IE43027B1 - Process for preparing iminodiacetonitrile - Google Patents
Process for preparing iminodiacetonitrileInfo
- Publication number
- IE43027B1 IE43027B1 IE692/76A IE69276A IE43027B1 IE 43027 B1 IE43027 B1 IE 43027B1 IE 692/76 A IE692/76 A IE 692/76A IE 69276 A IE69276 A IE 69276A IE 43027 B1 IE43027 B1 IE 43027B1
- Authority
- IE
- Ireland
- Prior art keywords
- hcn
- hmta
- solution
- acid
- strong acid
- Prior art date
Links
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 87
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 40
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 39
- 229960004011 methenamine Drugs 0.000 claims abstract description 39
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 33
- 239000000243 solution Substances 0.000 claims abstract description 28
- 239000007864 aqueous solution Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 238000010923 batch production Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 32
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000011369 resultant mixture Substances 0.000 claims description 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical group OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 abstract description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract description 4
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000463 material Substances 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- LJAIDEYQVIJERM-UHFFFAOYSA-N 2-[bis(cyanomethyl)amino]acetonitrile Chemical compound N#CCN(CC#N)CC#N LJAIDEYQVIJERM-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- HAXVIVNBOQIMTE-UHFFFAOYSA-L disodium;2-(carboxylatomethylamino)acetate Chemical group [Na+].[Na+].[O-]C(=O)CNCC([O-])=O HAXVIVNBOQIMTE-UHFFFAOYSA-L 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- -1 alkali metal salt Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 150000008361 aminoacetonitriles Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56514875A | 1975-04-04 | 1975-04-04 | |
| US05/652,497 US3993681A (en) | 1975-04-04 | 1976-01-26 | Process for preparing iminodiacetonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE43027B1 true IE43027B1 (en) | 1980-12-03 |
Family
ID=27073776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE692/76A IE43027B1 (en) | 1975-04-04 | 1976-04-02 | Process for preparing iminodiacetonitrile |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3993681A (enExample) |
| JP (1) | JPS51138618A (enExample) |
| DE (1) | DE2613994A1 (enExample) |
| FR (1) | FR2306198A1 (enExample) |
| GB (1) | GB1525645A (enExample) |
| IE (1) | IE43027B1 (enExample) |
| IT (1) | IT1059267B (enExample) |
| NL (1) | NL7603451A (enExample) |
| SE (1) | SE7603952L (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156096A (en) * | 1978-03-15 | 1979-05-22 | W. R. Grace & Co. | Process for recovering dissolved iminodiacetonitrile from effluent liquors |
| DE2942437A1 (de) * | 1979-10-20 | 1981-04-23 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von iminodiacetonitril |
| US4895971A (en) * | 1988-10-31 | 1990-01-23 | W. R. Grace & Co.-Conn. | Process for the production of iminodiacetonitrile |
| US5008428A (en) * | 1989-10-26 | 1991-04-16 | W. R. Grace & Co.-Conn. | Integrated process for the production of aminoacetonitriles |
| EP0435334B1 (en) | 1989-12-29 | 1997-11-05 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing yellow colored cyan coupler |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA684850A (en) * | 1964-04-21 | Koenig Franz | Iminodiacetonitrile and a method of preparing same | |
| US2511487A (en) * | 1946-08-08 | 1950-06-13 | Du Pont | Synthesis of iminodiacetonitrile |
| US2794044A (en) * | 1955-08-30 | 1957-05-28 | Du Pont | Synthesis of iminodiacetonitrile |
| US3167580A (en) * | 1962-04-12 | 1965-01-26 | American Cyanamid Co | Process for the preparation of iminodiacetonitrile |
| US3412137A (en) * | 1965-10-14 | 1968-11-19 | Geigy Chemical Company | Process for the preparation of nitriles |
-
1976
- 1976-01-26 US US05/652,497 patent/US3993681A/en not_active Expired - Lifetime
- 1976-04-01 DE DE19762613994 patent/DE2613994A1/de not_active Withdrawn
- 1976-04-02 FR FR7609674A patent/FR2306198A1/fr active Granted
- 1976-04-02 SE SE7603952A patent/SE7603952L/xx not_active Application Discontinuation
- 1976-04-02 IE IE692/76A patent/IE43027B1/en unknown
- 1976-04-02 IT IT21918/76A patent/IT1059267B/it active
- 1976-04-02 JP JP51036185A patent/JPS51138618A/ja active Pending
- 1976-04-02 GB GB13484/76A patent/GB1525645A/en not_active Expired
- 1976-04-02 NL NL7603451A patent/NL7603451A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2613994A1 (de) | 1976-10-21 |
| IT1059267B (it) | 1982-05-31 |
| SE7603952L (sv) | 1976-10-05 |
| NL7603451A (nl) | 1976-10-06 |
| FR2306198B1 (enExample) | 1980-12-19 |
| US3993681A (en) | 1976-11-23 |
| FR2306198A1 (fr) | 1976-10-29 |
| GB1525645A (en) | 1978-09-20 |
| JPS51138618A (en) | 1976-11-30 |
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