JPH0438736B2 - - Google Patents

Info

Publication number: JPH0438736B2
Authority: JP; Japan
Prior art keywords: phenol; separated; xylenol; orthocresol; distillation
Prior art date: 1987-01-30
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

Application number

JP1866787A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63188636A (ja

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.)

1987-01-30

Filing date

1987-01-30

Publication date

1992-06-25

1987-01-30 Application filed filed Critical

1987-01-30 Priority to JP1866787A priority Critical patent/JPS63188636A/ja

1988-08-04 Publication of JPS63188636A publication Critical patent/JPS63188636A/ja

1992-06-25 Publication of JPH0438736B2 publication Critical patent/JPH0438736B2/ja

Status Granted legal-status Critical Current

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 48
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 44
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 32
239000003054 catalyst Substances 0.000 claims description 30
238000009835 boiling Methods 0.000 claims description 25
238000004821 distillation Methods 0.000 claims description 19
239000000126 substance Substances 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
-1 ortho-methylated phenol compound Chemical class 0.000 claims description 12
239000000843 powder Substances 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 8
239000006227 byproduct Substances 0.000 claims description 7
150000002989 phenols Chemical class 0.000 claims description 6
229910044991 metal oxide Inorganic materials 0.000 claims description 5
150000004706 metal oxides Chemical class 0.000 claims description 5
238000007599 discharging Methods 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims 1
238000000926 separation method Methods 0.000 description 21
238000000034 method Methods 0.000 description 19
239000000047 product Substances 0.000 description 12
239000007789 gas Substances 0.000 description 11
230000018044 dehydration Effects 0.000 description 9
238000006297 dehydration reaction Methods 0.000 description 9
NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000002245 particle Substances 0.000 description 5
BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000002994 raw material Substances 0.000 description 4
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
238000011109 contamination Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000004231 fluid catalytic cracking Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
150000003739 xylenols Chemical class 0.000 description 2
JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 1
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000002542 deteriorative effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
229920006380 polyphenylene oxide Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP1866787A 1987-01-30 1987-01-30 オルト位メチル化フエノ−ル化合物の製造方法 Granted JPS63188636A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP1866787A JPS63188636A (ja)	1987-01-30	1987-01-30	オルト位メチル化フエノ−ル化合物の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP1866787A JPS63188636A (ja)	1987-01-30	1987-01-30	オルト位メチル化フエノ−ル化合物の製造方法

Publications (2)

Publication Number	Publication Date
JPS63188636A JPS63188636A (ja)	1988-08-04
JPH0438736B2 true JPH0438736B2 (fr)	1992-06-25

Family

ID=11977960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1866787A Granted JPS63188636A (ja)	1987-01-30	1987-01-30	オルト位メチル化フエノ−ル化合物の製造方法

Country Status (1)

Country	Link
JP (1)	JPS63188636A (fr)

1987
- 1987-01-30 JP JP1866787A patent/JPS63188636A/ja active Granted

Also Published As

Publication number	Publication date
JPS63188636A (ja)	1988-08-04

Legal Events

Date	Code	Title	Description
2007-01-30	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
US4244879A (en)	1981-01-13	Preparation of maleic anhydride
EP0523728B1 (fr)	1995-12-27	Procédé continu de préparation du carbonate de diméthyle
JPH0320372B2 (fr)	1991-03-19
JPH0529374B2 (fr)	1993-04-30
Reddy et al.	2005	Esterification of succinic anhydride to di-(p-cresyl) succinate over Mn+-montmorillonite clay catalysts
US4294722A (en)	1981-10-13	Preparation of vanadium phosphorus catalysts
CA1197230A (fr)	1985-11-26	Preparation de catalyseurs mixtes au vanadium et a l'oxyde de phosphore, et leur emploi pour les procedes d'oxydation
JP3532763B2 (ja)	2004-05-31	メタクリル酸メチルの精製法
JP4651612B2 (ja)	2011-03-16	高純度フェノールの製造方法
JPH0438736B2 (fr)	1992-06-25
US4400557A (en)	1983-08-23	Process for the o-substitution of phenols
JPH0438737B2 (fr)	1992-06-25
US4154964A (en)	1979-05-15	Process for the purification of a phenol
EP0256479A2 (fr)	1988-02-24	Procédé pour la trans-halogénation catalytique d'un poly-iodo-benzène
JP2772839B2 (ja)	1998-07-09	芳香族ヒドロキシ化合物の製造方法
US6593501B2 (en)	2003-07-15	Process for the preparation of 2,6-xylenol
JPS6058932A (ja)	1985-04-05	メチル−ヒ−ブチルエ−テルの製造方法
CA1070328A (fr)	1980-01-22	Procede pour la preparation de cycloalcanones et de cycloalcanols
JP2001294543A (ja)	2001-10-23	ブチルフェノール類の脱ブチル化方法
JPH0521094B2 (fr)	1993-03-23
US4406824A (en)	1983-09-27	Catalysts for the o-substitution of phenols
US4400522A (en)	1983-08-23	Preparation of maleic anhydride
JP7537681B2 (ja)	2024-08-21	アクリル酸の製造方法
JPS62164635A (ja)	1987-07-21	フエノ−ル蒸留残渣からの有用物質の回収方法
JPS6312451B2 (fr)	1988-03-18