US3857894A - Hydrogenation of cyclic hydrocarbon diolefins to cyclic hydrocarbon olefins - Google Patents
Hydrogenation of cyclic hydrocarbon diolefins to cyclic hydrocarbon olefins Download PDFInfo
- Publication number
- US3857894A US3857894A US00382055A US38205573A US3857894A US 3857894 A US3857894 A US 3857894A US 00382055 A US00382055 A US 00382055A US 38205573 A US38205573 A US 38205573A US 3857894 A US3857894 A US 3857894A
- Authority
- US
- United States
- Prior art keywords
- cyclic hydrocarbon
- zinc
- diolefin
- hydrogenation
- hydrogenating
- Prior art date
- 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
Links
- -1 cyclic hydrocarbon diolefins Chemical class 0.000 title claims description 40
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000003751 zinc Chemical class 0.000 claims abstract description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 239000011701 zinc Substances 0.000 claims abstract description 5
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 5
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001993 dienes Chemical class 0.000 claims abstract description 3
- 239000004246 zinc acetate Substances 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 2
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 2
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 5
- 150000001336 alkenes Chemical class 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 10
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000975 co-precipitation Methods 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 229920006395 saturated elastomer Chemical class 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HSQZKZLSYKJDJR-UHFFFAOYSA-N cyclopentane cyclopentene Chemical compound C1CCCC1.C1CC=CC1 HSQZKZLSYKJDJR-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical class [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
-
- 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
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
-
- 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
- C07C2527/138—Compounds comprising a halogen and an alkaline earth metal, magnesium, beryllium, zinc, cadmium or mercury
-
- 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
- C07C2527/24—Nitrogen compounds
- C07C2527/25—Nitrates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
Definitions
- the present invention relates to a process for the selective hydrogenation of diolefin hydrocarbons to olefin hyrdocarbons.
- the passage of I material to be hydrogenated and zinc salt on the catalyst in the course of the continuous tests can be effected for many times while obtaining always very good selectivity.
- the anion ofthe zinc salt has no importance as to the selectivity, but it is preferable that the salt have a high solubility in water.
- the chloride, sulfate, nitrate, acetate and oxalate are quite suitable.
- the amount of salt can vary from 0.0] to 5 percent and preferably from 0.01 to 2 percent by weight with respect to the diolefin compound.
- the minimum amount of water necessary for the good course of the reaction is such as to be sufficient to dissolve the zinc salt under the reaction conditions.
- an amine compound generally ammonia, in very low amounts, preferably lower than 0.5% by weight with respect to the diolefin compound, even though higher amounts, up to 20 30 percent do not negatively effect the reaction.
- the present invention can be applied to continuous or discontinuous processes in a wide range of tempera-- ture, for instance, between 20C and 60 instance C, and 0t izrsss tstfqriastanse f m. U9 .ZQW Q Phq It is to be noted that the amount of the salt, which is to be added to the reaction mixture, depends, within the abovementioned ranges, the reaction rate, i.e., on the hydrogen pressure and the temperature, and also on the efficacy of stirring.
- the absorption of hydrogen from the reaction mixture stops after one of the double-bonds has been hydrogenated to a simple bond, then, by letting the reacted mixture at the reaction conditions also for relatively long times, a further hydrogenation does not substantially occur.
- Cyclopentadiene was hydrogenated in the presence of 2 percent by weight of a Pd base catalyst on CaCO as catalyst carrier (5% Pd) at the temperature of 30C.
- 0.2 percent of ammonia, 0.2 percent of dehydrated zinc acetate and 0.4 percent by weight of water were added into an autoclave kept under stirring by means of a stirrer consisting of a hallow shaft for letting hydrogen be recirculated.
- the hydrogen pressure was 5 kg/cm
- the course of reaction was controlled by gaschromatography analysis performed on samples drawn at regular intervals.
- EXAMPLE 2 We operated according to'example l but the water amount was l percent. After the disappearance of starting cyclopentadiene, the selectivity as cyclopentene of the obtained product was 99.2 percent and'was practically constant also after a long time during which the product remained at the reaction conditions.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/537,378 US3947510A (en) | 1972-07-27 | 1974-12-30 | Hydrogenation of linear hydrocarbon diolefins to linear hydrocarbon olefins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT27492/72A IT963424B (it) | 1972-07-27 | 1972-07-27 | Processo di idrogenazione di idro carburi diolefinici a idrocarburi olefinici |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/537,378 Division US3947510A (en) | 1972-07-27 | 1974-12-30 | Hydrogenation of linear hydrocarbon diolefins to linear hydrocarbon olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3857894A true US3857894A (en) | 1974-12-31 |
Family
ID=11221753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00382055A Expired - Lifetime US3857894A (en) | 1972-07-27 | 1973-07-24 | Hydrogenation of cyclic hydrocarbon diolefins to cyclic hydrocarbon olefins |
Country Status (30)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947510A (en) * | 1972-07-27 | 1976-03-30 | Snamprogetti S.P.A. | Hydrogenation of linear hydrocarbon diolefins to linear hydrocarbon olefins |
| US4167529A (en) * | 1977-11-11 | 1979-09-11 | The Goodyear Tire & Rubber Company | Selective hydrogenation of cyclopentadiene to form cyclopentene using Raney nickel catalyst and ammonium hydroxide in the reaction mixture |
| US4570025A (en) * | 1985-06-14 | 1986-02-11 | Phillips Petroleum Company | Preparation of alkenes and cycloalkenes |
| US4906602A (en) * | 1987-10-28 | 1990-03-06 | Sud-Chemie Aktiengesellschaft | Catalyst for the selective hydrogenation of polyunsaturated hydrocarbons and process for preparing the catalyst |
| US6620982B1 (en) | 1998-10-07 | 2003-09-16 | Equistar Chemicals, Lp | Method of producing purified cyclopentane |
| CN106694010A (zh) * | 2016-12-27 | 2017-05-24 | 重庆建峰工业集团有限公司 | 一种用于炔醇半加氢制烯醇的催化剂及其制备方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI66019C (fi) * | 1977-12-19 | 1984-08-10 | Unilever Nv | Foerfarande foer selektiv hydrering av triglyceridolja |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2456633A (en) * | 1946-11-29 | 1948-12-21 | Universal Oil Prod Co | Catalyst preparation |
| US2728713A (en) * | 1952-09-25 | 1955-12-27 | Exxon Research Engineering Co | High activity reforming catalysts for use in the hydroforming of naphtha |
| US3369052A (en) * | 1963-10-29 | 1968-02-13 | Geigy Chem Corp | Production of cyclic alkene |
| US3408415A (en) * | 1965-09-20 | 1968-10-29 | Uniroyal Inc | Catalytic hydrogenation |
| US3418386A (en) * | 1966-07-05 | 1968-12-24 | Columbian Carbon | Hydrogenation of cyclooctadienes to cyclooctenes |
| US3433842A (en) * | 1967-04-12 | 1969-03-18 | Universal Oil Prod Co | Process for the hydrogenation of trans,cis-1,5-cyclodecadiene to ciscyclodecene |
| US3433843A (en) * | 1967-10-09 | 1969-03-18 | Universal Oil Prod Co | Selective hydrogenation of trans,cis-1,5-cyclodecadiene to cis-cyclodecene |
| US3715404A (en) * | 1964-06-03 | 1973-02-06 | Hoffmann La Roche | Process for selective hydrogenation |
| US3751497A (en) * | 1970-05-25 | 1973-08-07 | Bayer Ag | Process for the production of cyclopentene from cyclopentadiene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1323307A (fr) * | 1962-05-21 | 1963-04-05 | Basf Ag | Hydrogénation partielle de composés cycloaliphatiques renfermant au moins deux doubles liaisons oléfiniques |
-
1972
- 1972-07-27 IT IT27492/72A patent/IT963424B/it active
-
1973
- 1973-06-20 ZA ZA734155A patent/ZA734155B/xx unknown
- 1973-06-26 ZM ZM105/73*UA patent/ZM10573A1/xx unknown
- 1973-06-26 CS CS4591A patent/CS176241B2/cs unknown
- 1973-06-26 YU YU1719/73A patent/YU35092B/xx unknown
- 1973-06-27 RO RO7375259A patent/RO70140A/ro unknown
- 1973-06-28 AU AU57469/73A patent/AU477097B2/en not_active Expired
- 1973-07-05 JP JP7533473A patent/JPS5313602B2/ja not_active Expired
- 1973-07-05 TR TR17413A patent/TR17413A/xx unknown
- 1973-07-16 IE IE1194/73A patent/IE38478B1/xx unknown
- 1973-07-17 BG BG024125A patent/BG21008A3/xx unknown
- 1973-07-17 GB GB3408373A patent/GB1428287A/en not_active Expired
- 1973-07-18 IN IN1682/CAL/73A patent/IN139205B/en unknown
- 1973-07-18 CH CH1052073A patent/CH588428A5/xx not_active IP Right Cessation
- 1973-07-20 FR FR7326822A patent/FR2194672B1/fr not_active Expired
- 1973-07-24 BE BE133808A patent/BE802721A/xx unknown
- 1973-07-24 ES ES417524A patent/ES417524A1/es not_active Expired
- 1973-07-24 US US00382055A patent/US3857894A/en not_active Expired - Lifetime
- 1973-07-25 DD DD172509A patent/DD104500A5/xx unknown
- 1973-07-25 BR BR5591/73A patent/BR7305591D0/pt unknown
- 1973-07-26 CA CA177,367A patent/CA1046535A/en not_active Expired
- 1973-07-26 NO NO3023/73A patent/NO139858C/no unknown
- 1973-07-26 AT AT658773A patent/AT328417B/de not_active IP Right Cessation
- 1973-07-26 HU HU73SA00002513A patent/HU172415B/hu unknown
- 1973-07-26 NL NLAANVRAGE7310423,A patent/NL169724C/xx not_active IP Right Cessation
- 1973-07-26 LU LU68103A patent/LU68103A1/xx unknown
- 1973-07-26 DK DK414073AA patent/DK136524B/da not_active IP Right Cessation
- 1973-07-26 PL PL1973164309A patent/PL90383B1/pl unknown
- 1973-07-26 SE SE7310415A patent/SE379533B/xx unknown
- 1973-10-17 AR AR249129A patent/AR227263A1/es active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2456633A (en) * | 1946-11-29 | 1948-12-21 | Universal Oil Prod Co | Catalyst preparation |
| US2728713A (en) * | 1952-09-25 | 1955-12-27 | Exxon Research Engineering Co | High activity reforming catalysts for use in the hydroforming of naphtha |
| US3369052A (en) * | 1963-10-29 | 1968-02-13 | Geigy Chem Corp | Production of cyclic alkene |
| US3715404A (en) * | 1964-06-03 | 1973-02-06 | Hoffmann La Roche | Process for selective hydrogenation |
| US3408415A (en) * | 1965-09-20 | 1968-10-29 | Uniroyal Inc | Catalytic hydrogenation |
| US3418386A (en) * | 1966-07-05 | 1968-12-24 | Columbian Carbon | Hydrogenation of cyclooctadienes to cyclooctenes |
| US3433842A (en) * | 1967-04-12 | 1969-03-18 | Universal Oil Prod Co | Process for the hydrogenation of trans,cis-1,5-cyclodecadiene to ciscyclodecene |
| US3433843A (en) * | 1967-10-09 | 1969-03-18 | Universal Oil Prod Co | Selective hydrogenation of trans,cis-1,5-cyclodecadiene to cis-cyclodecene |
| US3751497A (en) * | 1970-05-25 | 1973-08-07 | Bayer Ag | Process for the production of cyclopentene from cyclopentadiene |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947510A (en) * | 1972-07-27 | 1976-03-30 | Snamprogetti S.P.A. | Hydrogenation of linear hydrocarbon diolefins to linear hydrocarbon olefins |
| US4167529A (en) * | 1977-11-11 | 1979-09-11 | The Goodyear Tire & Rubber Company | Selective hydrogenation of cyclopentadiene to form cyclopentene using Raney nickel catalyst and ammonium hydroxide in the reaction mixture |
| US4570025A (en) * | 1985-06-14 | 1986-02-11 | Phillips Petroleum Company | Preparation of alkenes and cycloalkenes |
| US4906602A (en) * | 1987-10-28 | 1990-03-06 | Sud-Chemie Aktiengesellschaft | Catalyst for the selective hydrogenation of polyunsaturated hydrocarbons and process for preparing the catalyst |
| US6620982B1 (en) | 1998-10-07 | 2003-09-16 | Equistar Chemicals, Lp | Method of producing purified cyclopentane |
| CN106694010A (zh) * | 2016-12-27 | 2017-05-24 | 重庆建峰工业集团有限公司 | 一种用于炔醇半加氢制烯醇的催化剂及其制备方法 |
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