CN1220988A - Method for synthesising schiff base in the absence of solvent - Google Patents
Method for synthesising schiff base in the absence of solvent Download PDFInfo
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- CN1220988A CN1220988A CN97107243.4A CN97107243A CN1220988A CN 1220988 A CN1220988 A CN 1220988A CN 97107243 A CN97107243 A CN 97107243A CN 1220988 A CN1220988 A CN 1220988A
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- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000002904 solvent Substances 0.000 title abstract description 6
- 239000002262 Schiff base Substances 0.000 title abstract 2
- 150000004753 Schiff bases Chemical class 0.000 title abstract 2
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 19
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical group NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 claims description 9
- -1 (dimethylamino) phenyl aldehyde Chemical class 0.000 claims description 8
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 5
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 claims description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 4
- 235000014493 Crataegus Nutrition 0.000 claims description 4
- 241001092040 Crataegus Species 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 claims description 3
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims description 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 claims description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000007965 phenolic acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 238000000227 grinding Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000002585 base Substances 0.000 description 20
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000003935 benzaldehydes Chemical class 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 239000004570 mortar (masonry) Substances 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 238000007171 acid catalysis Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for synthesizing schiff base without solvent includes grinding arylalderhyde and amine together and laying aside for reaction at ordinary or low temp under the catalysis of acid. Its advantages include simple synthesis process, no need of solvent, no environmental pollution and high purity and output rate of product (85-99%).
Description
The present invention relates to imino-compound, Schiff's base is synthesized in aldehyde and amine condensation specifically.
Schiff's base (Schiff alkali), the especially application of aromatic series Schiff's base is very extensive, and it can be used as acetaldehyde polyreaction and xitix, the catalyzer of halfcystine oxidizing reaction, can be used as the stabilization of gasoline agent, the biologically active agent of antiviral and disease-resistant bacterium, the properties-correcting agent of polyreaction etc.In recent years, it has also obtained important application in organic non linear optical material, light or fields such as thermochromatism material, liquid crystal material.Simultaneously, it also is a class important intermediate of organic synthesis.The synthetic of Schiff's base generally is in ethanol or acetic acid solution, carries out the condensation of amine and aldehyde under the reflux temperature.Because this condensation reaction is a reversible reaction, often reaches balance in the solution.Therefore, usually in reaction system, add entrainer, the water that reaction generates is taken out of reaction system and improved productive rate.In such cases, reaction yield is generally 60～80%, will consume solvent, contaminate environment, consumes energy simultaneously.
The purpose of this invention is to provide a kind ofly under room temperature or low heating temperature, need not the method for the synthetic Schiff's base of solvent.
Technical scheme of the present invention is as follows:
A kind of method of synthetic Schiff's base, it is to wait the aromatic aldehyde and the amine of amount of substance at room temperature to grind evenly, to leave standstill under room temperature or low heating temperature then, it is reacted completely, promptly to obtain Schiff's base.
This method is applicable to liquid or solid-state aromatic aldehyde, as Ortho Nitro Benzaldehyde, and 4-chloro-benzaldehyde, m-nitrobenzaldehyde is to (dimethylamino) phenyl aldehyde, m-hydroxybenzaldehyde, paranitrobenzaldehyde, p-Hydroxybenzaldehyde, salicylic aldehyde, aubepine etc., and liquid amine or solid-state amine are as p-Chlorobenzoic acid amide, para-totuidine, aniline, O-Phenylene Diamine, semicarbazide hydrochloride, the amino antipyrine of 4-etc.
At room temperature grind Deng the solid-state aromatic aldehyde of amount of substance and solid-state amine, some system can be softened gradually, even forms eutectic, continue to grind, form solid again, grind even back and under room temperature or low heating temperature, leave standstill, it is reacted completely, promptly synthetic corresponding Schiff's base.
At room temperature stir Deng the liquid aromatic aldehyde of amount of substance and liquid amine, be transformed into solid-stately gradually, grind evenly then, under room temperature or low heating temperature, leave standstill, it is reacted completely, promptly synthetic corresponding Schiff's base.
It is solid-state in aromatic aldehyde and amine two reactants a kind of reactant being arranged, another kind of is liquid, then earlier solid-state reactants is continued to be ground to completely solidified in the another kind of liquid reactant that grinding at room temperature such as adds then at amount of substance, grind again evenly, under room temperature or low heating temperature, leave standstill, it is reacted completely, promptly synthetic corresponding Schiff's base.
When synthetic method of the present invention existed as micro-acid, reaction can obviously be quickened, i.e. the existence of trace acid has obvious catalysis.Acid can be sulfonic acid, sulfuric acid, hydrochloric acid, phosphoric acid, carboxylic acid, even the weak acid as phenol, and katalysis is also arranged, but preferred acid is tosic acid or sulfuric acid or phosphoric acid, and its katalysis is particularly evident.
Adopt the method for synthetic Schiff's base of the present invention, do not need solvent, do not need reflux.Therefore, reduce cost, reduced pollution, saved the energy.Method of the present invention row simple to operate, easy, safety, can high yield (80～99%), synthesize Schiff's base to high purity.
Further specify the present invention by the following examples.
The synthetic Schiff's base of the substituted benzaldehyde that embodiment 1. is different and the solvent-free condensation of p-Chlorobenzoic acid amide.
(ⅰ) the synthetic Schiff's base of condensation under the Catalyzed by p-Toluenesulfonic Acid:
The structure of Ar is as follows: a. o-O
2NC
6H
4-; B. p-ClC
6H
4-; C.m-O
2NC
6H
4-; D.p-(CH
3)
2NC
6H
4-; E.m-HOC
6H
4-; F.p-O
2NC
6H
4-; E.p-HOC
6H
4-; H.o-HOC
6H
4-; I.p-CH
3OC
6H
4-.
Take by weighing the substituted benzaldehyde 1 (tosic acid of a～i) and 0.1mmol of 10mmol, under the room temperature (25 ℃) in agate mortar ground and mixed even, the p-Chlorobenzoic acid amide that adds 10mmol then, continue to grind 20 minutes, left standstill under room temperature or the low heating temperature 3 hours, and used absolute ethanol washing product 2～3 times, vacuum-drying under the room temperature, weigh, calculate productive rate.(a～physical constant i), productive rate, ultimate analysis, the IR data see Table 1 to compound 3.
(ⅱ) catalyst-free exists down, and Schiff's base is synthesized in condensation:
Take by weighing the substituted benzaldehyde of 10mmol and the p-Chlorobenzoic acid amide of 10mmol, at room temperature in agate mortar, grind, some system can be softened gradually, even forms eutectic, continues to grind then and solidifies, last ground and mixed is even, under 25 ℃, leave standstill back absolute ethanol washing product 2～3 times that react completely, drying, weigh, calculate productive rate.Reacting phenomenon and productive rate saw Table for 2 (comparing with acid catalysis).
Under the embodiment 2. different acid catalysiss (dimethylamino) phenyl aldehyde and the solvent-free condensation of p-Chlorobenzoic acid amide are synthesized Schiff's base.
Take by weighing the acid of 10mmol to (dimethylamino) phenyl aldehyde and 0.1mmol, in agate mortar grinds, grind under 25 ℃ of the room temperatures and mix, the p-Chlorobenzoic acid amide that adds 10mmol then, continue to grind 20 minutes, leave standstill under 25 ℃, back absolute ethanol washing product 2～3 times react completely, dry, weigh, calculate productive rate, it the results are shown in Table 3.
One or two is arranged in embodiment 3. reactants all is liquid replacement aromatic aldehyde and the synthetic Schiff's base of amine condensation.
(ⅰ) take by weighing the salicylic aldehyde of 10mmol, 0.01mmol tosic acid and the aniline of 10mmol place agate mortar at grinding at room temperature, solidify immediately, continue again to grind 20 minutes, left standstill 3 hours at 25 ℃ then, make and react completely, with absolute ethanol washing product 2 times, vacuum-drying is weighed, calculate productive rate, the results are shown in Table 4.
Synthesize corresponding Schiff's base with aubepine and aniline with same procedure, it the results are shown in Table 4.
(ⅱ) take by weighing the salicylic aldehyde of 20mmol, 0.02mmol tosic acid and the O-Phenylene Diamine of 10mmol place agate mortar at grinding at room temperature, solidify immediately, continue again to grind 20 minutes, left standstill 3 hours at 25 ℃ then, make and react completely, with absolute ethanol washing 3 times, vacuum-drying is weighed, calculate productive rate, the results are shown in Table 4.
(ⅲ) with the method for embodiment 1 (ⅰ), synthesize corresponding Schiff's base respectively with to monomethylaniline, semicarbazide hydrochloride, the amino antipyrine condensation of 4-with 4-chloro-benzaldehyde, it the results are shown in Table 4.
The physical constant of table 1 compound 3 (a-i) and infrared signature absorption frequency thereof
*Total reaction time is 3 hours.
*S: strong, m: medium, w: a little less than.
| Compound | Synthesis temperature */℃ | Fusing point/℃ | Productive rate/% | Ultimate analysis (calculated value)/% | ????IR, ???u(C=N)/cm -1 | ||
| ????C | ????H | ????N | |||||
| ????3a | ????25 | ????88.0- ????89.0 | ?92.1 | ????60.08 ????(59.90) | ????3.84 ????(3.49) | ????10.43 ????(10.75) | ????1622.5(m **) |
| ????3b | ????35 | ????111.5- ????112.5 | ?98.4 | ????62.41 ????(62.42) | ????3.70 ????(3.63) | ????5.56 ????(5.60) | ????1625.5(s) |
| ????3c | ????25 | ????85.5- ????86.5 | ?89.4 | ????59.57 ????(59.90) | ????3.38 ????(3.49) | ????10.22 ????(10.75) | ????1608.3(m) |
| ????3d | ????25 | ????154.0- ????154.5 | ?93.5 | ????69.70 ????(69.62) | ????5.76 ????(5.86) | ????10.39 ????(10.83) | ????1610.2(m) |
| ????3e | ????40 | ????135.5- ????137.0 | ?82.0 | ????67.60 ????(67.38) | ????4.13 ????(4.36) | ????5.90 ????(6.05) | ????1621.7(s) |
| ????3f | ????25 | ????131.5- ????132.5 | ?91.2 | ????59.82 ????(59.90) | ????3.50 ????(3.49) | ????10.22 ????(10.75) | ????1624.7(m) |
| ????3g | ????70 | ????197.5- ????198.0 | ?80.1 | ????67.39 ????(67.38) | ????4.41 ????(4.36) | ????5.96 ????(6.05) | ????1610.5(s) |
| ????3h | ????25 | ????102.0- ????103.5 | ?89.3 | ????67.52 ????(67.38) | ????4.84 ????(4.36) | ????6.27 ????(6.05) | ????1610.8(s) |
| ????3i | ????25 | ????92.0- ????93.5 | ?91.0 | ????68.49 ????(68.44) | ????5.05 ????(4.92) | ????5.90 ????(5.72) | ????1620.9(m) |
25 ℃ of following acid catalysis paradimethy laminobenzaldehydes of table 3 and the solvent-free condensation reaction of p-Chlorobenzoic acid amide
*Paradimethy laminobenzaldehyde is 100: 1 with the mol ratio of acid.
*Select from: CRC Handbook of Chemistry and Physics, 1985
The 25 ℃ of different down substituted benzaldehydes of table 2 and the solvent-free condensation reaction of p-Chlorobenzoic acid amide
*P-TsOH represents p-methyl benzenesulfonic acid, and the mol ratio of substituted benzaldehyde and p-methyl benzenesulfonic acid is 100: 1.
| Substituted benzaldehyde (fusing point/℃) | Reaction conditions | Just observed the time of product color | Productive rate/% | |
| Total reaction time | Catalyzer | |||
| ????1a ????(42-43) | 12 hours 3 hours | No p-TsOH * | 4-5min at once | ?91.0 ?92.1 |
| ????1b ????(45-47) | 24 hours 12 hours | No p-TsOH | 5min at once | ?96.0 ?98.8 |
| ????1c ????(56-58) | 12 hours 3 hours | No p-TsOH | ????30-35min ????2-3min | ?90.0 ?89.4 |
| ????1d ????(73-75) | 12 hours 3 hours | No p-TsOH | ????2h10min ????25-30min | ?92.0 ?93.5 |
| ????1e ????(103-105) | 24 hours 12 hours | No p-TsOH | Slowly at once | ?80.0 ?83.1 |
| ????1f ???(105.5-106.5) | 12 hours 3 hours | No p-TsOH | 45min at once | ?89.6 ?91.2 |
| ????1g ???(115-118) | One 24 hours weeks | No p-TsOH | 3 days at once | ?79.4 ?82.6 |
| ????1h ????(liquid) | 12 hours 3 hours | No p-TsOH | ????2-3min ????10-20s | ?90.0 ?89.3 |
| ????1i ????(liquid) | 12 hours 3 hours | No p-TsOH | ????10min ????1min | ?90.8 ?91.0 |
Table 4 acid catalysis aromatic aldehyde and other contain the solvent-free condensation reaction of amino compound
*
| Reactant | Reaction conditions | The fusing point of product/℃ | Productive rate/% | The ultimate analysis of product (calculated value)/% | The IR of product, u (C=N)/cm -1 | ||||
| Aromatic aldehyde | Contain amino compound | Temperature/℃ | Time/h | ????C | ?H | ????N | |||
| 4-chloro-benzaldehyde | To monomethylaniline | ????25 | ????3 | 127.0- 128.0 | ?96.6 | ?73.30 (73.20) | ?5.47 (5.27) | 6.46 (6.10) | 1623.9(m) |
| 4-chloro-benzaldehyde | Semicarbazide hydrochloride | ????80 | ????1.5 | 211.0- 212.0 | ?88.0 | ?48.78 (48.62) | ?4.41 (4.08) | 21.73 (21.62) | 1668.7(s) |
| 4-chloro-benzaldehyde | The amino antipyrine of 4- | ????25 | ????3 | 260.0- 261.5 | ?98.2 | ?66.59 (66.36) | ?5.32 (4.95) | 12.93 (12.90) | 1649.7(s) |
| Salicylic aldehyde | O-Phenylene Diamine ** | ????25 | ????3 | 165.5- 166.5 | ?85.2 | ?75.51 (75.93) | ?5.40 (5.10) | 8.79 (8.85) | 1614.3(s) |
| Salicylic aldehyde | Aniline | ????25 | ????3 | 47.5- 49.0 | ?89.6 | ?79.61 (79.17) | ?5.51 (5.62) | 6.81 (7.10) | 1615.5(s) |
| Aubepine | Aniline | ????25 | ????3 | 54.5- 55.8 | ?87.4 | ?80.25 (79.59) | ?6.40 (6.20) | 6.52 (6.63) | 1621.9(s) |
*Catalyzer is p-TsOH, and the mole of aromatic aldehyde and catalyzer is 100: 1.
*The mol ratio of O-Phenylene Diamine and salicylic aldehyde is 1: 2.
Claims (7)
1. the method for a synthetic Schiff's base is characterized in that leaving standstill under room temperature or low heating temperature then waiting the aromatic aldehyde and the amine of amount of substance to grind evenly, and it is reacted completely, and promptly obtains Schiff's base.
2. the method for synthetic Schiff's base according to claim 1 is characterized in that aromatic aldehyde is solid-state aromatic aldehyde or liquid aromatic aldehyde.
3. the method for synthetic Schiff's base according to claim 1 is characterized in that aromatic aldehyde is an Ortho Nitro Benzaldehyde, 4-chloro-benzaldehyde, m-nitrobenzaldehyde, to (dimethylamino) phenyl aldehyde, m-hydroxybenzaldehyde, paranitrobenzaldehyde, p-Hydroxybenzaldehyde, salicylic aldehyde, aubepine.
4. the method for synthetic Schiff's base according to claim 1 is characterized in that amine is solid-state or liquid amine.
5. the method for synthetic Schiff's base according to claim 1 is characterized in that amine is p-Chlorobenzoic acid amide, para-totuidine, aniline, O-Phenylene Diamine, semicarbazide hydrochloride, the amino antipyrine of 4-.
6. the method for synthetic Schiff's base according to claim 1 is characterized in that the existence of trace acid, but catalysis generates the condensation reaction of Schiff's base.
7. the method for synthetic Schiff's base according to claim 6, the acid that it is characterized in that said katalysis is sulfonic acid, sulfuric acid, hydrochloric acid, phosphoric acid, carboxylic acid, phenolic acid, preferably tosic acid, sulfuric acid or phosphoric acid.
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|---|---|---|---|
| CN97107243.4A CN1220988A (en) | 1997-12-24 | 1997-12-24 | Method for synthesising schiff base in the absence of solvent |
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| CN101440276B (en) * | 2007-11-19 | 2012-12-05 | 中国石化集团河南石油勘探局 | Aquathermolysis catalytic thinner for heavy oil exploration via steam injection and preparation thereof |
| CN103396360A (en) * | 2013-08-26 | 2013-11-20 | 华东理工大学 | Method for preparing primaquine diphosphate |
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