BE592674A - - Google Patents

Info

Publication number

BE592674A

BE592674A BE592674DA BE592674A BE 592674 A BE592674 A BE 592674A BE 592674D A BE592674D A BE 592674DA BE 592674 A BE592674 A BE 592674A

Authority

BE

Belgium

Prior art keywords

lysine

hydrolysis

caprolactam

amino

temperature

Prior art date

Links

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• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 24
• 239000004472 Lysine Substances 0.000 claims description 18
• 230000007062 hydrolysis Effects 0.000 claims description 17
• 238000006460 hydrolysis reaction Methods 0.000 claims description 17
• 238000000034 method Methods 0.000 claims description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
• 235000019766 L-Lysine Nutrition 0.000 claims description 7
• 150000001875 compounds Chemical class 0.000 claims description 7
• 239000011541 reaction mixture Substances 0.000 claims description 7
• 238000009835 boiling Methods 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 150000001768 cations Chemical class 0.000 claims description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• 239000002585 base Substances 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 11
• 235000018977 lysine Nutrition 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• SCWWKKUJPHRBRV-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;sodium Chemical compound [Na].NCCCC[C@H](N)C(O)=O SCWWKKUJPHRBRV-JEDNCBNOSA-N 0.000 description 3
• BOWUOGIPSRVRSJ-UHFFFAOYSA-N 2-aminohexano-6-lactam Chemical compound NC1CCCCNC1=O BOWUOGIPSRVRSJ-UHFFFAOYSA-N 0.000 description 3
• BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 235000001014 amino acid Nutrition 0.000 description 3
• 150000001413 amino acids Chemical class 0.000 description 3
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
• 239000000920 calcium hydroxide Substances 0.000 description 3
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
• 230000006340 racemization Effects 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 239000006227 byproduct Substances 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 235000013305 food Nutrition 0.000 description 2
• 238000001640 fractional crystallisation Methods 0.000 description 2
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• JBBURJFZIMRPCZ-XRIGFGBMSA-N (2s)-2,6-diaminohexanoic acid;hydron;dichloride Chemical compound Cl.Cl.NCCCC[C@H](N)C(O)=O JBBURJFZIMRPCZ-XRIGFGBMSA-N 0.000 description 1
• CWPDRBAWZYJDEH-YFKPBYRVSA-N (2s)-2,6-diaminohexanoyl chloride Chemical compound NCCCC[C@H](N)C(Cl)=O CWPDRBAWZYJDEH-YFKPBYRVSA-N 0.000 description 1
• RQBNXPJPWKUTOG-UHFFFAOYSA-N Azabon Chemical compound C1=CC(N)=CC=C1S(=O)(=O)N1CC(CC2)CCC2C1 RQBNXPJPWKUTOG-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 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 1
• -1 L-lysine compound Chemical class 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 230000000996 additive effect Effects 0.000 description 1
• RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
• 229910001863 barium hydroxide Inorganic materials 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
• 239000000292 calcium oxide Substances 0.000 description 1
• ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
• KXFZYFOJZITHNT-JEDNCBNOSA-N calcium;(2s)-2,6-diaminohexanoic acid Chemical compound [Ca].NCCCC[C@H](N)C(O)=O KXFZYFOJZITHNT-JEDNCBNOSA-N 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 235000018102 proteins Nutrition 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 238000009834 vaporization Methods 0.000 description 1
• 230000008016 vaporization Effects 0.000 description 1