NL8101250A - Werkwijze voor het bereiden van resorcinol. - Google Patents

Werkwijze voor het bereiden van resorcinol. Download PDF

Info

Publication number: NL8101250A
Authority: NL; Netherlands
Prior art keywords: pentafluoride; meta; catalyst; acid; perfluoridated
Prior art date: 1980-03-14

Application number

NL8101250A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ugine Kuhlmann

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.)

1980-03-14

Filing date

1981-03-13

Publication date

1981-10-01

1981-03-13 Application filed by Ugine Kuhlmann filed Critical Ugine Kuhlmann

1981-10-01 Publication of NL8101250A publication Critical patent/NL8101250A/nl

Links

GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims description 22
238000004519 manufacturing process Methods 0.000 title claims 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 24
239000003054 catalyst Substances 0.000 claims description 19
238000000034 method Methods 0.000 claims description 15
239000003930 superacid Substances 0.000 claims description 14
UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
239000011347 resin Substances 0.000 claims description 10
229920005989 resin Polymers 0.000 claims description 10
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
-1 Lewis acid fluoride Chemical class 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
238000006317 isomerization reaction Methods 0.000 claims description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 5
229910015900 BF3 Inorganic materials 0.000 claims description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
239000002841 Lewis acid Substances 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 claims description 3
OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 claims 2
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 claims 1
229910021630 Antimony pentafluoride Inorganic materials 0.000 claims 1
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
239000013256 coordination polymer Substances 0.000 claims 1
YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims 1
AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 claims 1
230000008707 rearrangement Effects 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
238000003756 stirring Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 4
238000007323 disproportionation reaction Methods 0.000 description 3
150000005172 methylbenzenes Chemical class 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000010555 transalkylation reaction Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
KKIGDGWHHNXWNM-UHFFFAOYSA-N 1,2,3-tripropylbenzene Chemical compound CCCC1=CC=CC(CCC)=C1CCC KKIGDGWHHNXWNM-UHFFFAOYSA-N 0.000 description 1
TVUGCKOJGZCBCK-UHFFFAOYSA-N 1,2-dihydroperoxybenzene Chemical compound OOC1=CC=CC=C1OO TVUGCKOJGZCBCK-UHFFFAOYSA-N 0.000 description 1
VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 description 1
SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 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
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229920002313 fluoropolymer Polymers 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
210000004124 hock Anatomy 0.000 description 1
CUPFNGOKRMWUOO-UHFFFAOYSA-N hydron;difluoride Chemical compound F.F CUPFNGOKRMWUOO-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical group CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
- C07C5/2732—Catalytic processes
- C07C5/274—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C5/2748—Acids of halogen; Salts thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
- C07C5/2732—Catalytic processes
- C07C5/274—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C5/2748—Acids of halogen; Salts thereof
- C07C5/2751—Metal halides; Complexes thereof with organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
- C07C5/2732—Catalytic processes
- C07C5/2756—Catalytic processes with hydrides or organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1206—Hydrogen fluoride
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/133—Compounds comprising a halogen and vanadium, niobium, tantalium, antimonium or bismuth
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/14—Phosphorus; Compounds thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8101250A 1980-03-14 1981-03-13 Werkwijze voor het bereiden van resorcinol. NL8101250A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13040180		1980-03-14
US06/130,401 US4339613A (en)	1980-03-14	1980-03-14	Superacid catalyzed preparation of resorcinol from meta-diisopropylbenzene

Publications (1)

Publication Number	Publication Date
NL8101250A true NL8101250A (nl)	1981-10-01

Family

ID=22444532

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8101250A NL8101250A (nl)	1980-03-14	1981-03-13	Werkwijze voor het bereiden van resorcinol.

Country Status (9)

