US3364248A - Novel dicyanoethylfattydiamines of fatty acids - Google Patents
Novel dicyanoethylfattydiamines of fatty acids Download PDFInfo
- Publication number
- US3364248A US3364248A US398438A US39843864A US3364248A US 3364248 A US3364248 A US 3364248A US 398438 A US398438 A US 398438A US 39843864 A US39843864 A US 39843864A US 3364248 A US3364248 A US 3364248A
- Authority
- US
- United States
- Prior art keywords
- dicyanoethylfattydiamines
- novel
- cyanoethyl
- fatty acids
- fatty
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Definitions
- an object of this invention is to provide novel difunctional fatty compounds which are useful in various chemical technologies.
- Another object is to provide a novel class of fatty diamines, more particularly, dicyanoethylfattydiamines.
- Still another object is to provide novel methods for the manufacture of such dicyanoethylfattydiamines.
- a further object is to provide a novel class of compounds which are excellent intermediates for other tetrafunctional fatty compounds having valuable properties for various chemical technologies.
- the invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the compound possessing the features, properties, and the relation of elements, which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
- a novel class of fatty diamines may be prepared by reacting an aminoalkylfattyamine (described more fully in British 920,514 filed June 30, 1959, and British 985,106 filed Ian. 4, 1962) with acrylonitrile.
- aminoalkylfattyamine described more fully in British 920,514 filed June 30, 1959, and British 985,106 filed Ian. 4, 1962
- acrylonitrile for example, by reacting aminoethylstearylamine with acrylonitrile in the presence of water, N,N-difl-cyanoethyl) aminoethylstearylamine is obtained.
- Such a compound is useful as an intermediate for forming a di- (aminoalkyl) fatty diamine which is useful as a surfactant, particularly as a flotation agent or an asphalt emulsifier, or as an epoxy curing agent. It also is useful as a bactericide.
- Example I.-N,N'-ai-(fi-cyanoethyl) aminostearylamine A two-liter four-neck Morton flask equipped with a mechanical stirrer, thermometer and reflux condenser is charged with 142 gms. (0.5 mole) aminostearylamine and 13 gms. water. The temperature is raised to 70 C. and acryonitrile (59 gms., 1.11 moles) is added with vigorous stirring over a period of one hour. The temperature is maintained at 70 C. during the addition, then raised to C. for an additional two hours. Excess acrylonitrile and water are removed in vacuo to yield 192.4 gms. (98.7% theory) of di-(B-cyanoethyl) aminostearylamine as a light oil.
- Example II.N,N'-di-(fl-cyanoethyl) aminomethylstearylamine A 250 ml. 3-neck flask equipped with a mechanical stirrer, thermometer, dropping funnel and heating mantle is charged with aminomethylstearylamine (50.0 gms., 0.168 mole; NE, 158.5) and water (4.52 ml., 9% by wt. of amine). The temperature of the reactants is raised to 70 C. and acrylonitrile (19.6 gms., 0.37 mole, 10% excess) added slowly with stirring. The addition is complete in about one hour at 70-80" C. The temperature is then maintained at 7685 C. for an additional two hours. Water and excess acrylonitrile are removedin vacuo to yield 66.5 gms. (97.5% yield) of N,N'-di-( 8-cyanoethyl) aminomethylstearylamine as a pale yellow oil.
- the above dicyanoethylfattyamines may be used to prepare polyamines which possess high surfactant activity.
- aminoor aminoalkylfattyamines that may be reacted with acrylonitrile in accordance with the meth 0d of this invention, those falling within the following formula are operable:
- Such compounds would include the amino-, aminomethyl-, and the aminoethyl-derivatives of fatty amines such as caprylylamine, caprylamine, laurylamine, myristylamine, palrnitylamine, stearylamine, arachidylamine, behenylamine and lignocerylamine or mixtures thereof such as derivatives from natural fats and oils such astallow, soybean oil and coconut oil.
- diamine derivatives of the C to C fatty acids are useful as a reactant.
- dicyanoethylfattydiamines that may be formed by the method of this invention are those which fall within the following formula:
- N,N di (18 cyanoethyl) aminomethylcaprylamine N,N-di-(fl-cyanoethyl) aminomethylundecylamine
- N,N'-di- (fl-cyanoethyl) aminomethylstearylamine N,N di 8- cyanoethyl) aminostearylamine, and the like.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent ()filice 3,364,248 Patented Jan. 16, 1968 This invention relates to novel derivatives of fatty acid and more particularly to a novel class of dicyanoethylfattydiamines.
It has long been the desire of chemists to synthesize or to extract from natural substances compounds which not only possess the desirable physical and chemical properties of the long chain fatty acids, but also contain two or more reactive groups therein. With two or more reactive groups, the fatty compound would not only have good hydrophobic characteristics, but also have high potency, depending upon its reactive group type for surfactant, for polymeric or for other chemical activity.
Among the approaches made toward accomplishing such an objective, that disclosed in US. 2,813,113 is typical. There the oxidation of oleic acid to azelaic acid [HOOC(CH COOH] is discussed. Unfortunately, chain cleavage occurs in such oxidation. This is undesirable because it cuts down the hydrophobic nature of the resultant compound.
Rowe and Swern of the US. Department of Agriculture, in the Journal of the American Oil Chemists Society periodical, volume 37, pages 661 to 668 (1960) report that unsaturated fatty acids may be carboxylated with carbon monoxide. Such a reaction would conserve the hydrophobic nature of the fatty acid, but apparently no further work was done toward discovering new difunctional fatty compounds. This is unfortunate because, as discussed below, it has been found that such difunctional compounds may be synthesized rather easily and they possess many attributes highly desirable for various chemical technologies.
Accordingly, an object of this invention is to provide novel difunctional fatty compounds which are useful in various chemical technologies.
Another object is to provide a novel class of fatty diamines, more particularly, dicyanoethylfattydiamines.
Still another object is to provide novel methods for the manufacture of such dicyanoethylfattydiamines.
A further object is to provide a novel class of compounds which are excellent intermediates for other tetrafunctional fatty compounds having valuable properties for various chemical technologies.
Other objects of the invention will in part be obvious and will in part appear hereinafter.
The invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the compound possessing the features, properties, and the relation of elements, which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
It has now been found that a novel class of fatty diamines may be prepared by reacting an aminoalkylfattyamine (described more fully in British 920,514 filed June 30, 1959, and British 985,106 filed Ian. 4, 1962) with acrylonitrile. For example, by reacting aminoethylstearylamine with acrylonitrile in the presence of water, N,N-difl-cyanoethyl) aminoethylstearylamine is obtained. Such a compound is useful as an intermediate for forming a di- (aminoalkyl) fatty diamine which is useful as a surfactant, particularly as a flotation agent or an asphalt emulsifier, or as an epoxy curing agent. It also is useful as a bactericide.
Reference is now made to the following examples which illustrate synthesis of specific dicyanoethylfattydiamines:
Example I.-N,N'-ai-(fi-cyanoethyl) aminostearylamine A two-liter four-neck Morton flask equipped with a mechanical stirrer, thermometer and reflux condenser is charged with 142 gms. (0.5 mole) aminostearylamine and 13 gms. water. The temperature is raised to 70 C. and acryonitrile (59 gms., 1.11 moles) is added with vigorous stirring over a period of one hour. The temperature is maintained at 70 C. during the addition, then raised to C. for an additional two hours. Excess acrylonitrile and water are removed in vacuo to yield 192.4 gms. (98.7% theory) of di-(B-cyanoethyl) aminostearylamine as a light oil.
Analysis.-Neut. equivalent, 198.6 (calcd. primary amine, 3.3%; secondary amine, 93.6%; tertiary amine, nil.
Example II.N,N'-di-(fl-cyanoethyl) aminomethylstearylamine A 250 ml. 3-neck flask equipped with a mechanical stirrer, thermometer, dropping funnel and heating mantle is charged with aminomethylstearylamine (50.0 gms., 0.168 mole; NE, 158.5) and water (4.52 ml., 9% by wt. of amine). The temperature of the reactants is raised to 70 C. and acrylonitrile (19.6 gms., 0.37 mole, 10% excess) added slowly with stirring. The addition is complete in about one hour at 70-80" C. The temperature is then maintained at 7685 C. for an additional two hours. Water and excess acrylonitrile are removedin vacuo to yield 66.5 gms. (97.5% yield) of N,N'-di-( 8-cyanoethyl) aminomethylstearylamine as a pale yellow oil.
Analysis.-Neut. equiv, 212 (calc d 202.3); secondary amine 92.2%.
The above dicyanoethylfattyamines may be used to prepare polyamines which possess high surfactant activity.
Among the aminoor aminoalkylfattyamines that may be reacted with acrylonitrile in accordance with the meth 0d of this invention, those falling within the following formula are operable:
FORMULA I CHa(CH,)xCH(CHz)yNH,
where 11:0 to 2, x and y are whole numbers and x+y=6 to 22.
Such compounds would include the amino-, aminomethyl-, and the aminoethyl-derivatives of fatty amines such as caprylylamine, caprylamine, laurylamine, myristylamine, palrnitylamine, stearylamine, arachidylamine, behenylamine and lignocerylamine or mixtures thereof such as derivatives from natural fats and oils such astallow, soybean oil and coconut oil. In general, diamine derivatives of the C to C fatty acids are useful as a reactant.
The dicyanoethylfattydiamines that may be formed by the method of this invention are those which fall within the following formula:
FORMULA II CHz-(CHz) -CH-(CHg) FNHGHRCHKCN (CHzhNHCHaCHzCN where a=0 to 2, x and y are whole numbers and x+y=6 to 22.
Among compounds which fall within the above formula are N,N di (18 cyanoethyl) aminomethylcaprylamine, N,N-di-(fl-cyanoethyl) aminomethylundecylamine, N,N'- di- (3 cyanoethyl)aminomethylpalymitylamine, N,N'-di- (fl-cyanoethyl) aminomethylstearylamine, N,N di 8- cyanoethyl) aminostearylamine, and the like.
It will thus be seen that the objects set forth above, among those made apparent from the preceding description, are efficiently attained and, since certain changes may be made in carrying out the above method and in the compounds set forth Without departing from the scope of the invention, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.
It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention, which, as a matter of language, might be said to fall therebetween.
Now that the invention has been described, what is claimed as new and desired to be secured by Letters Patent is:
What is claimed is:
l. A dicyanoethylfattydiarnine of the formula:
where (1:0 to 2, x and y are whole numbers and x+y=6 to 22. 2. N,N'-di-(5-eyanoethyl) aminomethylpalmitylarnine falling within the formula:
CHE-(CH2)xCH(CHz)yNHCHzCHzCN CHNHCH2CH;CN
where x+y=16, said x and y being whole numbers.
3. N,N'-di B cyanoethyl) aminomethylstearylamine falling Within the formula:
C H3- CII2 x C H(C 11:) NECHzC H2CN where x+y:16, said x and y being whole numbers.
4. N,N' di (ti-cyanoethyl) aminostearylarnine falling within the formula:
NHCHzCHzCN Where x+y 16, said x and y being whole numbers.
References Cited UNITED JOSEPH P. BRUST, Primary Examiner.
Claims (1)
1. A DICYANOETHYLFATTYDIAMINE OF THE FORMULA:
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US398438A US3364248A (en) | 1964-09-22 | 1964-09-22 | Novel dicyanoethylfattydiamines of fatty acids |
DE19651493436 DE1493436A1 (en) | 1964-09-22 | 1965-09-17 | Process for the production of dicyanoethyl fatty acid diamines |
FR32107A FR1447614A (en) | 1964-09-22 | 1965-09-21 | New fatty acid derivatives and process for their preparation |
GB40434/65A GB1045505A (en) | 1964-09-22 | 1965-09-22 | Dicyanoethyl fatty diamines |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US398438A US3364248A (en) | 1964-09-22 | 1964-09-22 | Novel dicyanoethylfattydiamines of fatty acids |
Publications (1)
Publication Number | Publication Date |
---|---|
US3364248A true US3364248A (en) | 1968-01-16 |
Family
ID=23575375
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US398438A Expired - Lifetime US3364248A (en) | 1964-09-22 | 1964-09-22 | Novel dicyanoethylfattydiamines of fatty acids |
Country Status (3)
Country | Link |
---|---|
US (1) | US3364248A (en) |
DE (1) | DE1493436A1 (en) |
GB (1) | GB1045505A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3666788A (en) * | 1969-08-22 | 1972-05-30 | Jefferson Chem Co Inc | Cyanoalkylated polyoxyalkylene polyamines |
US4180487A (en) * | 1978-05-04 | 1979-12-25 | Henkel Corporation | Epoxy curable resin composition |
US4257984A (en) * | 1977-04-04 | 1981-03-24 | Henkel Corporation | Monotertiarymonosecondarydiprimarytetramine and monotertiarymonosecondarydinitrilodiamines |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4271088A (en) | 1978-06-16 | 1981-06-02 | Suntech, Inc. | High selectivity cyanoalkylation process |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1992615A (en) * | 1931-09-10 | 1935-02-26 | Ig Farbenindustrie Ag | Amino nitrile and process of producing same |
US2448013A (en) * | 1944-12-26 | 1948-08-31 | Upjohn Co | Preparation of beta-aminopropionitrile |
US2965671A (en) * | 1957-04-22 | 1960-12-20 | Monsanto Chemicals | Process for production of amino compounds |
US2982782A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and beta-aminoesters |
US2982781A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and- beta-aminoesters |
US3158643A (en) * | 1961-05-05 | 1964-11-24 | Gen Mills Inc | Cyanoethylated aminohydroxy amines |
US3177254A (en) * | 1961-05-23 | 1965-04-06 | Gen Mills Inc | Aminohydroxy amines |
US3264341A (en) * | 1961-07-03 | 1966-08-02 | Armour & Co | Preparation of dicyanoethylated fatty amines |
-
1964
- 1964-09-22 US US398438A patent/US3364248A/en not_active Expired - Lifetime
-
1965
- 1965-09-17 DE DE19651493436 patent/DE1493436A1/en active Pending
- 1965-09-22 GB GB40434/65A patent/GB1045505A/en not_active Expired
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1992615A (en) * | 1931-09-10 | 1935-02-26 | Ig Farbenindustrie Ag | Amino nitrile and process of producing same |
US2448013A (en) * | 1944-12-26 | 1948-08-31 | Upjohn Co | Preparation of beta-aminopropionitrile |
US2965671A (en) * | 1957-04-22 | 1960-12-20 | Monsanto Chemicals | Process for production of amino compounds |
US2982782A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and beta-aminoesters |
US2982781A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and- beta-aminoesters |
US3158643A (en) * | 1961-05-05 | 1964-11-24 | Gen Mills Inc | Cyanoethylated aminohydroxy amines |
US3177254A (en) * | 1961-05-23 | 1965-04-06 | Gen Mills Inc | Aminohydroxy amines |
US3264341A (en) * | 1961-07-03 | 1966-08-02 | Armour & Co | Preparation of dicyanoethylated fatty amines |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3666788A (en) * | 1969-08-22 | 1972-05-30 | Jefferson Chem Co Inc | Cyanoalkylated polyoxyalkylene polyamines |
US4257984A (en) * | 1977-04-04 | 1981-03-24 | Henkel Corporation | Monotertiarymonosecondarydiprimarytetramine and monotertiarymonosecondarydinitrilodiamines |
US4180487A (en) * | 1978-05-04 | 1979-12-25 | Henkel Corporation | Epoxy curable resin composition |
Also Published As
Publication number | Publication date |
---|---|
DE1493436A1 (en) | 1972-02-24 |
GB1045505A (en) | 1966-10-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0049463B1 (en) | Preparation of linear polyalkylene polyamines | |
CN1227321C (en) | Cationic gamini and related multiple hydrophilic/hydrophobic functional compounds and their use as surfactants | |
US3398197A (en) | Nu-secondary-alkyl tertiary amine compounds | |
US4967008A (en) | Polyamines and their preparation | |
US4503253A (en) | Production of noncyclic polyalkyene polyamines | |
FR2419261A1 (en) | PROCESS FOR THE PRODUCTION OF CEMENT-BASED HARDENING BINDERS | |
US3364248A (en) | Novel dicyanoethylfattydiamines of fatty acids | |
US2502478A (en) | Tetrafluorosuccinic acid derivatives and their preparation | |
US3418374A (en) | Fatty polyamines and their alkyl and alkoxy derivatives | |
US2096749A (en) | Derivatives of alkylolamine condensation products | |
US4982000A (en) | Process for preparing quaternary ammonium compounds | |
US2708666A (en) | Cationic surface active agents | |
US3510521A (en) | Branched fatty tetraamines and alkyl and alkoxy derivatives thereof | |
US4517122A (en) | Cyclic peptides | |
EP1786763B1 (en) | N, n', n"-tris-(3-dimethylaminopropyl)-guanidine, the procedure of preparation from carbodiimide and application in reactions of transesterification of oil | |
US2334517A (en) | High molecular weight surface active amines | |
US3488389A (en) | Perfluoroimides | |
Jordan Jr et al. | Low temperature aminolysis of methyl stearate catalyzed by sodium methoxide | |
US3354213A (en) | Derivatives of fatty acids | |
US4110358A (en) | Ampholytic quaternary ammonium compounds and methods for their preparation | |
US3064047A (en) | N, n', n"-trisubstituted oxyaspartamides | |
US2983738A (en) | Polyoxyalkylated aliphatic nitriles and amines and method | |
US2750366A (en) | Mono-acyl derivatives of alkylene diamines and process for preparing same | |
DD275046A1 (en) | PROCESS FOR PREPARING NEW PYRROLIDINIUM SULFOBETAINES WITH CARBONAMIDE GROUPS | |
JPS6256472A (en) | Quaternary ammonium salt compound |