IE42378B1 - Methjod for the prepartion of n-substituted carbamic acid salts - Google Patents
Methjod for the prepartion of n-substituted carbamic acid saltsInfo
- Publication number
- IE42378B1 IE42378B1 IE2692/75A IE269275A IE42378B1 IE 42378 B1 IE42378 B1 IE 42378B1 IE 2692/75 A IE2692/75 A IE 2692/75A IE 269275 A IE269275 A IE 269275A IE 42378 B1 IE42378 B1 IE 42378B1
- Authority
- IE
- Ireland
- Prior art keywords
- metal
- carbamic acid
- substituted carbamic
- amine
- cycloaliphatic
- Prior art date
Links
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 10
- -1 N-Substituted carbamic acid salts Chemical class 0.000 claims abstract description 9
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical group CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052700 potassium Chemical group 0.000 claims 1
- 239000011591 potassium Chemical group 0.000 claims 1
- 125000006308 propyl amino group Chemical group 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1494769 N-Substituted carbamic acid salts ANIC SpA 8 Dec 1975 [10 Dec 1974] 50300/75 Heading C2C N-Substituted carbamic acid salts of the formula (R-NR1-CO-O-) n M, where M is a metal of Group IA, IIA or IIB of valency n, R is a hydrogen atom or a monovalent aliphatic, aromatic, cycloaliphatic or araliphatic hydrocarbon radical and R1 is a monovalent or divalent aliphatic, aromatic, cycloaliphatic or araliphatic hydrocarbon radical, are obtained by reacting together carbon dioxide, or amines including the radical R-NR1- and compounds having cations of metal M in combination with mono- or di-valent anions.
Description
This invention relates to a method of producing certain carbamic acid salts.
According to the present invention there is provided a method of producing an N-substituted carbamic acid salt of formula in which M represents a metal of Group IA, IIA, or IIB of the periodic table of the elements (as hereinafter defined) having a valency £, R represents a hydrogen, atom or monovalent aliphatic, aromatic, cycloaliphatic or araliphatic hydrocarbon radical and R' represents a mono- or divalent aliphatic, aromatic, cycloaliphatic TO or araliphatic hydrocarbon radical, which method comprises reacting together carbon . dioxide, an amine including the radical in which R and R' are as defined above, and a compound having a cation of metal M in combination with a mono- or divalent anion, to form the desired salt. - 2 42378 The periodic Table referred to above is as published in The Handbook of Chemistry and Physics, 39th Edition, pages 400-401 (Chemical Rubber Publishing Company).
When the radicals R and R' consist of or include an aliphatic hydrocarbon they may be saturated or unsaturated.
The reaction is preferably carried out in an inert liquid which is a solvent for the reactants, for example an aliphatic alcohol such as methanol or ethanol.
The amine used may be, for example, propylamine, diethylamine or N,N!dimethylethylene diamine, whilst preferred anions include carbonates, sulphites, oxides, hydroxides, sulphides, hydrosulphides and chlorides. Particularly preferred compounds are LiCl, LigCOg, CaO, KgCOg anc* KC1.
The reaction may take place by causing a stream of carbon dioxide to bubble through a solution or suspension of the selected metal compound in the o presence of the amine. A C02 pressure of up to 10 kg/cm is preferred.
The temperature of the reaction should be maintained between the freezing point and the boiling point of the inert liquid or the amine, preferably from 0°C to 60°C.
In one embodiment of the invention wherein both the metal M and the anion (X) are monovalent, the reaction scheme proceeds in accordance with the following scheme:MX + CO, + R - N - H —> R - N - COOM + HX 2 I I R' R' In a second embodiment, wherein M is divalent and the anion (X) is monovalent the reaction scheme follows the following path: HX2 + 2C02 + 2R - N - H —> (R - N - COO - )2M + 2HX R1 R‘ In a third embodiment wherein M is monovalent and the anion (X) is divalent, the reaction proceeds as follows: 4237« Μ,Χ + 2C0, + 2R - Ν - Η —2R - Ν - COOM + Η,Χ 2 2 I I 2 R' R' In each of the above embodiments the amine used is a secondary amine.
The reaction products are generally deposited as bulky precipitates. As may be seen from the second reaction scheme above, acidic salts are formed if the metal compound is a salt having a divalent anion.
The amine is preferably used in a stoichiometric excess in order to combine with and neutralise the acidic by-product. Thus, for example, the amine hydrochloride is formed if a metal chloride is used as the starting metal compound.
The separation of the carbamates produced by the method is carried out merely by filtration when the by-products are soluble in the reaction medium; separation may also be achieved by slurrying the crude reaction product in a which solvenly selectively, dissolves the desired carbamate. In this latter case it is possible directly to carry out the reaction in the presence of such a solvent.
The following Examples illustrate the invention.
EXAMPLE 1. 4.25 grams of LiCl were dissolved in 50 mis of methanol in the presence of 12 grams of propylamine. C02 was absorbed into the resulting mixture at room temperature and under a partial pressure of the gas equal to atmospheric pressure. A white precipitate was obtained which was collected on a filter and dried. The yield was 8.0 grams of a product which proved to be Li0C0NHCH2CH2CH3.
EXAMPLE 2. .05 grams of K2C03 were slurried in 50 mis of methanol in the presence of 15 grams of N,N‘ - dimethylethylenediamine. C02 was caused to be absorbed by the resultihg mixture at room temperature with a partial pressure of carbon dioxide of 1 atmosphere.
Almost immediately a white product formed, which was collected on a filter and dried. This product, in a yield of 14.8 grams, was identified as - 4 42378 COOK COOK In addition, after a while, a second product, which was found to be KHCO3, precipitated from the mother liquor.
EXAMPLE 3. 3.5 grams of LiCl were dissolved in 25 mis of ethanol in the presence of 20 grams of diethylamine. This mixture was subjected to C02 absorption at room temperature and with a C02 partial pressure of one atmosphere.
A white product was immediately formed, and this was identified as (CgHg)2NC00Li (9,2 grams). By adding diethylether to the mother liquor a second product was precipitated which was identified as diethyl ammonium chloride /7(c2h5)2nh.hc]7.
Claims (13)
1. A method of producing an N-substituted carbamic acid salt of formula (R - N - C - 0 - ) n M R' 0 in which M represents a metal of Group IA, IIA, or IIB of the periodic table of the elements (as hereinbefore defined) having a valency £, R represents a hydrogen atom or monovalent aliphatic, aromatic, cycloaliphatic or araliphatic hydrocarbon radical and R 1 represents a mono- or divalent aliphatic, aromatic, cycloaliphatic or araliphatic hydrocarbon radical, which method comprises reacting together carbon dioxide, an amine including the radical R - N in which R and R‘ are as defined above, and a compound having a cation of metal M in combination with a mono- or divalent anion, to form the desired salt.
2. A method according to Claim 1 wherein the reaction is effected in the presence of an aliphatic alcohol. - 5
3. or ethanol.
4. A method according to Claim 2 wherein the alcohol is methanol A method according to any one of the preceding claims wherein .2 A method according to Claim 1, 2 or 3 wherein the reaction is carried out at a temperature, of from 0 to 60°C.
5. the carbon dioxide is at a pressure of up to 10 kg/cm' - .
6. A method according to any one of the preceding claims wherein the amine is propylamine or diethylamine.
7. A method according to any one of Claims 1 to 5 wherein the amine is N,N‘-dimethylethylene diamine.
8. A method according to any one of the preceding claims wherein the anion is a carbonate, sulphite, oxide, hydroxide, sulphide, hydrosulphide or chloride.
9. A method according to any one of the preceding claims wherein the metal M is lithium or potassium.
10. A method according to any one of Claims 1 to 8 wherein the metal M is calcium.
11. A method according to any one of the preceding claims which includes the additional step of removing the salt from the product mixture.
12. A method accord!ng to Claim 1 substantially as hereinbefore described in Example 1, 2 or 3.
13. An N-substituted carbamic acid salt whenever produced by the method according to any one of the preceding claims. .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT30340/74A IT1026906B (en) | 1974-12-10 | 1974-12-10 | PROCEDURE FOR THE PREPARATION OF SALTS OF THE SUBSTITUTED CARBAMIC ACID N |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42378L IE42378L (en) | 1976-06-10 |
| IE42378B1 true IE42378B1 (en) | 1980-07-30 |
Family
ID=11229568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2692/75A IE42378B1 (en) | 1974-12-10 | 1975-12-10 | Methjod for the prepartion of n-substituted carbamic acid salts |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS594421B2 (en) |
| AT (1) | AT359083B (en) |
| BE (1) | BE836344A (en) |
| CA (1) | CA1044254A (en) |
| CH (1) | CH624096A5 (en) |
| DE (1) | DE2555630C3 (en) |
| DK (1) | DK557175A (en) |
| ES (1) | ES443590A1 (en) |
| FR (1) | FR2294168A1 (en) |
| GB (1) | GB1494769A (en) |
| IE (1) | IE42378B1 (en) |
| IT (1) | IT1026906B (en) |
| LU (1) | LU73952A1 (en) |
| NL (1) | NL174460C (en) |
| NO (1) | NO149661C (en) |
| SE (1) | SE430602B (en) |
| SU (1) | SU906370A3 (en) |
| ZA (1) | ZA757616B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3673245D1 (en) * | 1985-05-27 | 1990-09-13 | Tosoh Corp | METHOD FOR THE PRODUCTION OF FLUORINE-CONTAINING ALIPHATIC CARBONIC ACIDS. |
| IT1277443B1 (en) * | 1995-08-04 | 1997-11-10 | Enichem Spa | PROCEDURE FOR THE PREPARATION OF SOLUTIONS OF SUBSTITUTED N-ALCYL METALLIC CARBAMATES AND THEIR USE |
| JP7072769B2 (en) | 2018-03-02 | 2022-05-23 | 国立大学法人大阪大学 | Method for Producing Group III Nitride Crystal |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849320A (en) * | 1972-11-30 | 1974-11-19 | Mobil Oil Corp | Organic compositions containing alkali metal arylcarbamates |
-
1974
- 1974-12-10 IT IT30340/74A patent/IT1026906B/en active
-
1975
- 1975-12-04 ZA ZA757616A patent/ZA757616B/en unknown
- 1975-12-05 BE BE162500A patent/BE836344A/en not_active IP Right Cessation
- 1975-12-08 FR FR7537404A patent/FR2294168A1/en active Granted
- 1975-12-08 LU LU73952A patent/LU73952A1/xx unknown
- 1975-12-08 GB GB50300/75A patent/GB1494769A/en not_active Expired
- 1975-12-08 CH CH1594475A patent/CH624096A5/en not_active IP Right Cessation
- 1975-12-09 NO NO754161A patent/NO149661C/en unknown
- 1975-12-09 ES ES443590A patent/ES443590A1/en not_active Expired
- 1975-12-09 CA CA241,391A patent/CA1044254A/en not_active Expired
- 1975-12-09 SE SE7513878A patent/SE430602B/en unknown
- 1975-12-09 NL NLAANVRAGE7514363,A patent/NL174460C/en not_active IP Right Cessation
- 1975-12-09 AT AT933075A patent/AT359083B/en active
- 1975-12-09 DK DK557175A patent/DK557175A/en unknown
- 1975-12-10 JP JP50146469A patent/JPS594421B2/en not_active Expired
- 1975-12-10 SU SU752197059A patent/SU906370A3/en active
- 1975-12-10 IE IE2692/75A patent/IE42378B1/en unknown
- 1975-12-10 DE DE2555630A patent/DE2555630C3/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU906370A3 (en) | 1982-02-15 |
| FR2294168A1 (en) | 1976-07-09 |
| BE836344A (en) | 1976-06-08 |
| LU73952A1 (en) | 1976-07-01 |
| GB1494769A (en) | 1977-12-14 |
| IE42378L (en) | 1976-06-10 |
| SE7513878L (en) | 1976-06-11 |
| CA1044254A (en) | 1978-12-12 |
| JPS5182224A (en) | 1976-07-19 |
| NL174460B (en) | 1984-01-16 |
| IT1026906B (en) | 1978-10-20 |
| CH624096A5 (en) | 1981-07-15 |
| NO754161L (en) | 1976-06-11 |
| NL174460C (en) | 1984-06-18 |
| DE2555630C3 (en) | 1980-03-13 |
| AT359083B (en) | 1980-10-27 |
| ATA933075A (en) | 1980-03-15 |
| NO149661B (en) | 1984-02-20 |
| ES443590A1 (en) | 1977-05-01 |
| DE2555630B2 (en) | 1979-06-28 |
| DK557175A (en) | 1976-06-11 |
| NO149661C (en) | 1984-05-30 |
| FR2294168B1 (en) | 1979-07-20 |
| DE2555630A1 (en) | 1976-06-16 |
| NL7514363A (en) | 1976-06-14 |
| ZA757616B (en) | 1976-11-24 |
| SE430602B (en) | 1983-11-28 |
| JPS594421B2 (en) | 1984-01-30 |
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