CN1938252A - 制备1,3-二氯丙酮的方法 - Google Patents
制备1,3-二氯丙酮的方法 Download PDFInfo
- Publication number
- CN1938252A CN1938252A CN200580010765.2A CN200580010765A CN1938252A CN 1938252 A CN1938252 A CN 1938252A CN 200580010765 A CN200580010765 A CN 200580010765A CN 1938252 A CN1938252 A CN 1938252A
- Authority
- CN
- China
- Prior art keywords
- acetone
- produce
- dichloro
- catalyzer
- mca
- 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.)
- Granted
Links
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 claims abstract description 43
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000007323 disproportionation reaction Methods 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000003057 platinum Chemical class 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 9
- 230000007062 hydrolysis Effects 0.000 abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 5
- -1 alkali metal salt Chemical class 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000010499 C–H functionalization reaction Methods 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035899 viability Effects 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
- C07C29/136—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 of >C=O containing groups, e.g. —COOH
- C07C29/143—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 of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—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 of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
Abstract
Description
催化剂 | 摩尔cat./摩尔MCA | 摩尔Cl/摩尔MCA | 摩尔H2O/摩尔MCA | 剩余的MCA面积百分比 | 1,3-DCA面积百分比 | 1,1,3-TCA面积百分比 | 1,1-DCA面积百分比 | 丙酮面积百分比 |
HHCP(aq)* | 0.0021 | 0.013 | 0.57 | 81 | 6.4 | 0.01 | 2.36 | 8 |
PtCl2 | 0.0025 | 0.0051 | 0.17 | 61 | 11.3 | 0.06 | 2.22 | 10.1 |
PtO2 | 0.0025 | 0 | 0.15 | 65 | 11.3 | 0.05 | 2.24 | 9.3 |
PtCl2/H2Pt(OH)6** | 0.0026 | 0.0046 | 0.06 | 59 | 10.0 | 0.05 | 2.34 | 7.96 |
Pt粉 | 0.0030 | 0.0093 | 0.15 | 94 | 0.27 | 0.00 | 2.03 | 1.71 |
CoCl2 | 0.0027 | 0.0054 | 0.15 | 94 | 0.27 | 0.01 | 2.06 | 1.77 |
CuCl2 | 0.0026 | 0.0051 | 0.16 | 92 | 0.28 | 0.00 | 2.05 | 1.77 |
CuCl2(重复) | 0.0026 | 0.0053 | 0.14 | 95 | 0.28 | 0.00 | 2.05 | 1.06 |
CuCl | 0.0027 | 0.0055 | 0.16 | 94 | 0.28 | 0.00 | 1.97 | 1.69 |
FeCl3 | 0.0024 | 0.0047 | 0.16 | 94 | 0.27 | 0.01 | 2.03 | 1.99 |
HgCl2 | 0.0024 | 0.0047 | 0.15 | 94 | 0.27 | 0.01 | 2.03 | 1.94 |
IrCl3 | 0.0024 | 0.0047 | 0.14 | 95 | 0.26 | 0.00 | 2.01 | 0.50 |
IrCl4 | 0.0025 | 0.0050 | 0.14 | 94 | 0.26 | 0.01 | 2.05 | 1.76 |
PdCl2 | 0.0024 | 0.0047 | 0.17 | 94 | 0.27 | 0.01 | 2.03 | 1.93 |
RuCl2 | 0.0023 | 0.0047 | 0.14 | 95 | 0.26 | 0.00 | 1.85 | 1.73 |
RhCl2 | 0.0022 | 0.0045 | 0.17 | 94 | 0.27 | 0.02 | 2.03 | 1.67 |
TiCl3 | 0.0029 | 0.0057 | 0.15 | 94 | 0.27 | 0.01 | 2.03 | 1.83 |
TiCl | 0.0026 | 0.0052 | 0.16 | 95 | 0.26 | 0.00 | 2.02 | 0.72 |
ZrCl4 | 0.0030 | 0.0061 | 0.13 | 71 | 0.35 | 0 | 3.09 | 2.62 |
仅MCA | NA | NA | NA | 95 | 0.17 | 0.00 | 2.28 | 0 |
时间(小时) | 摩尔Pt/摩尔MCA | 摩尔Cl/摩尔MCA | 摩尔H2O/摩尔MCA | 剩余的MCA面积百分比 | 1,3-DCA面积百分比 | 1,1,3-TCA面积百分比 | 1,1-DCA面积百分比 | |
PtO2(没有HCl) | 6.5 | 0.0027 | 0 | 0.15 | 92 | 1.0 | 0.01 | 2.05 |
PtO2(米用HCl) | 6.5 | 0.0027 | 0.0076 | 0.29 | 79 | 7.8 | 0.02 | 2.07 |
PtO2(没有HCl) | ~22.5 | - | 0 | - | 60 | 11.2 | 0.05 | 2.31 |
PtO2(米用HCl)仅MCA | ~22.5NA | -NA | 0.0076NA | -NA | 6595 | 11.30.17 | 0.050 | 2.242.28 |
酸 | 摩尔Pt/摩尔MCA | 摩尔Cl/摩尔MCA | 摩尔H2O/摩尔MCA | 剩余的MCA面积百分比 | 1,3-DCA面积百分比 | 1,1,3-TCA面积百分比 | 1,1-DCA面积百分比 |
HCl | 0.0023 | 0.029 | 0.468 | 73 | 10 | 0.04 | 2.32 |
H2SO4 | 0.0026 | 0 | 0.549 | 90 | 2 | 0.02 | 1.99 |
p-TSA水合物* | 0.0025 | 0 | 0.457 | 80 | 3 | 0.01 | 2.37 |
仅MCA | NA | NA | NA | 95 | 0.17 | 0 | 2.28 |
摩尔p-TSA*/摩 尔MCA | 摩尔Cl/摩尔MCA | 摩尔H2O/摩尔MCA | 剩余的MCA面积百分比 | 1,3-DCA面积百分比 | 1,1,3-TCA面积百分比 | 1,1-DCA面积百分比 | |
仅MCA | NA | NA | NA | 95 | 0.17 | 0.00 | 2.28 |
LiCl(干燥) | 0 | 0.228 | 0 | 85 | 5 | 0.03 | 2.15 |
LiCl+水 | 0 | 0.156 | 0.450 | 84 | 6 | 0.02 | 2.11 |
LiCl+p-TSA | 0.051 | 0.255 | 0.102 | 63 | 15 | 0.11 | 2.28 |
仅p-TSA | 0.052 | 0 | 0.104 | 63 | 0.22 | 0.02 | 3.18 |
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US55821404P | 2004-03-31 | 2004-03-31 | |
US60/558,214 | 2004-03-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1938252A true CN1938252A (zh) | 2007-03-28 |
CN100494147C CN100494147C (zh) | 2009-06-03 |
Family
ID=34963647
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200580010765.2A Expired - Fee Related CN100494147C (zh) | 2004-03-31 | 2005-03-24 | 制备1,3-二氯丙酮的方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US7361790B2 (zh) |
EP (1) | EP1732873B1 (zh) |
JP (1) | JP4638482B2 (zh) |
CN (1) | CN100494147C (zh) |
AT (1) | ATE467612T1 (zh) |
CA (1) | CA2559522A1 (zh) |
DE (1) | DE602005021209D1 (zh) |
WO (1) | WO2005097722A1 (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2053034B1 (en) | 2003-11-20 | 2018-01-24 | Solvay Sa | Process for producing a chlorohydrin |
US20100032617A1 (en) | 2007-02-20 | 2010-02-11 | Solvay (Societe Anonyme) | Process for manufacturing epichlorohydrin |
CN103261181A (zh) | 2010-09-30 | 2013-08-21 | 索尔维公司 | 天然来源的环氧氯丙烷的衍生物 |
EP2669305A1 (en) | 2012-06-01 | 2013-12-04 | Solvay Sa | Process for manufacturing an epoxy resin |
EP2669307A1 (en) | 2012-06-01 | 2013-12-04 | Solvay Sa | Process for manufacturing an epoxide |
EP2669306B1 (en) | 2012-06-01 | 2015-08-12 | Solvay Sa | Process for manufacturing an epoxy resin |
EP2669247A1 (en) | 2012-06-01 | 2013-12-04 | Solvay Sa | Process for manufacturing dichloropropanol |
EP2669308A1 (en) | 2012-06-01 | 2013-12-04 | Solvay Sa | Process for manufacturing an epoxy resin |
WO2015074684A1 (en) | 2013-11-20 | 2015-05-28 | Solvay Sa | Process for manufacturing an epoxy resin |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2860146A (en) * | 1955-04-14 | 1958-11-11 | Shell Dev | Manufacture of epihalohydrins |
US3397240A (en) * | 1962-07-24 | 1968-08-13 | Merck & Co Inc | Process for the monohalogenation of acetone |
US4251467A (en) * | 1976-09-02 | 1981-02-17 | Chevron Research Company | Continuous preparation of chloroacetone |
US4439623A (en) * | 1981-10-05 | 1984-03-27 | Merck & Co., Inc. | Process for the preparation of monochloroacetone |
US5744655A (en) * | 1996-06-19 | 1998-04-28 | The Dow Chemical Company | Process to make 2,3-dihalopropanols |
AU2709900A (en) * | 1998-12-18 | 2000-07-03 | Dow Chemical Company, The | Process for making 2,3-dihalopropanols |
US6262280B1 (en) * | 1999-01-20 | 2001-07-17 | E. I. Du Pont De Nemours And Company | Shilov-type reactions |
US20040030199A1 (en) * | 2002-01-29 | 2004-02-12 | Maughon Robert R. | Process for reducing alpha-haloketones to secondary alpha-haloalcohols |
-
2005
- 2005-03-24 DE DE602005021209T patent/DE602005021209D1/de active Active
- 2005-03-24 EP EP05729166A patent/EP1732873B1/en not_active Not-in-force
- 2005-03-24 AT AT05729166T patent/ATE467612T1/de not_active IP Right Cessation
- 2005-03-24 CA CA002559522A patent/CA2559522A1/en not_active Abandoned
- 2005-03-24 US US10/588,623 patent/US7361790B2/en not_active Expired - Fee Related
- 2005-03-24 JP JP2007506260A patent/JP4638482B2/ja not_active Expired - Fee Related
- 2005-03-24 CN CN200580010765.2A patent/CN100494147C/zh not_active Expired - Fee Related
- 2005-03-24 WO PCT/US2005/009767 patent/WO2005097722A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
EP1732873B1 (en) | 2010-05-12 |
DE602005021209D1 (de) | 2010-06-24 |
JP2007530686A (ja) | 2007-11-01 |
ATE467612T1 (de) | 2010-05-15 |
WO2005097722A1 (en) | 2005-10-20 |
CA2559522A1 (en) | 2005-10-20 |
US7361790B2 (en) | 2008-04-22 |
JP4638482B2 (ja) | 2011-02-23 |
US20070129556A1 (en) | 2007-06-07 |
EP1732873A1 (en) | 2006-12-20 |
CN100494147C (zh) | 2009-06-03 |
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