DE2604276C2 - Verfahren zur α-Monochlorierung kernchlorierter Toluole - Google Patents
Verfahren zur α-Monochlorierung kernchlorierter ToluoleInfo
- Publication number
- DE2604276C2 DE2604276C2 DE2604276A DE2604276A DE2604276C2 DE 2604276 C2 DE2604276 C2 DE 2604276C2 DE 2604276 A DE2604276 A DE 2604276A DE 2604276 A DE2604276 A DE 2604276A DE 2604276 C2 DE2604276 C2 DE 2604276C2
- Authority
- DE
- Germany
- Prior art keywords
- chlorinated
- para
- chlorine
- reaction
- nuclear
- 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
- 238000000034 method Methods 0.000 title claims description 25
- 150000003613 toluenes Chemical class 0.000 title claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 7
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 6
- MJEPOVIWHVRBIT-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=C(Cl)C=C1 MJEPOVIWHVRBIT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000005660 chlorination reaction Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 6
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- LOXRGHGHQYWXJK-UHFFFAOYSA-N 1-octylsulfanyloctane Chemical compound CCCCCCCCSCCCCCCCC LOXRGHGHQYWXJK-UHFFFAOYSA-N 0.000 description 2
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Polymers 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- JJMLCWKZDOCOPH-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenyl)sulfanylbenzene Chemical compound ClC1=CC=CC=C1SC1=CC=CC=C1Cl JJMLCWKZDOCOPH-UHFFFAOYSA-N 0.000 description 1
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
- WZXXZHONLFRKGG-UHFFFAOYSA-N 2,3,4,5-tetrachlorothiophene Chemical compound ClC=1SC(Cl)=C(Cl)C=1Cl WZXXZHONLFRKGG-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl chloro aromatic compounds Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54707975A | 1975-02-04 | 1975-02-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2604276A1 DE2604276A1 (de) | 1976-08-05 |
| DE2604276C2 true DE2604276C2 (de) | 1984-09-06 |
Family
ID=24183274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2604276A Expired DE2604276C2 (de) | 1975-02-04 | 1976-02-04 | Verfahren zur α-Monochlorierung kernchlorierter Toluole |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4092369A (enExample) |
| JP (1) | JPS6026771B2 (enExample) |
| BE (1) | BE838200A (enExample) |
| BR (1) | BR7600530A (enExample) |
| CA (1) | CA1068728A (enExample) |
| CH (1) | CH602526A5 (enExample) |
| DE (1) | DE2604276C2 (enExample) |
| FR (1) | FR2300060A1 (enExample) |
| GB (1) | GB1473289A (enExample) |
| IT (1) | IT1054829B (enExample) |
| NL (1) | NL186904C (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087473A (en) * | 1976-11-03 | 1978-05-02 | The Dow Chemical Company | Preferential aliphatic halogenation of ar-substituted alkylbenzenes |
| DE2961828D1 (en) * | 1978-10-11 | 1982-02-25 | Bayer Ag | Process for the monohalogenation of alkylbenzenes in alpha position |
| US4399075A (en) * | 1981-06-25 | 1983-08-16 | Asahi Chemical Company, Limited | Process for producing chlorinated phenoxytoluene derivatives |
| CA1288780C (en) * | 1985-12-27 | 1991-09-10 | Takanori Miyake | Process for producing halogenated benzene derivative using zeolite catalyst |
| CN113105302B (zh) * | 2021-03-04 | 2024-01-12 | 老河口华辰化学有限公司 | 一种邻氯甲苯氯化联产邻氯氯苄、邻氯二氯苄和邻氯三氯苄的方法 |
| FR3144560B1 (fr) | 2023-01-04 | 2024-11-15 | Psa Automobiles Sa | Système d’affichage pour véhicule et véhicule comprenant un tel système d’affichage |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1345373A (en) * | 1917-07-26 | 1920-07-06 | Gen Chemical Corp | Process of producing halogenated homologues of benzene |
| US2695873A (en) * | 1952-04-04 | 1954-11-30 | Hooker Electrochemical Co | Process for chlorinating methyl aromatic compounds |
| US2926201A (en) * | 1957-06-11 | 1960-02-23 | Dow Chemical Co | Side-chain chlorination of ethylpolychlorobenzenes |
| US3338811A (en) * | 1964-09-21 | 1967-08-29 | Kaiser Aluminium Chem Corp | Photochlorination of alkyl aromatic compounds |
-
1976
- 1976-01-28 BR BR7600530A patent/BR7600530A/pt unknown
- 1976-01-30 CA CA244,963A patent/CA1068728A/en not_active Expired
- 1976-02-02 CH CH1453876A patent/CH602526A5/xx not_active IP Right Cessation
- 1976-02-02 BE BE164036A patent/BE838200A/xx unknown
- 1976-02-02 NL NLAANVRAGE7601001,A patent/NL186904C/xx not_active IP Right Cessation
- 1976-02-02 FR FR7602761*[A patent/FR2300060A1/fr active Granted
- 1976-02-03 GB GB427676A patent/GB1473289A/en not_active Expired
- 1976-02-03 JP JP51011211A patent/JPS6026771B2/ja not_active Expired
- 1976-02-03 IT IT19828/76A patent/IT1054829B/it active
- 1976-02-04 DE DE2604276A patent/DE2604276C2/de not_active Expired
- 1976-07-12 US US05/704,729 patent/US4092369A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6026771B2 (ja) | 1985-06-25 |
| GB1473289A (en) | 1977-05-11 |
| NL186904C (nl) | 1991-04-02 |
| NL186904B (nl) | 1990-11-01 |
| CH602526A5 (enExample) | 1978-07-31 |
| DE2604276A1 (de) | 1976-08-05 |
| JPS51101925A (enExample) | 1976-09-08 |
| US4092369A (en) | 1978-05-30 |
| IT1054829B (it) | 1981-11-30 |
| NL7601001A (nl) | 1976-08-06 |
| CA1068728A (en) | 1979-12-25 |
| FR2300060B1 (enExample) | 1980-11-14 |
| BR7600530A (pt) | 1976-08-31 |
| FR2300060A1 (fr) | 1976-09-03 |
| BE838200A (fr) | 1976-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: OCCIDENTAL CHEMICAL CORP. (EINE GESELLSCHAFT N.D.G |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |