GB1572669A - Manufacture of esters - Google Patents
Manufacture of esters Download PDFInfo
- Publication number
- GB1572669A GB1572669A GB22276/77A GB2227677A GB1572669A GB 1572669 A GB1572669 A GB 1572669A GB 22276/77 A GB22276/77 A GB 22276/77A GB 2227677 A GB2227677 A GB 2227677A GB 1572669 A GB1572669 A GB 1572669A
- Authority
- GB
- United Kingdom
- Prior art keywords
- frame member
- container
- base member
- pallet
- auxiliary base
- 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
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
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)
Description
(40 parts) is removed bv distillation at 200"C/1.0 mm Hg pressure.
The product, m-phenoxybenzyl 2,2dimethyl-3-(2,2-dichlorovinyl) cyclopropane-1-carboxylate (360 parts) has a cis :trans isomer ratio of 37:63.
Example 3
Tetraisopropyl titanate (2.7 parts) is added to a mixture of methanol (38 parts), 3-phenoxybenzylalcohol (202 parts) and ethyl 2 ,2-dimethyl-3-(2 2-dichlorovinyl) cyclopropane-1-carboxylate (cis:trans isomer ratio 40:60) (270 parts) stirred under a nitrogen atmosphere at normal room temperature.
The colourless clear mixture is heated to 135-140"C over 1 hour and maintained at this temperature until the 3-phenoxybenzyl alcohol content of the mixture is less than 2.0%. During the reaction mixture is maintained at constant volume by the addition of dry toluene, simultaneously allowing the toluene/ethanol mixture to distil from the reaction mixture.
Upon completion of the reaction the residual ethyl 2,2-dimethyl-3-(2,2dichlorovinyl)cyclopropane-1-carboxylate (30 parts) is removed by distillation at 200"C/1.0 mm Hg pressure.
The product, m-phenoxybenzyl 2,2dimethyl-3-(2,2-dichlorovinyl) cyclopropane-1-carboxylate (382 parts) has a cistrans isomer ratio of 39:61.
Example 4
Tetraisopropyl titanate (7.2 parts) is added to dry methanol (50 parts) stirred under a nitrogen atmosphere at normal room temperature. To the mixture. a cloudy white suspension, is added ethyl 2,2 dimethyl-3-(2 2-dichlorovinyl) cyclopropane-l-carboxylate (cis:trans isomer rato 40:60) (118.5 parts) and 3-phenoxybenzyl alcohol (95 parts).
The mixture is heated to 158-160"C over 1 hour and maintained at this temperature until the 3-phenoxybenzyl alcohol content of the mixture is less than 2%. During the reaction the mixture is maintained at constant volume by the addition of dry xylene, simultaneously allowing the xylene/ethanol mixture to distil from the reaction.
Upon completion of the reaction the residual ethyl 2,2-dimethyl-3-(2,2- dichlorovinyl)cyclopropane-1-carboxylate (30 parts) is removed bv distillation at 200"C/1.0 mm Hg pressure.
The product. m-phenoxybenzyl 2.2dimethyl-3-(2,2-dichlorovinyl) cyclopropane-1-carboxylate (118 parts) has a cis trans isomer ratio of 42:58.
Example 5
The procedure described in Example I is repeated except that the 263.5 parts of ethyl 2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropane-1-carboxylate are replaced by 245 parts of methyl 2,2-dimethyl-3-(2,2dichlorovinyl) cyclopropane-1-carboxylate (cis:trans isomer ratio 45:55). There are obtained 350 arts of m-phenoxybenzyl 2,2-dimethyl-3-2,2-dichlorovinyl) cyclopropane-1-carboxylate having a cis:trans isomer ratio of 40:60.
WHAT WE CLAIM IS:
1. A process for the preparation of esters of m-phenoxybenzyl alcohol and its a-cyano and a-ethinyl derivatives with carboxylic acids which comprises mixing a methyl or ethyl ester of the carboxylic acid, m-phénoxybenzyl alcohol or its a-cyano or a-ethinyl derivative and a freshly-prepared methanolic suspension of tetramethyl titanate obtained by addition of tetraisopropyl titanate to dry methanol, and then heating the reaction mixture so that the methanol or ethanol which is formed in the reaction distils from the reaction mixture, until reaction is substantially complete.
2. A process as claimed in claim 1 wherein the reaction temperature is between 80" and 16û C.
3. A process as claimed in claim 1 or claim 2 wherein the reaction is carried out in the presence of an inert solvent.
4. A process as claimed in claim 3 wherein the inert solvent is such that the reaction mixture boils at the desired reaction temperature so that the methanol or ethanol formed during the process is distilled off with a part of the solvent.
5. A process as claimed in claim 4 wherein the inert solvent is added to the reaction mixture at a rate such that it balances the rate of distillation of solventl methanol or solvent/ethanol from the reaction mixture.
6. A process as claimed in any one of claims 1 to 5 wherein the amount of tetramethyl titanate catalyst used is from 0.0005 to 0.05 mol per mol of phenoxybenzylalcohol.
7. A process as claimed in any one of claims 1 to 6 wherein the methyl or ethyl ester of the carboxylic acid is used in excess over the m-phenoxybenzyl alcohol or its a-cyano or a-ethinyl derivative.
8. A process as claimed in claim 7 wherein from 1.05 to 1.20 moles of methyl or ethyl ester of the carboxylic acid are used per mol of m-phenoxybenzyl alcohol or its a-cyano or a-ethinyl derivative.
9. A process as claimed in any one of claims 1 to 8 wherein the carboxylic acid is a 2,2-dimethylcyclopropane carboxylic acid which gives insecticidal esters with mphenoxybenzyl alcohol or its a-cyano or a-ethinyl derivative.
10. A process as claimed in claim 9
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (5)
1. A wheeled pallet having a wheeled base member, a side frame member and an auxiliary base member pivotably mounted so as to be pivotable relative to the side frame member between a load-carrying fiat position on the wheeled base member and an upright position adjacent the side frame member, the pivotal mounting between the auxiliary base member and said side frame member being provided by an arrangement of aligned pins rotatably engaging sockets, the pins being longitudinally slidable relative to the sockets for withdrawal therefrom to permit removal of the auxiliary base member from the pallet, only at an intermediate position of the auxiliary base member intermediate the load-carrying flat position and the upright position.
2. A wheeled pallet according to claim 1 wherein said intermediate position is defined by means of a co-operating key and keyway gap associated with the auxiliary base member and said side frame member
3. A wheeled pallet according to claim 1 or claim 2 wherein the pins are provided on the side frame member and the sockets on the auxiliary base member.
4. A wheeled pallet according to claim 2 or claim 3 when dependent on claim 2 wherein a key is provided in proximity to one of the pins and the respective socket is provided with a collar having a gap serving as a keyway for said key, said key serving as an axial stop member with respect to said collar when said break providing said keyway is not aligned therewith.
5. A wheeled pallet according to claim 1 having an auxiliary base member and pivotal mounting therefor substantially as described hereinbefore with particular reference to
Figs. 8 to 10 of the accompanying drawings.
5. A wheeled pallet according to claim 1 having an auxiliary base member and pivotal mounting therefor substantially as described hereinbefore with particular reference to
Figs. 8 to 10 of the accompanying drawings.
**WARNING** end of CLMS field may overlap start of DESC **.
**WARNING** start of DESC field may overlap end of CLMS **.
respectively. A rectangular auxiliary base frame member 6 is pivotably mounted to the side frame member 4 by means of loop hinges 7.
The frame member 4 is fixedly secured to the base member 1 to form a substantially rigid basic framework. The frame member 5 is detachably mounted on the sub-frame 3 in any conventional manner. The frame member 4 is provided with studs 8 projecting outwardly of the load-containing space of the pallet. The frame member 5 has key-hole slot members 9 secured to it to enable it, when detached from the sub-frame 3 to be mounted in an upright manner on the frame member 4 (as seen in Fig. 2).
The auxiliary base frame member 6 can be pivoted between a flat load-carrying position on the base member 1 and an upright nesting position adjacent frame member 4.
The latter is provided with a catch 10 which serves to retain the auxiliary base frame member in its upright position when desired.
It is to be noted that the sub-frame 3 provides a wheel base that is sufficiently narrower than that at the broader end of the base member to allow the sub-frame 3 to pass between the wheels at the broader end of the base member of a second said pallet.
Thus, in use, although the pallet is of conventional rectangular base and side frame shape when used for carrying loads (Fig. 1), the frame member 5 and auxiliary base frame member 6 can be moved to their "nesting" positions (Fig. 2) and the pallet can then be nested with similar pallets as shown. in
Figs. 6 and 7.
It will be seen that the tapered base member 1 of each nesting pallet (except for those at the ends) nests within the tapered base member 1 of the adjacent pallet in front and receives the base member 1 of the adjacent pallet behind. Clearly, in the embodiment described above, the frame member 4 must be arranged to provide sufficient clearance below to receive the base member 1 of another pallet (see Fig. 3).
The trapezoidal base member may be sufficiently tapered to resemble a V-shape without departing from the trapezoidal shape of the wheel base.
Referring to Figs. 8 to 10, there is shown
a preferred form of pivotal connection of an
auxiliary base frame member 60 to a side
frame member 70 according to the present
invention and suitable for incorporation
in the pallet of Figs. 1 to 7.
The auxiliary base member 60 has two aligned cylindrical sockets 61, 62 the latter
of which has a flange 63 in the form of a
collar in which a gap 64 is provided.
The side frame member 70 has two aligned
pins 71, 72 secured at their right hand ends (as seen in the drawings) to a cross-bar 73 of the side frame member 70 by means of flat spacers 74. A key 75 is provided on the crossbar adjacent the left hand end of the pin 72.
The auxiliary base member 60 can be mounted on and removed from the side frame member 70 by sliding the sockets 61, 62 on to or off the pins 71, 72 respectively. However, this can only be done when the key 75 is aligned with the gap 64 which serves as a keyway therefor and this is arranged to occur when the auxiliary base member 60 is pivoted relative to the member 70 to a position intermediate the load-carrying and nesting positions.
WHAT WE CLAIM IS
1. A wheeled pallet having a wheeled base member, a side frame member and an auxiliary base member pivotably mounted so as to be pivotable relative to the side frame member between a load-carrying fiat position on the wheeled base member and an upright position adjacent the side frame member, the pivotal mounting between the auxiliary base member and said side frame member being provided by an arrangement of aligned pins rotatably engaging sockets, the pins being longitudinally slidable relative to the sockets for withdrawal therefrom to permit removal of the auxiliary base member from the pallet, only at an intermediate position of the auxiliary base member intermediate the load-carrying flat position and the upright position.
2. A wheeled pallet according to claim 1 wherein said intermediate position is defined by means of a co-operating key and keyway gap associated with the auxiliary base member and said side frame member
3. A wheeled pallet according to claim 1 or claim 2 wherein the pins are provided on the side frame member and the sockets on the auxiliary base member.
4. A wheeled pallet according to claim 2 or claim 3 when dependent on claim 2 wherein a key is provided in proximity to one of the pins and the respective socket is provided with a collar having a gap serving as a keyway for said key, said key serving as an axial stop member with respect to said collar when said break providing said keyway is not aligned therewith.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22276/77A GB1572669A (en) | 1977-05-26 | 1977-05-26 | Manufacture of esters |
| ZA00782481A ZA782481B (en) | 1977-05-26 | 1978-05-01 | Manufacture of esters |
| NZ187147A NZ187147A (en) | 1977-04-04 | 1978-05-02 | Preparation of esters m-phenoxybenzyl alcohol derivatives |
| AU35845/78A AU3584578A (en) | 1977-05-26 | 1978-05-05 | Manufacture of esters |
| JP6158378A JPS53147040A (en) | 1977-05-26 | 1978-05-23 | Process for preparing ester of mmphenoxybenzyl alcohol or alpha cyano and alphaaethynyl derivative thereof with carboxylic acid |
| DE19782822472 DE2822472A1 (en) | 1977-05-26 | 1978-05-23 | METHOD FOR PRODUCING ESTERS OF M-PHENOXY-BENZYL ALCOHOL AND ITS ALPHA-CYANO AND ALPHA-AETHINYL DERIVATIVES WITH CARBONIC ACIDS |
| FR7815646A FR2391995A2 (en) | 1977-05-26 | 1978-05-25 | PROCESS FOR OBTAINING CARBOXYL ESTERS FROM A M-PHENOXYBENZYL ALCOHOL |
| NL7805736A NL7805736A (en) | 1977-05-26 | 1978-05-26 | PROCESS FOR THE PREPARATION OF M-PHENOXYBENZYL ESTERS. |
| BE78200050A BE8T1 (en) | 1977-05-26 | 1978-06-20 | DETERGENT COMPOSITIONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22276/77A GB1572669A (en) | 1977-05-26 | 1977-05-26 | Manufacture of esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1572669A true GB1572669A (en) | 1980-08-28 |
Family
ID=10176763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22276/77A Expired GB1572669A (en) | 1977-04-04 | 1977-05-26 | Manufacture of esters |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS53147040A (en) |
| AU (1) | AU3584578A (en) |
| DE (1) | DE2822472A1 (en) |
| FR (1) | FR2391995A2 (en) |
| GB (1) | GB1572669A (en) |
| NL (1) | NL7805736A (en) |
| ZA (1) | ZA782481B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6605562B1 (en) | 1998-11-04 | 2003-08-12 | Basell Poliolefine Italia S.P.A. | Components and catalysts for the polymerization of olefins |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
| IN150399B (en) * | 1978-01-20 | 1982-09-25 | Fmc Corp | |
| DE2831193A1 (en) * | 1978-07-15 | 1980-01-24 | Bayer Ag | FLUORALKENYL-SUBSTITUTED CYCLOPROPANCARBONIC ACID ESTERS AND THEIR USE AS INSECTICIDES |
| FR2641532B1 (en) * | 1989-01-06 | 1991-03-29 | Solvay | PROCESS FOR THE PREPARATION OF (BETA) -HYDROXYBUTYRIC ACID ESTERS |
| IT1292108B1 (en) | 1997-06-09 | 1999-01-25 | Montell North America Inc | COMPONENTS AND CATALYSTS FOR THE POLYMERIZATION OF OLEFINE |
| IT1292107B1 (en) | 1997-06-09 | 1999-01-25 | Montell North America Inc | COMPONENTS AND CATALYSTS FOR THE POLYMERIZATION OF OLEFINE |
| CN1144778C (en) | 1998-10-08 | 2004-04-07 | 住友化学工业株式会社 | Process for preparing cyclopropane carboxylate |
| KR100679902B1 (en) | 1999-06-16 | 2007-02-07 | 스미또모 가가꾸 가부시끼가이샤 | Method for preparing cyclopropane carboxylate |
-
1977
- 1977-05-26 GB GB22276/77A patent/GB1572669A/en not_active Expired
-
1978
- 1978-05-01 ZA ZA00782481A patent/ZA782481B/en unknown
- 1978-05-05 AU AU35845/78A patent/AU3584578A/en active Pending
- 1978-05-23 JP JP6158378A patent/JPS53147040A/en active Pending
- 1978-05-23 DE DE19782822472 patent/DE2822472A1/en not_active Withdrawn
- 1978-05-25 FR FR7815646A patent/FR2391995A2/en active Pending
- 1978-05-26 NL NL7805736A patent/NL7805736A/en not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6605562B1 (en) | 1998-11-04 | 2003-08-12 | Basell Poliolefine Italia S.P.A. | Components and catalysts for the polymerization of olefins |
| US6689850B2 (en) | 1998-11-04 | 2004-02-10 | Basell Poliolefine Italia S.P.A. | Process for the polymerization of olefins |
| US6699814B2 (en) | 1998-11-04 | 2004-03-02 | Basell Poliolefine Italia S.P.A. | Catalysts for the polymerization of olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53147040A (en) | 1978-12-21 |
| ZA782481B (en) | 1979-04-25 |
| NL7805736A (en) | 1978-11-28 |
| AU3584578A (en) | 1979-11-08 |
| DE2822472A1 (en) | 1978-12-14 |
| FR2391995A2 (en) | 1978-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |