US3634536A - Selective hydrogenation of alkynes - Google Patents
Selective hydrogenation of alkynes Download PDFInfo
- Publication number
- US3634536A US3634536A US32378A US3634536DA US3634536A US 3634536 A US3634536 A US 3634536A US 32378 A US32378 A US 32378A US 3634536D A US3634536D A US 3634536DA US 3634536 A US3634536 A US 3634536A
- Authority
- US
- United States
- Prior art keywords
- percent
- butadiene
- selective hydrogenation
- acetylenic
- hydrogenation
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
-
- 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
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/72—Copper
Definitions
- the catalytic hydrogenation conditions and catalysts generally suitable for the method of this invention are detailed in US. Pat. 2,426,604 (1947), the specification of which is hereby expressly incorporated by reference.
- the streams which are suitable herein as feeds comprise those which contain isoprene or butadiene-1,3, and other hydrocarbons, such as isobutane, isobutylene, n-butylene- 1, n butane and n-butylene-2; up to 1 weight percent of C acetylenic compounds, such as acetylene, methylacetylene, vinylacetylene, ethylacetylene, and the like; and, other hydrocarbon compounds such as alkanes and cycloalkanes, such as n-pentane, isopentane, neopentane, cyclohexane, and the like.
- the catalysts which are suitable for the process of this invention are prepared so as to contain between and 99.9 (preferably between and 97) percent by weight of copper and between 15 and 0.1 (preferably between 10 and 3) percent of another metal, the oxide of which is reducible to a lower valence state with hydrogen at temperatures below 550 C.
- metals include chromium, cobalt, manganese, nickel, vanadium, titanium, molybdenum, cadmium, zinc, silver, and the like, and also mixtures of such metals.
- the catalysts are preferably employed in dispersed form on a substantially inert carrier material such as aluminum silicate, brick, stoneware, pumice, porous silica, and the like.
- a substantially inert carrier material such as aluminum silicate, brick, stoneware, pumice, porous silica, and the like.
- this supported catalyst is prepared so as to contain from 10 to 30 percent by weight of the mixture of metals, but it may contain such metals in smaller or greater proportions.
- the above incorporated patent includes detailed instructions as to the various methods of preparing said catalyst.
- reaction conditions which are most suited for the method of this invention involve generally a 4 to 7 (preferably about 6) fold excess of hydrogen with respect to the concentration of acetylenes in the feed, and a space velocity of 300-1000, preferably about 600.
- the reactor was a glass tube (1.5 centimeters ID. by 10.5 centimeters long) with a 3 millimeter O.D. thermocouple well centered concentrically the length of the tube.
- the internal volume of the reactor was 18.5 milliliters. It was loaded with 9.827 grams of catalyst.
- the catalyst contained 14 weight percent copper and 0.7 weight percent nickel on a siliceous support.
- the reactor tube was inserted into a thermostatic heating unit, and the reactor brought to the indicated temperature.
- the feed stream ' was vaporized and mixed with hydrogen and carbon monoxide, and the mixture passed through the heated reactor.
- the efiiuent was condensed in a Dry Ice trap, the condensate being analyzed by gas liquid chromatography.
- acetylene concentration in the efliuent was generally about 5 times greater when the CO was not present during hydrogenation, concentrations as low as 7 p.p.m. being realized with the addition of CO.
- An isoprene-containing stream would have the acetylenic impurities therein selectively hydrogenated similarly as above.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3237870A | 1970-04-27 | 1970-04-27 | |
CA124,816A CA956655A (en) | 1970-04-27 | 1971-10-08 | Selective hydrogenation of alkynes |
GB4926971A GB1338268A (en) | 1970-04-27 | 1971-10-22 | Selective hydrogenation of alkynes |
NL7115019A NL7115019A (xx) | 1970-04-27 | 1971-11-01 | |
JP46086311A JPS4852704A (xx) | 1970-04-27 | 1971-11-01 | |
DE2155400A DE2155400A1 (de) | 1970-04-27 | 1971-11-08 | Selektive hydrierung von alkinen |
FR7140781A FR2161136A5 (xx) | 1970-04-27 | 1971-11-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3634536A true US3634536A (en) | 1972-01-11 |
Family
ID=27560858
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US32378A Expired - Lifetime US3634536A (en) | 1970-04-27 | 1970-04-27 | Selective hydrogenation of alkynes |
Country Status (8)
Country | Link |
---|---|
US (1) | US3634536A (xx) |
JP (1) | JPS4852704A (xx) |
BE (1) | BE775275A (xx) |
CA (1) | CA956655A (xx) |
DE (1) | DE2155400A1 (xx) |
FR (1) | FR2161136A5 (xx) |
GB (1) | GB1338268A (xx) |
NL (1) | NL7115019A (xx) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3887632A (en) * | 1972-10-11 | 1975-06-03 | Alexandr Grigoriev Liakumovich | Process for purifying diene hydrocarbons from acetylene hydrocarbon contaminants |
US4053533A (en) * | 1975-10-15 | 1977-10-11 | Phillips Petroleum Company | Oxidation of acetylenic impurities with copper manganite catalyst |
US4064190A (en) * | 1976-12-17 | 1977-12-20 | Phillips Petroleum Company | Removal of acetylenic contaminants by copper-tin and/or lead zinc aluminate |
US4251674A (en) * | 1979-10-22 | 1981-02-17 | Phillips Petroleum Company | Method and apparatus for improving the selectivity of a process for hydrogenating acetylene to ethylene |
US4705906A (en) * | 1985-11-27 | 1987-11-10 | The British Petroleum Company, P.L.C. | Selective hydrogenation of acetylene |
US4822936A (en) * | 1987-08-25 | 1989-04-18 | The Dow Chemical Company | Selective hydrogenation of phenylacetylene in the presence of styrene |
EP1070695A1 (en) * | 1999-07-22 | 2001-01-24 | Uop Llc | A process for the purification of a diolefin hydrocarbon stream |
US6194626B1 (en) | 1999-12-06 | 2001-02-27 | Uop Llc | Process for the purification of a diolefin hydrocarbon stream from a naphtha steam cracker |
US6225515B1 (en) | 1999-07-22 | 2001-05-01 | Uop Llc | Process for the purification of a diolefin hydrocarbon stream |
US6512151B2 (en) | 2001-04-18 | 2003-01-28 | Uop Llc | Process for the purification and production of a diolefin hydrocarbon stream |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5959634A (ja) * | 1982-09-27 | 1984-04-05 | Mitsui Petrochem Ind Ltd | アセチレンの選択的水添方法 |
DE69131567T2 (de) * | 1990-10-04 | 2000-05-18 | Fina Technology, Inc. | Verfahren zur Reduktion von Phenylacetylen-Verunreinigungen in Styrol |
-
1970
- 1970-04-27 US US32378A patent/US3634536A/en not_active Expired - Lifetime
-
1971
- 1971-10-08 CA CA124,816A patent/CA956655A/en not_active Expired
- 1971-10-22 GB GB4926971A patent/GB1338268A/en not_active Expired
- 1971-11-01 JP JP46086311A patent/JPS4852704A/ja active Pending
- 1971-11-01 NL NL7115019A patent/NL7115019A/xx unknown
- 1971-11-08 DE DE2155400A patent/DE2155400A1/de active Pending
- 1971-11-12 BE BE775275A patent/BE775275A/xx unknown
- 1971-11-15 FR FR7140781A patent/FR2161136A5/fr not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3887632A (en) * | 1972-10-11 | 1975-06-03 | Alexandr Grigoriev Liakumovich | Process for purifying diene hydrocarbons from acetylene hydrocarbon contaminants |
US4053533A (en) * | 1975-10-15 | 1977-10-11 | Phillips Petroleum Company | Oxidation of acetylenic impurities with copper manganite catalyst |
US4064190A (en) * | 1976-12-17 | 1977-12-20 | Phillips Petroleum Company | Removal of acetylenic contaminants by copper-tin and/or lead zinc aluminate |
US4251674A (en) * | 1979-10-22 | 1981-02-17 | Phillips Petroleum Company | Method and apparatus for improving the selectivity of a process for hydrogenating acetylene to ethylene |
US4705906A (en) * | 1985-11-27 | 1987-11-10 | The British Petroleum Company, P.L.C. | Selective hydrogenation of acetylene |
US4822936A (en) * | 1987-08-25 | 1989-04-18 | The Dow Chemical Company | Selective hydrogenation of phenylacetylene in the presence of styrene |
EP1070695A1 (en) * | 1999-07-22 | 2001-01-24 | Uop Llc | A process for the purification of a diolefin hydrocarbon stream |
US6225515B1 (en) | 1999-07-22 | 2001-05-01 | Uop Llc | Process for the purification of a diolefin hydrocarbon stream |
US6271428B1 (en) | 1999-07-22 | 2001-08-07 | Uop Llc | Process for the purification of a diolefin hydrocarbon stream |
US6194626B1 (en) | 1999-12-06 | 2001-02-27 | Uop Llc | Process for the purification of a diolefin hydrocarbon stream from a naphtha steam cracker |
US6512151B2 (en) | 2001-04-18 | 2003-01-28 | Uop Llc | Process for the purification and production of a diolefin hydrocarbon stream |
Also Published As
Publication number | Publication date |
---|---|
DE2155400A1 (de) | 1973-05-17 |
GB1338268A (en) | 1973-11-21 |
CA956655A (en) | 1974-10-22 |
FR2161136A5 (xx) | 1973-07-06 |
BE775275A (fr) | 1972-05-12 |
JPS4852704A (xx) | 1973-07-24 |
NL7115019A (xx) | 1973-05-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4517395A (en) | Process for the selective hydrogenation of polyunsaturated hydrocarbons in hydrocarbon mixtures | |
US3634536A (en) | Selective hydrogenation of alkynes | |
US3200167A (en) | Process for the removal of acetylenic hydrocarbons by selective catalyst hydrogenation | |
CN103052613B (zh) | 含烯烃的烃混合物中多重不饱和烃的选择性氢化方法 | |
US3662015A (en) | Method of preventing double bond migration of mono-olefinic hydrocarbons in selective hydrogenation | |
US3098882A (en) | Selective hydrogenation procedure and catalyst therefor | |
WO2001023087A1 (en) | Hydrocarbon hydrogenation catalyst and process | |
CA1058228A (en) | Recovery of 1,3-butadiene from a c4-hydrocarbon mixture | |
US2426604A (en) | Removal of acetylenic hydrocarbons from diolefine-containing mixtures | |
Koeppel et al. | Selective hydrogenation of C4-alkynes over a copper on silica catalyst | |
US3804916A (en) | Selective hydrogenation of alkynes or 1,3-conjugated dienes | |
US4658080A (en) | Acetylene removal process | |
US3003008A (en) | Selective hydrogenation of acetylenes in the presence of olefinic gases containing unsaturated c4 hydrocarbons | |
US4009126A (en) | Catalyst for removing acetylenic impurities | |
US4247725A (en) | Method of removing acetylenes from C4 -hydrocarbon mixture containing butadiene | |
US3743684A (en) | Catalyst,catalyst preparation method,and process for catalytic hydrotreating unsaturated hydrocarbons | |
US4036904A (en) | Isomerization of allenes in a hydrocarbon stream using magnesium oxide catalyst | |
EP1259319A1 (en) | Hydrocarbon hydrogenation catalyst and process | |
US4174355A (en) | Process for removing α-acetylenes from diolefins | |
US3505304A (en) | Production of polymer from low-purity conjugated diene monomer feed | |
JPS6325566B2 (xx) | ||
US4644088A (en) | Acetylene removal process | |
CA1142506A (en) | Hydrogenation catalyst | |
US3404101A (en) | Catalyst for selective hydrogenation of diolefinic and acetylenic hydrocarbons | |
US4266086A (en) | Process for removing α-acetylenes from diolefins |