CA1070710A - Synthese du d-2-amino-1-butanol - Google Patents

Synthese du d-2-amino-1-butanol

Info

Publication number: CA1070710A
Authority: CA; Canada
Prior art keywords: butanol; amino; propyl; chloromethyl; acetamide
Prior art date: 1976-02-02
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

Application number

CA244,749A

Other languages

English (en)

Other versions

CA244749S (en

Inventor

Balwant Singh

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1976-02-02

Filing date

1976-02-02

Publication date

1980-01-29

1976-02-02 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1976-02-02 Priority to CA244,749A priority Critical patent/CA1070710A/fr

1980-01-29 Application granted granted Critical

1980-01-29 Publication of CA1070710A publication Critical patent/CA1070710A/fr

Status Expired legal-status Critical Current

Links

JCBPETKZIGVZRE-BYPYZUCNSA-N (2s)-2-aminobutan-1-ol Chemical compound CC[C@H](N)CO JCBPETKZIGVZRE-BYPYZUCNSA-N 0.000 title claims abstract description 12
230000015572 biosynthetic process Effects 0.000 title claims abstract description 8
238000003786 synthesis reaction Methods 0.000 title claims abstract description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 199
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 59
238000006243 chemical reaction Methods 0.000 claims abstract description 36
239000000460 chlorine Substances 0.000 claims abstract description 23
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 21
229910052801 chlorine Inorganic materials 0.000 claims abstract description 21
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 20
AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims abstract description 15
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims abstract description 6
239000001358 L(+)-tartaric acid Substances 0.000 claims abstract description 5
235000011002 L(+)-tartaric acid Nutrition 0.000 claims abstract description 5
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 80
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 62
229910001868 water Inorganic materials 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
TZUYFNORLRBWLP-UHFFFAOYSA-N ethanimidoyl chloride Chemical compound CC(Cl)=N TZUYFNORLRBWLP-UHFFFAOYSA-N 0.000 claims description 28
230000007062 hydrolysis Effects 0.000 claims description 24
238000006460 hydrolysis reaction Methods 0.000 claims description 24
238000000034 method Methods 0.000 claims description 21
PQBOTZNYFQWRHU-UHFFFAOYSA-N 1,2-dichlorobutane Chemical compound CCC(Cl)CCl PQBOTZNYFQWRHU-UHFFFAOYSA-N 0.000 claims description 16
230000008569 process Effects 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
OGIRFDHHRUMVGF-UHFFFAOYSA-N n-(1-chlorobutan-2-yl)ethanimidoyl chloride Chemical compound CCC(CCl)N=C(C)Cl OGIRFDHHRUMVGF-UHFFFAOYSA-N 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
ZMEGDKGDGOQGDK-SRRYXMDWSA-N [(2r)-1-hydroxybutan-2-yl]azanium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate Chemical compound CC[C@@H](N)CO.OC(=O)[C@H](O)[C@@H](O)C(O)=O ZMEGDKGDGOQGDK-SRRYXMDWSA-N 0.000 claims description 2
238000001704 evaporation Methods 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
238000007086 side reaction Methods 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims 2
HLJVYVLNPUSFJD-UHFFFAOYSA-N n-(1-chlorobutan-2-yl)acetamide Chemical compound CCC(CCl)NC(C)=O HLJVYVLNPUSFJD-UHFFFAOYSA-N 0.000 claims 2
239000000203 mixture Substances 0.000 abstract description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 25
239000000047 product Substances 0.000 abstract description 13
239000006227 byproduct Substances 0.000 abstract description 6
229960001618 ethambutol hydrochloride Drugs 0.000 abstract description 5
239000012458 free base Substances 0.000 abstract description 3
150000002825 nitriles Chemical class 0.000 abstract 1
JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 46
229940060038 chlorine Drugs 0.000 description 19
235000017168 chlorine Nutrition 0.000 description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000243 solution Substances 0.000 description 15
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 14
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 14
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
ORIVIUGYHFJFPH-UHFFFAOYSA-N 2-aminobutan-1-ol;hydrochloride Chemical compound Cl.CCC(N)CO ORIVIUGYHFJFPH-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 11
KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
238000004821 distillation Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
238000003756 stirring Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000007792 addition Methods 0.000 description 8
