Control of organic impurities in polycarbonate synthesis

Patent metadata

Field	Value
Publication number	US-10253165-B2
Application number	US-201615553279-A
Country	US
Kind code	B2
Filing date	Feb 25, 2016
Priority date	Feb 26, 2015
Publication date	Apr 9, 2019
Grant date	Apr 9, 2019

Abstract

Polymerization processes comprising melt polymerizing a carbonate and a dihydroxy compound in the presence of an amount of a beta organic catalyst so as to give rise to a polycarbonate product, wherein the amount of beta organic catalyst comprises at least one onium salt and also comprises triphenyl phosphonium oxide (TPPO), and wherein the TPPO represents less than about 0.3 weight % of the sum of the weights of the at least one onium salt and the TPPO in the amount of beta organic catalyst.

First claim

What is claimed:

1. A polymerization process comprising:
melt polymerizing a carbonate and a dihydroxy compound in the presence of an amount of a beta organic catalyst so as to give rise to a polycarbonate product,
wherein the amount of beta organic catalyst comprises at least one onium salt and also comprises triphenyl phosphonium oxide, and
wherein the triphenyl phosphonium oxide represents less than about 0.3 weight % of the sum of the weights of the at least one onium salt and the triphenyl phosphonium oxide in the amount of beta organic catalyst.

2. The polymerization process of claim 1 , wherein (a) the at least one onium salt comprises tetramethyl phosphonium acetate, tetrapropyl phosphonium acetate, tetrabutyl phosphonium acetate, or tetraphenyl phosphonium acetate (b), the triphenyl phosphonium oxide represents less than about 0.2 weight % of the sum of the weights of the at least one onium salt and triphenyl phosphonium oxide in the amount of beta organic catalyst, or (a) and (b).

3. The polymerization process of claim 1 , wherein the melt polymerizing is performed in the presence of an alpha inorganic catalyst that comprises one or more alkali metal salts, one or more alkaline earth metal salts, or any combination thereof.

4. The polymerization process of claim 1 , wherein the polycarbonate product is an oligomerization product having a number average molecular weight of less than or equal to about 13 kDalton (polystyrene basis) and wherein the oligomerization product exhibits a Fries rearrangement level of less than about 500 ppm.

5. The polymerization process of claim 1 , wherein the polycarbonate product is a polymerization product having a number average molecular weight of more than about 13 kDalton (polystyrene basis) and wherein the polymerization product exhibits a Fries rearrangement level of from about 300 ppm to about 1200 ppm.

6. The polymerization process of claim 1 , wherein the beta organic catalyst comprises an amount of metal and wherein the amount of metal present is based upon the weight of the catalyst compound is present, wherein the metal comprises at least one of sodium, potassium, cesium; and wherein: if the compound comprises a sodium sulfate, the amount of sodium is 1 ppm to 1,690 ppm; if the compound comprises a cesium sulfate, the amount of cesium is 10 ppm to 275 ppm; if the compound is a potassium hydroxide, the amount of potassium is greater than 0 to 50 ppm; and/or if the compound comprises a cesium hydroxide, the amount of cesium is 10 ppm to 140 ppm.

7. The polymerization process of claim 1 , further comprising adding a quencher composition.

8. A system comprising:
a reactor chain configured to synthesize a polycarbonate product; and
an amount of beta organic catalyst,
wherein the amount of beta organic catalyst comprises at least one onium salt and also comprises triphenyl phosphonium oxide, and
wherein the triphenyl phosphonium oxide represents less than about 0.3 weight % of the sum of the weights of the at least one onium salt and the triphenyl phosphonium oxide in the amount of beta organic catalyst.

9. The system of claim 8 , wherein the reactor chain comprises a first stage configured to synthesize polycarbonate oligomerization product having a number average molecular weight of less than or equal to about 13 kDalton (polystyrene basis).

10. The system of claim 8 , wherein the reactor chain further comprises a second stage configured to synthesize a polycarbonate polymerization product having a number average molecular weight of more than about 13 kDalton (polystyrene basis).

11. The system of claim 8 , wherein the reactor chain further comprises a second stage configured to synthesize a polycarbonate polymerization product having a number average molecular weight of from about 25,000 to 70,000 Dalton (polystyrene basis).

12. The system of claim 8 , wherein the polycarbonate product is an oligomerization product having a number average molecular weight of less than or equal to about 13 kDalton (polystyrene basis) and wherein the oligomerization product exhibits a Fries rearrangement level of less than about 500 ppm.

13. The system of claim 8 , wherein the system is configured to synthesize a polycarbonate polymerization product that exhibits a Fries rearrangement level of from about 300 ppm to about 1100 ppm.

14. The system of claim 8 , wherein the beta organic catalyst comprises an amount of metal and wherein the amount of metal present is based upon which compound is present, wherein the metal comprises at least one of sodium, potassium, cesium; and wherein: if the compound comprises a sodium sulfate, the amount of sodium is 1 ppm to 1,690 ppm; if the compound comprises a cesium sulfate, the amount of cesium is 10 ppm to 275 ppm; if the compound is a potassium hydroxide, the amount of potassium is greater than 0 to 50 ppm; and/or if the compound comprises a cesium hydroxide, the amount of cesium is 10 ppm to 140 ppm.

15. A polycarbonate composition made via the system of claim 8 , the polycarbonate composition having a number average molecular weight of between about 8 and about 70 kDalton (polystyrene basis) and exhibiting a Fries rearrangement level of less than 900 parts per million by weight of the product.

16. The polymerization process of claim 1 , wherein the dihydroxy compound comprises a diaryl carbonate ester.

17. The polymerization process of claim 16 , further comprising preparing the diaryl carbonate ester by transesterification reaction containing a dialkylcarbonate, phosgenation of phenol.

18. The polymerization process of claim 16 , wherein the diaryl carbonate ester comprises bis(4-nitrophenyl)carbonate, bis(2-chlorophenyl)carbonate, bis(4-chlorophenyl)carbonate, bis(methyl salicyl)carbonate, bis(4-methylcarboxylphenyl)carbonate, bis(2-acetylphenyl)carboxylate, bis(4-acetylphenyl)carboxylate, or a combination comprising at least one of the foregoing.

19. The polymerization process of claim 16 , wherein the diaryl carbonate ester comprises less than or equal to 23 parts per billion by weight of molybdenum; less than or equal to 23 parts per billion by weight vanadium; less than or equal to 23 parts per billion by weight chromium; less than or equal to 57 parts per billion by weight titanium; less than or equal to 284 parts per billion by weight of niobium; less than or equal to 23 parts per billion by weight of nickel; less than or equal to 6 parts per billion by weight zirconium; less than or equal to 6 parts per billion by weight of iron.

20. The polymerization process of claim 1 , wherein:
the triphenyl phosphonium oxide represents less than or equal to about 0.280 weight % of the sum of the weights of the at least one onium salt and the triphenyl phosphonium oxide in the amount of beta organic catalyst and
the at least one onium salt comprises tetraphenyl phosphonium acetate.

Assignees

• Sabic Global Technologies Bv

Inventors

• Bojarski Aaron David
• Garcia Agudo Jorge A

Classifications

• C08G64/20 Primary

  General preparatory processes · CPC title

• C08G64/42

  Chemical after-treatment · CPC title

• G16C20/10

  Analysis or design of chemical reactions, syntheses or processes · CPC title

• C08G64/307

  and phenols · CPC title

• C08K5/50 Primary

  Phosphorus bound to carbon only · CPC title