JPH0259832B2 - - Google Patents
Info
- Publication number
- JPH0259832B2 JPH0259832B2 JP57063959A JP6395982A JPH0259832B2 JP H0259832 B2 JPH0259832 B2 JP H0259832B2 JP 57063959 A JP57063959 A JP 57063959A JP 6395982 A JP6395982 A JP 6395982A JP H0259832 B2 JPH0259832 B2 JP H0259832B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- sorbitol
- polyhydric alcohol
- formula
- weight
- 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
Links
- 238000006243 chemical reaction Methods 0.000 claims description 71
- 229960002920 sorbitol Drugs 0.000 claims description 41
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 33
- 239000000600 sorbitol Substances 0.000 claims description 33
- 150000005846 sugar alcohols Polymers 0.000 claims description 30
- 239000000811 xylitol Substances 0.000 claims description 27
- 229960002675 xylitol Drugs 0.000 claims description 27
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 239000003377 acid catalyst Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000012431 aqueous reaction media Substances 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- -1 methoxy, ethoxy Chemical group 0.000 description 25
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 23
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 23
- 235000010447 xylitol Nutrition 0.000 description 23
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 16
- HZVFRKSYUGFFEJ-YVECIDJPSA-N (2r,3r,4s,5r)-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=CC1=CC=CC=C1 HZVFRKSYUGFFEJ-YVECIDJPSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 9
- VKFWQGFYGLIANZ-WOPDTQHZSA-N (2r,3s,4r)-6-phenylhex-5-ene-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C(O)=CC1=CC=CC=C1 VKFWQGFYGLIANZ-WOPDTQHZSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- FMZUHGYZWYNSOA-VVBFYGJXSA-N (1r)-1-[(4r,4ar,8as)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical compound C([C@@H]1OC(O[C@@H]([C@@H]1O1)[C@H](O)CO)C=2C=CC=CC=2)OC1C1=CC=CC=C1 FMZUHGYZWYNSOA-VVBFYGJXSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229940087101 dibenzylidene sorbitol Drugs 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000013081 microcrystal Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXNWJSNQLUUFMR-ZZVYKPCYSA-N (2R,3R,4S,5R)-5-methyl-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical compound C[C@@](C(O)=CC1=CC=CC=C1)(O)[C@@H](O)[C@H](O)[C@H](O)CO YXNWJSNQLUUFMR-ZZVYKPCYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920005672 polyolefin resin Polymers 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- QJBBDEZQLAJWDC-XEZLXBQYSA-N (2R,3R,4S,5S)-5-chloro-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical compound Cl[C@@](C(O)=CC1=CC=CC=C1)(O)[C@@H](O)[C@H](O)[C@H](O)CO QJBBDEZQLAJWDC-XEZLXBQYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QMDPLUNYAOTGEC-RZFFKMDDSA-N C(C)[C@@](C(O)=CC1=CC=CC=C1)(O)[C@@H](O)[C@H](O)[C@H](O)CO Chemical compound C(C)[C@@](C(O)=CC1=CC=CC=C1)(O)[C@@H](O)[C@H](O)[C@H](O)CO QMDPLUNYAOTGEC-RZFFKMDDSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- VMEDNHPHBDLILA-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound C(=O)(O)C1=CC=C(C=O)C=C1.C(=O)(O)C1=CC=C(C=O)C=C1 VMEDNHPHBDLILA-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007562 laser obscuration time method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57063959A JPS58180488A (ja) | 1982-04-19 | 1982-04-19 | 多価アルコ−ル誘導体及びその製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57063959A JPS58180488A (ja) | 1982-04-19 | 1982-04-19 | 多価アルコ−ル誘導体及びその製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58180488A JPS58180488A (ja) | 1983-10-21 |
| JPH0259832B2 true JPH0259832B2 (enrdf_load_stackoverflow) | 1990-12-13 |
Family
ID=13244353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57063959A Granted JPS58180488A (ja) | 1982-04-19 | 1982-04-19 | 多価アルコ−ル誘導体及びその製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58180488A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6548581B2 (en) | 2001-03-23 | 2003-04-15 | Milliken & Company | Asymmetric halogen-alkyl alditol derivatives as nucleators and clarifiers for polyolefins, and polyolefin plastic compositions containing same |
| US6894176B2 (en) | 2001-03-23 | 2005-05-17 | Milliken & Company | Reaction product mixtures including both symmetric compounds and asymmetric dipolar multi-substituted alditol derivatives |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562265A (en) * | 1979-10-11 | 1985-12-31 | Milliken Research Corporation | Method for producing a di-acetal of sorbitol and an aromatic aldehyde |
| JPS60260501A (ja) * | 1984-06-07 | 1985-12-23 | Shinto Paint Co Ltd | 固型かび防止塗料 |
| US4996334A (en) * | 1988-02-05 | 1991-02-26 | Mitsubishi Petrochemical Co., Ltd. | Sorbitol derivatives |
| DE69028545T2 (de) * | 1990-08-27 | 1997-04-30 | New Japan Chem Co Ltd | Verfahren zur herstellung von acetalen |
| JP3067972B2 (ja) * | 1995-03-03 | 2000-07-24 | 新日本理化株式会社 | ジアセタールの六方晶結晶、該六方晶結晶を含む核剤、該六方晶結晶を含むポリオレフィン系樹脂組成物及び成形物、並びに該組成物の成形方法 |
-
1982
- 1982-04-19 JP JP57063959A patent/JPS58180488A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6548581B2 (en) | 2001-03-23 | 2003-04-15 | Milliken & Company | Asymmetric halogen-alkyl alditol derivatives as nucleators and clarifiers for polyolefins, and polyolefin plastic compositions containing same |
| US6894176B2 (en) | 2001-03-23 | 2005-05-17 | Milliken & Company | Reaction product mixtures including both symmetric compounds and asymmetric dipolar multi-substituted alditol derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58180488A (ja) | 1983-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH07107067B2 (ja) | アセタール類の製造方法 | |
| JPH0259832B2 (enrdf_load_stackoverflow) | ||
| JP5014724B2 (ja) | ジオキサングリコールの製造方法 | |
| KR100441795B1 (ko) | 트리글리시딜 이소시아누레이트의 제조방법 | |
| JP3223377B2 (ja) | 対称的な２，２’−メチレンビスベンゾトリアゾリル フェノール類の製造方法 | |
| JP3069297B2 (ja) | ポリエステルの製造方法 | |
| JP2895959B2 (ja) | スルホニウム塩の製造方法 | |
| JP3876933B2 (ja) | 硫酸水素エステルの製造方法 | |
| JP2927880B2 (ja) | ４，４’‐ジヒドロキシ‐３，３’，５，５’‐テトラメチルジフェニルメタンの製造方法 | |
| JP2002534495A (ja) | アゾイミノエーテル及びアゾカルボン酸エステルの製造方法並びに新規のアゾカルボン酸混合エステル | |
| JPS60132933A (ja) | ニトロジアリ‐ルアミンの製造方法 | |
| JPS58203934A (ja) | １−ヒドロキシケトンの製法 | |
| JP3944876B2 (ja) | クエン酸エステル類の製造方法 | |
| JP2717995B2 (ja) | １，２，３−トリアゾールの製法 | |
| JP3219256B2 (ja) | ビス（ｐ−ヒドロキシフェニル）酢酸の製造方法 | |
| RU2147020C1 (ru) | Способ получения гидразидов алифатических карбоновых кислот и их смесей | |
| CN118146181A (zh) | 4-溴苯酐及其合成方法 | |
| US4127735A (en) | Preparation of dichlorophene | |
| KR0169558B1 (ko) | 2-아미노-3,5- 디브로모 벤즈알데히드의 제조방법 | |
| US2782231A (en) | Preparation of malonanilic acid and substituted malonanilic acids | |
| JPH0372066B2 (enrdf_load_stackoverflow) | ||
| CN119698404A (zh) | 用于制备和分离某些介离子类杀有害生物剂的中间体的方法 | |
| JPH0525876B2 (enrdf_load_stackoverflow) | ||
| JPH0366659A (ja) | イセチオン酸の製造方法 | |
| JPS60166673A (ja) | ３−位が置換された２（３ｈ）−ベンズチアゾロンの製造方法 |