238000001914 filtration Methods 0.000 description 8
229960004592 isopropanol Drugs 0.000 description 8
239000012535 impurity Substances 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 6
239000000306 component Substances 0.000 description 6
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
229940095064 tartrate Drugs 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
239000007789 gas Substances 0.000 description 5
238000001030 gas--liquid chromatography Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
229940083608 sodium hydroxide Drugs 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
230000009850 completed effect Effects 0.000 description 4
-1 dl-2-amino-1-butanol hydrochloride methyl acetate Chemical compound 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229960001367 tartaric acid Drugs 0.000 description 4
235000002906 tartaric acid Nutrition 0.000 description 4
239000011975 tartaric acid Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000005292 vacuum distillation Methods 0.000 description 4
BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229960000285 ethambutol Drugs 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
229910000069 nitrogen hydride Inorganic materials 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OZHIYEINSCNALY-UHFFFAOYSA-N 1-aminobutan-1-ol Chemical compound CCCC(N)O OZHIYEINSCNALY-UHFFFAOYSA-N 0.000 description 2
KCFMGRDFBNKXFB-UHFFFAOYSA-N 1-chlorobutan-2-amine;hydrochloride Chemical compound Cl.CCC(N)CCl KCFMGRDFBNKXFB-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
229960004424 carbon dioxide Drugs 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229940057952 methanol Drugs 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000004064 recycling Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JCBPETKZIGVZRE-SCSAIBSYSA-N (2r)-2-aminobutan-1-ol Chemical compound CC[C@@H](N)CO JCBPETKZIGVZRE-SCSAIBSYSA-N 0.000 description 1
NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 description 1
ZZCLHOQBSJBENC-UHFFFAOYSA-N 1,2-dichlorobut-1-ene Chemical compound CCC(Cl)=CCl ZZCLHOQBSJBENC-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
RZJQLJVFNBPSRA-UHFFFAOYSA-N 2-aminobutyl acetate;hydrochloride Chemical compound Cl.CCC(N)COC(C)=O RZJQLJVFNBPSRA-UHFFFAOYSA-N 0.000 description 1
FLRAVPRRUDBVKJ-UHFFFAOYSA-N 4-Ethyl-2-methyloxazole Chemical compound CCC1=COC(C)=N1 FLRAVPRRUDBVKJ-UHFFFAOYSA-N 0.000 description 1
WSLPUXWJTSNFGB-UHFFFAOYSA-N 4-[2-(4-hydroxybutylamino)ethylamino]butan-1-ol Chemical compound OCCCCNCCNCCCCO WSLPUXWJTSNFGB-UHFFFAOYSA-N 0.000 description 1
XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 1
DBSGYNMYHMAOBW-UHFFFAOYSA-N 4-ethyl-2-methyl-4,5-dihydro-1,3-oxazole;hydrochloride Chemical compound Cl.CCC1COC(C)=N1 DBSGYNMYHMAOBW-UHFFFAOYSA-N 0.000 description 1
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
206010008583 Chloroma Diseases 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
241000518994 Conta Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
125000000783 acetimidoyl group Chemical group C(C)(=N)* 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
238000010923 batch production Methods 0.000 description 1
229960003563 calcium carbonate Drugs 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
235000011116 calcium hydroxide Nutrition 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
235000012255 calcium oxide Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
YITXTRUIAQZVFJ-UHFFFAOYSA-N n-(1-hydroxybutan-2-yl)acetamide Chemical compound CCC(CO)NC(C)=O YITXTRUIAQZVFJ-UHFFFAOYSA-N 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000002226 simultaneous effect Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910000018 strontium carbonate Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA244,749A 1976-02-02 1976-02-02 Synthese du d-2-amino-1-butanol Expired CA1070710A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA244,749A CA1070710A (fr)	1976-02-02	1976-02-02	Synthese du d-2-amino-1-butanol

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA244,749A CA1070710A (fr)	1976-02-02	1976-02-02	Synthese du d-2-amino-1-butanol

Publications (1)

Publication Number	Publication Date
CA1070710A true CA1070710A (fr)	1980-01-29

Family

ID=4105107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA244,749A Expired CA1070710A (fr)	1976-02-02	1976-02-02	Synthese du d-2-amino-1-butanol

Country Status (1)

Country	Link
CA (1)	CA1070710A (fr)

1976
- 1976-02-02 CA CA244,749A patent/CA1070710A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-01-29	MKEX	Expiry

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