JP2018115154A - Method of manufacturing bisphenol compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method of manufacturing bisphenol less in coloring and small in APHA value, which can suitably be used as a raw material of a resin such as a polycarbonate resin.SOLUTION: There is provided a method of manufacturing a bisphenol compound using aldehyde and a phenol compound as raw materials, having a process for generating the bisphenol compound in the presence of an antioxidant of 10 to 5,000 mass.ppm based on the aldehyde. The aldehyde is preferably aliphatic aldehyde having 6 to 12 carbon atoms.SELECTED DRAWING: None

Description

The present invention relates to a method for producing a bisphenol compound. In detail, it is related with the manufacturing method of a bisphenol compound with little coloring.

Bisphenol compounds in which two phenolic structures are cross-linked with a methylene structure are raw materials for thermoplastic resins such as polycarbonate resins, polyester resins, acrylate resins, polyarylate resins, epoxy resins, polyimide resins, phenol resins, cyanate resins, etc. In addition to antioxidants such as thermosetting resin raw materials, curing agents, natural rubber, synthetic rubber and lubricating oil, developer of heat sensitive recording materials, addition of bactericides, antioxidants, fungicides, flame retardants, etc. It is widely used as an agent and is an important compound in the chemical industry. The bisphenol compound is a group of compounds having 2 substituents at the methylene bridge such as bisphenol A (hereinafter sometimes referred to as “ketone-type bisphenol compound”), bisphenol F, It can be classified into a group of compounds having 0 or 1 substituents at the methylene bridge such as bisphenol E (hereinafter sometimes referred to as “aldehyde-type bisphenol compound”). Among these, aldehyde-type bisphenol compounds are ketone-type bisphenols such as antioxidant properties due to having hydrogen atoms in the methylene bridge, improved melting points resulting from improved symmetry of the compounds, and improved crystal properties when made into resins. The compound is expected to be industrially applied because it is expected to exhibit various unique properties not found in the compound. In particular, bisphenol compounds produced from aliphatic aldehydes and phenolic compounds are expected to have a low melting point and excellent fluidity, and are expected to give new physical properties due to aldehyde-derived alkyl chains when used as resins. Therefore, it is a particularly important compound.
A bisphenol compound is usually produced by condensing an aldehyde or ketone with a phenol compound in the presence of an acid catalyst. Regarding the production of a bisphenol compound from an aliphatic aldehyde and a phenol compound, Patent Document 1 discloses an example carried out with a hydrochloric acid catalyst, and Non-Patent Document 1 discloses an example carried out with a sulfuric acid catalyst.

JP 59-131623 A

Industrial Chemistry Journal, 1965 (59), 94 pages

However, there is no description of colorability in the bisphenol compound obtained by the method of Patent Document 1, and the inventors have further investigated that the mixture after the condensation reaction tends to be colored yellow, and is required to be transparent. It turned out that it is not preferable as resin raw materials, such as resin. Further, there is a description that the bisphenol compound obtained by the method of Non-Patent Document 1 is reddish brown, which is also not preferable as a resin raw material such as polycarbonate resin. Furthermore, as a result of investigations by the inventors, it has been found that the color tendency of the reaction solution is the same even when other acid catalysts are used. From the above, a problem has been found that there is no method for producing a bisphenol compound with little colorability from an aldehyde and a phenol compound.
An object of this invention is to provide the manufacturing method of the bisphenol compound which reduced the coloring property from an aldehyde and a phenol compound in view of the said subject.

As a result of intensive studies, the present inventor has reduced the colorability in the process of producing a bisphenol compound using aldehyde and a phenol compound as raw materials by allowing a specific additive to exist in the production process within a certain range. The present inventors have found that the prepared bisphenol compound can be easily provided, and have completed the present invention.
That is, the gist of the present invention resides in the following [1] to [4].

[1] A method for producing a bisphenol compound using an aldehyde and a phenol compound as a raw material, comprising a step of producing the bisphenol compound in the presence of 10 to 5,000 mass ppm of an antioxidant with respect to the aldehyde. A method for producing a bisphenol compound.
[2] The method for producing a bisphenol compound according to [1], wherein the aldehyde is an aliphatic aldehyde having 6 to 12 carbon atoms.
[3] The method for producing a bisphenol compound according to [1] or [2], wherein the antioxidant contains a phenol-based antioxidant.
[4] The antioxidant includes α-tocopherol, [1] to [3]
] The manufacturing method of the bisphenol compound in any one of.

ADVANTAGE OF THE INVENTION According to this invention, it is a bisphenol compound which uses an aldehyde and a phenol compound as a raw material, and can provide easily the bisphenol compound with few coloring property which gives a bad influence when it is used as resin.

DESCRIPTION OF EMBODIMENTS Embodiments of the present invention will be described in detail below. However, the description of the constituent elements described below is an example of the embodiments of the present invention, and the present invention is described below unless the gist of the present invention is exceeded. It is not limited to. In addition, when using the expression “to” in the present specification, it is used as an expression including numerical values or physical property values before and after the expression.

<Aldehyde>
The aldehyde used in the present invention is preferably an aliphatic aldehyde, and particularly preferably an aliphatic aldehyde having 2 to 21 carbon atoms. Specific examples thereof include linear alkyl aldehydes, branched alkyl aldehydes, aliphatic aldehydes partially containing a cyclic structure, and aliphatic aldehydes containing unsaturated bonds.

Specific examples of the linear alkyl aldehyde include acetaldehyde, n-propanal,
n-butanal, n-pentanal, n-hexanal, n-heptanal, n-octanal, n-nonanal, n-decanal, n-undecanal, n-dodecanal, n
-Tridecanal, n-tetradecanal, n-pentadecanal, n-hexadecanal, n-heptadecanal, n-octadecanal, n-nonadecanal, n-nonadecylaldehyde, etc. -Nonanal, n-decanal, n-undecanal, and n-dodecanal are more preferable, and n-dodecanal is particularly preferable.

Specific examples of the branched alkyl aldehyde include isopropyl aldehyde, methyl propyl aldehyde, methyl butyraldehyde, methyl pentyl aldehyde, methyl hexyl aldehyde, methyl heptyl aldehyde, methyl octyl aldehyde, methyl nonyl aldehyde, methyl decyl aldehyde, methyl undecyl aldehyde Methyldodecyl aldehyde, methyl tridecyl aldehyde, methyl tetradecyl aldehyde, methyl pentadecyl aldehyde, methyl hexadecyl aldehyde, methyl heptadecyl aldehyde, methyl octadecyl aldehyde, methyl nonadecyl aldehyde,

t-Butylaldehyde, Dimethylpropylaldehyde, Dimethylbutyraldehyde, Dimethylpentylaldehyde, Dimethylhexylaldehyde, Dimethylheptylaldehyde, Dimethyloctylaldehyde, Dimethylnonylaldehyde, Dimethyldecylaldehyde, Dimethylundecylaldehyde, Dimethyldodecylaldehyde, Dimethyltridecylaldehyde , Dimethyltetradecylaldehyde, dimethylpentadecylaldehyde, dimethylhexadecylaldehyde, dimethylheptadecyl, dimethyloctadecylaldehyde,

Trimethylpentylaldehyde, trimethylhexylaldehyde, trimethylheptylaldehyde, trimethyltrimethyloctylaldehyde, trimethylnonylaldehyde,
Trimethyldecyl, trimethylundecylaldehyde, trimethyldodecylaldehyde,
Trimethyltridecyl aldehyde, trimethyl tetradecyl aldehyde, trimethyl pen 1 decyl aldehyde, trimethyl hexadecyl aldehyde, trimethyl heptadecyl aldehyde,

Ethyl propyl aldehyde, ethyl butyraldehyde, ethyl pentyl aldehyde, ethyl hexyl aldehyde, ethyl heptyl aldehyde, ethyl octyl aldehyde, ethyl nonyl aldehyde, ethyl decyl aldehyde, ethyl undecyl aldehyde, ethyl dodecyl aldehyde, ethyl tridecyl aldehyde, ethyl tetradecyl aldehyde, Ethyl pentadecyl aldehyde, ethyl hexadecyl aldehyde, ethyl heptadecyl aldehyde, ethyl octadecyl aldehyde,

Propylbutyraldehyde, propylpentylaldehyde, propylhexylaldehyde, propylheptylaldehyde, propyloctylaldehyde, propylnonylaldehyde, propyldecyl, propylundecylaldehyde, propyldodecylaldehyde,
Examples include propyltridecylaldehyde, propyltetradecylaldehyde, propylpentadecylaldehyde, propylhexadecylaldehyde, propylheptadecylaldehyde, etc., but isopropylaldehyde, methylpropylaldehyde, methylbutyraldehyde, methylpentylaldehyde, methylhexylaldehyde, methyl A branched alkyl aldehyde having a methyl group or an ethyl group as a branched chain, such as heptyl aldehyde, ethyl propyl aldehyde, ethyl butyraldehyde, ethyl pentyl aldehyde, ethyl hexyl aldehyde, etc. is preferable, and ethyl pentyl aldehyde is particularly preferable. In the example of the branched alkyl aldehyde, the position of branching is arbitrary.

Specific examples of the aliphatic aldehyde having a partial cyclic structure include formylcyclopropane,
Formylcyclobutane, formylcyclopentane, formylcyclohexane, formylcycloheptane, formylcyclooctane, formylcyclononane, formylcyclodecane, formylcycloundecane, formylcyclododecane, formylmethylcyclopentane, formylmethylcyclohexane, formylmethylcycloheptane, formylmethyl Cyclooctane, formylmethylcyclodecane, formylmethylcycloundecane, formylmethylcyclododecane, formyldimethylcyclopentane, formyldimethylcyclohexane, formyldimethylcycloheptane, formyldimethylcyclooctane, formyldimethylcyclononane, formyldimethylcyclodecane, formyldimethylcyclohexane Undecane, formyldimethylcyclo Decane, formylethylcyclopentane, formylethylcyclohexane, formylethylcycloheptane, formylethylcyclooctane, formylethylcyclononane, formylethylcyclodecane, formylethylcycloundecane, formylethylcyclododecane, formyldiethylcycloheptane, formyldiethylcyclo Octane, formyldiethylcyclononane, formyldiethylcyclodecane, formyldiethylcycloundecane, formyldiethylcyclododecane, formylpropylcyclopentane, formylpropylcyclohexane, formylpropylcycloheptane, formylpropylcyclooctane, formylpropylcyclononane, formylpropylcyclodecane , Formylpropylcycloundecane, formyl Examples thereof include propylcyclododecane, formylcyclohexylcyclohexane, 5-norbornane-2-carboxaldehyde, etc., but carbon numbers such as formylcyclopentane, formylcyclohexane, formylcycloheptane, formylcyclooctane, 5-norbornane-2-carboxaldehyde, etc. 6-9 cyclic alkyl aldehydes are preferred, and formylcyclohexane is particularly preferred.
In the example of the cyclic alkyl aldehyde, the substitution position of the formyl group is arbitrary.

Specific examples of the alkyl aldehyde having an unsaturated structure include one or more carbon-carbon double bonds in the structure of the linear alkyl aldehyde, the branched alkyl aldehyde, and the alkyl aldehyde having a partial cyclic structure. The structure is not particularly limited, and specific examples include n-propenyl aldehyde, n-butenyl aldehyde, n-pentenyl aldehyde, n-hexenyl aldehyde, n-heptenyl aldehyde, n-octenyl aldehyde, n-nonenyl aldehyde, n-decenyl aldehyde, n-undecenyl aldehyde,
n-dodecenyl aldehyde, n-tridecenyl aldehyde, n-tetradecenyl aldehyde, n-pentadecenyl aldehyde, n-hexadecenyl aldehyde, n-heptadecenyl aldehyde, n-octa Examples include decenyl aldehyde, n-nonadecenyl aldehyde, and 5-norbornene-2-carboxaldehyde.
In the example of the aliphatic aldehyde having an unsaturated bond, the position of the unsaturated bond is arbitrary.
These aliphatic aldehydes may be used alone or in combination of two or more.

<Phenol compound>
Specific examples of the phenol compound include phenol, o-cresol, m-cresol,
2,3-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 2-ethylphenol, 2-ethyl-6-methylphenol, 2-allylphenol, 2-isopropylphenol, 2-propylphenol, 2,3,6-trimethylphenol, 5,6,7,8-tetrahydro-1-naphthol, 2-sec-butylphenol, 2-tert-butylphenol, carvacrol, thymol, 2-tert-amylphenol, 6-tert- Butyl-o-cresol, 2-phenylphenol, 2-
Examples thereof include cyclohexylphenol, 2-amylou-5-methylphenol, 2,6-diisopropylphenol, 2-benzylphenol, 2-cyclohexyl-5-methylphenol and the like, among which phenol, o-cresol, 2,3-dimethyl Phenol,
2,5-dimethylphenol, 2,6-dimethylphenol, 2-ethylphenol, 2
-Monophenols having a hydrocarbon group of 3 or less carbon atoms such as ethyl-6-methylphenol, 2-isopropylphenol, 2-propylphenol, 2,3,6-trimethylphenol and the like are preferable, and phenol and o-cresol are more preferable. Phenol is preferred, with phenol being particularly preferred.

In addition, these phenol compounds may be used independently or may be used in mixture of 2 or more types.
The ratio of the aliphatic aldehyde to the phenolic compound used in the method for producing the bisphenol compound of the present invention is not particularly limited as long as the bisphenol compound is produced, but the phenolic compound is usually 1 mole times the aliphatic aldehyde. It is above, it is preferable that it is 2 mol times or more, and it is especially preferable that it is 3 mol times or more. It exists in the tendency which can manufacture a bisphenol compound efficiently because the quantity of a phenol compound is more than the said lower limit, and is preferable. On the other hand, it is usually 20 mol times or less, preferably 15 mol times or less, particularly preferably 10 mol times or less. It is preferable that the amount of the phenol compound is less than or equal to the above upper limit value because the load of the step of separating the unreacted phenol compound tends to be reduced in the method for producing a bisphenol compound of the present invention.

In the method for producing a bisphenol compound of the present invention, the aliphatic aldehyde and the phenol compound may be produced from a mixed state, or may be produced while either one or both are added continuously or intermittently. . In addition, it is preferable to produce the aldehyde by adding the aliphatic aldehyde continuously or intermittently in terms of easy production of the bisphenol compound.

<Acid catalyst>
Examples of the acid catalyst used in the method for producing a bisphenol compound from the aliphatic aldehyde and the phenol compound of the present invention (hereinafter sometimes referred to as the production method of the present invention) include inorganic acids such as phosphoric acid, oxalic acid, hydrochloric acid, sulfuric acid, and the like. Acid catalysts; organic acid catalysts such as acetic acid, trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid; acidic ion exchange resins such as Diaion SK104. Of these acid catalysts, use of a chlorinated or sulfonic acid catalyst such as hydrochloric acid, methane sulfonic acid, toluene sulfonic acid, Diaion SK104H (manufactured by Mitsubishi Chemical) makes it possible to produce the bisphenol compound of the present invention. It tends to be able to produce efficiently, and it is preferable to use hydrochloric acid or p-toluenesulfonic acid.

The amount of the acid catalyst used in the production method of the present invention is not particularly limited as long as the bisphenol compound of the present invention can be produced efficiently.
001 mol times or more, preferably 0.005 mol times or more, particularly preferably 0.00.
01 mole times or more. It exists in the tendency which can manufacture a bisphenol compound efficiently because an acid amount is more than the said lower limit, and is preferable. Moreover, it is 10 mol times or less normally, Preferably it is 5 mol times or less, Most preferably, it is 1 mol times or less. It is preferable that the acid amount is not more than the above upper limit value in the production method of the present invention because the load for separating the acid catalyst after use tends to be reduced.

<Antioxidant>
The production method of the present invention is characterized by having a step of producing a bisphenol compound in the presence of an antioxidant. Specific examples thereof include 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1.3.5-triazine-2,4,6.
-(1H, 3H, 5H) -trione (ADEKA STAB AO-20 manufactured by ADEKA), 4,4
', 4''-(1-methylpropanyl-3-ylidene) tris (6-tert-butyl-
m-cresol) (ADEKA STAB AO-30 manufactured by ADEKA), 6,6′-di-tert
-Butyl-4,4'-butylidene di-m-cresol (ADEKA STAB AO manufactured by ADEKA)
-40), octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate (ADEKA STAB AO-50 manufactured by ADEKA), pentaerythritol tetrakis [3- (3,5-di-tert- Butyl-4-hydroxyphenyl) propionate] (ADEKA STAB AO-60 manufactured by ADEKA), 3,9-bis [2- [3- (3-
tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy] -1,
1-dimethylethyl] -2,4,8,10-tetraoxaspiro [5,5] undecane (
ADEKA ADK STAB AO-80), 1,3,5-Tris (3,5-ji-ter)
t-butyl-4-hydroxyphenylmethyl) -2,4,6-trimethylbenzene (AD
Adakastab AO-330 manufactured by EKA, bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionic acid] [ethylenebis (oxyethylene)] (B
Irganox 245) manufactured by ASF, 2,6-di-tert-butyl-p-cresol,
4,4′-thiobis (2-tert-butyl-5-methylphenol) (Sumitomo Chemical Co., Ltd.)
milizerWX-R), 4,4′-butylidenebis- (6-tert-butyl-3-methylphenol) (Yoshinox BB manufactured by Mitsubishi Chemical Corporation), D-α-tocopherol, DL-α-
Phenolic antioxidants such as tocopherol, triphenylphosphine, 2-ethylhexyl diphenyl phosphite (ADEKA STAB C from ADEKA), tris (nonylphenyl) phosphite (ADEKA STAB 1178 from ADEKA), tetra-C _12-15-
Alkyl (propane-2,2-diylbis (4,1-phenylene) bis (phosphite)
) (Adeka Adeka Stub 1500), Tris (2,4-di-tert-butylphenyl) phosphite (Adeka Adeka Stub 2112), triisodecyl phosphite (Adeka Adeka Stub 3010), 3,9-di Octadecan-1-yl-
2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecane (A
DEKA ADK STAB PEP-8), 3,9-bis (2,4-di-tert-butylphenoxy) -2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5]
Undecane (ADEKA STAB PEP-24G manufactured by ADEKA), 3,9-bis (2,6-di-tert-butyl-4-methylphenoxy) -2,4,8,10-tetraoxa-3,
9-Diphosphaspiro [5.5] undecane (Adeka Corporation ADK STAB PEP-36
), 3,9-bis [2,4-bis (1-methyl-1-phenylethyl) phenoxy] -2
, 4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecane (AD
Adakastab PEP-45 manufactured by EKA) 2,4,8,10-tetra-tert-butyl-
6-[(2-Ethylhexane-1-yl) oxy] -12H-dibenzo [d, g] [1,
3,2] Dioxaphosphocin (ADEKA STAB HP-10 manufactured by ADEKA), bis (2,4
-Di-tert-butyl-6-methylphenyl) = ethyl = phosphite (Irgafos38 manufactured by BASF), tetrakis [(2,4-di-tert-butylphenyl) -1,1-biphenyl] -4-4 ′ Diylbisphosphonite (IrgafosP-EPQ manufactured by BASF)
), Etc., 2,2-bis ({[3- (dodecylthio) propionyl] oxy} methyl) -1,3-propanediyl = bis [3- (dodecylthio) propionate] (Adeka ADEKA STAB AO-412S), bis [2-methyl-4- (3-n-
Alkylthiopropionyloxy) -5-tert-butylphenyl] sulfide (AD
Adakastab AO-23 manufactured by EKA, distearyl 3,3′-thiodipropionate (A
DEKA ADK STAB AO-503A), 2,4-bis (octylthiomethyl) -6
-Methylphenol (Irganox 1520 manufactured by BASF), Dilauryl-3,3-thiodipropionate (Sumitizer TPL-R manufactured by Sumitomo Chemical), 2,2-bis ({
[3- (Dodecylthio) propionyl] oxy} methyl) -1,3-propanediyl = bis [3- (dodecylthio) propionate] (Sumitizer TP-D manufactured by Sumitomo Chemical Co., Ltd.)
), 2-mercaptobenzimidazole (Sumitomo Chemical Sumlizer MB) and other sulfur-based antioxidants, 3- (3,4-dimethylphenyl) -5,7-di-tert-butylbenzofuran-2 (3H) -one Lactone antioxidants such as (Irganox HP136 manufactured by BASF), 2-t-butyl-6- (3-t-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (manufactured by Sumitomo Chemical Co., Ltd. ( Sumilizer GM)
2- [1- (2-hydroxy-3,5-di-tert-pentylphenyl) ethyl]-
4,6-di-tert-pentylphenyl acrylate (Sumiliz, Sumitomo Chemical Co., Ltd.)
acrylate antioxidants such as erGS). Of these, ADK STAB AO-30, ADK STAB AO-40, Irganox 245, Irganox 1076
The presence of phenolic antioxidants such as Irganox 1010, 2,6-di-tert-butyl-p-cresol, Yoshinox BB, D-α-tocopherol, DL-α-tocopherol, etc. It is preferable in that the effect is more easily exhibited, and it is particularly preferable that DL-α-tocopherol is present.

In addition, the said antioxidant may be used independently or may be used in mixture of 2 or more types.
The amount of the antioxidant is 10 ppm by mass or more, preferably 50 ppm by mass or more, particularly preferably 100 ppm by mass or more, based on the aliphatic aldehyde that is usually used. It is in the tendency for the coloring reduction effect by antioxidant to be able to be exhibited effectively because the quantity of antioxidant is more than the above-mentioned lower limit, and it is preferred. On the other hand, it is usually 5,000 mass ppm or less, preferably 3,000 mass ppm or less, particularly preferably 2,000 mass ppm or less. When the amount of the antioxidant is equal to or lower than the upper limit of the previous period, it tends to be able to prevent coloring derived from the antioxidant itself, which is preferable.
The antioxidant may be added alone during the production process, or may be used in a state mixed with any of an aliphatic aldehyde, a phenol compound, a third component described later, an organic solvent, or an additive. In addition, it is preferable to use it in a state mixed with an aliphatic aldehyde because the effect of the antioxidant tends to be more easily exhibited.

In addition, the said antioxidant may be used independently or may be used in mixture of 2 or more types.
The amount of the antioxidant is 10 ppm by mass or more, preferably 50 ppm by mass or more, particularly preferably 100 ppm by mass or more, based on the aliphatic aldehyde that is usually used. It is in the tendency for the coloring reduction effect by antioxidant to be able to be exhibited effectively because the quantity of antioxidant is more than the above-mentioned lower limit, and it is preferred. On the other hand, it is usually 5,000 mass ppm or less, preferably 3,000 mass ppm or less, particularly preferably 2,000 mass ppm or less. When the amount of the antioxidant is not more than the above upper limit value, it tends to be able to prevent coloring derived from the antioxidant itself, which is preferable.
The antioxidant may be added alone during the production process, or may be used in a state mixed with any of an aliphatic aldehyde, a phenol compound, a third component described later, an organic solvent, or an additive. In addition, it is preferable to use it in a state mixed with an aliphatic aldehyde because the effect of the antioxidant tends to be more easily exhibited.

<Third component (stabilizer)>
In the production method of the present invention, the reaction system may contain a third component for the purpose of further stabilizing the aldehyde of the present invention and further suppressing side reactions and coloring during the production of the bisphenol of the present invention. Specific examples thereof include nitrogen-containing compounds such as triethanolamine and benzoguanamine; sulfur-containing aromatic compounds such as mercaptobenzimidazole; water and the like. Among these additives, the inclusion of a nitrogen-containing compound is preferable because the aldehyde of the present invention tends to be able to further suppress deterioration such as side reactions leading to coloring. On the other hand, it is preferable not to include these third components because the reactivity when the bisphenol compound of the present invention is used as a resin tends not to be hindered.
The amount of the third component is usually 1 ppm by mass or more, preferably 5 ppm by mass or more, particularly preferably 10 ppm by mass or more, based on the aldehyde of the present invention.
It is particularly preferably at least 00 ppm by mass, and most preferably at least 300 ppm by mass. On the other hand, it is usually 50,000 mass ppm or less, preferably 30,000 mass ppm or less, particularly preferably 10,000 mass ppm or less, and 1,000
It is particularly preferably 0 mass ppm or less, and most preferably 700 mass ppm or less. It exists in the tendency which can exhibit the effect of a 3rd component more because the quantity of a 3rd component exists in the said range, and is preferable.
These third components may be contained alone or in combination of two or more.

