AU606150B2 - Alkoxylation process using calcium based catalysts - Google Patents
Alkoxylation process using calcium based catalysts Download PDFInfo
- Publication number
- AU606150B2 AU606150B2 AU15197/88A AU1519788A AU606150B2 AU 606150 B2 AU606150 B2 AU 606150B2 AU 15197/88 A AU15197/88 A AU 15197/88A AU 1519788 A AU1519788 A AU 1519788A AU 606150 B2 AU606150 B2 AU 606150B2
- Authority
- AU
- Australia
- Prior art keywords
- alcohol
- catalyst
- calcium
- mix
- alkoxide
- 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.)
- Ceased
Links
- 239000003054 catalyst Substances 0.000 title claims description 107
- 238000000034 method Methods 0.000 title claims description 51
- 230000008569 process Effects 0.000 title claims description 46
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims description 30
- 239000011575 calcium Substances 0.000 title claims description 30
- 229910052791 calcium Inorganic materials 0.000 title claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 89
- 229910052782 aluminium Inorganic materials 0.000 claims description 72
- -1 aluminium alkoxide Chemical class 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 49
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims description 33
- 230000000694 effects Effects 0.000 claims description 28
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 26
- 239000004411 aluminium Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 150000007522 mineralic acids Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 239000001117 sulphuric acid Substances 0.000 claims description 16
- 235000011149 sulphuric acid Nutrition 0.000 claims description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000004703 alkoxides Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 8
- 239000000920 calcium hydroxide Substances 0.000 claims description 8
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 8
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000292 calcium oxide Substances 0.000 claims description 8
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000007046 ethoxylation reaction Methods 0.000 description 22
- 150000001298 alcohols Chemical class 0.000 description 17
- 229940043430 calcium compound Drugs 0.000 description 15
- 150000001674 calcium compounds Chemical class 0.000 description 15
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 11
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000032683 aging Effects 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 238000009826 distribution Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002483 hydrogen compounds Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- BEGNRPGEHZBNKK-UHFFFAOYSA-N 2-methylnonan-1-ol Chemical compound CCCCCCCC(C)CO BEGNRPGEHZBNKK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- ZVHAANQOQZVVFD-UHFFFAOYSA-N 5-methylhexan-1-ol Chemical compound CC(C)CCCCO ZVHAANQOQZVVFD-UHFFFAOYSA-N 0.000 description 1
- MIMUSZHMZBJBPO-UHFFFAOYSA-N 6-methoxy-8-nitroquinoline Chemical compound N1=CC=CC2=CC(OC)=CC([N+]([O-])=O)=C21 MIMUSZHMZBJBPO-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 101100533757 Caenorhabditis elegans snf-3 gene Proteins 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JIMMILCKVYOFET-UHFFFAOYSA-N hexadecan-4-ol Chemical compound CCCCCCCCCCCCC(O)CCC JIMMILCKVYOFET-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006353 oxyethylene group Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- HRDGAIGDKJXHIU-UHFFFAOYSA-N tetradecan-4-ol Chemical compound CCCCCCCCCCC(O)CCC HRDGAIGDKJXHIU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US043660 | 1987-04-28 | ||
| US07/043,660 US4775653A (en) | 1987-04-28 | 1987-04-28 | Alkoxylation process using calcium based catalysts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1519788A AU1519788A (en) | 1988-11-03 |
| AU606150B2 true AU606150B2 (en) | 1991-01-31 |
Family
ID=21928237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU15197/88A Ceased AU606150B2 (en) | 1987-04-28 | 1988-04-27 | Alkoxylation process using calcium based catalysts |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4775653A (en, 2012) |
| EP (1) | EP0289159B1 (en, 2012) |
| JP (2) | JPS63283757A (en, 2012) |
| KR (1) | KR910004076B1 (en, 2012) |
| CN (1) | CN1022990C (en, 2012) |
| AU (1) | AU606150B2 (en, 2012) |
| BR (1) | BR8802060A (en, 2012) |
| CA (1) | CA1291148C (en, 2012) |
| DE (1) | DE3876673T2 (en, 2012) |
| DK (1) | DK171557B1 (en, 2012) |
| IE (1) | IE65368B1 (en, 2012) |
| IN (1) | IN169732B (en, 2012) |
| MX (1) | MX169595B (en, 2012) |
| MY (1) | MY102324A (en, 2012) |
| NO (1) | NO180327C (en, 2012) |
| PH (1) | PH24082A (en, 2012) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721817A (en) * | 1986-12-31 | 1988-01-26 | Shell Oil Company | Preparation of nonionic surfactants |
| US5104575A (en) * | 1987-09-30 | 1992-04-14 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation using heterogeneous calcium catalysts and products therefrom |
| US5120697A (en) * | 1988-09-30 | 1992-06-09 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation using modified calcium-containing catalysts |
| US5112789A (en) * | 1988-09-30 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation catalysis |
