CN1298701C - Acrylamide derivative containing ortho-methylthio phenol structure and its preparation method - Google Patents
Acrylamide derivative containing ortho-methylthio phenol structure and its preparation method Download PDFInfo
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- CN1298701C CN1298701C CNB2005100441946A CN200510044194A CN1298701C CN 1298701 C CN1298701 C CN 1298701C CN B2005100441946 A CNB2005100441946 A CN B2005100441946A CN 200510044194 A CN200510044194 A CN 200510044194A CN 1298701 C CN1298701 C CN 1298701C
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- methylthio
- acrylamide
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Abstract
The present invention relates to an acrylamide derivative containing ortho-methylthio phenol structure and a preparation method thereof. When the acrylamide derivative is prepared, under the existence of acidic catalysts, methyl phenol among ortho-methylthio and N-hydroxymethyl acrylamide or N-hydroxymethyl-alpha-methyl acrylamide generate Friedel-Crafts alkylation reaction. The present invention has the advantages that reaction processes are easy to control, one kind of raw material is a chemical industry byproduct, and cost is low; a new vinyl macromolecule monomer which is provided can generate copolymerization reaction with other vinyl monomers to obtain functional polymers applied to the fields of petroleum extraction, water treatment, coating, plastic, textile, papermaking, ore dressing, medicine, agriculture, etc., and meanwhile, the present invention provides an effective way for the comprehensive development and the utilization of the methyl phenol among the ortho-methylthio, namely the chemical industry side product.
Description
Technical field
The present invention relates to a kind of acrylamide derivative, particularly relate to a kind of acrylamide derivative that contains ortho-methylthio phenol structure and preparation method thereof.
Background technology
Methylmercapto m-methyl phenol (being 5-methyl-2-methylthiophenol) is a kind of ortho-methylthio phenol compound, it is the important intermediate by m-methyl phenol and Methyl disulfide prepared in reaction agricultural chemicals---to the main by product in methylthio group m-methyl phenol (the being 3-methyl-4-methylthiophenol) process, its a large amount of generations are important factors that restriction is produced the methylthio group m-methyl phenol.Therefore, press for it is carried out comprehensive development and utilization.
Summary of the invention
The objective of the invention is to develop by product-methylmercapto m-methyl phenol, provide a kind of acrylamide derivative that contains ortho-methylthio phenol structure and preparation method thereof, to satisfy the demand of prior art in the production of methylthio group m-methyl phenol.
A kind of acrylamide derivative that contains ortho-methylthio phenol structure is characterized in that its structural formula is
R is hydrogen or methyl in the formula.
The above-mentioned preparation method who contains the acrylamide derivative of ortho-methylthio phenol structure is characterized in that methylmercapto m-methyl phenol and N hydroxymethyl acrylamide or N-methylol-Alpha-Methyl acrylamide generation Friedel-Crafts alkylated reaction in the presence of an acidic catalyst.
Advantage of the present invention is that reaction process is controlled easily, one of raw material is low for chemical industry by product, cost, a kind of new vinyl polymer monomer is provided, the latter can obtain being applied to the functional polymer in fields such as oil production, water treatment, coating, plastics, weaving, papermaking, ore dressing, medicine, agricultural with other vinyl monomer copolymerization, simultaneously for the chemical industry by product---the comprehensive development and utilization of methylmercapto m-methyl phenol provide one effectively by way of.
Embodiment
During preparation, in water-bath, under the induction stirring, in there-necked flask, add 30.8g (0.2mol) methylmercapto m-methyl phenol (5-methyl-2-methylthiophenol) and 22.2g (0.22mol) N hydroxymethyl acrylamide, 50ml etoh solvent, the 10ml an acidic catalyst vitriol oil successively; Be warming up to 35 ℃, kept under this temperature stirring reaction 7 days, stopped reaction adds ethanol to above-mentioned reaction mixture then, and leaving standstill is that the adularescent precipitation produces.Filter, and wash filter cake with water to neutral, oven dry promptly obtains the acrylamide derivative that contains ortho-methylthio phenol structure of the present invention.The reaction mol ratio of described methylmercapto m-methyl phenol (5-methyl-2-methylthiophenol) and N hydroxymethyl acrylamide is 1: 1～4.Described etoh solvent can be used methyl alcohol, n-propyl alcohol, Virahol, acetate, chloroform or ethyl acetate instead.The described an acidic catalyst vitriol oil can be used phosphoric acid, hydrogenchloride, aluminum chloride, iron trichloride, titanium tetrachloride, tin tetrachloride, H type sulfonated phenylethylene copolymer or H type sulfonated phenol formaldehyde resin instead.Described temperature of reaction can change 10～60 ℃ into for 35 ℃.7 days described reaction times can change 3～10 days into.
The structural formula that contains the acrylamide derivative of ortho-methylthio phenol structure of the present invention is:
With the acrylamide derivative that contains ortho-methylthio phenol structure of the present invention with fusing point, infrared spectra (IR), nucleus magnetic resonance (
1H NMR) method characterizes, and its result is as follows:
Fusing point: 149 ℃.
IR (KBr): 3331cm
-1Be nitrogen-hydrogen stretching vibration absorption peak, 3149cm
-1Be phenolic hydroxyl group stretching vibration absorption peak, 2924,2873cm
-1Be methyl and mesomethylene carbon-hydrogen stretching vibration absorption peak, 1653cm
1Be secondary amide I band stretching vibration absorption peak, 1613,1593,1501,1444cm
-1Be phenyl ring skeleton stretching vibration absorption peak, 1277 is the carbon-oxygen stretching vibration absorption peak of phenol.
1H?NMR(DMSO-D
6)：δ2.15(s，3H，Me-11)，2.40(s，3H，Me-12)，4.23(d，2H，CH
2-10)，5.59(d，1H，H-7)，6.09(d，1H，H-7’)，6.20(m，1H，H-3)，6.62(s，1H)，7.00(s，1H，H-6)，8.31(d，1H，N-H)，9.61(s，1H，O-H)
Claims (3)
1, a kind of acrylamide derivative that contains ortho-methylthio phenol structure is characterized in that its structural formula is
R is hydrogen or methyl in the formula.
2, the described preparation method who contains the acrylamide derivative of ortho-methylthio phenol structure of claim 1 is characterized in that in the presence of an acidic catalyst methylmercapto m-methyl phenol and N hydroxymethyl acrylamide or N-methylol-Alpha-Methyl acrylamide are that 10-60 ℃, the mol ratio of reactant are 1 in temperature of reaction: the Friedel-Crafts alkylated reaction takes place under the condition of 1-4.
3, preparation method as claimed in claim 2 is characterized in that described an acidic catalyst is sulfuric acid, phosphoric acid, hydrogenchloride, aluminum chloride, iron trichloride, titanium tetrachloride, tin tetrachloride, H type sulfonated phenylethylene copolymer or H type sulfonated phenol formaldehyde resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100441946A CN1298701C (en) | 2005-07-28 | 2005-07-28 | Acrylamide derivative containing ortho-methylthio phenol structure and its preparation method |
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| CNB2005100441946A CN1298701C (en) | 2005-07-28 | 2005-07-28 | Acrylamide derivative containing ortho-methylthio phenol structure and its preparation method |
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| Publication Number | Publication Date |
|---|---|
| CN1733716A CN1733716A (en) | 2006-02-15 |
| CN1298701C true CN1298701C (en) | 2007-02-07 |
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| CNB2005100441946A Expired - Fee Related CN1298701C (en) | 2005-07-28 | 2005-07-28 | Acrylamide derivative containing ortho-methylthio phenol structure and its preparation method |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117143379A (en) * | 2023-10-27 | 2023-12-01 | 台州黄岩泽钰新材料科技有限公司 | Antibacterial starch degradable composite material and preparation process thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1171856C (en) * | 2002-12-30 | 2004-10-20 | 中国海洋大学 | Synthetic method for amide derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1171856C (en) * | 2002-12-30 | 2004-10-20 | 中国海洋大学 | Synthetic method for amide derivatives |
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