DD232486A5 - Verfahren zur herstellung von 1,4-butandial - Google Patents
Verfahren zur herstellung von 1,4-butandial Download PDFInfo
- Publication number
- DD232486A5 DD232486A5 DD85272874A DD27287485A DD232486A5 DD 232486 A5 DD232486 A5 DD 232486A5 DD 85272874 A DD85272874 A DD 85272874A DD 27287485 A DD27287485 A DD 27287485A DD 232486 A5 DD232486 A5 DD 232486A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- acrolein
- propene
- butanedial
- hydroformylation
- triphenylphosphine
- Prior art date
Links
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 21
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 18
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims abstract description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims abstract description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- MCIPQLOKVXSHTD-UHFFFAOYSA-N 3,3-diethoxyprop-1-ene Chemical compound CCOC(C=C)OCC MCIPQLOKVXSHTD-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001241 acetals Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- OBWGMYALGNDUNM-UHFFFAOYSA-N 3,3-dimethoxyprop-1-ene Chemical compound COC(OC)C=C OBWGMYALGNDUNM-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- -1 allylidene diacylate Chemical compound 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- XFJRTFAUGYGSKV-UHFFFAOYSA-N 3,3-diethoxy-2-methylpropanal Chemical compound CCOC(OCC)C(C)C=O XFJRTFAUGYGSKV-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- JMVAYXBTMOFWKZ-UHFFFAOYSA-N 4,4-diethoxybutanal Chemical compound CCOC(OCC)CCC=O JMVAYXBTMOFWKZ-UHFFFAOYSA-N 0.000 description 2
- GOUMRDDQOZZQDR-UHFFFAOYSA-N 4,4-dimethoxybutanal Chemical compound COC(OC)CCC=O GOUMRDDQOZZQDR-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- CFVASXBRVLAXGV-UHFFFAOYSA-N 2,5-dichlorooxolane Chemical compound ClC1CCC(Cl)O1 CFVASXBRVLAXGV-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- RTLKEBICSWRUIF-UHFFFAOYSA-N 3,3-dimethoxy-2-methylpropanal Chemical compound COC(OC)C(C)C=O RTLKEBICSWRUIF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843403427 DE3403427A1 (de) | 1984-02-01 | 1984-02-01 | Verfahren zur herstellung von 1,4-butandial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD232486A5 true DD232486A5 (de) | 1986-01-29 |
Family
ID=6226448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85272874A DD232486A5 (de) | 1984-02-01 | 1985-01-30 | Verfahren zur herstellung von 1,4-butandial |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4608443A (pt) |
| EP (1) | EP0151241B1 (pt) |
| JP (1) | JPH0629205B2 (pt) |
| AT (1) | ATE30146T1 (pt) |
| BR (1) | BR8500420A (pt) |
| CA (1) | CA1265533A (pt) |
| DD (1) | DD232486A5 (pt) |
| DE (2) | DE3403427A1 (pt) |
| ES (1) | ES538662A0 (pt) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3505654A1 (de) * | 1985-02-19 | 1986-08-21 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von 2-alkyl-1,4-butandial |
| US4742178A (en) * | 1986-11-10 | 1988-05-03 | Eastman Kodak Company | Low pressure hydroformylation of dienes |
| DE3920423A1 (de) * | 1989-06-22 | 1991-01-03 | Basf Ag | Verfahren zur herstellung von 2,3-dialkoxypropanalen |
| KR20100058550A (ko) * | 2007-09-11 | 2010-06-03 | 몬도바이오테크 래보래토리즈 아게 | 녹농균 감염 치료시 치료제로서의 밴드 ３ 단백질 （８２４－８２９） 및／또는 멜라닌세포－자극 호르몬 방출－저해 인자의 용도 |
| JP2012201624A (ja) * | 2011-03-25 | 2012-10-22 | Kuraray Co Ltd | ４−アミノブチルアルデヒドアセタールの製造方法 |
| CN102276427B (zh) * | 2011-07-19 | 2013-05-01 | 湖北新景新材料有限公司 | 一种用丙烯醛制备缩醛的方法 |
| CN102924249B (zh) * | 2011-08-10 | 2014-10-29 | 浙江医药股份有限公司新昌制药厂 | 番茄红素中间体2-甲基-3,3-二甲氧基-1-丙醛的制备方法 |
| CN102924250B (zh) * | 2011-08-10 | 2015-08-05 | 浙江医药股份有限公司新昌制药厂 | 番茄红素中间体2-甲基-3,3-二烷氧基-1-丙醛的制备方法 |
