JPH0560814B2 - - Google Patents
Info
- Publication number
- JPH0560814B2 JPH0560814B2 JP61065125A JP6512586A JPH0560814B2 JP H0560814 B2 JPH0560814 B2 JP H0560814B2 JP 61065125 A JP61065125 A JP 61065125A JP 6512586 A JP6512586 A JP 6512586A JP H0560814 B2 JPH0560814 B2 JP H0560814B2
- Authority
- JP
- Japan
- Prior art keywords
- butylene glycol
- acetaldehyde
- reaction
- aldol
- producing
- 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
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 29
- 229940058015 1,3-butylene glycol Drugs 0.000 claims description 14
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 8
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- XOXZKNZCICKTLL-UHFFFAOYSA-N 2,6-dimethyl-1,3-dioxan-4-ol Chemical compound CC1CC(O)OC(C)O1 XOXZKNZCICKTLL-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012535 impurity Substances 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61065125A JPS62246529A (ja) | 1986-03-24 | 1986-03-24 | １，３−ブチレングリコ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61065125A JPS62246529A (ja) | 1986-03-24 | 1986-03-24 | １，３−ブチレングリコ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62246529A JPS62246529A (ja) | 1987-10-27 |
| JPH0560814B2 true JPH0560814B2 (de) | 1993-09-03 |
Family
ID=13277838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61065125A Granted JPS62246529A (ja) | 1986-03-24 | 1986-03-24 | １，３−ブチレングリコ−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62246529A (de) |
Families Citing this family (15)
| 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 |
| DE69331565D1 (de) * | 1993-03-24 | 2002-03-21 | Daicel Chem | Ein verbessertes Verfahren zur Herstellung von 1,3-Butylenglykol |
| JP3369707B2 (ja) * | 1994-03-17 | 2003-01-20 | ダイセル化学工業株式会社 | １，３−ブチレングリコ−ルの精製方法 |
| JP4530461B2 (ja) * | 2000-02-04 | 2010-08-25 | ダイセル化学工業株式会社 | １，３−ブチレングリコールの精製方法 |
| 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 |
| CN105585448B (zh) * | 2016-03-09 | 2019-11-05 | 辽宁科隆精细化工股份有限公司 | 一种合成化妆品级1,3-丁二醇的方法 |
| 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 |
| JP6804602B1 (ja) * | 2019-09-05 | 2020-12-23 | 株式会社ダイセル | １，３−ブチレングリコール製品 |
| JP6979473B2 (ja) * | 2020-01-07 | 2021-12-15 | 株式会社ダイセル | １，３−ブチレングリコール製品 |
| EP4026823A4 (de) * | 2019-09-05 | 2022-11-23 | Daicel Corporation | 1,3-butylenglykolprodukt |
| JP6890709B2 (ja) * | 2019-09-05 | 2021-06-18 | 株式会社ダイセル | １，３−ブチレングリコール製品 |
| JP6890708B2 (ja) * | 2019-09-05 | 2021-06-18 | 株式会社ダイセル | １，３−ブチレングリコール製品 |
| JP6804601B1 (ja) * | 2019-09-05 | 2020-12-23 | 株式会社ダイセル | １，３−ブチレングリコール製品 |
| 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 |
-
1986
- 1986-03-24 JP JP61065125A patent/JPS62246529A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62246529A (ja) | 1987-10-27 |
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