SU489320A3 - Способ получени насыщенных карбо-или гетероциклических соединений - Google Patents

Способ получени насыщенных карбо-или гетероциклических соединений

Info

Publication number: SU489320A3
Authority: SU; USSR - Soviet Union
Prior art keywords: ruthenium; alumina; catalyst; heterocyclic compounds; ruthenium chloride
Prior art date: 1972-09-05

Application number

SU1957941A

Other languages

English (en)

Russian (ru)

Inventor

Луис Бенезра(Сша) Лео

Сантьяго Де Пабло(Аргентина) Рауль

Рандольф Осгуд(Сша) Эдмонд

Original Assignee

Даймонд Шамрок Корпорейшн (Фирма)

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.)

1972-09-05

Filing date

1973-09-04

Publication date

1975-10-25

1973-09-04 Application filed by Даймонд Шамрок Корпорейшн (Фирма) filed Critical Даймонд Шамрок Корпорейшн (Фирма)

1975-10-25 Application granted granted Critical

1975-10-25 Publication of SU489320A3 publication Critical patent/SU489320A3/ru

Links

238000000034 method Methods 0.000 title description 14
150000002391 heterocyclic compounds Chemical class 0.000 title description 7
229920006395 saturated elastomer Polymers 0.000 title description 7
150000001717 carbocyclic compounds Chemical class 0.000 title description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 17
239000003054 catalyst Substances 0.000 description 17
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 16
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 15
229910052707 ruthenium Inorganic materials 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
239000003518 caustics Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
239000012071 phase Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003303 ruthenium Chemical class 0.000 description 3
OUYLXVQKVBXUGW-UHFFFAOYSA-N 2,3-dimethyl-1h-pyrrole Chemical compound CC=1C=CNC=1C OUYLXVQKVBXUGW-UHFFFAOYSA-N 0.000 description 2
PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004821 distillation Methods 0.000 description 2
-1 for example Substances 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
238000011068 loading method Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000004445 quantitative analysis Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
HJDUCMRBFKTGNO-UHFFFAOYSA-N 2,5-dimethyl-3,4-dihydro-2h-pyrrole Chemical compound CC1CCC(C)=N1 HJDUCMRBFKTGNO-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000002101 lytic effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
- C07C2527/13—Platinum group metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Hydrogenated Pyridines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SU1957941A 1972-09-05 1973-09-04 Способ получени насыщенных карбо-или гетероциклических соединений SU489320A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US28609572A	1972-09-05	1972-09-05

Publications (1)

Publication Number	Publication Date
SU489320A3 true SU489320A3 (ru)	1975-10-25

Family

ID=23097048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1957941A SU489320A3 (ru)	1972-09-05	1973-09-04	Способ получени насыщенных карбо-или гетероциклических соединений

Country Status (11)

Country	Link
JP (1)	JPS4969631A (fr)
AU (1)	AU5991573A (fr)
BE (1)	BE804429A (fr)
DD (1)	DD106340A5 (fr)
DE (1)	DE2344509A1 (fr)
FR (1)	FR2197832B1 (fr)
GB (1)	GB1393659A (fr)
IT (1)	IT997527B (fr)
NL (1)	NL7312230A (fr)
SU (1)	SU489320A3 (fr)
ZA (1)	ZA736048B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2526782A1 (fr) *	1982-05-14	1983-11-18	Metaux Precieux Cie	Procede de preparation de chlorure de ruthenium et catalyseur obtenu a partir de ce chlorure
WO2007063974A1 (fr) *	2005-12-02	2007-06-07	Nagoya Industrial Science Research Institute	Procede pour hydrogener un cycle aromatique de compose cyclique aromatique

