GB1114379A - Alkanol mixtures and ester thereof - Google Patents
Alkanol mixtures and ester thereofInfo
- Publication number
- GB1114379A GB1114379A GB54823/65A GB5482365A GB1114379A GB 1114379 A GB1114379 A GB 1114379A GB 54823/65 A GB54823/65 A GB 54823/65A GB 5482365 A GB5482365 A GB 5482365A GB 1114379 A GB1114379 A GB 1114379A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isomeric
- mixtures
- mixture
- hydroformylation
- mono
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title abstract 12
- 150000002148 esters Chemical class 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 238000007037 hydroformylation reaction Methods 0.000 abstract 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- 150000001279 adipic acids Chemical class 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 2
- 150000001536 azelaic acids Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 abstract 2
- 150000003022 phthalic acids Chemical class 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 150000003330 sebacic acids Chemical class 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000005498 phthalate group Chemical class 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 abstract 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
- C07C29/14—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 a —CHO group
- C07C29/141—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 a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/42—Platinum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/75—Cobalt
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
- C07C2531/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of the platinum group metals, iron group metals or copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Plasticizers for polyvinylchloride comprise the esters of dicarboxylic acids with an isomeric mixture of straight and mono-branched chain alkanols containing 7, 9 or 11 carbon atoms, said mixture having been made by hydroformylation of the C6, C8 or C10 olefines, obtained by aluminium trialkyl catalyzed polymerization of ethylene, followed by reduction of the resulting isomeric mixture of aldehydes. Specified acids are phthalic, adipic, sebacic and azelaic acids. Compositions comprising 100 pts P.V.C. and 50 pts by weight of the isomeric diheptanyldinonanyl- and diundecanyl phthalates are specified.ALSO:Isomeric mixtures of straight- and mono-branched chain alkanols containing 7, 9 or 11 carbon atoms are made by polymerization of ethylene using an aluminium trialkyl catalyst, fractionating the product to give isomeric mixtures of straight and mono-branched chain a -olefines containing 6, 8 or 10 carbon atoms, subjecting each mixture to hydroformylation using carbon monoxide and hydrogen with an Oxo catalyst and reducing the resulting isomeric mixture of C7, C9 or C11 alkanols. On esterification, by known methods, with a dicarboxylic acid, e.g. phthalic, adipic, sebacic or azelaic acids, the alkanol mixtures yield isomeric ester mixtures which are used as plasticizers (see Division C3). The hydroformylation is effected under conventional conditions. The aldehyde reduction step can be achieved by using a reducing agent, e.g. sodium borohydride, or, preferably, by using catalytic hydrogenation. Examples relate to the preparation of isomeric mixtures of heptanol, nonanol and undecanol and to the esterification thereof using phthalic anhydride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42202464A | 1964-12-29 | 1964-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1114379A true GB1114379A (en) | 1968-05-22 |
Family
ID=23673074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54823/65A Expired GB1114379A (en) | 1964-12-29 | 1965-12-24 | Alkanol mixtures and ester thereof |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1464291A (en) |
| GB (1) | GB1114379A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2855421A1 (en) * | 1977-12-23 | 1979-07-05 | Nissan Chemical Ind Ltd | PLASTICIZERS |
| US6437170B1 (en) | 1999-04-21 | 2002-08-20 | Basf Aktiengesellschaft | Mixture of diesters of adipic or phthalic acid with isomers of nonanols |
| US7667080B2 (en) | 2004-08-04 | 2010-02-23 | Exxonmobil Chemical Patents Inc. | Mixtures of C8-C10 alcohols |
| JP2019059885A (en) * | 2017-09-28 | 2019-04-18 | 新日本理化株式会社 | Plasticizer for vinyl chloride resin containing aliphatic dibasic acid diester |
-
1965
- 1965-12-24 GB GB54823/65A patent/GB1114379A/en not_active Expired
- 1965-12-29 FR FR44112A patent/FR1464291A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2855421A1 (en) * | 1977-12-23 | 1979-07-05 | Nissan Chemical Ind Ltd | PLASTICIZERS |
| US6437170B1 (en) | 1999-04-21 | 2002-08-20 | Basf Aktiengesellschaft | Mixture of diesters of adipic or phthalic acid with isomers of nonanols |
| JP2002542217A (en) * | 1999-04-21 | 2002-12-10 | ビーエーエスエフ アクチェンゲゼルシャフト | Mixture of diesters of adipic or phthalic acid and the isomer nonanol |
| US7667080B2 (en) | 2004-08-04 | 2010-02-23 | Exxonmobil Chemical Patents Inc. | Mixtures of C8-C10 alcohols |
| JP2019059885A (en) * | 2017-09-28 | 2019-04-18 | 新日本理化株式会社 | Plasticizer for vinyl chloride resin containing aliphatic dibasic acid diester |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1464291A (en) | 1966-12-30 |
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