NL8102190A - Werkwijze om sorbitol te bereiden door hydrogeneren van glucose. - Google Patents
Werkwijze om sorbitol te bereiden door hydrogeneren van glucose. Download PDFInfo
- Publication number
- NL8102190A NL8102190A NL8102190A NL8102190A NL8102190A NL 8102190 A NL8102190 A NL 8102190A NL 8102190 A NL8102190 A NL 8102190A NL 8102190 A NL8102190 A NL 8102190A NL 8102190 A NL8102190 A NL 8102190A
- Authority
- NL
- Netherlands
- Prior art keywords
- feed
- glucose
- sorbitol
- weight
- liquid
- Prior art date
Links
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims description 44
- 239000008103 glucose Substances 0.000 title claims description 43
- 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 title claims description 36
- 239000000600 sorbitol Substances 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000006243 chemical reaction Methods 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 34
- 239000007788 liquid Substances 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002772 monosaccharides Chemical class 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 150000001323 aldoses Chemical class 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- 150000005846 sugar alcohols Chemical class 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 229920001592 potato starch Polymers 0.000 claims description 2
- 239000011874 heated mixture Substances 0.000 claims 3
- 238000005267 amalgamation Methods 0.000 claims 1
- 229960001031 glucose Drugs 0.000 description 40
- 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 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- -1 glucose Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000013021 overheating Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 238000006227 trimethylsilylation reaction Methods 0.000 description 2
- SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 1
- RZYHXKLKJRGJGP-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C(F)(F)F RZYHXKLKJRGJGP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 229960000673 dextrose monohydrate Drugs 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material 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
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17446480 | 1980-08-01 | ||
| US06/174,464 US4322569A (en) | 1980-08-01 | 1980-08-01 | Catalytic hydrogenation of glucose to produce sorbitol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8102190A true NL8102190A (nl) | 1982-03-01 |
Family
ID=22636247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8102190A NL8102190A (nl) | 1980-08-01 | 1981-05-04 | Werkwijze om sorbitol te bereiden door hydrogeneren van glucose. |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4322569A (enExample) |
| JP (1) | JPS5745120A (enExample) |
| CA (1) | CA1173860A (enExample) |
| DE (1) | DE3110493A1 (enExample) |
| NL (1) | NL8102190A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6677271B1 (en) | 1999-03-03 | 2004-01-13 | Kataleuna Gmbh Catalysts | Nickel catalyst for hydrogenating functional groups and method for producing same |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4433184A (en) * | 1981-04-27 | 1984-02-21 | Hri, Inc. | Multi-stage catalytic conversion of aldoses to alditols |
| US4371616A (en) * | 1981-08-26 | 1983-02-01 | Hydrocarbon Research, Inc. | Process for producing L-sugars |
| DE3403973A1 (de) * | 1984-02-04 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung eines gemisches von (alpha)-d-glucopyranosido-1,6-mannit und (alpha)-d-glucopyranosido-1,6-sorbit aus (alpha)-d-glucopyranosido-1,6-fructose |
| DE3934457A1 (de) * | 1989-10-14 | 1991-04-18 | Bayer Ag | Verfahren zur herstellung von sorbitol (d-glucitol) aus (alpha)-d-glucose |
| US5162517A (en) * | 1989-10-14 | 1992-11-10 | Bayer Aktiengesellschaft | Process for the preparation of epimer-free sugar alcohols from the group consisting of xylitol, sorbitol (D-glucitol), 4-O-β-D-galactopyranosyl-D-glucitol and 4-O-α-D-glucopyranosyl-D-sorbitol |
| DE4416115A1 (de) * | 1994-05-06 | 1995-11-09 | Bayer Ag | Verfahren zur Herstellung von alpha-D-Glucopyranosido-1,6-mannit und -sorbit aus alpha-D-Glucopyranosido-1,6-fructose |
| DE4416408A1 (de) * | 1994-05-10 | 1995-11-16 | Bayer Ag | Verfahren zur Hydrierung von Zuckern |
| JP3793267B2 (ja) * | 1995-11-08 | 2006-07-05 | 東和化成工業株式会社 | ラネー触媒、その製造方法及びそれを使用した糖アルコールの製造方法 |
| DE19701991A1 (de) * | 1997-01-22 | 1998-07-23 | Bayer Ag | Verfahren zur Hydrierung von Zuckern |
| CA2318604C (en) | 1998-01-20 | 2007-04-10 | Grain Processing Corporation | Reduced malto-oligosaccharides |
| US6919446B1 (en) | 1998-01-20 | 2005-07-19 | Grain Processing Corp. | Reduced malto-oligosaccharides |
| US6780990B1 (en) | 1998-03-26 | 2004-08-24 | Spi Polyols, Inc. | Hydrogenated starch hydrolysate |
| US6380379B1 (en) | 1999-08-20 | 2002-04-30 | Grain Processing Corporation | Derivatized reduced malto-oligosaccharides |
| WO2001028325A2 (en) | 1999-10-20 | 2001-04-26 | Grain Processing Corporation | Compositions including reduced malto-oligosaccharide preserving agents |
| AU1099801A (en) | 1999-10-20 | 2001-04-30 | Grain Processing Corporation | Reduced malto-oligosaccharide cleansing compositions |
| US7026008B2 (en) * | 2001-09-13 | 2006-04-11 | Spi Polyols Inc. | Stable sugar-based hard candy having high index of whiteness |
| JP2004248673A (ja) * | 2003-02-19 | 2004-09-09 | Academia Sinica | でんぷん由来製品 |
| CN101432255B (zh) * | 2006-04-28 | 2013-04-24 | 株式会社可乐丽 | 3-甲基-1,5-戊二醇的制备方法 |
| FR2965819B1 (fr) * | 2010-10-08 | 2013-02-22 | Roquette Freres | Procede de fabrication de sirops de sorbitol de haute purete a partir de saccharose et utilisations |
| US9458476B2 (en) | 2011-04-18 | 2016-10-04 | R.J. Reynolds Tobacco Company | Method for producing glycerin from tobacco |
| US9289011B2 (en) | 2013-03-07 | 2016-03-22 | R.J. Reynolds Tobacco Company | Method for producing lutein from tobacco |
| US9265284B2 (en) | 2014-01-17 | 2016-02-23 | R.J. Reynolds Tobacco Company | Process for producing flavorants and related materials |
| BR112016018246B1 (pt) * | 2014-02-10 | 2021-06-01 | Archer Daniels Midland Company | Processo contínuo para hidrogenação do açúcar em uma alimentação de açúcar em água para um álcool de açúcar correspondente, processo contínuo para hidrogenação do açúcar em uma alimentação de açúcar em água para um álcool de açúcar correspondente, e processo para produção contínua de sorbitol |
| US10881133B2 (en) | 2015-04-16 | 2021-01-05 | R.J. Reynolds Tobacco Company | Tobacco-derived cellulosic sugar |
| US10499684B2 (en) | 2016-01-28 | 2019-12-10 | R.J. Reynolds Tobacco Company | Tobacco-derived flavorants |
| US11091446B2 (en) | 2017-03-24 | 2021-08-17 | R.J. Reynolds Tobacco Company | Methods of selectively forming substituted pyrazines |
| CN109305882B (zh) * | 2018-09-28 | 2023-12-19 | 吉林省石油化工设计研究院 | 一种葡萄糖连续加氢制备山梨醇的方法及装置 |
| CN110041169B (zh) * | 2019-05-14 | 2022-05-10 | 安徽师范大学 | 一种葡萄糖氢化反应液中山梨醇的分离方法 |
| CN110862298B (zh) * | 2019-11-08 | 2023-04-11 | 黑龙江新和成生物科技有限公司 | 一种山梨醇的制备方法 |
| CN110845303A (zh) * | 2019-11-30 | 2020-02-28 | 浙江华康药业股份有限公司 | 一种提高葡萄糖氢化效率的方法 |
| CN111024865B (zh) * | 2020-01-02 | 2022-07-15 | 四川金象赛瑞化工股份有限公司 | 一种生物质糖化液中糖含量的检测方法 |
| CN111206056B (zh) * | 2020-02-11 | 2022-03-04 | 浙江华康药业股份有限公司 | 一种利用麦芽糖醇色谱提余液制备山梨醇液和液体多元醇的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA582096A (en) * | 1959-08-25 | Alheritiere Louis | Process for producing polyalcohols, particularly sorbitol, by hydrogenation of sugars | |
| US1990245A (en) * | 1926-11-18 | 1935-02-05 | Ig Farbenindustrie Ag | Production of polyhydric alcohols |
| US1963999A (en) * | 1930-05-12 | 1934-06-26 | Du Pont | Process for producing polyhydroxy alcohols |
| US2650941A (en) * | 1950-04-06 | 1953-09-01 | Shell Dev | Conversion of carbohydrates to polyhydric alcohols |
| US2749371A (en) * | 1952-04-03 | 1956-06-05 | Atlas Powder Co | Hydrogenation of monosaccharides |
| US2868847A (en) * | 1956-10-05 | 1959-01-13 | Engelhard Ind Inc | Hydrogenation of mono-and disaccharides to polyols |
| US2968680A (en) * | 1958-12-04 | 1961-01-17 | Atlas Powder Co | Hydrogenation of carbohydrates |
| NL302696A (enExample) * | 1962-12-31 | |||
| US3538019A (en) * | 1968-03-07 | 1970-11-03 | Atlas Chem Ind | Nickel phosphate-promoted supported nickel catalyst |
| NL6812668A (en) * | 1968-09-05 | 1970-03-09 | Preparation of polyfunctional alcohols from oligo- - and/or polysaccharides |
-
1980
- 1980-08-01 US US06/174,464 patent/US4322569A/en not_active Expired - Lifetime
-
1981
- 1981-03-18 DE DE19813110493 patent/DE3110493A1/de not_active Withdrawn
- 1981-05-04 NL NL8102190A patent/NL8102190A/nl not_active Application Discontinuation
- 1981-07-15 JP JP56111531A patent/JPS5745120A/ja active Granted
- 1981-07-31 CA CA000383039A patent/CA1173860A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6677271B1 (en) | 1999-03-03 | 2004-01-13 | Kataleuna Gmbh Catalysts | Nickel catalyst for hydrogenating functional groups and method for producing same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0354091B2 (enExample) | 1991-08-19 |
| US4322569A (en) | 1982-03-30 |
| JPS5745120A (en) | 1982-03-13 |
| CA1173860A (en) | 1984-09-04 |
| DE3110493A1 (de) | 1982-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: HRI, INC. |
|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |