DE2425761A1 - Kontinuierliches verfahren fuer die erzeugung eines diols aus einem diolester - Google Patents
Kontinuierliches verfahren fuer die erzeugung eines diols aus einem diolesterInfo
- Publication number
- DE2425761A1 DE2425761A1 DE19742425761 DE2425761A DE2425761A1 DE 2425761 A1 DE2425761 A1 DE 2425761A1 DE 19742425761 DE19742425761 DE 19742425761 DE 2425761 A DE2425761 A DE 2425761A DE 2425761 A1 DE2425761 A1 DE 2425761A1
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- reactor
- ester
- diol
- boiling point
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 23
- 150000002009 diols Chemical class 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- -1 diol ester Chemical class 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000009835 boiling Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 18
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- BMNRJWUOBYYCRX-UHFFFAOYSA-N 1-hydroxybutyl acetate Chemical compound CCCC(O)OC(C)=O BMNRJWUOBYYCRX-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006136 alcoholysis reaction Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- KYCXTUXIIANKNP-UHFFFAOYSA-N 1-acetyloxybutyl acetate Chemical compound CCCC(OC(C)=O)OC(C)=O KYCXTUXIIANKNP-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000007788 liquid Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36523073A | 1973-05-30 | 1973-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2425761A1 true DE2425761A1 (de) | 1975-01-02 |
Family
ID=23438009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742425761 Withdrawn DE2425761A1 (de) | 1973-05-30 | 1974-05-28 | Kontinuierliches verfahren fuer die erzeugung eines diols aus einem diolester |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5030811A (enrdf_load_stackoverflow) |
| BR (1) | BR7404448D0 (enrdf_load_stackoverflow) |
| CA (1) | CA1027144A (enrdf_load_stackoverflow) |
| DE (1) | DE2425761A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2231647B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1468412A (enrdf_load_stackoverflow) |
| IT (1) | IT1012959B (enrdf_load_stackoverflow) |
| NL (1) | NL7407240A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029973A1 (de) * | 1979-11-30 | 1981-06-10 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung vicinaler Diole |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53127405A (en) * | 1977-04-08 | 1978-11-07 | Japan Synthetic Rubber Co Ltd | Continuous preparation of 1,4-butanediol |
| JPS5426436A (en) * | 1977-07-30 | 1979-02-28 | Shin Kobe Electric Machinery | Closed lead storage battery |
| JPS6399049U (enrdf_load_stackoverflow) * | 1986-12-18 | 1988-06-27 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE755284A (fr) * | 1969-08-30 | 1971-02-01 | Degussa | Procede de preparation de glycerine |
| DE2054987A1 (de) * | 1970-11-09 | 1972-05-10 | Knapsack Ag, 5033 Knapsack | Verfahren zur Herstellung von 2-Methylenpropandiol-( 1,3) |
-
1974
- 1974-04-04 CA CA196,825A patent/CA1027144A/en not_active Expired
- 1974-05-09 GB GB2049174A patent/GB1468412A/en not_active Expired
- 1974-05-28 DE DE19742425761 patent/DE2425761A1/de not_active Withdrawn
- 1974-05-29 JP JP49059845A patent/JPS5030811A/ja active Pending
- 1974-05-29 FR FR7418581A patent/FR2231647B1/fr not_active Expired
- 1974-05-29 NL NL7407240A patent/NL7407240A/xx not_active Application Discontinuation
- 1974-05-30 BR BR4448/74A patent/BR7404448D0/pt unknown
- 1974-05-30 IT IT23353/74A patent/IT1012959B/it active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029973A1 (de) * | 1979-11-30 | 1981-06-10 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung vicinaler Diole |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7407240A (enrdf_load_stackoverflow) | 1974-12-03 |
| IT1012959B (it) | 1977-03-10 |
| JPS5030811A (enrdf_load_stackoverflow) | 1975-03-27 |
| FR2231647A1 (enrdf_load_stackoverflow) | 1974-12-27 |
| BR7404448D0 (pt) | 1975-09-30 |
| AU6951774A (en) | 1975-12-04 |
| FR2231647B1 (enrdf_load_stackoverflow) | 1979-07-27 |
| GB1468412A (en) | 1977-03-23 |
| CA1027144A (en) | 1978-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |