DE3505654A1 - Verfahren zur herstellung von 2-alkyl-1,4-butandial - Google Patents
Verfahren zur herstellung von 2-alkyl-1,4-butandialInfo
- Publication number
- DE3505654A1 DE3505654A1 DE19853505654 DE3505654A DE3505654A1 DE 3505654 A1 DE3505654 A1 DE 3505654A1 DE 19853505654 DE19853505654 DE 19853505654 DE 3505654 A DE3505654 A DE 3505654A DE 3505654 A1 DE3505654 A1 DE 3505654A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- propene
- butanedial
- triphenylphosphine
- dialkoxy
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 24
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 12
- 239000010948 rhodium Substances 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 10
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 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 description 19
- 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 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000001273 butane Substances 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- OBSHSWKHUYGFMF-UHFFFAOYSA-N 3,3-dimethoxy-2-methylprop-1-ene Chemical compound COC(OC)C(C)=C OBSHSWKHUYGFMF-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture 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
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BQPPGEDHWKAEDR-UHFFFAOYSA-N 2-methylbutanedial Chemical compound O=CC(C)CC=O BQPPGEDHWKAEDR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTNZAKNDRFTZNR-UHFFFAOYSA-N 2-(dimethoxymethyl)-3-methylbut-1-ene Chemical compound COC(OC)C(=C)C(C)C MTNZAKNDRFTZNR-UHFFFAOYSA-N 0.000 description 2
- WBZIMWTYFPHTPT-UHFFFAOYSA-N 2-(dimethoxymethyl)but-1-ene Chemical compound CCC(=C)C(OC)OC WBZIMWTYFPHTPT-UHFFFAOYSA-N 0.000 description 2
- GBERVGLEGBCOSJ-UHFFFAOYSA-N 2-(dimethoxymethyl)pent-1-ene Chemical compound CCCC(=C)C(OC)OC GBERVGLEGBCOSJ-UHFFFAOYSA-N 0.000 description 2
- BGTHDKVYMGJEIA-UHFFFAOYSA-N 4,4-dimethoxy-3-methylbutanal Chemical compound COC(OC)C(C)CC=O BGTHDKVYMGJEIA-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- -1 aldehyde acetals Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 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 1
- FYQMMABWOLQJEQ-UHFFFAOYSA-N 2-ethylbutanedial Chemical compound CCC(C=O)CC=O FYQMMABWOLQJEQ-UHFFFAOYSA-N 0.000 description 1
- KGXTXYWEGWEZMU-UHFFFAOYSA-N 2-propan-2-ylbutanedial Chemical compound CC(C)C(C=O)CC=O KGXTXYWEGWEZMU-UHFFFAOYSA-N 0.000 description 1
- VQWYEDRISULPNG-UHFFFAOYSA-N 3-(dimethoxymethyl)hexanal Chemical compound CCCC(CC=O)C(OC)OC VQWYEDRISULPNG-UHFFFAOYSA-N 0.000 description 1
- NQPPJKGYVRVYFS-UHFFFAOYSA-N 3-(dimethoxymethyl)pentanal Chemical compound O=CCC(CC)C(OC)OC NQPPJKGYVRVYFS-UHFFFAOYSA-N 0.000 description 1
- GOUMRDDQOZZQDR-UHFFFAOYSA-N 4,4-dimethoxybutanal Chemical compound COC(OC)CCC=O GOUMRDDQOZZQDR-UHFFFAOYSA-N 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-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
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical class CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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)
- Fats And Perfumes (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853505654 DE3505654A1 (de) | 1985-02-19 | 1985-02-19 | Verfahren zur herstellung von 2-alkyl-1,4-butandial |
| EP85116054A EP0191935B1 (de) | 1985-02-19 | 1985-12-17 | Verfahren zur Herstellung von 2-Alkyl-1,4-butandial |
| DE8585116054T DE3565396D1 (en) | 1985-02-19 | 1985-12-17 | Process for the production of 2-alkyl-1,4-butane dial |
| AT85116054T ATE37708T1 (de) | 1985-02-19 | 1985-12-17 | Verfahren zur herstellung von 2-alkyl-1,4butandial. |
| ES551038A ES8701711A1 (es) | 1985-02-19 | 1986-01-20 | Procedimiento para preparar 2-alquil-1,4-butanodial |
| US06/828,488 US4675451A (en) | 1985-02-19 | 1986-02-12 | Process for the preparation of 2-alkyl-1,4-butanedial |
| BR8600633A BR8600633A (pt) | 1985-02-19 | 1986-02-14 | Processo para a obtencao de 2-alquil-1,4-butanodial |
| CA000502099A CA1260497A (en) | 1985-02-19 | 1986-02-18 | Process for producing 2-alkyl-1,4-butanedial |
| JP61033126A JPS61194043A (ja) | 1985-02-19 | 1986-02-19 | ２‐アルキル‐１，４‐ブタンジアールの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853505654 DE3505654A1 (de) | 1985-02-19 | 1985-02-19 | Verfahren zur herstellung von 2-alkyl-1,4-butandial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3505654A1 true DE3505654A1 (de) | 1986-08-21 |
Family
ID=6262903
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853505654 Withdrawn DE3505654A1 (de) | 1985-02-19 | 1985-02-19 | Verfahren zur herstellung von 2-alkyl-1,4-butandial |
| DE8585116054T Expired DE3565396D1 (en) | 1985-02-19 | 1985-12-17 | Process for the production of 2-alkyl-1,4-butane dial |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585116054T Expired DE3565396D1 (en) | 1985-02-19 | 1985-12-17 | Process for the production of 2-alkyl-1,4-butane dial |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4675451A (enExample) |
| EP (1) | EP0191935B1 (enExample) |
| JP (1) | JPS61194043A (enExample) |
| AT (1) | ATE37708T1 (enExample) |
| BR (1) | BR8600633A (enExample) |
| CA (1) | CA1260497A (enExample) |
| DE (2) | DE3505654A1 (enExample) |
| ES (1) | ES8701711A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101835786A (zh) * | 2007-11-06 | 2010-09-15 | 三菱化学株式会社 | 抑制金属从过渡金属络合物析出的方法 |
| CN101792374B (zh) * | 2010-04-06 | 2012-11-28 | 绍兴文理学院 | 1-甲氧基-2，6，10-三甲基-1，3，5，9-十一碳四烯及其制备方法和应用 |
| CN102267881B (zh) * | 2010-06-02 | 2013-07-24 | 绍兴文理学院 | 番茄红素的中间体及其中间体的制备方法 |
| CN102267879B (zh) | 2010-06-02 | 2013-07-03 | 绍兴文理学院 | 番茄红素的中间体及其中间体的制备方法 |
| CN102199078B (zh) * | 2011-04-15 | 2013-04-03 | 浙江医药股份有限公司新昌制药厂 | 一种番茄红素中间体3-甲基-4,4-二烷氧基-1-丁醛的制备方法 |
| 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 |
| CN103172503B (zh) * | 2011-12-26 | 2015-03-11 | 南京工业大学 | 番茄红素中间体3-甲基-4,4-二烷氧基-1-丁醛的制备方法 |
| JP6167857B2 (ja) * | 2013-11-04 | 2017-07-26 | 株式会社デンソー | 車両用シート空調装置 |
| WO2016104332A1 (ja) * | 2014-12-24 | 2016-06-30 | 株式会社クラレ | アルデヒド化合物の製造方法およびアセタール化合物 |
| KR101811102B1 (ko) * | 2015-07-13 | 2017-12-20 | 주식회사 엘지화학 | 인계 리간드를 포함하는 촉매 조성물 및 이를 이용한 하이드로포밀화 방법 |
| CN113480415B (zh) * | 2021-06-30 | 2023-10-24 | 中国成达工程有限公司 | 一种丙烯醛氢甲酰化合成丁二醛工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189655A (en) * | 1961-12-22 | 1965-06-15 | Thompson Benjamin | Dienals |
| FR1524289A (fr) * | 1967-03-29 | 1968-05-10 | Melle Usines Sa | Procédé de scission d'acétals |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| DE3118656A1 (de) * | 1981-05-11 | 1982-11-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (alpha),ss-ungesaettigten aldehyden und 2,7-dimethyl-2,6-octadienal |
| 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 |
| DE3403427A1 (de) * | 1984-02-01 | 1985-08-01 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von 1,4-butandial |
-
1985
- 1985-02-19 DE DE19853505654 patent/DE3505654A1/de not_active Withdrawn
- 1985-12-17 DE DE8585116054T patent/DE3565396D1/de not_active Expired
- 1985-12-17 AT AT85116054T patent/ATE37708T1/de not_active IP Right Cessation
- 1985-12-17 EP EP85116054A patent/EP0191935B1/de not_active Expired
-
1986
- 1986-01-20 ES ES551038A patent/ES8701711A1/es not_active Expired
- 1986-02-12 US US06/828,488 patent/US4675451A/en not_active Expired - Fee Related
- 1986-02-14 BR BR8600633A patent/BR8600633A/pt unknown
- 1986-02-18 CA CA000502099A patent/CA1260497A/en not_active Expired
- 1986-02-19 JP JP61033126A patent/JPS61194043A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4675451A (en) | 1987-06-23 |
| DE3565396D1 (en) | 1988-11-10 |
| ES8701711A1 (es) | 1986-12-01 |
| CA1260497A (en) | 1989-09-26 |
| BR8600633A (pt) | 1986-10-29 |
| EP0191935B1 (de) | 1988-10-05 |
| JPS61194043A (ja) | 1986-08-28 |
| ES551038A0 (es) | 1986-12-01 |
| JPH0567130B2 (enExample) | 1993-09-24 |
| EP0191935A1 (de) | 1986-08-27 |
| ATE37708T1 (de) | 1988-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |