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Methods of making (ALK)acrylic esters in flow reactors

A technology of acrylate and microfluidic reactors, applied in chemical instruments and methods, chemical/physical/physical chemical reactors, preparation of carboxylic acid halides, etc., can solve problems such as fire or explosion

Active Publication Date: 2018-10-23
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Even when cooled, the reaction may cause a fire or explosion when performed on an industrial scale

Method used

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  • Methods of making (ALK)acrylic esters in flow reactors
  • Methods of making (ALK)acrylic esters in flow reactors
  • Methods of making (ALK)acrylic esters in flow reactors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0215] The following abbreviations are used in this section: NMR = nuclear magnetic resonance, mL = milliliter, μL = microliter, s = second, min = minute, g = gram, μm = micrometer, mm = millimeter, m = meter, ppm = parts per Parts per million, mol = mole, mol% = mole percent, kPa = kilopascal.

[0216] Abbreviations for materials used in this section are provided in Table 1 along with descriptions of the materials.

[0217] Table 1

[0218] Material

illustrate

BP

4-hydroxybenzophenone, purchased from Belgium Aldrich company (Aldrich, Belgium)

3CPC

3-chloropropionyl chloride, purchased from Belgium Aldrich Company (Aldrich, Belgium)

TEA

Triethylamine, purchased from Belgium Aldrich company (Aldrich, Belgium)

DCM

Dichloromethane, purchased from Belgium Aldrich company (Aldrich, Belgium)

water

Deionized water

ACLs

Acryloyl chloride, available from ABCR, Germany (ABCR, Germany)

Isofol 20

>...

Embodiment 1 to 17

[0249] Examples 1 to 17 (EX-1 to EX-17)

[0250] For EX-1, the following procedure was performed at ambient temperature using the mixing apparatus described above using Microreactor B. Syringe 1 contained 15g BP, 22g TEA and 22g water. Syringe II contains 3g ACL and 20g DCM. Each syringe was placed in a separate syringe pump and the speed of the pump was controlled to deliver the mixture at the flow rate shown in EX-1 in Table 3 below. Seal the two unused addition ports of the mixing device with stoppers. The molar flow rate ratio of BP:ACL:TEA pumped to the mixing device was 1:1.1:2.9. Separation of aqueous and organic phases was observed in the collection vessel. Analysis of the upper aqueous phase by NMR indicated about 8 mole percent acrylic acid-TEA salt and about 92 mole percent TEA-HCl salt. Analysis of the lower organic phase by NMR indicated about 51 mole % 4-acryloyloxybenzophenone (ABP), about 0.01 mole % BP and about 42 mole % of the above TEA salt. Analysi...

Embodiment 18

[0262] Example 18 (EX-18)

[0263] EX-18 was performed using the procedure of EX-1, except that Syringe II contained 3 g MAC and 20 g DCM, and the flow rates were as indicated in EX-18 in Table 4 below. The resulting molar flow rate ratio of BP:MAC:TEA was 1:1.1:2.9. Analysis of the product stream indicated a % composition of 98%. The blend composition, flow rate, molar flow rate ratio of BP:ACL:TEA and % composition are provided in Table 4.

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Abstract

A method of making an (alk)acrylic ester in a microflow reactor.

Description

Background technique [0001] (Alk)acrylates have various uses, such as monomers or comonomers for the preparation of various polymers. (Alk)acrylates can be produced industrially, eg by esterification of alcohols with (alk)acrylic acid under azeotropic conditions, wherein water is removed from the reaction mixture by distillation during the reaction. This method is not useful for making all (alk)acrylates, especially those that are unstable at higher temperatures. [0002] (Alk)acrylates can also be prepared by adding alcohol to (alk)acryloyl chloride. This reaction may be difficult to perform on an industrial scale, since it is necessary to strictly exclude water from the reaction in order to proceed in good yields. Also, the reaction is highly exothermic and therefore requires very slow addition of the alcohol to the (alk)acryloyl chloride with effective cooling. Even when cooled, the reaction can cause a fire or explosion when performed on an industrial scale. Contents ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/54
CPCC07C67/14C07C69/54B01J19/0093B01J19/248B01J2219/0086B01J2219/00889
Inventor 鲁道夫·J·达姆斯鲁迪·W·范坎彭豪特
Owner 3M INNOVATIVE PROPERTIES CO