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A novel one-pot homogeneous process for the large scale manufacture of 2-substituted benzimidazoles

A kind of unsubstituted, C4-C6 technology, applied in the homogeneous process of benzimidazole and its field as corrosion inhibitor for example, can solve the problem of processing and separation step yield loss, large capital investment, prolong reaction and processing time etc.

Active Publication Date: 2020-07-03
ECOLAB USA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthetic methods of the prior art have several disadvantages, such as: 1) prolonged reaction and processing times leading to low throughput per batch; 2) yield loss in processing and separation steps; 3) separation and subsequent drying steps requiring the installation of specialized equipment , thereby requiring substantial capital investment; 4) solid product disposal (whether wet cake or dry powder) involves significant material handling challenges, resulting in yield loss; and 5) final solid product needs to be dried before redissolving in solvent for use in certain applications such as corrosion protection

Method used

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  • A novel one-pot homogeneous process for the large scale manufacture of 2-substituted benzimidazoles
  • A novel one-pot homogeneous process for the large scale manufacture of 2-substituted benzimidazoles
  • A novel one-pot homogeneous process for the large scale manufacture of 2-substituted benzimidazoles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0162] Several condensation reactions between 1,2-phenylenediamine (OPD) and DL-mandelic acid yielded (1H-benzo[d]imidazol-2-yl)(phenyl)methanol at about 30 to about 35 wt% The active material is carried out at 100-110° C. for about 6 to about 8 hours. The effects of various additives (such as high-temperature stable catalysts and co-solvents) on the homogeneity of the reaction were studied, and are listed in Table 1.

[0163] Table 1: Various additives evaluated

[0164]

[0165] *HEG-Cl=hexaethyleneguanidine chloride

[0166] **Ambient temperature

Embodiment 2

[0168] Several experiments were performed using about 5 wt% sulfolane and about 3 wt% acetic acid in the work-up step. The results of HPLC analysis are shown in Table 2. The results clearly show that the reduction in residual OPD concentration is less than about 0.1 wt%, and the resulting material complies with regulations. Active substance refers to the weight percent concentration of OPD and DL-mandelic acid at the beginning of the reaction.

[0169] Charge methanesulfonic acid, sulfolane, and water into a round bottom flask equipped with a magnetic stirrer, reflux condenser, and temperature probe. DL-mandelic acid (1 equivalent) and 1,2-phenylenediamine (1 equivalent) were added thereto, and the contents of the flask were refluxed at about 100-110° C. for about 6-8 hours. After the reaction was complete, glacial acetic acid (3 wt%) was added and reflux was maintained for about another 1-3 hours. After work-up, additional water was added to adjust the active substance to ...

Embodiment 3

[0172] Example 3: Synthesis of 1H-benzo [d] imidazol-2-yl) (phenyl) methanol

[0173]

[0174] Charge methanesulfonic acid, sulfolane, and water into a flask equipped with a magnetic stirrer, reflux condenser, and temperature probe. To this was added o-phenylenediamine (about 12.96 g, 1 equiv) and DL-mandelic acid (about 19.15, 1.05 equiv), and the contents of the flask were refluxed at about 110°C. After about 8 hours of reflux, about 3 g of acetic acid was added and the reflux was maintained for about 3 hours to obtain the title compound in about 97% yield.

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PUM

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Abstract

2-substituted benzimidazoles and methods of preparing the same are disclosed. The compositions may include a compound or salt thereof, an acid, and a polar aprotic solvent. The compositions may be used to inhibit corrosion of a metal surface in contact with an aqueous system, and provide enhanced protection against corrosion of metals in the aqueous system. Formula (I) is shown in the description.

Description

technical field [0001] The present disclosure generally relates to the synthesis of 2-substituted benzimidazoles and compositions thereof. More specifically, the present disclosure relates to a homogeneous process for the synthesis of 2-substituted benzimidazoles and their use, eg, as corrosion inhibitors. Background technique [0002] Benzimidazoles can be prepared using different synthetic routes. A common route is the acid-catalyzed condensation reaction between diamines and carboxylic acids. This approach mainly focuses on obtaining solid benzimidazoles as isolated end products in moderate to good yields. [0003] These benzimidazoles are mainly synthesized in mineral acids, and the final product is precipitated by adjusting the pH to 7 or 8 using a base. The precipitated product was isolated by filtration and dried in an oven. Synthetic methods of the prior art have several disadvantages, such as: 1) prolonged reaction and processing times leading to low throughput ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D235/08C07D235/12C07D235/18C23F11/14
CPCC07D235/18C07D235/08C07D235/12C07D401/04C23F11/149
Inventor P·切鲁库S·R·史利南J·J·米歇尔斯
Owner ECOLAB USA INC
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