JPS5829142B2 - 無水マレイン酸を液相水素化してγ−ブチロラクトンにするための触媒の製法 - Google Patents
無水マレイン酸を液相水素化してγ−ブチロラクトンにするための触媒の製法Info
- Publication number
- JPS5829142B2 JPS5829142B2 JP50074269A JP7426975A JPS5829142B2 JP S5829142 B2 JPS5829142 B2 JP S5829142B2 JP 50074269 A JP50074269 A JP 50074269A JP 7426975 A JP7426975 A JP 7426975A JP S5829142 B2 JPS5829142 B2 JP S5829142B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- butyrolactone
- maleic anhydride
- palladium
- impregnated
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims description 42
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title claims description 31
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims description 12
- 239000007791 liquid phase Substances 0.000 title claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- 229910052763 palladium Inorganic materials 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000012266 salt solution Substances 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001868 cobalt Chemical class 0.000 claims description 9
- 229910052681 coesite Inorganic materials 0.000 claims description 8
- 229910052906 cristobalite Inorganic materials 0.000 claims description 8
- 229910052682 stishovite Inorganic materials 0.000 claims description 8
- 229910052905 tridymite Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 235000012239 silicon dioxide Nutrition 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000002940 palladium Chemical class 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-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
- 239000007868 Raney catalyst Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8913—Cobalt and noble metals
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
- B01J35/51—Spheres
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2429085 | 1974-06-18 | ||
| DE2429085A DE2429085C3 (de) | 1974-06-18 | 1974-06-18 | Verfahren zur Herstellung eines Katalysators für die Flüssigphasenhydrierung von Maleinsäureanhydrid zu γ-Butyrolacton |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5114187A JPS5114187A (enExample) | 1976-02-04 |
| JPS5829142B2 true JPS5829142B2 (ja) | 1983-06-21 |
Family
ID=5918283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50074269A Expired JPS5829142B2 (ja) | 1974-06-18 | 1975-06-18 | 無水マレイン酸を液相水素化してγ−ブチロラクトンにするための触媒の製法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3994928A (enExample) |
| JP (1) | JPS5829142B2 (enExample) |
| BE (1) | BE830323A (enExample) |
| CA (1) | CA1041529A (enExample) |
| DE (1) | DE2429085C3 (enExample) |
| FR (1) | FR2275251A1 (enExample) |
| GB (1) | GB1466216A (enExample) |
| IT (1) | IT1038353B (enExample) |
| NL (1) | NL7506960A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2642533C2 (de) * | 1976-09-22 | 1985-08-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von gamma- Butyrolacton aus Maleinsäureanhydrid |
| JPS58123064A (ja) * | 1982-01-14 | 1983-07-22 | 三菱電機株式会社 | 自動車用空気調和装置 |
| US4810807A (en) * | 1987-10-13 | 1989-03-07 | The Standard Oil Company | Hydrogenation of maleic anhydride to tetrahydrofuran |
| GB8809587D0 (en) * | 1988-04-22 | 1988-05-25 | Ucb Sa | Process for making gamma-butyrolactone |
| US4968818A (en) * | 1989-08-03 | 1990-11-06 | Phillips Petroleum Company | Gamma-butyrolactone production process and catalyst therefor |
| US5086030A (en) * | 1989-08-03 | 1992-02-04 | Phillips Petroleum Company | Gamma-butyrolactone production catalyst |
| EP0543340B1 (en) * | 1991-11-18 | 1998-05-20 | Tosoh Corporation | Process for preparing lactones |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113138A (en) * | 1961-12-20 | 1963-12-03 | Fmc Corp | Preparation of butyrolactone |
-
1974
- 1974-06-18 DE DE2429085A patent/DE2429085C3/de not_active Expired
-
1975
- 1975-05-22 GB GB2232775A patent/GB1466216A/en not_active Expired
- 1975-05-22 IT IT23609/75A patent/IT1038353B/it active
- 1975-06-04 US US05/583,363 patent/US3994928A/en not_active Expired - Lifetime
- 1975-06-05 CA CA228,609A patent/CA1041529A/en not_active Expired
- 1975-06-11 NL NL7506960A patent/NL7506960A/xx not_active Application Discontinuation
- 1975-06-17 FR FR7518967A patent/FR2275251A1/fr active Granted
- 1975-06-17 BE BE157400A patent/BE830323A/xx unknown
- 1975-06-18 JP JP50074269A patent/JPS5829142B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2275251A1 (fr) | 1976-01-16 |
| NL7506960A (nl) | 1975-12-22 |
| FR2275251B1 (enExample) | 1979-08-03 |
| DE2429085B2 (de) | 1980-07-17 |
| DE2429085A1 (de) | 1976-01-08 |
| JPS5114187A (enExample) | 1976-02-04 |
| US3994928A (en) | 1976-11-30 |
| GB1466216A (en) | 1977-03-02 |
| DE2429085C3 (de) | 1981-07-23 |
| BE830323A (fr) | 1975-12-17 |
| IT1038353B (it) | 1979-11-20 |
| CA1041529A (en) | 1978-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0123517B1 (en) | Vapour phase hydrogenation of esters | |
| US4628129A (en) | Process for the preparation of ethylene glycol | |
| JPS61183237A (ja) | 酢酸の水素添加方法 | |
| JP2001046874A (ja) | 水素化用触媒、及びこれを用いるカルボン酸類からのアルコール類の製造方法 | |
| JP3633612B2 (ja) | シェル触媒、その製法および使用 | |
| CN106140152A (zh) | Ag/Al2O3催化剂及其催化氢化5‑羟甲基糠醛制备2，5‑呋喃二甲醇的方法 | |
| JPS5829142B2 (ja) | 無水マレイン酸を液相水素化してγ−ブチロラクトンにするための触媒の製法 | |
| CN104785250A (zh) | 一种加氢催化剂、制备方法及其在制备六氢苯酐中的应用 | |
| US3113138A (en) | Preparation of butyrolactone | |
| US3829448A (en) | Process for producing ypsilon-lactones and cyclic ethers | |
| US4052335A (en) | Catalyst for the production of gamma-butyrolactone and a method for preparing the catalyst | |
| CN116947594A (zh) | 一种合成1,1,2-三氟乙烷的方法 | |
| EP2516360B1 (de) | Isomerisierung von linearen alpha-olefinen | |
| US7214641B2 (en) | Catalyst and hydrogenation of carbonyl compounds in the liquid phase using the catalyst | |
| EP1162186A2 (de) | Verfahren zur Herstellung von d,l-Menthol | |
| US2366464A (en) | Manufacture of tetbahydbofuman | |
| JP3046862B2 (ja) | １５〜２５重量％のトランス−トランス異性体含有ジ−（４−アミノシクロヘキシル）−メタンの製造方法 | |
| US4209651A (en) | Hydrogenation of butadienepolyperoxide to unsaturated diols | |
| US5245082A (en) | Process for the production of di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer | |
| CN119588338B (zh) | 一种烯酮选择性加氢催化剂及其制备方法与应用 | |
| US2130480A (en) | Process of hydrogenating 5-nitrophthalide | |
| JPH09225311A (ja) | 改質ラニーニッケル触媒とその触媒によるジオール化合物の製造方法 | |
| JPS6140226A (ja) | シクロオレフインの製造方法 | |
| US2367287A (en) | Hydrogenation process | |
| SU662538A1 (ru) | Способ получени циклогексана |