JPH057388B2 - - Google Patents
Info
- Publication number
- JPH057388B2 JPH057388B2 JP1989683A JP1989683A JPH057388B2 JP H057388 B2 JPH057388 B2 JP H057388B2 JP 1989683 A JP1989683 A JP 1989683A JP 1989683 A JP1989683 A JP 1989683A JP H057388 B2 JPH057388 B2 JP H057388B2
- Authority
- JP
- Japan
- Prior art keywords
- amine
- ascorbic acid
- carbon atoms
- formula
- mixture
- 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
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 51
- 150000001412 amines Chemical class 0.000 claims description 43
- 229960005070 ascorbic acid Drugs 0.000 claims description 41
- 235000010323 ascorbic acid Nutrition 0.000 claims description 41
- 239000011668 ascorbic acid Substances 0.000 claims description 41
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- -1 ketogulonic acid ester Chemical class 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 7
- RGHNJXZEOKUKBD-KKQCNMDGSA-N D-gulonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-KKQCNMDGSA-N 0.000 claims description 6
- 150000003973 alkyl amines Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 6
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 6
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 claims description 5
- 230000029087 digestion Effects 0.000 claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- DTGGNTMERRTPLR-UHFFFAOYSA-N 1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=CC=C1 DTGGNTMERRTPLR-UHFFFAOYSA-N 0.000 claims description 2
- QKVUSSUOYHTOFQ-UHFFFAOYSA-N 3-methyl-n,n-bis(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCN(CCC(C)C)CCC(C)C QKVUSSUOYHTOFQ-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 claims description 2
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 claims description 2
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 2
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- 238000010992 reflux Methods 0.000 description 33
- 238000000605 extraction Methods 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000012071 phase Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000006277 sulfonation reaction Methods 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- XKJLTJCYZRLXMM-JGWLITMVSA-N methyl (2r,3r,4s,5r)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound COC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO XKJLTJCYZRLXMM-JGWLITMVSA-N 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000008707 rearrangement Effects 0.000 description 7
- 229920001429 chelating resin Polymers 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- AZLWQVJVINEILY-UHFFFAOYSA-N 2-(2-dodecoxyethoxy)ethanol Chemical compound CCCCCCCCCCCCOCCOCCO AZLWQVJVINEILY-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- QBBRCDKRUGWCFL-XZBKPIIZSA-N ethyl (2r,3r,4s,5r)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound CCOC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO QBBRCDKRUGWCFL-XZBKPIIZSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UXQFKZKMNYRRAS-ULAWRXDQSA-N CC(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO Chemical compound CC(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO UXQFKZKMNYRRAS-ULAWRXDQSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH89182 | 1982-02-12 | ||
CH891/82-3 | 1982-02-12 | ||
CH7218/82-4 | 1982-12-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58148873A JPS58148873A (ja) | 1983-09-05 |
JPH057388B2 true JPH057388B2 (fr) | 1993-01-28 |
Family
ID=4197584
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1989683A Granted JPS58148873A (ja) | 1982-02-12 | 1983-02-10 | アスコルビン酸の製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58148873A (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE40356T1 (de) * | 1983-08-05 | 1989-02-15 | Hoffmann La Roche | Verfahren zur herstellung von kohlenhydraten. |
EP2274435A4 (fr) * | 2008-05-07 | 2012-06-20 | Zeachem Inc | Récupération d'acides organiques |
-
1983
- 1983-02-10 JP JP1989683A patent/JPS58148873A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS58148873A (ja) | 1983-09-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5041563A (en) | Rearrangement process | |
EP0103400A1 (fr) | Procédé pour la préparation de carbohydrazide | |
US4868322A (en) | Process for preparing trithiocarbonic acid diesters | |
US20050203287A1 (en) | Process for the preparation of sulfamate derivatives | |
JPH057388B2 (fr) | ||
JPH0533228B2 (fr) | ||
US5565615A (en) | Method of preparing dimethylamine-borane | |
US3448137A (en) | Method of preparing 4-alkyl-2,2-dimethyl-2-silamorpholines | |
US4486599A (en) | Process for preparing the 2',4'-difluoro-4-hydroxy-(1,1'-diphenyl)-3-carboxylic acid | |
US6545172B1 (en) | Processes for the production of methyl dithiocarbazinate | |
KR840000115B1 (ko) | 카바졸 유도체의 제조방법 | |
US3305549A (en) | Production of substituted biurets | |
JPH082848B2 (ja) | 4−ニトロソジフェニルアミン類の製造法 | |
US3136800A (en) | Method for producing hydroxythiobenzoic acids and esters thereof | |
US4091033A (en) | Method of making 2-alkoxy-2,3-dihydro-benzofuran-5-ols and their alkyl sulfonic acid esters | |
CA1068288A (fr) | 2-alkyle inferieur-2,3-dihydro-5-benzofuranylesters d'acides sulfoniques composes d'alkyles inferieurs | |
IL27766A (en) | Process for the preparation of 3,4-dihydro-4-oxo-1,2,3-benzotriazinyl-3-yl methyl thionothiol-phosphoric(-phosphonic,-phosphinic)acid esters | |
KR0174333B1 (ko) | 플루오란계 염료의 제조방법 | |
GB2160204A (en) | Preparation of N-methyl-1-alkylthio-2-nitroethenamines | |
EP0163506B1 (fr) | Méthode de préparation d'un acide pyridyl propanoique | |
KR890002250B1 (ko) | 트리아진유도체의 새로운 제조방법 | |
SU469689A1 (ru) | Способ получени о-арилкетоксимов | |
RU1773912C (ru) | Способ получени @ -трифторацетил- @ -бутиролактона | |
JP3530925B2 (ja) | オキソエステル化合物の製造方法 | |
JPH0236178A (ja) | 4−ヒドロキシクマリンの製造法 |