JPH0152373B2 - - Google Patents

Info

Publication number: JPH0152373B2
Authority: JP; Japan
Prior art keywords: catalyst; palladium; reaction; cyclopentanol; cyclopentanone
Prior art date: 1982-03-03
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

JP57032272A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58150534A (ja

Inventor

Akihiko Niina

Ryoji Sato

Terutaka Yao

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.)

Zeon Corp

Original Assignee

Nippon Zeon 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.)

1982-03-03

Filing date

1982-03-03

Publication date

1989-11-08

1982-03-03 Application filed by Nippon Zeon Co Ltd filed Critical Nippon Zeon Co Ltd

1982-03-03 Priority to JP57032272A priority Critical patent/JPS58150534A/ja

1983-09-07 Publication of JPS58150534A publication Critical patent/JPS58150534A/ja

1989-11-08 Publication of JPH0152373B2 publication Critical patent/JPH0152373B2/ja

Status Granted legal-status Critical Current

Links

KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 36
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 28
239000003054 catalyst Substances 0.000 claims description 21
229910052763 palladium Inorganic materials 0.000 claims description 17
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 11
238000000034 method Methods 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 15
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000007789 gas Substances 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000012071 phase Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
238000006356 dehydrogenation reaction Methods 0.000 description 4
238000005342 ion exchange Methods 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000000576 coating method Methods 0.000 description 3
239000002184 metal Substances 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
239000002994 raw material Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
-1 alicyclic alcohols Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000003446 ligand Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000002941 palladium compounds Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
150000003333 secondary alcohols Chemical class 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
238000005406 washing Methods 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 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
150000004645 aluminates Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003575 carbonaceous material Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000006757 chemical reactions by type Methods 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
238000007872 degassing Methods 0.000 description 1
238000000151 deposition Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 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
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000008262 pumice Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010977 unit operation Methods 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

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

JP57032272A 1982-03-03 1982-03-03 シクロペンタノンの製造方法 Granted JPS58150534A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP57032272A JPS58150534A (ja)	1982-03-03	1982-03-03	シクロペンタノンの製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57032272A JPS58150534A (ja)	1982-03-03	1982-03-03	シクロペンタノンの製造方法

Publications (2)

Publication Number	Publication Date
JPS58150534A JPS58150534A (ja)	1983-09-07
JPH0152373B2 true JPH0152373B2 (zh)	1989-11-08

Family

ID=12354349

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57032272A Granted JPS58150534A (ja)	1982-03-03	1982-03-03	シクロペンタノンの製造方法

Country Status (1)

Country	Link
JP (1)	JPS58150534A (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2007084499A (ja) *	2005-09-26	2007-04-05	Kobe Univ	アルコール類の酸化方法
CN107935832A (zh) *	2017-12-30	2018-04-20	郑州智谷工业技术有限公司	一种利用醇脱氢制备醛或半缩醛的方法

1982
- 1982-03-03 JP JP57032272A patent/JPS58150534A/ja active Granted

Also Published As

Publication number	Publication date
JPS58150534A (ja)	1983-09-07

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Mallat et al.	2000	Selectivity enhancement in heterogeneous catalysis induced by reaction modifiers
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