MXPA00003761A - Method of ethoxylation using vapor phase discharge of ethylene oxide - Google Patents

Abstract

The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form during transport to said reaction vessel, during discharge into said reaction vessel, and during contacting of the organic compound with the alkylene oxide . The result is an alkoxylated product containing less flocculant.

Description

TITLE: ETOXILATION METHOD USING PHASE DOWNLOAD ETHYLENE OXIDE VAPOR Field of the Invention The present invention is a method for alkoxylation of organic compounds, preferably polyalkylene glycols, by exposing organic compounds to alkylene oxide vapor which is not compressed in a liquid phase for transport or introduction purposes. in the reactor. The method results in alkoxylation products containing less, few or none flocculent. Antecedents of the Inven < A variety of organic materials react under suitable conditions with an adduction material, such as alkylene oxide, particularly ethylene oxide or propylene oxide, to form alkoxylated organic materials. Typically, the alkylene oxide adduction material is compressed in liquid form to transport to, and discharge into, the reactor. Unfortunately, even if the alkylene oxide is decompressed in the vapor phase before the alkoxylation reaction begins, the preliminary compression of the alkylene oxide in the liquid phase tends to increase the flocculation in the alkylation product. A method is needed by which to form alkoxylated products that contain little, less or no floccules. Summary of the Invention The present invention provides a method which comprises contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form before and during transport to the reaction vessel, during discharge into the reaction vessel, and during contact with the organic compound.

Description of the Invention The present invention provides a method for producing an alkoxylation product with little, less or no floccules. According to the present method, the alkylene oxide adduction material is not compressed in liquid form in order to transport and / or to introduce the material into the alkoxylation reactor. The alkylene oxide is transported and discharged into the reactor in the vapor phase. Without limiting the present invention to any particular theory or mechanism, it is believed that the compression of the ethylene oxide in the liquid phase produces minimal amounts of oligomers or polymers that contribute to the formation of floccule in the substrate. It is believed that the present invention reduces floccules by preventing the formation of these oligomers or polymers in the alkylene oxide. The alkoxylation reaction, by itself, takes place under standard conditions. The reaction takes place at any suitable temperature, preferably from about 10 ° C to about 160 ° C. For practical purposes, most commercial operations will be carried out in the temperature range of about 50 ° C to about 200 ° C. The method is useful for alkoxylating any suitable alkoxylabtable organic material. Suitable materials include, but are not necessarily limited to, linear or branched polyhydric, unsaturated alcohols, saturated alcohols, alkylphenols, polyols, aldehydes, ketones, amines, amides, organic acids, and mercaptans. Preferred organic materials are usually selected from the group consisting of: (a) polyhydric alcohols containing a total of about 2 to about 30 carbon atoms and having the general formula R2 R1 - C - OH wherein R1, R2 and R 'independently are selected from the group consisting of linear and branched acyclic groups, alicyclic groups, aryl groups, cyclic groups, and hydrogen, and may contain one or more functional groups selected from the group consisting of amine groups , carboxyl groups, hydroxy groups, halogen atoms, nitro groups, carbonyl groups, and amide groups.

Representative but not exhaustive examples of various polyhydric alcohols which can be alkoxylated according to the present invention are: ethylene glycol, 1,2-propylene glycol; 1,4-butanediol; 1,6-hexanediol; 1,10-decanodiol; 1,3-butylene glycol; diethylene glycol; diethylene glycol monobutyl ether; diethylene glycol monomethyl ether; diethyl glycol monoethyl ether; dipropylene glycol; dipropylene glycol monomethyl ether; ethylene glycol monomethyl ether; ethylene glycol monoethyl ether; ethylene glycol monobutyl ether; hexylene glycol; mannitol; sorbitol; pentaerythritol; dipentaerythritol; tripentaerythritol; trimethylolpropane; trimethylolethane; neopentyl glycol; diethanolamine; triethanolamine; diisopropanolamine; triisopropanolamine; 1,4-dimethylolcyclohexane; 2, 2-bis (hydroxymethyl) propionic acid; 1,2-bis (hydroxymethyl) benzene; 4, 5-bis (hydroxymethyl) furfural; 4, 8-bis (hydroxymethyl) tricyclo- [5, 2, 1, Ojdecane; tartaric acid; 2-ethyl-l, 3-hexanediol; 2-amino-2-ethyl-l, 3-propanediol; triethylene glycol; tetraethylene glycol; glycerol; ascorbic acid. Representative, but not exhaustive examples of various aldehydes and ketones that can be alkoxylated according to the present invention are lauryl aldehyde; benzaldehyde; 2-undecanonacetophenone; 2,4-pentandione; acetylsalicylic acid; ortho-chlorobenzaldehyde; para-chlorobenzaldehyde; cinnamic aldehyde; diisobutyl ketone; ethyl acetate; ethylamyl ketone; camphor; para-hydroxybenzaldehyde; 2-carboxybenzaldehyde; 4-carboxybenzaldehyde; salicialdehyde; octyl aldehyde; decyl aldehyde; p-methoxybenzaldehyde; p-aminobenzaldehyde; phenylacetaldehyde, acetoacetic acid, 2,5-dimethoxybenzaldehyde, 1-naphthylaldehyde; terephthaldehyde; (b) aldehydes and ketones having from about 2 to about 30 carbon atoms and having the general formula R1-C = O R2 wherein R1 and R2 independently are selected from the group consisting of hydrogen, linear and branched acyclic groups, alicyclic groups, cyclic groups, and aryl groups, and may contain one or more functionalities selected from the group consisting of carboxyl groups, hydroxyl groups , halogen atoms, nitro groups, amine groups, and amide groups; (c) primary, secondary and tertiary amides having from about 1 to about 30 carbon atoms and having the general formula O R2 1 / R1 - c- N \ R1 wherein R1, R2 and R3 independently are selected from the group consisting of hydrogen, linear and branched acyclic groups, alicyclic groups, cyclic groups, and aryl groups, and may contain one or more functionalities selected from the group consisting of hydroxyl groups, carboxyl, carbonyl groups, amine groups, nitro groups and halogen atoms. Representative, but not exhaustive, examples of amides that can be alkoxylated according to the present invention are: formamide; benzamide; acetanilide; salicylamide; n-acetoacetanilide; ortho-acetoacetotoluidide; acrylamide; M, N-diethyl toluamide; N, N-dimethylacetamide; N, N-dimethylformamide; phthalimide; octylamide; decilamide; lauryl amide; stearylamide; N, N-dimethylalauryl amide; N, N-dimethylacrylamide; para-chlorobenzamide; para-methoxybenzamide; para-aminobenzamide; para-hydroxybenzamide; ortho-nitrobenzamide; N-acetyl para-aminophenol; 2-chloroacetamide; oxamide; N, N-methyl-bis-acrylamide; (d) primary, secondary and tertiary amines having from about 1 to about 30 carbon atoms, and having the general formula R2 / R! -N? R3 wherein R1, R2 and R3 independently are selected from the group consisting of hydrogen, linear and branched acyclic groups, alicyclic groups, cyclic groups, and aryl groups, and may contain one or more functionalities selected from the group consisting of hydroxyl groups, carbonyl, halogen atoms, carboxyl groups, nitro groups and amide groups. Representative but not exhaustive examples of amines that can be alkoxylated according to the present invention are: aniline; benzylamine; hexadecylamine; triphenylamine; amino acid acid; anthranilic acid; cyclohexylamine; ter-octylamine; ortho-phenylenediamine; meta-phenylenediamine; para-phenylenediamine; N-acetyl para-aminophenol; 2-amino-4-chlorophenol; 2-amino-2-ethyl-1,3-propanediol; ortho-aminophenol; para-amiphophenol; para-aminosalicylic acid; benzyl-N, N-dimethylamine; tert-butylamine; 2-chloro-4-aminotoluene; 6-chloro-2-aminotoluene; meta-chloroaniline; ortho-chloroaniline; para-chloroaniline; 4-chloro-2-nitroaniline; cyclohexylamine; dioutiiiamine; 2,5-dichloroaniline; 3, 4-dichloroaniline; dicyclohexylamine; diethanolamine; N, N-diethanolamine; N, N-diethyl-meta-toluidine; N, N-diethylaniline; diethylenetriamine; diisopropanolamine; N, N-dimethylethanolamine; N, N-dimethylaniline; 2, -dinitroaniline; diphenylamine; ethyl-para-aminobenzoate; N-ethylethanolamine; N-ethyl-1-naphthylamine; N-ethyl-ortho-toluidine; N-ethylaniline; ethylenediamine; hexamethylenetetraamine; 2, 4-lutidine; N-methylaniline; methyl anthranilate; p, p'-diaminodiphenyl methanol; ortho-nitroaniline; para-nitroaniline; ter-octylamine; piperazine; ethanolamine; isopropanolamine; ortho-toluidine; para-toluidine; 2,4-toluenediamine; triethanolamine; tributylamine; triisopropanolamine; 2, -dimethylxidine; para-methoxyaniline; nitrilotriacetic acid; N-phenyl-1-na tilamine; (e) organic acids having from about 1 to about 30 carbon atoms, and having the general formula O R1-C-OH wherein R1 is selected from the group consisting of hydrogen, linear and branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, and may contain one or more functionalities selected from the group consisting of carbonyl groups, hydroxyl groups , halogen atoms, nitro groups, amine groups and amide groups. Representative but not exhaustive examples of organic acids that can be alkoxylated according to the present invention are: formic acid; acetic acid; valeric acid; heptanoic acid; 2-ethylhexanoic acid; lauric acid; stearic acid; oleic acid; resin oil acids; Hydrogenated resin oil acids; benzoic acid; salicylic acid; adipic acid; azelaic acid; fumaric acid; citric acid; acrylic acid; aminoacetic acid; para-aminosalicylic acid; anthranilic acid; butyric acid; propionic acid; ricinoleic acid; chloroacetic acid; ortho-chlorobenzoic acid; 2,4-dichlorophenoxyacetic acid; ter-decanoic acid; para-aminobenzoic acid; abietic acid; Itaconic acid; lactic acid; Glycolic Acid; malic acid; myristic acid; palmitic acid; ter-pentar.oic acid; phenylacetic acid; mandelic acid; sebacic acid; fatty acids of sebe-hydrogenated tallow fatty acids; tartaric acid; trichloroacetic acid; 2, 4, 5-trichlorophenoxyacetic acid; undecylenic acid; crotonic acid; pelargonic acid; acetoacetic acid; para-nitrobenzoic acid; ascorbic acid; nitrilotriacetic acid; Naphenic acid; 1-naphthoic acid; trimellitic acid; (f) alkylphenols having from about 6 to about 30 carbon atoms, and having the general formula wherein R1, R ', R3, R4 and R5 independently are selected from the group consisting of hydrogen, halogen atoms, hydroxyl groups, nitro groups, carbonyl groups, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, and may contain one or more functionalities selected from the group consisting of halogen atoms, ether groups, nitro groups, carboxyl groups, carbonyl groups, amine groups, amide groups, and hydroxyl groups. Representative examples, but not exhaustive, of various phenols which can be alkoxylated according to the present invention are: phenol; ortho-cresol; meta-cresol; para-cresol; 2,4-dimethyl? -phenyl; 2,5-dimethylphenol; 2,6-dimethylphenol; ortho-chlorophenol; meta-chlorophenol; para-chlorophenol; para-nitrophenol; para-methoxyphenol; salicylic acid; meta-hydroxyacetophenone; para-aminophenol; ortho-phenylphenol; nonylphenol; octylphenol; t-butyl-para-cresol; hydroquinone; catechol; resorcinol; pyrogallol; 1-naphthol; 2-naphthol; 4, '-isopropylidenediphenol (bisphenol A); methyl salicylate; benzyl salicylate; 4-chloro-2-nitrophenol; para-t-butylphenol; 2,4-di-t-amylphenol; 2,4-dinitrophenol; para-hydroxybenzoic acid; 8-hydroxyquinoline; methyl-para-hydroxybenzoate; 2-nitro-para-cresol; ortho-nitrophenol; para-phenylphenol; phenyl salicylate; salicylaldehyde; p-hydroxy benzaldehyde; 2-amino-4-chlorofol; ortho-aminophenol; salicylamide; (g) mercaptans of the general formula R1 Rz - C - SH wherein R1, R2 and R3 independently are selected from the group consisting of hydrogen, linear and branched acyclic groups, alicyclic groups, cyclic groups, and aryl groups having from about 1 to about 30 carbon atoms, and may contain one or more functionalities selected from the group consisting of carboxyl groups, hydroxyl groups, halogen atoms, nitro groups, amine groups, and amide groups; and (h) alcohols having the general formula ROH wherein R is selected from the group consisting of linear and branched alkyl groups having from about 1 to about 30 carbon atoms, aryl groups, cyclic groups having from about 6 to about 30 carbon atoms, and olefinic and acetylenic groups having from about 1 to about 30 carbon atoms. Representative examples, but not exhaustive, of alcohols that can be alkoxylated according to the present invention are: 1-dcdecanol; 1-tridecanol; 1-tetradecanol; 1-pentadecanol; 1-hexadecanol; 1-heptadecanol; 1-octadecanol; 1-nonadecanol; 1-eicosanol; 1-docosanol; 2-methyl-1-undecanol; 2-propyl-l-nonanol; 2-butyl-1-octanol; 2-methyl-l-tridecanol; 2-ethyl-l-dodecanol; 2-propyl-1-undecanol; 2-butyl-1-decanol; 2-pentyl-1-nonanol; 2-hexyl-1-octanol; 2-methyl-l-pentadecanol; 2-ethyl-1-tetradecanol; 2-propyl-l-tridecanol; 2-butyl-l-dodecanol; 2-pentyl-1-undecanol; 2-hexyl-1-decanol; 2-heptyl-1-decanol; 2-hexyl-l-nonanol; 2-octyl-l-octanol; 2-methy1-1-heptadecanol; 2-ethyl-1-hexadecanol; 2-propyl-l-pentadecanol; 2-butyl-1-tetradecanol; 1-pentyl-l-tridecanol; 2-hexyl-1-dodecanol; 2-octyl-1-decanol; 2-nonyl-l-nonanol; 2-dodecanol; 3-dodecanol; 4-dodecanol; 5-dodecanol; 6-dodecanol; 2-tetradecanol; 3-tetradecanol; 4-tetradecanol; 5-tetradecanol; 6-tetradecanol; 7-tetradecanol; 2-hexadecanol; 3-hexadecanol; 4-hexadecanol; 5-hexadecanol; 6-hexadecanol; 7-he :: adecano_; 8-hexadecanol; 2-octadecanol; 3-octadecanol; 4-octadecanol; 5-octadecanol; 6-octadecanol; 7-octadecanol; 8-octadecanol; 9-octadecanol; 9-octadecenol; 2,4,6-trimethyl-1-heptanol; 2, 4, 6, 8-tetramethyl-1-nonanol; 3, 5, 5-trimethyl-1-hexanol; 3, 5, 5, 7, 7-pentamethyl-1-octanol; 3-butyl-l-nonanol; 3-butyl-l-undecanol; 3-hexyl-l-undecanol; 3-hexyl-l-tridecanol; 3-octyl-l-tridecanol; 2-methyl-2-undecanol; 3-methyl-3-undecanol; 4-methyl-4-undecanol; 2-methyl-2-tridecanol; 3-methyl-3- ridecanol; 4-methyl-3-tridecanol; 4-methyl-4-tridecanol; 3-ethyl-3-decanol; 3-ethyl-3-dodecanol; 2,4,6, 8-tetramethyl-2-nonanol; 2-methyl-3-undecanol; 2-methyl-4-undecanol; 4-methyl-2-undecanol; 5-methyl-2-undecanol; 4-ethyl-2-decanol; 4-ethyl-3-decanol; tetracosanol; hexacosanol; octacosanol; triacontanol; dotriacontanol; hexatriacontanol; 2-decyltetradecanol; 2-dodecylhexadecanol; 2-tetradecyloctadecanol; 2-hexadecyleicosanol; and unsaturated alcohols such as l-hexyl-3-ol; oleoyl alcohol (technically cis-9-octadecen-l-ol); 2,5-dimethyl-4-octyn-3,6-diol; 2, 4, 7, 9-tetramethyl-n-decin-4,7-diol; 3-dodecen-l-ol; and 3, 6-dimethyl-8-dodecen-l-ol. Since the invention is effective to alkoxylate all kinds of alcohols, including but not necessarily limited to saturated and unsaturated alcohols, saturated alcohols are preferred. Of these, polyalkylene glycols are preferred, with polyethylene glycol being most preferred. The alkoxylation reaction can be catalyzed using any suitable catalyst. The basic and acidic catalysts can be used. Suitable catalysts include, but are not necessarily limited to: potassium hydroxide; sodium hydroxide; aluminum alkylated fluorides; aluminum alkylated halides; organoaluminium-zinc compounds; acetates and naphthanates of calcium, strontium and barium; BF3 or GiF and metal alkyls or metal alkoxides; and hydrofluoric acids and metal alkoxides. The alkoxylation can be carried out at ambient pressure or at higher pressures or lower pressures, as long as the alkylene oxide is maintained in the vapor phase.

Normally, the pressure is about -14 to about 30 pounds per square inch (psi). Pressures less than about 20 psi are preferred. With reference to Figure 1, in order to conduct the reaction, a suitable reactor can be maintained under vacuum and the pressure can be modified to receive gas or vapor in the upper part of the reactor. The upper part of the stainless steel receptacle 16 containing liquid and gaseous ethylene oxide is connected with a pipe, hose or pipe 12 to the vent hole 14 in the main reactor . The flow of gas or vapor of ethylene oxide is controlled by the valves in the tube 12. The tube 12 preferably includes a "T-tube" with two valves 18 so that the ventilation hole 14 existing in the main reactor 15 can be used to charge the ethylene oxide vapor in the reactor 10 through the tube 12 and to ventilate the reactor 10. A more preferred alternative is to use a reactor with a separate vent hole to vent pressure to the reactor. The ethylene oxide vapors are allowed to diffuse from the receptacle 16 in the reactor 10 through the pipe 12. The separate vent hole is used to release the residual inert atmosphere in the reactor once all the charged ethylene oxide is reactive . Suitable alkylene oxide adduction materials are alkylene alpha and beta oxides, preferably ethylene oxide, propylene oxide and mixtures thereof, more preferably ethylene oxide. The alkoxylated product can have any desired content of the alkoxy adduction material. When an alcohol is ethoxylated, the ethylene oxide will normally comprise from about 20 to about 9 '). of the alkoxylated product. A suitable amount of catalyst for use in the reaction is from about 0.05 to about 10.0 weight percent of the catalyst based on the weight of the total reaction mixture. Preferred levels of the catalyst are from about U.l to about 6.0% by weight based on the weight of the total reaction mixture.

The invention will be better understood with reference to the following examples, which are provided to illustrate the invention, but not to limit the invention. EXAMPLE 1 After observing the undesirable flock in batches of heavy ethoxylated ethylene glycol (EIIEG), a series of experiments was performed to determine the cause of flocculation. No correlation could be observed between the floc percentage and the catalyst percentage (in this case, KOH); the reaction temperature (100-160 ° C); the ratio of oxide addition; or the hydroxyl number. E. EXAMPLE 2 The experiments were undertaken to determine whether ethoxylation using only ethylene oxide vapors could prevent the formation of floccules. In the next reaction, the ethylene oxide vapor was allowed to diffuse through a tube in a Parr reactor and in contact with the heavy ethylene glycol of instantaneous substrate (FHEG, a current of PEG produced by Oxychem from which the light final was separated). The following reactions were made: Rxn. # FHEG íCH ED ED ProducMuescte Base Base optara (g) aggreTotal to tra HO ff 'Th ff' gado Total (g) 1029.2 0.183 1029.4 0.26 320 0.08 116.: - 912.32 0.163 20 932.48 0.25 320 0.75 1319- 1028.1 82 151 (ED gas or V5DOT) 1028.1 1031.1 1.31 1028.1 0.917 1029 0.10 0.% 1.31 223 2.75 33.93 994.2 0.887 995.1 b. 0.06 0. ' 1.31 1.08 62. ni 931.35 0.831 20 20 952.18 1.28 267 1.08 931. 35 0.831 90 110 1042.2 1.17 270 6.8 931. 35 0.831 185 295 1227.2 0.99 270 4? 7 Equivalent in terms of mg of KOH per g of sample. "Reactor temperature The final listed sample 1319-151 exhibited an OH # of 435.6, The reaction samples 1319-151 remained clear without any trace of floccule during an observation period of several months Both 1319-147 and 1319-149 They were synthesized with liquid ethylene oxide and both developed flocculation E. EXAMPLE 3 To demonstrate that using liquid ethylene oxide for ethoxylation could promote the formation of floccules, a clear sample of PEG 200 (from a commercial vendor, similar to FHEG). ) was ethoxylated with liquid ethylene oxide under the following conditions: 1 In equivalence in terms of mg KOH per g of sample.

