A method for preparing thiourea derivatives and co-producing mercaptopropionic acid

A technology of thiourea derivatives and mercaptopropionic acid is applied in the directions of mercaptan preparation, organic chemistry, etc., and can solve the problems of restricting the industrial production or application of 3-mercaptopropionic acid, easily generating hydrogen sulfide gas, etc. The effect of mild reaction and simple process flow

Active Publication Date: 2019-09-17
CENT SOUTH UNIV
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  • Abstract
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Problems solved by technology

It is not difficult to find that highly toxic hydrogen sulfide gas may be used in the synthesis of 3-mercaptopropionic acid, or hydrogen sulfide gas (sodium hydrosulfide method) may be easily generated during the synthesis process, or monochloropropionic acid or thiourea, etc. More expensive chemical raw materials, which limit the industrial production or application of 3-mercaptopropionic acid

Method used

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  • A method for preparing thiourea derivatives and co-producing mercaptopropionic acid
  • A method for preparing thiourea derivatives and co-producing mercaptopropionic acid
  • A method for preparing thiourea derivatives and co-producing mercaptopropionic acid

Examples

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Effect test

Embodiment 1

[0036] Example 1 Preparation of N-n-propyl-N'-isopropoxypropyl thiourea

[0037] Add 21.13 parts of S-acrylic acid-N-n-propyl dithiocarbamate with a purity of 99% into the reactor, dissolve 4.07 parts of NaOH in 22.02 parts of water and add to the reactor, start stirring, and observe that the solid disappears Afterwards, the temperature was raised to 65° C., and then 13.14 parts of isopropoxypropylamine was added to react for 2 hours. After the reaction is over, add 19.82 parts of ethyl acetate into the reactor and stir it fully, let the upper layer of organic phase and the lower layer of water phase be separated, take the upper layer of organic phase and carry out vacuum distillation to obtain N-n-propyl-N'-iso Propoxypropylthiourea (infrared spectrum see figure 1 , see H-NMR diagram Figure 6 , spectrogram data are shown in Table 1), and the yield was 95.6%. The pH of the lower aqueous phase was adjusted to 1-2 with HCl, then 19.82 parts of ethyl acetate was added for ext...

Embodiment 2

[0041] Example 2 N, the preparation of N'-di-n-propylthiourea

[0042] 6.44 parts of propylamine were used to replace 13.14 parts of isopropoxypropylamine, and the rest of the conditions were the same as in Example 1 to obtain a yield of 96.5% N, N'-di-n-propylthiourea and a yield of 93.6% of 3-mercaptopropionic acid.

Embodiment 3

[0043] Example 3 Preparation of N-isopropoxypropyl-N'-butoxypropylthiourea

[0044] Add 25.18 parts of S-acrylic acid-N-isopropoxypropyl dithiocarbamate with a purity of 99% into the reactor, dissolve 3.79 parts of NaOH in 20.48 parts of water and add to the reactor, start stirring, and observe After the solution had no stratification, the temperature was raised to 70°C, and then 13.69 parts of butoxypropylamine was added and reacted for 2.5 hours. After the reaction is over, add 18.43 parts of ethyl acetate to the reactor and stir it fully, let it stand and separate the liquid to obtain the upper organic phase and the lower aqueous phase, take the upper organic phase for solvent removal, and obtain N-isopropoxypropyl-N '-butoxypropylthiourea (infrared spectrum see figure 2 ), the yield was 94.9%; the pH of the lower layer of the aqueous phase was adjusted to 1~2 with HCl, then 18.43 parts of ethyl acetate were added for extraction, liquid separation, the organic phase was t...

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Abstract

The invention belongs to the technical field of organic synthesis, and specifically discloses a method for preparing thiourea derivatives and co-producing mercaptopropionic acid. Using S-acrylic acid-dithiocarbamate as raw material, the method is carried out in aqueous phase or organic solvent Aminolysis after neutralization to obtain thiourea derivatives and by-product 3-mercaptopropionate. 3-mercaptopropionate is acidified to produce 3-mercaptopropionic acid. The method for preparing thiourea derivatives and co-producing mercaptopropionic acid of the present invention provides a practical method for the synthesis of thiourea derivatives and 3-mercaptopropionic acid. The method has the advantages of mild reaction, short reaction time, simple process flow, The high yield of thiourea derivatives and 3-mercaptopropionic acid has certain industrial economic value.

Description

technical field [0001] The invention relates to the field of organic chemical industry, in particular to a method for preparing thiourea derivatives and 3-mercaptopropionic acid. Background technique [0002] Thiourea derivatives are in the thiourea molecule NH 2 -C(=S)-NH 2 Based on the introduction of various groups to replace H atoms and form compounds. Because thiourea derivatives contain active atoms such as sulfur or nitrogen, they are widely used in agriculture, medicine, organic synthesis, mineral flotation, and environmental monitoring. [0003] The existing main methods for synthesizing thiourea derivatives are: isothiocyanate method, carbon disulfide method and thiocarbonyl transfer method. (1) Isothiocyanate method, that is to prepare isothiocyanate intermediates with thiocyanates and halides, and then add organic amines to synthesize thiourea (Reeves WP, Simmons JA, Rudis JA.Phase transfer catalysis preparation of aryl thioethers. Synthetic Communications, 1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C335/08C07C335/12C07C323/52C07C319/02C07C319/12
CPCC07C319/02C07C319/12C07C335/08C07C335/12C07C323/52
Inventor 刘广义罗浩
Owner CENT SOUTH UNIV
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