GB1025054A - Process for the preparation of 2,2-dimethylalkanoic acid esters - Google Patents
Process for the preparation of 2,2-dimethylalkanoic acid estersInfo
- Publication number
- GB1025054A GB1025054A GB37255/62A GB3725562A GB1025054A GB 1025054 A GB1025054 A GB 1025054A GB 37255/62 A GB37255/62 A GB 37255/62A GB 3725562 A GB3725562 A GB 3725562A GB 1025054 A GB1025054 A GB 1025054A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- butyl
- formula
- acid
- dimethyl
- 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
- 150000002148 esters Chemical class 0.000 title abstract 8
- 239000002253 acid Substances 0.000 title abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002510 isobutyric acid esters Chemical class 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 abstract 1
- VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 abstract 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract 1
- QSOGLNCCKWUXRN-CIGKAFDASA-N [(2r,3r,4s,5r,6r)-6-[(2s,3s,4r,5r)-3,4-bis(2-methylpropanoyloxy)-2,5-bis(2-methylpropanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]methyl 2-methylpropanoate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(=O)C(C)C)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O1 QSOGLNCCKWUXRN-CIGKAFDASA-N 0.000 abstract 1
- VGZOEDUWOQJGDE-UHFFFAOYSA-N [Cu+2].[Ba+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O Chemical compound [Cu+2].[Ba+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O VGZOEDUWOQJGDE-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical class CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 1
- 238000010586 diagram Methods 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229940035429 isobutyl alcohol Drugs 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- -1 isobutyroxytrimethylhexyl isobutyroxy Chemical group 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- 229940117969 neopentyl glycol Drugs 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 abstract 1
- 235000010983 sucrose acetate isobutyrate Nutrition 0.000 abstract 1
- 239000001797 sucrose acetate isobutyrate Substances 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 150000005691 triesters Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- 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
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—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
- C07C69/24—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 monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of 2,2-dimethylalkanoic acid are prepared by contacting an isobutyric acid ester with a terminal olefinic monomer of formula CH2=CR1R2, where R1 and R2 are hydrogen atoms or alkyl groups in the presence of a telomerization catalyst at a pressure of 400 to 3000 p.s.i.g. and a temperature of 50 DEG to 400 DEG C. The isobutyric ester may have the formula ROOCCH(CH3)2, where R is alkyl, cycloalkyl, aralkyl, acyloxyalkyl, hydroxyalkyl or acyl radical, and the telomer ester <FORM:1025054/C2/1> where n is an integer from 1 to 16. Esters of formula <FORM:1025054/C2/2> in which R is alkyl, cycloalkyl, aralkyl, or aryl and m is an integer from 2 to 16, and of formula <FORM:1025054/C2/3> where m is 2-16 are claimed. Examples of R are methyl, ethyl, propyl, isopropyl, isobutyl, butyl, sec.-butyl, tert.-butyl, anyl, isoamyl, cyclohexyl, phenyl, tolyl, and benzyl radicals. Isobutyric acid esters include mono-, di- and tri-esters with trimethylpentanediol, neopentyl-glycol, trimethylolpropane and esters such as sucrose acetate isobutyrate, sucrose octaisobutyrate, isobutyroxytrimethylhexyl isobutyroxy trimethyldexoate. Ethylene and propylene are preferred and catalysts are peroxides; or Lewis acids specified are hydrogen, acetyl, benzoyl, butyl, lauroyl, propyl, diethyl, dimethyl, dicumyl, or di-t-butyl peroxides, hydrazine salts, cumene hydroperoxide, perhalo compounds, oxygen, and hypohalites. The reaction may be batchwise or continuous and a reaction system is described with the aid of a circuit diagram. The ester products may be subjected to acidolysis by heating with isobutyric acid and an acid catalysts, or alcoholysis by heating with isobutyl alcohol and an alkali metal alcoholate to produce 2,2-dimethyl alkanoic acid and alkanol respectively, or alternatively the esters are hydrogenated in the presence of a catalyst such as copper chromite, Raney nickel, platinum and palladium and particularly barium copper chromite, to produce 2,2-dimethyl alkanols; or thermally cracked preferably between 400 DEG and 700 DEG C. in the presence of catalysts such as silica-alumina, silica-zirconia, and silica-magnesia to produce 2,2-dimethyl alkanoic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14463461A | 1961-10-12 | 1961-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1025054A true GB1025054A (en) | 1966-04-06 |
Family
ID=22509449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37255/62A Expired GB1025054A (en) | 1961-10-12 | 1962-10-02 | Process for the preparation of 2,2-dimethylalkanoic acid esters |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1443774A1 (en) |
| GB (1) | GB1025054A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD328174S (en) | 1989-10-19 | 1992-07-21 | D.W. Watkins Ltd. | Waste disposal chute or similar article |
| US5472768A (en) * | 1993-03-18 | 1995-12-05 | Anson; Andrew P. | Tubular section rolled up from a flexible sheet |
-
1962
- 1962-09-27 DE DE19621443774 patent/DE1443774A1/en active Pending
- 1962-10-02 GB GB37255/62A patent/GB1025054A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD328174S (en) | 1989-10-19 | 1992-07-21 | D.W. Watkins Ltd. | Waste disposal chute or similar article |
| US5472768A (en) * | 1993-03-18 | 1995-12-05 | Anson; Andrew P. | Tubular section rolled up from a flexible sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1443774A1 (en) | 1968-11-28 |
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