DE2110826A1 - Verfahren zur Herstellung halogenierter Alkohole - Google Patents
Verfahren zur Herstellung halogenierter AlkoholeInfo
- Publication number
- DE2110826A1 DE2110826A1 DE19712110826 DE2110826A DE2110826A1 DE 2110826 A1 DE2110826 A1 DE 2110826A1 DE 19712110826 DE19712110826 DE 19712110826 DE 2110826 A DE2110826 A DE 2110826A DE 2110826 A1 DE2110826 A1 DE 2110826A1
- Authority
- DE
- Germany
- Prior art keywords
- lithium bromide
- alcohol
- aqueous
- bromine
- solution
- 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 62
- 150000001298 alcohols Chemical class 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 191
- 239000000243 solution Substances 0.000 claims description 52
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 40
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000012074 organic phase Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000000047 product Substances 0.000 description 28
- 239000007795 chemical reaction product Substances 0.000 description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- FHCLGDLYRUPKAM-UHFFFAOYSA-N 1,2,3-tribromopropane Chemical compound BrCC(Br)CBr FHCLGDLYRUPKAM-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- AONKGGMHQHWMSM-UHFFFAOYSA-N 1,1,1-tribromopropane Chemical compound CCC(Br)(Br)Br AONKGGMHQHWMSM-UHFFFAOYSA-N 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000012431 aqueous reaction media Substances 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001503 inorganic bromide Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- -1 triols or the like Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/075—Acyclic saturated compounds containing halogen atoms containing bromine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/38—Halogenated alcohols containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
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 |
|---|---|---|---|
| US2040470A | 1970-03-17 | 1970-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2110826A1 true DE2110826A1 (de) | 1971-10-07 |
Family
ID=21798452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712110826 Pending DE2110826A1 (de) | 1970-03-17 | 1971-03-06 | Verfahren zur Herstellung halogenierter Alkohole |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3681468A (enExample) |
| BE (1) | BE763250A (enExample) |
| CS (1) | CS154320B2 (enExample) |
| DE (1) | DE2110826A1 (enExample) |
| FR (1) | FR2083957A5 (enExample) |
| GB (1) | GB1278225A (enExample) |
| IL (1) | IL36135A (enExample) |
| NL (1) | NL7102473A (enExample) |
| SU (1) | SU417931A3 (enExample) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3283013A (en) * | 1962-06-28 | 1966-11-01 | Du Pont | Process for the preparation of 2, 3-dibromo-1-propanol |
| US3268597A (en) * | 1962-08-03 | 1966-08-23 | Michigan Chem Corp | Continuous preparation of 2, 3-dibromopropanol-1 compound |
| DE1230412B (de) * | 1964-12-14 | 1966-12-15 | Kalk Chemische Fabrik Gmbh | Verfahren und Vorrichtung zur Herstellung von 2, 3-Dibrompropanol |
| DE1277244B (de) * | 1965-02-25 | 1968-09-12 | Basf Ag | Verfahren zur Herstellung von 2, 3-Dibrombuten-(2)-diol-(1,4),2,2,3,3-Tetrabrombutandiol-(1,4) und/oder Mucobromsaeure |
| FR1492303A (fr) * | 1966-07-08 | 1967-08-18 | Pechiney Saint Gobain | Bromation du butyne- et du butène-diol |
-
1970
- 1970-03-17 US US20404A patent/US3681468A/en not_active Expired - Lifetime
-
1971
- 1971-02-04 IL IL36135A patent/IL36135A/xx unknown
- 1971-02-22 BE BE763250A patent/BE763250A/xx unknown
- 1971-02-24 NL NL7102473A patent/NL7102473A/xx unknown
- 1971-02-25 FR FR7106457A patent/FR2083957A5/fr not_active Expired
- 1971-03-04 CS CS162071A patent/CS154320B2/cs unknown
- 1971-03-06 DE DE19712110826 patent/DE2110826A1/de active Pending
- 1971-03-16 SU SU1632795A patent/SU417931A3/ru active
- 1971-04-19 GB GB21139/71A patent/GB1278225A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2083957A5 (enExample) | 1971-12-17 |
| SU417931A3 (ru) | 1974-02-28 |
| CS154320B2 (enExample) | 1974-03-29 |
| US3681468A (en) | 1972-08-01 |
| IL36135A0 (en) | 1971-04-28 |
| IL36135A (en) | 1974-05-16 |
| GB1278225A (en) | 1972-06-21 |
| NL7102473A (enExample) | 1971-09-21 |
| BE763250A (fr) | 1971-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |