JPH0535135B2 - - Google Patents

Info

Publication number: JPH0535135B2
Authority: JP; Japan
Prior art keywords: catalyst; titanium; reaction; same manner; ketone
Prior art date: 1986-02-13
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

JP61027874A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62187422A (ja

Inventor

Yutaka Morikawa

Tsuneo Ikawa

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.)

Idemitsu Kosan Co Ltd

Original Assignee

Idemitsu Kosan 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.)

1986-02-13

Filing date

1986-02-13

Publication date

1993-05-25

1986-02-13 Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd

1986-02-13 Priority to JP61027874A priority Critical patent/JPS62187422A/ja

1987-08-15 Publication of JPS62187422A publication Critical patent/JPS62187422A/ja

1993-05-25 Publication of JPH0535135B2 publication Critical patent/JPH0535135B2/ja

Status Granted legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 claims description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
239000010936 titanium Substances 0.000 claims description 16
229910052719 titanium Inorganic materials 0.000 claims description 14
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 13
150000001728 carbonyl compounds Chemical class 0.000 claims description 10
UTEKWVTZAYINIU-UHFFFAOYSA-N [F].[Si].[Si].[Si].[Si] Chemical group [F].[Si].[Si].[Si].[Si] UTEKWVTZAYINIU-UHFFFAOYSA-N 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
239000010445 mica Substances 0.000 claims description 9
229910052618 mica group Inorganic materials 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
150000003609 titanium compounds Chemical class 0.000 claims description 8
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 7
229910000271 hectorite Inorganic materials 0.000 claims description 7
150000002576 ketones Chemical class 0.000 claims description 7
239000004113 Sepiolite Substances 0.000 claims description 6
229910052624 sepiolite Inorganic materials 0.000 claims description 6
235000019355 sepiolite Nutrition 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
239000000741 silica gel Substances 0.000 claims description 5
229910002027 silica gel Inorganic materials 0.000 claims description 5
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 12
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 10
239000007789 gas Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
238000005342 ion exchange Methods 0.000 description 6
239000000843 powder Substances 0.000 description 6
235000005074 zinc chloride Nutrition 0.000 description 6
239000011592 zinc chloride Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
229940110728 nitrogen / oxygen Drugs 0.000 description 5
239000002994 raw material Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000011229 interlayer Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-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
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
229910001882 dioxygen Inorganic materials 0.000 description 2
230000000694 effects Effects 0.000 description 2
JTHNLKXLWOXOQK-UHFFFAOYSA-N hex-1-en-3-one Chemical compound CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 2
150000004687 hexahydrates Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
-1 taeniolite Inorganic materials 0.000 description 2
229910000348 titanium sulfate Inorganic materials 0.000 description 2
OYLCUJRJCUXQBQ-UHFFFAOYSA-N 1-hepten-3-one Chemical compound CCCCC(=O)C=C OYLCUJRJCUXQBQ-UHFFFAOYSA-N 0.000 description 1
PTUXNCQDACBMKP-UHFFFAOYSA-N 1-phenylbut-3-en-2-one Chemical compound C=CC(=O)CC1=CC=CC=C1 PTUXNCQDACBMKP-UHFFFAOYSA-N 0.000 description 1
KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
VYTPDQSCOXJDJM-UHFFFAOYSA-N 2-methylidenecyclohexan-1-one Chemical compound C=C1CCCCC1=O VYTPDQSCOXJDJM-UHFFFAOYSA-N 0.000 description 1
SLRKFRUSEKUSAF-UHFFFAOYSA-N 2-methylidenecyclopentan-1-one Chemical compound C=C1CCCC1=O SLRKFRUSEKUSAF-UHFFFAOYSA-N 0.000 description 1
PLRMBWBTVMZCAM-UHFFFAOYSA-N CC(=O)C=C.CC(=O)C=C Chemical compound CC(=O)C=C.CC(=O)C=C PLRMBWBTVMZCAM-UHFFFAOYSA-N 0.000 description 1
229910021555 Chromium Chloride Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
229910012506 LiSi Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000011651 chromium Substances 0.000 description 1
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000011572 manganese Substances 0.000 description 1
CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
239000000047 product Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000011701 zinc 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)

JP61027874A 1986-02-13 1986-02-13 α，β−エチレン性不飽和カルボニル化合物の製造方法 Granted JPS62187422A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP61027874A JPS62187422A (ja)	1986-02-13	1986-02-13	α，β−エチレン性不飽和カルボニル化合物の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP61027874A JPS62187422A (ja)	1986-02-13	1986-02-13	α，β−エチレン性不飽和カルボニル化合物の製造方法

Publications (2)

Publication Number	Publication Date
JPS62187422A JPS62187422A (ja)	1987-08-15
JPH0535135B2 true JPH0535135B2 (sk)	1993-05-25

Family

ID=12233041

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61027874A Granted JPS62187422A (ja)	1986-02-13	1986-02-13	α，β−エチレン性不飽和カルボニル化合物の製造方法

Country Status (1)

Country	Link
JP (1)	JPS62187422A (sk)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4980513A (en) *	1990-01-04	1990-12-25	Quantum Chemical Corporation	Process for making a hydrocarbyl vinyl ketone
US20210130513A1 (en) *	2019-11-01	2021-05-06	Chevron Phillips Chemical Company Lp	System and method for catalyst preparation

1986
- 1986-02-13 JP JP61027874A patent/JPS62187422A/ja active Granted

Also Published As

Publication number	Publication date
JPS62187422A (ja)	1987-08-15

Publication	Publication Date	Title
JPH04277030A (ja)	1992-10-02	エチルベンゼン脱水素触媒
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WO2007038371A1 (en)	2007-04-05	Catalysts selective for the preparation of mixed ketones from a mixture of carboxylic acids
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