CS250861B1 - Method of arylalkylation of phenol and/or alkylphenol - Google Patents

Method of arylalkylation of phenol and/or alkylphenol Download PDF

Info

Publication number: CS250861B1
Authority: CS; Czechoslovakia
Prior art keywords: phenol; methylstyrene; arylalkylation; weight; styrene
Prior art date: 1984-01-23

Application number

CS84496A

Other languages

Czech (cs)

English (en)

Slovak (sk)

Inventor

Vendelin Macho

Ludovit Jurecek

Ludovit Brezula

Karol Hlinstak

Milan Polievka

Sergej P Cernych

Galina V Abramova

Genadij P Pavlov

Original Assignee

Vendelin Macho

Ludovit Jurecek

Ludovit Brezula

Karol Hlinstak

Milan Polievka

Sergej P Cernych

Galina V Abramova

Genadij P Pavlov

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.)

1984-01-23

Filing date

1984-01-23

Publication date

1987-05-14

1984-01-23 Application filed by Vendelin Macho, Ludovit Jurecek, Ludovit Brezula, Karol Hlinstak, Milan Polievka, Sergej P Cernych, Galina V Abramova, Genadij P Pavlov filed Critical Vendelin Macho

1984-01-23 Priority to CS84496A priority Critical patent/CS250861B1/cs

1984-11-10 Priority to SU847773611A priority patent/SU1731767A1/ru

1986-04-07 Priority to BG74421A priority patent/BG48017A1/xx

1986-04-07 Priority to DD86288906A priority patent/DD261497A3/de

1987-05-14 Publication of CS250861B1 publication Critical patent/CS250861B1/cs

Links

ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 79
238000000034 method Methods 0.000 title claims description 10
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 49
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 44
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 31
239000003054 catalyst Substances 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 23
WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 17
XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims description 17
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 claims description 16
CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
239000000539 dimer Substances 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
230000003197 catalytic effect Effects 0.000 claims description 8
QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
-1 aluminum compound Chemical class 0.000 claims description 7
238000004821 distillation Methods 0.000 claims description 7
MMDVBQJVKNNYLU-UHFFFAOYSA-N 1-phenoxyethylbenzene Chemical compound C=1C=CC=CC=1C(C)OC1=CC=CC=C1 MMDVBQJVKNNYLU-UHFFFAOYSA-N 0.000 claims description 6
229910019142 PO4 Inorganic materials 0.000 claims description 6
NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
239000010452 phosphate Substances 0.000 claims description 6
239000002994 raw material Substances 0.000 claims description 6
229910052782 aluminium Inorganic materials 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
239000007791 liquid phase Substances 0.000 claims description 5
FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 5
WYZIVNCBUWDCOZ-UHFFFAOYSA-N 2-(1-phenylethyl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1 WYZIVNCBUWDCOZ-UHFFFAOYSA-N 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
239000002638 heterogeneous catalyst Substances 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000004927 clay Substances 0.000 claims description 3
239000012808 vapor phase Substances 0.000 claims description 3
XHASMJXNUHCHBL-UHFFFAOYSA-N 4-(1-phenylethyl)phenol Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=CC=C1 XHASMJXNUHCHBL-UHFFFAOYSA-N 0.000 claims description 2
238000004061 bleaching Methods 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
POXZXJBZNXHTAK-UHFFFAOYSA-N (1-methoxy-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(C)(OC)C1=CC=CC=C1 POXZXJBZNXHTAK-UHFFFAOYSA-N 0.000 claims 1
238000000354 decomposition reaction Methods 0.000 claims 1
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
208000022345 tetraamelia syndrome Diseases 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
238000009835 boiling Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
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 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000010457 zeolite Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000005265 energy consumption Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical class CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
229940031826 phenolate Drugs 0.000 description 3
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000003421 catalytic decomposition reaction Methods 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000006735 epoxidation reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
MRZGGLIGGZHSBZ-UHFFFAOYSA-N 1-phenyldecan-1-ol Chemical compound CCCCCCCCCC(O)C1=CC=CC=C1 MRZGGLIGGZHSBZ-UHFFFAOYSA-N 0.000 description 1
LYAYPVCAAQCSGB-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)propan-2-ol Chemical compound CC1=CC=CC(C(C)(C)O)=C1C LYAYPVCAAQCSGB-UHFFFAOYSA-N 0.000 description 1
IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical group COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
YHZQOKUDQQISEW-UHFFFAOYSA-N 4-Cumylphenol Natural products C1=CC(C(C)C)=CC=C1C1=CC=C(O)C=C1 YHZQOKUDQQISEW-UHFFFAOYSA-N 0.000 description 1
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
GAVIKYOCHJLRAD-UHFFFAOYSA-N C(C)(C)(C1=CC=CC=C1)C1(CC=CC=C1)O Chemical compound C(C)(C)(C1=CC=CC=C1)C1(CC=CC=C1)O GAVIKYOCHJLRAD-UHFFFAOYSA-N 0.000 description 1
PIIOQVAAZCSCLQ-UHFFFAOYSA-N C1(=CC=CC=C1)O.CC(O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)O.CC(O)C1=CC=CC=C1 PIIOQVAAZCSCLQ-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Natural products C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
QFVBCWBVMGRFQN-UHFFFAOYSA-N [Ba].[Cr].[Cu] Chemical compound [Ba].[Cr].[Cu] QFVBCWBVMGRFQN-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
LVDQFDJTXBHRGJ-UHFFFAOYSA-K aluminum;2-ethylphenolate Chemical compound [Al+3].CCC1=CC=CC=C1[O-].CCC1=CC=CC=C1[O-].CCC1=CC=CC=C1[O-] LVDQFDJTXBHRGJ-UHFFFAOYSA-K 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
229910052593 corundum Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
YSTSZKYCLOUEDE-UHFFFAOYSA-N dimethyl(phenyl)alumane Chemical compound C[Al](C)C1=CC=CC=C1 YSTSZKYCLOUEDE-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
DBYJIWYDEHDKJS-UHFFFAOYSA-N hexa-2,5-dien-1-ol Chemical compound OCC=CCC=C DBYJIWYDEHDKJS-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
229910001392 phosphorus oxide Inorganic materials 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
125000003410 quininyl group Chemical group 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
HWIORSQIDHLVBH-UHFFFAOYSA-N trihydroxy phosphate Chemical compound OOP(=O)(OO)OO HWIORSQIDHLVBH-UHFFFAOYSA-N 0.000 description 1
OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical class [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910001845 yogo sapphire Inorganic materials 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

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS84496A 1984-01-23 1984-01-23 Method of arylalkylation of phenol and/or alkylphenol CS250861B1 (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CS84496A CS250861B1 (en)	1984-01-23	1984-01-23	Method of arylalkylation of phenol and/or alkylphenol
SU847773611A SU1731767A1 (ru)	1984-01-23	1984-11-10	Способ получени арилалкилфенолов
BG74421A BG48017A1 (en)	1984-01-23	1986-04-07	Method for aryl alkylating of phenol and/or of alkylphenol
DD86288906A DD261497A3 (de)	1984-01-23	1986-04-07	Methode zur arylalkylierung von phenol und/oder alkylphenol

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CS84496A CS250861B1 (en)	1984-01-23	1984-01-23	Method of arylalkylation of phenol and/or alkylphenol
DD86288906A DD261497A3 (de)	1984-01-23	1986-04-07	Methode zur arylalkylierung von phenol und/oder alkylphenol

Publications (1)

Publication Number	Publication Date
CS250861B1 true CS250861B1 (en)	1987-05-14

Family

ID=25745295

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS84496A CS250861B1 (en)	1984-01-23	1984-01-23	Method of arylalkylation of phenol and/or alkylphenol

Country Status (4)

Country	Link
BG (1)	BG48017A1 (de)
CS (1)	CS250861B1 (de)
DD (1)	DD261497A3 (de)
SU (1)	SU1731767A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114478440B (zh) *	2020-10-26	2024-07-23	中国石油化工股份有限公司	一种环氧丙烷的制备方法及得到的环氧丙烷

1984
- 1984-01-23 CS CS84496A patent/CS250861B1/cs unknown
- 1984-11-10 SU SU847773611A patent/SU1731767A1/ru active
1986
- 1986-04-07 DD DD86288906A patent/DD261497A3/de not_active IP Right Cessation
- 1986-04-07 BG BG74421A patent/BG48017A1/xx unknown

Also Published As

Publication number	Publication date
BG48017A1 (en)	1990-11-15
SU1731767A1 (ru)	1992-05-07
DD261497A3 (de)	1988-11-02

Publication	Publication Date	Title
US4391997A (en)	1983-07-05	Ion exchange catalyzed bisphenol process
US4870217A (en)	1989-09-26	Method for production of phenol/acetone from cumene hydroperoxide
US2714120A (en)	1955-07-26	Method of preparing aralkylated phenolic compounds
EP0210366A1 (de)	1987-02-04	Verfahren zur Herstellung von Bisphenol A
EP0029333A1 (de)	1981-05-27	Langkettige Alkylphenole
EP0125066A1 (de)	1984-11-14	Herstellung von Phenol
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