| EP3239127A4 (en) * | 2014-12-24 | 2018-08-15 | Kuraray Co., Ltd. | Method for producing aldehyde compound, and acetal compound |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137738A (en) * | 1964-06-16 | Acetal production | ||
| US2626283A (en) * | 1953-01-20 | Preparation of acrolein acetal | ||
| US2288211A (en) * | 1938-05-19 | 1942-06-30 | Chemical Marketing Company Inc | Process for the production of betaalkoxyaldehydes |
| GB702206A (en) * | 1950-03-31 | 1954-01-13 | Anglo Iranian Oil Co Ltd | Improvements in or relating to the production of dialdehydes and derivatives thereof |
| US2784235A (en) * | 1954-11-29 | 1957-03-05 | Shell Dev | Method for preparing substituted dialdehydes |
| US2920081A (en) * | 1957-05-08 | 1960-01-05 | Union Carbide Corp | Production of 2, 5-dialkoxy-tetrahydrofuran |
| FR1524289A (fr) * | 1967-03-29 | 1968-05-10 | Melle Usines Sa | Procédé de scission d'acétals |
| DE2537448A1 (de) * | 1975-08-22 | 1977-03-03 | Basf Ag | In 6-stellung substituierte acetale des hexan-1-als |
| US4200591A (en) * | 1977-06-21 | 1980-04-29 | Johnson, Matthey & Co., Limited | Catalytic hydroformylation |
| US4161616A (en) * | 1978-04-24 | 1979-07-17 | Celanese Corporation | Acrolein conversion to butanediol |
| EP0018161B1 (en) * | 1979-04-11 | 1983-05-25 | DAVY McKEE (LONDON) LIMITED | Aldehyde-ethers and process for their production |
| FR2459683A1 (fr) * | 1979-06-22 | 1981-01-16 | Ugine Kuhlmann | Procede de stabilisation et de regeneration du catalyseur d'hydroformylation du propene |
| DE2932527A1 (de) * | 1979-08-10 | 1981-02-26 | Basf Ag | Tert.-butoxy-butanale und -butanole sowie bis-tert.-butoxypentanale und -pentanole |
| SU878760A1 (ru) * | 1979-08-13 | 1981-11-07 | Армянский Филиал Ордена Трудового Красного Знамени Всесоюзного Научно-Исследовательского Института Химических Реактивов И Особо Чистых Веществ | Способ получени глутарового альдегида |
| US4288380A (en) * | 1979-11-01 | 1981-09-08 | Union Carbide Corporation | Heteronuclear-bridged rhodium clusters |
| EP0094748B1 (en) * | 1982-05-11 | 1986-01-22 | Imperial Chemical Industries Plc | Process for the production of unsaturated mono or saturated dialdehydes and acetals thereof |
| FR2535711B1 (fr) * | 1982-11-05 | 1986-06-27 | Inst Francais Du Petrole | Procede d'homologation d'alcools par l'intermediaire de cetals catalysee par les complexes carbonyles du cobalt |
| JPS58201743A (ja) * | 1982-05-19 | 1983-11-24 | Kuraray Co Ltd | １，９−ノナンジア−ルを製造する方法 |
| US4533756A (en) * | 1983-11-07 | 1985-08-06 | Texaco Inc. | Process for synthesis of acrylic acid precursors via hydroformylation of vinyl ether |
-
1984
- 1984-02-01 DE DE19843403427 patent/DE3403427A1/de not_active Withdrawn
- 1984-11-15 EP EP84113804A patent/EP0151241B1/de not_active Expired
- 1984-11-15 AT AT84113804T patent/ATE30146T1/de not_active IP Right Cessation
- 1984-11-15 DE DE8484113804T patent/DE3466678D1/de not_active Expired
- 1984-12-17 ES ES538662A patent/ES538662A0/es active Granted
-
1985
- 1985-01-24 US US06/694,372 patent/US4608443A/en not_active Expired - Fee Related
- 1985-01-30 BR BR8500420A patent/BR8500420A/pt unknown
- 1985-01-30 DD DD85272874A patent/DD232486A5/de unknown
- 1985-01-31 JP JP60015664A patent/JPH0629205B2/ja not_active Expired - Lifetime
- 1985-01-31 CA CA000473284A patent/CA1265533A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0629205B2 (ja) | 1994-04-20 |
| JPS60188341A (ja) | 1985-09-25 |
| EP0151241B1 (de) | 1987-10-07 |
| EP0151241A1 (de) | 1985-08-14 |
| DE3403427A1 (de) | 1985-08-01 |
| ES8601832A1 (es) | 1985-11-01 |
| ATE30146T1 (de) | 1987-10-15 |
| US4608443A (en) | 1986-08-26 |
| ES538662A0 (es) | 1985-11-01 |
| CA1265533A (en) | 1990-02-06 |
| DE3466678D1 (en) | 1987-11-12 |
| BR8500420A (pt) | 1985-09-10 |
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