Carbon Dioxide → HCID 178442911, compound

HRID 1709131Notes

Reaction equation

HRID 1709131 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)(O)O.[NH2:25][NH:26][C:27]([NH2:29])=[NH:28].C1(C)C=CC=CC=1.C(=O)=O>[Ag].O>[C:1]([NH2:25])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:25][NH:26][C:27]([NH2:29])=[NH:28]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 1140TolueneHCID 445639Oleic Acid2×HCID 178513185HCID 178513185, compound2×

Product 1

HCID 178442911HCID 178442911, compound

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 962WaterSolvent

Conditions

Temperature
138 °C

Procedure

The reaction product of oleic acid and aminoguanidine bicarbonate useful as a silver protective agent in the lubricating composition of the present invention is prepared as follows: to a 5-liter, 3-neck flask was added oleic acid (847.5 g, 3 mols), aminoguanidine bicarbonate (408.33 g, 3 mols), 300 ml of toluene, and 15 drops of a silicon anti-foamant. The reaction mixture was heated to reflux under a nitrogen blanket. Vigorous foaming was noted as carbon dioxide gas evolved. When the foaming subsided, water evolution began. A total 57 ml of water was collected from the reaction by means of a Dean-Stark trap. The temperature of the reaction mixture was then raised to approximately 138° C. to facilitate the removal of toluene. To 1,040 g of the product, believed primarily to be oleyl amide of aminoguanidine, was added 1,040 g of process oil. The yellow oil solution was then filtered. Upon standing in air, this solution became red in color and had the following analysis: 3.83% nitrogen; activity, 50%; and Infra-red absorption (cm-1) as follows: 3380-3040 (broad peak); 2920; 2850; 1665; 1530; 1465; and 1400.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under a nitrogen blanket
  3. customA total 57 ml of water was collected from the reaction by means of a Dean-Stark trap
  4. customthe removal of toluene
  5. additionwas added 1,040 g of process oil
  6. filtrationThe yellow oil solution was then filtered
  7. customand Infra-red absorption (cm-1)

Sources & evidence

ORD record
ord-9cde1a9c0dd7422aae352fd914c4ea96
Source dataset
uspto-grants-1990_08
Patent number
US04948523

Reaction notes

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