CS277195B6 - Cyclohexanol and/or cyclohexanone production method - Google Patents

Cyclohexanol and/or cyclohexanone production method Download PDF

Info

Publication number: CS277195B6
Authority: CS; Czechoslovakia
Prior art keywords: cyclohexene; stream; benzene; cyclohexane; cyclohexanol
Prior art date: 1988-04-21

Application number

CS892478A

Other languages

Czech (cs)

English (en)

Other versions

CS8902478A2 (en

Inventor

Geem Paul Christiaan Van

Den Brink Franciscus Tobia Van

Original Assignee

Stamicarbon

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.)

1988-04-21

Filing date

1989-04-20

Publication date

1992-12-16

1989-04-20 Application filed by Stamicarbon filed Critical Stamicarbon

1991-07-16 Publication of CS8902478A2 publication Critical patent/CS8902478A2/cs

1992-12-16 Publication of CS277195B6 publication Critical patent/CS277195B6/cs

Links

JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 68
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims abstract description 31
238000004519 manufacturing process Methods 0.000 title abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 135
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 115
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 42
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 31
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 29
238000006243 chemical reaction Methods 0.000 claims abstract description 22
238000006703 hydration reaction Methods 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 14
238000007254 oxidation reaction Methods 0.000 claims abstract description 13
230000036571 hydration Effects 0.000 claims abstract description 11
230000003647 oxidation Effects 0.000 claims abstract description 11
239000011541 reaction mixture Substances 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
238000011144 upstream manufacturing Methods 0.000 claims 1
239000003054 catalyst Substances 0.000 description 11
238000004821 distillation Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 8
238000000926 separation method Methods 0.000 description 8
238000006213 oxygenation reaction Methods 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000002994 raw material Substances 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
229910052707 ruthenium Inorganic materials 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229920004482 WACKER® Polymers 0.000 description 2
229910021536 Zeolite Inorganic materials 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
229910052720 vanadium Inorganic materials 0.000 description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
239000010457 zeolite Substances 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
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
229910000990 Ni alloy Inorganic materials 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
-1 cyclohexanol ester Chemical class 0.000 description 1
GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
UCZUCGRGTXIWLR-UHFFFAOYSA-N cyclohexyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1CCCCC1 UCZUCGRGTXIWLR-UHFFFAOYSA-N 0.000 description 1
238000010586 diagram Methods 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
230000000694 effects Effects 0.000 description 1
229910052675 erionite Inorganic materials 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 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
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/10—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons
- C07C27/12—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons with oxygen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Seasonings (AREA)

CS892478A 1988-04-21 1989-04-20 Cyclohexanol and/or cyclohexanone production method CS277195B6 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL8801036A NL8801036A (nl)	1988-04-21	1988-04-21	Werkwijze voor de bereiding van cyclohexanol en/of cyclohexanon.

Publications (2)

Publication Number	Publication Date
CS8902478A2 CS8902478A2 (en)	1991-07-16
CS277195B6 true CS277195B6 (en)	1992-12-16

Family

ID=19852177

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS892478A CS277195B6 (en)	1988-04-21	1989-04-20	Cyclohexanol and/or cyclohexanone production method

Country Status (16)

Country	Link
US (1)	US4927974A (de)
EP (1)	EP0340827B1 (de)
JP (1)	JP2688246B2 (de)
KR (1)	KR920000443B1 (de)
CN (1)	CN1023216C (de)
AT (1)	ATE84776T1 (de)
BR (1)	BR8901880A (de)
CA (1)	CA1327212C (de)
CS (1)	CS277195B6 (de)
DE (1)	DE68904466T2 (de)
ES (1)	ES2038819T3 (de)
GE (1)	GEP19960308B (de)
MX (1)	MX169563B (de)
NL (1)	NL8801036A (de)
RU (1)	RU1833359C (de)
SG (1)	SG25293G (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5218704A (en) *	1989-10-30	1993-06-08	Texas Instruments	Real-time power conservation for portable computers
DE4029485A1 (de) *	1990-09-18	1992-03-19	Basf Ag	Verfahren zur abtrennung von cyclohexen aus gemischen mit benzol und cyclohexan
CN1073077C (zh) *	1997-07-31	2001-10-17	巴陵石油化工公司鹰山石油化工厂	环己醇脱氢方法的改进
EP1028109A1 (de) *	1999-02-12	2000-08-16	Dsm N.V.	Verfahren zur Herstellung von Epsilon-Caprolactam
JP4601805B2 (ja) *	2000-11-24	2010-12-22	ダイセル化学工業株式会社	シクロヘキサンの酸化方法
DE10209701A1 (de) *	2002-03-06	2003-09-18	Basf Ag	Verfahren zur Herstellung von Cyclohexanol aus Benzol
RU2205175C1 (ru) *	2002-03-20	2003-05-27	Институт катализа им. Г.К. Борескова СО РАН	Способ получения циклогексанона
RU2205819C1 (ru) *	2002-03-20	2003-06-10	Институт катализа им. Г.К.Борескова СО РАН	Способ получения циклогексанона из бензола
EA011769B1 (ru) *	2004-10-27	2009-06-30	ДСМ АйПи АССЕТС Б.В.	Способ получения циклогексанола и циклогексанона
TWI612031B (zh)	2012-09-18	2018-01-21	China Petrochemical Technology Co Ltd	一種聯產環己醇和鏈烷醇的方法和裝置
CN103265418A (zh) *	2013-06-08	2013-08-28	南京德力菲技术咨询有限公司	一种水合环己烯法环己醇制己内酰胺原料环己酮的方法
CN110872208B (zh) *	2019-02-18	2023-10-27	南京匹亚化工有限公司	一种耦合环己烷混合物脱氢技术的环己醇制备方法
CN111217684A (zh) *	2019-10-29	2020-06-02	山西潞宝兴海新材料有限公司	一种提高环己酮收率的生产方法
CN115838325A (zh) *	2021-09-18	2023-03-24	中国石油化工股份有限公司	一种环己烯与环己烷耦合制环己酮的方法
CN115838316A (zh) *	2021-09-18	2023-03-24	中国石油化工股份有限公司	一种苯二步加氢生产环己酮方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7905781A (nl) *	1979-07-26	1981-01-28	Stamicarbon	Werkwijze voor het bereiden van cyclohexanol.
NL8006602A (nl) *	1980-12-04	1982-07-01	Stamicarbon	Werkwijze voor het bereiden van cyclohexanol en/of cyclohexanon.
DE3203286A1 (de) *	1981-03-20	1982-12-09	The Agency of Industrial Science and Technology, Tokyo	Verfahren zur herstellung von zyklohexanon
JPS59193836A (ja) *	1983-04-15	1984-11-02	Asahi Chem Ind Co Ltd	アルコ−ル類の製造法
US4507512A (en) *	1983-05-31	1985-03-26	Toa Nenryo Kogyo Kabushiki Kaisha	Process for hydration of olefins
JPS60104028A (ja) *	1983-11-09	1985-06-08	Asahi Chem Ind Co Ltd	環状アルコ−ルの製造法

1988
- 1988-04-21 NL NL8801036A patent/NL8801036A/nl not_active Application Discontinuation
1989
- 1989-04-06 US US07/334,142 patent/US4927974A/en not_active Expired - Fee Related
- 1989-04-13 RU SU894613851A patent/RU1833359C/ru active
- 1989-04-17 ES ES198989200970T patent/ES2038819T3/es not_active Expired - Lifetime
- 1989-04-17 EP EP89200970A patent/EP0340827B1/de not_active Expired - Lifetime
- 1989-04-17 AT AT89200970T patent/ATE84776T1/de not_active IP Right Cessation
- 1989-04-17 DE DE8989200970T patent/DE68904466T2/de not_active Expired - Fee Related
- 1989-04-19 CA CA000597103A patent/CA1327212C/en not_active Expired - Fee Related
- 1989-04-19 CN CN89102604A patent/CN1023216C/zh not_active Expired - Fee Related
- 1989-04-19 KR KR1019890005239A patent/KR920000443B1/ko not_active Expired
- 1989-04-20 BR BR898901880A patent/BR8901880A/pt not_active IP Right Cessation
- 1989-04-20 CS CS892478A patent/CS277195B6/cs not_active IP Right Cessation
- 1989-04-20 MX MX015740A patent/MX169563B/es unknown
- 1989-04-21 JP JP1100347A patent/JP2688246B2/ja not_active Expired - Lifetime
1993
- 1993-03-06 SG SG252/93A patent/SG25293G/en unknown
- 1993-06-21 GE GEAP1993907A patent/GEP19960308B/en unknown

Also Published As

Publication number	Publication date
NL8801036A (nl)	1989-11-16
BR8901880A (pt)	1989-11-28
CA1327212C (en)	1994-02-22
US4927974A (en)	1990-05-22
MX169563B (es)	1993-07-12
ATE84776T1 (de)	1993-02-15
JP2688246B2 (ja)	1997-12-08
CS8902478A2 (en)	1991-07-16
DE68904466D1 (de)	1993-03-04
ES2038819T3 (es)	1993-08-01
SG25293G (en)	1993-05-21
EP0340827B1 (de)	1993-01-20
KR890015984A (ko)	1989-11-27
RU1833359C (en)	1993-08-07
CN1038273A (zh)	1989-12-27
GEP19960308B (en)	1996-02-20
EP0340827A1 (de)	1989-11-08
JPH01316330A (ja)	1989-12-21
KR920000443B1 (ko)	1992-01-14
CN1023216C (zh)	1993-12-22
DE68904466T2 (de)	1993-08-19

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2002-01-16	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20010420

Publication	Publication Date	Title
RU2282625C2 (ru)	2006-08-27	Получение соединений оксирана
RU1839668C (ru)	1993-12-30	Способ получени фенола
US6841704B2 (en)	2005-01-11	Process for preparing cumene which is used in the preparation of phenol
EP1575888B1 (de)	2010-10-06	Gleichzeitige herstellung von phenol, aceton und alpha-methylstyren
EP2207762B1 (de)	2013-07-31	Verfahren zur herstellung von isopropanol durch flüssigphasenhydrierung
CS277195B6 (en)	1992-12-16	Cyclohexanol and/or cyclohexanone production method
US5245090A (en)	1993-09-14	Two-stage cleavage of cumene hydroperoxide
JP2774607B2 (ja)	1998-07-09	フェノールの製造方法およびその製造時の副生アセトンからプロピレンを得る方法
JP2001064213A (ja)	2001-03-13	気相における芳香族化合物のアルキル化法
EP1326820B1 (de)	2009-04-22	Hydrierung von spaltungsprodukten bei der phenolherstellung
JPH02231442A (ja)	1990-09-13	フェノールの製造方法
US4814511A (en)	1989-03-21	Working up cyclohexyl hydroperoxide containing reaction mixtures
EP0316142A2 (de)	1989-05-17	Verfahren zur Herstellung von Phenolen
JP2772839B2 (ja)	1998-07-09	芳香族ヒドロキシ化合物の製造方法
CN101128411B (zh)	2010-12-29	酚类的精制方法
JP5255318B2 (ja)	2013-08-07	アルキル化芳香族化合物の製造方法およびフェノールの製造方法
CN111675594A (zh)	2020-09-18	一种苯加氢烷基化生产环己基苯的方法
JP2004099491A (ja)	2004-04-02	ジアルキルペルオキシドの製造方法