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
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 13
- 150000001345 alkine derivatives Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 abstract description 15
- 239000003054 catalyst Substances 0.000 abstract description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 18
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- 150000000475 acetylene derivatives Chemical class 0.000 description 8
- 150000001993 dienes Chemical class 0.000 description 7
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 conjugated diolefins Chemical class 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical class CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004858 feed analysis Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 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
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052572 stoneware Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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 (enrdf_load_stackoverflow) | 1970-04-27 | 1971-11-01 | |
| JP46086311A JPS4852704A (enrdf_load_stackoverflow) | 1970-04-27 | 1971-11-01 | |
| DE2155400A DE2155400A1 (de) | 1970-04-27 | 1971-11-08 | Selektive hydrierung von alkinen |
| FR7140781A FR2161136A5 (enrdf_load_stackoverflow) | 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 (enrdf_load_stackoverflow) |
| JP (1) | JPS4852704A (enrdf_load_stackoverflow) |
| BE (1) | BE775275A (enrdf_load_stackoverflow) |
| CA (1) | CA956655A (enrdf_load_stackoverflow) |
| DE (1) | DE2155400A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2161136A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1338268A (enrdf_load_stackoverflow) |
| NL (1) | NL7115019A (enrdf_load_stackoverflow) |
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 (3)
| 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 |
| EP0479753B1 (en) * | 1990-10-04 | 1999-09-01 | Fina Technology, Inc. | Process for reduction of the phenylacetylene contaminants in styrene |
| RU2180611C1 (ru) * | 2000-12-26 | 2002-03-20 | Институт катализа им. Г.К. Борескова СО РАН | Катализатор и способ селективного гидрирования ацетиленовых углеводородов |
-
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 (12)
| 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 |
| RU2274631C2 (ru) * | 2001-04-18 | 2006-04-20 | Юоп Ллк | Способ очистки и получения потока диолефиновых углеводородов |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2155400A1 (de) | 1973-05-17 |
| JPS4852704A (enrdf_load_stackoverflow) | 1973-07-24 |
| FR2161136A5 (enrdf_load_stackoverflow) | 1973-07-06 |
| GB1338268A (en) | 1973-11-21 |
| CA956655A (en) | 1974-10-22 |
| NL7115019A (enrdf_load_stackoverflow) | 1973-05-03 |
| BE775275A (fr) | 1972-05-12 |
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