JPS6029364B2 - アルキルベンゼンの直接塩素化法 - Google Patents
アルキルベンゼンの直接塩素化法Info
- Publication number
- JPS6029364B2 JPS6029364B2 JP51092736A JP9273676A JPS6029364B2 JP S6029364 B2 JPS6029364 B2 JP S6029364B2 JP 51092736 A JP51092736 A JP 51092736A JP 9273676 A JP9273676 A JP 9273676A JP S6029364 B2 JPS6029364 B2 JP S6029364B2
- Authority
- JP
- Japan
- Prior art keywords
- thianthrene
- mixture
- catalyst
- general formula
- lewis acid
- 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 44
- 150000004996 alkyl benzenes Chemical class 0.000 title claims description 5
- 238000005660 chlorination reaction Methods 0.000 title description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 115
- 239000000203 mixture Substances 0.000 claims description 43
- -1 nitro, sulfonyl Chemical group 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 239000011968 lewis acid catalyst Substances 0.000 claims description 16
- 150000005029 thianthrenes Chemical class 0.000 claims description 16
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical group C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052742 iron Inorganic materials 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000003426 co-catalyst Substances 0.000 claims description 7
- JCJOKFLPNGCLSA-UHFFFAOYSA-N 2,3,7,8-tetrachlorothianthrene Chemical group S1C2=CC(Cl)=C(Cl)C=C2SC2=C1C=C(Cl)C(Cl)=C2 JCJOKFLPNGCLSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000000217 alkyl 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 150000004820 halides Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- LFWSKTFESQXHEU-UHFFFAOYSA-N 2,7-dichlorothianthrene Chemical group ClC1=CC=C2SC3=CC(Cl)=CC=C3SC2=C1 LFWSKTFESQXHEU-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen 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 38
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- NTANEBWQKLWOQD-UHFFFAOYSA-N 1-chlorothianthrene Chemical class S1C2=CC=CC=C2SC2=C1C=CC=C2Cl NTANEBWQKLWOQD-UHFFFAOYSA-N 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 5
- 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 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZXGLGOTWDHBQPE-UHFFFAOYSA-N 1,2,3,4,6,7-hexachlorothianthrene Chemical compound ClC1=C(Cl)C(Cl)=C2SC3=C(Cl)C(Cl)=CC=C3SC2=C1Cl ZXGLGOTWDHBQPE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- VVOKLCMJWJMPPT-UHFFFAOYSA-N 1,2,3,4,6,7,8,9-octachlorothianthrene Chemical compound ClC1=C(Cl)C(Cl)=C2SC3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3SC2=C1Cl VVOKLCMJWJMPPT-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 240000000038 Ziziphus mauritiana Species 0.000 description 2
- 235000006545 Ziziphus mauritiana Nutrition 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-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
- OZOUOGAKIDCCHE-UHFFFAOYSA-N 1,2,3,4,6,7,8-heptachlorothianthrene Chemical compound S1C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2SC2=C1C=C(Cl)C(Cl)=C2Cl OZOUOGAKIDCCHE-UHFFFAOYSA-N 0.000 description 1
- AHBGXHAWSHTPOM-UHFFFAOYSA-N 1,3,2$l^{4},4$l^{4}-dioxadistibetane 2,4-dioxide Chemical compound O=[Sb]O[Sb](=O)=O AHBGXHAWSHTPOM-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
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-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
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-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
- JFKLNFNFYQVVNZ-UHFFFAOYSA-N OOCI Chemical compound OOCI JFKLNFNFYQVVNZ-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910000411 antimony tetroxide Inorganic materials 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000003849 aromatic solvent Substances 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
- 125000001743 benzylic group Chemical group 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction 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
- 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal 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
- 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0218—Sulfides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0231—Halogen-containing compounds
- B01J31/0232—Halogen-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0228
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US601219 | 1975-08-01 | ||
| US05/601,219 US4031147A (en) | 1975-08-01 | 1975-08-01 | Process for directed chlorination of alkylbenzenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5219630A JPS5219630A (en) | 1977-02-15 |
| JPS6029364B2 true JPS6029364B2 (ja) | 1985-07-10 |
Family
ID=24406665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51092736A Expired JPS6029364B2 (ja) | 1975-08-01 | 1976-08-02 | アルキルベンゼンの直接塩素化法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4031147A (OSRAM) |
| JP (1) | JPS6029364B2 (OSRAM) |
| BE (1) | BE844786A (OSRAM) |
| BR (1) | BR7605039A (OSRAM) |
| CA (1) | CA1069941A (OSRAM) |
| DE (1) | DE2634338C2 (OSRAM) |
| ES (1) | ES450337A1 (OSRAM) |
| FR (1) | FR2319606A1 (OSRAM) |
| GB (1) | GB1513063A (OSRAM) |
| IL (1) | IL50144A (OSRAM) |
| IT (1) | IT1065243B (OSRAM) |
| NL (1) | NL186083C (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62190659A (ja) * | 1986-02-17 | 1987-08-20 | Japan Storage Battery Co Ltd | クラツド式極板の製造方法 |
| JPH0579863U (ja) * | 1992-03-30 | 1993-10-29 | 株式会社ユアサコーポレーション | クラッド式密閉鉛蓄電池 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069264A (en) * | 1976-10-04 | 1978-01-17 | Hooker Chemicals & Plastics Corporation | Process for directed chlorination of alkylbenzenes |
| US4190609A (en) * | 1976-10-04 | 1980-02-26 | Hooker Chemicals & Plastics Corp. | Process for the directed chlorination of xylenes |
| US4069263A (en) * | 1977-01-03 | 1978-01-17 | Hooker Chemicals & Plastics Corporation | Process for directed chlorination of alkylbenzenes |
| DE2908928A1 (de) * | 1979-03-07 | 1980-09-18 | Studiengesellschaft Kohle Mbh | Verfahren zur herstellung von organolithiumverbindungen neben lithiumhydrid |
| US4289916A (en) * | 1979-06-28 | 1981-09-15 | Ihara Chemical Industry Co., Ltd. | Process for producing p-chloroalkylbenzene |
| DE3001473A1 (de) * | 1980-01-17 | 1981-07-23 | Robert Bosch Gmbh, 7000 Stuttgart | Stelleinrichtung zur drehwinkeleinstellung |
| US4495036A (en) * | 1983-07-11 | 1985-01-22 | The Dow Chemical Company | Electrochemical chlorination process |
| DE3718060A1 (de) * | 1987-05-28 | 1988-12-08 | Bayer Ag | Verfahren zur kernchlorierung von aromatischen kohlenwasserstoffen |
| DE58901634D1 (de) * | 1988-11-05 | 1992-07-16 | 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 |
| US7012166B2 (en) | 2003-03-18 | 2006-03-14 | General Electric Company | Catalyst composition and method for chlorinating aromatic compounds |
| US7763760B2 (en) * | 2004-06-16 | 2010-07-27 | Sabic Innovative Plastics Ip B.V. | Catalyst composition and method for halogenating aromatic compounds |
| US7863209B2 (en) * | 2004-06-16 | 2011-01-04 | Sabic Innovative Plastics Ip B.V. | Methods for recycling catalyst compositions for aromatic ring halogenation |
| US7282615B2 (en) * | 2004-06-16 | 2007-10-16 | Sabic Innovative Plastics, Ip Bv | Catalyst compositions and their use for chlorinating aromatic compounds |
| 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 (8)
| 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 |
| GB1116353A (en) * | 1964-09-02 | 1968-06-06 | Hooker Chemical Corp | Chlorination of toluene |
| DE1593589A1 (de) * | 1965-09-03 | 1970-10-22 | Tenneco Chem | Verfahren zur Herstellung von Chlortoluolen |
| DE1593590A1 (de) * | 1965-09-03 | 1970-08-13 | Tenneco Chem | Verfahren zur Herstellung von Chlortoluolen |
| US3920757A (en) * | 1971-08-25 | 1975-11-18 | Dow Chemical Co | Chlorination with sulfuryl chloride |
| IT1022654B (it) * | 1973-10-17 | 1978-04-20 | Hooker Chemicals Plastics Corp | Catalizzatori di orientamento di isomere per la alogenazione di idrocarburi aromatici |
-
1975
- 1975-08-01 US US05/601,219 patent/US4031147A/en not_active Expired - Lifetime
-
1976
- 1976-07-27 IL IL50144A patent/IL50144A/xx unknown
- 1976-07-28 CA CA257,976A patent/CA1069941A/en not_active Expired
- 1976-07-30 BE BE169478A patent/BE844786A/xx not_active IP Right Cessation
- 1976-07-30 DE DE2634338A patent/DE2634338C2/de not_active Expired
- 1976-07-30 FR FR7623342A patent/FR2319606A1/fr active Granted
- 1976-07-30 GB GB31981/76A patent/GB1513063A/en not_active Expired
- 1976-07-30 ES ES450337A patent/ES450337A1/es not_active Expired
- 1976-08-02 BR BR7605039A patent/BR7605039A/pt unknown
- 1976-08-02 JP JP51092736A patent/JPS6029364B2/ja not_active Expired
- 1976-08-02 IT IT25937/76A patent/IT1065243B/it active
- 1976-08-02 NL NLAANVRAGE7608602,A patent/NL186083C/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62190659A (ja) * | 1986-02-17 | 1987-08-20 | Japan Storage Battery Co Ltd | クラツド式極板の製造方法 |
| JPH0579863U (ja) * | 1992-03-30 | 1993-10-29 | 株式会社ユアサコーポレーション | クラッド式密閉鉛蓄電池 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL186083B (nl) | 1990-04-17 |
| JPS5219630A (en) | 1977-02-15 |
| NL186083C (nl) | 1990-09-17 |
| IL50144A (en) | 1980-01-31 |
| BR7605039A (pt) | 1977-08-09 |
| US4031147A (en) | 1977-06-21 |
| IT1065243B (it) | 1985-02-25 |
| ES450337A1 (es) | 1977-11-16 |
| FR2319606A1 (fr) | 1977-02-25 |
| BE844786A (fr) | 1977-01-31 |
| DE2634338A1 (de) | 1977-02-17 |
| DE2634338C2 (de) | 1987-04-30 |
| IL50144A0 (en) | 1976-09-30 |
| CA1069941A (en) | 1980-01-15 |
| NL7608602A (nl) | 1977-02-03 |
| FR2319606B1 (OSRAM) | 1980-12-26 |
| GB1513063A (en) | 1978-06-07 |
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