GB1576572A - Para-directed chlorination of alkylbenzenes - Google Patents
Para-directed chlorination of alkylbenzenes Download PDFInfo
- Publication number
- GB1576572A GB1576572A GB64/78A GB6478A GB1576572A GB 1576572 A GB1576572 A GB 1576572A GB 64/78 A GB64/78 A GB 64/78A GB 6478 A GB6478 A GB 6478A GB 1576572 A GB1576572 A GB 1576572A
- Authority
- GB
- United Kingdom
- Prior art keywords
- catalyst
- process according
- electron
- thianthrene
- substituent
- 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
- 150000004996 alkyl benzenes Chemical class 0.000 title claims description 26
- 238000005660 chlorination reaction Methods 0.000 title description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 101
- 238000000034 method Methods 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 239000003426 co-catalyst Substances 0.000 claims description 40
- -1 fluoro- Chemical group 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 21
- 150000005029 thianthrenes Chemical class 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000011968 lewis acid catalyst Substances 0.000 claims description 11
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 claims description 8
- RFEBONRYDWDSDE-UHFFFAOYSA-N 1,2,3,4,6,7-hexachloro-8,9-dimethylthianthrene Chemical group S1C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2SC2=C1C(C)=C(C)C(Cl)=C2Cl RFEBONRYDWDSDE-UHFFFAOYSA-N 0.000 claims description 7
- PEUWNWKLAKQNSW-UHFFFAOYSA-N 1,2,3,4,6-pentachloro-7,8-dimethylthianthrene Chemical group S1C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2SC2=C1C=C(C)C(C)=C2Cl PEUWNWKLAKQNSW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- XQDRUPXKSZQFQG-UHFFFAOYSA-N 1,2,3,4-tetrachloro-6,7-dimethylthianthrene Chemical group ClC1=C(Cl)C(Cl)=C2SC3=C(C)C(C)=CC=C3SC2=C1Cl XQDRUPXKSZQFQG-UHFFFAOYSA-N 0.000 claims description 5
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical group Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- QVIQCNNRKJQWJS-UHFFFAOYSA-N 1,2,3,4-tetrachloro-6,7,8,9-tetramethylthianthrene Chemical group ClC1=C(Cl)C(Cl)=C2SC3=C(C)C(C)=C(C)C(C)=C3SC2=C1Cl QVIQCNNRKJQWJS-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000004411 aluminium Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 66
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 17
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 16
- 229940073608 benzyl chloride Drugs 0.000 description 16
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 11
- DGHKQBYAUUIYTD-UHFFFAOYSA-N 1-chloro-2,3-dimethylthianthrene Chemical compound S1C2=CC=CC=C2SC2=C1C=C(C)C(C)=C2Cl DGHKQBYAUUIYTD-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- LQCSUVWASPTLDK-UHFFFAOYSA-N 1,2-dichloro-3,4-dimethylthianthrene Chemical compound S1C2=CC=CC=C2SC2=C1C(C)=C(C)C(Cl)=C2Cl LQCSUVWASPTLDK-UHFFFAOYSA-N 0.000 description 2
- JCJOKFLPNGCLSA-UHFFFAOYSA-N 2,3,7,8-tetrachlorothianthrene Chemical class S1C2=CC(Cl)=C(Cl)C=C2SC2=C1C=C(Cl)C(Cl)=C2 JCJOKFLPNGCLSA-UHFFFAOYSA-N 0.000 description 2
- XCBMOPWJRUGJNW-UHFFFAOYSA-N 2,3,7,8-tetramethylthianthrene Chemical compound S1C2=CC(C)=C(C)C=C2SC2=C1C=C(C)C(C)=C2 XCBMOPWJRUGJNW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- LRILBDXHOBYDGD-UHFFFAOYSA-N 1,2,3,4-tetrachlorothianthrene Chemical compound C1=CC=C2SC3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3SC2=C1 LRILBDXHOBYDGD-UHFFFAOYSA-N 0.000 description 1
- XIGHKTWDPDTMFO-UHFFFAOYSA-N 1,2,3,4-tetramethylthianthrene Chemical compound C1=CC=C2SC3=C(C)C(C)=C(C)C(C)=C3SC2=C1 XIGHKTWDPDTMFO-UHFFFAOYSA-N 0.000 description 1
- MGZAHARJQYQHJZ-UHFFFAOYSA-N 1,2,3,6,7,8-hexachloro-4,9-dimethylthianthrene Chemical compound S1C2=C(C)C(Cl)=C(Cl)C(Cl)=C2SC2=C1C(Cl)=C(Cl)C(Cl)=C2C MGZAHARJQYQHJZ-UHFFFAOYSA-N 0.000 description 1
- ZZRKWMYQNBNRMP-UHFFFAOYSA-N 1,2,3,7,8,9-hexachloro-4,6-dimethylthianthrene Chemical compound S1C2=C(Cl)C(Cl)=C(Cl)C(C)=C2SC2=C1C(Cl)=C(Cl)C(Cl)=C2C ZZRKWMYQNBNRMP-UHFFFAOYSA-N 0.000 description 1
- LALQPUXVVLATCV-UHFFFAOYSA-N 1,2,3-trichloro-4,6-dimethylthianthrene Chemical compound S1C2=C(Cl)C(Cl)=C(Cl)C(C)=C2SC2=C1C=CC=C2C LALQPUXVVLATCV-UHFFFAOYSA-N 0.000 description 1
- XWTUFPFWNHRJNF-UHFFFAOYSA-N 1,2-dimethylthianthrene Chemical compound C1=CC=C2SC3=C(C)C(C)=CC=C3SC2=C1 XWTUFPFWNHRJNF-UHFFFAOYSA-N 0.000 description 1
- OGOSITASPLPDGV-UHFFFAOYSA-N 1,4,6,9-tetrachloro-2,3,7,8-tetramethylthianthrene Chemical compound CC1=C(C)C(Cl)=C2SC3=C(Cl)C(C)=C(C)C(Cl)=C3SC2=C1Cl OGOSITASPLPDGV-UHFFFAOYSA-N 0.000 description 1
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 1
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- LEIKPMFRIYWHKW-UHFFFAOYSA-N 1-methylthianthrene Chemical class S1C2=CC=CC=C2SC2=C1C=CC=C2C LEIKPMFRIYWHKW-UHFFFAOYSA-N 0.000 description 1
- DQSMJQKRLKWXRR-UHFFFAOYSA-N 2,3,7,8-tetrachloro-1,4,6,9-tetramethylthianthrene Chemical class S1C2=C(C)C(Cl)=C(Cl)C(C)=C2SC2=C1C(C)=C(Cl)C(Cl)=C2C DQSMJQKRLKWXRR-UHFFFAOYSA-N 0.000 description 1
- 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
- ZJCZFAAXZODMQT-UHFFFAOYSA-N 2-methylpentadecane-2-thiol Chemical compound CCCCCCCCCCCCCC(C)(C)S ZJCZFAAXZODMQT-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NFMAZVUSKIJEIH-UHFFFAOYSA-N bis(sulfanylidene)iron Chemical compound S=[Fe]=S NFMAZVUSKIJEIH-UHFFFAOYSA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229940032296 ferric chloride Drugs 0.000 description 1
- 229960005191 ferric oxide Drugs 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 229960001781 ferrous sulfate Drugs 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 229910000339 iron disulfide Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229910052981 lead sulfide Inorganic materials 0.000 description 1
- 229940056932 lead sulfide Drugs 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- LIYKJALVRPGQTR-UHFFFAOYSA-M oxostibanylium;chloride Chemical compound [Cl-].[Sb+]=O LIYKJALVRPGQTR-UHFFFAOYSA-M 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- NYVGTLXTOJKHJN-UHFFFAOYSA-N thianthrene 5-oxide Chemical class C1=CC=C2S(=O)C3=CC=CC=C3SC2=C1 NYVGTLXTOJKHJN-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring 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 |
|---|---|---|---|
| US05/756,449 US4069263A (en) | 1977-01-03 | 1977-01-03 | Process for directed chlorination of alkylbenzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1576572A true GB1576572A (en) | 1980-10-08 |
Family
ID=25043537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB64/78A Expired GB1576572A (en) | 1977-01-03 | 1978-01-03 | Para-directed chlorination of alkylbenzenes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4069263A (en, 2012) |
| JP (1) | JPS5387323A (en, 2012) |
| BE (1) | BE862360A (en, 2012) |
| BR (1) | BR7708666A (en, 2012) |
| CA (1) | CA1109081A (en, 2012) |
| DE (1) | DE2800175C3 (en, 2012) |
| ES (1) | ES465738A1 (en, 2012) |
| FR (1) | FR2376104A1 (en, 2012) |
| GB (1) | GB1576572A (en, 2012) |
| IL (1) | IL53655A0 (en, 2012) |
| IT (1) | IT1143795B (en, 2012) |
| NL (1) | NL7714627A (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190609A (en) * | 1976-10-04 | 1980-02-26 | Hooker Chemicals & Plastics Corp. | Process for the directed chlorination of xylenes |
| US4289916A (en) * | 1979-06-28 | 1981-09-15 | Ihara Chemical Industry Co., Ltd. | Process for producing p-chloroalkylbenzene |
| US4250122A (en) * | 1979-09-07 | 1981-02-10 | Hooker Chemicals & Plastics Corp. | Process and catalyst mixture for the para-directed chlorination of alkylbenzenes |
| US4495036A (en) * | 1983-07-11 | 1985-01-22 | The Dow Chemical Company | Electrochemical chlorination process |
| DE3432095A1 (de) * | 1984-08-31 | 1986-03-06 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kernchlorierung von toluol |
| DE3718060A1 (de) * | 1987-05-28 | 1988-12-08 | Bayer Ag | Verfahren zur kernchlorierung von aromatischen kohlenwasserstoffen |
| DE3916664A1 (de) * | 1989-05-23 | 1991-01-03 | Bayer Ag | Verfahren zur herstellung von 2-chlor-4-nitro-alkylbenzol |
| US5621153A (en) * | 1995-04-21 | 1997-04-15 | Occidental Chemical Corporation | Process for the preparation of chloro-alkylbenzenes and novel cocatalysts therefor |
| CN104844587B (zh) * | 2015-04-29 | 2018-06-01 | 深圳市华星光电技术有限公司 | 含有吩恶噻结构的共轭化合物及其制备方法与有机电致发光二极管器件 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1741305A (en) * | 1926-02-04 | 1929-12-31 | Selden Co | Purification of aromatic hydrocarbons |
| US1946040A (en) * | 1931-10-01 | 1934-02-06 | Dow Chemical Co | Catalyst for the nuclear chlorination of benzene compounds and method of using same |
| US3226447A (en) * | 1960-12-22 | 1965-12-28 | Union Carbide Australia | Directed nuclear substitution-chlorination of aromatic hydrocarbons and halogenated aromatic hydrocarbons |
| US3920757A (en) * | 1971-08-25 | 1975-11-18 | Dow Chemical Co | Chlorination with sulfuryl chloride |
| US4031142A (en) * | 1975-08-01 | 1977-06-21 | Hooker Chemicals & Plastics Corporation | Process for the directed chlorination of alkylbenzenes |
| US4031147A (en) * | 1975-08-01 | 1977-06-21 | Hooker Chemicals & Plastics Corporation | Process for directed chlorination of alkylbenzenes |
| US4024198A (en) * | 1975-08-01 | 1977-05-17 | Hooker Chemicals & Plastics Corporation | Process for the chlorination of toluene |
| US4013147A (en) * | 1975-09-02 | 1977-03-22 | The Bendix Corporation | Segmented friction disc for brakes |
| US4013142A (en) * | 1975-10-07 | 1977-03-22 | Westinghouse Electric Corporation | Elevator system having a drive sheave with rigid but circumferentially compliant cable grooves |
| US4069264A (en) * | 1976-10-04 | 1978-01-17 | Hooker Chemicals & Plastics Corporation | Process for directed chlorination of alkylbenzenes |
-
1977
- 1977-01-03 US US05/756,449 patent/US4069263A/en not_active Expired - Lifetime
- 1977-12-20 IL IL53655A patent/IL53655A0/xx not_active IP Right Cessation
- 1977-12-23 FR FR7738986A patent/FR2376104A1/fr active Granted
- 1977-12-27 BR BR7708666A patent/BR7708666A/pt unknown
- 1977-12-27 BE BE183879A patent/BE862360A/xx not_active IP Right Cessation
- 1977-12-28 JP JP16097577A patent/JPS5387323A/ja active Granted
- 1977-12-29 IT IT31390/77A patent/IT1143795B/it active
- 1977-12-31 NL NL7714627A patent/NL7714627A/xx not_active Application Discontinuation
-
1978
- 1978-01-03 DE DE2800175A patent/DE2800175C3/de not_active Expired
- 1978-01-03 ES ES465738A patent/ES465738A1/es not_active Expired
- 1978-01-03 CA CA294,264A patent/CA1109081A/en not_active Expired
- 1978-01-03 GB GB64/78A patent/GB1576572A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1109081A (en) | 1981-09-15 |
| ES465738A1 (es) | 1979-05-01 |
| BE862360A (fr) | 1978-06-27 |
| JPS6236014B2 (en, 2012) | 1987-08-05 |
| IT1143795B (it) | 1986-10-22 |
| DE2800175A1 (de) | 1978-07-20 |
| FR2376104B1 (en, 2012) | 1984-01-20 |
| NL7714627A (nl) | 1978-07-05 |
| DE2800175C3 (de) | 1981-12-17 |
| IL53655A0 (en) | 1978-03-10 |
| JPS5387323A (en) | 1978-08-01 |
| US4069263A (en) | 1978-01-17 |
| DE2800175B2 (de) | 1980-07-24 |
| BR7708666A (pt) | 1978-08-29 |
| FR2376104A1 (fr) | 1978-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950103 |