JPH0219097B2 - - Google Patents

Info

Publication number: JPH0219097B2
Authority: JP; Japan
Prior art keywords: alcohol; water; amount; catalyst; alcohols
Prior art date: 1984-08-10
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

JP59166605A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6144830A (ja

Inventor

Hajime Nagahara

Yohei Fukuoka

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.)

Asahi Chemical Industry Co Ltd

Original Assignee

Asahi Chemical Industry 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.)

1984-08-10

Filing date

1984-08-10

Publication date

1990-04-27

1984-08-10 Application filed by Asahi Chemical Industry Co Ltd filed Critical Asahi Chemical Industry Co Ltd

1984-08-10 Priority to JP59166605A priority Critical patent/JPS6144830A/ja

1986-03-04 Publication of JPS6144830A publication Critical patent/JPS6144830A/ja

1990-04-27 Publication of JPH0219097B2 publication Critical patent/JPH0219097B2/ja

Status Granted legal-status Critical Current

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
239000003054 catalyst Substances 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 16
-1 monocyclic aromatic hydrocarbons Chemical class 0.000 claims description 16
150000003752 zinc compounds Chemical class 0.000 claims description 14
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 12
229910052707 ruthenium Inorganic materials 0.000 claims description 12
239000000654 additive Substances 0.000 claims description 11
239000007791 liquid phase Substances 0.000 claims description 9
239000002994 raw material Substances 0.000 claims description 8
238000005984 hydrogenation reaction Methods 0.000 claims description 6
239000012071 phase Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 18
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 14
238000000034 method Methods 0.000 description 11
150000001298 alcohols Chemical class 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
150000003839 salts Chemical class 0.000 description 7
239000011787 zinc oxide Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000001934 cyclohexanes Chemical class 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
150000001935 cyclohexenes Chemical class 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
230000000737 periodic effect Effects 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000006757 chemical reactions by type Methods 0.000 description 1
150000003841 chloride salts Chemical class 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
YXEUGTSPQFTXTR-UHFFFAOYSA-K lanthanum(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[La+3] YXEUGTSPQFTXTR-UHFFFAOYSA-K 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
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
HVTHJRMZXBWFNE-UHFFFAOYSA-J sodium zincate Chemical compound [OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Zn+2] HVTHJRMZXBWFNE-UHFFFAOYSA-J 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000725 suspension Substances 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229940006486 zinc cation Drugs 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 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)

JP59166605A 1984-08-10 1984-08-10 シクロオレフインの製造方法 Granted JPS6144830A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP59166605A JPS6144830A (ja)	1984-08-10	1984-08-10	シクロオレフインの製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59166605A JPS6144830A (ja)	1984-08-10	1984-08-10	シクロオレフインの製造方法

Publications (2)

Publication Number	Publication Date
JPS6144830A JPS6144830A (ja)	1986-03-04
JPH0219097B2 true JPH0219097B2 (uk)	1990-04-27

Family

ID=15834394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59166605A Granted JPS6144830A (ja)	1984-08-10	1984-08-10	シクロオレフインの製造方法

Country Status (1)

Country	Link
JP (1)	JPS6144830A (uk)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51128939A (en) *	1975-05-06	1976-11-10	Mitsubishi Chem Ind Ltd	Process for preparing cycloolefins
JPS5363350A (en) *	1976-11-17	1978-06-06	Toray Ind Inc	Preparation of cyclohexenes
JPS5427540A (en) *	1977-08-01	1979-03-01	Toray Ind Inc	Preparation of cycloolefin
JPS57134422A (en) *	1980-12-31	1982-08-19	Stamicarbon	Manufacture of cycloalkene by partial hydrogenation of corresponding aromatic hydrocarbons

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2885794B2 (ja) *	1987-07-24	1999-04-26	松下電器産業株式会社	速度変調用信号発生回路

1984
- 1984-08-10 JP JP59166605A patent/JPS6144830A/ja active Granted

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51128939A (en) *	1975-05-06	1976-11-10	Mitsubishi Chem Ind Ltd	Process for preparing cycloolefins
JPS5363350A (en) *	1976-11-17	1978-06-06	Toray Ind Inc	Preparation of cyclohexenes
JPS5427540A (en) *	1977-08-01	1979-03-01	Toray Ind Inc	Preparation of cycloolefin
JPS57134422A (en) *	1980-12-31	1982-08-19	Stamicarbon	Manufacture of cycloalkene by partial hydrogenation of corresponding aromatic hydrocarbons

Also Published As

Publication number	Publication date
JPS6144830A (ja)	1986-03-04

Legal Events

Date	Code	Title	Description
2004-08-10	EXPY	Cancellation because of completion of term

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