GB1163236A - Process for preparing Halogenated Aromatic Compounds - Google Patents
Process for preparing Halogenated Aromatic CompoundsInfo
- Publication number
- GB1163236A GB1163236A GB5680467A GB5680467A GB1163236A GB 1163236 A GB1163236 A GB 1163236A GB 5680467 A GB5680467 A GB 5680467A GB 5680467 A GB5680467 A GB 5680467A GB 1163236 A GB1163236 A GB 1163236A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- nitrate
- chloride
- acid
- iron
- 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
- 150000001491 aromatic compounds Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 229910002651 NO3 Inorganic materials 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052742 iron Inorganic materials 0.000 abstract 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 abstract 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000002736 metal compounds Chemical class 0.000 abstract 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 abstract 2
- -1 nitrate ions Chemical class 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 abstract 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 abstract 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 abstract 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 abstract 1
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 abstract 1
- GLJFYGFBITUZOE-UHFFFAOYSA-N 4-phenylbutylbenzene Chemical compound C=1C=CC=CC=1CCCCC1=CC=CC=C1 GLJFYGFBITUZOE-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N alpha-methyl-naphthalene Natural products C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229960002903 benzyl benzoate Drugs 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 229940006460 bromide ion Drugs 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- QXZANYPVYZTYBN-UHFFFAOYSA-N heptan-3-ylbenzene Chemical compound CCCCC(CC)C1=CC=CC=C1 QXZANYPVYZTYBN-UHFFFAOYSA-N 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 229940075566 naphthalene Drugs 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 abstract 1
- 229940049953 phenylacetate Drugs 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 1
- 235000010344 sodium nitrate Nutrition 0.000 abstract 1
- 239000004317 sodium nitrate Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,163,236. Halogenated aromatic compounds. GULF RESEARCH & DEVELOPMENT CO. 14 Dec., 1967 [19 Dec., 1966 (2)], No. 56804/66. Heading C2C. An aromatic compound, which may be an aromatic hydrocarbon, a halogenated aromatic hydrocarbon, a carboxylic acid ester of a hydroxyaromatic compound or an ester of an aromatic acid, is chlorinated or brominated in the nucleus by treatment with (a) iron or a metal of the platinum group or a compound of any of these metals, (b) a source of nitrate ions and (c) a source of chloride or bromide ions, or perchloric acid. A number of iron or platinumgroup metal compounds are specified, as also are a number of sources of chloride or bromide ions. The source of nitrate ions may be nitric acid, sodium nitrate, nitric oxide, nitrous anhydride, a nitrite, nitrous acid, nitrogen di- or tetra-oxide or nitric anhydride. A single compound, e.g. palladium nitrate or ferric chloride, may provide both the iron or platinum-group metal compound and the nitrate, chloride or bromide ion. The reaction is preferably effected at about 60-150‹ C. in a solvent and in the presence of molecular oxygen. Examples are given of the treatment of benzene, chlorobenzene, toluene, phenyl acetate, methyl benzoate and naphthalene. Reference is made also to the treatment of ethylbenzene, cumene, anthracene, biphenyl, phenanthrene, t-butylbenzene, α-phenylnaphthalene, p-xylene, terphenyl, 3-phenylheptane, 1,4-diphenylbutane, diphenylmethane and tetralin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60246966A | 1966-12-19 | 1966-12-19 | |
| US60247166A | 1966-12-19 | 1966-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1163236A true GB1163236A (en) | 1969-09-04 |
Family
ID=27084147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5680467A Expired GB1163236A (en) | 1966-12-19 | 1967-12-14 | Process for preparing Halogenated Aromatic Compounds |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE708192A (en) |
| DE (1) | DE1668163A1 (en) |
| ES (1) | ES348385A1 (en) |
| FR (1) | FR1548020A (en) |
| GB (1) | GB1163236A (en) |
| NL (1) | NL6717331A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1277726A4 (en) * | 2000-04-28 | 2005-09-14 | Nihon Nohyaku Co Ltd | PROCESS FOR THE PREPARATION OF 2-HALOBENZOIC ACIDS |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5034548B1 (en) * | 1970-02-04 | 1975-11-10 | ||
| JPS5034544B1 (en) * | 1969-06-09 | 1975-11-10 | ||
| JPS5034546B1 (en) * | 1969-11-05 | 1975-11-10 | ||
| IT1158953B (en) * | 1978-07-20 | 1987-02-25 | Snam Progetti | PROCESS FOR THE FUNCTIONALIZATION OF AROMATIC AND HETEROCYCLIC SUBSTRATES |
| DE3008158A1 (en) * | 1980-03-04 | 1981-09-10 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING 3-BROM-4-FLUORTOLUOL |
-
1967
- 1967-12-14 GB GB5680467A patent/GB1163236A/en not_active Expired
- 1967-12-18 ES ES348385A patent/ES348385A1/en not_active Expired
- 1967-12-18 DE DE19671668163 patent/DE1668163A1/en active Pending
- 1967-12-18 FR FR1548020D patent/FR1548020A/fr not_active Expired
- 1967-12-19 BE BE708192D patent/BE708192A/xx unknown
- 1967-12-19 NL NL6717331A patent/NL6717331A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1277726A4 (en) * | 2000-04-28 | 2005-09-14 | Nihon Nohyaku Co Ltd | PROCESS FOR THE PREPARATION OF 2-HALOBENZOIC ACIDS |
| US7057067B2 (en) | 2000-04-28 | 2006-06-06 | Nihon Nohyaku Co., Ltd. | Process for the preparation of 2-halobenzoic acids |
| CZ301809B6 (en) * | 2000-04-28 | 2010-06-30 | Nihon Nohyaku Co., Ltd. | Process for preparing 2-halobenzoic acids and derivatives thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1548020A (en) | 1968-11-29 |
| ES348385A1 (en) | 1969-03-01 |
| DE1668163A1 (en) | 1970-09-10 |
| BE708192A (en) | 1968-05-02 |
| NL6717331A (en) | 1968-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |