JP2916256B2 - アミノカルボン酸塩の製造方法 - Google Patents
アミノカルボン酸塩の製造方法Info
- Publication number
- JP2916256B2 JP2916256B2 JP3516543A JP51654391A JP2916256B2 JP 2916256 B2 JP2916256 B2 JP 2916256B2 JP 3516543 A JP3516543 A JP 3516543A JP 51654391 A JP51654391 A JP 51654391A JP 2916256 B2 JP2916256 B2 JP 2916256B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- sodium
- catalyst
- selectivity
- copper
- 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
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 115
- 239000003054 catalyst Substances 0.000 claims description 48
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 150000001414 amino alcohols Chemical class 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- -1 hydroxyethyl group Chemical group 0.000 claims description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 17
- 229910052802 copper Inorganic materials 0.000 claims description 17
- 239000010949 copper Substances 0.000 claims description 17
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
- 238000002474 experimental method Methods 0.000 description 23
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- HAXVIVNBOQIMTE-UHFFFAOYSA-L disodium;2-(carboxylatomethylamino)acetate Chemical compound [Na+].[Na+].[O-]C(=O)CNCC([O-])=O HAXVIVNBOQIMTE-UHFFFAOYSA-L 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 230000035484 reaction time Effects 0.000 description 12
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 11
- 229910001388 sodium aluminate Inorganic materials 0.000 description 11
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- 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 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 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
- 239000002994 raw material Substances 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 239000007864 aqueous solution Substances 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
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical class [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 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 3
- PIINGYXNCHTJTF-UHFFFAOYSA-N 2-(2-azaniumylethylamino)acetate Chemical compound NCCNCC(O)=O PIINGYXNCHTJTF-UHFFFAOYSA-N 0.000 description 2
- DHGYLUFLENKZHH-UHFFFAOYSA-N 2-(3-aminopropylamino)acetic acid Chemical compound NCCCNCC(O)=O DHGYLUFLENKZHH-UHFFFAOYSA-N 0.000 description 2
- GHKSKVKCKMGRDU-UHFFFAOYSA-N 2-(3-aminopropylamino)ethanol Chemical compound NCCCNCCO GHKSKVKCKMGRDU-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 2
- 108010065338 N-ethylglycine Proteins 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000001879 copper Chemical class 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
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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
- 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
- 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
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical class [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005751 Copper oxide Substances 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
- 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
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-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
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940065285 cadmium compound Drugs 0.000 description 1
- 150000001662 cadmium compounds Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000002738 chelating agent Substances 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
- 229940116318 copper carbonate Drugs 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229910000431 copper oxide 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 108700003601 dimethylglycine Proteins 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 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
- 238000005470 impregnation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 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
- 229940078490 n,n-dimethylglycine Drugs 0.000 description 1
- 230000001590 oxidative effect Effects 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
- KVOIJEARBNBHHP-UHFFFAOYSA-N potassium;oxido(oxo)alumane Chemical compound [K+].[O-][Al]=O KVOIJEARBNBHHP-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
-
- 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
- B01J25/00—Catalysts of the Raney type
-
- 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
- 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
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3516543A JP2916256B2 (ja) | 1990-10-23 | 1991-10-21 | アミノカルボン酸塩の製造方法 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2-286670 | 1990-10-23 | ||
| JP28667090 | 1990-10-23 | ||
| PCT/JP1991/001440 WO1992006949A1 (en) | 1990-10-23 | 1991-10-21 | Process for producing salt of amino carboxylic acid |
| JP3516543A JP2916256B2 (ja) | 1990-10-23 | 1991-10-21 | アミノカルボン酸塩の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO1992006949A1 JPWO1992006949A1 (ja) | 1992-11-05 |
| JP2916256B2 true JP2916256B2 (ja) | 1999-07-05 |
Family
ID=17707441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3516543A Expired - Lifetime JP2916256B2 (ja) | 1990-10-23 | 1991-10-21 | アミノカルボン酸塩の製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5220055A (enExample) |
| EP (1) | EP0506973B1 (enExample) |
| JP (1) | JP2916256B2 (enExample) |
| KR (1) | KR950006892B1 (enExample) |
| AU (1) | AU636803B2 (enExample) |
| CA (1) | CA2071999C (enExample) |
| DE (1) | DE69115883T2 (enExample) |
| DK (1) | DK0506973T3 (enExample) |
| ES (1) | ES2081497T3 (enExample) |
| MX (1) | MX9101721A (enExample) |
| WO (1) | WO1992006949A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5602279A (en) * | 1986-04-15 | 1997-02-11 | Exxon Research And Engineering Company | Primary hindered aminoacids for promoted acid gas scrubbing process |
| US5292936A (en) * | 1993-04-12 | 1994-03-08 | Monsanto Company | Process to prepare amino carboxylic acid salts |
| BR9405924A (pt) * | 1993-04-12 | 1995-12-12 | Monsanto Co | Processo para preparar sais de ácido amino carboxilico |
| US5606512A (en) * | 1994-07-27 | 1997-02-25 | The Dow Chemical Company | Determining the biodegradability of iminodiacetic acid derivatives |
| EP0772771B2 (en) * | 1994-07-27 | 2003-12-17 | The Dow Chemical Company | Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof |
| US6159894A (en) * | 1996-09-26 | 2000-12-12 | Akzo Nobel Nv | Catalyst for dehydrogenation of amino alcohols to amino carboxylic acids or of ethylene glycol (derivatives) to oxycarboxylic acids, method for their production and their use |
| 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 |
| IL143139A0 (en) * | 1998-12-01 | 2002-04-21 | Syngenta Participations Ag | Process for the preparation of aminocarboxylic acids |
| CN1355783A (zh) * | 1999-05-03 | 2002-06-26 | 孟山都技术有限公司 | 从伯醇制备羧酸盐的方法 |
| US20020038051A1 (en) | 2000-02-18 | 2002-03-28 | Degussa-Huls Ag | Raney copper |
| EP1125634B1 (de) | 2000-02-18 | 2010-12-08 | Evonik Degussa GmbH | Geformter Festbettraney-Kupferkatalysator |
| US6376708B1 (en) * | 2000-04-11 | 2002-04-23 | Monsanto Technology Llc | Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts |
| CN1729052A (zh) | 2001-10-18 | 2006-02-01 | 孟山都技术公司 | 用于伯醇脱氢以制备羧酸盐的方法和催化剂 |
| WO2004035466A1 (en) * | 2002-10-18 | 2004-04-29 | Monsanto Technology Llc | Use of metal supported copper catalysts for reforming alcohols |
| MX2012010036A (es) | 2010-03-18 | 2012-09-21 | Basf Se | Procedimiento para preparar aminocarboxilatos con bajo contenido de subproductos. |
| US8785685B2 (en) | 2011-04-12 | 2014-07-22 | Basf Se | Process for preparing aminopolycarboxylates proceeding from amino acids |
| BR112013025242A2 (pt) | 2011-04-12 | 2016-12-27 | Basf Se | processo para a preparação de aminopolicarboxilatos provenientes de um aminoácido |
| US8609894B2 (en) | 2011-05-23 | 2013-12-17 | Basf Se | Process for preparing aminopolycarboxylates |
| ES2547919T3 (es) | 2011-05-23 | 2015-10-09 | Basf Se | Procedimiento para la preparación de aminopolicarboxilatos |
Family Cites Families (13)
| 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 |
| 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 |
| 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 |
| 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 |
| JPS6165840A (ja) * | 1984-09-07 | 1986-04-04 | Nippon Shokubai Kagaku Kogyo Co Ltd | ジグリコ−ル酸塩の製造方法 |
| 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. |
| JPH0641644A (ja) * | 1991-11-26 | 1994-02-15 | Nippon Steel Corp | 材質と表面品質の優れたＣｒ−Ｎｉ系ステンレス鋼薄板の製造方法 |
| JPH0641645A (ja) * | 1992-07-23 | 1994-02-15 | Mitsubishi Electric Corp | プレス加工用薄板の溶接部割れ防止方法及び溶接部の通電加熱焼鈍装置 |
| JPH06165840A (ja) * | 1992-10-29 | 1994-06-14 | Matsushita Electric Ind Co Ltd | クロロフロロカーボンの回収方法及びその再生方法 |
-
1991
- 1991-10-21 AU AU87117/91A patent/AU636803B2/en not_active Expired
- 1991-10-21 CA CA002071999A patent/CA2071999C/en not_active Expired - Lifetime
- 1991-10-21 US US07/861,893 patent/US5220055A/en not_active Expired - Lifetime
- 1991-10-21 DE DE69115883T patent/DE69115883T2/de not_active Expired - Lifetime
- 1991-10-21 ES ES91917813T patent/ES2081497T3/es not_active Expired - Lifetime
- 1991-10-21 WO PCT/JP1991/001440 patent/WO1992006949A1/ja not_active Ceased
- 1991-10-21 JP JP3516543A patent/JP2916256B2/ja not_active Expired - Lifetime
- 1991-10-21 DK DK91917813.7T patent/DK0506973T3/da active
- 1991-10-21 EP EP91917813A patent/EP0506973B1/en not_active Expired - Lifetime
- 1991-10-21 KR KR1019920701507A patent/KR950006892B1/ko not_active Expired - Lifetime
- 1991-10-23 MX MX9101721A patent/MX9101721A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0506973A1 (en) | 1992-10-07 |
| CA2071999A1 (en) | 1992-04-24 |
| DE69115883D1 (de) | 1996-02-08 |
| EP0506973B1 (en) | 1995-12-27 |
| US5220055A (en) | 1993-06-15 |
| CA2071999C (en) | 1995-11-21 |
| AU8711791A (en) | 1992-05-20 |
| EP0506973A4 (enExample) | 1994-02-23 |
| DE69115883T2 (de) | 1996-06-05 |
| KR927003515A (ko) | 1992-12-18 |
| KR950006892B1 (ko) | 1995-06-26 |
| DK0506973T3 (da) | 1996-01-29 |
| AU636803B2 (en) | 1993-05-06 |
| ES2081497T3 (es) | 1996-03-16 |
| MX9101721A (es) | 1992-06-05 |
| WO1992006949A1 (en) | 1992-04-30 |
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