JPH0476987B2 - - Google Patents

Info

Publication number: JPH0476987B2
Authority: JP; Japan
Prior art keywords: reaction; acid; catalyst; group; benzenes
Prior art date: 1986-07-16
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 - Lifetime

Application number

JP61168579A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6323854A (ja

Inventor

Hiroshi Masami

Mikiro Nakazawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SHIN NIPPON RIKA KK

Original Assignee

SHIN NIPPON RIKA KK

Priority date (The priority date 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 date listed.)

1986-07-16

Filing date

1986-07-16

Publication date

1992-12-07

1986-07-16 Application filed by SHIN NIPPON RIKA KK filed Critical SHIN NIPPON RIKA KK

1986-07-16 Priority to JP61168579A priority Critical patent/JPS6323854A/ja

1987-07-07 Priority to US07/070,576 priority patent/US4778932A/en

1987-07-15 Priority to DE3723401A priority patent/DE3723401C2/de

1988-02-01 Publication of JPS6323854A publication Critical patent/JPS6323854A/ja

1992-12-07 Publication of JPH0476987B2 publication Critical patent/JPH0476987B2/ja

Status Granted legal-status Critical Current

Links

QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
239000003054 catalyst Substances 0.000 claims description 23
150000001555 benzenes Chemical class 0.000 claims description 20
-1 phenoxy, substituted phenoxy Chemical group 0.000 claims description 13
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 claims description 9
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001033 ether group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
239000011964 heteropoly acid Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
230000000052 comparative effect Effects 0.000 description 5
229940078552 o-xylene Drugs 0.000 description 5
BCTWNMTZAXVEJL-UHFFFAOYSA-N phosphane;tungsten;tetracontahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] BCTWNMTZAXVEJL-UHFFFAOYSA-N 0.000 description 5
KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
ZSIACQWHDVUCHB-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)sulfonyl-1,2-dimethylbenzene Chemical compound C1=C(C)C(C)=CC=C1S(=O)(=O)C1=CC=C(C)C(C)=C1 ZSIACQWHDVUCHB-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012024 dehydrating agents‎ Substances 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000002994 raw material Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
229910052710 silicon Inorganic materials 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
WEAYCYAIVOIUMG-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)sulfonylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC=C(C)C=C1 WEAYCYAIVOIUMG-UHFFFAOYSA-N 0.000 description 2
GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 2
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
238000007865 diluting Methods 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229910052733 gallium Inorganic materials 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
MMYVDBHFYSHDSL-UHFFFAOYSA-N 1,2-dichloro-4-(3,4-dichlorophenyl)sulfonylbenzene Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 MMYVDBHFYSHDSL-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 description 1
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
229910001149 41xx steel Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
229910003294 NiMo Inorganic materials 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001168730 Simo Species 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
229920006015 heat resistant resin Polymers 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
CEFSVYOPCJUCQP-UHFFFAOYSA-N methyl sulfo sulfate Chemical compound COS(=O)(=O)OS(O)(=O)=O CEFSVYOPCJUCQP-UHFFFAOYSA-N 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
229920002492 poly(sulfone) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1

Classifications

- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP61168579A 1986-07-16 1986-07-16 ジアリ−ルスルホン類の製造方法 Granted JPS6323854A (ja)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
JP61168579A JPS6323854A (ja)	1986-07-16	1986-07-16	ジアリ−ルスルホン類の製造方法
US07/070,576 US4778932A (en)	1986-07-16	1987-07-07	Process for preparing diarylsulfones
DE3723401A DE3723401C2 (de)	1986-07-16	1987-07-15	Verfahren zur Herstellung von Diarylsulfonen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP61168579A JPS6323854A (ja)	1986-07-16	1986-07-16	ジアリ−ルスルホン類の製造方法

Publications (2)

Publication Number	Publication Date
JPS6323854A JPS6323854A (ja)	1988-02-01
JPH0476987B2 true JPH0476987B2 (no)	1992-12-07

Family

ID=15870667

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61168579A Granted JPS6323854A (ja)	1986-07-16	1986-07-16	ジアリ−ルスルホン類の製造方法

Country Status (1)

Country	Link
JP (1)	JPS6323854A (no)

1986
- 1986-07-16 JP JP61168579A patent/JPS6323854A/ja active Granted

Also Published As

Publication number	Publication date
JPS6323854A (ja)	1988-02-01

Legal Events

Date	Code	Title	Description
2004-11-02	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2005-12-07	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
JP2004531492A (ja)	2004-10-14	金属ビストリフルイミド化合物及び金属ビストリフルイミド化合物の合成方法
JPS58189038A (ja)	1983-11-04	特にメタクロレインの気相酸化によるメタクリル酸製造用の酸化触媒
US4778932A (en)	1988-10-18	Process for preparing diarylsulfones
EP0078247B1 (en)	1985-11-27	Process and catalysts for vapor phase nitration of aromatic compounds
US4347389A (en)	1982-08-31	Vapor phase nitration of aromatic compounds
US4361709A (en)	1982-11-30	Process for the production of o-alkylated phenols
EP0013578B2 (en)	1984-06-06	Process for producing methacrylic acid
JPH0476987B2 (no)	1992-12-07
JPH11169716A (ja)	1999-06-29	不飽和ニトリルおよび／または不飽和カルボン酸を製造するための触媒
JP4294209B2 (ja)	2009-07-08	オルト位アルキル化ヒドロキシ芳香族化合物の製造方法
JPH0428259B2 (no)	1992-05-13
JPH1017542A (ja)	1998-01-20	ジアリールスルホン類の製造方法
EP1386907B1 (en)	2011-10-05	Process for vapor phase nitration of benzene using nitric acid over molybdenum silica catalyst
JP2977334B2 (ja)	1999-11-15	ポリアルキルベンゼンの製造方法及び触媒
JPH0253100B2 (no)	1990-11-15
JP2977333B2 (ja)	1999-11-15	アルキルベンゼンの製造方法及び触媒
JPH03118337A (ja)	1991-05-20	１，１―ジアリールエタンの製造方法
PL167274B1 (pl)	1995-08-31	Sposób wytwarzania 2 ,2 -bis-/3 ,4-dimetylo-fenylo/-propanu PL
JPH0460595B2 (no)	1992-09-28
JPH047734B2 (no)	1992-02-12
JP3521970B2 (ja)	2004-04-26	グリコール酸の製造方法
JPS6332771B2 (no)	1988-07-01
JPS6092236A (ja)	1985-05-23	シクロヘキサノンの製造方法
JPS6152130B2 (no)	1986-11-12
JPS6348238A (ja)	1988-02-29	フエノ−ル類の製造方法