| US5114900A (en) * | 1988-09-30 | 1992-05-19 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation using modified calcium-containing bimetallic or polymetallic catalysts |
| US5112788A (en) * | 1988-09-30 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation using modified group iia metal-containing bimetallic or polymetallic catalysts |
| US5118650A (en) * | 1988-09-30 | 1992-06-02 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation using modified group iiib metal-containing bimetallic or polymetallic catalysts |
| US4946984A (en) * | 1988-09-30 | 1990-08-07 | Union Carbide Chemicals And Plastics Company Inc. | Alkoxylation using a calcium sulfate catalyst |
| GB8904415D0 (en) * | 1989-02-27 | 1989-04-12 | Unilever Plc | Liquid detergent products |
| EP0429728B1 (en) * | 1989-11-30 | 1994-06-15 | International Business Machines Corporation | Logic circuit |
| US5191104A (en) * | 1990-09-20 | 1993-03-02 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation of carboxylated compounds |
| US5104987A (en) * | 1990-09-20 | 1992-04-14 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation of active hydrogen-containing compounds |
| US5386045A (en) * | 1991-08-22 | 1995-01-31 | Vista Chemical Company | Process for alkoxylation of esters and products produced therefrom |
| US5220077A (en) * | 1992-08-19 | 1993-06-15 | Vista Chemical Company | Alkoxylation process |
| US5352842A (en) * | 1993-03-30 | 1994-10-04 | Vista Chemical Company | Process for clarifying alkoxylated alcohols |
| US5627121A (en) * | 1995-06-15 | 1997-05-06 | Condea Vista Company | Process for preparing alkoxylation catalysts and alkoxylation process |
| US6057280A (en) | 1998-11-19 | 2000-05-02 | Huish Detergents, Inc. | Compositions containing α-sulfofatty acid esters and methods of making and using the same |
| US6235300B1 (en) | 1999-01-19 | 2001-05-22 | Amway Corporation | Plant protecting adjuvant containing topped or peaked alcohol alkoxylates and conventional alcohol alkoxylates |
| US6147246A (en) * | 1999-12-23 | 2000-11-14 | Condea Vista Company | Process for preparing alkoxylated dialkyl carbonate compounds |
| US6593500B2 (en) | 2001-01-19 | 2003-07-15 | Rhodia, Inc. | Process for alkoxylation with a boron-containing catalyst |
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| US3244646A (en) * | 1962-01-04 | 1966-04-05 | Socony Mobil Oil Co Inc | Polymerization of epoxides using as catalyst a metal alkoxide-phosphorous acid reaction product |
| CA1187105A (en) * | 1979-09-27 | 1985-05-14 | James H. Mccain, Jr. | Process for preparation of catalysts for oxyalkylation of reactive hydrogen compounds |
| EP0085167A1 (en) * | 1981-12-24 | 1983-08-10 | Conoco Phillips Company | Alkoxylation with calcium and magnesium salts |
| US4456697A (en) * | 1982-09-23 | 1984-06-26 | Conoco Inc. | Catalysts for alkoxylation reactions |
| AU570489B2 (en) * | 1983-07-05 | 1988-03-17 | Union Carbide Corporation | Alkoxylation using calcium catalysts |
-
1987
- 1987-04-28 US US07/043,660 patent/US4775653A/en not_active Expired - Lifetime
-
1988
- 1988-03-29 IN IN260/CAL/88A patent/IN169732B/en unknown
- 1988-04-07 IE IE103988A patent/IE65368B1/en not_active IP Right Cessation
- 1988-04-08 MY MYPI88000358A patent/MY102324A/en unknown
- 1988-04-11 DE DE8888303226T patent/DE3876673T2/de not_active Expired - Lifetime
- 1988-04-11 EP EP88303226A patent/EP0289159B1/en not_active Expired - Lifetime
- 1988-04-12 PH PH36783A patent/PH24082A/en unknown
- 1988-04-12 DK DK199488A patent/DK171557B1/da active IP Right Grant
- 1988-04-20 MX MX011178A patent/MX169595B/es unknown
- 1988-04-25 CA CA000564997A patent/CA1291148C/en not_active Expired - Lifetime
- 1988-04-26 JP JP63101493A patent/JPS63283757A/ja active Granted
- 1988-04-26 NO NO881818A patent/NO180327C/no not_active IP Right Cessation
- 1988-04-27 AU AU15197/88A patent/AU606150B2/en not_active Ceased
- 1988-04-28 KR KR1019880004856A patent/KR910004076B1/ko not_active Expired
- 1988-04-28 BR BR8802060A patent/BR8802060A/pt not_active IP Right Cessation
- 1988-04-28 CN CN88102512A patent/CN1022990C/zh not_active Expired - Lifetime
-
1993
- 1993-05-10 JP JP5131051A patent/JP2572523B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK199488A (da) | 1988-10-29 |
| JPS63283757A (ja) | 1988-11-21 |
| NO180327B (no) | 1996-12-23 |
| KR910004076B1 (ko) | 1991-06-22 |
| IE65368B1 (en) | 1995-10-18 |
| JPH0577456B2 (en, 2012) | 1993-10-26 |
| AU1519788A (en) | 1988-11-03 |
| MY102324A (en) | 1992-05-28 |
| EP0289159A3 (en) | 1989-07-05 |
| PH24082A (en) | 1990-03-05 |
| NO881818D0 (no) | 1988-04-26 |
| DK199488D0 (da) | 1988-04-12 |
| CN88102512A (zh) | 1988-11-23 |
| EP0289159A2 (en) | 1988-11-02 |
| BR8802060A (pt) | 1988-11-29 |
| CA1291148C (en) | 1991-10-22 |
| JP2572523B2 (ja) | 1997-01-16 |
| IN169732B (en, 2012) | 1991-12-14 |
| NO180327C (no) | 1997-04-02 |
| IE881039L (en) | 1988-10-28 |
| DE3876673T2 (de) | 1993-07-01 |
| US4775653A (en) | 1988-10-04 |
| JPH0686936A (ja) | 1994-03-29 |
| DK171557B1 (da) | 1997-01-13 |
| CN1022990C (zh) | 1993-12-08 |
| KR880012269A (ko) | 1988-11-26 |
| DE3876673D1 (de) | 1993-01-28 |
| NO881818L (no) | 1988-10-31 |
| EP0289159B1 (en) | 1992-12-16 |
| MX169595B (es) | 1993-07-14 |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |