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Use of ester amides as solvents, ester amides as such, and method for preparing ester amides

A technology of ester amides and uses, applied in the preparation of carboxylic acid amides, botanical equipment and methods, and the preparation of organic compounds, etc.

Active Publication Date: 2014-11-19
RHODIA OPERATIONS SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However without using DMGME

Method used

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  • Use of ester amides as solvents, ester amides as such, and method for preparing ester amides
  • Use of ester amides as solvents, ester amides as such, and method for preparing ester amides
  • Use of ester amides as solvents, ester amides as such, and method for preparing ester amides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0347] Example 1.1-MeOOC-CH 2 -CH 2 -CONMe 2 preparation

[0348] The synthetic route is as follows:

[0349]

[0350] step 1 :

[0351] raw material

[0352] Cyclic anhydride

Methanol (anhydrous)

250g; 2.473mol; Mw: 100.07; 99%

1000ml; 24.73mol, Mw: 32.04; 10 equiv

[0353] The ester acid was obtained by Procedure A.

[0354] Final product = 311 g, yield = 94%.

[0355] GC (Gas Chromatography) Analysis: Area > 99%.

[0356] Step 2

[0357] raw material

[0358]

[0359] The ester / acid chloride was obtained by Procedure B.

[0360] Crude product = 348g

[0361] Step 3

[0362] raw material

[0363]

[0364] The ester / amide ester was obtained by Procedure C.

[0365] Crude product = 402g

[0366] Final product = 218g

[0367] GC analysis (area)>98%

Embodiment 1

[0368] Example 1.2-MeOOC-CH 2 -CH 2 -CH 2 -CONMe 2 preparation

[0369] The synthetic route is as follows:

[0370]

[0371] step 1

[0372] raw material

[0373]

[0374] The ester acid was obtained by procedure A.

[0375] Crude product = 333 g (yellow liquid)

[0376] Final product = 274g

[0377] GC (Gas Chromatography) Analysis: Area > 99%

[0378] Step 2

[0379] raw material

[0380]

[0381] The ester / acid chloride was obtained by Procedure B.

[0382] Crude product = 314 g (red liquid), >99% yield.

[0383] Step 3

[0384] raw material

[0385]

[0386] The ester / amide ester was obtained by Procedure C.

[0387] Crude product = 339g

[0388] Final product = 237 g, yield = 89.6%

[0389] GC analysis (area) > 99%

Embodiment 1

[0390] Example 1.3-MeOOC-A MG -CONMe 2 Synthesis , the synthetic route through the first route is as follows:

[0391]

[0392] step 1

[0393] raw material

[0394] Cyclic anhydride

Methanol

245g; 1.91mol; Mw: 128.13; GC>99%

1500ml

[0395] The acid anhydride was obtained by procedure F.

[0396] The acid ester was obtained by Procedure A.

[0397] Crude product = 302g

[0398] Final product = 261 g, yield = 85.6%

[0399] GC (Gas Chromatography) Analysis: Area > 99% (isomers 58 / 42)

[0400] Step 2

[0401] raw material

[0402] Ester / Acid

Thionyl chloride

261g; 1.432mol, Mw: 160.17,

240ml; 2.86mol; 2 equivalents Mw: 118.97

[0403] The ester / acid chloride was obtained by Procedure B.

[0404] Crude product = 290 g (yellow liquid)

[0405] Step 3

[0406] raw material

[0407]

[0408] The methyl ester dimethylamide was obtained by Procedure C.

[0409] Crude product = 303g (r...

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Abstract

Use of ester amide compound (I) or its mixture, as solvent or coalescence agent, is claimed. Use of ester amide compound of formula (R 1>OOC-A-CONR 2>R 3>) (I) or its mixture, as solvent or coalescence agent, is claimed. R 1>optionally cyclic, aromatic 1-36C hydrocarbon; either R 2>, R 3>optionally cyclic, aromatic 1-36C hydrocarbon (optionally substituted); or R 2>+R 3>optionally substituted ring comprising optionally a heteroatom; and A : 2-12C, preferably 2-4C divalent alkyl. Independent claims are included for: (1) the ester amide compound (I) with the exception of 2-ethyl-N,N-dimethyl-succinamic acid methyl ester, N,N-dimethyl-succinamic acid methyl ester, 4-dimethylcarbamoyl-butyric acid methyl ester, 4-dimethylcarbamoyl-3-methyl-butyric acid methyl ester, N,N-diethyl-2-methyl-succinamic acid ethyl ester, N,N-diethyl-2-methyl-succinamic acid methyl ester, mixture of N,N-diethyl-2-methyl-succinamic acid phenyl ester and 4-diethylcarbamoyl-butyric acid phenyl ester, N,N-diethyl-2-methyl-succinamic acid 1-methoxy-ethyl ester, N,N-diethyl-2-methyl-succinamic acid cyclohexyl ester, N,N-diethyl-2-methyl-succinamic acid phenethyl ester, N,N-diethyl-2-methyl-succinamic acid p-tolyl ester, mixture of 2,N,N-triethyl-succinamic acid propyl ester, 4-diethylcarbamoyl-2-methyl-butyric acid propyl ester and 5-diethylcarbamoyl-pentanoic acid propyl ester, and 4-butylcarbamoyl-3-methyl-butyric acid methyl ester; and (2) the preparations of (I).

Description

technical field [0001] The present invention relates to the use of ester amide compounds as solvents. The present invention also relates to a particularly practical process for the preparation of esteramides. The present invention also relates to novel esteramides which can be used in particular as solvents, eg in phytosanitary formulations. Background technique [0002] Various chemical compounds are used in industry as solvents, for example for the preparation of chemical products and materials, for formulating chemical compounds, or for treating surfaces. For example, solvents are used to formulate phytosanitary actives, especially in the form of emulsifiable concentrates (Emulsifiable Concentrate "EC") to be diluted in water by the agricultural operator prior to application to the field. [0003] The industry is looking for new compounds that allow modification or optimization of products and processes in which solvents, especially polar solvents, are used. In particu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N25/02C07C231/02C07C235/74C08K5/20C09D7/12C11D7/50
CPCC11D7/5013C09D7/001C11D3/43C11D7/3263C08K5/20C07C231/14C07C231/02A01N25/02C09D9/005C07C235/74C07C233/05C09D11/033C11D3/32C09D7/20A01N33/22A01N37/26A01N43/653A01N47/22A01N47/24A01N53/00A01N57/12A01N57/16
Inventor O·詹特泽尔M·古格利日
Owner RHODIA OPERATIONS SAS