JPH0558635B2 - - Google Patents
Info
- Publication number
- JPH0558635B2 JPH0558635B2 JP5572186A JP5572186A JPH0558635B2 JP H0558635 B2 JPH0558635 B2 JP H0558635B2 JP 5572186 A JP5572186 A JP 5572186A JP 5572186 A JP5572186 A JP 5572186A JP H0558635 B2 JPH0558635 B2 JP H0558635B2
- Authority
- JP
- Japan
- Prior art keywords
- acetaldehyde
- aldol
- aldoxane
- para
- acetaldol
- 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 - Lifetime
Links
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 36
- XOXZKNZCICKTLL-UHFFFAOYSA-N 2,6-dimethyl-1,3-dioxan-4-ol Chemical compound CC1CC(O)OC(C)O1 XOXZKNZCICKTLL-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 16
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000005882 aldol condensation reaction Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- VVNWGMADQIFKOH-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxan-4-ol Chemical compound CC1(C)OCCC(O)O1 VVNWGMADQIFKOH-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 6
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5572186A JPS62212384A (ja) | 1986-03-13 | 1986-03-13 | パラアルド−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5572186A JPS62212384A (ja) | 1986-03-13 | 1986-03-13 | パラアルド−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62212384A JPS62212384A (ja) | 1987-09-18 |
| JPH0558635B2 true JPH0558635B2 (enrdf_load_html_response) | 1993-08-27 |
Family
ID=13006727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5572186A Granted JPS62212384A (ja) | 1986-03-13 | 1986-03-13 | パラアルド−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62212384A (enrdf_load_html_response) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3285439B2 (ja) * | 1993-03-24 | 2002-05-27 | ダイセル化学工業株式会社 | 反応粗液の製造法および１，３−ブチレングリコ−ルの製造法 |
| DE69320454T3 (de) * | 1993-03-24 | 2009-08-20 | Daicel Chemical Industries, Ltd. | Verfahren zur Herstellung von 1,3-butylenglykol |
| WO2001056963A1 (en) | 2000-02-04 | 2001-08-09 | Daicel Chemical Industries, Ltd. | High-purity 1,3-butylene glycol, process for producing 1,3-butylene glycol, and process for producing by-product butanol and butyl acetate |
| JP2001213825A (ja) * | 2000-02-04 | 2001-08-07 | Daicel Chem Ind Ltd | 高純度１，３−ブチレングリコール |
| CN108383684B (zh) * | 2018-03-28 | 2021-07-30 | 中国科学院兰州化学物理研究所苏州研究院 | 一种1，3-丁二醇的合成方法及系统 |
| JP7380161B2 (ja) * | 2019-12-09 | 2023-11-15 | 株式会社レゾナック | パラアルドールの製造方法 |
| JP7380181B2 (ja) * | 2019-12-20 | 2023-11-15 | 株式会社レゾナック | パラアルドールの製造方法 |
| CN117700302A (zh) | 2019-12-24 | 2024-03-15 | 株式会社力森诺科 | 1,3-丁二醇的制造方法 |
-
1986
- 1986-03-13 JP JP5572186A patent/JPS62212384A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62212384A (ja) | 1987-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |