DE2027162C3 - Verfahren zur Brommethylierung von Benzolkohlenw asserstoffen - Google Patents
Verfahren zur Brommethylierung von Benzolkohlenw asserstoffenInfo
- Publication number
- DE2027162C3 DE2027162C3 DE2027162A DE2027162A DE2027162C3 DE 2027162 C3 DE2027162 C3 DE 2027162C3 DE 2027162 A DE2027162 A DE 2027162A DE 2027162 A DE2027162 A DE 2027162A DE 2027162 C3 DE2027162 C3 DE 2027162C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- hydrogen bromide
- carboxylic acid
- reaction
- aliphatic
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 14
- -1 benzene hydrocarbons Chemical class 0.000 title claims description 6
- 229930195733 hydrocarbon Natural products 0.000 title claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 48
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 9
- 229920002866 paraformaldehyde Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000012452 mother liquor Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 claims description 2
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 claims description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000004970 halomethyl group Chemical group 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DLIMCTYULDURCT-UHFFFAOYSA-N 1,2-bis(bromomethyl)-3,4-dimethylbenzene Chemical compound CC1=CC=C(CBr)C(CBr)=C1C DLIMCTYULDURCT-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- BHIFXIATEXVOQA-UHFFFAOYSA-N 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene Chemical compound CC1=C(CBr)C(C)=C(CBr)C(C)=C1CBr BHIFXIATEXVOQA-UHFFFAOYSA-N 0.000 description 1
- OREPDRBSWICSCF-UHFFFAOYSA-N 1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene Chemical compound CC1=C(C)C(CBr)=C(C)C(C)=C1CBr OREPDRBSWICSCF-UHFFFAOYSA-N 0.000 description 1
- CHMJJIHXWABUHA-UHFFFAOYSA-N 1-(chloromethyl)-2,3-dimethylbenzene Chemical compound CC1=CC=CC(CCl)=C1C CHMJJIHXWABUHA-UHFFFAOYSA-N 0.000 description 1
- OJXMOPVOQHEPLD-UHFFFAOYSA-N 2,5-bis(bromomethyl)-1,3-dimethylbenzene Chemical compound CC1=CC(CBr)=CC(C)=C1CBr OJXMOPVOQHEPLD-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 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
- 239000007789 gas Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000005172 methylbenzenes Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2027162A DE2027162C3 (de) | 1970-06-03 | 1970-06-03 | Verfahren zur Brommethylierung von Benzolkohlenw asserstoffen |
| FR7114818A FR2093994B1 (enExample) | 1970-06-03 | 1971-04-26 | |
| US00141410A US3833666A (en) | 1970-06-03 | 1971-05-07 | Process for bromomethylating aromatic hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2027162A DE2027162C3 (de) | 1970-06-03 | 1970-06-03 | Verfahren zur Brommethylierung von Benzolkohlenw asserstoffen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2027162A1 DE2027162A1 (de) | 1971-12-09 |
| DE2027162B2 DE2027162B2 (de) | 1973-05-30 |
| DE2027162C3 true DE2027162C3 (de) | 1974-05-22 |
Family
ID=5772870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2027162A Expired DE2027162C3 (de) | 1970-06-03 | 1970-06-03 | Verfahren zur Brommethylierung von Benzolkohlenw asserstoffen |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3833666A (enExample) |
| DE (1) | DE2027162C3 (enExample) |
| FR (1) | FR2093994B1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3214416C2 (de) * | 1982-04-20 | 1984-03-15 | Chemische Fabrik Kalk GmbH, 5000 Köln | Tetrakis-(brommethyl)-diphenyläther, Verfahren zu seiner Herstellung und seine Verwendung als Brandschutzmittel |
| DE3334068A1 (de) * | 1983-09-21 | 1985-04-11 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur brommethylierung von polyphenylenethern |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2212099A (en) * | 1938-04-25 | 1940-08-20 | American Chem Paint Co | Art of preparing methyl halide derivatives of aromatic hydrocarbons |
-
1970
- 1970-06-03 DE DE2027162A patent/DE2027162C3/de not_active Expired
-
1971
- 1971-04-26 FR FR7114818A patent/FR2093994B1/fr not_active Expired
- 1971-05-07 US US00141410A patent/US3833666A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3833666A (en) | 1974-09-03 |
| DE2027162B2 (de) | 1973-05-30 |
| DE2027162A1 (de) | 1971-12-09 |
| FR2093994B1 (enExample) | 1973-10-19 |
| FR2093994A1 (enExample) | 1972-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8320 | Willingness to grant licences declared (paragraph 23) | ||
| 8330 | Complete disclaimer |