DE2201897A1 - Herstellung von o-Chlorphenolen - Google Patents
Herstellung von o-ChlorphenolenInfo
- Publication number
- DE2201897A1 DE2201897A1 DE19722201897 DE2201897A DE2201897A1 DE 2201897 A1 DE2201897 A1 DE 2201897A1 DE 19722201897 DE19722201897 DE 19722201897 DE 2201897 A DE2201897 A DE 2201897A DE 2201897 A1 DE2201897 A1 DE 2201897A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- chlorinated
- amine
- contact
- nitrogen
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 title description 9
- 239000003054 catalyst Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 29
- -1 chlorinated alicyclic Ketones Chemical class 0.000 claims description 19
- QCAHVKJGHYVLIS-UHFFFAOYSA-N 2,2,6,6-tetrachlorocyclohexan-1-one Chemical compound ClC1(Cl)CCCC(Cl)(Cl)C1=O QCAHVKJGHYVLIS-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000004202 carbamide Chemical class 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Chemical class 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 2
- 101150018711 AASS gene Proteins 0.000 claims 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 1
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 12
- 238000007033 dehydrochlorination reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 235000013877 carbamide Nutrition 0.000 description 8
- LKPFWCPZERQLFI-UHFFFAOYSA-N 2,4,6-trimethylpyridine;hydrochloride Chemical compound Cl.CC1=CC(C)=NC(C)=C1 LKPFWCPZERQLFI-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- MGXYSOXDYQJDKF-UHFFFAOYSA-N 2,2,6-trichlorocyclohexan-1-one Chemical compound ClC1CCCC(Cl)(Cl)C1=O MGXYSOXDYQJDKF-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical class OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- CCHNWURRBFGQCD-UHFFFAOYSA-N 2-chlorocyclohexan-1-one Chemical compound ClC1CCCCC1=O CCHNWURRBFGQCD-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910001570 bauxite Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- SDQGKKMITHAWSM-UHFFFAOYSA-N cyclohexanone;phenol Chemical compound OC1=CC=CC=C1.O=C1CCCCC1 SDQGKKMITHAWSM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007038 hydrochlorination reaction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-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
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
- C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
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 |
|---|---|---|---|
| US11577271A | 1971-02-16 | 1971-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2201897A1 true DE2201897A1 (de) | 1972-08-31 |
Family
ID=22363304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722201897 Pending DE2201897A1 (de) | 1971-02-16 | 1972-01-13 | Herstellung von o-Chlorphenolen |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU3758172A (enrdf_load_stackoverflow) |
| BE (1) | BE777967A (enrdf_load_stackoverflow) |
| DE (1) | DE2201897A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2125280B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1317080A (enrdf_load_stackoverflow) |
| IT (1) | IT949634B (enrdf_load_stackoverflow) |
| NL (1) | NL7200479A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL50995A (en) * | 1975-11-29 | 1979-11-30 | Fisons Ltd | Process for the preparation of 1,2,3-trihydroxybenzene and some derivatives thereof |
| FR2478076A1 (fr) * | 1980-03-17 | 1981-09-18 | Rhone Poulenc Ind | Procede de preparation de chlorophenols |
-
1971
- 1971-12-29 GB GB6045171A patent/GB1317080A/en not_active Expired
-
1972
- 1972-01-04 AU AU37581/72A patent/AU3758172A/en not_active Expired
- 1972-01-11 IT IT4765372A patent/IT949634B/it active
- 1972-01-12 NL NL7200479A patent/NL7200479A/xx unknown
- 1972-01-13 BE BE777967A patent/BE777967A/xx unknown
- 1972-01-13 DE DE19722201897 patent/DE2201897A1/de active Pending
- 1972-01-13 FR FR7201083A patent/FR2125280B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2125280B1 (enrdf_load_stackoverflow) | 1976-03-05 |
| BE777967A (fr) | 1972-07-13 |
| NL7200479A (enrdf_load_stackoverflow) | 1972-08-18 |
| GB1317080A (en) | 1973-05-16 |
| IT949634B (it) | 1973-06-11 |
| FR2125280A1 (enrdf_load_stackoverflow) | 1972-09-29 |
| AU3758172A (en) | 1973-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2940751C2 (de) | Verfahren zur Gewinnung von Carbonylierungsprodukten von Methylacetat | |
| DE3888523T2 (de) | Verfahren zur herstellung von 4,4'-dibromdiphenylether. | |
| EP0083442B1 (de) | Verfahren zur Herstellung von 2,4,6-Trichloranilin | |
| DE2624891C2 (de) | Verfahren zur Herstellung von Benzoylcyanid | |
| DE1470143A1 (de) | Verfahren zur Herstellung von 2-Chlorpyridin | |
| DE1018853B (de) | Verfahren zur Herstellung von 1, 1, 1-Trifluor-2-brom-2-chloraethan | |
| DE2201897A1 (de) | Herstellung von o-Chlorphenolen | |
| EP0173201B1 (de) | Verfahren zur Herstellung aromatischer Bromverbindungen | |
| EP0165540B1 (de) | Verfahren zur Herstellung von 2-Chlorpropionsäure | |
| EP0220135A2 (de) | Verfahren zur Herstellung von Chloranil | |
| DE2201899A1 (de) | Verfahren zur Herstellung von 2,2,6-Trichlorcyclohexanon und -Masse | |
| DE2841664B2 (de) | Verfahren zur Herstellung von Phenoxybenzylbromid bzw. Phenoxybenzalbromid | |
| EP0002217B1 (de) | Verfahren zur Herstellung von Tetrachlorpyrimidin | |
| DE1277840B (de) | Verfahren zur Herstellung von 2, 6-Dichlor-benzoesaeure und bzw. oder deren Anhydrid | |
| DE69908131T2 (de) | Verfahren zur Herstellung von fluoroaromatischen Verbindungen | |
| DE2264932C3 (de) | Verfahren zur Herstellung von 1,4-Dicyanbutenen | |
| DE2161995C3 (de) | Verfahren zur Herstellung von Benzotrifluorid oder dessen Derivaten | |
| DE1470143B (de) | Verfahren zur Herstellung von 2 Chlor pyndin | |
| DE2240663A1 (de) | Verfahren zur herstellung alphachloracrylsaeure | |
| DE1470143C (de) | Verfahren zur Herstellung von 2 Chlor pyndin | |
| DE1543317C3 (de) | Verfahren zur Herstellung von Aminen | |
| DE69609849T2 (de) | Verfahren zur herstellung von azomethinen und alpha-haloacetaniliden | |
| DE2332081A1 (de) | Verfahren zur herstellung von indan-1carbonsaeurederivaten | |
| DE2036174A1 (en) | Perchloro-vinylaromatics prodn - by two -stage chlorination of methyl-alkylaromatics | |
| CH493473A (de) | Verfahren zur Herstellung von Malonsäuredinitril |