CA2074486C - Process for producing aminocarboxylic acid salt - Google Patents
Process for producing aminocarboxylic acid salt Download PDFInfo
- Publication number
- CA2074486C CA2074486C CA002074486A CA2074486A CA2074486C CA 2074486 C CA2074486 C CA 2074486C CA 002074486 A CA002074486 A CA 002074486A CA 2074486 A CA2074486 A CA 2074486A CA 2074486 C CA2074486 C CA 2074486C
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- catalyst
- aminoalcohol
- copper
- nickel
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 230000008569 process Effects 0.000 title claims abstract description 38
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 100
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 84
- 239000003054 catalyst Substances 0.000 claims abstract description 74
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 33
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000011541 reaction mixture Substances 0.000 claims abstract description 32
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052802 copper Inorganic materials 0.000 claims abstract description 23
- 239000010949 copper Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 12
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 7
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 claims abstract description 7
- 238000013019 agitation Methods 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 9
- -1 hydroxy-ethyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000002738 chelating agent Substances 0.000 abstract description 2
- 239000002778 food additive Substances 0.000 abstract description 2
- 235000013373 food additive Nutrition 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 150000001879 copper Chemical class 0.000 description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 6
- 229960004418 trolamine Drugs 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002332 glycine derivatives Chemical class 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 3
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 3
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 3
- XTYUEDCPRIMJNG-UHFFFAOYSA-N copper zirconium Chemical compound [Cu].[Zr] XTYUEDCPRIMJNG-UHFFFAOYSA-N 0.000 description 3
- HAXVIVNBOQIMTE-UHFFFAOYSA-L disodium;2-(carboxylatomethylamino)acetate Chemical compound [Na+].[Na+].[O-]C(=O)CNCC([O-])=O HAXVIVNBOQIMTE-UHFFFAOYSA-L 0.000 description 3
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 3
- 239000004247 glycine and its sodium salt Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229940029258 sodium glycinate Drugs 0.000 description 3
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910000990 Ni alloy Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- PIINGYXNCHTJTF-UHFFFAOYSA-N 2-(2-azaniumylethylamino)acetate Chemical compound NCCNCC(O)=O PIINGYXNCHTJTF-UHFFFAOYSA-N 0.000 description 1
- DHGYLUFLENKZHH-UHFFFAOYSA-N 2-(3-aminopropylamino)acetic acid Chemical compound NCCCNCC(O)=O DHGYLUFLENKZHH-UHFFFAOYSA-N 0.000 description 1
- GHKSKVKCKMGRDU-UHFFFAOYSA-N 2-(3-aminopropylamino)ethanol Chemical compound NCCCNCCO GHKSKVKCKMGRDU-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- RRWZZMHRVSMLCT-UHFFFAOYSA-N 2-(butylazaniumyl)acetate Chemical compound CCCCNCC(O)=O RRWZZMHRVSMLCT-UHFFFAOYSA-N 0.000 description 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
- NSZZKYYCIQQWKE-UHFFFAOYSA-N 2-(dibutylazaniumyl)acetate Chemical compound CCCCN(CC(O)=O)CCCC NSZZKYYCIQQWKE-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- RQSMGBAUYCTENZ-UHFFFAOYSA-N 2-(nonylamino)acetic acid Chemical compound CCCCCCCCCNCC(O)=O RQSMGBAUYCTENZ-UHFFFAOYSA-N 0.000 description 1
- KENZMUABEDKNJZ-UHFFFAOYSA-N 2-(nonylamino)ethanol Chemical compound CCCCCCCCCNCCO KENZMUABEDKNJZ-UHFFFAOYSA-N 0.000 description 1
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 1
- HEPOIJKOXBKKNJ-UHFFFAOYSA-N 2-(propan-2-ylazaniumyl)acetate Chemical compound CC(C)NCC(O)=O HEPOIJKOXBKKNJ-UHFFFAOYSA-N 0.000 description 1
- OECIDZZGUZGWNV-UHFFFAOYSA-N 2-[2-aminoethyl(ethyl)amino]acetic acid Chemical compound NCCN(CC)CC(O)=O OECIDZZGUZGWNV-UHFFFAOYSA-N 0.000 description 1
- PUIXOJJCTJVSBX-UHFFFAOYSA-N 2-[2-aminoethyl(ethyl)amino]ethanol Chemical compound NCCN(CC)CCO PUIXOJJCTJVSBX-UHFFFAOYSA-N 0.000 description 1
- HHRGNKUNRVABBN-UHFFFAOYSA-N 2-[2-hydroxyethyl(propan-2-yl)amino]ethanol Chemical compound OCCN(C(C)C)CCO HHRGNKUNRVABBN-UHFFFAOYSA-N 0.000 description 1
- ORSDUKBOFJDQEI-UHFFFAOYSA-N 2-[3-aminopropyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CCCN ORSDUKBOFJDQEI-UHFFFAOYSA-N 0.000 description 1
- UOQYWMZLTNEIFI-UHFFFAOYSA-N 2-[3-aminopropyl(methyl)amino]ethanol Chemical compound OCCN(C)CCCN UOQYWMZLTNEIFI-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- WWVBXWRCQNSAKA-UHFFFAOYSA-N 2-[butyl(carboxymethyl)amino]acetic acid Chemical compound CCCCN(CC(O)=O)CC(O)=O WWVBXWRCQNSAKA-UHFFFAOYSA-N 0.000 description 1
- QHHFAXFIUXRVSI-UHFFFAOYSA-N 2-[carboxymethyl(ethyl)amino]acetic acid Chemical compound OC(=O)CN(CC)CC(O)=O QHHFAXFIUXRVSI-UHFFFAOYSA-N 0.000 description 1
- XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 1
- IWJJXDLQNGBAOG-UHFFFAOYSA-N 2-[carboxymethyl(propan-2-yl)amino]acetic acid Chemical compound OC(=O)CN(C(C)C)CC(O)=O IWJJXDLQNGBAOG-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 1
- 108010065338 N-ethylglycine Proteins 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229940065285 cadmium compound Drugs 0.000 description 1
- 150000001662 cadmium compounds Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 108700003601 dimethylglycine Proteins 0.000 description 1
- XEQIERZCOHTONL-UHFFFAOYSA-L dipotassium;2-(carboxylatomethylamino)acetate Chemical compound [K+].[K+].[O-]C(=O)CNCC([O-])=O XEQIERZCOHTONL-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- GZWNUORNEQHOAW-UHFFFAOYSA-M potassium;2-aminoacetate Chemical compound [K+].NCC([O-])=O GZWNUORNEQHOAW-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32625190 | 1990-11-27 | ||
| JP2/326251 | 1990-11-27 | ||
| JP40877090 | 1990-12-28 | ||
| JP2/408770 | 1990-12-28 | ||
| JP3/113289 | 1991-05-17 | ||
| JP11328991 | 1991-05-17 | ||
| PCT/JP1991/001616 WO1992009559A1 (fr) | 1990-11-27 | 1991-11-26 | Procede de production de sel d'acide carboxylique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2074486A1 CA2074486A1 (en) | 1992-05-28 |
| CA2074486C true CA2074486C (en) | 2002-04-02 |
Family
ID=27312472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002074486A Expired - Lifetime CA2074486C (en) | 1990-11-27 | 1991-11-26 | Process for producing aminocarboxylic acid salt |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5220054A (enExample) |
| EP (1) | EP0513396B1 (enExample) |
| JP (1) | JP2939335B2 (enExample) |
| KR (1) | KR970009569B1 (enExample) |
| AU (1) | AU634918B2 (enExample) |
| CA (1) | CA2074486C (enExample) |
| DE (1) | DE69120660T2 (enExample) |
| DK (1) | DK0513396T3 (enExample) |
| ES (1) | ES2089493T3 (enExample) |
| WO (1) | WO1992009559A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2022044A6 (es) * | 1990-09-25 | 1991-11-16 | Ercros Sa | Procedimiento para la obtencion de derivados del acido acetico. |
| EP0620209B1 (en) * | 1993-04-12 | 1997-12-03 | Monsanto Company | Process to prepare carboxylic acid |
| BR9405924A (pt) * | 1993-04-12 | 1995-12-12 | Monsanto Co | Processo para preparar sais de ácido amino carboxilico |
| US5689000A (en) * | 1994-07-01 | 1997-11-18 | Monsanto Company | Process for preparing carboxylic acid salts and catalysts useful in such process |
| WO1998013140A1 (de) * | 1996-09-26 | 1998-04-02 | Akzo Nobel N.V. | Katalysator zur dehydrogenierung von aminoalkoholen zu aminocarbonsäuren oder von ethylenglykol(derivaten) zu oxycarbonsäuren, verfahren zu seiner herstellung und seine verwendung |
| ITTO980249A1 (it) * | 1998-03-23 | 1999-09-23 | Finchimica Srl | Procedimento per la preparazione di sali di acidi carbossilici |
| AR043078A1 (es) | 1998-09-14 | 2005-07-20 | Dow Agrosciences Llc | Procesos para preparar acidos carboxilicos |
| ES2274786T3 (es) * | 1999-05-03 | 2007-06-01 | Monsanto Technology Llc | Procedimiento de preparacion de sales de acido carboxilico a partir de alcoholes primarios. |
| ATE249419T1 (de) * | 1999-07-05 | 2003-09-15 | Atanor S A | Verfahren zur herstellung von amino-, imino-, und nitrilocarbonsäuren und für das verfahren mit silber aktivierter kupferkatalysator |
| US6376708B1 (en) * | 2000-04-11 | 2002-04-23 | Monsanto Technology Llc | Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts |
| CN100376326C (zh) * | 2006-03-30 | 2008-03-26 | 上海工程技术大学 | 负载型纳米铜镍催化剂制备方法及用于醇胺氧化脱氢反应 |
| DE102006016227A1 (de) * | 2006-04-06 | 2007-10-11 | Degussa Gmbh | Verfahren zur Herstellung von Kreatin, Kreatin-Monohydrat oder Guanidinoessigsäure |
| JP2012184213A (ja) * | 2010-04-06 | 2012-09-27 | Sumitomo Chemical Co Ltd | 含硫アミノ酸の製造方法 |
| RU2452565C1 (ru) * | 2011-02-16 | 2012-06-10 | Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН | Катализатор, способ его приготовления и способ получения динатриевой соли иминодиуксусной кислоты |
| JP6553988B2 (ja) * | 2015-08-28 | 2019-07-31 | 株式会社日本触媒 | アミノカルボン酸塩の製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3842081A (en) * | 1971-08-19 | 1974-10-15 | Jefferson Chem Co Inc | Preparation of aminocarboxylic acids from aminoalcohols |
| US3833650A (en) * | 1971-08-19 | 1974-09-03 | Jefferson Chem Co Inc | Preparation of nitrilotriacetic acid |
| JPS6041645A (ja) * | 1983-08-17 | 1985-03-05 | Nippon Shokubai Kagaku Kogyo Co Ltd | グリシン塩の製造方法 |
| JPS6041644A (ja) * | 1983-08-17 | 1985-03-05 | Nippon Shokubai Kagaku Kogyo Co Ltd | グリシン塩の製造方法 |
| GB2148287B (en) * | 1983-10-05 | 1987-04-15 | Nippon Catalytic Chem Ind | Preparation of aminocarboxylic acid salts from amino alcohols |
| JPS6078948A (ja) * | 1983-10-05 | 1985-05-04 | Nippon Shokubai Kagaku Kogyo Co Ltd | イミノジ酢酸塩の製造方法 |
| JPS60100545A (ja) * | 1983-11-08 | 1985-06-04 | Nippon Shokubai Kagaku Kogyo Co Ltd | ニトリロトリ酢酸塩の製造方法 |
| JPS6097945A (ja) * | 1983-11-01 | 1985-05-31 | Nippon Shokubai Kagaku Kogyo Co Ltd | ニトリロトリ酢酸塩の製造方法 |
| ES2022044A6 (es) * | 1990-09-25 | 1991-11-16 | Ercros Sa | Procedimiento para la obtencion de derivados del acido acetico. |
| ES2031412A6 (es) * | 1990-10-04 | 1992-12-01 | Ercros Sa | Perfeccionamientos introducidos en un procedimiento de obtencion de derivados de acido acetico. |
-
1991
- 1991-11-26 WO PCT/JP1991/001616 patent/WO1992009559A1/ja not_active Ceased
- 1991-11-26 AU AU89130/91A patent/AU634918B2/en not_active Expired
- 1991-11-26 DE DE69120660T patent/DE69120660T2/de not_active Revoked
- 1991-11-26 CA CA002074486A patent/CA2074486C/en not_active Expired - Lifetime
- 1991-11-26 JP JP4500538A patent/JP2939335B2/ja not_active Expired - Lifetime
- 1991-11-26 DK DK92902482.6T patent/DK0513396T3/da active
- 1991-11-26 US US07/915,803 patent/US5220054A/en not_active Expired - Lifetime
- 1991-11-26 KR KR1019920701772A patent/KR970009569B1/ko not_active Expired - Lifetime
- 1991-11-26 ES ES92902482T patent/ES2089493T3/es not_active Expired - Lifetime
- 1991-11-26 EP EP92902482A patent/EP0513396B1/en not_active Revoked
Also Published As
| Publication number | Publication date |
|---|---|
| KR970009569B1 (ko) | 1997-06-14 |
| KR920703200A (ko) | 1992-12-17 |
| DE69120660T2 (de) | 1996-10-31 |
| US5220054A (en) | 1993-06-15 |
| WO1992009559A1 (fr) | 1992-06-11 |
| EP0513396B1 (en) | 1996-07-03 |
| ES2089493T3 (es) | 1996-10-01 |
| EP0513396A4 (enExample) | 1994-02-23 |
| DE69120660D1 (de) | 1996-08-08 |
| AU8913091A (en) | 1992-06-25 |
| DK0513396T3 (da) | 1996-07-29 |
| CA2074486A1 (en) | 1992-05-28 |
| JP2939335B2 (ja) | 1999-08-25 |
| EP0513396A1 (en) | 1992-11-19 |
| AU634918B2 (en) | 1993-03-04 |
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| EEER | Examination request | ||
| MKEX | Expiry |