CN109942416A - A kind of preparation method of aroyl chloride - Google Patents
A kind of preparation method of aroyl chloride Download PDFInfo
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- CN109942416A CN109942416A CN201910288448.0A CN201910288448A CN109942416A CN 109942416 A CN109942416 A CN 109942416A CN 201910288448 A CN201910288448 A CN 201910288448A CN 109942416 A CN109942416 A CN 109942416A
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Abstract
The invention discloses a kind of preparation method of aroyl chloride, the aroyl chloride compound is made in aryl carboxylic acid and phosphorus trichloride reaction.This method synthesizes corresponding acyl chlorides using phosphorus trichloride as chlorination reagent, by aryl carboxylic acid, has production cost low, easy to operate, and by-product low toxicity, environmental-friendly, high income is conducive to industrialized production.
Description
Technical field
The present invention relates to a kind of preparation methods of aroyl chloride, belong to fine chemistry industry synthesis field.
Background technique
It is important organic synthesis intermediate through aroyl chloride compound, is widely used in the synthesis such as medicine, pesticide, dyestuff
In.Aroyl chloride is prepared in the preparation of chloride compounds from aromatic carboxylic acids to occupy an important position.Industrial production at present
The method of aroyl chloride mainly prepares aroyl chloride from tri-chlorination benzyl, and there are complicated for operation, energy consumption is high, yield it is low and
The problems such as post-processing is difficult.
And chlorination reagent used in chloride compounds is prepared from aromatic carboxylic acids and specifically includes that thionyl chloride, phosgene, oxalyl chloride
And phosphorus pentachloride etc..However, these chlorination reagents need to be excessively used mostly, there is lower atom utilization, such as two
Chlorination reagents, the chlorine atom peak use rates such as chlorine sulfoxide (reaction 1), phosgene (reaction 2), oxalyl chloride (reaction 3) are no more than 50%,
And when using phosphorus pentachloride (such as reaction 4), chlorine atom utilization rate is even more to be no more than 20%, and generate also adjoint while product
Generate poisonous and harmful substance, such as SO2, CO, HCl and P (O) Cl3Deng, cause separation difficult, higher cost, to equipment requirement compared with
The problems such as height, Safety and Environmental Protection is lower.
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Summary of the invention
In order to solve the problems in the prior art, the object of the present invention is to provide one kind tries by chlorination of phosphorus trichloride
The preparation method of the aroyl chloride of agent, this method synthesize corresponding acyl chlorides using phosphorus trichloride as chlorination reagent, by aryl carboxylic acid, have
Production cost is low, easy to operate, and by-product low toxicity, environmental-friendly, high income is conducive to industrialized production.
To achieve the goals above, the present invention provides a kind of preparation method of aroyl chloride, aryl carboxylic acid and tri-chlorinations
The aroyl chloride compound is made in phosphorus reaction, and reaction equation is as shown in Equation 1:
Preferably, the aryl carboxylic acid is selected from one of following structural formula:
Preferably, the molar ratio of the aryl carboxylic acid and phosphorus trichloride is 3:1.
Preferably, the reaction dissolvent is acetonitrile, toluene or n-hexane, preferably acetonitrile;Aromatic carboxylic acids is in a solvent
Concentration is 1.0mol/L~2mol/L.
Preferably, the reaction temperature is 25~100 DEG C, preferably 60~80 DEG C;Reaction time is at least 6h.
It is preferably, described that reaction solution is filtered, is rotated after reaction, then temperature be 60~150 DEG C, pressure be 1~
Vacuum distillation purification is carried out under conditions of 10mmHg.
Reaction principle:
For PCl in confirmatory reaction33 chlorine atoms be used equally for the acyl chloride reaction in the inventive method, we are to benzene
The solid matter that formic acid and phosphorus trichloride reaction generate has carried out nmr analysis.If PCl33 chlorine atoms both participate in carboxylic acid
Acyl chloride reaction can then react and generate phosphorous acid HPO (OH)2, and phosphorous acid is precipitated due to solubility is extremely low in acetonitrile.Therefore
We carry out nuclear-magnetism characterization to the solid that reaction is precipitated, as shown in Figure 1, by being compared with standard phosphorous acid,31P NMR exists
Peak at 2.16ppm is the characteristic peak of phosphorous acid.In addition, we go back further progress1H NMR test, can be apparent
Ground sees that the feature hydrogen of phosphorous acid is split by P atom and is divided into doublet (7.49ppm and 5.88ppm), to confirmed phosphorous acid
Generation, this also demonstrates PCl33 chlorine atoms both participated in acyl chloride reaction.
The invention has the following advantages:
1) it is the chlorination reagent of aromatic carboxylic acids that the present invention, which selects phosphorus trichloride, is avoided using hypertoxic raw material liquid chlorine, and not
It is same as common acyl chlorides reagent, such as thionyl chloride, phosgene, oxalyl chloride and phosphorus pentachloride need equivalent or excessively make significantly
With the dosage of phosphorus trichloride is only 1/3 times of equivalent of aromatic carboxylic acids, and environmental-friendly, high income is conducive to industrialized production.
2) phosphorous acid that present invention reaction generates is hypotoxicity solid, can be removed through simple filtration, in simultaneous reactions
Solvent can also be recycled after simply steam again, and this method is easy to operate, by-product low toxicity, environmentally protective.
Detailed description of the invention
Fig. 1 is the nuclear-magnetism phosphorus spectrum and hydrogen spectrogram of the solid generated to the reaction of embodiment 1;
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 1;
Fig. 3 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 1;
Fig. 4 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 2;
Fig. 5 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 2;
Fig. 6 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 3;
Fig. 7 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 3;
Fig. 8 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 4;
Fig. 9 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 4;
Figure 10 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 5;
Figure 11 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 5;
Figure 12 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 6;
Figure 13 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 6;
Figure 14 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 7;
Figure 15 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 7;,
Figure 16 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 8;
Figure 17 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 8;
Figure 18 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 9;
Figure 19 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 9;
Figure 20 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 10;
Figure 21 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 10;
Figure 22 is the nucleus magnetic hydrogen spectrum figure of sample made from embodiment 11;
Figure 23 is the nuclear-magnetism carbon spectrogram of sample made from embodiment 11.
Specific embodiment
Following instance is intended to that the invention will be further described, but is not intended to limit the protection scope of the claims in the present invention.
Unless otherwise instructed, raw materials used is commercial product.
Embodiment 1
It in reaction flask, is added benzoic acid (10mmol), under nitrogen atmosphere, phosphorus trichloride (3.3mmol) and second is added
Nitrile (6mL) is stirred to react 6 hours under the conditions of 60 DEG C.After reaction, a large amount of insoluble solids are precipitated in bottle wall.By reaction solution
Filtering is spin-dried for solvent, and the reaction solution after concentration collects 75-100 DEG C of fraction at 1~10mmHg of vacuum degree.Products therefrom is
The liquid of achromaticity and clarificationYield is 88%.
1H NMR(400MHz CDCl3):δ8.12–8.10(m,2H),7.70–7.66(m,1H),7.53–7.49(m,2H);
13C NMR(100MHz CDCl3):δ168.47,135.47,133.30,1131.50,129.08。
Embodiment 2
It in reaction flask, is added p-methylbenzoic acid (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (0.6mL) is stirred to react 6 hours under the conditions of 60 DEG C.After reaction, bottle wall is precipitated largely not
Soluble solids.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 90-110 DEG C at 1~10mmHg of vacuum degree
Fraction.Products therefrom is the liquid of achromaticity and clarificationYield is 84%.
1H NMR(400MHz CDCl3):δ8.01–7.98(m,2H),7.31–7.29(m,2H),2.44(s,3H);
13C NMR(100MHz CDCl3):δ168.17,146.93,131.66,130.65,129.79,21.89。
Embodiment 3
It in reaction flask, is added 4- methoxy benzoic acid (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (0.6mL) is stirred to react 6 hours under the conditions of 60 DEG C.After reaction, bottle wall is precipitated largely not
Soluble solids.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 90-110 DEG C at 1~10mmHg of vacuum degree
Fraction.Products therefrom is the liquid of achromaticity and clarificationYield is 94%.
1H NMR(400MHz CDCl3):δ8.09–8.05(m,2H),6.98–6.94(m,2H),3.90(s,3H);
13C NMR(100MHz CDCl3):δ167.22,165.48,134.09,125.53,114.33,55.84。
Embodiment 4
It in reaction flask, is added 4- methylthio-benzoic acid (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (0.6mL) is stirred to react 6 hours under the conditions of 60 DEG C.After reaction, bottle wall is precipitated largely not
Soluble solids.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 110-130 DEG C at 1~10mmHg of vacuum degree
Fraction.Products therefrom is white solidYield is 95%.
1H NMR(400MHz CDCl3):δ7.99–7.95(m,2H),7.27–7.24(m,2H),2.52(s,3H);
13C NMR(100MHz CDCl3):δ167.63,149.88,131.74,128.96,124.94,14.66。
Embodiment 5
It in reaction flask, is added 4- vinyl benzoic acid (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (0.6mL) is stirred to react 6 hours under the conditions of 60 DEG C.After reaction, bottle wall is precipitated largely not
Soluble solids.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 90-110 DEG C at 1~10mmHg of vacuum degree
Fraction.Products therefrom is the liquid of achromaticity and clarificationYield is 81%.
1H NMR(400MHz CDCl3):δ8.07–8.05(m,2H),7.52–7.50(m,2H),6.80–6.72(m,1H),
5.96–5.91(m,1H),5.50–5.47(m,1H);
13C NMR(100MHz CDCl3):δ167.98,144.44,135.49,132.21,131.95,126.68,
118.55。
Embodiment 6
It in reaction flask, is added parafluorobenzoic acid (1mmol), under nitrogen atmosphere, is added phosphorus trichloride (0.333mmol)
It is stirred to react 24 hours under the conditions of 80 DEG C with acetonitrile (1.0mL).After reaction, a large amount of insoluble solids are precipitated in bottle wall.
Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 60-90 DEG C of fraction at 1~10mmHg of vacuum degree.Gained
Product is the liquid of achromaticity and clarificationYield is 72%.
1H NMR(400MHz CDCl3):δ8.18–8.13(m,2H),7.22–7.16(m,2H);
13C NMR(100MHz CDCl3):δ168.50,167.11,165.92,134.36,134.26,129.63,
129.60,116.51,116.29。
Embodiment 7
It in reaction flask, is added to trifluoromethylbenzoic acid (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (1.0mL) is stirred to react 24 hours under the conditions of 80 DEG C.After reaction, bottle wall is precipitated a large amount of
Insoluble solid.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 60-90 DEG C at 1~10mmHg of vacuum degree
Fraction.Products therefrom is the liquid of achromaticity and clarificationYield is 72%.
1H NMR(400MHz CDCl3): δ 8.24 (d, J=8.3Hz, 2H), 7.78 (d, J=8.4Hz, 2H);
13C NMR(100MHz CDCl3):δ167.66,136.71,136.38,136.33,131.67,126.14,
126.10,124.61,121.89。
Embodiment 8
It in reaction flask, is added paracyanobenzoic acid (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (1.0mL) is stirred to react 24 hours under the conditions of 80 DEG C.After reaction, bottle wall is precipitated a large amount of
Insoluble solid.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 100-120 at 1~10mmHg of vacuum degree
DEG C fraction.Products therefrom is white solidYield is 76%.
1H NMR(400MHz CDCl3):δ8.23–8.20(m,2H),7.84–7.81(m,2H);
13C NMR(100MHz CDCl3):δ167.39,136.65,132.80,131.59,118.67,117.34。
Embodiment 9
It in reaction flask, is added terephthalic acid monomethyl ester (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (1.0mL) is stirred to react 24 hours under the conditions of 80 DEG C.After reaction, bottle wall is precipitated a large amount of
Insoluble solid.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 150-160 at 1~10mmHg of vacuum degree
DEG C fraction.Products therefrom is white solidYield is 79%.
1H NMR(400MHz CDCl3):δ8.18–8.13(m,4H),3.95(s,3H);
13C NMR(100MHz CDCl3):δ167.99,165.69,136.66,135.95,131.26,130.07,
52.80。
Embodiment 10
It in reaction flask, is added to 2- naphthoic acid (1mmol), under nitrogen atmosphere, is added phosphorus trichloride (0.333mmol)
With acetonitrile (0.6mL).Under the conditions of 60 DEG C, it is stirred to react 6 hours.After reaction, a large amount of insoluble solids are precipitated in bottle wall.It will
Reaction solution filtering is spin-dried for solvent, and the reaction solution after concentration collects 150-160 DEG C of fraction at 1~10mmHg of vacuum degree.Gained
Product is white solidYield is 95%.
1H NMR(400MHz CDCl3):δ8.71–8.71(m,1H),8.04–7.97(m,2H),7.69–7.65(m,1H),
δ7.62–7.58(m,1H);
13C NMR(100MHz CDCl3):δ168.48,136.51,134.86,132.35,130.43,130.11,
129.99,128.92,127.92,127.51,125.39。
Embodiment 11
It in reaction flask, is added 2,4,6- trimethylbenzoic acid (1mmol), under nitrogen atmosphere, phosphorus trichloride is added
(0.333mmol) and acetonitrile (1.0mL) is stirred to react 24 hours under the conditions of 80 DEG C.After reaction, bottle wall is precipitated a large amount of
Insoluble solid.Reaction solution filtering is spin-dried for solvent, the reaction solution after concentration collects 100-120 at 1~10mmHg of vacuum degree
DEG C fraction.Products therefrom is colourless liquidYield is 78%.
1H NMR(400MHz CDCl3):δ6.96(s,2H),2.46(s,6H),2.38(s,3H);
13C NMR(100MHz CDCl3):δ170.62,140.73,136.37,132.98,128.73,21.22,19.43。
Embodiment 12
With the preparation method of embodiment 1, difference is only that solvent is toluene, and products therefrom is the liquid of achromaticity and clarificationYield is 63%.
Embodiment 13
With the preparation method of embodiment 1, difference is only that solvent is n-hexane, and products therefrom is the liquid of achromaticity and clarificationYield is 65%.
Embodiment 14
With the preparation method of embodiment 1, difference is only that reaction temperature is 25 DEG C, and products therefrom is the liquid of achromaticity and clarificationYield is 43%.
Embodiment 15
With the preparation method of embodiment 1, difference is only that reaction temperature is 40 DEG C, and products therefrom is the liquid of achromaticity and clarificationYield is 64%.
Embodiment 16
With the preparation method of embodiment 1, difference is only that reaction temperature is 100 DEG C, and products therefrom is the liquid of achromaticity and clarification
BodyYield is 75%.
Claims (8)
1. a kind of preparation method of aroyl chloride, it is characterised in that: the fragrance is made in aryl carboxylic acid and phosphorus trichloride reaction
Chloride compounds, reaction equation are as shown in Equation 1:
2. preparation method according to claim 1, it is characterised in that: the aryl carboxylic acid in following structural formula one
Kind:
3. preparation method according to claim 1 or 2, it is characterised in that: mole of the aryl carboxylic acid and phosphorus trichloride
Than for 3:1.
4. preparation method according to claim 1 or 2, it is characterised in that: the reaction dissolvent be acetonitrile, toluene or just oneself
Alkane, the concentration of aromatic carboxylic acids in a solvent are 1.0mol/L~2mol/L.
5. the preparation method according to claim 4, it is characterised in that: the reaction dissolvent is acetonitrile.
6. preparation method according to claim 1 or 2, it is characterised in that: the reaction temperature is 25~100 DEG C.
7. preparation method according to claim 6, it is characterised in that: the reaction temperature is 60~80 DEG C.
8. preparation method according to claim 1 or 2, it is characterised in that: it is described after reaction, reaction solution through filtering,
Revolving, then vacuum distillation purification is carried out under conditions of 60~150 DEG C of temperature, 1~10mmHg of pressure.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110776415A (en) * | 2019-11-19 | 2020-02-11 | 怀化泰通新材料科技有限公司 | Rapid preparation method of 2-4-6-trimethylbenzoyl chloride |
WO2021209377A1 (en) * | 2020-04-16 | 2021-10-21 | Basf Se | A process for the preparation of 4-cyanobenzoyl chlorides |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3045513A1 (en) * | 1980-12-03 | 1982-07-01 | Chemische Fabrik Kalk GmbH, 5000 Köln | Bromo-myristic ester cpds. prodn. from myristic acid - by conversion to bromide, bromination and esterification |
WO1995013285A1 (en) * | 1993-11-10 | 1995-05-18 | E.I. Du Pont De Nemours And Company | Process for the preparation of phosphorous acid/carboxylic acid mixed anhydrides and anhydrous phosphorous acid |
CN102924320A (en) * | 2012-11-15 | 2013-02-13 | 南京海陵中药制药工艺技术研究有限公司 | Method for preparing nefopam intermediate I |
CN103880987A (en) * | 2014-04-02 | 2014-06-25 | 长沙新宇高分子科技有限公司 | Thioxanthone photoinitiators and preparation method thereof |
CN106232566A (en) * | 2014-04-14 | 2016-12-14 | 日油株式会社 | The manufacture method of fat acyl chloride and fat acyl chloride |
CN107987057A (en) * | 2017-12-21 | 2018-05-04 | 王兆举 | The preparation method of Axitinib and its intermediate |
CN108047031A (en) * | 2017-12-19 | 2018-05-18 | 湖南久日新材料有限公司 | The preparation method of 2,4,6- tri-methyl chlorides and its application for being used to prepare phosphorous photoinitiator |
CN109293697A (en) * | 2018-10-27 | 2019-02-01 | 长沙新宇高分子科技有限公司 | The preparation method of 2,4,6- trimethyl benzoyl diphenyl base phosphine oxide |
-
2019
- 2019-04-11 CN CN201910288448.0A patent/CN109942416A/en active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3045513A1 (en) * | 1980-12-03 | 1982-07-01 | Chemische Fabrik Kalk GmbH, 5000 Köln | Bromo-myristic ester cpds. prodn. from myristic acid - by conversion to bromide, bromination and esterification |
WO1995013285A1 (en) * | 1993-11-10 | 1995-05-18 | E.I. Du Pont De Nemours And Company | Process for the preparation of phosphorous acid/carboxylic acid mixed anhydrides and anhydrous phosphorous acid |
CN102924320A (en) * | 2012-11-15 | 2013-02-13 | 南京海陵中药制药工艺技术研究有限公司 | Method for preparing nefopam intermediate I |
CN103880987A (en) * | 2014-04-02 | 2014-06-25 | 长沙新宇高分子科技有限公司 | Thioxanthone photoinitiators and preparation method thereof |
CN106232566A (en) * | 2014-04-14 | 2016-12-14 | 日油株式会社 | The manufacture method of fat acyl chloride and fat acyl chloride |
CN108047031A (en) * | 2017-12-19 | 2018-05-18 | 湖南久日新材料有限公司 | The preparation method of 2,4,6- tri-methyl chlorides and its application for being used to prepare phosphorous photoinitiator |
CN107987057A (en) * | 2017-12-21 | 2018-05-04 | 王兆举 | The preparation method of Axitinib and its intermediate |
CN109293697A (en) * | 2018-10-27 | 2019-02-01 | 长沙新宇高分子科技有限公司 | The preparation method of 2,4,6- trimethyl benzoyl diphenyl base phosphine oxide |
Non-Patent Citations (2)
Title |
---|
徐徐等: "3,4,5-三甲氧基苯胺的合成研究", 《林产化学与工业》 * |
朱洪法主编: "《催化剂手册》", 31 August 2008, 金盾出版社 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110776415A (en) * | 2019-11-19 | 2020-02-11 | 怀化泰通新材料科技有限公司 | Rapid preparation method of 2-4-6-trimethylbenzoyl chloride |
WO2021209377A1 (en) * | 2020-04-16 | 2021-10-21 | Basf Se | A process for the preparation of 4-cyanobenzoyl chlorides |
CN115298164A (en) * | 2020-04-16 | 2022-11-04 | 巴斯夫欧洲公司 | Process for preparing 4-cyanobenzoyl chlorides |
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