Cure accelerators for anaerobic curable compositions, such as adhesives and sealants, are provided, and which are defined with reference to the compounds shown in structure I ##STR00001##
where A is CH.sub.2 or benzyl, R is C.sub.1-10 alkyl, R is H or C.sub.1-10 alkyl, or R and R taken together may form a four to seven membered ring fused to the benzene ring, R is optional, but when R is present, R is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl, and EWG is as shown, an electron withdrawing group, such as nitro, nitrile, carboxylate or trihaloalkyl.

Cure accelerators for anaerobic curable compositions, such as adhesives and sealants, are provided, and which are defined with reference to the compounds shown in structure I ##STR00001##
where A is CH.sub.2 or benzyl, R is C.sub.1-10 alkyl, R is H or C.sub.1-10 alkyl, or R and R taken together may form a four to seven membered ring fused to the benzene ring, R is optional, but when R is present, R is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl, and EWG is as shown, an electron withdrawing group, such as nitro, nitrile, carboxylate or trihaloalkyl.

The present invention relates to a process for preparing ethylenediamine (EDA), where the process comprises the steps a) to c). In step a), formaldehyde is reacted with hydrocyanic acid (HCN) to form formaldehyde cyanohydrin (FACH), where the hydrocyanic acid is completely free or largely free of sulfur dioxide (SO.sub.2). The FACH prepared in this way is reacted with ammonia (NH.sub.3) to form aminoacetonitrile (AAN) in step b), whereupon a hydrogenation of AAN in the presence of a catalyst to form EDA is carried out in step c).

The present invention relates to a process for preparing ethylenediamine (EDA), where the process comprises the steps a) to c). In step a), formaldehyde is reacted with hydrocyanic acid (HCN) to form formaldehyde cyanohydrin (FACH), where the hydrocyanic acid is completely free or largely free of sulfur dioxide (SO.sub.2). The FACH prepared in this way is reacted with ammonia (NH.sub.3) to form aminoacetonitrile (AAN) in step b), whereupon a hydrogenation of AAN in the presence of a catalyst to form EDA is carried out in step c).

The present disclosure generally relates to compounds useful as immunomodulators. Provided herein are compounds, compositions comprising such compounds, and methods of their use. The disclosure further pertains to pharmaceutical compositions comprising at least one compound according to the disclosure that are useful for the treatment of various diseases, including cancer and infectious diseases.

The present invention relates to a process for purifying ethylenediamine (EDA) by distillation, wherein the process comprises the steps a) and b). In step a), a mixture (G1) comprising water, EDA and N-methylethylenediamine (N-MeEDA) is fed into a distillation apparatus (D1), and the major part of the water comprised in the mixture (G1) is separated off overhead at a pressure of greater than 4.8 bara. From the bottom of (D1), the water-enriched mixture (G2) is fed into a distillation apparatus (D2) in step b). At the top of (D2), the major part of the N-MeEDA is distilled off. The stream (S3) obtained from the bottom of (D2) comprises EDA, with the components water and N-MeEDA comprised in the mixture (G1) having been largely or completely removed. Further distillation steps can optionally be carried out in order to obtain pure EDA, for example when diethylenetriamine (DETA) is additionally comprised in the mixture (G1). If ammonia is additionally comprised in the mixture (G1), an ammonia removal is preferably additionally carried out before carrying out the step a) in the process of the invention.

The present invention relates to a process for purifying ethylenediamine (EDA) by distillation, wherein the process comprises the steps a) and b). In step a), a mixture (G1) comprising water, EDA and N-methylethylenediamine (N-MeEDA) is fed into a distillation apparatus (D1), and the major part of the water comprised in the mixture (G1) is separated off overhead at a pressure of greater than 4.8 bara. From the bottom of (D1), the water-enriched mixture (G2) is fed into a distillation apparatus (D2) in step b). At the top of (D2), the major part of the N-MeEDA is distilled off. The stream (S3) obtained from the bottom of (D2) comprises EDA, with the components water and N-MeEDA comprised in the mixture (G1) having been largely or completely removed. Further distillation steps can optionally be carried out in order to obtain pure EDA, for example when diethylenetriamine (DETA) is additionally comprised in the mixture (G1). If ammonia is additionally comprised in the mixture (G1), an ammonia removal is preferably additionally carried out before carrying out the step a) in the process of the invention.

Cure accelerators for anaerobic curable compositions, such as adhesives and sealants, are provided, and which are defined with reference to the compounds shown in structure I

##STR00001##

where A is CH.sub.2 or benzyl, R is C.sub.1-10 alkyl, R is H or C.sub.1-10 alkyl, or R and R taken together may form a four to seven membered ring fused to the benzene ring, R is optional, but when R is present, R is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl, and EWG is as shown, an electron withdrawing group, such as nitro, nitrile, carboxylate or trihaloalkyl.

Cure accelerators for anaerobic curable compositions, such as adhesives and sealants, are provided, and which are defined with reference to the compounds shown in structure I

##STR00001##

where A is CH.sub.2 or benzyl, R is C.sub.1-10 alkyl, R is H or C.sub.1-10 alkyl, or R and R taken together may form a four to seven membered ring fused to the benzene ring, R is optional, but when R is present, R is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl, and EWG is as shown, an electron withdrawing group, such as nitro, nitrile, carboxylate or trihaloalkyl.

Provided is a method of making ethylenediaminetetraacetic acid (EDTA) comprising the steps: (a) providing a reaction mixture (a) comprising ethylenediamine (EDA) and glycolonitrile (GN), wherein reaction mixture (a) comprises 0% to 0.1% by weight, based on the weight of reaction mixture (a), of any base having pKa of the conjugate acid (PKaH) of 13 or higher; (b) causing or allowing reaction mixture (a) to react to form a dinitrile (DN) compound; (c) bringing the DN into contact with aqueous solution of a base having pKaH of 11 or higher, and causing or allowing the resulting mixture to react to form a diacid compound (DA); (d) causing or allowing the DA to react, either sequentially or simultaneously, with additional GN to form products (Pd); (e) causing or allowing products (Pd) to react with a base having pKaH of 11 or higher, to form EDTA. Also provided is a composition comprising a diacid/dinitrile compound (DADN) wherein each R has the structure: ##STR00001##