Process of preparing a fluid rare earth alkoxylation catalyst

Details Process of preparing a fluid rare earth alkoxylation catalyst Process of preparing a fluid rare earth alkoxylation catalyst

2000-12-15

2003-02-04

Bell, Mark L. (Department: 1755)

Catalyst, solid sorbent, or support therefor: product or process

Catalyst or precursor therefor

Phosphorus or compound containing same

C502S303000, C423S299000, C423S305000, C987S300000

Reexamination Certificate

active

06514898

ABSTRACT:

This invention relates to a process of preparing a rare earth catalyst useful in an alkoxylation process.
BACKGROUND OF THE INVENTION
A large variety of products useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvent, and chemical intermediates, are prepared by the addition reaction (alkoxylation reaction) of alkylene oxides (epoxides) with organic compounds having one or more active hydrogen atoms. For example, particular mention may be made of the alkanol ethoxylates and alkyl-substituted phenol ethoxylates prepared by the reaction of ethylene oxide with aliphatic alcohols or substituted phenols of about 6 to 30 carbon atoms. Such ethoxylates, and to a lesser extent corresponding propoxylates and compounds containing mixed oxyethylene and oxypropylene groups, are widely employed as nonionic detergent components of commercial cleaning formulations for use in industry and in the home. As another example, the addition reaction of propylene oxide with polyols provides intermediates for the preparation of polyurethane products.
An illustration of the preparation of an alkanol ethoxylate (represented by formula III below) by addition of a number (n) of ethylene oxide molecules (formula 11) to a single alkanol molecule (formula I) is presented by the equation
The present invention particularly relates to an alkoxylation reaction catalyzed by the phosphate salts of one or more of the rare earth elements.
Alkylene oxide addition reactions are known to produce a product mixture of various alkoxylate molecules having different numbers of alkylene oxide adducts (oxyalkylene adducts), e.g., having different values for the adduct number n in formula III above. The adduct number is a factor which in many respects controls the properties of the alkoxylate molecule, and efforts are made to tailor the average adduct number of a product and/or the distribution of adduct numbers within a product to the product's intended service.
It is known that alcohol alkoxylate products having a narrow range alkylene oxide adduct distribution are preferred for use in certain detergent formulations (Great Britain Patent No. 1,462,134; Derwent Publications Research Disclosure number 194,010). Narrow-range alcohol alkoxylates are also known to be particularly valuable as chemical intermediates in the synthesis of certain carboxylated alkyl polyethers (U.S. Pat. No. 4,098,818) and of certain alkyl ether sulfates (Great Britain Patent No. 1,553,561).
U.S. Pat. No. 5,057,627 describes an alkoxylation process catalyzed phosphate salts of the rare earth elements. These catalysts were typically prepared by adding an aqueous solution of a rare earth compound such as lanthanum chloride to an aqueous sodium orthophosphate or H
3
PO
4
solution. The resulting catalyst was a solid powder that was stable with a long shelf-life. However, often the reaction mixture prepared by these catalysts lead to an increase in the viscosity of the mixture to 1000 centipoise or more. U.S. Pat. No. 5,057,627 also describes a process where an alkylphosphate is added to a lanthanum solution of 2-ethoxyethanol and NEODOL™ 23 Alcohol. Such a system may produce a lower viscosity mixture, however, these catalysts have a slow reaction time.
It is desirable to prepare a catalyst that provides a low viscosity reaction system with faster reaction time.
SUMMARY OF THE INVENTION
A process for the preparation of a fluid rare earth phosphate catalyst composition comprising:
a) providing a rare earth salt soluble in C
9
-C
30
active hydrogen containing organic compounds at a temperature of less than 120° C.;
b) adding and dissolving the rare earth salt in a C
9
-C
30
active hydrogen containing organic compounds thereby producing a rare earth/organic solution; and
c) adding phosphoric acid to the rare earth/organic solution in a rare earth to phosphoric acid molar ratio in the range of 0.7:1 to 1.3:1 thereby producing the fluid rare earth phosphate catalyst composition.
Further, processes for the preparation of alkylene oxide adducts of active hydrogen containing organic compounds are provided, comprising contacting an alkylene oxide reactant comprising one or more vicinal alkylene oxide with an active hydrogen containing reactant comprising one or more active hydrogen containing organic compounds in the presence of the fluid catalyst composition prepared by certain processes.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has now been found that the alkoxylation reaction carried out in the presence of the rare earth phosphate catalyst composition prepared by the process of the invention, decreases reaction time and is easier to handle.
In the process of the invention, a fluid rare earth phosphate catalyst is prepared by the steps comprising a) providing a certain rare earth salt, b) adding and dissolving the rare earth salt in a C
9
-C
30
active hydrogen containing organic compounds, preferably in a C
9
-C
30
primary mono-hydric alkanol or alkylphenol, more preferably in a C
9
-C
30
primary mono-hydric alkanol; then c) adding phosphoric acid to the rare earth/organic solution, or more preferably to the rare earth/alkanol solution. It has been surprisingly found that the desirable catalyst composition can be prepared in the C
9
-C
30
active hydrogen containing organic compound without the presence of low molecular weight alcohol or alkoxides (carbon number of less than 8).
When the catalyst is prepared according to the invention, the rare earth phosphate is substantially uniformly dispersed in the alkanol having an average particle size of less than about 2 microns, more preferably medium diameter particles are less than about 1 micron. The catalyst composition comprising the dispersed rare earth phosphate salt and the alkanol has a viscosity of about less than 50 centipoise, and is fluid. The term “fluid” means having particles which easily move and change their relative position without a separation of the mass, and which readily yield to pressure.
As the terminology is used herein, the “rare earth” elements are those of atomic numbers 39 and 57 through 71, elements of the “lanthanum series” are those of atomic numbers 57 through 71; the “lanthanide” elements are those of atomic numbers 58 through 71. Traditionally, the lanthanum series has further been divided into the “cerium earth” group of atomic numbers 57 through 62, the “terbium earth” group of atomic numbers 63 through 66, and the “yttrium earth” group of atomic numbers 67 through 71 (so named not because yttrium is a member of the group, but because yttrium is found with these elements in nature).
In general terms, the catalyst for the process of the invention comprises one or more of the phosphate salts of the rare earth metals. In one preferred embodiment, the catalyst comprises one or more of the phosphate salts of the lanthanum series elements. In another embodiment, the catalyst comprises one or more of the phosphate salts of the lanthanide elements. In a further specific embodiment, the catalyst comprises one or more of the phosphate salts of the elements of the cerium earth group. In still another specific embodiment, the catalyst comprises a mixture of rare earth metal phosphate salts wherein the distribution of the rare earth elements substantially corresponds to that of a naturally occurring rare earth ore, for example, monazite, bastnasite, xenotime, gadolinite or euxenite.
The catalyst in a given application of this process suitably contains the phosphate salt(s) of either one or a mixture of the rare earth elements. In one respect, preference can be expressed for catalysts comprising in catalytically effective amount one or more of the phosphate salts of elements selected from the group comprising cerium, lanthanum, praseodymium, neodymium, yttrium, samarium, gadolinium, dysprosium, erbium, and ytterbium. In another respect, catalysts comprising a catalytically effective amount of one or more of the phosphate salts of the cerium earth group elements are particularly preferred, while catalysts comprising a catalytically effective amount of

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