GB815991A - Dibenzoate esters of aliphatic diols and process for their preparation - Google Patents
Dibenzoate esters of aliphatic diols and process for their preparationInfo
- Publication number
- GB815991A GB815991A GB5966/56A GB596656A GB815991A GB 815991 A GB815991 A GB 815991A GB 5966/56 A GB5966/56 A GB 5966/56A GB 596656 A GB596656 A GB 596656A GB 815991 A GB815991 A GB 815991A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- methyl
- pentanediol
- fraction
- butyl benzoate
- 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
- -1 aliphatic diols Chemical class 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 5
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 abstract 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002009 diols Chemical class 0.000 abstract 2
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 abstract 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000292 calcium oxide Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises a process for preparing dibenzoate esters of aliphatic diols wherein butyl benzoate is reacted with an aliphatic diol having 4 to 9 carbon atoms and no "tertiary hydroxyl groups," and also the dibenzoate esters of 2 - ethyl - 1 : 3 - hexanediol, 2 - methyl- or -ethyl - 1 : 5 - pentanediol, 2 - ethyl - 3 - methyl-or 2 : 4-diethyl-1 : 5-pentanediol and 2-ethyl-2-butyl- or 2-methyl-2-propyl-1 : 3-propanediol. A "tertiary hydroxyl group" is one which is attached to a tertiary carbon atom. Preferably, 1 mol. of the aliphatic diol is reacted with 2.5 mols. of butyl benzoate in the presence of an alkaline catalyst at a temperature of 100 DEG to 250 DEG C. and at a pressure from 0.1 mm. to 200 mm. Hg. Suitable catalysts are the alkali and alkaline earth metal oxides, hydroxides, alkoxides, carbonates and borates. Diols specified in addition to those in examples are 1 : 5-pentanediol and 2 : 5-hexanediol. In an example, butyl benzoate, dipropylene glycol and calcium oxide are mixed in a reaction vessel fitted with a stirrer and fractionating column, distilled in vacuo to give a first fraction of butanol, a mid-fraction of butanol and butyl benzoate and a final fraction of butyl benzoate, the residue is filtered to remove catalyst, stripped, treated with a decolorizing agent and filtered to give dipropylene glycol dibenzoate. Alternatively, the ester may be obtained as a fourth fraction in the vacuum distillation. The dibenzoate esters of the following diols are prepared similarly: diethylene glycol, 2-ethyl-1 : 3-hexanediol, 2 - methoxymethyl - 2 : 4 - dimethyl - 1 : 5 - pentanediol, 2 : 4 - diethyl- or 2 - methyl - 3 - methyl - 1 : 5 - pentanediol, 2- or 3-methyl- or 2-ethyl-1 : 5-pentanediol and 2 - ethyl - 2 - butyl- or 2 : 2 - diethyl- or 2-methyl-2-propyl-1 : 3-propanediol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US815991XA | 1955-02-28 | 1955-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815991A true GB815991A (en) | 1959-07-08 |
Family
ID=22165158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5966/56A Expired GB815991A (en) | 1955-02-28 | 1956-02-27 | Dibenzoate esters of aliphatic diols and process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB815991A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627818A (en) * | 1969-01-31 | 1971-12-14 | Monsanto Res Corp | Branched diesters |
| US5153342A (en) * | 1989-09-05 | 1992-10-06 | Huls America Inc. | Stain-resistant plasticizer compositions and method of making same |
| US5271930A (en) * | 1991-11-20 | 1993-12-21 | Finetex, Inc. | Benzoate esters of polyalkoxylated block copolymers |
| US7030181B2 (en) | 2001-04-11 | 2006-04-18 | Eastman Chemical Company | Films prepared from plasticized polyesters |
| EP1478617A4 (en) * | 2002-02-07 | 2006-04-19 | China Petroleum & Chemical | Polyol ester compounds useful in preparation of a catalyst for olefins polymerization, process for preparing the same and use thereof |
| US7078557B2 (en) | 2002-09-29 | 2006-07-18 | Condensia Quimica S.A. | Compound of plasticizers for the water dispersability of resins |
| US7235623B2 (en) | 2003-11-26 | 2007-06-26 | Eastman Chemical Company | Polyester compositions for calendering |
| US7285587B2 (en) | 2002-12-20 | 2007-10-23 | Eastman Chemical Company | Flame retardant polyester compositions for calendering |
| US7354653B2 (en) | 2003-12-18 | 2008-04-08 | Eastman Chemical Company | High clarity films with improved thermal properties |
| US8071695B2 (en) | 2004-11-12 | 2011-12-06 | Eastman Chemical Company | Polyeste blends with improved stress whitening for film and sheet applications |
| US10077352B2 (en) | 2014-09-16 | 2018-09-18 | Eastman Chemical Company | Polymeric compositions with improved noise suppression |
-
1956
- 1956-02-27 GB GB5966/56A patent/GB815991A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627818A (en) * | 1969-01-31 | 1971-12-14 | Monsanto Res Corp | Branched diesters |
| US5153342A (en) * | 1989-09-05 | 1992-10-06 | Huls America Inc. | Stain-resistant plasticizer compositions and method of making same |
| US5271930A (en) * | 1991-11-20 | 1993-12-21 | Finetex, Inc. | Benzoate esters of polyalkoxylated block copolymers |
| US7030181B2 (en) | 2001-04-11 | 2006-04-18 | Eastman Chemical Company | Films prepared from plasticized polyesters |
| EP1478617A4 (en) * | 2002-02-07 | 2006-04-19 | China Petroleum & Chemical | Polyol ester compounds useful in preparation of a catalyst for olefins polymerization, process for preparing the same and use thereof |
| US7078557B2 (en) | 2002-09-29 | 2006-07-18 | Condensia Quimica S.A. | Compound of plasticizers for the water dispersability of resins |
| US7285587B2 (en) | 2002-12-20 | 2007-10-23 | Eastman Chemical Company | Flame retardant polyester compositions for calendering |
| US7235623B2 (en) | 2003-11-26 | 2007-06-26 | Eastman Chemical Company | Polyester compositions for calendering |
| US7354653B2 (en) | 2003-12-18 | 2008-04-08 | Eastman Chemical Company | High clarity films with improved thermal properties |
| US8071695B2 (en) | 2004-11-12 | 2011-12-06 | Eastman Chemical Company | Polyeste blends with improved stress whitening for film and sheet applications |
| US10077352B2 (en) | 2014-09-16 | 2018-09-18 | Eastman Chemical Company | Polymeric compositions with improved noise suppression |
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