MXPA97007345A - Process for ami - Google Patents
Process for amiInfo
- Publication number
- MXPA97007345A MXPA97007345A MXPA/A/1997/007345A MX9707345A MXPA97007345A MX PA97007345 A MXPA97007345 A MX PA97007345A MX 9707345 A MX9707345 A MX 9707345A MX PA97007345 A MXPA97007345 A MX PA97007345A
- Authority
- MX
- Mexico
- Prior art keywords
- process according
- separately
- hydrogen atom
- surfactant
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 239000004094 surface-active agent Substances 0.000 claims abstract description 18
- -1 alkynyl alcohol Chemical compound 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 125000004965 chloroalkyl group Chemical group 0.000 claims abstract description 3
- 238000003786 synthesis reaction Methods 0.000 claims abstract 3
- 230000002194 synthesizing Effects 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000005576 amination reaction Methods 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 239000002280 amphoteric surfactant Substances 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WTNNDYSRQSOJKB-UHFFFAOYSA-N 3-chloro-3-methylpent-1-yne Chemical compound CCC(C)(Cl)C#C WTNNDYSRQSOJKB-UHFFFAOYSA-N 0.000 description 4
- YGWRQPVJLXLHAC-UHFFFAOYSA-N 3-methylpent-1-yn-3-amine Chemical compound CCC(C)(N)C#C YGWRQPVJLXLHAC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- QXLPXWSKPNOQLE-UHFFFAOYSA-N Methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M Copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N Methyl isopropyl ketone Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- FPKOPBFLPLFWAD-UHFFFAOYSA-N Trinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O FPKOPBFLPLFWAD-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- HZNQVAOLVRFZBE-UHFFFAOYSA-N ethenylcyclohexane Chemical group C=C[C]1CCCCC1 HZNQVAOLVRFZBE-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Abstract
The present invention relates to a process for the synthesis of an aminoalkino, which comprises the following steps: a. reacting an alkynyl alcohol with HC1 to form a chloroalkyl, b. reacting said chloroalkyne with a water-soluble aminating agent in the presence of a surfactant to form an aminoalkino and, optionally, c. purify said aminoalkyne by distillation
Description
Process for Amines
This invention relates to an improved process for the preparation of amines, which are useful in the subsequent formation of biologically active materials.
The process of this invention comprises a two-step sequence wherein an alcohol is converted to an organic chloride through the reaction with a chlorinating agent in a first step, followed by amination of the organic chloride in the corresponding amine in a second stage. . In the second step, a surfactant is employed to facilitate the reaction. The presence of the surfactant is especially valuable when the organic chloride that is formed in the first stage is insoluble in water but the aminating agent is soluble in water. Although in theory it is not desired to bind, it is believed that the surfactant increases the surface area of the organic chloride in the aqueous medium. This results in a large contact area for the reaction with the aminating agent, and consequently improves the mass transfer ability; thus, the reaction time is reduced. Additionally, the selectivity and production of the desired amine material are increased due to the reduced formation of unwanted byproducts;
this results in an economically viable process and the ability to market the subsequent pesticide product in a more economical way. The process of this invention, with the use of a surfactant, is most useful for the preparation of aminoalkynes from the corresponding chloroalkyne and its precursor alkynyl alcohol, wherein the chloroalkyne is insoluble in water and the amination agent, such as Ammonia or methylamine, is soluble in water. Processes for the chlorination of chloroalkines have been described in Michelotti et al. in US 5,254,584 as in Hennion et al. in J. Am. Chem. Soc., 75, 1653 (1953); however, the use of a surfactant agent in such processes was not disclosed or suggested. Another method for preparing an aminoalkyne by reaction of chloroalkine with sodium amide in liquid ammonia in J: Org. Chem., 45, 4616
(1980); however, these processes are only feasible on a laboratory scale and are not suitable as a large-scale commercial process. The process of the present invention comprises the following steps: a. reacting an alkynyl alcohol with HCl to form a chloroalkyl, b. reacting said chloroalkyne with a water-soluble aminating agent in the presence of a surfactant to form an aminoalkino and, optionally, c. purify said aminoalkyne by distillation. More specifically, the process of this invention comprises the following steps: a. reacting an alkynyl alcohol of the formula
with a saturated aqueous solution of HCl to form a chloroalkyne of the formula
b. reacting said chloroalkyne with a water soluble amination agent of the formula NR3R4 in the presence of a nonionic, cationic or amphoteric surfactant to form an aminoalkyne of the formula
and, optionally, c. purifying said aminoalkino by distillation; wherein R is a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl or aralkyl;
R1 and R2 are each, separately, alkyl, cycloalkyl, cycloalkylalkyl, aralkyl or, together with the carbon atom to which they are added, form a cycloalkyl; and R3 and R4 are each, separately, a hydrogen atom or a lower alkyl. In this invention, the alkyl is straight or branched chain (C? -C8) alkyl and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n -amyl, isoamyl, n-hexyl and n-octyl. The lower alkyl is straight or branched chain (C 1 -C 4) alkyl. Cycloalkyl includes, for example, cyclopentyl and cyclohexyl. Cycloalkylalkyl includes, for example, cyclopentyl and cyclohexyl. Cycloalkylalkyl includes, for example, cyclopentylmethyl, cyclohexylethyl, 3-cyclopentylpropyl, 4-cyclohexylbutyl and the like. For aralkyl, the aryl portion of the moiety is defined as phenyl or phenyl substituted with one or two substituents independently selected from halo and alkyl; the alkyl part of the half is defined as straight chain (C 1 -C 4) alkyl. Examples of aralkyl include benzyl, phenethyl, 4-chlorobenzyl, 4-methylbenzyl and 2-chlorophenethyl. In a preferred embodiment of this invention, R is a hydrogen atom or lower alkyl, R1 and R2 are, separately, lower alkyl or, together with the carbon atom to which they are added, form a cyclopentyl or cyclohexyl, R3 and R4 they are, separately, a hydrogen atom or lower alkyl, and the surfactant is non-ionic. In a more preferred embodiment of the present invention, R is a hydrogen atom, R1 and R2 are, separately, methyl or ethyl, R3 and R4 are hydrogen atoms, and the surfactant is an alkylphenoxy-polyethoxy-ethanol. In an even more preferred embodiment of this invention, R1 is methyl and R2 is methyl or ethyl. The reaction sequence for steps 1 and 2 is carried out more conveniently at ambient pressure and at a temperature of about 10 ° C to about -10 ° C. However, if desired, the sequence can be brought under a higher pressure at atmospheric pressure and at higher temperatures. Stoichiometry is relatively unimportant, but it is generally more convenient to employ a stoichiometric excess of HCl in the first stage, and a stoichiometric excess of the amination agent in the second stage. In the first stage, a chlorination catalyst such as copper chloride (I) can be used. Generally, a depression of hydrogen chloride, for example, a strong base such as potassium or sodium hydroxide, is used in the second stage to reduce the consumption of the amination reagent; however, if desired, an excess of amination reagent such as HCl depression may also be employed. The reaction times for both stages can vary, and usually depend on the cooling capacity and the mixing characteristics of the reaction vessel; the conversion of the starting material to the desired product or intermediate is conveniently followed by the use of liquid gas chromatography (CLG) or high performance liquid chromatography (CLAD). The amount of the surfactant used in step 2 can be varied, but is generally within the range of 0.01 to 10% by weight, based on the amount of organic chloride present. Preferably, the amount of the surfactant will be within the range of 0.1 to 1.0% by weight, based on the amount of organic chloride present. The following examples are to better illustrate the present invention and not to limit its scope, which is defined by the claims.
Example 1; Formation of 3-chloro-3-methyl-1-pentyne In a reactor, consisting of a one-liter resin vessel, equipped with a thermometer, a gas dispersion tube, a general agitation motor with a stirring blade of recoil, a circulating bath of Lauda type, a caustic scrubber and an addition funnel to compensate the pressure with an attachment for a slow nitrogen sweep, 300 ml were added. (3.6 mol) of concentrated hydrochloric acid together with 1.58 gr. (16 mmol) of copper (I) chloride. The cooling bath was set at 0 ° C, and the hydrogen chloride gas was introduced. The HCl solution was exothermic; As the solution approached saturation, the temperature of the bath was lowered until a container temperature of ~ -5 ° C was reached. 3-Methyl-1-pentin-3-ol (250 gr. , 2.5 mol) was charged in the addition funnel. A slow nitrogen sweep was started so that the HCl vapor would reach the alcohol through the lateral arm. The alcohol was added dropwise at an index such that the reaction temperature remained at 0 ° C or less for 2 to 3 hours. The addition of hydrogen chloride gas was continued during feeding to maintain saturation. At the end of the feed, the addition of hydrogen chloride was stopped and the dispersion tube was raised above the liquid level. The reaction mixture was allowed to stir for 30 minutes at 0 ° C, then the stirring was stopped and the layers were allowed to separate. The inner aqueous layer was removed and the organic phase was washed with water and then with a mixture of saturated brine and sodium bicarbonate solution. The organic phase was stored in a refrigerator until used in the next stage. The procedure provided approximately 280 to 290 gr. from a yellow liquid to coffee, whose purity estimated by CLG was found to be between 90 to 96%.
Example 2: Formation of 3-amino-3-methyl-1-pentyne. In a reactor, consisting of a one-liter resin container, a Lauda-type refrigerated bath, a gas dispersion tube, two addition funnels to compensate the pressure, a thermometer, a nitrogen sweep and a gas inlet and outlet. equipped with the appropriate siphons, 350 ml were added. (2.6 mol) of concentrated ammonium hydroxide solution and 1.00 gr. of Triton® X-100 (trademark of Union Carbide Chemical &Plastics Co.). The cooling bath was set at approximately 0 ° C, and the ammonia gas was introduced. The ammonia solution was a bit exothermic. As the solution approached saturation, the bath temperature was lowered until a container temperature of ~ -5 ° C was reached. One of the addition funnels was charged with 250 g. (2.0 mol) of 3-chloro-3-methyl-1-pentyne, and the other was loaded with 172 g. (2.2 mol) of 50% sodium hydroxide. A slow nitrogen sweep was placed in the addition funnel containing chloride to prevent ammonia vapors from entering the funnel through the lateral arm. The chloride and the caustic were added simultaneously by dropping at an index such that the reaction temperature remained at 0 ° C or less for 3 to 4 hours. The addition of ammonia was continued during feeding to maintain saturation. At the end of the feed, the ammonia addition was stopped and the dispersion tube was raised above the liquid level. The reaction mixture was allowed to stir at 0 ° C until it was found that the level of unreacted chloride was less than 1% by CLG. Stirring was stopped and the layers were allowed to separate. The lower aqueous layer was removed and discarded, and the upper organic layer transferred to a distillation flask together with 75 ml. of water. Then the mixture was distilled using a 15 cm Vigreuex covered column. The fraction boiling from 85 to 92 ° C was collected to provide 174.3 gr. of a white water liquid. The largest fraction was distilled as an azeotrope with water. It was found that the material contained ~ -28% water. Of the remaining organic material, the CLG analysis indicated 90% of 3-amino-3-methyl-1-pentyne with most of the remainder being 3-methyl-1-pentin-3-ol and butanone. The production of 3-amino-3-methyl-1-pentyne was 60%, based on the starting material of 3-chloro-3-methyl-1-pentyne.
Comparative Example: Formation of 3-amino-3-methyl-1-pentin.
The procedure used was substantially similar to that employed in Example 2, except that no surfactant was added to the reactor system. The production of 3-amino-3-methyl-1-pentyne in this case was 39%, based on the starting material of 3-chloro-3-methyl-1-pentyne. It should be understood that the foregoing description is indicated by way of illustration and not limitation, and that various changes and modifications may be made to it without departing from the spirit and scope of the present invention, as defined by the following claims.
Claims (22)
1. A process for the synthesis of an aminoalkyne, comprising the following steps: a. reacting an alkynyl alcohol with HCl to form a chloroalkyl, b. reacting said chloroalkyne with a water-soluble aminating agent in the presence of a surfactant to form an aminoalkyne and, optionally, c.purifying said aminoalkyne by distillation.
2. The process according to claim 1, which comprises the following steps: a. reacting an alkynyl alcohol of the formula OH with a saturated aqueous solution of HCl to form a chloroalkyne of the formula Cl b. reacting said chloroalkyne with a water soluble amination agent of the formula NR3R4 in the presence of a nonionic, cationic or amphoteric surfactant to form an aminoalkyne of the formula and, optionally, c. purifying said aminoalkino by distillation; wherein R is a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl or aralkyl; R1 and R2 are each, separately, alkyl, cycloalkyl, cycloalkylalkyl, aralkyl or, together with the carbon atom to which they are added, form a cycloalkyl; and R3 and R4 are each, separately, a hydrogen atom or a lower alkyl.
3. The process according to claim 2, wherein R is a hydrogen atom or lower alkyl.
4. The process according to claim 2, wherein R1 and R2 are, separately, lower alkyl or, together with the carbon atom to which they are added, form a cyclopentyl or cyclohexyl.
5. The process according to claim 2, wherein R3 and R4 are, separately, a hydrogen atom or lower alkyl.
6. The process according to claim 2, wherein the surfactant is non-ionic.
7. The process according to claim 3, wherein R is a hydrogen atom.
8. The process according to claim 4, wherein R1 and R2 are, separately, methyl or ethyl.
9. The process according to claim 5, wherein R3 and R4 are hydrogen atoms.
10. The process according to claim 8, wherein R1 is methyl and R2 is methyl or ethyl.
11. A process for the synthesis of an aminoalkyne from a chloroalkyne, which comprises reacting said chloroalkyne with a water-soluble amination agent in the presence of a surfactant.
12. The process according to claim 11, wherein the chloroalkyne having the formula is reacted with a water-soluble amination agent of the formula NR3R4 in the presence of a non-ionic, cationic or amphoteric surfactant to form an aminoalkyne of the formula wherein R is a hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl or aralkyl; R1 and R2 are each, separately, alkyl, cycloalkyl, cycloalkylalkyl, aralkyl or, together with the carbon atom to which they are added, form a cycloalkyl; and R3 and R4 are each, separately, a hydrogen atom or a lower alkyl.
13. The process according to claim 12, wherein R is a hydrogen atom or lower alkyl.
14. The process according to claim 12, wherein R1 and R2 are, separately, lower alkyl or, together with the carbon atom to which they are added, form a cyclopentyl or cyclohexyl.
15. The process according to claim 12, wherein R3 and R4 are, separately, a hydrogen atom or lower alkyl.
16. The process according to claim 12, wherein the surfactant is non-ionic.
17. The process according to claim 13, wherein R is a hydrogen atom.
18. The process according to claim 14, wherein R1 and R2 are, separately, methyl or ethyl.
19. The process according to claim 15, wherein R3 and R4 are hydrogen atoms.
20. The process according to claim 18, wherein R 1 is methyl and R 2 is methyl or ethyl.
21. The process according to claim 6, wherein the surfactant is an alkylphenoxy-polyethoxy-ethanol.
22. The process according to claim 16, wherein the surfactant is an alkylphenoxy-polyethoxy-ethanol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2686496P | 1996-10-01 | 1996-10-01 | |
| US026864 | 1996-10-01 | ||
| US026,864 | 1996-10-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MXPA97007345A true MXPA97007345A (en) | 1998-04-01 |
| MX9707345A MX9707345A (en) | 1998-04-30 |
Family
ID=21834227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX9707345A MX9707345A (en) | 1996-10-01 | 1997-09-25 | Process for amines. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0834498B1 (en) |
| JP (1) | JPH10114727A (en) |
| KR (1) | KR19980032426A (en) |
| CN (1) | CN1124253C (en) |
| AT (1) | ATE193520T1 (en) |
| AU (1) | AU3759697A (en) |
| BR (1) | BR9704945A (en) |
| CA (1) | CA2215813A1 (en) |
| DE (1) | DE69702171T2 (en) |
| HU (1) | HUP9701594A3 (en) |
| IL (1) | IL121799A (en) |
| MX (1) | MX9707345A (en) |
| TR (1) | TR199701087A2 (en) |
| ZA (1) | ZA978492B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0312863D0 (en) | 2003-06-04 | 2003-07-09 | Syngenta Ltd | Fungicides |
| CN102180798B (en) * | 2011-03-18 | 2013-11-06 | 湖北汉星化工新材料有限公司 | Method for catalyzing and synthesizing N,N-diethyl propargylamine by using one-step method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1927528C3 (en) * | 1969-05-30 | 1978-01-19 | Basf Ag | PROCESS FOR THE PRODUCTION OF ALPHAETHINYLAMINES |
| HU187775B (en) * | 1982-07-14 | 1986-02-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | New process for producing propargile-amines of pharmaceutical activity |
| US5254584A (en) * | 1992-12-18 | 1993-10-19 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
-
1997
- 1997-09-17 AU AU37596/97A patent/AU3759697A/en not_active Abandoned
- 1997-09-18 IL IL12179997A patent/IL121799A/en not_active IP Right Cessation
- 1997-09-18 CA CA002215813A patent/CA2215813A1/en not_active Abandoned
- 1997-09-22 ZA ZA9708492A patent/ZA978492B/en unknown
- 1997-09-25 MX MX9707345A patent/MX9707345A/en not_active Application Discontinuation
- 1997-09-26 CN CN97116937A patent/CN1124253C/en not_active Expired - Lifetime
- 1997-09-29 JP JP9279317A patent/JPH10114727A/en not_active Withdrawn
- 1997-09-29 KR KR1019970049657A patent/KR19980032426A/en not_active Application Discontinuation
- 1997-09-30 DE DE69702171T patent/DE69702171T2/en not_active Expired - Lifetime
- 1997-09-30 EP EP97307688A patent/EP0834498B1/en not_active Expired - Lifetime
- 1997-09-30 BR BR9704945A patent/BR9704945A/en not_active Application Discontinuation
- 1997-09-30 HU HU9701594A patent/HUP9701594A3/en unknown
- 1997-09-30 AT AT97307688T patent/ATE193520T1/en not_active IP Right Cessation
- 1997-10-01 TR TR97/01087A patent/TR199701087A2/en unknown
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