CH648276A5 - Process for the preparation of benzene derivatives - Google Patents
Process for the preparation of benzene derivatives Download PDFInfo
- Publication number
- CH648276A5 CH648276A5 CH3397/82A CH339782A CH648276A5 CH 648276 A5 CH648276 A5 CH 648276A5 CH 3397/82 A CH3397/82 A CH 3397/82A CH 339782 A CH339782 A CH 339782A CH 648276 A5 CH648276 A5 CH 648276A5
- Authority
- CH
- Switzerland
- Prior art keywords
- tert
- reaction
- butyl
- chlorine
- butyltoluene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000460 chlorine Substances 0.000 claims abstract description 21
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 21
- 150000003254 radicals Chemical class 0.000 claims abstract description 13
- 230000005855 radiation Effects 0.000 claims abstract description 9
- QCWXDVFBZVHKLV-UHFFFAOYSA-N 1-tert-butyl-4-methylbenzene Chemical compound CC1=CC=C(C(C)(C)C)C=C1 QCWXDVFBZVHKLV-UHFFFAOYSA-N 0.000 claims abstract description 5
- WAXIFMGAKWIFDQ-UHFFFAOYSA-N 1-tert-butyl-4-(chloromethyl)benzene Chemical compound CC(C)(C)C1=CC=C(CCl)C=C1 WAXIFMGAKWIFDQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 claims description 14
- OSOLHARQJQEMBZ-UHFFFAOYSA-N 1-chloropentylbenzene Chemical compound CCCCC(Cl)C1=CC=CC=C1 OSOLHARQJQEMBZ-UHFFFAOYSA-N 0.000 claims description 12
- ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 claims description 12
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 6
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- SNLOCRBUBDQVOC-UHFFFAOYSA-N (1,1-dichloro-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(Cl)(Cl)CC1=CC=CC=C1 SNLOCRBUBDQVOC-UHFFFAOYSA-N 0.000 claims description 2
- UZTQWZWUTLLANF-UHFFFAOYSA-N 1-tert-butyl-4-(dichloromethyl)benzene Chemical compound CC(C)(C)C1=CC=C(C(Cl)Cl)C=C1 UZTQWZWUTLLANF-UHFFFAOYSA-N 0.000 claims description 2
- 238000006007 Sommelet synthesis reaction Methods 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical class CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000006735 deficit Effects 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000004817 gas chromatography Methods 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 150000003613 toluenes Chemical class 0.000 claims description 2
- 230000007306 turnover Effects 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003999 initiator Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical class CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Classifications
-
- 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
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
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 |
|---|---|---|---|
| CH3397/82A CH648276A5 (en) | 1982-06-03 | 1982-06-03 | Process for the preparation of benzene derivatives |
| IT8321291A IT1169421B (it) | 1982-06-03 | 1983-05-25 | Procedimento per la preparazione di benzen-derivati |
| US06/497,611 US4853489A (en) | 1982-06-03 | 1983-05-28 | Selective chlorination of para-tertiary-butytoluene |
| NL8301932A NL8301932A (nl) | 1982-06-03 | 1983-05-31 | Werkwijze voor het bereiden van benzeenderivaten. |
| AT200883A AT382865B (de) | 1982-06-03 | 1983-06-01 | Verfahren zur herstellung von p-tert. butyl-benzylchlorid bzw. -benzaldehyd |
| FR8309069A FR2528034B1 (fr) | 1982-06-03 | 1983-06-01 | Procede de preparation de derives de p-tert-butylbenzene |
| GB08315206A GB2125396B (en) | 1982-06-03 | 1983-06-02 | Process for the manufacture of p-t-butyl-benzyl chloride |
| JP9872983A JPS5980624A (ja) | 1982-06-03 | 1983-06-02 | ベンゼン誘導体の製造方法 |
| BE0/210910A BE896932A (fr) | 1982-06-03 | 1983-06-02 | Procede pour la preparation de derives de benzene |
| DE19833320020 DE3320020A1 (de) | 1982-06-03 | 1983-06-03 | Verfahren zur herstellung von benzolderivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3397/82A CH648276A5 (en) | 1982-06-03 | 1982-06-03 | Process for the preparation of benzene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH648276A5 true CH648276A5 (en) | 1985-03-15 |
Family
ID=4255096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3397/82A CH648276A5 (en) | 1982-06-03 | 1982-06-03 | Process for the preparation of benzene derivatives |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5980624A (enrdf_load_stackoverflow) |
| BE (1) | BE896932A (enrdf_load_stackoverflow) |
| CH (1) | CH648276A5 (enrdf_load_stackoverflow) |
-
1982
- 1982-06-03 CH CH3397/82A patent/CH648276A5/de not_active IP Right Cessation
-
1983
- 1983-06-02 BE BE0/210910A patent/BE896932A/fr not_active IP Right Cessation
- 1983-06-02 JP JP9872983A patent/JPS5980624A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE896932A (fr) | 1983-12-02 |
| JPS6311340B2 (enrdf_load_stackoverflow) | 1988-03-14 |
| JPS5980624A (ja) | 1984-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |