CN105906518A - Plant growth regulator fumaric bisdiethylamino ethanol ester citrate compound and preparation method thereof - Google Patents
Plant growth regulator fumaric bisdiethylamino ethanol ester citrate compound and preparation method thereof Download PDFInfo
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- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
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Abstract
The invention relates to a plant growth regulator fumaric bisdiethylamino ethanol ester citrate compound and a preparation method thereof. The structure of the compound is disclosed in the specification. The preparation method comprises the following steps: adding fumaric acid, N,N-diethylaminoethanol, a catalyst and an organic solvent into a reactor provided with a water separator and a reflux unit, carrying out reflux water-separation reaction at 110-150 DEG C to obtain fumaric bisdiethylamino ethanol ester, and salifying the fumaric bisdiethylamino ethanol ester and double moles of citric acid in the co-thermofusion state to obtain the white powdery solid product. The compound has an obvious promotion action of rooting and germination of seeds, can enhance the stress tolerance of the seeds, and has the advantages of high activity, mildewproof and bactericidal actions, no toxicity and environment friendliness. The preparation method has the advantages of simple production technique and low cost, and can easily implement industrial production.
Description
Technical field
The present invention relates to double Diethylaminoethanol ester citrate compound of a kind of new plant growth regulator fumaric acid and its production and use.This compound has promotion seed germination, promotes plant growing, strengthens photosynthesis, improves crop yield, improves fruit quality, strengthen stress resistance of plant and improve the purposes such as plant disease and pest resistance ability.
Background technology
Along with the development of science and technology, the plant growth regulator of all kinds of synthetic has been increasingly being applied to agricultural production, growth and development of plants serves effective regulation and control action, can improve plant products to a certain extent, improve quality.Apply the growth promoter of synthetic earlier, have heteroauxing class, α-naphthaleneacetic acid class, chlorobenzene fluoroacetic acid class etc..
That existing market application is more is DCPTA N, N-diethyl-2-(3,4-dichlorophenoxy) ethamine (DCPTA) and caproic acid Diethylaminoethanol ester (DA-6), inventor finds to have in both structures diethylamino ethoxy group, illustrates that this group has certain facilitation for plant growing.According to " principle of hybridization ", it is carried out split with the fumaric acid in tricarboxylic acid cycle, i.e. obtain, containing double diethylamino ethoxy structures, there is bioactive compound fumaric acid pair Diethylaminoethanol ester.It is polyfunctional group synergistic structure, and fumaric acid has another name called Fumaric acid, is a kind of important intermedium in tricarboxylic acid cycle, and it generates malic acid with hydrone under the effect of fumarase.Containing two symmetrical α, beta-unsaturated carbonyl structures in the structure of fumaric acid, the derivant being made up of it is respectively provided with good antibacterial activity, the physiologically active of fumaric acid produces cooperative effect with the physiologically active of diethylamino ethoxy so that it is have more excellent plant growth regulation and antibacterial activity.
Summary of the invention
An object of the present invention is that proposing one has the double Diethylaminoethanol ester citrate of bioactive compound fumaric acid.This compound has simple in construction, soluble in water, is easily entered in cyton by cell wall.Having amount of application compared with existing plant growth regulator few, effect is notable, low toxicity, and environmentally safe has the advantages such as antimildew and antibacterial simultaneously, can overcome deficiency of the prior art.
For achieving the above object, present invention employs following technical scheme:
The double Diethylaminoethanol ester citrate compound of a kind of fumaric acid, it is characterised in that the structure of this compound is shown below:
It is another object of the present invention to propose the preparation method of the double Diethylaminoethanol ester citrate of a kind of fumaric acid.Its technique is simple, it is easy to large-scale production, and cheaper starting materials is easy to get, and equipment investment is few, with low cost, and atom utilization is high, and environmental pollution is little, and the method is:
A certain amount of organic solvent is added in the reactor equipped with water knockout drum and reflux, proper catalyst, add fumaric acid and the N of certain mol proportion, N-diethylaminoethanol, the lower heating of stirring, reflux water-dividing reaction 5-9h at a temperature of 110 DEG C～150 DEG C, until separating the water of theoretical amount, Filtration of catalyst, filtrate decompression distills out organic solvent (reclaim and use), the diethylaminoethanol (reclaim and use) of excess and low boilers, bottoms adds the double Diethylaminoethanol ester Theoretical Mass 5%-10% activated decoloration of fumaric acid, stir 30 minutes, filter to obtain the double Diethylaminoethanol ester of pale yellowish oil liquid fumaric acid.Putting in reactor by the citric acid of double for fumaric acid Diethylaminoethanol esters with twice mole again, be heated with stirring to 105 DEG C, after citric acid melts, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white solid product fumaric acid.
Organic solvent is dimethylbenzene or toluene as mentioned above, and its consumption volume milliliter number is 1-8 times of fumaric acid quality grams.
Fumaric acid and N, the N-diethylaminoethanol of certain mol proportion as above are fumaric acid: the mol ratio of N, N-diethylaminoethanol is 1:2-1:3.
Proper catalyst as above is titanyl sulfate, titanium dioxide or silica gel, and its consumption is the 2%-10% of fumaric acid quality grams.
The double Diethylaminoethanol ester of fumaric acid of the present invention is pale yellowish oil liquid, is slightly soluble in water, index of refraction: nD 25=1.6618, density (20 DEG C): 0.5855g/cm3；Productivity is 84.3%～88.0%, and the double Diethylaminoethanol ester citrate of fumaric acid is white powdery solids, and fusing point is 101 DEG C, soluble in water.The preparation principle of the double Diethylaminoethanol ester citrate of fumaric acid is shown below:
Compared with prior art, the invention have benefit that:
(1) containing Liang Ge diethylaminoethanol ester functional group in one molecule of present configuration, with recessive Fumaric acid active body structure carrier each other, atom utilization is high, active function groups superposition, the physiologically active of Fumaric acid produces cooperative effect with the physiologically active of diethylamino ethoxy, it can play excellent plant growth regulation so that it is active effect significantly improves.
(2) the compounds of this invention has promotion seed germination, promotes plant growing, strengthens photosynthesis, improves crop yield, improve fruit quality and strengthen the effect such as stress resistance of plant, and it is of many uses, for broad spectrum type active regulator.
(3) to have consumption few for the compounds of this invention, the advantages such as toxicity is little, free from environmental pollution.
(4) Diethylaminoethanol of the compounds of this invention preparation technology used catalyst and solvent and excess is all directly to reclaim use, does not produce pollution, does not cause waste, belongs to green preparation process.
(5) when catalyst made by the compounds of this invention preparation technology silica gel, self there is decolorization, the decolorization to product can be saved.
(6) the compounds of this invention has mildew-resistant, root system decomposition antibacterial, anti-, is favorably improved plant disease and pest resistance ability.
(7) the compounds of this invention preparation method is simple, and cheaper starting materials is easy to get, low cost, and equipment investment is few, it is easy to large-scale production.
Accompanying drawing explanation
Structure and performance spy in order to further illustrate product provide drawings described below.
Fig. 1 is the infrared spectrogram of fumaric acid Diethylaminoethanol ester；Fig. 1 shows: 2900cm-1Near CH occurs2The stretching vibration of middle c h bond；At 1750cm-1Near occur in that strong absworption peak, correspond to the stretching vibration of ester carbonyl group；At 1350cm-1Near the stretching vibration of C-N-C key occurs；960 cm-1Near the bending vibration of CH=CH key occurs
Fig. 2 is the nuclear magnetic spectrum figure of fumaric acid Diethylaminoethanol ester；Fig. 2 shows: deuterochloroform is solvent, and chemical shift δ 0.98 ~ 1.06 is N-(CH2CH3)2In methyl hydrogen peak；δ 2.50 ~ 2.65 is N-(CH2CH3)2The methylene hydrogen peak being connected with nitrogen；δ 2.72 ~ 2.80 is-OCH2CH2The methylene hydrogen peak that-N is connected with nitrogen；δ 4.24 ~ 4.30 is-OCH2CH2The methylene hydrogen peak that N is connected with oxygen；δ 6.85 ~ 6.90 is the hydrogen peak on CH=CH.
Detailed description of the invention
Below in conjunction with specific embodiment, technical scheme is described further.
Embodiment 1 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 20ml dimethylbenzene, it is heated with stirring to 150 DEG C of back flow reaction 5h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 27.63g of pale yellowish oil liquid fumaric acid, productivity 88.0%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 2 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 23.4 g (0.2mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 40ml dimethylbenzene, it is heated with stirring to 140 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, after decompression distilling off solvent (reclaim and use) and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 26.47g of pale yellowish oil liquid fumaric acid, productivity 84.3%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 3 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.8g titanium dioxide, 20ml dimethylbenzene, it is heated with stirring to 150 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 27.04g of pale yellowish oil liquid fumaric acid, productivity 86.1%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 4 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 0.6g titanyl sulfate, 40ml dimethylbenzene, it is heated with stirring to 140 DEG C of back flow reaction 7h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 26.97g of pale yellowish oil liquid fumaric acid, productivity 85.9%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 5 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 1 g chromatographic silica gel, 40ml dimethylbenzene, it is heated with stirring to 140 DEG C of back flow reaction 6h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 27.41g of pale yellowish oil liquid fumaric acid, productivity 87.3%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 6 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.7g titanyl sulfate, 30ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 6h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 26.75g of pale yellowish oil liquid fumaric acid, productivity 85.2%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 7 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.8g titanium dioxide, 30ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 27.26g of pale yellowish oil liquid fumaric acid, productivity 86.8%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 8 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 23.4 g (0.2mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 40ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 9h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, after decompression distilling off solvent (reclaim and use) and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 26.56g of pale yellowish oil liquid fumaric acid, productivity 84.0%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 9 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 40ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 7h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g active hargil to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 26.97g of pale yellowish oil liquid fumaric acid, productivity 85.9%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Embodiment 10 is adding 11.6g (0.1mol) fumaric acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 1g chromatographic silica gel, 40ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 27.29g of pale yellowish oil liquid fumaric acid, productivity 86.9%.Again the citric acid mix and blend of double for fumaric acid Diethylaminoethanol esters with twice mole being heated to 105 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white powdery solids product fumaric acid.Its fusing point: 101 DEG C.
Table 1 fumaric acid is that main technologic parameters prepared by raw material
| Sequence number | Diethylaminoethanol | Catalyst | Solvent | Temperature DEG C | Time | Productivity % |
| 1 | 35.1g(0.3mol) | 0.8g titanyl sulfate | 20ml dimethylbenzene | 150 | 5h | 88.0% |
| 2 | 23.4g(0.2mol) | 0.8g titanyl sulfate | 40ml dimethylbenzene | 140 | 8h | 84.3% |
| 3 | 35.1g(0.3mol) | 0.8g titanium dioxide | 20ml dimethylbenzene | 150 | 8h | 86.1% |
| 4 | 29.3g(0.25mol) | 0.6g titanyl sulfate | 40ml dimethylbenzene | 140 | 7h | 85.9% |
| 5 | 29.3g(0.25mol) | 1g chromatographic silica gel | 40ml dimethylbenzene | 140 | 6h | 87.3% |
| 6 | 35.1g(0.3mol) | 0.7g titanyl sulfate | 30ml toluene | 110 | 6h | 85.2% |
| 7 | 35.1g(0.3mol) | 0.8g titanium dioxide | 30ml toluene | 110 | 8h | 86.8% |
| 8 | 23.4g(0.2mol) | 0.8g titanyl sulfate | 40ml toluene | 110 | 9h | 84.0% |
| 9 | 29.3g(0.25mol) | 0.8g titanyl sulfate | 40ml toluene | 110 | 7h | 85.9% |
| 10 | 29.3g(0.25mol) | 1g chromatographic silica gel | 40ml toluene | 110 | 8h | 86.9% |
Note: in table 1, fumaric acid inventory is 11.6g (0.1mol).
The Diethylaminoethanol ester citric acid hydrochlorates double to fumaric acid of above-mentioned preparation are used for green vegetable, Semen Glycines, Semen Tritici aestivi, Brassica campestris L, rice paddy seed with reference to " international seed inspection procedure " (1985), " crop seeds inspection procedure " (1995) as evaluating the standard (to grow 1cm for germinateing) whether seed germinates by inventor, having made biological activity test, method of testing is as follows:
Use plate culture, double for fumaric acid Diethylaminoethanol ester citrates are configured to respectively the solution of 100mg/L, 70mg/L, 40mg/L and 10mg/L variable concentrations, study it to green vegetable, Semen Glycines, Semen Tritici aestivi, Brassica campestris L, the growth regulating effect of rice seedling root system.Blank assay is made with distilled water, the DA-6 solution of same concentrations makees standard control group, respectively with the solution soaking green vegetable of respective concentration, Semen Glycines, Semen Tritici aestivi, Brassica campestris L, rice paddy seed 6h 8h, then be respectively placed in temperature be 23 DEG C, 25 DEG C, 20 DEG C, 23 DEG C, 28 DEG C of constant temperature culture rooms measure the length of its root system and stem after cultivating 4d 6d, and add up germination number, calculate germination percentage and regulation percent activity by below equation.
Germination percentage=germinative number/seed sum
A=(N-N0)/N0×100%
A is sample regulation activity
N cultivates the length of the root recorded in compound solution
N0 cultivates the root length degree recorded in distilled water
The double Diethylaminoethanol ester citrate of fumaric acid prepared by the present invention is shown in Table 2 to the data of plant growth regulating activity, table 3, table 4, table 5, table 6:
The double Diethylaminoethanol ester citrate of table 2 fumaric acid is for green vegetable seed (50) Seed germination data
The double Diethylaminoethanol ester citrate of table 3 fumaric acid is for Semen Glycines seed (10) Seed germination data
The double Diethylaminoethanol ester citrate of table 4 fumaric acid is for wheat seed (30) Seed germination data
The double Diethylaminoethanol ester citrate of table 5 fumaric acid is for Semen Brassicae campestris (50) Seed germination data
The double Diethylaminoethanol ester citrate of table 6 fumaric acid is for rice paddy seed (30) Seed germination data
Claims (6)
1. the double Diethylaminoethanol ester citrate compound of a plant growth regulators fumaric acid, it is characterised in that the structure of this compound is shown below:
。
2. the preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators fumaric acid, it is characterised in that the method is:
A certain amount of organic solvent is added in the reactor equipped with the reflux of water knockout drum, proper catalyst, add fumaric acid and the N of certain mol proportion, N-diethylaminoethanol, the lower heating of stirring, reflux water-dividing reaction at a temperature of 110-150 DEG C, until separating the water of theoretical amount, Filtration of catalyst, filtrate decompression distills out organic solvent, the diethylaminoethanol of excess and low boilers, bottoms adds the double Diethylaminoethanol ester Theoretical Mass 5%-10% activated decoloration of fumaric acid, filters to obtain the double Diethylaminoethanol ester of pale yellowish oil liquid fumaric acid；Putting in reactor by the citric acid of double for fumaric acid obtained above Diethylaminoethanol esters with twice mole again, be heated with stirring to 105 DEG C, after citric acid melts, crystallisation by cooling becomes salt, i.e. obtains the double Diethylaminoethanol ester citrate of white solid product fumaric acid.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators fumaric acid the most according to claim 2, it is characterized in that: described organic solvent is dimethylbenzene or toluene, its consumption volume milliliter number is 1-8 times of fumaric acid quality grams.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators fumaric acid the most according to claim 2, it is characterized in that: the fumaric acid of described certain mol proportion and N, N-diethylaminoethanol is fumaric acid: the mol ratio of N, N-diethylaminoethanol is 1: 2-1: 3.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators fumaric acid the most according to claim 2, it is characterized in that: described proper catalyst is titanyl sulfate, titanium dioxide or silica gel, its consumption is the 2%-10% of fumaric acid quality.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators fumaric acid the most according to claim 2, it is characterized in that: described Filtration of catalyst, filtrate decompression distill out organic solvent, excess diethylaminoethanol be recovered to catalyst, organic solvent, diethylaminoethanol recycling.
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| CN105906518B (en) | 2018-02-02 |
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