JPH0552816B2 - - Google Patents

Info

Publication number: JPH0552816B2
Authority: JP; Japan
Prior art keywords: diisopropylbenzene; dihydroperoxide; oxidation; hydroquinone; weight
Prior art date: 1987-01-07
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

JP62001550A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63174941A (ja

Inventor

Kosukimiisu Sarume

Haimera Taruu

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.)

Neste Oyj

Original Assignee

Neste Oyj

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.)

1987-01-07

Filing date

1987-01-07

Publication date

1993-08-06

1987-01-07 Application filed by Neste Oyj filed Critical Neste Oyj

1987-01-07 Priority to JP62001550A priority Critical patent/JPS63174941A/ja

1988-07-19 Publication of JPS63174941A publication Critical patent/JPS63174941A/ja

1993-08-06 Publication of JPH0552816B2 publication Critical patent/JPH0552816B2/ja

Status Granted legal-status Critical Current

Links

238000007254 oxidation reaction Methods 0.000 claims description 34
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 25
230000003647 oxidation Effects 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 19
230000002378 acidificating effect Effects 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 15
239000006227 byproduct Substances 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 10
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 claims description 9
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 8
-1 alkyl aromatic hydrocarbon Chemical class 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
238000010543 cumene process Methods 0.000 claims description 6
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 claims description 5
UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 claims description 5
239000003456 ion exchange resin Substances 0.000 claims description 5
229920003303 ion-exchange polymer Polymers 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 claims description 4
YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
238000001816 cooling Methods 0.000 claims description 3
QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 claims description 2
CYBSWFUWEZFKNJ-UHFFFAOYSA-N 2-phenylhexane Chemical compound CCCCC(C)C1=CC=CC=C1 CYBSWFUWEZFKNJ-UHFFFAOYSA-N 0.000 claims description 2
150000004996 alkyl benzenes Chemical class 0.000 claims description 2
SLVCCWGFGQVDMN-UHFFFAOYSA-N hexan-3-ylbenzene Chemical compound CCCC(CC)C1=CC=CC=C1 SLVCCWGFGQVDMN-UHFFFAOYSA-N 0.000 claims description 2
239000013078 crystal Substances 0.000 claims 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 14
229930195733 hydrocarbon Natural products 0.000 description 11
150000002430 hydrocarbons Chemical class 0.000 description 11
239000012452 mother liquor Substances 0.000 description 10
REGMWDPZVFOJLY-UHFFFAOYSA-N 1,4-bis(2-hydroperoxypropan-2-yl)benzene Chemical compound OOC(C)(C)C1=CC=C(C(C)(C)OO)C=C1 REGMWDPZVFOJLY-UHFFFAOYSA-N 0.000 description 9
239000004215 Carbon black (E152) Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
150000002978 peroxides Chemical class 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
SBUBPFHJZHQNNT-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.OO.CC(C)C1=CC=CC=C1C(C)C SBUBPFHJZHQNNT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000002432 hydroperoxides Chemical class 0.000 description 3
239000002994 raw material Substances 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
IROSBXFYXRIPRU-UHFFFAOYSA-N 1,3-bis(2-hydroperoxypropan-2-yl)benzene Chemical compound OOC(C)(C)C1=CC=CC(C(C)(C)OO)=C1 IROSBXFYXRIPRU-UHFFFAOYSA-N 0.000 description 1
ADNTWSHRSHPGHG-UHFFFAOYSA-N 1,3-di(propan-2-yl)benzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC(C(C)C)=C1 ADNTWSHRSHPGHG-UHFFFAOYSA-N 0.000 description 1
PIUUDKDOAUICQP-UHFFFAOYSA-N 2-methylpentan-2-ylbenzene Chemical compound CCCC(C)(C)C1=CC=CC=C1 PIUUDKDOAUICQP-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
NQRMTOKLHZNAQH-UHFFFAOYSA-N 3-methylbutan-2-ylbenzene Chemical compound CC(C)C(C)C1=CC=CC=C1 NQRMTOKLHZNAQH-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
229930007927 cymene Natural products 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
CAEGRAMHTMWFPP-UHFFFAOYSA-N heptan-2-ylbenzene Chemical compound CCCCCC(C)C1=CC=CC=C1 CAEGRAMHTMWFPP-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
LTHAIAJHDPJXLG-UHFFFAOYSA-N pentan-2-ylbenzene Chemical compound CCCC(C)C1=CC=CC=C1 LTHAIAJHDPJXLG-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002904 solvent Substances 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)

JP62001550A 1987-01-07 1987-01-07 ヒドロキノンの製法 Granted JPS63174941A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP62001550A JPS63174941A (ja)	1987-01-07	1987-01-07	ヒドロキノンの製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62001550A JPS63174941A (ja)	1987-01-07	1987-01-07	ヒドロキノンの製法

Publications (2)

Publication Number	Publication Date
JPS63174941A JPS63174941A (ja)	1988-07-19
JPH0552816B2 true JPH0552816B2 (de)	1993-08-06

Family

ID=11504634

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62001550A Granted JPS63174941A (ja)	1987-01-07	1987-01-07	ヒドロキノンの製法

Country Status (1)

Country	Link
JP (1)	JPS63174941A (de)

1987
- 1987-01-07 JP JP62001550A patent/JPS63174941A/ja active Granted

Also Published As

Publication number	Publication date
JPS63174941A (ja)	1988-07-19

Publication	Publication Date	Title
US4283570A (en)	1981-08-11	Process for preparing resorcinol
JP3769050B2 (ja)	2006-04-19	フェノールの製造方法
US7482493B2 (en)	2009-01-27	Method for the production of phenol and acetone
US4339615A (en)	1982-07-13	Process for producing resorcinol
US7485758B2 (en)	2009-02-03	Method for the production of phenol and acetone
US2856433A (en)	1958-10-14	Separation of organic compounds
EP0105019B1 (de)	1987-08-05	Verfahren zur Gewinnung von Dihydroxybenzol
JPH0552816B2 (de)	1993-08-06
EP0322245A2 (de)	1989-06-28	Verfahren zur Herstellung von Resorcin
DE2942069A1 (de)	1980-04-24	Verbessertes verfahren zur herstellung aromatischer hydroperoxide
EP0271623B1 (de)	1990-03-07	Verfahren zur Herstellung von Hydrochinon
JPS6123772B2 (de)	1986-06-07
US4847437A (en)	1989-07-11	Oxidation and subsequent decomposition of dihydroperoxide
US11939282B2 (en)	2024-03-26	Method for decomposing phenolic by-product
JPS626529B2 (de)	1987-02-12
US8003827B2 (en)	2011-08-23	Method for producing phenol and acetone
EP3943475B1 (de)	2025-10-01	Optimierung der herstellung von o-sulfoniertem phenol zur aufspaltung von cumenhydroperoxid
JPS63258826A (ja)	1988-10-26	ヒドロキシ芳香族炭化水素の製造方法
JPH037649B2 (de)	1991-02-04
JPS63239241A (ja)	1988-10-05	ヒドロキシベンゼン類の製法
US4169210A (en)	1979-09-25	Oxidation of diethylbenzenes
SU740763A1 (ru)	1980-06-15	Способ получени дигидроперекисей м- или п-диизопропилбензола или их смеси
JPH0466463B2 (de)	1992-10-23
US3923909A (en)	1975-12-02	Oxidation of diethylbenzenes
JPH0234332B2 (de)	1990-08-02