JPS60158124A - １，４−ブタンジオ−ルの製法 - Google Patents
１，４−ブタンジオ−ルの製法Info
- Publication number
- JPS60158124A JPS60158124A JP59267635A JP26763584A JPS60158124A JP S60158124 A JPS60158124 A JP S60158124A JP 59267635 A JP59267635 A JP 59267635A JP 26763584 A JP26763584 A JP 26763584A JP S60158124 A JPS60158124 A JP S60158124A
- Authority
- JP
- Japan
- Prior art keywords
- producing
- butanediol
- reaction
- rhodium
- carried out
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 32
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 229910052703 rhodium Inorganic materials 0.000 claims description 17
- 239000010948 rhodium Substances 0.000 claims description 17
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 14
- 239000002904 solvent Chemical group 0.000 claims description 14
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910002090 carbon oxide Inorganic materials 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000003284 rhodium compounds Chemical class 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UIKQNMXWCYQNCS-UHFFFAOYSA-N 2-hydroxybutanal Chemical compound CCC(O)C=O UIKQNMXWCYQNCS-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- MJBPUQUGJNAPAZ-AWEZNQCLSA-N butin Chemical compound C1([C@@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-AWEZNQCLSA-N 0.000 description 2
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N 2-methylpropane-1,2-diol Chemical compound CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 description 1
- VXCUURYYWGCLIH-UHFFFAOYSA-N Dodecanenitrile Chemical compound CCCCCCCCCCCC#N VXCUURYYWGCLIH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- LVGLLYVYRZMJIN-UHFFFAOYSA-N carbon monoxide;rhodium Chemical group [Rh].[Rh].[Rh].[Rh].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] LVGLLYVYRZMJIN-UHFFFAOYSA-N 0.000 description 1
- ADGFUTSPEKVFKD-UHFFFAOYSA-N carbonyl dichloride;rhodium Chemical compound [Rh].ClC(Cl)=O ADGFUTSPEKVFKD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ADXDTXPZNUXXNO-UHFFFAOYSA-N dibutyl(octadecyl)phosphane Chemical compound CCCCCCCCCCCCCCCCCCP(CCCC)CCCC ADXDTXPZNUXXNO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- LEMQFDHLRUSMPZ-UHFFFAOYSA-N ethyl(dimethyl)phosphane Chemical compound CCP(C)C LEMQFDHLRUSMPZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- BLALACGZENSEPF-UHFFFAOYSA-N phosphanylidenemethanone;rhodium Chemical class [Rh].O=C=P BLALACGZENSEPF-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- MLRCLPRHEOPXLL-UHFFFAOYSA-N tetradecanenitrile Chemical compound CCCCCCCCCCCCCC#N MLRCLPRHEOPXLL-UHFFFAOYSA-N 0.000 description 1
- GRAKJTASWCEOQI-UHFFFAOYSA-N tridodecylphosphane Chemical compound CCCCCCCCCCCCP(CCCCCCCCCCCC)CCCCCCCCCCCC GRAKJTASWCEOQI-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- KJFAJLYXKTVJDA-UHFFFAOYSA-N trioctadecylphosphane Chemical compound CCCCCCCCCCCCCCCCCCP(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC KJFAJLYXKTVJDA-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- PKYBDXJPJDJCPS-UHFFFAOYSA-N tris-decylphosphane Chemical compound CCCCCCCCCCP(CCCCCCCCCC)CCCCCCCCCC PKYBDXJPJDJCPS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8304475 | 1983-12-29 | ||
| NL8304475 | 1983-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60158124A true JPS60158124A (ja) | 1985-08-19 |
| JPH0564132B2 JPH0564132B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-09-14 |
Family
ID=19842944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59267635A Granted JPS60158124A (ja) | 1983-12-29 | 1984-12-20 | １，４−ブタンジオ−ルの製法 |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021510727A (ja) * | 2018-02-26 | 2021-04-30 | ライオンデル ケミカル テクノロジー、エル．ピー． | グリセリン製アリルアルコールのヒドロホルミル化によるｂｄｏの製造 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8921947D0 (en) * | 1989-09-28 | 1989-11-15 | British Petroleum Co Plc | Process for the formation of alcohols |
| US6756411B2 (en) * | 1995-06-29 | 2004-06-29 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
| US6127584A (en) * | 1999-04-14 | 2000-10-03 | Arco Chemical Technology, L.P. | Butanediol production |
| EP3041942B1 (en) | 2013-09-03 | 2020-07-01 | PTT Global Chemical Public Company Limited | A process for manufacturing acrylic acid, acrylonitrile and 1,4-butanediol from 1,3-propanediol |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5129412A (en) * | 1974-08-30 | 1976-03-12 | Kuraray Co | Butanjioorurui no seizohoho |
| JPS5278809A (en) * | 1975-12-26 | 1977-07-02 | Ube Ind Ltd | Preparation of 1, 4-butanediol |
| JPS5384907A (en) * | 1976-12-30 | 1978-07-26 | Gen Electric | Process for preparing buthanediol |
| JPS54106407A (en) * | 1978-02-09 | 1979-08-21 | Kuraray Co Ltd | Hydroformylation of allyl alcohol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239566A (en) * | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US4219684A (en) * | 1979-04-02 | 1980-08-26 | Uop Inc. | Synthesis of alcohols by hydroformylation with nitrile promoter |
| JPS55151521A (en) * | 1979-05-15 | 1980-11-26 | Toyo Soda Mfg Co Ltd | Preparation of alcohol |
-
1984
- 1984-10-24 US US06/664,128 patent/US4590311A/en not_active Expired - Fee Related
- 1984-11-23 DE DE8484201702T patent/DE3468207D1/de not_active Expired
- 1984-11-23 EP EP84201702A patent/EP0151822B1/en not_active Expired
- 1984-11-28 CA CA000468765A patent/CA1272217A/en not_active Expired - Fee Related
- 1984-12-20 JP JP59267635A patent/JPS60158124A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5129412A (en) * | 1974-08-30 | 1976-03-12 | Kuraray Co | Butanjioorurui no seizohoho |
| JPS5278809A (en) * | 1975-12-26 | 1977-07-02 | Ube Ind Ltd | Preparation of 1, 4-butanediol |
| JPS5384907A (en) * | 1976-12-30 | 1978-07-26 | Gen Electric | Process for preparing buthanediol |
| JPS54106407A (en) * | 1978-02-09 | 1979-08-21 | Kuraray Co Ltd | Hydroformylation of allyl alcohol |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021510727A (ja) * | 2018-02-26 | 2021-04-30 | ライオンデル ケミカル テクノロジー、エル．ピー． | グリセリン製アリルアルコールのヒドロホルミル化によるｂｄｏの製造 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0564132B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-09-14 |
| EP0151822A1 (en) | 1985-08-21 |
| US4590311A (en) | 1986-05-20 |
| CA1272217A (en) | 1990-07-31 |
| DE3468207D1 (en) | 1988-02-04 |
| EP0151822B1 (en) | 1987-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS60158124A (ja) | １，４−ブタンジオ−ルの製法 | |
| US4337363A (en) | Process for the preparation of 3-(4-methyl-3-cyclohexen-1-yl) butyraldehyde | |
| US4543411A (en) | Process for selective preparation of secondary and tertiary amines | |
| KR100878911B1 (ko) | 포스포라노알칸 리간드를 가진 촉매를 이용하여산화에틸렌과 합성가스로부터 1,3-프로판디올을 제조하는1단계 생산 방법 | |
| JPS58922A (ja) | アルカノ−ルの製造法 | |
| KR102741786B1 (ko) | 선택적 균일계 수소화 촉매의 회수 방법 및 재사용 방법 | |
| JP3194803B2 (ja) | ラクトン類の製造方法 | |
| US4396726A (en) | Process for preparing ethylene glycol and lower monohydric alcohols from syn gas using a novel catalyst system | |
| US4529808A (en) | Bi-solvent system for the hydroformylation of allyl alcohol using a rhodium catalyst | |
| JPS60116652A (ja) | 第２級および第３級アルアルキルアミン類の選択的製造方法 | |
| JPS5989642A (ja) | モノオレフイン化合物のカルボニル化による線状エステルの製造法 | |
| JPH0782260A (ja) | ラクトン類の製法 | |
| KR20200076301A (ko) | 선택적 균일계 수소화 촉매의 회수 방법 및 재사용 방법 | |
| JPH05320087A (ja) | ヒドロキシブチルアルデヒド類の製法 | |
| JPS5849534B2 (ja) | アルデヒドの製造方法 | |
| US4433177A (en) | Process for preparing acetaldehyde from methanol and synthesis gas using a novel catalyst composition | |
| JPH06107654A (ja) | ラクトン類の製造法 | |
| JP3691235B2 (ja) | 光学活性ピペリジン類の製造方法 | |
| JPH0733756A (ja) | ラクトン類を製造する方法 | |
| CA2461284A1 (en) | One step hydroformylation and hydrogenation process for preparing a 1,3-propanediol | |
| JPH026427A (ja) | ジカルボン酸およびホルミルカルボン酸の製造方法 | |
| US4558072A (en) | Process for preparing ethylene glycol and lower monohydric alcohols from syngas using a novel catalyst system | |
| JPS5984831A (ja) | １，４−ジヒドロキシブテン−２の製造法 | |
| JPS62263140A (ja) | α−フエニルプロピオン酸誘導体の製造法 | |
| JPH01121234A (ja) | ４−ヒドロキシブタナール類の製法 |