SK14342000A3 - Spôsob výroby fenolu - Google Patents

Spôsob výroby fenolu Download PDF

Info

Publication number: SK14342000A3
Authority: SK; Slovakia
Prior art keywords: cumene; cyclohexylbenzene; phenol; cleavage; oxidation
Prior art date: 1999-09-30

Application number

SK1434-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Werner Pompetzki

Barneveld Heinrich Van

Otto Gerlich

Werner Kleinloh

Original Assignee

Phenolchemie Gmbh & Co. Kg

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.)

1999-09-30

Filing date

2000-09-25

Publication date

2001-07-10

2000-09-25 Application filed by Phenolchemie Gmbh & Co. Kg filed Critical Phenolchemie Gmbh & Co. Kg

2001-07-10 Publication of SK14342000A3 publication Critical patent/SK14342000A3/sk

Links

ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 37
238000000034 method Methods 0.000 title claims abstract description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 50
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims abstract description 50
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 34
HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims abstract description 29
238000003776 cleavage reaction Methods 0.000 claims abstract description 26
230000007017 scission Effects 0.000 claims abstract description 26
230000003647 oxidation Effects 0.000 claims abstract description 25
238000007254 oxidation reaction Methods 0.000 claims abstract description 25
239000000203 mixture Substances 0.000 claims abstract description 21
238000004519 manufacturing process Methods 0.000 claims abstract description 13
210000004124 hock Anatomy 0.000 claims abstract description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
239000001301 oxygen Substances 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
-1 aryl hydroperoxides Chemical class 0.000 claims abstract description 6
239000007789 gas Substances 0.000 claims abstract description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 11
OECMNLAWCROQEE-UHFFFAOYSA-N cyclohexylbenzene;hydrogen peroxide Chemical compound OO.C1CCCCC1C1=CC=CC=C1 OECMNLAWCROQEE-UHFFFAOYSA-N 0.000 claims description 8
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
229910001882 dioxygen Inorganic materials 0.000 claims description 4
238000004821 distillation Methods 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000002432 hydroperoxides Chemical class 0.000 abstract description 2
239000000047 product Substances 0.000 description 18
238000010543 cumene process Methods 0.000 description 12
239000003054 catalyst Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000007171 acid catalysis Methods 0.000 description 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
238000005265 energy consumption Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DTTDXHDYTWQDCS-UHFFFAOYSA-N 1-phenylcyclohexan-1-ol Chemical compound C=1C=CC=CC=1C1(O)CCCCC1 DTTDXHDYTWQDCS-UHFFFAOYSA-N 0.000 description 1
MAHPVQDVMLWUAG-UHFFFAOYSA-N 1-phenylhexan-1-one Chemical compound CCCCCC(=O)C1=CC=CC=C1 MAHPVQDVMLWUAG-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
RZWHPSRTQBWZMA-UHFFFAOYSA-A [O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[B+3].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[B+3].[B+3].[B+3].[B+3] Chemical compound [O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[B+3].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[B+3].[B+3].[B+3].[B+3] RZWHPSRTQBWZMA-UHFFFAOYSA-A 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
RWYFURDDADFSHT-RBBHPAOJSA-N diane Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1=C(Cl)C2=CC(=O)[C@@H]3CC3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RWYFURDDADFSHT-RBBHPAOJSA-N 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
230000004992 fission Effects 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
LKWKIVHUCKVYOA-UHFFFAOYSA-N phosphoric acid;trifluoroborane Chemical compound FB(F)F.OP(O)(O)=O LKWKIVHUCKVYOA-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000005496 tempering Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK1434-2000A 1999-09-30 2000-09-25 Spôsob výroby fenolu SK14342000A3 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19946886A DE19946886A1 (de)	1999-09-30	1999-09-30	Verfahren zur Herstellung von Phenol

Publications (1)

Publication Number	Publication Date
SK14342000A3 true SK14342000A3 (sk)	2001-07-10

Family

ID=7923856

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1434-2000A SK14342000A3 (sk)	1999-09-30	2000-09-25	Spôsob výroby fenolu

Country Status (10)

Country	Link
EP (1)	EP1088808A1 (cs)
JP (1)	JP2001097902A (cs)
KR (1)	KR20010050696A (cs)
CN (1)	CN1290680A (cs)
BG (1)	BG104777A (cs)
BR (1)	BR0004525A (cs)
CZ (1)	CZ20003479A3 (cs)
DE (1)	DE19946886A1 (cs)
PL (1)	PL342871A1 (cs)
SK (1)	SK14342000A3 (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7335797B2 (en) *	2002-03-14	2008-02-26	Eurotechnica Development & Licensing S.P.A.	Process for the synthesis of cumene hydroperoxide
JP2007099746A (ja) *	2005-09-06	2007-04-19	Ube Ind Ltd	フェノールおよびシクロアルカノンの製造方法
CN101925561B (zh) *	2008-02-12	2014-04-16	埃克森美孚化学专利公司	制备环己基苯的方法
EP2303809A1 (en) *	2008-04-25	2011-04-06	ExxonMobil Chemical Patents Inc.	Process for producing phenol and/or cyclohexanone

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3959381A (en) *	1970-10-22	1976-05-25	Texaco Inc.	Phenol and cyclohexanone manufacture

1999
- 1999-09-30 DE DE19946886A patent/DE19946886A1/de not_active Withdrawn
2000
- 2000-08-11 EP EP00117402A patent/EP1088808A1/de not_active Withdrawn
- 2000-09-19 BG BG104777A patent/BG104777A/xx unknown
- 2000-09-21 CZ CZ20003479A patent/CZ20003479A3/cs unknown
- 2000-09-25 SK SK1434-2000A patent/SK14342000A3/sk unknown
- 2000-09-27 JP JP2000294584A patent/JP2001097902A/ja active Pending
- 2000-09-28 BR BR0004525-0A patent/BR0004525A/pt not_active Application Discontinuation
- 2000-09-28 KR KR1020000056955A patent/KR20010050696A/ko not_active Withdrawn
- 2000-09-29 CN CN00129069A patent/CN1290680A/zh active Pending
- 2000-09-29 PL PL00342871A patent/PL342871A1/xx unknown

Also Published As

Publication number	Publication date
PL342871A1 (en)	2001-04-09
EP1088808A1 (de)	2001-04-04
BG104777A (en)	2001-09-28
BR0004525A (pt)	2001-04-17
KR20010050696A (ko)	2001-06-15
CZ20003479A3 (cs)	2002-03-13
CN1290680A (zh)	2001-04-11
JP2001097902A (ja)	2001-04-10
DE19946886A1 (de)	2001-04-05

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