GB779519A - Process for the production of 2-chloroacrolein and derivatives thereof - Google Patents
Process for the production of 2-chloroacrolein and derivatives thereofInfo
- Publication number
- GB779519A GB779519A GB36635/55A GB3663555A GB779519A GB 779519 A GB779519 A GB 779519A GB 36635/55 A GB36635/55 A GB 36635/55A GB 3663555 A GB3663555 A GB 3663555A GB 779519 A GB779519 A GB 779519A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- dichloropropionaldehyde
- chloroacrolein
- chloro
- ethanol
- 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
- ZWHANXMMZRUTAY-UHFFFAOYSA-N 2-chloroprop-2-enal Chemical compound ClC(=C)C=O ZWHANXMMZRUTAY-UHFFFAOYSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical group CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- DDHSHXNOKGEBMS-UHFFFAOYSA-N 2-chloro-3,3-diethoxyprop-1-ene Chemical compound CCOC(C(Cl)=C)OCC DDHSHXNOKGEBMS-UHFFFAOYSA-N 0.000 abstract 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical group CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- RVSPBCPWLPWULV-UHFFFAOYSA-N ClC(C=O)COCC Chemical compound ClC(C=O)COCC RVSPBCPWLPWULV-UHFFFAOYSA-N 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical group OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2-Chloroacrolein is manufactured by dehydrochlorinating 2:3-dichloropropionaldehyde with hot water in the absence of alkali but in the presence of a primary or secondary monohydric alcohol of not more than 10 carbon atoms per molecule, preferably in an amount at least equal to the weight of 2:3-dichloropropionaldehyde, e.g. in a proportion of 4-8 mols. of alcohol per mol. of 2:3-dichloropropionaldehyde. A preferred procedure consists in introducing 2:3-dichloropropionaldehyde and the alcohol, separately or in admixture, into water (with or without a minor proportion of the alcohol) maintained at refluxing temperature, recovering a condensate containing water, alcohol and 2-chloroacrolein, and dehydrating it. The mixture of alcohol and 2-chloroacrolein may then be distilled to recover the latter, or (when the alcohol is ethanol) may be reacted with additional ethanol to form 2-chloro-1:1:3-trietoxypropane, which may be dehydrochlorinated (e.g. by the action of caustic alkali in the presence of a dehydrating catalyst) to form 1:1:3-triethoxy-2-propene. Examples illustrate the various features of the invention using ethanol as the alcohol. In the example of the preparation of 2-chloro-1:1:3-triethoxypropane, 2 - chloro - 3 - ethoxypropionaldehyde and 2-chloroacrolein diethyl acetal are found as byproducts. Other alcohols specified are methanol, n- and iso-propanols, primary and secondary butanols and pentanols, 2-ethylbutanol, 2-ethylhexanol and cyclohexanol. Starting material. 2:3-Dichloropropionaldehyde is prepared by passing chlorine into a solution of acrolein in carbon tetrachloride at 0 DEG C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US779519XA | 1955-01-06 | 1955-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB779519A true GB779519A (en) | 1957-07-24 |
Family
ID=22140978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36635/55A Expired GB779519A (en) | 1955-01-06 | 1955-12-21 | Process for the production of 2-chloroacrolein and derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB779519A (en) |
-
1955
- 1955-12-21 GB GB36635/55A patent/GB779519A/en not_active Expired
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