KR100758135B1 - 말레산을 1,4-부탄디올로 수소화시키기 위한 촉매 및 이의 제조방법, 및 이의 사용방법 - Google Patents
말레산을 1,4-부탄디올로 수소화시키기 위한 촉매 및 이의 제조방법, 및 이의 사용방법 Download PDFInfo
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- KR100758135B1 KR100758135B1 KR1019990033509A KR19990033509A KR100758135B1 KR 100758135 B1 KR100758135 B1 KR 100758135B1 KR 1019990033509 A KR1019990033509 A KR 1019990033509A KR 19990033509 A KR19990033509 A KR 19990033509A KR 100758135 B1 KR100758135 B1 KR 100758135B1
- Authority
- KR
- South Korea
- Prior art keywords
- weight
- carbon support
- catalyst
- butanediol
- palladium
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims abstract description 94
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims abstract description 64
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims abstract description 31
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 25
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 title claims abstract description 25
- 239000011976 maleic acid Substances 0.000 title claims abstract description 25
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 33
- 238000002360 preparation method Methods 0.000 title description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 100
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 71
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 66
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 52
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 34
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052709 silver Inorganic materials 0.000 claims abstract description 33
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000004332 silver Substances 0.000 claims abstract description 30
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 29
- 239000010941 cobalt Substances 0.000 claims abstract description 29
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000002243 precursor Substances 0.000 claims abstract description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 19
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 14
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- 229910017604 nitric acid Inorganic materials 0.000 claims description 13
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 11
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- 238000010438 heat treatment Methods 0.000 claims description 10
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- -1 maleate ester Chemical class 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 229940014800 succinic anhydride Drugs 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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- 239000000126 substance Substances 0.000 claims description 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 3
- 239000001384 succinic acid Substances 0.000 claims description 3
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims description 2
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- 239000002184 metal Substances 0.000 abstract description 11
- 239000000243 solution Substances 0.000 description 33
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 10
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- 239000002245 particle Substances 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 5
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- 239000006227 byproduct Substances 0.000 description 4
- 150000002506 iron compounds Chemical class 0.000 description 4
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 150000003282 rhenium compounds Chemical class 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229940100890 silver compound Drugs 0.000 description 4
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- 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 3
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 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
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- B01J35/19—Catalysts containing parts with different compositions
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- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
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- 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
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
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- 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
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- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (26)
- 팔라듐 0.1 내지 20중량%, 은 0.1 내지 20중량%, 레늄 0.1 내지 20중량%, 및 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질 0.1 내지 5중량%를 탄소 지지체로 지지된 상태로 포함하는, 말레산을 1,4-부탄디올로 수소화시키기 위한 촉매.
- 삭제
- 제1항에 있어서, 팔라듐 2 내지 4중량%, 은 2 내지 4중량%, 레늄 5 내지 9중량%, 및 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질 0.2 내지 0.6중량%를 포함하는 촉매.
- 말레산, 말레산 무수물, 푸마르산, 석신산, 석신산 무수물, 말레에이트 에스테르, 석시네이트 에스테르, γ-부티로락톤 및 이들의 혼합물로 이루어진 그룹으로부터 선택된, 수소화 가능한 전구체를, 팔라듐 0.1 내지 20중량%, 은 0.1 내지 20중량%, 레늄 0.1 내지 20중량%, 및 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질 0.1 내지 5중량%를 탄소 지지체로 지지된 상태로 포함하는 수소화 촉매 및 수소 함유 기체와 접촉시켜 촉매적으로 수소화시킴을 포함하는, 1,4-부탄디올의 제조방법.
- 삭제
- 제4항에 있어서, 수소화 가능한 전구체가 말레산, 석신산 및 γ-부티로락톤 중 1종 이상의 물질인, 1,4-부탄디올의 제조방법.
- 삭제
- 제4항에 있어서, 촉매가 팔라듐 2 내지 4중량%, 은 2 내지 4중량%, 레늄 5 내지 9중량%, 및 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질 0.2 내지 0.6중량%를 포함하는, 1,4-부탄디올의 제조방법.
- 제4항에 있어서, 수소 대 수소화 가능한 전구체의 비가 5:1 내지 1000:1인, 1,4-부탄디올의 제조방법.
- 제4항에 있어서, 수소 함유 기체의 압력이 20 내지 400기압인, 1,4-부탄디올의 제조방법.
- 제4항에 있어서, 접촉 시간이 0.1분 내지 20시간인, 1,4-부탄디올의 제조방법.
- 탄소 지지체를 산화제와 접촉시켜 탄소 지지체를 산화시키는 단계(i),탄소 지지체를, 팔라듐, 은 및 레늄과, 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질의 공급원과 접촉시킴을 포함하는 함침 단계 1개 이상에 의해 함침시키는 단계(ⅱ),각각의 함침 단계 이후, 함침된 탄소 지지체를 건조시켜 용매를 제거하는 단계(ⅲ) 및함침된 탄소 지지체를, 환원 조건하에 주위 온도로부터 100 내지 350℃로 가열하는 단계(ⅳ)를 포함하는, 팔라듐 0.1 내지 20중량%, 은 0.1 내지 20중량%, 레늄 0.1 내지 20중량%, 및 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질 0.1 내지 5중량%를 탄소 지지체로 지지된 상태로 포함하는, 1,4-부탄디올 제조용 촉매의 제조방법.
- 제12항에 있어서, 탄소 지지체를 산화제와 접촉시키는 단계와, 탄소 지지체를, 팔라듐, 은 및 레늄과, 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 공급원으로 함침시키는 단계를 거의 동시에 수행하는, 1,4-부탄디올 제조용 촉매의 제조방법.
- 제12항에 있어서, 산화제가 질산, 과산화수소, 차아염소산나트륨, 과황산암모늄, 과염소산 및 산소로 이루어진 그룹으로부터 선택되는, 1,4-부탄디올의 제조에 사용되는 촉매의 제조방법.
- 삭제
- 제12항에 있어서, 수소화 가능한 전구체가 말레산, 말레산 무수물, 석신산, 석신산 무수물, 디메틸 석시네이트, γ-부티로락톤 및 이들의 혼합물로 이루어진 그룹으로부터 선택되는, 1,4-부탄디올의 제조에 사용되는 촉매의 제조방법.
- 탄소 지지체를 산화제와 접촉시켜 탄소 지지체를 산화시키는 단계(i),탄소 지지체를, 팔라듐, 은 및 레늄과, 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질의 공급원과 접촉시킴을 포함하는 함침 단계 1개 이상에 의해 함침시키는 단계(ⅱ),각각의 함침 단계 이후, 함침된 탄소 지지체를 건조시켜 용매를 제거하는 단계(ⅲ) 및함침된 탄소 지지체를, 환원 조건하에 주위 온도로부터 100 내지 350℃로 가열하는 단계(ⅳ)에 의해 제조된, 팔라듐 0.1 내지 20중량%, 은 0.1 내지 20중량%, 레늄 0.1 내지 20중량%, 및 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질 0.1 내지 5중량%를 탄소 지지체로 지지된 상태로 포함하는 수소화 촉매를 말레산, 말레산 무수물, 푸마르산, 석신산, 석신산 무수물, 말레에이트 에스테르, 석시네이트 에스테르, γ-부티로락톤 및 이들의 혼합물로 이루어진 그룹으로부터 선택된, 수소화 가능한 전구체와 접촉시켜 당해 전구체를 촉매적으로 수소화시킴을 포함하는, 테트라하이드로푸란과 1,4-부탄디올의 제조방법.
- 삭제
- 제17항에 있어서, 수소화 가능한 전구체가 말레산, 석신산 및 γ-부티로락톤 중 1종 이상의 물질인, 테트라하이드로푸란과 1,4-부탄디올의 제조방법.
- 삭제
- 제17항에 있어서, 촉매가 팔라듐 2 내지 4중량%, 은 2 내지 4중량%, 레늄 5 내지 9중량%, 및 알루미늄, 코발트 및 이들의 혼합물 중 1종 이상의 물질 0.2 내지 0.6중량%를 포함하는, 테트라하이드로푸란과 1,4-부탄디올의 제조방법.
- 제17항에 있어서, 수소 대 수소화 가능한 전구체의 비가 5:1 내지 1000:1인, 테트라하이드로푸란과 1,4-부탄디올의 제조방법.
- 제17항에 있어서, 수소 함유 기체의 압력이 20 내지 400기압인, 테트라하이드로푸란과 1,4-부탄디올의 제조방법.
- 제17항에 있어서, 접촉 시간이 0.1분 내지 20시간인, 테트라하이드로푸란과 1,4-부탄디올의 제조방법.
- 제17항에 있어서, 산화제가 질산, 과산화수소, 차아염소산나트륨, 과황산암모늄, 과염소산 및 산소로 이루어진 그룹으로부터 선택되는, 테트라하이드로푸란과 1,4-부탄디올의 제조방법.
- 제4항에 있어서, 수소화 촉매를 수소화 가능한 전구체 및 수소와 접촉시킨 후 생성된 물질을 주위 온도로부터 50 내지 250℃로 추가로 가열함을 포함하는, 1,4-부탄디올의 제조방법.
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