^ Reactor temperature. All samples developed floccules within 24 hours. E. EXAMPLE 4 In order to determine the results in Example 2, another reaction was conducted. The ethylene oxide vapors were added through a chemical bath tube (20 in Figure 1). The reaction is summarized in the following: The OH # of the sample with '.'30.2 FHE 3 was 448.7 The samples and products of all the previous reactions where the liquid ethylene oxide was loaded into the reactor developed floccules in less than 24-48 hours. In contrast, all samples of reaction 1319-159 were excellent clarity without flocculent after 5 days at room temperature, and remained clear during an observation period of several months. EXAMPLE 5 Seven more ethoxylations were conducted in Parr reactors using ethylene oxide in the vapor phase. The conditions and results are given in the following Table: The samples of 1319-163, -165, -167, -169, -173 and -175 largely remained clear through an observation period of several months. A number of the samples developed a slight posterior floccu and appeared slightly turbid. The quantities of floccules in these samples were less than those present in the samples synthesized with liquid EO. Also, the floccule was fine and was more evenly distributed. Ge believes that if the EO vapor is attracted from the EO container too quickly, the rapid effervescence or instantaneous boiling of the EO liquid could cause a few fine drops of EO to transport into the reactor, so the EO is incorporated. liquid in the reactions.

EXAMPLE 6 An experiment (1319-177) was performed using an atomizer to discharge EP vapors to the Parr reactor. The atomizer was installed in the chemical bath tube of one of the Parr reactors where the length of the chemical bath tube was shortened by cutting approximately two inches. In another experiment using a different reactor (1319-179), the EO vapors were charged to the vapor phase reactor with an initial acio pressure of approximately 5"of mercury.The conditions and results are summarized in the following table: The products were initially clear and remained clear through a period of observation of several months. E. EXAMPLE 7 In reaction 1319-183, the liquid EO was added or charged to the reactor containing FHEG through the same atomizer used for reaction 1319-177. The resulting product had flocculent. E.TEMPLO 8 The procedures of Example 2 were repeated. No vacuum was used. The conditions and results are summarized in the following Table: The samples were clear and remained clear through a period of observation of several months. E. ASSEMBLY 9 A mixture of PEG 200 and KOH flakes was loaded in a Parr reactor and dried. The procedures of Example 2 were then repeated. The conditions and results are summarized in the following Table: The samples were clear and remained clear during a period of observation of several months. E. EXAMPLE 10 The procedures of Example 9 were repeated using an initial vacuum of 10"inside the reactor.The reaction (1318-157) and the results are summarized in the following Table: The samples were clear and remained clear through a period of observation of several months. EXAMPLE 11 Finally, an ethoxylation with EO vapor was conducted in a 60 gallon reactor in the pilot plant. The reaction (1318-159) is summarized as follows: All samples remained clear for at least one month. Those of ordinary skill in the art will appreciate that many modifications can be made to the embodiments described herein without departing from the spirit of the present invention. Accordingly, the embodiments described herein are illustrative only and are not intended to limit the scope of the present invention.

Claims (24)

1. SUBMISSION: 1. A method comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate such an organic compound, wherein the alkylene oxide is maintained in vapor form during transport to the reaction vessel, during discharge into the reaction vessel, and during contact with the organic compound.
2. 2. The method of claim 1, wherein the organic compound is an alcohol.
3. 3. The method of claim 1, wherein the organic compound is a polyhydric alcohol.
4. The method of claim 1, wherein the organic compound is selected from the group consisting of aldehydes, ketones, amides, amines, organic acids, phenols and alkylphenols, polyols, mercaptans, alcohols, and saturated, unsaturated, linear polyhydric alcohols and branched.
5. 5. The method of claim 1, wherein the organic compound is selected from the group consisting of polyhydric alcohols containing a total of about 2 to about 30 carbon atoms and having the general formula Rx - C - OH wherein R, R and independently are selected from the group consisting of linear or branched acyclic groups, alicyclic groups, aryl groups, cyclic groups, and hydrogen and may contain one or more functional groups selected from the group consisting of amine, carboxyl, hydroxy halo, -ro, nitro, carbonyl and amide; aldehydes and ketones having boiling points above about 1U ° C, having from about 2 to about 30 carbon atoms and having the formula generates R1-C = O wherein R1 and R * "independently are selected from the group consisting of hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic zrzpos, and aryl groups, and may contain one or more functionalities selected from the group consisting of carboxyl groups, hydroxyl groups, halogen atoms, nitro groups, amine groups, and amide groups, the primary, secondary or tertiary amides having a boiling point above about 100 ° C, having from about 1 to about 30 carbon atoms and having they have the general formula 0 R2 1 / Rl - c - - N \ RJ wherein R1, R2 and R3 independently select from the group consisting of hydrogen, straight or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, and may contain one or more functional groups selected from the group consisting of hydroxyl groups, carboxyl, carbonyl groups, amino groups, nitro groups or halogen groups, primary, secondary, or tertiary amines having boiling points above about 100 ° C, having from about 1 to about 30 carbon atoms and having the general formula / Rl-N \ RJ wherein R1, R2 and R3 independently are selected from the group consisting of hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, or aryl groups, and may contain one or more functionalities selected from the group consisting of a hydroxyl group, a carbonyl group, a halogen atom, a carboxyl group, a nitro group, or an amide group; organic acids having a boiling point above about 100 ° C having from about 1 to about 30 carbon atoms, and having the general formula O Rx-C-OH wherein R1 is hydrogen, a linear or branched acyclic group, alicyclic group, cyclic group, or aryl group, and may contain one or more functionalities selected from the group consisting of a carbonyl group, a hydroxyl group, a halogen atom, a nitro group, an amine group, or a amide group; ? alkylphenols having a boiling point above about 100 ° C, having from about 6 to about 30 carbon atoms and having the general formula wherein R1, R, R3, R4 and R5 independently are selected from the group consisting of hydrogen, a halogen atom, a hydroxyl group, a nitro group, a carbonyl group, a linear or branched acyclic group, an amino group, a cyclic group, an aryl group or a substituted aryl group, and can 10 containing one or more functionalities selected from the group consisting of a halogen atom, an ether group, a nitro group, a carboxyl group, a carbonyl group, an amine group, an amide group, or a hydroxyl group; mercaptans of the general formula 15 R ^ - C - SH
6. 6. A method comprising contacting a polyalkylene glycol with an alkylene oxide in a reaction vessel under conditions effective for polyalkylene glycol alkoxylation, wherein the alkylene oxide is in the form of vapor before and during transport to the reaction vessel, during discharge in the reaction vessel and during contact with the polyalkylene glycol.
7. The method of claim 1, wherein the organic compound is selected from the group consisting of polyethylene glycol and polypropylene glycol.
8. The method of claim 1, wherein the organic compound is polyethylene glycol.
9. 9. A method comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound, wherein the alkylene oxide is selected from the group consisting of ethylene and propylene oxide, and the alkylene oxide is kept in vapor during transport to the reaction vessel, during discharge into the reaction vessel, and during contact in the organic compound.
10. The method of claim 2, wherein the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide.
11. 11. The method of claim 3, wherein the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide.
12. The method of claim 4, wherein the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide.
13. The method of claim 5, wherein the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide.
14. The method of claim 6, wherein the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide.
15. The method of claim 7, wherein the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide.
16. 16. The method of claim 8, wherein the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide.
17. 17. The method of claim 1, wherein the alkylene oxide is ethylene oxide.
18. 18. The method of claim 2, wherein the alkylene oxide is ethylene oxide.
19. 19. The method of claim 3, wherein the alkylene oxide is ethylene oxide.
20. 20. The method of claim 4, wherein the alkylene oxide is ethylene oxide.
21. 21. The method of claim 5, wherein the alkylene oxide is ethylene oxide.
22. 22. The method of claim 6, wherein the alkylene oxide is ethylene oxide.
23. 23. The method of claim 7, wherein the alkylene oxide is ethylene oxide. The method of claim 8, wherein the alkylene oxide is ethylene oxide. Extract of the Invention The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective for alkoxy or the organic compound. The alkylene oxide is kept in vapor form during transport to the reaction vessel, during discharge into the reaction vessel, and during contact of the organic compound with the lyalkylene oxide. The result is an alkoxylated product that contains less flocculant.