<Fourth component (reaction accelerator)>
In the production method of the present invention, the reaction system may contain a fourth component for the purpose of activating the condensation reaction. Specifically, quaternary ammonium salts such as tetraethylammonium bromide, tetrabutylammonium hydrosulfate, tetrabutylammonium chloride; methyl mercaptan, ethyl mercaptan, n-propyl mercaptan, 2-propanethiol, n-butyl mercaptan, sec-butyl Mercaptan, t-butyl mercaptan, n-pentyl mercaptan, 3-methyl-2-butanethiol, isoamyl mercaptan, n-hexyl mercaptan, cyclohexanethiol, n-heptyl mercaptan, n-octyl mercaptan, 2-ethyl-1-hexanethiol N-nonyl mercaptan, n-decyl mercaptan, n-undecyl mercaptan, n-dodecyl mercaptan, n-tetradecyl mercaptan, t rt- tetra decanethiol, n- hexadecyl mercaptan, n- octadecyl mercaptan, n- docosyl mercaptan,
1,2-ethanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,3-butanedithiol, 1,5-pentanedithiol, 1,10-decanedithiol, methyl thioglycolate, thioglycolic acid Ethyl, butyl thioglycolate, octyl thioglycolate, 2-ethylhexyl thioglycolate, methyl 2-mercaptopropionate, methyl 3-mercaptopropionate, ethyl 3-mercaptopropionate,
And sulfur-containing aliphatic compounds such as octadecyl 3-mercaptopropionate. Among these, it is preferable to use a sulfur-containing aliphatic compound as the fourth component because the production of the bisphenol compound of the present invention is easy. These fourth components may be used in a state of being supported on a resin or the like.

The amount of the fourth component used in the production method of the present invention is not particularly limited as long as the bisphenol compound of the present invention can be produced efficiently, but the amount of the fourth component is usually 0 with respect to the aldehyde of the present invention.
. 001 mol times or more, preferably 0.005 mol times or more, particularly preferably 0
. 01 mole times or more. It exists in the tendency which can manufacture a bisphenol compound efficiently because the quantity of a 4th component is more than the said lower limit, and is preferable. Moreover, it is 1 mol times or less normally, Preferably it is 0.5 mol times or less, Most preferably, it is 0.2 mol times or less. When the amount of the fourth component is not more than the above upper limit value, the load for separating the fourth component after use tends to be reduced during the production of the bisphenol compound, which is preferable.

<Solvent>
In the manufacturing method of this invention, you may react using a solvent. Specific examples of solvents include
C5-C18 linear hydrocarbon solvent such as n-pentane, n-hexane, n-heptane, n-octane, petroleum ether; C5-C18 branched hydrocarbon solvent such as isooctane; cyclohexane C5-18 cyclic hydrocarbon solvents such as cyclooctane and methylcyclohexane; water; alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitrile solvents such as acetonitrile; ether solvents such as dibutyl ether; methyl ethyl ketone and methyl isobutyl Ketone solvents such as ketones; ester solvents such as ethyl acetate and butyl acetate; nitrogen-containing solvents such as dimethylformamide and dimethylacetamide; sulfur-containing solvents such as dimethylsulfoxide and sulfolane; methylene chloride, chloroform, dichloroethane, and the like Chlorinated solvents; benzene, toluene, and aromatic hydrocarbon solvents such as xylene. In addition, it is preferable not to use these solvents or to use an aromatic hydrocarbon solvent in terms of easy production of the bisphenol compound of the present invention, and it is particularly preferable not to use a solvent.

The amount of the solvent used in the production method of the present invention (the step of producing a bisphenol compound in the presence of an antioxidant) is not particularly defined as long as the bisphenol compound can be produced efficiently, but the amount of the solvent relative to the aldehyde of the present invention is not limited. Usually, it is 0.1 mass times or more, preferably 0.2 mass times or more, particularly preferably 0.5 mass times or more. It is preferable that the amount of the solvent is not less than the lower limit value, since the effect of the solvent tends to be exhibited more efficiently during the production of the bisphenol compound. Moreover, it is 20 mass times or less normally, Preferably it is 10 mass times or less, Most preferably, it is 5 mass times or less. When the amount of the large solvent is less than or equal to the above upper limit value, the bisphenol compound tends to be efficiently produced, which is preferable.

<Reaction temperature>
The reaction temperature in the production method of the present invention is usually 0 ° C. or higher, preferably 15 ° C. or higher, particularly preferably 30 ° C. or higher. When the reaction temperature is equal to or higher than the lower limit, the reaction mixture tends to be prevented from solidifying, which is preferable. On the other hand, it is usually 150 ° C. or lower, preferably 120 ° C. or lower, particularly preferably 90 ° C. or lower. It exists in the tendency which can manufacture a bisphenol compound efficiently because reaction temperature is below the said upper limit, and is preferable.

<Purification>
The production method of the present invention may include a step of removing the used acid catalyst. Specific examples of the removal step include a neutralization step with a base, a removal step by dissolving in a solvent, a removal step by filtration, and the like. Among these, when using an inorganic acid catalyst or an organic acid catalyst as the acid catalyst, a neutralization step with a base is included, and when a heterogeneous catalyst is used, a removal step by filtration is included efficiently. Is preferable because it can be removed.
These removal steps may be used alone or in combination.

Specific examples of the base used in the neutralization step with a base include sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium acetate, potassium acetate, cesium acetate, sodium hydroxide, potassium hydroxide, phosphorus An inorganic base having an alkali metal atom or an alkaline earth metal atom, such as sodium monohydrogen phosphate, potassium monohydrogen phosphate, sodium phosphate, potassium phosphate, magnesium hydroxide, calcium hydroxide, sodium hydride, sodium amide; An organic base having an alkali metal atom or an alkaline earth metal atom such as sodium citrate, potassium citrate, sodium succinate, potassium succinate, calcium succinate, sodium methoxide, potassium methoxide, potassium tert-butoxide; Jin, aniline, triethylamine, N, N-dimethylaniline, morpholine, 1,4-diazabicyclo [2,2,2] octane, a nitrogen-containing compounds such as diazabicycloundecene and the like. Of these, sodium bicarbonate,
Potassium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium acetate, potassium acetate, cesium acetate, sodium hydroxide, potassium hydroxide, sodium monohydrogen phosphate, potassium monohydrogen phosphate, sodium phosphate, potassium phosphate, Magnesium hydroxide,
Use of a base having an alkali metal atom or alkaline earth metal atom such as calcium hydroxide, sodium hydride, sodium citrate, potassium citrate, sodium succinate, potassium succinate, etc. facilitates removal of the neutralized salt This is preferable. These bases may be used alone or in combination of two or more.

In the neutralization step, a second component may be added for the purpose of adjusting the acidity of the mixture. Specific examples thereof include organic acids such as acetic acid, citric acid, succinic acid and malic acid; heteroatoms other than oxygen such as phosphoric acid, sodium dihydrogen phosphate, potassium dihydrogen phosphate, ammonium chloride and monosodium citrate. And acids containing. The kind and amount of the second component are variously selected according to the kind and amount of the acid catalyst used in the reaction step and the base used in the neutralization step, and the acidity target value of the mixture after neutralization.

The mixture after the neutralization step is preferably weakly acidic or weakly basic because the stability of the bisphenol compound of the present invention tends to be improved. Note that the mixture is weakly acidic or weakly basic, when water is added to the mixture and the mass ratio of water and other components is adjusted to 1: 3, the pH of the aqueous layer is usually 2 or more, It is preferably 3 or more, particularly preferably 4 or more. On the other hand, it is usually 11 or less, preferably 10 or less, particularly preferably 9 or less. It is preferable that the pH of the aqueous layer is within the above range because the stability of the bisphenol compound of the present invention tends to be improved.
Specific examples of the solvent used in the removing step by dissolving in a solvent include water; organic solvents such as methanol, ethanol, propanol, dimethyl sulfoxide, diethyl ether, and N-methylpyrrolidone. Among these, it is preferable to use water in that the purification process can be simplified.

Filtering agents used in the removal step by filtration include powdered, crushed or spherical filter agents such as activated carbon, silica gel, activated clay, and diatomaceous earth; fiber or cloth such as filter paper, filter cloth, and thread wound filter And the like. These filtering agents are variously selected based on the properties of the acid catalyst used, the possibility of reuse of the acid catalyst, and the like.
The method for producing a bisphenol compound of the present invention is a step of precipitating the bisphenol compound of the present invention from a solvent containing at least one aliphatic hydrocarbon solvent from a mixture containing the bisphenol compound of the present invention (hereinafter referred to as a precipitation step). It is preferable to contain. Specific examples of the aliphatic hydrocarbon solvent include n-pentane, n-hexane, n-heptane, n-octane,
C5-C18 linear hydrocarbon solvent such as petroleum ether; C5 such as isooctane
-18 branched-chain hydrocarbon solvents; C5-C18 cyclic hydrocarbon solvents such as cyclohexane, cyclooctane, and methylcyclohexane. Among these, it is preferable to use a hydrocarbon solvent having 6 to 10 carbon atoms from the viewpoint that it is easy to remove the solvent from the bisphenol compound of the present invention, and it is a hydrocarbon solvent having 6 to 8 carbon atoms. More preferred. These hydrocarbon solvents may be used alone or in combination of two or more.

In addition, the above-described solvent may contain a solvent other than the aliphatic hydrocarbon solvent as the second solvent. Specific examples thereof include water; alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitrile solvents such as acetonitrile; ether solvents such as dibutyl ether; ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; ethyl acetate, butyl acetate and the like. Ester solvents; nitrogen-containing solvents such as dimethylformamide and dimethylacetamide; sulfur-containing solvents such as dimethylsulfoxide and sulfolane; methylene chloride;
Examples include chlorine-containing solvents such as chloroform and dichloroethane; aromatic hydrocarbon solvents such as benzene, toluene and xylene. Among these, it is preferable that either the alcohol solvent or the aromatic hydrocarbon solvent is contained as the second solvent in that the bisphenol compound of the present invention tends to be efficiently purified. These second solvents may be used alone or in combination of two or more.

The mixing ratio of the second solvent and the aliphatic hydrocarbon solvent is not particularly limited as long as the characteristics of the bisphenol compound of the present invention are not impaired, and may be appropriately set and used, but the configuration of the aliphatic hydrocarbon solvent in the total solvent The ratio is usually 10 to 99% by mass. It is preferable that the by-product is easily removed efficiently by setting the composition ratio of the aliphatic hydrocarbon solvent in the total solvent to the upper limit value or less. Moreover, since it can suppress that the bisphenol compound of this invention selectively melt | dissolves in a 2nd solvent and is removed, ie, a yield falls, it is preferable because it is more than the said lower limit. From such a viewpoint, the composition ratio of the aliphatic hydrocarbon solvent in the total solvent is more preferably 20 to 98% by mass, further preferably 25 to 97% by mass, and 30 to 96% by mass. It is particularly preferred.

The mixing ratio of the mixture containing the bisphenol compound and the above-mentioned solvent is not particularly defined as long as the bisphenol compound of the present invention can be efficiently precipitated, but the mass of the total solvent is usually based on the mixture containing the bisphenol compound of the present invention. The ratio is preferably 0.2 times or more, more preferably 0.5 times or more, and particularly preferably 1.0 times or more. On the other hand, it is preferably 100 times or less, more preferably 50 times or less, and particularly preferably 10 times or less.
Is less than double. When the mass ratio of all the solvents is equal to or higher than the above lower limit value, the mixture containing the bisphenol compound of the present invention tends to be preferentially precipitated. The manufacturing efficiency tends to improve, which is preferable.

When mixing the mixture containing the bisphenol compound as a main component and the solvent containing the at least one aliphatic hydrocarbon solvent, the aliphatic hydrocarbon solvent and the second solvent may be added separately or mixed in advance. And may be mixed with the mixture. In addition, it is preferable to mix a solvent previously from a viewpoint of improving the manufacturing efficiency of the bisphenol compound of this invention. Here, the temperature at the time of mixing the mixture containing the bisphenol compound of the present invention as a main component and the solvent containing at least one aliphatic hydrocarbon solvent is usually 0 ° C. or higher, preferably 20 ° C. or higher, particularly preferably. 40 ° C. or lower, usually the boiling point of the solvent or lower, preferably (the boiling point of the solvent−5) ° C. or lower,
Particularly preferably (boiling point of solvent−10) ° C. or lower. It is possible for the bisphenol compound of the present invention to be efficiently dissolved when it is not less than the above lower limit value and not more than the upper limit value. Here, when using 2 or more types of solvents mixed, the boiling point of said solvent represents the boiling point of the solvent after mixing.

The temperature of the precipitation step is not particularly limited as long as the properties of the bisphenol compound produced by the production method of the present invention are not impaired, and can be appropriately set, but is usually −20 ° C. or higher,
It is preferably −10 ° C. or higher, and particularly preferably 0 ° C. or higher. On the other hand, usually 7
It is 0 ° C. or lower, preferably 65 ° C. or lower, and particularly preferably 60 ° C. or lower. It exists in the tendency which can refine | purify the bisphenol compound of this invention efficiently because temperature is in the said range, and it is preferable.

In the precipitation step, a seed crystal of a bisphenol compound may be added in order to improve the precipitation efficiency of the bisphenol compound. The amount of the seed crystal is usually 0.0 by mass ratio with respect to the mixture containing the bisphenol compound as a main component in order to improve the production efficiency of the bisphenol compound.
It is 001 to 10%, preferably 0.0005 to 5%, and particularly preferably 0.001 to 1%.

The number of times of the precipitation step is variously selected depending on the degree of purification of the bisphenol compound of the present invention. However, from the viewpoint of simplifying the purification treatment, it is usually preferably 3 times or less and more preferably 2 times or less. Preferably, it is particularly preferably once.
You may wash | clean the powder of the bisphenol compound after the said precipitation process using the solvent for the purpose of surface washing | cleaning further. Specific examples of the solvent used include the hydrocarbon solvents and the solvents mentioned as the second component. The temperature of the main cleaning treatment is usually −20 ° C. or higher, preferably −1.
It is 0 ° C. or higher, particularly preferably 0 ° C. or higher, and is usually 70 ° C. or lower, preferably 60 ° C. or lower, particularly preferably 50 ° C. or lower. It exists in the tendency which can suppress dissolving the bisphenol compound of this invention excessively in the solvent for washing | cleaning because it is in the said range, and it is preferable.

Further heating the powder of the bisphenol compound obtained through the precipitation step and washing,
A bisphenol compound substantially free of a solvent may be obtained by performing a solvent removal treatment under reduced pressure, air drying, or the like. Here, the temperature at the time of the solvent removal treatment is usually 20 ° C. or higher and preferably 40 ° C. or higher in order to allow the solvent removal treatment to proceed smoothly. The upper limit of the temperature is usually not higher than the melting point of the phenol compound of the present invention, preferably 75 ° C. or lower, and particularly preferably 72 ° C. or lower.

[Reason for superior properties]
Hereinafter, the reason why coloring is suppressed in the bisphenol compound produced by the production method of the present invention will be described. A bisphenol compound produced from an aldehyde and a phenol compound is different from a bisphenol compound consisting of a ketone and a phenol compound such as bisphenol A, and has an active hydrogen atom at the condensation site thereof. It is thought that it is easy to become. It is considered that the addition of an appropriate amount of antioxidant during production can suppress the oxidation of the bisphenol compound and suppress the coloring. On the other hand, if the addition amount of the antioxidant is too large, there is a possibility that coloring derived from the oxidation product derived from itself may occur. Therefore, it is considered that the addition of an appropriate amount is effective.

[Usage]
The bisphenol compound obtained by the production method of the present invention is a polyether resin, a polyester resin, or a polyarylate resin used for various applications such as optical materials, recording materials, insulating materials, transparent materials, electronic materials, adhesive materials, and heat-resistant materials. , Components such as various thermoplastic resins such as polycarbonate resin, polyurethane resin, acrylic resin, various thermosetting resins such as epoxy resin, unsaturated polyester resin, phenol resin, polybenzoxazine resin, cyanate resin, curing agent, It can be used as an additive or a precursor thereof. Further, it is also useful as an additive such as a color developer such as a heat-sensitive recording material, an anti-fading agent, a bactericidal agent, and a fungicide and fungicide.
Among these, it is preferable to use as a raw material (monomer) of a thermoplastic resin or a thermosetting resin, and more preferable to use as a raw material of a polycarbonate resin or an epoxy resin, because good mechanical properties can be imparted. Moreover, it is also preferable to use it as a color developer, and it is particularly preferable to use it in combination with a leuco dye and a color change temperature adjusting agent.

Examples of the present invention are shown below, but the present invention is not limited thereto. N
-Dodecanal used what distilled n-dodecanal by Tokyo Chemical Industry Co., Ltd. was used. DL-α-tocopherol is manufactured by Tokyo Chemical Industry Co., Ltd., phenol is manufactured by Nacalai Tesque Co., Ltd., Irganox 1076 and Irganox 1010 are BAS.
A product manufactured by F Co., Ltd. and Yoshinox BB manufactured by Mitsubishi Chemical Corp. were used.

[Liquid color and coloring degree evaluation]
The liquid color was confirmed visually. The degree of coloring was determined by Hazen color number (APHA) analysis. APHA standard solution (1,000 degrees) manufactured by Kishida Chemical Co., Ltd. was diluted with pure water, and 10 degrees, 20 degrees, 30
Degrees, 40 degrees, 50 degrees, 70 degrees, 80 degrees, 90 degrees, 100 degrees, 125 degrees, 150 degrees, 200 degrees
APHA standard solutions at a temperature of 250 degrees, 300 degrees, 400 degrees, and 500 degrees were prepared.
The sample solution and the standard solution were put in 50 ml screw bottles, respectively, and the color tones were compared visually. According to the description of JIS K0071: 1998, the number of colors of the standard solution with the closest color tone of the sample solution was defined as the Hazen color number of the sample. In the case of an intermediate color between the two standard solutions, the larger value was used.
In addition, when APHA of a sample liquid exceeded 1,000 degree | times, toluene was added so that the volume of a sample liquid might become 2 times amount, the sample dilution liquid was created, and APHA of this dilution liquid was measured. If the APHA of the sample diluent exceeds 1,000 degrees, the AP of the original sample solution will be used for convenience.
HA was> 2,000 degrees.

<Example 1>
A mixture of n-dodecanal (5.0 g), DL-α-tocopherol (0.50 mg), phenol (13 g), and 35% by mass hydrochloric acid (0.17 g) was stirred with heating at 40 ° C. for 2 hours in a nitrogen atmosphere. The obtained reaction mixture was mixed with a 20% by mass aqueous sodium hydroxide solution (0.326).
Neutralized with g). The reaction solution after neutralization was pale yellow and Hazen color number was 125 degrees.

<Example 2>
A mixture of n-dodecanal (5.0 g), DL-α-tocopherol (2.5 mg), phenol (13 g), and 35% by mass hydrochloric acid (0.17 g) was heated and stirred at 40 ° C. for 2 hours in a nitrogen atmosphere. The obtained reaction mixture was mixed with a 20% by mass aqueous sodium hydroxide solution (0.326 g).
). The reaction solution after neutralization was pale yellow and Hazen color number was 125 degrees.

<Example 3>
A mixture of n-dodecanal (5.0 g), DL-α-tocopherol (2.5 mg), fail (13 g), and p-toluenesulfonic acid monohydrate (1.0 g) was added under nitrogen atmosphere.
The mixture was heated and stirred at 0 ° C. for 4 hours. The obtained reaction mixture was mixed with a 20% by mass aqueous sodium hydroxide solution (
1.05 g). The reaction solution after neutralization was yellow, and the Hazen color number was 400 degrees.

<Example 4>
A mixture of n-dodecanal (5.0 g), DL-α-tocopherol (5.0 mg), phenol (13 g) and p-toluenesulfonic acid monohydrate (1.0 g) was added under a nitrogen atmosphere.
The mixture was heated and stirred at 50 ° C. for 4 hours. The obtained reaction mixture was neutralized with 20% by mass aqueous sodium hydroxide solution (1.05 g). The reaction solution after neutralization was yellow, and the Hazen color number was 500 degrees.

<Example 5>
A mixture of n-dodecanal (5.0 g), Irganox 1076 (2.5 mg), phenol (13 g) and p-toluenesulfonic acid monohydrate (1.0 g) was added under nitrogen atmosphere.
The mixture was heated and stirred at 0 ° C. for 4 hours. The obtained reaction mixture was mixed with a 20% by mass aqueous sodium hydroxide solution (
1.05 g). The reaction solution after neutralization was yellow, and the Hazen color number was 1,000 degrees.

<Example 6>
A mixture of n-dodecanal (5.0 g), Irganox 1010 (2.5 mg), phenol (13 g) and p-toluenesulfonic acid monohydrate (1.0 g) was added under nitrogen atmosphere.
The mixture was heated and stirred at 0 ° C. for 4 hours. The obtained reaction mixture was mixed with a 20% by mass aqueous sodium hydroxide solution (
1.05 g). The reaction solution after neutralization was yellow, and the Hazen color number was 1,000 degrees.

<Example 7>
n-dodecanal (5.0 g), Yoshinox BB (2.5 mg), phenol (13
g) A mixture of p-toluenesulfonic acid monohydrate (1.0 g) was heated and stirred at 50 ° C. for 4 hours under a nitrogen atmosphere. The obtained reaction mixture was mixed with a 20% by mass aqueous sodium hydroxide solution (1.0
Neutralized at 5 g). The reaction solution after neutralization was yellow, and the Hazen color number was 1,000 degrees.

<Example 8>
n-dodecanal (5.0 g), DL-α-tocopherol (2.5 mg), benzoguanamine (2.5 mg), phenol (13 g), p-toluenesulfonic acid monohydrate (1
. 0 g) was heated and stirred at 50 ° C. for 4 hours under a nitrogen atmosphere. The obtained reaction mixture was neutralized with 20% by mass aqueous sodium hydroxide solution (1.05 g). The reaction solution after neutralization was yellow, and the Hazen color number was 400 degrees.

<Comparative Example 1>
A mixture of n-dodecanal (5.0 g), phenol (13 g), and concentrated hydrochloric acid (0.17 g) was heated and stirred at 40 ° C. for 2 hours under a nitrogen atmosphere. The obtained reaction mixture was neutralized with 20% by mass aqueous sodium hydroxide solution (1.05 g). The reaction solution after neutralization was pale yellow, and the Hazen color number was 300 degrees.

<Comparative example 2>
A mixture of n-dodecanal (5.0 g), DL-α-tocopherol (50 mg), phenol (13 g), and concentrated hydrochloric acid (0.17 g) was heated and stirred at 40 ° C. for 2 hours under a nitrogen atmosphere. The obtained reaction mixture was neutralized with 20% by mass aqueous sodium hydroxide solution (1.05 g). The reaction solution after neutralization was yellow, and the Hazen color number was 400 degrees.

<Comparative Example 3>
A mixture of n-dodecanal (5.0 g), phenol (13 g), and p-toluenesulfonic acid monohydrate (1.0 g) was heated and stirred at 50 ° C. for 4 hours under a nitrogen atmosphere. The obtained reaction mixture was neutralized with 20% by mass aqueous sodium hydroxide solution (1.05 g). The reaction solution after neutralization was reddish brown, and the Hazen color number was> 2,000 degrees.

The results of Examples and Comparative Examples are summarized in Table 1 below. When Examples 1-2 and Comparative Example 1 and Examples 3-6 and Comparative Example 3 are compared, coloring of the reaction solution reacted in the presence of the antioxidant is suppressed regardless of the type of the acid catalyst. It is clear. Moreover, when Examples 1-2 and Comparative Example 2 are compared, it turns out that coloring of a reaction liquid will deteriorate rather when there are too many amounts of antioxidants. This is thought to be due to the strong influence of the antioxidant itself being partially decomposed and colored during the reaction.

Claims (4)

In the method for producing a bisphenol compound using an aldehyde and a phenol compound as a raw material, the method includes a step of generating the bisphenol compound in the presence of 10 to 5,000 mass ppm of an antioxidant with respect to the aldehyde. A method for producing a bisphenol compound. The method for producing a bisphenol compound according to claim 1, wherein the aldehyde is an aliphatic aldehyde having 6 to 12 carbon atoms. The said antioxidant contains a phenolic antioxidant, The claim 1 or 2 characterized by the above-mentioned.
The manufacturing method of the bisphenol compound as described in 2. The method for producing a bisphenol compound according to any one of claims 1 to 3, wherein the antioxidant contains α-tocopherol.