diff --git a/j2k/src/org/jetbrains/kotlin/j2k/ExpressionConverter.kt b/j2k/src/org/jetbrains/kotlin/j2k/ExpressionConverter.kt
index 09bdfabdc22..f21bc3340ef 100644
--- a/j2k/src/org/jetbrains/kotlin/j2k/ExpressionConverter.kt
+++ b/j2k/src/org/jetbrains/kotlin/j2k/ExpressionConverter.kt
@@ -20,6 +20,7 @@ package org.jetbrains.kotlin.j2k
 import com.intellij.openapi.project.Project
 import com.intellij.psi.*
 import com.intellij.psi.search.GlobalSearchScope
+import com.intellij.psi.tree.IElementType
 import com.intellij.psi.util.MethodSignature
 import com.intellij.psi.util.MethodSignatureUtil
 import com.intellij.psi.util.PsiTreeUtil
@@ -109,10 +110,19 @@ class DefaultExpressionConverter : JavaElementVisitor(), ExpressionConverter {
     override fun visitBinaryExpression(expression: PsiBinaryExpression) {
         val left = expression.lOperand
         val right = expression.rOperand
-        var leftConverted = codeConverter.convertExpression(left, null)
-        var rightConverted = codeConverter.convertExpression(right, null)
 
         val operationTokenType = expression.operationTokenType
+
+        val leftOperandExpectedType = getOperandExpectedType(left, right, operationTokenType)
+        var leftConverted = codeConverter.convertExpression(left, leftOperandExpectedType)
+        var rightConverted = codeConverter.convertExpression(
+                right,
+                if (leftOperandExpectedType == null)
+                    getOperandExpectedType(right, left, operationTokenType)
+                else
+                    null
+        )
+
         if (operationTokenType in NON_NULL_OPERAND_OPS) {
             leftConverted = BangBangExpression.surroundIfNullable(leftConverted)
             rightConverted = BangBangExpression.surroundIfNullable(rightConverted)
@@ -132,6 +142,54 @@ class DefaultExpressionConverter : JavaElementVisitor(), ExpressionConverter {
         }
     }
 
+    private fun getOperandExpectedType(current: PsiExpression?, other: PsiExpression?, operationTokenType: IElementType): PsiType? {
+        val currentType = current?.type
+        val otherType = other?.type
+        if (currentType !is PsiPrimitiveType || otherType !is PsiPrimitiveType) return null
+        if (currentType == PsiType.BOOLEAN || otherType == PsiType.BOOLEAN) return null
+
+        if (operationTokenType == JavaTokenType.EQEQ
+            || operationTokenType == JavaTokenType.NE
+            || currentType == PsiType.CHAR) {
+            if (currentType < otherType) return otherType
+        }
+
+        return null
+    }
+
+    infix operator fun PsiPrimitiveType.compareTo(other: PsiPrimitiveType): Int {
+        return when(this) {
+            other -> 0
+            PsiType.BYTE -> when(other) {
+                PsiType.CHAR -> 1
+                else -> -1
+            }
+            PsiType.SHORT -> when(other) {
+                PsiType.CHAR,
+                PsiType.BYTE -> 1
+                else -> -1
+            }
+            PsiType.INT -> when(other) {
+                PsiType.BYTE,
+                PsiType.SHORT,
+                PsiType.CHAR -> 1
+                else -> -1
+            }
+            PsiType.LONG -> when(other) {
+                PsiType.DOUBLE,
+                PsiType.FLOAT -> -1
+                else -> 1
+            }
+            PsiType.FLOAT -> when(other) {
+                PsiType.DOUBLE -> -1
+                else -> 1
+            }
+            PsiType.DOUBLE -> 1
+            PsiType.CHAR -> -1
+            else -> throw AssertionError("Unknown primitive type $this")
+        }
+    }
+
     private fun canKeepEqEq(left: PsiExpression, right: PsiExpression?): Boolean {
         if (left.isNullLiteral() || (right?.isNullLiteral() ?: false)) return true
         val type = left.type
diff --git a/j2k/testData/fileOrElement/issues/kt-9997.java b/j2k/testData/fileOrElement/issues/kt-9997.java
index ab2d2808051..13a49837010 100644
--- a/j2k/testData/fileOrElement/issues/kt-9997.java
+++ b/j2k/testData/fileOrElement/issues/kt-9997.java
@@ -1,5 +1,5 @@
 class A {
-    public void foo() {
+    public void equals() {
         int i = 1;
         byte b = 1;
         short s = 1;
@@ -7,5 +7,132 @@ class A {
         double d = 1.0;
         float f = 1.0f;
         char c = 1;
+
+        t(i == i);
+        t(i == b);
+        t(i == s);
+        t(i == l);
+        t(i == d);
+        t(i == f);
+        t(i == c);
+
+        t(b == i);
+        t(b == b);
+        t(b == s);
+        t(b == l);
+        t(b == d);
+        t(b == f);
+        t(b == c);
+
+        t(s == i);
+        t(s == b);
+        t(s == s);
+        t(s == l);
+        t(s == d);
+        t(s == f);
+        t(s == c);
+
+        t(l == i);
+        t(l == b);
+        t(l == s);
+        t(l == l);
+        t(l == d);
+        t(l == f);
+        t(l == c);
+
+        t(d == i);
+        t(d == b);
+        t(d == s);
+        t(d == l);
+        t(d == d);
+        t(d == f);
+        t(d == c);
+
+        t(f == i);
+        t(f == b);
+        t(f == s);
+        t(f == l);
+        t(f == d);
+        t(f == f);
+        t(f == c);
+
+        t(c == i);
+        t(c == b);
+        t(c == s);
+        t(c == l);
+        t(c == d);
+        t(c == f);
+        t(c == c);
+
+        t(i != d);
+    }
+
+    public void compare() {
+        int i = 1;
+        byte b = 1;
+        short s = 1;
+        long l = 1;
+        double d = 1.0;
+        float f = 1.0f;
+        char c = 1;
+
+        t(i > i);
+        t(i > b);
+        t(i > s);
+        t(i > l);
+        t(i > d);
+        t(i > f);
+        t(i > c);
+
+        t(b > i);
+        t(b > b);
+        t(b > s);
+        t(b > l);
+        t(b > d);
+        t(b > f);
+        t(b > c);
+
+        t(s > i);
+        t(s > b);
+        t(s > s);
+        t(s > l);
+        t(s > d);
+        t(s > f);
+        t(s > c);
+
+        t(l > i);
+        t(l > b);
+        t(l > s);
+        t(l > l);
+        t(l > d);
+        t(l > f);
+        t(l > c);
+
+        t(d > i);
+        t(d > b);
+        t(d > s);
+        t(d > l);
+        t(d > d);
+        t(d > f);
+        t(d > c);
+
+        t(f > i);
+        t(f > b);
+        t(f > s);
+        t(f > l);
+        t(f > d);
+        t(f > f);
+        t(f > c);
+
+        t(c > i);
+        t(c > b);
+        t(c > s);
+        t(c > l);
+        t(c > d);
+        t(c > f);
+        t(c > c);
+    }
+
+    private void t(boolean b) {
     }
 }
\ No newline at end of file
diff --git a/j2k/testData/fileOrElement/issues/kt-9997.kt b/j2k/testData/fileOrElement/issues/kt-9997.kt
index 9c38834a0a0..e2987b1265b 100644
--- a/j2k/testData/fileOrElement/issues/kt-9997.kt
+++ b/j2k/testData/fileOrElement/issues/kt-9997.kt
@@ -1,5 +1,5 @@
 internal class A {
-    fun foo() {
+    fun equals() {
         val i = 1
         val b: Byte = 1
         val s: Short = 1
@@ -7,5 +7,132 @@ internal class A {
         val d = 1.0
         val f = 1.0f
         val c: Char = 1.toChar()
+
+        t(i == i)
+        t(i == b.toInt())
+        t(i == s.toInt())
+        t(i.toLong() == l)
+        t(i.toDouble() == d)
+        t(i.toFloat() == f)
+        t(i == c.toInt())
+
+        t(b.toInt() == i)
+        t(b == b)
+        t(b.toShort() == s)
+        t(b.toLong() == l)
+        t(b.toDouble() == d)
+        t(b.toFloat() == f)
+        t(b == c.toByte())
+
+        t(s.toInt() == i)
+        t(s == b.toShort())
+        t(s == s)
+        t(s.toLong() == l)
+        t(s.toDouble() == d)
+        t(s.toFloat() == f)
+        t(s == c.toShort())
+
+        t(l == i.toLong())
+        t(l == b.toLong())
+        t(l == s.toLong())
+        t(l == l)
+        t(l.toDouble() == d)
+        t(l.toFloat() == f)
+        t(l == c.toLong())
+
+        t(d == i.toDouble())
+        t(d == b.toDouble())
+        t(d == s.toDouble())
+        t(d == l.toDouble())
+        t(d == d)
+        t(d == f.toDouble())
+        t(d == c.toDouble())
+
+        t(f == i.toFloat())
+        t(f == b.toFloat())
+        t(f == s.toFloat())
+        t(f == l.toFloat())
+        t(f.toDouble() == d)
+        t(f == f)
+        t(f == c.toFloat())
+
+        t(c.toInt() == i)
+        t(c.toByte() == b)
+        t(c.toShort() == s)
+        t(c.toLong() == l)
+        t(c.toDouble() == d)
+        t(c.toFloat() == f)
+        t(c == c)
+
+        t(i.toDouble() != d)
+    }
+
+    fun compare() {
+        val i = 1
+        val b: Byte = 1
+        val s: Short = 1
+        val l: Long = 1
+        val d = 1.0
+        val f = 1.0f
+        val c: Char = 1.toChar()
+
+        t(i > i)
+        t(i > b)
+        t(i > s)
+        t(i > l)
+        t(i > d)
+        t(i > f)
+        t(i > c.toInt())
+
+        t(b > i)
+        t(b > b)
+        t(b > s)
+        t(b > l)
+        t(b > d)
+        t(b > f)
+        t(b > c.toByte())
+
+        t(s > i)
+        t(s > b)
+        t(s > s)
+        t(s > l)
+        t(s > d)
+        t(s > f)
+        t(s > c.toShort())
+
+        t(l > i)
+        t(l > b)
+        t(l > s)
+        t(l > l)
+        t(l > d)
+        t(l > f)
+        t(l > c.toLong())
+
+        t(d > i)
+        t(d > b)
+        t(d > s)
+        t(d > l)
+        t(d > d)
+        t(d > f)
+        t(d > c.toDouble())
+
+        t(f > i)
+        t(f > b)
+        t(f > s)
+        t(f > l)
+        t(f > d)
+        t(f > f)
+        t(f > c.toFloat())
+
+        t(c.toInt() > i)
+        t(c.toByte() > b)
+        t(c.toShort() > s)
+        t(c.toLong() > l)
+        t(c.toDouble() > d)
+        t(c.toFloat() > f)
+        t(c > c)
+    }
+
+    private fun t(b: Boolean) {
     }
 }
\ No newline at end of file
diff --git a/j2k/testData/fileOrElement/issues/operationsWithChar.java b/j2k/testData/fileOrElement/issues/operationsWithChar.java
new file mode 100644
index 00000000000..71413469660
--- /dev/null
+++ b/j2k/testData/fileOrElement/issues/operationsWithChar.java
@@ -0,0 +1,45 @@
+//file
+class Test {
+    public void operationsWithChar() {
+        char c = 1;
+        int i = 1;
+
+        b(i > c);
+        b(i >= c);
+        b(i < c);
+        b(i <= c);
+
+        b(c > i);
+        b(c >= i);
+        b(c < i);
+        b(c <= i);
+
+        b(c == i);
+        b(c != i);
+        b(i == c);
+        b(i != c);
+
+        i(i + c);
+        i(i - c);
+        i(i / c);
+        i(i * c);
+        i(i % c);
+        i(i | c);
+        i(i & c);
+        i(i << c);
+        i(i >> c);
+
+        i(c + i);
+        i(c - i);
+        i(c / i);
+        i(c * i);
+        i(c % i);
+        i(c | i);
+        i(c & i);
+        i(c << i);
+        i(c >> i);
+    }
+
+    public void b(boolean b) {}
+    public void i(int i) {}
+}
\ No newline at end of file
diff --git a/j2k/testData/fileOrElement/issues/operationsWithChar.kt b/j2k/testData/fileOrElement/issues/operationsWithChar.kt
new file mode 100644
index 00000000000..2a2a8ddbf32
--- /dev/null
+++ b/j2k/testData/fileOrElement/issues/operationsWithChar.kt
@@ -0,0 +1,47 @@
+internal class Test {
+    fun operationsWithChar() {
+        val c: Char = 1.toChar()
+        val i = 1
+
+        b(i > c.toInt())
+        b(i >= c.toInt())
+        b(i < c.toInt())
+        b(i <= c.toInt())
+
+        b(c.toInt() > i)
+        b(c.toInt() >= i)
+        b(c.toInt() < i)
+        b(c.toInt() <= i)
+
+        b(c.toInt() == i)
+        b(c.toInt() != i)
+        b(i == c.toInt())
+        b(i != c.toInt())
+
+        i(i + c.toInt())
+        i(i - c.toInt())
+        i(i / c.toInt())
+        i(i * c.toInt())
+        i(i % c.toInt())
+        i(i or c.toInt())
+        i(i and c.toInt())
+        i(i shl c.toInt())
+        i(i shr c.toInt())
+
+        i(c.toInt() + i)
+        i(c.toInt() - i)
+        i(c.toInt() / i)
+        i(c.toInt() * i)
+        i(c.toInt() % i)
+        i(c.toInt() or i)
+        i(c.toInt() and i)
+        i(c.toInt() shl i)
+        i(c.toInt() shr i)
+    }
+
+    fun b(b: Boolean) {
+    }
+
+    fun i(i: Int) {
+    }
+}
\ No newline at end of file
diff --git a/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterForWebDemoTestGenerated.java b/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterForWebDemoTestGenerated.java
index 636519bde0e..0fb57b0fbb8 100644
--- a/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterForWebDemoTestGenerated.java
+++ b/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterForWebDemoTestGenerated.java
@@ -2791,6 +2791,12 @@ public class JavaToKotlinConverterForWebDemoTestGenerated extends AbstractJavaTo
             doTest(fileName);
         }
 
+        @TestMetadata("operationsWithChar.java")
+        public void testOperationsWithChar() throws Exception {
+            String fileName = KotlinTestUtils.navigationMetadata("j2k/testData/fileOrElement/issues/operationsWithChar.java");
+            doTest(fileName);
+        }
+
         @TestMetadata("qualifyStatic.java")
         public void testQualifyStatic() throws Exception {
             String fileName = KotlinTestUtils.navigationMetadata("j2k/testData/fileOrElement/issues/qualifyStatic.java");
diff --git a/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterSingleFileTestGenerated.java b/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterSingleFileTestGenerated.java
index 7c11381f4ad..dd27c6a8583 100644
--- a/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterSingleFileTestGenerated.java
+++ b/j2k/tests/org/jetbrains/kotlin/j2k/JavaToKotlinConverterSingleFileTestGenerated.java
@@ -2791,6 +2791,12 @@ public class JavaToKotlinConverterSingleFileTestGenerated extends AbstractJavaTo
             doTest(fileName);
         }
 
+        @TestMetadata("operationsWithChar.java")
+        public void testOperationsWithChar() throws Exception {
+            String fileName = KotlinTestUtils.navigationMetadata("j2k/testData/fileOrElement/issues/operationsWithChar.java");
+            doTest(fileName);
+        }
+
         @TestMetadata("qualifyStatic.java")
         public void testQualifyStatic() throws Exception {
             String fileName = KotlinTestUtils.navigationMetadata("j2k/testData/fileOrElement/issues/qualifyStatic.java");