Country	Link
US (1)	US4339613A (fr)
JP (1)	JPS56142226A (fr)
BE (1)	BE887779A (fr)
CA (1)	CA1144945A (fr)
DE (1)	DE3109339C2 (fr)
FR (1)	FR2478075A1 (fr)
GB (3)	GB2137224B (fr)
IT (1)	IT1144702B (fr)
NL (1)	NL8101250A (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1129809B (it) *	1979-03-26	1986-06-11	Ugine Kuhlmann	Composizione catalitica per la conversione di idrocarburi e procedimento per la disidratazione di acidi perfluoroalcansolfonici destinati a fare parte bella composizione
US4423254A (en) *	1980-03-14	1983-12-27	Pcuk Produits Chimiques Ugine Kuhlmann	Superacid catalyzed preparation of resorcinol from meta-isopropylphenol
FR2483403A1 (fr) *	1980-06-03	1981-12-04	Ugine Kuhlmann	Procede de meta-hydroxylation des alkyl-phenols et de leurs ethers en milieu superacide
DE3416580A1 (de) *	1983-05-06	1984-11-08	CBS Inc., New York, N.Y.	Gitarrenhals mit integriertem sattel
US4487970A (en) *	1983-06-03	1984-12-11	Phillips Petroleum Company	Cleavage of hydroperoxides
AU594348B2 (en) *	1985-06-28	1990-03-08	Mitsui Toatsu Chemicals Inc.	Process for producing 6,6'-dihydroxy-3,3,3',3'-tetramethyl- 1,1'-spirobiidane
US4847436A (en) *	1987-12-22	1989-07-11	Indspec Chemical Corporation	Decomposition of dihydroperoxide to resorcinol
US4849549A (en) *	1987-12-22	1989-07-18	Indspec Chemical Corporation	Process for preparation of resorcinol
US4847437A (en) *	1987-12-22	1989-07-11	Indspec Chemical Corporation	Oxidation and subsequent decomposition of dihydroperoxide
KR100281849B1 (ko) *	1992-11-05	2001-02-15	나까니시 히로유끼	하이드록시 방향족화합물의 제조방법
US6586640B2 (en) *	2001-06-26	2003-07-01	E. I. Du Pont De Nemours And Company	Decomposition of organic hydroperoxides in the presence of a particulate catalyst containing highly fluorinated polymer having sulfonic acid groups and process for the manufacture of bisphenol A
JP4955440B2 (ja) *	2007-03-29	2012-06-20	Ｊｘ日鉱日石エネルギー株式会社	ジヒドロキシ芳香族化合物の製造方法

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE486910A (fr) *
US2736753A (en) *	1952-09-10	1956-02-28	Hercules Powder Co Ltd	Recovery of phenols
US2862857A (en) *	1954-07-01	1958-12-02	Hercules Powder Co Ltd	Azeotropic distillation of monohydric and dihydric phenols
GB786341A (en) *	1955-02-23	1957-11-13	Distillers Co Yeast Ltd	Manufacture of catechol
FR1177423A (fr) *	1956-06-22	1959-04-24	Edogawa Kagaku Kogyo Kabushiki	Procédé de décomposition acide des hydroperoxydes organiques en vue de la production du phénol, de ses homologues et des composés du carbonyle
GB819450A (en) *	1957-03-15	1959-09-02	Bataafsche Petroleum Maatchapp	Process for the conversion of hydroperoxides of secondary alkyl aryls into phenols and ketones
GB873676A (en)	1958-08-08	1961-07-26	Distillers Co Yeast Ltd	Manufacture of resorcinol
GB857113A (en)	1958-08-08	1960-12-29	Distillers Co Yeast Ltd	Manufacture of resorcinol
BE642717A (fr)	1963-01-19
US3376352A (en) *	1963-02-21	1968-04-02	Montedison Spa	Process for producing hydroquinone from p-dialkyl-benzene-bis-hydroperoxides
US4207264A (en) *	1969-10-29	1980-06-10	The Goodyear Tire & Rubber Company	Rearrangement of aralkyl hydroperoxides to form phenols and carbonyl compounds
GB1342835A (en)	1970-03-05	1974-01-03	Signal Chemical Co	Process for the neutralization of rearrangement reaction products and process for the continuous isolation of dihydric phenols
US3882093A (en) *	1974-01-02	1975-05-06	Du Pont	Sulfonyl-containing fluorocarbon vinyl ethers and ion exchange membrane formed therefrom
FR2327979A1 (fr) *	1975-10-13	1977-05-13	Sumitomo Chemical Co	Procede de preparation d'hydroxydes aromatiques et de cetones aliphatiques
US4041090A (en) *	1976-03-04	1977-08-09	Shell Oil Company	Ethylbenzene process using an unsupported perfluorinated polymer catalyst
US4022847A (en)	1976-03-04	1977-05-10	Shell Oil Company	Hydrocarbon conversion process using an unsupported perfluorinated polymer catalyst
US4147726A (en) *	1976-11-08	1979-04-03	Phillips Petroleum Company	Acid-catalyzed hydrolysis of organic hydroperoxide employing a polar solvent and phenol as reaction medium
US4210606A (en) *	1979-06-15	1980-07-01	Gulf Research And Development Company	Decomposition of cumene hydroperoxide with a halogen-substituted thiophenol catalyst

1980
- 1980-03-14 US US06/130,401 patent/US4339613A/en not_active Expired - Lifetime
1981
- 1981-03-04 BE BE0/203999A patent/BE887779A/fr not_active IP Right Cessation
- 1981-03-06 FR FR8104481A patent/FR2478075A1/fr not_active Withdrawn
- 1981-03-12 GB GB08405212A patent/GB2137224B/en not_active Expired
- 1981-03-12 DE DE3109339A patent/DE3109339C2/de not_active Expired
- 1981-03-12 GB GB8107820A patent/GB2071662B/en not_active Expired
- 1981-03-13 NL NL8101250A patent/NL8101250A/nl not_active Application Discontinuation
- 1981-03-13 CA CA000372944A patent/CA1144945A/fr not_active Expired
- 1981-03-13 IT IT67354/81A patent/IT1144702B/it active
- 1981-03-14 JP JP3599581A patent/JPS56142226A/ja active Pending
1983
- 1983-11-24 GB GB08331325A patent/GB2137222B/en not_active Expired

Also Published As

Publication number	Publication date
BE887779A (fr)	1981-09-04
US4339613A (en)	1982-07-13
GB8405212D0 (en)	1984-04-04
GB2137224B (en)	1985-04-17
IT1144702B (it)	1986-10-29
GB2137224A (en)	1984-10-03
GB2071662A (en)	1981-09-23
DE3109339A1 (de)	1981-12-24
GB2071662B (en)	1985-01-23
FR2478075A1 (fr)	1981-09-18
GB2137222B (en)	1985-04-17
DE3109339C2 (de)	1984-09-13
IT8167354A0 (it)	1981-03-13
GB8331325D0 (en)	1984-01-04
CA1144945A (fr)	1983-04-19
GB2137222A (en)	1984-10-03
JPS56142226A (en)	1981-11-06

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-11-02	BV	The patent application has lapsed

Publication	Publication Date	Title
DE2826016C3 (de)	1981-06-11	Katalysator zur Umwandlung von Kohlenwasserstoffen
NL8101250A (nl)	1981-10-01	Werkwijze voor het bereiden van resorcinol.
JPH0312938B2 (fr)	1991-02-21
US2125968A (en)	1938-08-09	Manufacture of aromatic alcohols
Luong et al.	2004	Use of methanesulfonic acid as catalyst for the production of linear alkylbenzenes
JPS6258083B2 (fr)	1987-12-04
Koltunov et al.	2004	Superelectrophilic activation of polyfunctional organic compounds using zeolites and other solid acids
Smith et al.	2012	Highly regioselective di-tert-amylation of naphthalene over reusable H-mordenite zeolite
US4339614A (en)	1982-07-13	Superacid catalyzed preparation of resorcinol from meta-isopropylphenol
US4547604A (en)	1985-10-15	Selective isopropylation of cumene to meta-diisopropylbenzene
US4104315A (en)	1978-08-01	Process for separating an ar, ar-dihalo-ar-alkylbenzene from an isomeric mixture of ar, ar-dihalo-ar-alkylbenzenes
JPS6136498B2 (fr)	1986-08-19
EP2534116B1 (fr)	2014-09-24	Procédé de préparation d'alkyltoluènes m-substitués par isomérisation avec des liquides ioniques en tant que catalyseurs
US5210353A (en)	1993-05-11	Aromatic transformation process
US4547606A (en)	1985-10-15	Selective isomerization of di-isopropyl benzene to meta-di-isopropyl benzene
US4329524A (en)	1982-05-11	Separation of 3,5-dichlorocumene from a mixture of 3,5-dichlorocumene and 2,4-dichlorocumene
US2563050A (en)	1951-08-07	Treatment of olefins with liquid anhydrous hydrogen bromide
JP2586647B2 (ja)	1997-03-05	ｐ―体を高含量とするジアルキルベンゼンの製造方法
US2848512A (en)	1958-08-19	Preparation of hydrindacenes
US3306943A (en)	1967-02-28	Process for the preparation of p-dhsopropylbenzene
DE19513117A1 (de)	1996-10-10	Verfahren zur Alkylierung und Transalkylierung von Aromaten
Kovacic et al.	1963	Reaction of Antimony Pentachloride with Monoalkylbenzenes1
US3487119A (en)	1969-12-30	Production of 3,4,5-trimethyl-1-secondary alkyl benzenes
US3985819A (en)	1976-10-12	Process for producing alkylnaphthalenes
US2480267A (en)	1949-08-30	Production of bicycloalkyl aromatic compounds