CN1152913A - 制备3-(甲硫基)丙醛的方法 - Google Patents
制备3-(甲硫基)丙醛的方法 Download PDFInfo
- Publication number
- CN1152913A CN1152913A CN95194068A CN95194068A CN1152913A CN 1152913 A CN1152913 A CN 1152913A CN 95194068 A CN95194068 A CN 95194068A CN 95194068 A CN95194068 A CN 95194068A CN 1152913 A CN1152913 A CN 1152913A
- Authority
- CN
- China
- Prior art keywords
- gas
- liquid
- propenal
- product
- reaction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 99
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 230000008569 process Effects 0.000 title abstract description 16
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 650
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 299
- 239000007788 liquid Substances 0.000 claims abstract description 260
- 238000006243 chemical reaction Methods 0.000 claims abstract description 130
- 239000000047 product Substances 0.000 claims abstract description 119
- 239000012429 reaction media Substances 0.000 claims abstract description 88
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 239000007789 gas Substances 0.000 claims description 361
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 89
- 230000004087 circulation Effects 0.000 claims description 57
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 50
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 42
- 238000001816 cooling Methods 0.000 claims description 24
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 21
- 238000009833 condensation Methods 0.000 claims description 19
- 230000005494 condensation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 16
- 239000007859 condensation product Substances 0.000 claims description 15
- -1 methylthio group acetal Chemical class 0.000 claims description 14
- 239000000112 cooling gas Substances 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 11
- 230000008859 change Effects 0.000 claims description 10
- 230000002411 adverse Effects 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- 230000011218 segmentation Effects 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000012809 cooling fluid Substances 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 60
- 150000001299 aldehydes Chemical class 0.000 description 57
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 57
- 239000007791 liquid phase Substances 0.000 description 47
- 239000012071 phase Substances 0.000 description 42
- 238000012546 transfer Methods 0.000 description 38
- 230000035611 feeding Effects 0.000 description 36
- 239000000203 mixture Substances 0.000 description 36
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 30
- 238000007600 charging Methods 0.000 description 30
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 24
- 230000008676 import Effects 0.000 description 21
- 238000011084 recovery Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 14
- 241000282326 Felis catus Species 0.000 description 12
- 239000001294 propane Substances 0.000 description 12
- 239000012535 impurity Substances 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 230000036961 partial effect Effects 0.000 description 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 7
- 229930182817 methionine Natural products 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000007599 discharging Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000012495 reaction gas Substances 0.000 description 6
- 230000009466 transformation Effects 0.000 description 6
- 230000005514 two-phase flow Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000413 hydrolysate Substances 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- CQSQMXIROIYTLO-UHFFFAOYSA-N 2-methylpropanethial Chemical compound CC(C)C=S CQSQMXIROIYTLO-UHFFFAOYSA-N 0.000 description 1
- NPZWCFUWRHEFCH-UHFFFAOYSA-N 4-hydroxypentanethioic S-acid Chemical compound CC(O)CCC(S)=O NPZWCFUWRHEFCH-UHFFFAOYSA-N 0.000 description 1
- 241001522083 Citrus trifoliata Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000000404 Poncirus trifoliata Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012705 liquid precursor Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- RECVMTHOQWMYFX-UHFFFAOYSA-N oxygen(1+) dihydride Chemical compound [OH2+] RECVMTHOQWMYFX-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27321694A | 1994-07-11 | 1994-07-11 | |
| US08/273,216 | 1994-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1152913A true CN1152913A (zh) | 1997-06-25 |
Family
ID=23043005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95194068A Pending CN1152913A (zh) | 1994-07-11 | 1995-07-06 | 制备3-(甲硫基)丙醛的方法 |
Country Status (10)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102633698A (zh) * | 2012-04-28 | 2012-08-15 | 重庆紫光天化蛋氨酸有限责任公司 | 甲硫醇和丙烯醛合成的粗甲硫基代丙醛的处理方法和系统 |
| CN103476747A (zh) * | 2010-12-28 | 2013-12-25 | 赢创德固赛有限公司 | 甲硫基丙醛的制备方法 |
| CN105136942A (zh) * | 2015-08-27 | 2015-12-09 | 天津春发生物科技集团有限公司 | 一种2,3-二甲基吡嗪的分析检测方法 |
| CN109160893A (zh) * | 2018-10-15 | 2019-01-08 | 禄丰天宝磷化工有限公司 | 一种甲硒基丙醛的制备方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5905171A (en) * | 1995-06-22 | 1999-05-18 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5925794A (en) * | 1993-06-08 | 1999-07-20 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5825369A (en) * | 1996-01-16 | 1998-10-20 | International Business Machines Corporation | Compression of simple geometric models using spanning trees |
| FR2835831B1 (fr) * | 2002-02-12 | 2006-09-01 | Aventis Animal Nutrition Sa | Procede de purification de l'acroleine |
| US7866867B2 (en) | 2009-03-09 | 2011-01-11 | Taiwan Plastic Optical Fiber Co., Ltd. | Backlighting optical fiber, and a LCD backlight module and display device formed therefrom |
| JP2011093839A (ja) * | 2009-10-29 | 2011-05-12 | Sumitomo Chemical Co Ltd | ３−メチルチオプロパナールの製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES357862A1 (es) * | 1967-10-13 | 1970-04-01 | Glanzstoff Ag | Procedimiento para la fabricacion de beta metilmecaptopro- pionaldehido. |
| FR2314917A1 (fr) * | 1975-06-20 | 1977-01-14 | Rhone Poulenc Ind | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
| FR2460925A1 (fr) * | 1979-07-10 | 1981-01-30 | Rhone Poulenc Ind | Procede de preparation directe d'aldehyde beta-methylthiopropionique |
| US5015776A (en) * | 1986-10-28 | 1991-05-14 | Atochem North America, Inc. | Preparation of 3-(alkylthio) aldehydes |
| US4944853A (en) * | 1989-09-11 | 1990-07-31 | Pennwalt Corporation | Photochemical preparation of 3-(organothio) aldehydes |
| US5352837A (en) * | 1993-06-08 | 1994-10-04 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
-
1995
- 1995-07-06 CN CN95194068A patent/CN1152913A/zh active Pending
- 1995-07-06 EP EP95926631A patent/EP0770062A4/en not_active Withdrawn
- 1995-07-06 MX MX9700276A patent/MX9700276A/es unknown
- 1995-07-06 KR KR1019970700180A patent/KR970704681A/ko not_active Abandoned
- 1995-07-06 WO PCT/US1995/008532 patent/WO1996001810A1/en active IP Right Grant
- 1995-07-06 AU AU30939/95A patent/AU699841B2/en not_active Ceased
- 1995-07-06 RU RU97102147/04A patent/RU2149159C1/ru not_active IP Right Cessation
- 1995-07-06 JP JP8504405A patent/JPH10504812A/ja active Pending
- 1995-07-06 PL PL95318213A patent/PL318213A1/xx unknown
- 1995-07-26 TW TW084107746A patent/TW296373B/zh active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103476747A (zh) * | 2010-12-28 | 2013-12-25 | 赢创德固赛有限公司 | 甲硫基丙醛的制备方法 |
| CN103476747B (zh) * | 2010-12-28 | 2016-01-20 | 赢创德固赛有限公司 | 甲硫基丙醛的制备方法 |
| CN102633698A (zh) * | 2012-04-28 | 2012-08-15 | 重庆紫光天化蛋氨酸有限责任公司 | 甲硫醇和丙烯醛合成的粗甲硫基代丙醛的处理方法和系统 |
| CN102633698B (zh) * | 2012-04-28 | 2014-07-30 | 重庆紫光天化蛋氨酸有限责任公司 | 甲硫醇和丙烯醛合成的粗甲硫基代丙醛的处理方法和系统 |
| CN105136942A (zh) * | 2015-08-27 | 2015-12-09 | 天津春发生物科技集团有限公司 | 一种2,3-二甲基吡嗪的分析检测方法 |
| CN109160893A (zh) * | 2018-10-15 | 2019-01-08 | 禄丰天宝磷化工有限公司 | 一种甲硒基丙醛的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996001810A1 (en) | 1996-01-25 |
| JPH10504812A (ja) | 1998-05-12 |
| EP0770062A1 (en) | 1997-05-02 |
| AU699841B2 (en) | 1998-12-17 |
| RU2149159C1 (ru) | 2000-05-20 |
| TW296373B (enrdf_load_stackoverflow) | 1997-01-21 |
| PL318213A1 (en) | 1997-05-26 |
| AU3093995A (en) | 1996-02-09 |
| KR970704681A (ko) | 1997-09-06 |
| EP0770062A4 (en) | 1999-02-10 |
| MX9700276A (es) | 1997-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1313429C (zh) | 制备丙烯酸的方法 | |
| CN1089082C (zh) | 制备环己烷二甲醇的方法 | |
| CN1046494C (zh) | 芳烃的制备方法 | |
| CN1247515C (zh) | （甲基）丙烯酸类的制造方法 | |
| CN1173906C (zh) | 制备表氯醇及其中间体的方法 | |
| CN1681569A (zh) | 液压密封错流传质塔板 | |
| CN1823032A (zh) | 用于分离至少一股含富集的(甲基)丙烯酸单体的料流的热分离方法 | |
| CN1075486C (zh) | 碳酸二甲酯制备方法 | |
| CN1094925C (zh) | 制备2－羟基－4－甲基硫代丁酸或其盐的连续水解法 | |
| CN1550486A (zh) | 停止蒸馏塔运转的方法 | |
| CN1263725C (zh) | （甲基）丙烯酸的精制方法 | |
| CN1025561C (zh) | 生产丙烯酸酯的方法 | |
| CN1090616C (zh) | 具有储存稳定性的2－羟基－4－甲基硫代丁酸(mha)的制备方法 | |
| CN1152913A (zh) | 制备3-(甲硫基)丙醛的方法 | |
| CN1046260C (zh) | 具备高伯羟基含量的二醇 | |
| CN1312788A (zh) | 由丙烷制备丙烯醛和/或丙烯酸的方法 | |
| CN1717269A (zh) | 由对应的羧酸酯水解制造羧酸和醇的方法及装置 | |
| CN1590360A (zh) | 制备（甲基）丙烯酸化合物的方法 | |
| CN1273461C (zh) | 路易斯酸催化剂组合物 | |
| CN1070838C (zh) | 控制雾化液体中转化率和温度制造中间氧化产物的方法和设备 | |
| CN1491928A (zh) | 二甲醚制造用催化剂及其制造方法以及二甲醚的制造方法 | |
| CN1839170A (zh) | 芳香族聚碳酸酯的制造方法 | |
| CN1061969C (zh) | 工业级枯烯过氧化氢酸性裂解生产苯酚、丙酮和α-甲基苯乙烯的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |