GB806769A - Improvements in or relating to the production of esters - Google Patents
Improvements in or relating to the production of estersInfo
- Publication number
- GB806769A GB806769A GB832257A GB832257A GB806769A GB 806769 A GB806769 A GB 806769A GB 832257 A GB832257 A GB 832257A GB 832257 A GB832257 A GB 832257A GB 806769 A GB806769 A GB 806769A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction zone
- methyl
- ester
- continuously
- reaction
- 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
Links
- 150000002148 esters Chemical class 0.000 title abstract 8
- 238000006243 chemical reaction Methods 0.000 abstract 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 4
- 229920005989 resin Polymers 0.000 abstract 4
- 239000011347 resin Substances 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 238000004821 distillation Methods 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229920001429 chelating resin Polymers 0.000 abstract 2
- 230000018044 dehydration Effects 0.000 abstract 2
- 238000006297 dehydration reaction Methods 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical class CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 abstract 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 abstract 1
- 229920002125 Sokalan® Polymers 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- IDNUEBSJWINEMI-UHFFFAOYSA-N ethyl nitrate Chemical compound CCO[N+]([O-])=O IDNUEBSJWINEMI-UHFFFAOYSA-N 0.000 abstract 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- 229940017219 methyl propionate Drugs 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- KAOQVXHBVNKNHA-UHFFFAOYSA-N propyl nitrite Chemical compound CCCON=O KAOQVXHBVNKNHA-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters having a boiling-point below 100 DEG C. are prepared by continuously reacting an acid and an alcohol in a reaction zone in which esterification conditions of temperature and acid concentration are maintained, continuously recovering the ester by distillation, continuously removing reaction liquor from the reaction zone and contacting it with a cationic exchange resin to remove water, and recycling incompletely reacted material to the reaction zone. The resin is preferably arranged in parallel flow beds, one being used for the dehydration while another is being regenerated. Preferred resins are those of the sulphonic acid type, such as Zeo-Karb H, Amberlite IR-120, Permutit 216, Dowex 50, Ionac C-200, Duolite C-3, Wofatit P, Wofatit C and Alkalex ("ZeoKarb," "Amberlite" and "Permutit" are Registered Trade Marks). The resin is preferably presaturated with the alcohol or the equilibrium reaction mixture. It may be regenerated by washing or distilling out adsorbed water, e.g. with a solvent naphtha or by azeotropic distillation with Skellysolve-C (technical n-heptane). The treated reaction liquor may be returned as such to the reaction zone or the ester first recovered by distillation. The ester may be continuously distilled directly from the reaction zone, or from continuously withdrawn reaction liquor; or the reaction liquor can be continuously withdrawn in a single or combined stream to be passed successively through dehydration and distillation zones in any sequence. Examples describe the preparation of trimethyl borate; with this ester residence times in the reaction zone of less than 15 minutes and an instantaneous ester concentration representing a conversion of 2-30 per cent of acid are preferred. Other esters mentioned are methyl, ethyl and isopropyl formates, methyl, ethyl and vinyl acetates, methyl chloroformate, methyl propionate, methyl isobutyrate and lower alkyl esters of inorganic acids, such as propyl nitrite, ethyl nitrate and methyl carbonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB832257A GB806769A (en) | 1957-03-13 | 1957-03-13 | Improvements in or relating to the production of esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB832257A GB806769A (en) | 1957-03-13 | 1957-03-13 | Improvements in or relating to the production of esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB806769A true GB806769A (en) | 1958-12-31 |
Family
ID=9850313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB832257A Expired GB806769A (en) | 1957-03-13 | 1957-03-13 | Improvements in or relating to the production of esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB806769A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012021965A1 (en) * | 2010-08-20 | 2012-02-23 | Enerkem, Inc. | Production of acetates from acetic acid and alcohols |
-
1957
- 1957-03-13 GB GB832257A patent/GB806769A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012021965A1 (en) * | 2010-08-20 | 2012-02-23 | Enerkem, Inc. | Production of acetates from acetic acid and alcohols |
| CN103201249A (en) * | 2010-08-20 | 2013-07-10 | 埃讷肯公司 | Production of acetates from acetic acid and alcohols |
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