75-99-0

Usage

Uses

Used in Agriculture:
2,2-Dichloropropionic acid is used as a herbicide for the selective control of annual and perennial grass weeds in cropland and noncropland. It is also used as a selective aquatic herbicide.
Used in Various Crops:
2,2-Dichloropropionic acid is used to control grasses in a wide variety of crops, such as corn, potatoes, legume crops, citrus, fruit, and nut trees. It is also used on sugarcane, sugar beets, carrots, asparagus, alfalfa, and flax.
Used in Non-crop Applications:
2,2-Dichloropropionic acid is used in forestry, home gardening, and to control reed and sedge growth in aquatic environments. It is also used in noncrop applications, such as along drainage ditches, railroads, and in industrial areas.
Used as a Sodium or Magnesium Salt:
2,2-Dichloropropionic acid is marketed as the sodium salt or a mixture of the sodium and magnesium salts for its herbicidal properties.

Air & Water Reactions

Soluble in water. Reacts slowly in water to form hydrochloric and pyruvic acids.

Fire Hazard

Combustible. Irritating fumes of hydrochloric acid may form in fire. Volatilizes with steam.

Safety Profile

A corrosive with low toxicity by skin contact. A skin irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl-

Environmental Fate

The mechanism of action of dalapon is the same as for most acids. The acid denatures tissue proteins upon contact. At lower concentrations, the dalapon causes nonlethal yellowing of sensitive plants, which clearly distinguished them from resistant plants. The mode of action of chlorinated aliphatic acids is not known but they probably affect many enzyme pathways. Dalapon is readily absorbed into roots and leaves of plants and then translocated. Lower concentrations will inhibit plant growth and cause leaf chlorosis, followed by necrosis and death. Higher concentrations of dalapon will result in significant necrosis of areas of the plant in contact with dalapon. Although the direct mechanism of these effects has remained elusive, it is thought that dalapon may affect lipid, carbohydrate, and nitrogen metabolism as secondary effects. One prevailing hypothesis for the primary dalapon affect is that dalapon exerts direct effects on plant structural proteins leading to these secondary metabolic outcomes.

Toxicity evaluation

Dalapon is somewhat persistent in soil but does not readily adsorb to soil particles. It can remain active in soil for several months when applied at high rates. In general, dalapon is considered to have low to moderate persistence with detection in soil for 2–8 weeks. Due to its inability to bind to soil particles, dalapon has a relatively high mobility in soil, with leaching possible. Microorganisms in the soil are very efficient at degrading dalapon. The herbicide is usually not found below the first 6 inches of soil layer. Breakdown is relatively rapid and complete, leading to the production of compounds that are not naturally occurring. Soil microorganisms are efficient at degrading dalapon, however, such that dalapon is not typically found in groundwater. High temperatures and increased moisture accelerate dalapon degradation in soil. Dalapon can also be degraded by ultraviolet light. In aquatic environments, dalapon is degraded by microorganisms (most important), hydrolysis, and photolysis. In the absence of microbial degradation, the half-life of dalapon is several months or longer if the water temperature is below 25°C, with the primary hydrolysis product being pyruvate. Dalapon is absorbed by both plant roots and leaves followed by translocation. With high applications, dalapon precipitates and leads to local corrosive effects on plants. Due to the ability of dalapon to be rapidly metabolized and degraded by microorganisms, hydrolyzed to pyruvate, rapidly translocated to plants, and quickly moved through the environment, it is not expected that dalapon will constitute any bioaccumulation hazard.

InChI:InChI=1/C3H4Cl2O2/c1-3(4,5)2(6)7/h1H3,(H,6,7)/p-1

Synthetic route

2,2-dichloropropanal → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With hydrogenchloride; picoline hydrochloride; chlorine In chloroform at 65 - 70℃; for 24h; Oxidation;	95%
With nitric acid; sodium nitrite In dichloromethane at 20℃; for 192h;	66%

4-nitrosotetrahydro-2H-pyran-4-yl 2,2-dichloropropanoate → Tetrahydro-4H-pyran-4-one (29943-42-8) + 2,2-Dichloropropionic acid (75-99-0) + dinitrogen monoxide (10024-97-2)

Conditions	Yield
With water In methanol; aq. phosphate buffer at 20℃; for 24h; pH=7.4; Kinetics; Reagent/catalyst; Sealed tube;	A n/a B n/a C 92%

propionic acid (802294-64-0) → 2,2-Dichloropropionic acid (75-99-0) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With chlorine; pyrographite; propionic acid anhydride at 130℃; under 760.051 Torr; for 2.5h;	A 10.47% B 68.23%

pyruvic acid-(2,2-dichloro-propionic acid )-anhydride → 2,2-Dichloropropionic acid (75-99-0) + 2-oxo-propionic acid (127-17-3)

Conditions	Yield
Zieht schon an der Luft rasch Wasser an und zerfaellt;

(R,S)-2-chloropropionic acid (598-78-7) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With chlorine; phosphorus trichloride at 180℃;
With phosphonic acid; chlorine at 180℃;

2,2-dichloro-propionic acid anilide (56511-21-8) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With hydrogenchloride at 140℃;

p-methoxyphenyl 2,2-dichloropropanoate (75265-14-4) → 2,2-Dichloropropionic acid (75-99-0) + 4-methoxy-phenol (150-76-5)

Conditions	Yield
With hydrogenchloride; water In various solvent(s) at 25℃; Rate constant; Thermodynamic data; Kinetics; var. temps.; ΔG(activ.), ΔH(activ.), ΔS(activ.), ΔCp(activ.);
With hydrogenchloride; water In various solvent(s) at 25℃; Mechanism;
With 2-Butoxyethanol; water at 20 - 48℃; Rate constant; Thermodynamic data; ΔG<*>, ΔH<*>, ΔS<*>, ΔCp<*>; reagents ratio;
With water at 25℃; under 750.06 Torr; Rate constant; Thermodynamic data; hydrolysis, ΔGp(excit.), ΔHp(excit.), ΔSp(excit.), ΔUv(excit.), ΔSv(excit.),solvent and pressure dependence;

2,2-Dichloro-propionic acid p-tolyl ester (75265-14-4) → 2,2-Dichloropropionic acid (75-99-0) + 4-methoxy-phenol (150-76-5)

Conditions	Yield
With at-poly(methacrylic acid) In water at 25℃; Rate constant; Thermodynamic data; Kinetics; ΔG+, ΔH+; further inhibitors;

dichloro-acetic acid (79-43-6) + dimethyl sulfate (77-78-1) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With n-butyllithium; lithium diisopropyl amide 1.) THF, hexane, -78 deg C, 5 min., 2.) room temp., 1 h; Yield given. Multistep reaction;

(R,S)-2-chloropropionic acid (598-78-7) → 2,2-Dichloropropionic acid (75-99-0) + chloropon (3278-46-4) + 2,2,3,3-tetrachloropropanoic acid (39881-29-3)

Conditions	Yield
With chlorine; phosphorus trichloride for 4h; Heating; Yields of byproduct given;	A 9.38 g B n/a C n/a
With chlorine; phosphorus trichloride for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With chlorine; phosphorus trichloride for 4h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2,2-Dichloro-propionic acid 1-phenoxy-ethyl ester → 2,2-Dichloropropionic acid (75-99-0) + acetaldehyde (75-07-0) + phenol (108-95-2)

Conditions	Yield
With water In acetonitrile Rate constant; var. pH;

methyl 2,2-dichloropropionate (17640-02-7) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With lithium hydroxide In water; isopropyl alcohol at -7℃; for 0.25h;

sulfuric acid (7664-93-9) + tris-(1,1-dichloro-ethyl)-[1,3,5]triazine (30362-74-4) → 2,2-Dichloropropionic acid (75-99-0)

2,2-dichloropropionitrile (594-40-1) + sulfuric acid (7664-93-9) → 2,2-Dichloropropionic acid (75-99-0)

nitrile of/the/ 2.2-dichloro-propanoic acid (1) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With sulfuric acid; water at 120℃;

2,2-dichloropropanal (27313-32-2) + chlorine (7782-50-5) → phosgene (75-44-5) + 1,1,1-trichloroethane (71-55-6) + 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
im UV-Licht;

2,2-dichloropropanal (27313-32-2) + acetyl cyclohexanesulfonyl peroxide (3179-56-4) + chlorine (7782-50-5) → phosgene (75-44-5) + 1,1,1-trichloroethane (71-55-6) + 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
at 50 - 60℃;

hydrogenchloride (7647-01-0) + 2,2-dichloro-propionic acid anilide (56511-21-8) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
at 140℃;

water (7732-18-5) + 2,2-dichloro-propionic acid ; silver salt → 2,2-Dichloropropionic acid (75-99-0) + 2-oxo-propionic acid (127-17-3) + chloro silver

1,1,2-trichloropropene (21400-25-9) + H2O, O2 → 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0) + (1Z,3Z)-1,2,3,5,5-Pentachloro-hexa-1,3-diene (97985-55-2) + 2,3-Dichloro-propionic acid 2,3,3-trichloro-propyl ester (97985-62-1)

Conditions	Yield
for 17h; Heating; Irradiation; Further byproducts given. Title compound not separated from byproducts;

2,2-Dichloropropionic acid (75-99-0) → 2,2-dichloropropionyl chloride (26073-26-7)

Conditions	Yield
With thionyl chloride In N-methyl-acetamide	92%
With thionyl chloride
With thionyl chloride for 3h; Heating;	3.8 g

3-(2-aminoethyl)-1H-indol-5-ol (50-67-9) + 2,2-Dichloropropionic acid (75-99-0) → C13H14Cl2N2O2 (1388185-92-9)

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 24h;	89%

2,2-Dichloropropionic acid (75-99-0) + serotonin hydrochloride (153-98-0) → C13H14Cl2N2O2 (1388185-92-9)

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 24h;	88%

Hexamethyldisiloxane (107-46-0) + 2,2-Dichloropropionic acid (75-99-0) → C6H12Cl2O2Si (72406-98-5)

Conditions	Yield
With sulfuric acid In toluene for 4h; Heating;	78%

2,2-dichloropropanal (27313-32-2) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With hydrogenchloride; picoline hydrochloride; chlorine In chloroform at 65 - 70℃; for 24h; Oxidation;	95%
With nitric acid; sodium nitrite In dichloromethane at 20℃; for 192h;	66%

(1,1,2,2-tetrachloro-propyl)-phosphorimidic acid trichloride (17437-57-9) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With water

1,1,3,3-tetrachloro-butan-2-one (27992-53-6) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With sodium hydrogencarbonate

1,1,1,3,3-pentachlorobutanone (64697-39-8) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
With sodium hydroxide

1,1,2-trichloropropene (21400-25-9) + di(p-tolyl) disulfide (103-19-5) → 2,2-Dichloropropionic acid (75-99-0)

Conditions	Yield
for 20.5h; Product distribution; Heating; Irradiation; molybdenum glass flask, effect of glass composition;

1,1,2-trichloropropene (21400-25-9) → 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0) + (Z)-1,1,2,4,5-Pentachloro-hexa-1,4-diene (97985-56-3) + (1Z,3Z)-1,2,3,5,5-Pentachloro-hexa-1,3-diene (97985-55-2)

Conditions	Yield
With water; oxygen for 17h; Heating; Irradiation; Further byproducts given;
for 17h; Heating; Irradiation; Further byproducts given. Title compound not separated from byproducts;

1,1,2-trichloropropene (21400-25-9) → 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0) + (Z)-1,2,4,4,5-Pentachloro-hexa-1,5-diene (97985-57-4) + (1Z,3Z)-1,2,3,5,5-Pentachloro-hexa-1,3-diene (97985-55-2)

Conditions	Yield
for 17h; Heating; Irradiation; Further byproducts given. Title compound not separated from byproducts;

1,1,2-trichloropropene (21400-25-9) → 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0) + (1Z,3Z)-1,2,3,5,5-Pentachloro-hexa-1,3-diene (97985-55-2) + 1,1,2,4,6,6-Hexachloro-hexa-1,5-diene (97985-59-6)

Conditions	Yield
for 17h; Heating; Irradiation; Further byproducts given. Title compound not separated from byproducts;

1,1,2-trichloropropene (21400-25-9) → 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0) + (1Z,3Z)-1,2,3,5,5-Pentachloro-hexa-1,3-diene (97985-55-2) + 1,1,2,4,4,5-Hexachloro-hexa-1,5-diene (97985-58-5)

Conditions	Yield
for 17h; Heating; Irradiation; Further byproducts given. Title compound not separated from byproducts;

1,1,2-trichloropropene (21400-25-9) → 2,2-dichloropropionyl chloride (26073-26-7) + 2,2-Dichloropropionic acid (75-99-0) + (1Z,3Z)-1,2,3,5,5-Pentachloro-hexa-1,3-diene (97985-55-2) + 1,1,2,4,5,6-hexachloro-1,4-hexadiene (101414-14-6)

Conditions	Yield
for 17h; Heating; Irradiation; Yield given. Further byproducts given. Title compound not separated from byproducts;

2,2-Dichloropropionic acid (75-99-0) + N,N'-diphenylphosphorodiamidic chloride (5625-99-0) → N-phenylamidophosphoric acid (1445-36-9) + 2,2-dichloro-propionic acid anilide (56511-21-8)

Conditions	Yield
In benzene for 8h; Heating;	A n/a B 75%

2,2-Dichloropropionic acid (75-99-0) + vinyl phenyl ether (766-94-9) → 2,2-Dichloro-propionic acid 1-phenoxy-ethyl ester

Conditions	Yield
With phosphoric acid for 0.5h; Ambient temperature;	65%

2,2-Dichloropropionic acid (75-99-0) + allyl alcohol (107-18-6) → allyl 2,2-dichloropropionate (100114-38-3)

Conditions	Yield
With thionyl chloride at -10 - 20℃; for 4h; Esterification;	60%

tetrahydropyran-4-one oxime (61128-73-2) + 2,2-Dichloropropionic acid (75-99-0) → 4-nitrosotetrahydro-2H-pyran-4-yl 2,2-dichloropropanoate

Conditions	Yield
With lead(IV) tetraacetate In dichloromethane at 0 - 20℃; for 4h;	58%

1-[({[3,3'-difluoro-2'-(methoxycarbonyl)-1,1'-biphenyl-4-yl]methyl}amino)carbonyl]cyclopropanaminium chloride + 2,2-Dichloropropionic acid (75-99-0) → 4'-({[1-(2,2-dichloro-propionylamino)-cyclopropanecarbonyl]-amino}-methyl)-3,3'-difluoro-biphenyl-2-carboxylic acid methyl ester

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	23%

methanol (67-56-1) + 2,2-Dichloropropionic acid (75-99-0) → methyl 2,2-dichloropropionate (17640-02-7)

Conditions	Yield
With hydrogenchloride

2,3,5-trichloro-6-hydroxy-benzyl alcohol (4752-64-1) + 2,2-Dichloropropionic acid (75-99-0) → 2,2-dichloro-propionic acid-(2,3,5-trichloro-6-hydroxy-benzyl ester) (101080-80-2)

propylene glycol (57-55-6) + 2,2-Dichloropropionic acid (75-99-0) → 1,2-bis-(2,2-dichloro-propionyloxy)-propane (90560-79-5)

Conditions	Yield
With 1,2-dichloro-ethane at 100℃;

1,1'-oxydipropan-2-ol (110-98-5) + 2,2-Dichloropropionic acid (75-99-0) → 1-[2-(2,2-dichloro-propionyloxy)-propoxy]-propan-2-ol

Conditions	Yield
With ethylene glycol at 100℃;

ethanol (64-17-5) + 2,2-Dichloropropionic acid (75-99-0) → 3-ethoxyprop-2-enoic acid (6192-01-4)

Conditions	Yield
With potassium hydroxide

ethanol (64-17-5) + 2,2-Dichloropropionic acid (75-99-0) → ethyl 2,2-dichloropropionate (17640-03-8)

Conditions	Yield
With hydrogenchloride

2,2-dichloropropionitrile (594-40-1) + 2,2-Dichloropropionic acid (75-99-0) → bis-(2,2-dichloro-propionyl)-amine

Conditions	Yield
at 130℃;

2,2-Dichloropropionic acid (75-99-0) + 2-Chlorobenzyl alcohol (17849-38-6) → 2,2-dichloro-propionic acid-(2-chloro-benzyl ester) (103263-91-8)

Conditions	Yield
With 1,2-dichloro-ethane

2,2-Dichloropropionic acid (75-99-0) + 2-(2,4-dichlorophenoxy)ethanol (120-67-2) → 1-(2,4-dichloro-phenoxy)-2-(2,2-dichloro-propionyloxy)-ethane (99984-25-5)

Conditions	Yield
With sulfuric acid; 1,2-dichloro-ethane Entfernen des entstehenden Wassers;

2,2-Dichloropropionic acid (75-99-0) + 2-(2,4,5-trichloro-phenoxy)-ethanol (2122-77-2) → 2,2-dichloro-propionic acid-[2-(2,4,5-trichloro-phenoxy)-ethyl ester] (136-25-4)

Conditions	Yield
With sulfuric acid; 1,2-dichloro-ethane Entfernen des entstehenden Wassers;

2,2-Dichloropropionic acid (75-99-0) + 2-(4-bromophenoxy)ethanol (34743-88-9) → 2,2-dichloro-propionic acid-[2-(4-bromo-phenoxy)-ethyl ester] (99852-98-9)

Conditions	Yield
With 1,2-dichloro-ethane Entfernen des entstehenden Wassers;

2,2-Dichloropropionic acid (75-99-0) + 3,5-dichloro-2-hydroxybenzyl alcohol (6641-02-7) → 2,2-dichloro-propionic acid-(3,5-dichloro-2-hydroxy-benzyl ester) (103501-36-6)

2,2-Dichloropropionic acid (75-99-0) + 2-(4-chloro-2-methylphenoxy)ethanol (36220-29-8) → 1-(4-chloro-2-methyl-phenoxy)-2-(2,2-dichloro-propionyloxy)-ethane (100120-21-6)

Conditions	Yield
With 1,2-dichloro-ethane unter Entfernen des entstehenden H2O;

2,2-Dichloropropionic acid (75-99-0) + rac-((1R,2S,4S)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methanol (1080-25-7, 17280-40-9, 64577-08-8) → (+/-)-2,2-dichloro-propionic acid-(1,4,5,6,7,7-hexachloro-norborn-5-ene-2endo-ylmethyl ester) (118659-28-2)

Conditions	Yield
With 1,2-dichloro-ethane unter Entfernen des entstehenden Wassers;

2,2-Dichloropropionic acid (75-99-0) + 2,3,6-trichloro-benzyl alcohol (100960-29-0) → 2,2-dichloro-propionic acid-(2,3,6-trichloro-benzyl ester) (1444-82-2)

Conditions	Yield
With toluene-4-sulfonic acid; 1,2-dichloro-ethane

2,2-Dichloropropionic acid (75-99-0) + sodium benzenesulfonate (873-55-2) → 1,2-bis(phenylsulfonyl)ethane (599-94-0)

Conditions	Yield
With sodium carbonate

Upstream product

• 598-78-7 (R,S)-2-chloropropionic acid 
• 56511-21-8 2,2-dichloro-propionic acid anilide 
• 17437-57-9 (1,1,2,2-tetrachloro-propyl)-phosphorimidic acid trichloride 
• 27992-53-6 1,1,3,3-tetrachloro-butan-2-one 
• 64697-39-8 1,1,1,3,3-pentachlorobutanone 
• 21400-25-9 1,1,2-trichloropropene 
• 103-19-5 di(p-tolyl) disulfide 
• 75265-14-4 p-methoxyphenyl 2,2-dichloropropionate 
• 75265-14-4 2,2-Dichloro-propionic acid p-tolyl ester 
• 79-43-6 dichloro-acetic acid 
• 77-78-1 dimethyl sulfate 
• 17640-02-7 methyl 2,2-dichloropropionate 
• 27313-32-2 2,2-dichloropropanal 
• 7664-93-9 sulfuric acid 

Downstream Products

• 17640-02-7 methyl 2,2-dichloropropionate 
• 6192-01-4 3-ethoxyprop-2-enoic acid 
• 17640-03-8 ethyl 2,2-dichloropropionate 
• 103263-91-8 2,2-dichloro-propionic acid-(2-chloro-benzyl ester) 
• 99984-25-5 1-(2,4-dichloro-phenoxy)-2-(2,2-dichloro-propionyloxy)-ethane 
• 136-25-4 2,2-dichloro-propionic acid-[2-(2,4,5-trichloro-phenoxy)-ethyl ester] 
• 99852-98-9 2,2-dichloro-propionic acid-[2-(4-bromo-phenoxy)-ethyl ester] 
• 103501-36-6 2,2-dichloro-propionic acid-(3,5-dichloro-2-hydroxy-benzyl ester) 
• 100120-21-6 1-(4-chloro-2-methyl-phenoxy)-2-(2,2-dichloro-propionyloxy)-ethane 
• 1444-82-2 2,2-dichloro-propionic acid-(2,3,6-trichloro-benzyl ester) 
• 599-94-0 1,2-bis(phenylsulfonyl)ethane 
• 13557-25-0 1-(1-chloroethyl)phenyl sulfone 
• 598-79-8 2-Chloroacrylic acid 
• 766-39-2 2,3-Dimethylmaleic anhydride 

Relevant academic research and scientific papers

New acyloxy nitroso compounds with improved water solubility and nitroxyl (HNO) release kinetics and inhibitors of platelet aggregation

New acyloxy nitroso compounds, 4-nitrosotetrahydro-2H-pyran-4-yl 2,2,2-trichloroacetate and 4-nitrosotetrahydro-2H-pyran-4-yl 2,2-dichloropropanoate were prepared. These compounds release HNO under neutral conditions with half-lives between 50 and 120 min, identifying these HNO donors as kinetically intermediate to the much slower acetate derivative and the faster trifluoroacetic acid derivative. These compounds or HNO-derived from these compounds react with thiols, including glutathione, thiol-containing enzymes and heme-containing proteins in a similar fashion to other acyloxy nitroso compounds. HNO released from these acyloxy nitroso compounds inhibits activated platelet aggregation. These acyloxy nitroso compounds augment the range of release for this group of HNO donors and should be valuable tools in the further study of HNO biology.

Promotive effects in α-monochloropropionic acid catalytic synthesis with propionic anhydride

Selective α-chlorination of propionic acid to synthesize α-monochloropropionic acid was investigated in a laboratory-scale at 130 °C at atmospheric total pressure and in the presence of propionic anhydride as catalyst. Sulfuric acid and common Lewis acid were selected as promotive catalysts considering that the acid-catalyzed enolization is the rate determining step in the chlorination reaction of this experiment, also the reaction selectivity and activity were discussed in the presence of promotive catalysts. The studies revealed that the ferric chloride and sulfuric acid all have prominent promotive effects. Typically the amount of α- monochloropropionic acid can reach 96.14 % when 0.07 g of ferric chloride was added. Furthermore, our results demonstrated that the reaction selectivity and activity were dramatically enhanced after introducing Lewis acid as promotive catalysts.

Oxidation of aliphatic 2,2-dichloroalkanals by HNO3 in CH 2Cl2: An easy and eco-friendly route to the corresponding 2,2-dichloroalkanoic acids

A simple, economically convenient, and eco-compatible procedure for the oxidation of 2,2-dichloroalkanals to the corresponding alkanoic acids has been set up, employing HNO3 in CH2O2, in the presence of NaNO2 as catalyst.

pH-independent hydrolysis of 4-nitrophenyl 2,2-dichloropropionate in aqueous micellar solutions: Relative contributions of hydrophobic and electrostatic interactions

The pH-independent hydrolysis of 4-nitrophenyl 2,2-dichloropropionate (NPDCP) in the presence of aqueous micelles of sodium dodecyl sulfate, sodium dodecylbenzene sulfonate, alkyltrimethylammonium chlorides, alkyldimethylbenzylammonium chlorides (alkyl = cetyl and dodecyl) and polyoxyethylene(9) nonylphenyl ether was studied spectrophotometrically. The observed rate constants, kobs, decrease in the following order: bulk water >cationic micelles >anionic micelles >non-ionic micelles. This order is different from that observed for pH-independent hydrolysis of 4-nitrophenyl chloroformate (NPCF), whose reaction is faster in cationic micelles than in bulk water. A proton NMR study on solubilization of a model ester, 4-nitrophenyl 2-chloropropionate, showed that the methylene groups in the middle of the surfactant hydrophobic chain are most affected by the solubilizate. Lower polarity and high ionic strength of interfacial water decrease the rates of hydrolysis of both NPCF and NPDCP, but t he fraction of the former ester that diffuses to the interface is probably higher than that of the latter. Therefore, whereas the (negatively charged) transition state of NPCF is stabilized by cationic interfaces and destabilized by anionic interfaces, that of NPDCP is negligibly affected by ionic interfaces, which explains the observed rate retardation by all ionic micelles. Calculated activation parameters corroborate our explanation.

2,2-dichloroaldehydes and 2,2-dichlorocarboxylic acids from 2- picoline·HCl catalyzed chlorination of aldehydes

An efficient preparation of 2,2-dichloroaldehydes and 2,2- dichlorocarboxylic acids has been achieved by chlorination of aldehydes using 2-picoline hydrochloride as recoverable catalyst.

Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones, promoted by Fe0-FeCl3 or CuCl-TMEDA

The halogen atom transfer radical cyclization of a N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones has been carried out in high yields under mild conditions, in a reaction promoted by CuCl-TMEDA or Fe0-FeCl3 in acetonitrile or N,N-dimethylformamide, respectively.

Kinetics and mechanism of the hydrolysis of 1-aryloxyethyl alkanoates

The kinetics and mechanism of the hydrolysis of 1-aryloxyethyl alkanoates are reported.In acidic media, 18O isotope exchange studies, kinetics, activation parameters and substituent effects point clearly to an AAl-1 mechanism with the formation of an alkoxycarbonium ion as the rate-limiting step.In basic media the data indicate a conventional BAc-2 mechanism through attack of hydroxide ion on the carbonyl carbon.In neutral medium (pH 2.5-8.8) there is a certain amount of conflicting evidence which leads, however, to the proposal that hydrolysis occurs via attack of a water molecule on the acyl carbon as the rate-limiting step.

Method of manufacturing a dry water-soluble herbicidal salt composition

A method of manufacturing a solid, water-soluble herbicidal composition comprising a water-soluble salt of a herbicidal compound is disclosed. The herbicidal compound is a water-insoluble compound that includes a carboxylic acid functionality, such as a phenoxy-substituted carboxylic acid compound or a substituted benzoic acid compound, and is sufficiently pure to form a dry, solid herbicidal salt composition after interaction with a suitable neutralizing base, such as ammonia, an alkylamine, a dialkylamine, a trialkylamine, a hydroxyalkylamine, a dihydroxyalkylamine, an alkaline salt of an alkali metal or a combination thereof. The dry herbicidal salt composition includes at least about 90% by weight of the water-soluble herbicidal salt, and dissolves rapidly and essentially completely in water to form an aqueous herbicidal solution including up to about 75% by weight of the water-soluble herbicidal salt.

Pyridylthio-acylanilide herbicides

Novel herbicidally active pyridylthio-acylanilides of the formula STR1 in which R1, R2 and R3, independently of one another, represent hydrogen, halogen, cyano or trifluoromethyl or alkyl, alkoxy and alkylthio having 1 to 4 carbon atoms in each case, R4 represents halogen, methyl or methoxy, n represents a number 0, 1 or 2, z represents the group (Ia) STR2 or the group (Ib) STR3 where X represents oxygen, sulphur, an N--R10 or N--O--R11 group, or X and Rg tpgether represent the STR4 radical, and the other radicals can have various meanings. Intermediates of the formulae STR5 are also new.

FREE-RADICAL REACTIONS OF 1,1,2-TRICHLOROPROPENE. I. PHOTOOLIGOMERIZATION OF 1,1,2,-TRICHLOROPROPENE

The UV irradiation of 1,1,2-trichloropropene leads to the production of a complex mixture of products with the molecular formulas C6H5Cl5, C6H4Cl6, C6H5Cl7 and also CH3CCl2COOH and CH3CCl2COCl.By chromatomass spectrometry and IR and PMR spectroscopy it was shown that in addition to the acid and the acid chloride the main products are 1,1,2,4,5,6-hexachloro-1,4-hexadiene CCl2=CClCH2CCl=CClCH2Cl and 1,1,2,4,4,5,5-heptachloro-1-hexene CCl2=CClCH2CCl2CCl2CH3.