1973
- 1973-09-03 AU AU59915/73A patent/AU5991573A/en not_active Expired
- 1973-09-04 NL NL7312230A patent/NL7312230A/xx unknown
- 1973-09-04 GB GB4153573A patent/GB1393659A/en not_active Expired
- 1973-09-04 FR FR7331841A patent/FR2197832B1/fr not_active Expired
- 1973-09-04 DE DE19732344509 patent/DE2344509A1/de active Pending
- 1973-09-04 ZA ZA736048A patent/ZA736048B/xx unknown
- 1973-09-04 DD DD173269A patent/DD106340A5/xx unknown
- 1973-09-04 JP JP48098956A patent/JPS4969631A/ja active Pending
- 1973-09-04 BE BE135292A patent/BE804429A/fr unknown
- 1973-09-04 IT IT52331/73A patent/IT997527B/it active
- 1973-09-04 SU SU1957941A patent/SU489320A3/ru active

Also Published As

Publication number	Publication date
FR2197832B1 (fr)	1977-02-25
NL7312230A (fr)	1974-03-07
DD106340A5 (fr)	1974-06-12
BE804429A (fr)	1974-03-04
ZA736048B (en)	1974-10-30
AU5991573A (en)	1975-03-06
FR2197832A1 (fr)	1974-03-29
DE2344509A1 (de)	1974-03-21
GB1393659A (en)	1975-05-07
JPS4969631A (fr)	1974-07-05
IT997527B (it)	1975-12-30

Publication	Publication Date	Title
US4417077A (en)	1983-11-22	Heterogeneous anionic transition metal catalysts
US4105674A (en)	1978-08-08	Production of gamma-butyrolactone from maleic anhydride with a hydrogenation catalyst
JPS6332769B2 (fr)	1988-07-01
JPS6261577B2 (fr)	1987-12-22
DiMondo et al.	2013	Comparison of the Catalytic Activity of [(η5-C5H5) Ru (2, 2′-bipyridine)(L)] OTf versus [(η5-C5H5) Ru (6, 6′-diamino-2, 2′-bipyridine)(L)] OTf (L= labile ligand) in the Hydrogenation of Cyclohexanone. Evidence for the Presence of a Metal–Ligand Bifunctional Mechanism under Acidic Conditions
US4729977A (en)	1988-03-08	Supported catalyst, process for its preparation and its use for the preparation of hydroxydiphenyl
Tanaka et al.	1972	Catalytic Asymmetric Hydroformylation with a Chiral Phosphine–Rhodium Complex
JP2997596B2 (ja)	2000-01-11	ジフエニルアミン類の製造方法
US4476310A (en)	1984-10-09	Process for the preparation of indoles
RU2147298C1 (ru)	2000-04-10	Способ получения 1,4-бутандиола
JPS6233546A (ja)	1987-02-13	アルデヒドの脱水触媒及びアルデヒドのジエンへの転化方法
US4250093A (en)	1981-02-10	Process for the preparation of laotams
Pines et al.	1970	Hydrogenolysis of alcohols: II. Reduced nickel oxide—Its intrinsic acidity and catalytic activity in the conversion of alcohols to ethers
GB1593803A (en)	1981-07-22	Method of producing furfuryl alcohol
US4115463A (en)	1978-09-19	Production of cycloalkylaromatics
JP3266332B2 (ja)	2002-03-18	ヒドロキシジフエニル類の製造方法
JPH0410451B2 (fr)	1992-02-25
JPS6028429A (ja)	1985-02-13	ポリエチレングリコ−ルジアルキルエ−テル製造用触媒
JP2611184B2 (ja)	1997-05-21	二酸化炭素からエタノールを製造する方法及び製造用触媒
Ciardelli et al.	1985	Structure and reactivity of aromatic polymers ruthenium catalysts
US4174302A (en)	1979-11-13	Catalyst for production of cycloalkylaromatics
Meyers et al.	1985	Reactions of silica-alumina supported benzylidyne (nonacarbonyl) tricobalt under hydrogen, carbon monoxide, and synthesis gas
SU1109190A1 (ru)	1984-08-23	Способ получени катализатора дл гидрировани органических соединений
SU546608A1 (ru)	1977-02-15	Способ получени 2,4,4,-триминобензанилида
US5763717A (en)	1998-06-09	Process for preparing hydroxybiphenyl