CN1580046A - Process for large-scale preparation of 2-hydroxyethyl pyridine - Google Patents
Process for large-scale preparation of 2-hydroxyethyl pyridine Download PDFInfo
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- CN1580046A CN1580046A CN 200410024127 CN200410024127A CN1580046A CN 1580046 A CN1580046 A CN 1580046A CN 200410024127 CN200410024127 CN 200410024127 CN 200410024127 A CN200410024127 A CN 200410024127A CN 1580046 A CN1580046 A CN 1580046A
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Abstract
The invention refers to the technique to produce 2-ethoxyl pyridine with the scale of industrial production. It chooses the 2-methyl pyridine as the starting material, condensate with the paraformaldehyde with the existence of the catalyzer, benzoic acid, chloroactic acid or acetic acid, to produce the 2-ethoxyl pyridine; keep the weight ratio of 2-methyl pyridine: paraformaldehyde:catalyzer=1:0.03-0.12:0.003-0.012. The reaction condition is as follows: whisk it for between 10h and 30h at the temperature of between 90deg.C and 180deg.C, collect the fractions with boiling range of 60-150deg.C/10-100mm/Hg and get the turnoff of the 2-ethoxyl pyridine. It stops a domestic and is featured by the simple production technique and highe yield. The yield of the 2-methyl pyridine is between 84% and 94.85%.
Description
Technical field
The invention belongs to the preparation of pyridine compounds and their, be specifically related to technical scale and prepare 2-hydroxyethyl pyridine technology.
Background technology
In the prior art, there is not technical scale 2-hydroxyethyl pyridine product-feed.Only making starting raw material by the 2-picoline, producing in the process of 2-vinyl pyridine, reaction has 2-hydroxyethyl pyridine to generate in the middle of it; But prior art is separation of intermediates 2-hydroxyethyl pyridine not, but continues prepared in reaction the finished product 2-vinyl pyridine.
Summary of the invention
The objective of the invention is on the basis of existing technology, separate and acquisition 2-hydroxyethyl pyridine (2-hydroxyethylpyridine) product.
Technical scheme of the present invention is as follows: develop a kind of technical scale and prepare 2-hydroxyethyl pyridine technology, it is characterized in that with the 2-picoline be starting raw material; In the presence of catalyzer phenylformic acid, Mono Chloro Acetic Acid or acetate,, generate 2-hydroxyethyl pyridine with the Paraformaldehyde 96 condensation reaction;
Its process parameters range
(1) weight proportion of raw material is: 2-picoline: Paraformaldehyde 96: catalyzer=1: 0.03～0.12: 0.003～0.012;
(2) reaction conditions: stir 90～180 ℃/10～30h down:
(3) reaction is finished, and 60～150 ℃/10～100mm/Hg of boiling range fraction is collected in underpressure distillation, obtains 2-hydroxyethyl pyridine finished product.
The weight proportion of above-mentioned raw material can be: 2-picoline: Paraformaldehyde 96: catalyzer=1: 0.036～0.096: 0.0024～0.0096.
The weight proportion of above-mentioned raw material can also be: 2-picoline: Paraformaldehyde 96: catalyzer=1: 0.042～0.084: 0.0042～0.0084.Above-mentioned reaction conditions can be to stir 120～160 ℃/20～30h down.
The 2-hydroxyethyl pyridine that above-mentioned technology makes, colourless to light yellow transparent liquid, 187～189 ℃ of atmospheric boiling points, content 〉=98.0%, moisture content≤1%.
The 2-hydroxyethyl pyridine that above-mentioned technology makes is done to be commodity selling separately.
The 2-hydroxyethyl pyridine that above-mentioned technology makes also can use as raw material in preparation 2-vinyl pyridine.
Advantage of the present invention is: production technique is easy, fills the domestic gaps; The yield height can reach 84～94.85% with the 2-picoline rate of collecting.
Embodiment
Embodiment 1 one, reaction equation are as follows:
Two, concrete technological operation
With the 2-picoline is starting raw material, with the Paraformaldehyde 96 condensation reaction, generates 2-hydroxyethyl pyridine in the presence of catalyzer.
1, raw material condition
2-picoline (2-methylpyridine) adopts commercial goods, content 〉=99%, moisture content≤0.2%;
Paraformaldehyde 96 (Paraformaldehyde claims solid formaldehyde again) adopts commercial goods, solid particulate, content 90～95%, formic acid content≤0.03%;
Catalyzer phenylformic acid (benzoic acid, commercially available industrial goods, content 〉=98.5%.
2, weight proportion
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.12: 0.012
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 90.5%, w/w) 12.33kg, pure 11.16kg
Phenylformic acid (content 98.5%; W/w) 1.14kg, pure 1.12kg
3, concrete operations
Dosage 2-picoline, Paraformaldehyde 96 and catalyzer add reactor in the lump, stir down, are warming up to 90 ℃ gradually, the reaction timing is reacted 30h under 90～100 ℃ of normal pressures, reaction is finished, 100～150 ℃/10～100mm/Hg of boiling range fraction is collected in underpressure distillation, obtains 2-hydroxyethyl pyridine finished product.Through gas chromatography determination (adopting area normalization method to calculate each constituent mass degree); Finished product must be measured 117.44kg, content 98.50%, pure 115.68kg, yield 94.05%; Colourless transparent liquid, 187～189 ℃ of atmospheric boiling points, moisture content 0.50%; Finished product adopts conventional 200L Galvanized Iron Drum packing, storage at normal temperature, and the quality guaranteed period is 6 months.
Embodiment 2 catalyzer commercial goods Mono Chloro Acetic Acid (monochloroacetic acid), Monochloro Acetic Acid content 〉=99%, dichloroacetic acid content≤0.5%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.03: 0.003;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 91.5%, w/w) 3.05kg, pure 2.79kg
Mono Chloro Acetic Acid (content 99.5%, w/w) 0.2804kg, pure 0.28kg
90～100 ℃ of temperature of reaction, reaction times 10～12h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 107.52kg, content 98.12%, and pure 105.50kg, in the 2-picoline, yield 85.77%; Light yellow transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 3 catalyzer commercial goods acetate (acetic acid), acetic acid content 〉=96%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.12: 0.003;
The quantity that feeds intake is: 2-picoline (content 99.5%) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 90.5%) 12.33kg, pure 11.16kg
Acetate (content 96.5%) 0.2804kg, pure 0.28kg
170～180 ℃ of temperature of reaction, reaction times 15h, finished product must be measured 115.96kg, content 98.58%, pure 114.31kg, in the 2-picoline, yield 92.94%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 4 catalyzer commercial goods Mono Chloro Acetic Acid, Monochloro Acetic Acid content 〉=99%, dichloroacetic acid content≤0.5%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.03: 0.012;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 91.5%, w/w) 3.05kg, pure 2.79kg
Mono Chloro Acetic Acid (content 99.5%, w/w) 1.122kg, pure 1.12kg
90～100 ℃ of temperature of reaction, reaction times 20h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 105.78kg, content 98.62%, and pure 104.32kg, in the 2-picoline, yield 84.81%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 5 catalyzer commercial goods acetate, content 〉=96%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.12: 0.003;
The quantity that feeds intake is: 2-picoline (content 99.5%) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 90.5%) 12.33kg, pure 11.16kg
Acetate (content 96.5%) 0.2892kg, pure 0.28kg
110～120 ℃ of temperature of reaction, reaction times 10h, finished product must be measured 105.42kg, content 98.32%, pure 103.64kg, in the 2-picoline, yield 84.26%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 6 catalyzer commercial goods phenylformic acid, content 〉=98.5%.
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.096: 0.0024;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 91.5%, w/w) 9.76kg, pure 8.928kg
Phenylformic acid (content 99.5%, w/w) 0.2243kg, pure 0.2232kg
170～180 ℃ of temperature of reaction, reaction times 15h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 105.90kg, content 98.82%, and pure 104.65kg, in the 2-picoline, yield 85.08%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 7 catalyzer commercial goods acetate, content 〉=96%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.036: 0.0096;
The quantity that feeds intake is: 2-picoline (content 99.5%) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 90.5%) 3.70kg, pure 3.348kg
Acetate (content 96.5%) 0.9252kg, pure 0.893kg
130～140 ℃ of temperature of reaction, reaction times 15h, finished product must be measured 112.12kg, content 98.35%, pure 110.27kg, in the 2-picoline, yield 89.65%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 8 catalyzer commercial goods Mono Chloro Acetic Acid, Monochloro Acetic Acid content 〉=99%, dichloroacetic acid content≤0.5%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.096: 0.0024;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 91.5%, w/w) 8.35kg, pure 8.303kg
Mono Chloro Acetic Acid (content 99.5%, w/w) 0.2243kg, pure 0.2232kg
100～110 ℃ of temperature of reaction, reaction times 28h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 109.37kg, content 98.68%, and pure 107.93kg, in the 2-picoline, yield 87.75%; Light yellow transparent liquid, moisture content 0.43%; All the other are with embodiment 1.
Embodiment 9 catalyzer commercial goods phenylformic acid, content 〉=98.5%.
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.084: 0.0042;
The quantity that feeds intake is: 2-picoline (content 99.5%) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 92.5%) 8.4454kg, pure 7.812kg
Phenylformic acid (content 98.5%) 0.3965kg, pure 0.3906kg
120～130 ℃ of temperature of reaction, reaction times 25h, finished product must be measured 110.69kg, content 98.55%, pure 109.09kg, in the 2-picoline, yield 88.69%; Little yellow transparent liquid, moisture content 0.29%; All the other are with embodiment 1.
Embodiment 10 catalyzer commercial goods Mono Chloro Acetic Acid, Monochloro Acetic Acid content 〉=99%, dichloroacetic acid content≤0.5%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.042: 0.0084;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 93.5kg, pure 93.0kg
Paraformaldehyde 96 (content 93.5%, w/w) 4.1775kg, pure 3.906kg
Mono Chloro Acetic Acid (content 99.5%, w/w) 0.7851kg, pure 0.7812kg
160～170 ℃ of temperature of reaction, reaction times 20h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 118.12kg, content 98.11%, and pure 115.88kg, in the 2-picoline, yield 94.21%; Colourless transparent liquid, moisture content 0.79%; All the other are with embodiment 1.
Embodiment 11 catalyzer commercial goods phenylformic acid, content 〉=98.5%.
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.12: 0.012;
The quantity that feeds intake is: 2-picoline (content 99.5%) 935kg, pure 930kg
Paraformaldehyde 96 (content 90.5%) 123.31kg, pure 111.6kg
Phenylformic acid (content 99.5%) 11.216kg, pure 11.16kg
130～140 ℃ of temperature of reaction, reaction times 30h, finished product must be measured 1165.38kg, content 98.77%, pure 1151.05kg, in the 2-picoline, yield 93.58%; Light yellow transparent liquid, moisture content 0.63%; All the other are with embodiment 1.
Embodiment 12 catalyzer commercial goods phenylformic acid, content 〉=98.5%.
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.12: 0.012;
The quantity that feeds intake is: 2-picoline (content 99.5%) 935kg, pure 930kg
Paraformaldehyde 96 (content 90.5%) 123.31kg, pure 111.6kg
Phenylformic acid (content 98.5%) 11.33kg, pure 11.16kg
150～160 ℃ of temperature of reaction, reaction times 10h, finished product must be measured 1170.54kg, content 99.05%, pure 1159.42kg, in the 2-picoline, yield 94.26%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 13 catalyzer commercial goods phenylformic acid, content 〉=98.5%.
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.1: 0.01;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 935kg, pure 930kg
Paraformaldehyde 96 (content 91.5%, w/w) 101.64kg, pure 93kg
Phenylformic acid (content 99.5%, w/w) 9.35kg, pure 9.3kg
170～180 ℃ of temperature of reaction, reaction times 30h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 1177.82kg, content 98.66%, and pure 1162.04kg, in the 2-picoline, yield 94.47%; Little band light yellow transparent liquid, moisture content 0.49%; All the other are with embodiment 1.
Embodiment 14 catalyzer commercial goods acetate, content 〉=96%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.05: 0.005;
The quantity that feeds intake is: 2-picoline (content 99.5%) 935kg, pure 930kg
Paraformaldehyde 96 (content 90.5%) 51.38kg, pure 46.5kg
Acetate (content 96.5%) 4.8186kg, pure 4.65kg
110～120 ℃ of temperature of reaction, reaction times 14h, finished product must be measured 1165.88kg, content 98.37%, pure 1146.88kg, in the 2-picoline, yield 93.24%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 15 catalyzer commercial goods Mono Chloro Acetic Acid, Monochloro Acetic Acid content 〉=99%, dichloroacetic acid content≤0.5%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.11: 0.011;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 935kg, pure 930kg
Paraformaldehyde 96 (content 91.5%, w/w) 111.803kg, pure 102.3kg
Mono Chloro Acetic Acid (content 99.5%, w/w) 10.283kg, pure 10.23kg
150～160 ℃ of temperature of reaction, reaction times 19h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 1175.42kg, content 98.32%, and pure 1155.67kg, in the 2-picoline, yield 93.96%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 16 catalyzer commercial goods acetate, content 〉=96%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.098: 0.0098;
The quantity that feeds intake is: 2-picoline (content 99.5%) 935kg, pure 930kg
Paraformaldehyde 96 (content 90.5%) 100.7071kg, pure 91.14kg
Acetate (content 96.5%) 9.4445kg, pure 9.114kg
170～180 ℃ of temperature of reaction, reaction times 25h, finished product must be measured 1182.86kg, content 98.63%, pure 1166.66kg, in the 2-picoline, yield 94.85%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 17 catalyzer commercial goods Mono Chloro Acetic Acid, Monochloro Acetic Acid content 〉=99%, dichloroacetic acid content≤0.5%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.07: 0.007;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 935kg, pure 930kg
Paraformaldehyde 96 (content 91.5%, w/w) 71.15kg, pure 65.1kg
Mono Chloro Acetic Acid (content 99.5%, w/w) 6.55kg, pure 6.51kg
120～130 ℃ of temperature of reaction, reaction times 20h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 1170.44kg, content 98.50%, and pure 1152.88kg, in the 2-picoline, yield 93.73%; Light yellow transparent liquid, moisture content 0.55%; All the other are with embodiment 1.
Embodiment 18 catalyzer commercial goods acetate, content 〉=96%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.06: 0.006;
The quantity that feeds intake is: 2-picoline (content 99.5%) 935kg, pure 930kg
Paraformaldehyde 96 (content 90.5%) 61.66kg, pure 55.8kg
Acetate (content 96.5%) 5.78kg, pure 5.58kg
130～140 ℃ of temperature of reaction, reaction times 10h, finished product. must measure 1154.03kg, content 98.72%, pure 1139.26kg, in the 2-picoline, yield 92.62%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 19 catalyzer commercial goods phenylformic acid, content 〉=99%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.12: 0.012;
The quantity that feeds intake is: 2-picoline (content 99.5%, w/w) 935kg, pure 930kg
Paraformaldehyde 96 (content 93.5%, w/w) 119.36kg, pure 111.6kg
Phenylformic acid (content 99.5%, w/w) 11.22kg, pure 11.16kg
170～180 ℃ of 2 temperature of reaction, reaction times 20h obtains 2-hydroxyethyl pyridine finished product.Finished product must be measured 1169.77kg, content 98.63%, and pure 1153.74kg, in the 2-picoline, yield 93.80%; Light yellow transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Embodiment 20 catalyzer commercial goods Mono Chloro Acetic Acid, content 〉=99.5%,
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.12: 0.012;
The quantity that feeds intake is: 2-picoline (content 99.5%) 935kg, pure 930kg
Paraformaldehyde 96 (content 93.5%, w/w) 119.36kg, pure 111.6kg
Mono Chloro Acetic Acid (content 99.5%) 11.216kg, pure 11.16kg
160～170 ℃ of temperature of reaction, reaction times 15h, finished product must be measured 1174.43kg, content 98.50%, pure 1156.82kg, in the 2-picoline, yield 94.05%; Colourless transparent liquid, moisture content 0.48%; All the other are with embodiment 1.
Claims (6)
1. a technical scale prepares 2-hydroxyethyl pyridine technology, it is characterized in that with the 2-picoline be starting raw material; In the presence of catalyzer phenylformic acid, Mono Chloro Acetic Acid or acetate,, generate 2-hydroxyethyl pyridine with the Paraformaldehyde 96 condensation reaction;
(1) weight proportion of raw material is:
2-picoline: Paraformaldehyde 96: catalyzer=1: 0.03～0.12: 0.003～0.012;
(2) reaction conditions: stir 90～180 ℃/10～30h down:
(3) reaction is finished, and 60～150 ℃/10～100mm/Hg of boiling range fraction is collected in underpressure distillation, obtains 2-hydroxyethyl pyridine finished product.
2. prepare 2-hydroxyethyl pyridine technology according to the described technical scale of claim 1, it is characterized in that the weight proportion of described raw material is: 2-picoline: Paraformaldehyde 96: catalyzer=1: 0.036～0.096: 0.0024～0.0096.
3. prepare 2-hydroxyethyl pyridine technology according to the described technical scale of claim 1, it is characterized in that the weight proportion of described raw material is: 2-picoline: Paraformaldehyde 96: catalyzer=1: 0.042～0.084: 0.0042～0.0084.
Prepare 2-hydroxyethyl pyridine technology according to the described technical scale of claim 1, it is characterized in that described reaction conditions is to stir 120～160 ℃/20～30h down.
4. prepare 2-hydroxyethyl pyridine technology according to the described technical scale of claim 1, it is characterized in that the 2-hydroxyethyl pyridine that makes by described technology, colourless to light yellow transparent liquid, 187～189 ℃ of atmospheric boiling points, content 〉=98.0%, moisture content≤1%.
5. prepare 2-hydroxyethyl pyridine technology according to the described technical scale of claim 1, it is characterized in that the 2-hydroxyethyl pyridine that described technology makes sells as the merchant is brilliant.
6. prepare 2-hydroxyethyl pyridine technology according to the described technical scale of claim 1, it is characterized in that the 2-hydroxyethyl pyridine that described technology makes, in preparation 2-vinyl pyridine, use as raw material.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675191A (en) * | 2011-03-09 | 2012-09-19 | 淄博张店东方化学股份有限公司 | Separation technology used in 2-vinylpyridine preparation process |
| CN102731372A (en) * | 2012-07-16 | 2012-10-17 | 山东天一化学股份有限公司 | Preparation method of 2-ethoxyl pyridina |
| CN104109114A (en) * | 2014-07-17 | 2014-10-22 | 东南大学 | High-efficiency environment-friendly preparation method of 2-hydroxyethylpyridine |
| CN105237468A (en) * | 2015-10-08 | 2016-01-13 | 济南大学 | New method for synthesizing 2-hydroxyethylpyridine |
| CN106243016A (en) * | 2016-07-30 | 2016-12-21 | 淄博张店东方化学股份有限公司 | Commercial scale prepares 4 ethoxy pyridine techniques |
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2004
- 2004-05-18 CN CN 200410024127 patent/CN1253438C/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675191A (en) * | 2011-03-09 | 2012-09-19 | 淄博张店东方化学股份有限公司 | Separation technology used in 2-vinylpyridine preparation process |
| CN102675191B (en) * | 2011-03-09 | 2014-06-18 | 淄博张店东方化学股份有限公司 | Separation technology used in 2-vinylpyridine preparation process |
| CN102731372A (en) * | 2012-07-16 | 2012-10-17 | 山东天一化学股份有限公司 | Preparation method of 2-ethoxyl pyridina |
| CN104109114A (en) * | 2014-07-17 | 2014-10-22 | 东南大学 | High-efficiency environment-friendly preparation method of 2-hydroxyethylpyridine |
| CN104109114B (en) * | 2014-07-17 | 2016-08-24 | 东南大学 | A kind of preparation method of the 2-ethoxy pyridine of high-efficiency environment friendly |
| CN105237468A (en) * | 2015-10-08 | 2016-01-13 | 济南大学 | New method for synthesizing 2-hydroxyethylpyridine |
| CN106243016A (en) * | 2016-07-30 | 2016-12-21 | 淄博张店东方化学股份有限公司 | Commercial scale prepares 4 ethoxy pyridine techniques |
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| CN1253438C (en) | 2006-04-26 |
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