JPS6241657B2 - - Google Patents

Info

Publication number: JPS6241657B2
Authority: JP; Japan
Prior art keywords: formula; hydroperoxide; salt; reaction; iron
Prior art date: 1982-08-12
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

JP57140658A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5929632A (ja

Inventor

Haruhisa Harada

Hiroshi Maki

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.)

Sumitomo Chemical Co Ltd

Original Assignee

Sumitomo Chemical Co Ltd

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.)

1982-08-12

Filing date

1982-08-12

Publication date

1987-09-03

1982-08-12 Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd

1982-08-12 Priority to JP57140658A priority Critical patent/JPS5929632A/ja

1983-01-07 Priority to DE8383300093T priority patent/DE3363309D1/de

1983-01-07 Priority to EP83300093A priority patent/EP0084417B1/de

1983-01-07 Priority to US06/456,455 priority patent/US4486605A/en

1984-02-16 Publication of JPS5929632A publication Critical patent/JPS5929632A/ja

1987-09-03 Publication of JPS6241657B2 publication Critical patent/JPS6241657B2/ja

Status Granted legal-status Critical Current

Links

MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 40
-1 aromatic carbonyl compound Chemical class 0.000 claims description 20
150000001879 copper Chemical class 0.000 claims description 18
150000002505 iron Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims description 8
238000000354 decomposition reaction Methods 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
239000011261 inert gas Substances 0.000 claims description 4
150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 34
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 17
239000010410 layer Substances 0.000 description 13
239000011790 ferrous sulphate Substances 0.000 description 11
235000003891 ferrous sulphate Nutrition 0.000 description 11
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
229910000359 iron(II) sulfate Inorganic materials 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
229910000365 copper sulfate Inorganic materials 0.000 description 8
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 8
150000002432 hydroperoxides Chemical class 0.000 description 8
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
159000000014 iron salts Chemical class 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 5
MNEFLNSJCTVLTJ-UHFFFAOYSA-N 1-[3-(2-hydroxypropan-2-yl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C(C)(C)O)=C1 MNEFLNSJCTVLTJ-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
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 4
229910000360 iron(III) sulfate Inorganic materials 0.000 description 4
238000007086 side reaction Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000010949 copper Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
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 2
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
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000014413 iron hydroxide Nutrition 0.000 description 2
229910000358 iron sulfate Inorganic materials 0.000 description 2
NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000000276 potassium ferrocyanide Substances 0.000 description 2
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 2
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 1
GAEYNZPUAJMOJP-UHFFFAOYSA-N 1,2-diethylbenzene hydrogen peroxide Chemical compound OO.CCC1=CC=CC=C1CC GAEYNZPUAJMOJP-UHFFFAOYSA-N 0.000 description 1
LVQFKRXRTXCQCZ-UHFFFAOYSA-N 1-(2-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1C(C)=O LVQFKRXRTXCQCZ-UHFFFAOYSA-N 0.000 description 1
VCHOFVSNWYPAEF-UHFFFAOYSA-N 1-(3-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(C(C)=O)=C1 VCHOFVSNWYPAEF-UHFFFAOYSA-N 0.000 description 1
YNVZDODIHZTHOZ-UHFFFAOYSA-K 2-hydroxypropanoate;iron(3+) Chemical compound [Fe+3].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O YNVZDODIHZTHOZ-UHFFFAOYSA-K 0.000 description 1
HEOVGVNITGAUKL-UHFFFAOYSA-N 3-Methyl-1-phenyl-1-butanone Chemical compound CC(C)CC(=O)C1=CC=CC=C1 HEOVGVNITGAUKL-UHFFFAOYSA-N 0.000 description 1
FKSAYGREWVVCIZ-UHFFFAOYSA-N 3-methyl-1-phenylbut-3-en-1-one Chemical compound CC(=C)CC(=O)C1=CC=CC=C1 FKSAYGREWVVCIZ-UHFFFAOYSA-N 0.000 description 1
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
239000005750 Copper hydroxide Substances 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229910001956 copper hydroxide Inorganic materials 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 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
238000002474 experimental method Methods 0.000 description 1
VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
AQIRXGQDSUUKQA-UHFFFAOYSA-N hydrogen peroxide;4-methylpentan-2-one Chemical compound OO.CC(C)CC(C)=O AQIRXGQDSUUKQA-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-N iron;hydrochloride Chemical compound Cl.[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 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
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
239000008096 xylene 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

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

JP57140658A 1982-01-07 1982-08-12 芳香族カルボニル化合物の製造方法 Granted JPS5929632A (ja)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
JP57140658A JPS5929632A (ja)	1982-08-12	1982-08-12	芳香族カルボニル化合物の製造方法
DE8383300093T DE3363309D1 (en)	1982-01-07	1983-01-07	Production of aromatic carbonyl compounds including novel acetophenones
EP83300093A EP0084417B1 (de)	1982-01-07	1983-01-07	Herstellung von aromatischen Carbonylverbindungen sowie Azetophenonen
US06/456,455 US4486605A (en)	1982-01-07	1983-01-07	Method for producing aromatic carbonyl compounds

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57140658A JPS5929632A (ja)	1982-08-12	1982-08-12	芳香族カルボニル化合物の製造方法

Publications (2)

Publication Number	Publication Date
JPS5929632A JPS5929632A (ja)	1984-02-16
JPS6241657B2 true JPS6241657B2 (de)	1987-09-03

Family

ID=15273756

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57140658A Granted JPS5929632A (ja)	1982-01-07	1982-08-12	芳香族カルボニル化合物の製造方法

Country Status (1)

Country	Link
JP (1)	JPS5929632A (de)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS495324A (de) *	1972-04-29	1974-01-18
JPS5040537A (de) *	1973-05-28	1975-04-14

1982
- 1982-08-12 JP JP57140658A patent/JPS5929632A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS495324A (de) *	1972-04-29	1974-01-18
JPS5040537A (de) *	1973-05-28	1975-04-14

Also Published As

Publication number	Publication date
JPS5929632A (ja)	1984-02-16

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