfahren zur Herstellung von Bromnitroalkoholen |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT305961B (https=) |
| BE (1) | BE740376A (https=) |
| DE (1) | DE1804068C3 (https=) |
| FR (1) | FR96391E (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4872108A (https=) * | 1971-12-27 | 1973-09-29 | ||
| DE3622976A1 (de) * | 1986-07-09 | 1988-01-21 | Bayer Ag | Fluor enthaltende dimethylolnitromethane, verfahren zu ihrer herstellung sowie ihre verwendung |
| US5243092A (en) * | 1991-09-11 | 1993-09-07 | K·I Chemical Industry Co., Ltd. | Method for producing 2,2-dibromo-2-nitroethanol |
| DE10137829A1 (de) * | 2001-08-02 | 2003-02-13 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von 2-Brom-2-nitro-1,3-propandiol |
| CN103396317B (zh) * | 2008-02-28 | 2016-04-27 | 溴化合物有限公司 | 制备拌棉醇的方法 |
-
0
- FR FR96391D patent/FR96391E/fr not_active Expired
-
1968
- 1968-10-19 DE DE19681804068 patent/DE1804068C3/de not_active Expired
-
1969
- 1969-10-16 BE BE740376D patent/BE740376A/xx unknown
- 1969-10-17 AT AT983069A patent/AT305961B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR96391E (https=) | 1972-06-16 |
| AT305961B (de) | 1973-03-26 |
| DE1804068A1 (de) | 1970-09-17 |
| DE1804068B2 (de) | 1977-04-07 |
| BE740376A (https=) | 1970-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1954173C3 (de) | Verfahren zur Herstellung von Bromnitroalkoholen | |
| DE1804068C3 (de) | Verfahren zur Herstellung von Bromnitroalkoholen | |
| DE68904928T2 (de) | Verfahren zur herstellung von 4-aryl-disubstituierten-1-tetralonen. | |
| DE2759964C2 (de) | 2,6-Dimethoxy-4-(quaternäre-alkyl)phenyl-disubstituierte-phosphate und Verfahren zu ihrer Herstellung | |
| DE69010297T2 (de) | Verfahren zur Herstellung von Isothiazolinonen durch Cyclisierung. | |
| DE2362694C3 (de) | Verfahren zur Herstellung von Phloroglucin bzw. dessen Monomethyläther | |
| DE2519990C3 (de) | Verfahren zur Herstellung von Humulonen | |
| DE69208341T2 (de) | Verfahren zur Darstellung von Arylestern durch O-Dealkylierung und Anwendungen | |
| DE69220226T2 (de) | Verfahren zur herstellung von 2-alkyl-4-acyl-6-tert-butylphenol-verbindungen | |
| EP0148408B1 (de) | Verfahren zur Herstellung von 2-Isopropyl-4-methyl-6-hydroxy-pyrimidin | |
| DE1768976C3 (de) | Verfahren zur Herstellung von Bromnitroalkoholen | |
| EP0034837A1 (de) | P-tert.-Butylbenzalbromid und dessen am Kern durch Halogen substituierte Derivate | |
| WO2004026812A2 (de) | Verfahren zur katalysator-freien herstellung von cyanophenolen aus methoxybenzonitrilen | |
| EP0012108B1 (de) | Verfahren zur Herstellung von 4,5-Dichlor-2-(4-chlorphenoxy)-phenol und 4,5-Dichlor-2-(4-chlorphenoxy)-anisol | |
| DE805757C (de) | Verfahren zur Herstellung von Acetylaethylenoxyd und Diacetyl | |
| DE2145308C3 (de) | Verfahren zur Herstellung von 4-(4-Hydroxyphenyl)-butan-2-on | |
| DE19744362A1 (de) | Verfahren zur Herstellung von 4,6-Diaminoresorcinen | |
| DE2619321C2 (de) | Oxalsäurederivate, ihre Herstellung und ihre Verwendung | |
| EP0523619A2 (de) | Verfahren zur Herstellung von N-Cyanimidocarbonaten | |
| AT226677B (de) | Verfahren zur Herstellung von Bromderivaten organischer Verbindungen mit mindestens 2 nicht-kondensierten Benzolkernen, insbesondere des Diphenyls, des Diphenyläthers oder deren Homologe, die 4 und mehr Bromatome im Molekül enthalten | |
| EP0083010A1 (de) | Diether von m- oder p-Hydroxyphenolen und Verfahren zur Herstellung der Diether oder Monoether von m- oder p-Hydroxyphenolen | |
| DE1768976B2 (de) | Verfahren zur herstellung von bromnitroalkoholen | |
| DE1543995C (de) | Verfahren zur Herstellung von 5 (3 see AminoalkyhdenH0,11 dihydro 5H dibenzo eckige Klammer auf a,d ecki ge Klammer zu cycloheptenen | |
| AT226220B (de) | Verfahren zur Herstellung von Phenyläthanolaminderivaten | |
| DE1670302C3 (de) | Verfahren zur Herstellung von 3-HydroxychuiaIdin-4-carbonsäuren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8340 | Patent of addition ceased/non-payment of fee of main patent |