GB1586671A - Manufacture of esters - Google Patents
Manufacture of esters Download PDFInfo
- Publication number
- GB1586671A GB1586671A GB15744/77A GB1574477A GB1586671A GB 1586671 A GB1586671 A GB 1586671A GB 15744/77 A GB15744/77 A GB 15744/77A GB 1574477 A GB1574477 A GB 1574477A GB 1586671 A GB1586671 A GB 1586671A
- Authority
- GB
- United Kingdom
- Prior art keywords
- parts
- catalyst
- preparation
- diol
- mixture
- 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 claims description 28
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 76
- 238000002360 preparation method Methods 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 38
- 230000008569 process Effects 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 29
- 150000002009 diols Chemical class 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000004494 ethyl ester group Chemical group 0.000 claims description 19
- 239000010936 titanium Substances 0.000 claims description 19
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- -1 polyol titanate Chemical class 0.000 claims description 9
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 claims description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 8
- 239000013522 chelant Substances 0.000 claims description 8
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 229910052719 titanium Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 125000005594 diketone group Chemical group 0.000 claims description 4
- QPTWKDNRYCGMJM-UHFFFAOYSA-N ethyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C(Cl)Cl)C1(C)C QPTWKDNRYCGMJM-UHFFFAOYSA-N 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 238000001256 steam distillation Methods 0.000 claims description 4
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000003208 petroleum Substances 0.000 description 15
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 15
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 5
- 229940093858 ethyl acetoacetate Drugs 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical group [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15744/77A GB1586671A (en) | 1977-04-15 | 1977-04-15 | Manufacture of esters |
| IT2304077A IT1075648B (it) | 1976-04-29 | 1977-04-29 | Scambiatore di calore |
| ZA00781292A ZA781292B (en) | 1977-04-15 | 1978-03-06 | Manufacture of esters |
| AU33940/78A AU519306B2 (en) | 1977-04-15 | 1978-03-08 | Manufacturing of esters |
| NZ186666A NZ186666A (en) | 1977-04-15 | 1978-03-10 | Manufacture of esters of m-phenoxybenzyl alcohol using a titanium containing catalyst |
| IT21367/78A IT1095480B (it) | 1977-04-15 | 1978-03-20 | Preparazione di esteri |
| DE19782812365 DE2812365A1 (de) | 1977-04-15 | 1978-03-21 | Verfahren zur herstellung von estern von m-phenoxybenzylalkohol und von alpha- cyano- und alpha-aethinylderivaten davon mit carbonsaeuren |
| NL7803569A NL7803569A (nl) | 1977-04-15 | 1978-04-04 | Werkwijze ter bereiding van ester van m-fenoxybenzylal- kohol. |
| BE186669A BE865821A (fr) | 1977-04-15 | 1978-04-07 | Preparation d'esters de l'alcool m-phenoxybenzylique |
| FR7810618A FR2387211A1 (fr) | 1977-04-15 | 1978-04-11 | Preparation d'esters de l'alcool m-phenoxybenzylique |
| JP4410178A JPS53130627A (en) | 1977-04-15 | 1978-04-14 | Process for preparing ester of mmphenoxybenzyl alcohol or alpha cyano and alphaaethynyl derivative thereof with carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15744/77A GB1586671A (en) | 1977-04-15 | 1977-04-15 | Manufacture of esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1586671A true GB1586671A (en) | 1981-03-25 |
Family
ID=10064725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15744/77A Expired GB1586671A (en) | 1976-04-29 | 1977-04-15 | Manufacture of esters |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS53130627A (fr) |
| AU (1) | AU519306B2 (fr) |
| BE (1) | BE865821A (fr) |
| DE (1) | DE2812365A1 (fr) |
| FR (1) | FR2387211A1 (fr) |
| GB (1) | GB1586671A (fr) |
| IT (1) | IT1095480B (fr) |
| NL (1) | NL7803569A (fr) |
| NZ (1) | NZ186666A (fr) |
| ZA (1) | ZA781292B (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016012538A1 (fr) | 2014-07-24 | 2016-01-28 | Graziano Vignali | Dérivé organique de titane et son procédé de préparation, encre contenant le dérivé et procédé d'impression numérique sur matériaux céramiques qui utilise l'encre |
| CN107876092A (zh) * | 2017-11-24 | 2018-04-06 | 华东理工大学 | 酯交换合成碳酸苯甲酯和碳酸二苯酯的高稳定性钛催化剂 |
| CN115724878A (zh) * | 2022-11-14 | 2023-03-03 | 广州绿腾新材料有限公司 | 二次钛螯合物的制备方法及其在有机硅密封胶中的应用 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2009178B (en) * | 1977-11-28 | 1982-02-24 | Ici Ltd | Manufacture of esters |
| CN1144778C (zh) | 1998-10-08 | 2004-04-07 | 住友化学工业株式会社 | 制备环丙烷羧酸酯的方法 |
| CN1183095C (zh) | 1999-06-16 | 2005-01-05 | 住友化学工业株式会社 | 环丙烷羧酸酯的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1142868B (de) * | 1960-08-23 | 1963-01-31 | Wachker Chemie G M B H | Verfahren zur diskontinuierlichen oder kontinuierlichen Herstellung von Carbonsaeureestern |
| FR1313549A (fr) * | 1961-02-04 | 1962-12-28 | Wacker Chemie Gmbh | Procédé de préparation d'esters |
| GB1571388A (en) * | 1976-04-15 | 1980-07-16 | Ici Ltd | Manufacture of esters |
-
1977
- 1977-04-15 GB GB15744/77A patent/GB1586671A/en not_active Expired
-
1978
- 1978-03-06 ZA ZA00781292A patent/ZA781292B/xx unknown
- 1978-03-08 AU AU33940/78A patent/AU519306B2/en not_active Expired
- 1978-03-10 NZ NZ186666A patent/NZ186666A/xx unknown
- 1978-03-20 IT IT21367/78A patent/IT1095480B/it active
- 1978-03-21 DE DE19782812365 patent/DE2812365A1/de not_active Withdrawn
- 1978-04-04 NL NL7803569A patent/NL7803569A/xx not_active Application Discontinuation
- 1978-04-07 BE BE186669A patent/BE865821A/fr not_active IP Right Cessation
- 1978-04-11 FR FR7810618A patent/FR2387211A1/fr active Granted
- 1978-04-14 JP JP4410178A patent/JPS53130627A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016012538A1 (fr) | 2014-07-24 | 2016-01-28 | Graziano Vignali | Dérivé organique de titane et son procédé de préparation, encre contenant le dérivé et procédé d'impression numérique sur matériaux céramiques qui utilise l'encre |
| CN107876092A (zh) * | 2017-11-24 | 2018-04-06 | 华东理工大学 | 酯交换合成碳酸苯甲酯和碳酸二苯酯的高稳定性钛催化剂 |
| CN107876092B (zh) * | 2017-11-24 | 2023-01-10 | 华东理工大学 | 一种具有环状结构的钛催化剂用作酯交换合成碳酸苯甲酯或碳酸二苯酯反应催化剂的用途 |
| CN115724878A (zh) * | 2022-11-14 | 2023-03-03 | 广州绿腾新材料有限公司 | 二次钛螯合物的制备方法及其在有机硅密封胶中的应用 |
| CN115724878B (zh) * | 2022-11-14 | 2024-02-13 | 广州绿腾新材料有限公司 | 二次钛螯合物的制备方法及其在有机硅密封胶中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1095480B (it) | 1985-08-10 |
| JPS53130627A (en) | 1978-11-14 |
| AU3394078A (en) | 1979-09-13 |
| ZA781292B (en) | 1979-02-28 |
| IT7821367A0 (it) | 1978-03-20 |
| AU519306B2 (en) | 1981-11-26 |
| BE865821A (fr) | 1978-10-09 |
| NL7803569A (nl) | 1978-10-17 |
| FR2387211B1 (fr) | 1984-06-22 |
| DE2812365A1 (de) | 1978-10-26 |
| FR2387211A1 (fr) | 1978-11-10 |
| NZ186666A (en) | 1979-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |