NO117922B - - Google Patents
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- Publication number
- NO117922B NO117922B NO165045A NO16504566A NO117922B NO 117922 B NO117922 B NO 117922B NO 165045 A NO165045 A NO 165045A NO 16504566 A NO16504566 A NO 16504566A NO 117922 B NO117922 B NO 117922B
- Authority
- NO
- Norway
- Prior art keywords
- nitrilotriacetonitrile
- acid
- reaction
- hydrocyanic acid
- reaction mixture
- Prior art date
Links
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 46
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 41
- LJAIDEYQVIJERM-UHFFFAOYSA-N 2-[bis(cyanomethyl)amino]acetonitrile Chemical compound N#CCN(CC#N)CC#N LJAIDEYQVIJERM-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
- 235000011130 ammonium sulphate Nutrition 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001166 ammonium sulphate Substances 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- IIWRMQTWWQPYOO-UHFFFAOYSA-N 2-[(cyanomethylamino)methylamino]acetonitrile Chemical compound N#CCNCNCC#N IIWRMQTWWQPYOO-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0057699 | 1965-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117922B true NO117922B (es) | 1969-10-13 |
Family
ID=7228364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO165045A NO117922B (es) | 1965-11-20 | 1966-10-07 |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT266811B (es) |
| BE (1) | BE689921A (es) |
| CH (1) | CH487127A (es) |
| DE (1) | DE1493910C3 (es) |
| ES (1) | ES333278A1 (es) |
| FR (1) | FR1500686A (es) |
| GB (1) | GB1115980A (es) |
| NL (1) | NL6616101A (es) |
| NO (1) | NO117922B (es) |
| SE (1) | SE320384B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856844A (en) * | 1970-12-11 | 1974-12-24 | Ethyl Corp | Chemical process |
| DE3029205A1 (de) * | 1980-08-01 | 1982-03-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von aminonitrilen |
| US4485049A (en) * | 1983-01-03 | 1984-11-27 | Monsanto Company | Two-stage crystallization of nitrilotriacetonitrile from a hot solution |
-
1965
- 1965-11-20 DE DE1493910A patent/DE1493910C3/de not_active Expired
-
1966
- 1966-10-07 NO NO165045A patent/NO117922B/no unknown
- 1966-10-20 SE SE14322/66A patent/SE320384B/xx unknown
- 1966-11-10 CH CH1616566A patent/CH487127A/de not_active IP Right Cessation
- 1966-11-11 ES ES0333278A patent/ES333278A1/es not_active Expired
- 1966-11-15 NL NL6616101A patent/NL6616101A/xx unknown
- 1966-11-16 GB GB51359/66A patent/GB1115980A/en not_active Expired
- 1966-11-17 FR FR84033A patent/FR1500686A/fr not_active Expired
- 1966-11-18 AT AT1067366A patent/AT266811B/de active
- 1966-11-18 BE BE689921D patent/BE689921A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1493910A1 (de) | 1969-12-11 |
| FR1500686A (fr) | 1967-11-03 |
| DE1493910B2 (de) | 1973-09-13 |
| GB1115980A (en) | 1968-06-06 |
| DE1493910C3 (de) | 1974-04-11 |
| SE320384B (es) | 1970-02-09 |
| CH487127A (de) | 1970-03-15 |
| BE689921A (es) | 1967-05-02 |
| NL6616101A (es) | 1967-05-22 |
| AT266811B (de) | 1968-12-10 |
| ES333278A1 (es) | 1967-07-16 |
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