CA1160646A - Process for the selective aliphatic chlorination of alkylbenzenes - Google Patents
Process for the selective aliphatic chlorination of alkylbenzenesInfo
- Publication number
- CA1160646A CA1160646A CA000396906A CA396906A CA1160646A CA 1160646 A CA1160646 A CA 1160646A CA 000396906 A CA000396906 A CA 000396906A CA 396906 A CA396906 A CA 396906A CA 1160646 A CA1160646 A CA 1160646A
- Authority
- CA
- Canada
- Prior art keywords
- chlorine
- cumene
- dichlorocumene
- chlorination
- cumene derivative
- 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 26
- 230000008569 process Effects 0.000 title claims description 20
- 238000005660 chlorination reaction Methods 0.000 title abstract description 14
- 125000001931 aliphatic group Chemical group 0.000 title description 2
- 150000004996 alkyl benzenes Chemical class 0.000 title description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001908 cumenes Chemical class 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- FZALJWFYGLWQEO-UHFFFAOYSA-N 1,3-dichloro-5-propan-2-ylbenzene Chemical group CC(C)C1=CC(Cl)=CC(Cl)=C1 FZALJWFYGLWQEO-UHFFFAOYSA-N 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000003849 aromatic solvent Substances 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 239000002904 solvent Substances 0.000 abstract description 11
- 125000002592 cumenyl group Chemical class C1(=C(C=CC=C1)*)C(C)C 0.000 abstract 2
- 239000000047 product Substances 0.000 description 9
- 150000002978 peroxides Chemical class 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 239000012320 chlorinating reagent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000126 substance Substances 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US248,599 | 1981-03-27 | ||
| US06/248,599 US4348265A (en) | 1981-03-27 | 1981-03-27 | Process for the selective aliphatic chlorination of alkylbenzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1160646A true CA1160646A (en) | 1984-01-17 |
Family
ID=22939809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000396906A Expired CA1160646A (en) | 1981-03-27 | 1982-02-23 | Process for the selective aliphatic chlorination of alkylbenzenes |
Country Status (6)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1225650B (it) * | 1980-07-15 | 1990-11-22 | Anic Spa | Processo per la polialogenazione, in catene laterali, di idrocarburi polialchilaromatici |
| AT382865B (de) * | 1982-06-03 | 1987-04-27 | Givaudan & Cie Sa | Verfahren zur herstellung von p-tert. butyl-benzylchlorid bzw. -benzaldehyd |
| DE3431697A1 (de) * | 1984-08-29 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3,5-dichlor-(alpha)-methylstyrol |
| FR2700714A1 (fr) | 1993-01-28 | 1994-07-29 | Atochem Elf Sa | Nouveaux réacteurs photochimiques et procédés les utilisant notamment procédé d'halogénation d'alkylbenzènes. |
| IT1263960B (it) * | 1993-02-24 | 1996-09-05 | Enichem Sintesi | Procedimento per la fotoclorurazione di composti alchilaromatici |
| CN104529789B (zh) * | 2014-12-04 | 2017-02-22 | 苏州市玮琪生物科技有限公司 | 3,5‑二氯‑α，α‑二甲基苄胺合成工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2193823A (en) * | 1937-04-09 | 1940-03-19 | Du Pont | Chlorinated aromatic hydrocarbons |
| US3251887A (en) * | 1961-07-19 | 1966-05-17 | Dow Chemical Co | Chlorination process |
| US4087473A (en) * | 1976-11-03 | 1978-05-02 | The Dow Chemical Company | Preferential aliphatic halogenation of ar-substituted alkylbenzenes |
| US4226783A (en) * | 1978-07-03 | 1980-10-07 | E. I. Du Pont De Nemours And Company | α-Chlorination process |
| DE2905081A1 (de) * | 1979-02-10 | 1980-08-14 | Bayer Ag | Verfahren zur herstellung von in alpha-stellung monohalogenierten alkylbenzolen und neue in alpha-stellung monohalogenierte alkylbenzole |
-
1981
- 1981-03-27 US US06/248,599 patent/US4348265A/en not_active Expired - Lifetime
-
1982
- 1982-02-23 CA CA000396906A patent/CA1160646A/en not_active Expired
- 1982-03-24 EP EP82102472A patent/EP0061720B1/en not_active Expired
- 1982-03-24 DE DE8282102472T patent/DE3262515D1/de not_active Expired
- 1982-03-24 BR BR8201694A patent/BR8201694A/pt unknown
- 1982-03-27 JP JP57049940A patent/JPS57175134A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0145456B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-10-03 |
| US4348265A (en) | 1982-09-07 |
| EP0061720B1 (en) | 1985-03-13 |
| BR8201694A (pt) | 1983-02-16 |
| EP0061720A1 (en) | 1982-10-06 |
| DE3262515D1 (en) | 1985-04-18 |
| JPS57175134A (en) | 1982-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |