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| CAS No.: | 64-18-6 |
|---|---|
| Name: | Formic acid |
| Article Data: | 2895 |
| Molecular Structure: | |
|
|
|
| Formula: | CH2O2 |
| Molecular Weight: | 46.0257 |
| Synonyms: | Amasil;Ameisensaure;Aminic acid;Bilorin;Collo-Bueglatt;Collo-Didax;Ensilox;Formira;Formisoton;Formylic acid;Hydrogen carboxylicacid;Methanoic acid;Methanoic acid monomer;Myrmicyl;Sybest; |
| EINECS: | 200-579-1 |
| Density: | 1.155 g/cm3 |
| Melting Point: | 8 °C |
| Boiling Point: | 100.56 °C at 760 mmHg |
| Flash Point: | 29.888 °C |
| Solubility: | miscible with water |
| Appearance: | colorless liquid with a pungent odor |
| Hazard Symbols: |
 T,  C,  Xi
|
| Risk Codes: | 23/24/25-34-40-43-35-36/38 |
| Safety: | 36/37-45-26-23-36/37/39 |
| Transport Information: | UN 1198 3/PG 3 |
| PSA: | 37.30000 |
| LogP: | 0.33670 |
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| Conditions | Yield |
|---|---|
| With chlorotris(sodium 3-sulfonatophenyldiphenylphosphine)rhodium(I); hydrogen; sodium formate In water at 50℃; under 75007.5 Torr; for 20h; Inert atmosphere; | 100% |
| With sodium hydrogencarbonate In water for 18h; Reagent/catalyst; Electrochemical reaction; | 93.6% |
| Stage #1: carbon dioxide With phenylsilane In N,N-dimethyl acetamide at 50℃; under 22502.3 Torr; for 4h; pH=Ca. 1.2; Autoclave; Green chemistry; Stage #2: With water In N,N-dimethyl acetamide at 100℃; for 0.25h; Pressure; Temperature; Reagent/catalyst; Time; Green chemistry; | 91% |
| Conditions | Yield |
|---|---|
| Stage #1: methanol With oxygen; nickel dichloride In water at 20℃; for 0.166667h; Flow reactor; Stage #2: With copper(II) sulfate In water at 55℃; for 0.166667h; Flow reactor; | 98% |
| With sodium hydroxide; potassium hexacyanoferrate(III); iridium(III) chloride at 35℃; Rate constant; Thermodynamic data; ΔE, ΔS(excit.), ΔF(excit.); | |
| With dipotassium peroxodisulfate In water at 45℃; Kinetics; Rate constant; Thermodynamic data; mechanism, concentration, temperature, overall energy of activation; |
| Conditions | Yield |
|---|---|
| With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen at 70℃; under 760.051 Torr; for 6h; Solvent; Green chemistry; | A n/a B 96% |
A
- 64-18-6
formic acid
B
- 820963-51-7
3-(tert-butyldiphenylsilanyloxy)-2-methylpropionic acid
| Conditions | Yield |
|---|---|
| With camphor-10-sulfonic acid; dihydrogen peroxide In chloroform-d1 | A 50% B 96% |
- 56153-29-8
formic acid 2-formyloxy-1-methylpropyl ester
A
- 64-18-6
formic acid
B
- 624-64-6
trans-2-Butene
C
- 106-99-0
buta-1,3-diene
D
- 78-93-3
butanone
| Conditions | Yield |
|---|---|
| at 500℃; for 5h; Mechanism; Inert atmosphere; Flow reactor; Pyrolysis; chemoselective reaction; | A 20% B n/a C 94% D n/a |
| Conditions | Yield |
|---|---|
| With pyridine; ozone at 20℃; for 1.16667h; Oxidation; ozonolysis; | A 2% B 2.4% C 2.6% D 93% |
| Conditions | Yield |
|---|---|
| at 160℃; under 99.76 Torr; | A 92% B n/a |
| Conditions | Yield |
|---|---|
| In perchloric acid; water Kinetics; react. at 30 +/- 0.2°C; detection by spectrophotometry; | A 90% B n/a C >99 D n/a |
| Conditions | Yield |
|---|---|
| In perchloric acid; water Kinetics; react. at 30 +/- 0.2°C; detection by spectrophotometry; | A 90% B n/a C >99 D n/a |
- 64-18-6
formic acid
| Conditions | Yield |
|---|---|
| With water at 20℃; for 0.5h; | 90% |
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History
Some alchemists and naturalists were aware that ant hills gave off an acidic vapor as early as the 15th century. The English naturalist,John Ray was the first person to describe the isolation of this substance (by the distillation of large numbers of ants) in 1671. Ants secrete the formic acid for attack and defense purposes.
The French chemist Joseph Gay-Lussac, first synthesized formic acid from hydrocyanic acid . In 1855, another French chemist, Marcellin Berthelot, developed a synthesis from carbon monoxide that is similar to that used today. In the late 1960s, significant quantities of it became available as a byproduct of acetic acid production.
Consensus Reports
Reported in EPA TSCA Inventory.
Standards and Recommendations
OSHA PEL: TWA 5 ppm
ACGIH TLV: 5 ppm; STEL 10 ppm
DFG MAK: 5 ppm (9.5 mg/m3)
DOT Classification: 8; Label: Corrosive
Analytical Methods
For occupational chemical analysis use OSHA: #ID-112 or NIOSH: Formic Acid S173.
Specification
Formic acid (CAS NO.64-18-6) is a flammable colorless fuming liquid with a strong irritating smell, it is soluble in water, ethanol and ether, slightly soluble in benzene. Burning will produce nitrogen oxides emitted toxic fumes. Besides should be stored and transported in low-temperature, drying environment. Separately with bases, oxidizing agents, H hair pore-forming agent, cyanide, sand, water mist, carbon dioxide would be used if emergency.
Physical properties about Formic acid are: (1)ACD/LogP: -0.54; (2)ACD/LogD (pH 5.5): -2.30; (3)ACD/LogD (pH 7.4): -3.94; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2 ; (9)#H bond donors: 1; (10)Index of Refraction:1.342; (11)Molar Refractivity: 8.404 cm3; (12)Molar Volume: 39.867 cm3; (13)Polarizability: 3.331 10-24cm3; (14)Surface Tension: 35.8489990234375 dyne/cm; (15)Density: 1.155 g/cm3; (16)Flash Point: 29.888 °C; (17)Enthalpy of Vaporization: 22.69 kJ/mol; (18)Boiling Point: 100.56 °C at 760 mmHg; (19)Vapour Pressure: 36.4770011901855 mmHg at 25°C
Preparation of Formic acid: Formic acid is often produced as a byproduct in the manufacture of other chemicals, especially acetic acid. But This production is insufficient to meet the present demand for formic acid. In the laboratory, formic acid can be obtained by heating oxalic acid in anhydrous glycerol and extraction by steam distillation. Another preparation (it must be performed under a fume hood) is the acid hydrolysis of ethyl isonitrile using HCl solution:
C2H5NC + 2H2O → C2H5NH2 + HCOOH
Uses of Formic acid: The main use of formic acid is as a preservative and antibacterial agent in livestock feed. Formic acid also can be used in other fields:
1.To process organic latex (sap) into raw rubber.
2.Used in the textile industry and for the tanning of leather.
3.Beekeepers use formic acid as a miticide against the Tracheal (Acarapis woodi) mite and the Varroa mite.
4.Some formate esters are artificial flavorings or perfumes.
5.It is used in laboratories as a solvent modifier for HPLC separations of proteins and peptides, especially when the sample is being prepared for mass spectrometry analysis.
6.In 2006 researchers of EPFL, Switzerland, reported the use of formic acid as a hydrogen storage material.
7.Formic acid is often used as a source of hydride ion in synthetic organic chemistry.
8.In the laboratory, formic acid is also used as source for carbon monoxide.
When you are using this chemical, please be cautious about it as the following:
Wear suitable protective clothing and gloves;
In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer);
Wear suitable protective clothing, gloves and eye/face protection;
You can still convert the following datas into molecular structure:
(1)InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3);
(2)InChIKey=BDAGIHXWWSANSR-UHFFFAOYSA-N;
(3)SmilesC(O)=O;
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | oral | 4gm/kg (4000mg/kg) | AMA Archives of Industrial Health. Vol. 20, Pg. 517, 1959. | |
| dog | LDLo | intravenous | 3gm/kg (3000mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 146, 1955. | |
| man | TCLo | inhalation | 7300ug/m3/8H (7.3mg/m3) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION | Archives of Toxicology. Vol. 66, Pg. 522, 1992. |
| mouse | LC50 | inhalation | 6200mg/m3/15M (6200mg/m3) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 49, 1979. |
| mouse | LD50 | intraperitoneal | 940mg/kg (940mg/kg) | Igiena. Vol. 11, Pg. 507, 1962. | |
| mouse | LD50 | intravenous | 145mg/kg (145mg/kg) | Zeitschrift fuer Ernaehrungswissenschaft. Vol. 9, Pg. 332, 1969. | |
| mouse | LD50 | oral | 700mg/kg (700mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 49, 1979. |
| rabbit | LDLo | intravenous | 239mg/kg (239mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 146, 1955. | |
| rat | LC50 | inhalation | 15gm/m3/15M (15000mg/m3) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 49, 1979. |
| rat | LD50 | oral | 1100mg/kg (1100mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 49, 1979. |
| women | LDLo | oral | 2440ug/kg (2.44mg/kg) | American Journal of Emergency Medicine. Vol. 7, Pg. 286, 1989. | |
| women | LDLo | oral | 2440ug/kg (2.44mg/kg) | BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA VASCULAR: SHOCK | American Journal of Emergency Medicine. Vol. 7, Pg. 286, 1989. |
| women | TDLo | oral | 2200mg/kg (2200mg/kg) | Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 199, 1994. | |
| women | TDLo | oral | 2200mg/kg (2200mg/kg) | KIDNEY, URETER, AND BLADDER: HEMATURIA LUNGS, THORAX, OR RESPIRATION: SPUTUM | Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 199, 1994. |