CA1069122A - Preparation of dialkali metal hexahydropyrimidine-1, 3-diacetate and dialkalimetal 5-hydroxyhexahydropyrimidine-1, 3-diacetate - Google Patents
Preparation of dialkali metal hexahydropyrimidine-1, 3-diacetate and dialkalimetal 5-hydroxyhexahydropyrimidine-1, 3-diacetateInfo
- Publication number
- CA1069122A CA1069122A CA262,163A CA262163A CA1069122A CA 1069122 A CA1069122 A CA 1069122A CA 262163 A CA262163 A CA 262163A CA 1069122 A CA1069122 A CA 1069122A
- Authority
- CA
- Canada
- Prior art keywords
- alkali metal
- diacetate
- cyanide
- reaction zone
- hcn
- 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
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 32
- 239000002184 metal Substances 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title abstract description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 118
- 239000007864 aqueous solution Substances 0.000 claims abstract description 40
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 39
- -1 alkali metal cyanide Chemical class 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 235000019256 formaldehyde Nutrition 0.000 claims abstract description 31
- 229960004279 formaldehyde Drugs 0.000 claims abstract description 29
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims abstract description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 18
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 15
- ROYZEMODCVMWJX-UHFFFAOYSA-N 1,3-diazinan-5-ol Chemical compound OC1CNCNC1 ROYZEMODCVMWJX-UHFFFAOYSA-N 0.000 claims abstract description 12
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000006227 byproduct Substances 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- 230000008016 vaporization Effects 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 78
- 238000006243 chemical reaction Methods 0.000 claims description 61
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000008098 formaldehyde solution Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical group N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 5
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007429 general method Methods 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 1
- RKPHYUBLENEQNT-UHFFFAOYSA-N 2-[3-(carboxymethylamino)propylamino]acetic acid Chemical compound OC(=O)CNCCCNCC(O)=O RKPHYUBLENEQNT-UHFFFAOYSA-N 0.000 description 1
- ORPMKYQHXVPRAA-UHFFFAOYSA-N 2-[[3-(carboxymethylamino)-2-hydroxypropyl]amino]acetic acid Chemical compound OC(=O)CNCC(O)CNCC(O)=O ORPMKYQHXVPRAA-UHFFFAOYSA-N 0.000 description 1
- ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/04—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/630,791 US3988367A (en) | 1975-11-11 | 1975-11-11 | Preparation of N,N'-dicarboxymethyl-1,3-propanediamines |
| US71157476A | 1976-08-04 | 1976-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069122A true CA1069122A (en) | 1980-01-01 |
Family
ID=27091227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA262,163A Expired CA1069122A (en) | 1975-11-11 | 1976-09-28 | Preparation of dialkali metal hexahydropyrimidine-1, 3-diacetate and dialkalimetal 5-hydroxyhexahydropyrimidine-1, 3-diacetate |
Country Status (7)
| Country | Link |
|---|---|
| CA (1) | CA1069122A (enrdf_load_stackoverflow) |
| DE (3) | DE2648354A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2338265A1 (enrdf_load_stackoverflow) |
| GB (4) | GB1521927A (enrdf_load_stackoverflow) |
| GR (1) | GR61733B (enrdf_load_stackoverflow) |
| IL (1) | IL50755A (enrdf_load_stackoverflow) |
| IT (1) | IT1077086B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166341A (en) * | 1988-07-29 | 1992-11-24 | Dainippon Pharmaceutical Co., Ltd. | 6-amino-1,4-hexahydro-1H-diazepine derivatives |
| NZ230068A (en) * | 1988-07-29 | 1991-07-26 | Dainippon Pharmaceutical Co | Indazole-3-carboxylic acid esters and amides of diaza compounds having 6,7, or 8 ring members: preparatory processes and pharmaceutical compositions |
-
1976
- 1976-09-28 CA CA262,163A patent/CA1069122A/en not_active Expired
- 1976-10-05 IL IL50755A patent/IL50755A/xx unknown
- 1976-10-25 GB GB27012/77A patent/GB1521927A/en not_active Expired
- 1976-10-25 GB GB27014/77A patent/GB1521929A/en not_active Expired
- 1976-10-25 GB GB44253/76A patent/GB1521925A/en not_active Expired
- 1976-10-25 GR GR52013A patent/GR61733B/el unknown
- 1976-10-25 FR FR7632108A patent/FR2338265A1/fr active Granted
- 1976-10-25 GB GB27013/77A patent/GB1521928A/en not_active Expired
- 1976-10-25 IT IT28656/76A patent/IT1077086B/it active
- 1976-10-26 DE DE19762648354 patent/DE2648354A1/de active Granted
- 1976-10-26 DE DE2661113A patent/DE2661113C2/de not_active Expired - Lifetime
- 1976-10-26 DE DE2661114A patent/DE2661114C2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2338265A1 (fr) | 1977-08-12 |
| GB1521928A (en) | 1978-08-16 |
| GB1521929A (en) | 1978-08-16 |
| IL50755A (en) | 1980-11-30 |
| GB1521925A (en) | 1978-08-16 |
| DE2648354C2 (enrdf_load_stackoverflow) | 1992-04-09 |
| IT1077086B (it) | 1985-04-27 |
| DE2661113C2 (enrdf_load_stackoverflow) | 1991-08-29 |
| DE2661114C2 (enrdf_load_stackoverflow) | 1992-04-09 |
| DE2648354A1 (de) | 1977-05-18 |
| IL50755A0 (en) | 1976-12-31 |
| GB1521927A (en) | 1978-08-16 |
| GR61733B (en) | 1978-12-30 |
| FR2338265B1 (enrdf_load_stackoverflow) | 1981-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |