IES922850A2 - A method and apparatus for producing chlormequat - Google Patents
A method and apparatus for producing chlormequatInfo
- Publication number
- IES922850A2 IES922850A2 IES922850A IES922850A2 IE S922850 A2 IES922850 A2 IE S922850A2 IE S922850 A IES922850 A IE S922850A IE S922850 A2 IES922850 A2 IE S922850A2
- Authority
- IE
- Ireland
- Prior art keywords
- trimethylamine
- ethylene dichloride
- reactor vessel
- stream
- gaseous
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- JUZXDNPBRPUIOR-UHFFFAOYSA-N chlormequat Chemical compound C[N+](C)(C)CCCl JUZXDNPBRPUIOR-UHFFFAOYSA-N 0.000 title description 6
- 239000005974 Chlormequat Substances 0.000 title description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 38
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims abstract description 22
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims abstract description 17
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000010923 batch production Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 239000004381 Choline salt Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000005094 fruit set Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000005082 stem growth Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for producing chlorcholine chloride by reacting trimethylamine and ethylene dichloride both in the gaseous state.
Description
The present invention relates to a method and apparatus for producing chlormequat (chlorcholine chloride) from ethylene dichloride and trimethylamine.
Chlormequat is used as a plant growth regulator which produces various effects with regard to stem growth, flowering, fruit set and tolerance of plants, particularly cereals. For example, it may reduce the amount of extra foliage produced by plants and increase crop yield.
UK Pat. No. 1 092 138 (BASF) teaches the use of mixtures of chlorocholine and choline salts resulting in a shortening of the growth length of plants, an increase In stem wall thickness and a subsequent lessening of lodging of certain types of grain.
At present chlorocholine chloride (CCC) or chlormequat is manufactured by reacting together ethylene dichloride (EDC) and trimethylamine (TMA), with both reactants in liquid form or with EDC in the liquid form and TMA in the gaseous state. In both cases the procedure, for example as outlined in UK 1 138 490 (UCB), is similar.
EDC is usually present in a large excess (although TMA may be used in excess) allowing easy separation of product and unreacted materials. TMA is introduced, in either liquid or gaseous form, to a reactor containing preheated EDC. After heating for a time sufficient to allow the reaction to take place the reaction mixture is cooled.
IE 922850
- 2 Water added before, during or after the reactive step has the effect of transferring the product CCC from the organic or water-immiscible EDC phase, to the aqueous phase. Unreacted TMA remains in the organic phase, which is recycled and reused in the initial reaction step. Activated carbon may be added in a purification step. Any EDC in the aqueous phase is removed by distillation under vacuum and the volume of the product solution is reduced by further distillation. The solution is filtered to remove activated carbon and impurities and transferred to storage.
It is an object of the present invention to provide a method of producing chlormequat from ethylene dichloride and trimethyl amine which combines both the reactants in a gaseous reaction rather than a reaction in the liquid state. This process allows for continuous production rather than batch production. The apparatus for carrying out the method also forms a part of the present invention.
The present invention provides a method of producing chlorcholine chloride from starting materials including trimethylamine and ethylene dichloride, comprising the steps of:
a) separately vapourising ethylene dichloride and trimethylamine to produce two continuous streams in a gaseous state,
b) introducing the ethylene dichloride stream and the trimethylamine stream under pressure to a reactor vessel,
c) accumulating the condensed reaction products,
d) separating the condensed reaction products into organic and aqueous phases, and
e) extracting substantially pure chlorcholine chloride solution from the aqueous phase.
Advantageously, the trimethylamine stream is introduced to the reactor vessel through a nitrogen-shielded injection nozzle to prevent a build-up of solid CCC on the nozzle.
IE 922850
- 3 Recycled ethylene dichloride in the liquid phase is sprayed into the reactor vessel to wholly or partially absorb the heat of reaction between the gaseous reactants by itself vaporising in the reaction zone and absorbing its latent heat of vaporisation.
Preferably, the separation step d) is effected by a counter-current water scrubber, with or without recycling, and with or without chlorcholine chloride or any other agent dissolved in the water.
The gaseous reaction in the reaction vessel is maintained at a temperature of from 80° to 115°C, but more preferably from 100° to 115°C. Suitably, the reaction is effected at approximately atmospheric pressure.
However, the process is not limited to any particular reaction pressure or temperature.
The invention will now be described in further detail, with reference to the accompanying drawings, in which
Figure 1 is a schematic diagram of apparatus for carrying out the process of the invention.
Referring to Figure 1 vapourisers (1) and (2) convert TMA and EDA in their liquid states to the respective gases. Gaseous TMA is superheated, and introduced into the reactor vessel (4) by means of a nitrogen shrouded injection nozzle (3). Gaseous EDC is introduced by means of an injection nozzle (3a). Reaction between said gaseous reactants occurs in or around the vicinity of these nozzles within the confines of the reactor vessel (4). The reactor (4) is thermally insulated and equipped with external heating and cooling means to allow for preheating the reactor before start-up and cooling the reaction during operation. Cooling is also achieved by injection (through nozzles (5)) of recycled EDC as a spray which vaporises in the reaction zone absorbing its latent heat of vaporisation.
Condensed products settle and accumulate at the bottom of the gas/liquid separation area (6). Gaseous products proceed to the
IE 922850
- 4 counter-current water scrubbing tower (7) where excess gaseous EDC is condensed and which dissolves CCC in water and any liquid droplets are removed. The nitrogen flow, which is essentially inert, carries gaseous reactants and products through to the scrubbing tower (7) and is itself scrubbed and removed from the chamber by purge (8). The condensed products in the separation area (6) are thoroughly mixed to ensure that substantially all the CCC becomes dissolved in the aqueous phase, and are then separated into EDC and CCC solutions by a separator (9). The separation will happen easily due to a large difference in density between the phases. A flame trap/demister may also be included because the reactants are flammable.
The reactor is also equipped with nozzle (12) which allow for purging of the apparatus with an inert gas before start-up or washing of the reactor after shut-down.
According to the present invention the process proceeds as a continuous cycle rather than on a batchwise basis. This makes most efficient use of time and apparatus. It is also advantageous in that the CCC product, in the form of an aqueous solution of a concentration of up to about 70% w/w, is likely to be of a high purity, containing substantially less of the by-products associated with the batch process since residence times in the reactor are in the order of minutes in the case of the continuous process, whereas for the batch process they are in the order of hours. Since the product obtained is of high purity the purifying carbon treatment necessitated by the old process (of UK 1,138,490) is not now required. Additional plant can be facilitated to obtain a substantially pure crystaline product from the CCC solution produced.
Claims (6)
1. A method of producing chlorcholine chloride from starting materials including trimethyl amine and ethylene dichloride, comprising
2. A method according to claim 1, in which the trimethylamine stream is introduced to the reactor vessel through a nitrogen-shielded injection nozzle. 25
3. A method according to claim 1 or claim 2, in which recycled ethylene dichoride in the liquid phase is sprayed into the reactor vessel to wholly or partially absorb the heat of reaction between the gaseous reactants. 30
4. A method according to any of claims 1 to 3, wherein the separation step d) is effected by a counter-current water scrubber, with or without recycling, and with or without chlorcholine chloride or any other agent dissolved in the water. IE 922850
5. The steps of: a) separately vapourising ethylene dichloride and trimethylamine to produce two continuous streams in a gaseous state, 10 b) introducing the ethylene dichloride stream and the trimethylamine stream under pressure to a reactor vessel, c) accumulating the condensed reaction products, 15 d) separating the condensed reaction products into organic and aqueous phases, and e) extracting substantially pure chlorcholine chloride solution from the aqueous phase.
6. - 6 5. Apparatus for carrying out a process as claimed in any of the preceding claims, substantially as described herein with reference to, and as shown in the accompanying drawings.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES922850 IES58442B2 (en) | 1991-12-20 | 1992-11-27 | A method and apparatus for producing chlormequat |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE448591A IE914485A1 (en) | 1991-12-20 | 1991-12-20 | A method and apparatus for producing chlormequat |
| IES922850 IES58442B2 (en) | 1991-12-20 | 1992-11-27 | A method and apparatus for producing chlormequat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IES922850A2 true IES922850A2 (en) | 1993-06-30 |
| IES58442B2 IES58442B2 (en) | 1993-09-22 |
Family
ID=26319377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IES922850 IES58442B2 (en) | 1991-12-20 | 1992-11-27 | A method and apparatus for producing chlormequat |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IES58442B2 (en) |
-
1992
- 1992-11-27 IE IES922850 patent/IES58442B2/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IES58442B2 (en) | 1993-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |